by Throne
Dylan didn't fit well into most groups of guys. Not only didn't he play sports, but he didn't follow or bet on them. He wasn't interested in cars. And though he had a longing for girls, his record with them was a string of failures. The last problem was especially hurtful to him. He wanted to date someone and couldn't understand his inability to do it. He was short, but so were plenty of girls. And his slender build shouldn't be a deterrent. His modest frame made it easy for him to dress well, with nice designer shirts and straight legged jeans, plus a selection of crewneck sweaters and the like. He took care of his grooming, using gel on his full head of auburn hair, as well as emollients and exfoliating products on his skin. Still, something was lacking.
After he got into college he joined the drama club to try to build a social life. But as shy as he was, they usually relegated him to handling props and costumes. He preferred the latter, because carrying a dress was easier than assembling a set. Besides, Dylan had gotten the idea that bringing dresses to girls would be a good way to get to know them, and that might lead to more. Particularly with one girl -- Julia. He was especially excited when the group decided to present a modernized version of Othello. The actors could improvise and rework their lines if they kept to the Shakespearean feel and the director approved.
Everything was progressing nicely when one of the cast members dropped out. He had been playing Clown and, for some reason, several others thought of Dylan as a replacement. When the young man objected that he hadn't acted on stage yet, they pointed out that the character only had fourteen lines in the original play. Dylan could certainly hold his own with such a small part, especially since he didn't have to remember the lines exactly, but only their essence. He accepted it with a mix of unfamiliar pride and nervous trepidation. He was most motivated to make the effort, however, by the chance to see more of Julia. In his imagination she was his fair maiden, and he her noble gallant. She was the finest actress in the group.
Julia was a willowy blond, her flaxen hair falling to her milky shoulders. Her bust was rather full for the rest of her figure, and showed itself to good advantage in the Elizabethan dresses she wore when performing The Bard. Often she would play opposite Tyler, who was tall and handsome, his reddish-gold hair worn short and neat. He was also on the swimming team. For this play they had a recently transferred student joining them. That was Javon, who shared Tyler's superior height but not his Scandinavian complexion. The new student was Black and excelled at basketball.
So there Dylan was, still handling costumes, but now about to wear one himself. He liked to go to the wardrobe area when no one else was around, just to appreciate the workmanship and design of them. Sometimes he would hold a mutton-sleeved shirt or pair of breeches up in front of himself and admire the effect in one of the full length mirrors backstage. He would perch a jaunty cap, perhaps with a long feather projecting from it, atop his head and strike extravagantly theatrical poses. Once or twice, thinking of how young men had portrayed women before females were permitted to perform on stage, he would even pose with a dress in front of him, marveling at the intricate brocade work and flowing skirts.
Once, he took a dress that Julia had recently worn and hugged it against his narrow chest, inhaling the lingering traces of her perfume. That made his heart beat faster and, even though it was embarrassing to admit it, even to himself, his penis throb. He'd had some problems in that latter area back in high school. In the locker room some of the bigger guys, and most of the guys were bigger, had taunted him about having a small dick. He tried to take it good naturedly, telling himself that it was simply how guys behaved in that environment. He also told himself that he was of average size down there, and that the impression of him being small was because they weren't allowing for his lesser stature, and the fact that his body parts were in proportion with that.
One afternoon, at a rehearsal, he determined to listen more closely to the leads as they spoke their rewritten dialogue, in the hope that it would help him to do better with his own. Julia, as Desdemona, swept out from behind one of the flats. Tyler, in the title role, entered from the opposite side. Javon, who of course portrayed the Moor, waited patiently in the wings. Their director, the gay but not effeminate Professor Smyth, suggested that they simply improvise a scene to warm up.
Tyler went to Julia and proclaimed, "Verily, charmer of my heart, the blossoms of the fields would lower their heads in modest surrender to your beauty."
She looked directly into his eyes and responded, "And the stags of the forest declare themselves less than thou in poise and courage."
Javon swept in and declaimed, "But hark, what darkness from offstage struts?"
Everyone laughed at his intentionally humorous line. He bowed to his fellow players.
Tyler asked, "Good friend, brother of my trust, why is your countenance clouded?"
Now serious, Javon said, "There is a storm aborning and it casts its shadow far. Fair weather is foul and foul fair when men do not speak their minds truly. Even the devil may quote scripture to his purpose. And brothers we may be, good Othello, but are we bonded by barefaced trust or that which but wears the mask of trust, and thus leads us to false fellowship?"
Barely missing a beat, Tyler told him, "What have such as we to fear of truth made its opposite? What silver tongued imp would speak midnight words to us on such a noon-bright day?"
The Black actor spoke with sly persuasiveness when he said, "Who indeed, when friend is foe and foe friend?"
Julia put herself between them, as if it discourage an impending conflict. "Pray, list to me, good men. For good you both are, though perturbing riddles might your minds confuse and sway."
The three of them stood there, with no one sure who should provide the next line. As one they broke up laughing. The director joined them, clapping without moving his hands very far apart.
"Bravo," he congratulated. "That's the sort of thing I want to hear. You have the rhythm and intonations I'm listening for. And I like what I've heard the last week or so, with a soupcon of contemporary English. I hope you've been working together and writing down the lines you come up with."
They all agreed that they'd been doing just that. Professor Smyth suggested that just Julia and Javon work on one particular scene together. Tyler said that if they wanted to talk with him later, they could just call. He left with the professor, but Dylan remained, unseen, lurking in the shadows offstage. The two actors ran some lines, exchanging them impressively. Javon offered a different way for them to stand in relationship to each other.
Julia told him, "You have a terrific sense of stagecraft. I can picture you directing."
He said confidently, "I know someone I'd like to direct."
"Who," she asked coyly. "Me?"
"That's right. In a love scene."
She extended her hand and he took it, bringing it to his lips so he could place a kiss on it. Then he gently pulled her toward him. She allowed it willingly and they embraced. Julia turned up her face and he lowered his, both meeting in a tender kiss. His large hands ran down her back and settled on the top of the rise of her bottom. From his hiding place, Dylan froze up inside. He watched as the recipient of his passionate-but-unvoiced love kissed Javon again, with growing fervor. Dylan backed into the dressing closet where he would be invisible. He was squeezed between two female costumes hanging from the crowded overhead bar. Instead of being discouraged by what he was witnessing, he felt himself become more emotionally involved with Julia. Seeing her taken by someone else made her even more desirable. His already deep crush swelled into obsession.
Dylan watched intently as they alternately kissed and talked. Javon was so confident and relaxed. She was obviously smitten with him. But she was still somewhat shy around his overwhelming masculinity. Dylan could see the conflict in her body language. It was like something you might learn in an acting class. Except that this was real. She finally stepped away from Javon and held up her hands.
"Really," she said breathily. "We've got to slow down. I mean, I don't want this to stop but..."
When she couldn't finish her sentence, the Black student offered, "But it's all happening too fast. Right? No problem, angel. Slow and steady. How about if we get together after tomorrow's rehearsal? Go out for coffee. Or a drink, if you'd like." He took her hand in both his. "It's what we both want."
She brought her hand up to her chest, so that his hands were between her breasts. "Thank you, Javon. It's like you can read my mind. Tomorrow would be fine." She smiled impishly. "Give me a chance to catch my breath."
"And give me time to think about you and how sweet you are."
They kissed once more. Javon looked directly toward where Dylan was cowering. Then the Black stud walked Julia out with his arm around her shoulders, her head leaning against him. Dylan was trembling from unfamiliar feelings. It was somehow exciting to see her with that superior male. And to witness how she melted under his subtle approach. Still between those two dresses, he held the sleeve of one against his cheek as his other hand drifted downward. Almost without knowing he was doing it, he put his fingers against his crotch and moved them up and down, ever so slowly. The paired sensations of that sleeve and his self-stimulation worked so well together.
His thoughts went back to how young guys had historically played female parts. It was a perfectly normal occurrence. And it would be a good acting exercise for him to try it. He stepped out of that confined space, reached back, and took the dress he had been fondling. It was gorgeous, with short ruffles at the cuffs, a high neck, buttons down the front, a corset waist, and billowing, ankle-length skirts. There were even breast forms sewn into it. Maybe it actually had been worn by a guy before.
In a trance, images of Julia and Javon still dominating his mind, he unzipped the back and set it aside. It would be awkward and uncomfortable to still have his own clothes on under it. Dylan began unbuttoning his shirt. He was impressed that his erection was still 100%. His fingers massaged it lightly for a minute. He reached into his half opened shirt and felt his nipples, which added to his arousal and mesmerized state. Soon he was naked, taking deep but calm breaths as he stepped into the dress, got his arms into the sleeves, and reached around to zip himself into it. The raised neck fit close against his throat and the insides of those breast pads rubbed against his chest intimately.
A new thought flashed into his consciousness. What if Julia had worn this very dress? Did he dare to believe that? Dylan wanted to pay tribute to her, to express his affection, even though she wasn't there. He could be Julia, if only for a short time. He could aspire to that ideal, though it was plainly unobtainable. Dylan took a step, and then another. He raised one arm and made a broad gesture that could be seen from the back rows. His steps were small and feminine. A wiggle became apparent in his walk. He tilted up his small chin and licked his lips. He was dedicating his mini-performance to the girl with who he was so taken.
Dylan sashayed back to the wardrobe and picked a small round hat. It had fake gemstones set around its sides and a short veil in front. He smoothed the netting over his upper face and puckered up his lips to make them more girlish. When he got in front of one of the dressing mirrors he was stunned by the effect. Though he had never worn anything feminine like this before, it seemed very familiar and, more importantly, right. At the same time, another part of his brain was telling him that it was wrong and shameful. Yet how could anything that felt so good be bad? He decided to get back into his street clothes and give himself time to sort everything out.
When he was naked again, he couldn't resist embracing the dress, as if it was a fusion of the girl he longed for and his own idealized version of himself as her. It was all so confusing. Holding the dress against him, he dared to grip his small erection through the layers of material and stroke it until he moaned. No, he had to stop. Was he gay or something, reacting this way to crossdressing himself? And what about being turned on by peeping at Julia and Javon's physical contact? Why had that been so stimulating and unforgettable? Yes, he definitely had to get away from here and restore a sense of normalcy. After all, he always had the option to return and try dressing up again. Just to see how it effected him. He assured himself that he could stop anytime he pleased.
The next day after classes there was one more work session on the play. Another play was going to precede theirs. The sets for that one had been finished during the afternoon. There was a modern looking bedroom interior, and a bed in the middle of the floor. Dylan again watched from the sidelines. He then got to run his lines, which he was having trouble with even though there were so few of them. His part involved confronting a musician who was playing too loudly and annoying the master of Dylan's character. The other actor had been toying with the lines and called Dylan, as the servant Clown, onto the stage. The guy, portly and swaggering, took his place. Dylan uneasily put himself in front of him.
The guy said, "Just follow my lead." He took a moment to fuss with the collar of his shirt, as if he was in costume and was using some acting technique. Suddenly he looked Dylan in the eye and said, "What, good sir? Why do you interrupt our music?"
"It's..." Dylan was aware of the three principals watching him, especially Julia. "It is too much... or too loud, for my Master."
"Do you not appreciate it yourself? Are you a music maker?"
"I... I am not?"
"And yet, but a moment ago, I clearly heard you sound an unfragrant note. What inspired such an effort?"
"I... played no music... Sir."
"You played an air that an ass might play after it eats too many apples. The ass plays his special instrument, whereby hangs a tale."
"I... played that pleasant note... because it was in my heart," he improvised, trying to keep up.
"It would seem sure, minstrel of repasts past, that it issued from a lower region."
That line was met with laughter and spontaneous applause. Dylan was lost and clueless. Javon came out and clapped him hard on the back. Julia wagged her finger teasingly at the uncomprehending performer. Tyler went and congratulated the student playing a musician. Professor Smyth said they would keep the lines in, and that he thought Dylan was very convincing as a fool. The next hour went well and then everyone was ready to leave.
Julia and Javon were making plenty of eye contact with each other. Dylan faded into the background, hoping for a replay of their previous behavior. He was denied that, however, as they limited themselves to a few chaste kisses. But there was a change as Julia pressed her pelvis against Javon's and held it there, her generous bust partly flattened as she hugged him tightly. When she stepped away there was an unmistakable bulge between his legs and running partway down one thigh. It was huge. Dylan couldn't keep from comparing himself to what he was seeing. It contradicted the smaller student's belief that his own penis was average size. But then he told himself that he was still of normal dimensions, and the Black guy was well above the middle range.
Julia reached out hesitantly and ran her fingertips along that impressive length. She pressed her body against his again, this time moving her hips as she did so. Her eyes strayed to the bed in the corner of the stage. She licked her lips nervously. But then Javon moved back and the moment passed.
He told her, "I know someplace more comfortable and private. If you don't mind a short wait."
She said breathily, "All right, Javon. It's just that I've never been around someone quite like you."
"Yeah," he told her without modesty. "I get it. And you'll get it later, girl. Right now let's take a drive and talk, let you make sure you're thinking clear."
Was he being a gentleman? Dylan wondered. Or just enjoying how obviously eager she was? Either way, they left together, Julia with both hands on his upper arm, feeling his muscular bicep. Dylan had to sit down after they were gone. He felt as out of breath as she had been. It was like he had an emotional link to Julia. When he reached behind him, his hand brushed the hem of one of the dresses hanging there. He caressed it softly, pulled it forward, and kissed it tenderly. He pictured beautiful Julia wearing it as he did that. Like after the last rehearsal, Dylan's pecker got stiff. There was no pause for rationalizing this time as he rapidly stripped and got into the dress. Dylan did a reprise of his pantomime, mincing around, adding some more arm movements, and posing in front of the mirror.
Then came a moment of decision. He wanted to touch himself as he had done the other time, but he also wanted to go further. To go all the way, if that term could be applied to a lovelorn young man with only his hand to comfort him. He turned away from his reflection, hoisted up the heavy skirts of the dress, and got a grip on his dick. It was electrifying. He began to stroke himself, at first rapidly, but then at a more measured tempo, not wanting to rush through to the end. He kept it up for several minutes before daring to slowly turn back and face his image in the glass. It was so strange to see himself covered up in that lovely dress from neck to where he was holding it up. Dylan's face, so smooth and with such fine features, didn't announce his maleness. He saw how androgynous he could appear, and that amplified the effect of being in that dress, the one that Julia might have worn.
As his confidence rose, he began striking poses like he had done yesterday. Then he broke away to hook the dress up in front, using large safety pins. Now he could have his hands free. That allowed him to finger-comb his hair, run his hands down his sides, and raise the dress in back so he could turn around and look over his shoulder at the reflection of his shapely buttocks. He stuck his tongue out at himself and giggled at the sight. Facing his reflection once more, Dylan resumed masturbating. He moved away, got a second dress, and went to the bed. When he laid back on the mattress, it was as if he was in another world. He spread the second dress on top of himself, so that he felt completely enclosed by the feminine garments. His hand kept pumping. He shoved the fingers of his other hand into his mouth and closed his jaws. Moaning loudly into the improvised gag, he climbed toward a climax. Before he could consider the consequences, his little dick spurted. His orgasm made him arch his back for a moment before he collapsed back into an exhausted daze, ******* of his surroundings.
Dylan pushed the heavy dress covering him to the side and it dropped to the floor. With the one he was wearing still pinned up, he remained in that state for almost a quarter of an hour. His mini-adventure into fantasy had been so erotic that he was still feeling aroused. He played with his spent penis, using his own spunk as lube. Undoing the front of the dress, he spread the halves of the bodice and used his other hand to play with his receptive nipples. His member didn't get hard again but it was so nice just to be handling it. He writhed his hips, eyes closed and mouth opened. That went on for a timeless time, until he slowly came back to reality.
That was when he got the second dress off the floor and saw that he had shot his mess all over it. What if someone spotted that? And they somehow realized it was him who did it? After all, he was getting known as the 'costume guy'. Dylan sat on the edge of the bed with his head hung. The idea of having his secret practices ******* was heart-stopping. Then he had an inspiration. He was the only one there. No one would know if he -- did he dare? -- if he took it home with him. Naturally, he would only be doing that so he could clean the garment. That was all. And maybe try it on again. Once. Or twice. So he smuggled it out of the building and put it lovingly into the trunk of his car.
As soon as he got home he snuck it into his room and spread it out on his bed. The stains he had made were mostly dried. He folded the dress so that they were covered. Then he got completely undressed and lay on top of it. The contact of all that smooth material against his soft body was wonderful. He lay there relishing the sensations that were running through him. And there was no rush to get the dress back. If he rearranged a few of the others, no one would notice its absence. And if they needed that specific one he could -- well -- think of something. Maybe say that he had moved a few to the backup storage area. Sure. That would cover him.
The new production had started its run, but the theater was empty after each performance. Over the next week and a half, he enjoyed several more episodes of playing dress-up on the vacant stage and playing with himself at the same time. The more times he got spots on the dresses, the less important each one seemed. And he was slipping them out of there to smuggle home, so no one need ever know. Dylan was in deepening denial but he didn't see it that way. He was simply... experimenting. One of the interesting discoveries he made was that he didn't want to masturbate with the dresses at his place. He loved wearing them there, and it got his little prick standing up every time. But jerking off was only a thrill when he was alone on the stage. Maybe it was because that was where Julia was so often. Or it was just the knowledge that he was doing something very forbidden, and even risky. Whatever the explanation, he couldn't stop what he was doing and, more importantly, where he was doing it.
Dylan went to that deep storage area just to see what else might be there. He was delighted by what turned up. There were several dresses that were somehow extra racy. They were still period ones, with full skirts and fancy detailing, long sleeves and high necks. But they were tailored differently and hugged his body in ways the others hadn't. When he looked in the mirror now he saw not a demure woman of the past who might sometimes become sexually abandoned. Instead he saw a lascivious girl who craved male attention and was ready to reciprocate. He was in one of those, on the bed, the skirt bunched up around his waist, happily pulling his small penis, when everything changed.
From the dark he heard a male voice say, "Busted!"
Another called out, "And surrounded."
As Dylan lay there, trying unsuccessfully to push the skirt back down over his naked lower body, several figures emerged from the shadows. The first was Javon, neatly dressed as if for a date. The other three, also Black, looked more thuggish. They penned him in on the bed and one reached out to grab the hem of the skirt and pull it up even higher than it had been. Several phones appeared in dark hands and pictures were taken.
Javon said, "Look at what we got here, men. The white fairy princess all dressed up for the ball. Looking for her prince. Preferably one with a super-size cock."
"She-it," said one of the Black guys. "Maybe we ought to enroll in this place."
"What?" Dylan reached for the hem of his dress again but an angry glance from the guy who had pulled it up stopped him. "I'm not a fairy. I was just... uh... method acting. Getting into a role."
"Whoa," Javon interrupted. "You're playing Clown, the easiest part in Othello. And he sure ain't no pansy cross dresser. Plus, unless I'm forgetting my Shakespeare, there's no scene where he jacks his Jones. Right?"
"Well, yes. I was thinking more of how boys used to play girls in the old days."
"Right. I know my Shakespeare 101. I know that they used to have the stage direction, 'ENTER: Dressed As Girl'. And I know that got shortened to 'drag'. As in, I still don't know what you're doing there in drag, pulling your miniature pud. The only answer I can figure out is that you are a stone faggot wimp sissy. Am I right or am I right?"
"Not... the way you mean it... I just like to... dress this way. But I only started doing it recently."
More pictures were taken. Javon snapped at him to get up. "And don't give me anymore sorry excuses. From here on in, you just do what me and my crew tell you. Otherwise, the shots they been taking are going to go viral. Understood?"
"Go...? You would...? But then I'd be..." It all sank in and Dylan stood there in the dress that was so sexy in a historical way. "Yes, Sir."
"That's more like it. Now you're skirt fell down and I didn't say that was okay." He looked at the other three young Black men. "Did any of you dogs say it was okay? No?" His attention returned to Dylan. "So let's get it back up where it was, candy ass."
Dylan unenthusiastically gathered up the skirt in front, revealing his penis, which was now limp from all the upset. He stood there with his thighs pressed together in a failed attempt at modesty.
Javon went on, "So here's what you're going to do. First, you're almost hairless down there. But I don't want to see that peach fuzz growing above your baby size dick. So tonight you make sure to get rid of it. Buy yourself one of those handy razors like the girls all use. And some girl style shaving cream. And while you're shaving down there, get rid of anymore you have anywhere else. I want you clean and pink all over, like a bitch."
As if to reinforce Javon's words, one of his backups stepped in, fists balled at his sides, and gave Dylan an angry scowl. "Yo. Tell the man you going to do what he says."
"Yes, Sir. Yes, Javon. I'll do that. Tonight. Like you said." His voice was quivering. He wished they would allow him to cover himself.
"And then," Javon continued, "you going to meet up with us, tomorrow night at eight. We'll all get together in the old gym. Now that the new one's done being built, they leave the other locked up. But I got myself a key. So you report for sissy duty and we'll be there to help you get into the new part you'll be playing. Damn, you said you was method acting. Well, you going to get into the method real deep, and with us four to be your acting coaches. Going to help you get into the roll of sissy who don't want to have them pictures sent to the campus cops, and administration, and even Professor Smyth, who might like them, if you know what I mean."
"I... all right," Dylan conceded in defeat. "The old gym tomorrow at eight."
One of the other guys said, "How about if he bring a dress. A real old-time slutty one like he got now."
"I shouldn't," Dylan objected. "I already have too many at my place and..." He ran out of words. Clearly, they didn't care.
Javon made a mental note of that unintended revelation. He said, "Just be there, girly girl. With the dress. Now how about a few more poses for me and my posse? Like get on your knees with -- " He went to a table and picked up a plastic bottle of hair gel. " -- with this in your hand. First up, hold it alongside that shrunk up dick, so everybody can see how small it really is. Then get yourself hard again. It'll be fun for us to watch you do that. And do the size comparison a second time. You still won't come out looking too good. Then, for the big finish, give that bottle some licking, and get your sissy lips around the top of it, like its a cock you be sucking off. Me and my buddy's will make sure there're plenty of pictures, just in case you need more persuasion later."
Dylan followed those mortifying directions, while the quartet or Black tormentors laughed and took many more pictures. They even sent some of them to friends, just for fun, which proved to their victim how ready they were to ****** him more widely. They taunted him too, about how gay he acted, how small his dick was, and how he was lucky he wasn't into girls, because no female would be interested in him with the bad news he had between his legs.
At last, with the foursome satisfied and Dylan feeling exhausted, on the verge of a mini-breakdown, Javon's three friends left. The student in the dress looked at his fellow actor.
"But," Dylan wanted to know, "how did you find out what I was doing in here?"
"Well, stupid, you screwed up and did the humpty dance with your hand in one of the dresses Julia plans to wear for the real performances. And then you didn't take care of them pecker tracks. It freaked her to find your little sissy shots on her dress. She knew something was up. Then she told me because, you know, I'm her boyfriend. And we figured you were doing it right here, and you'd seen me and Julia getting to know each other. You did spy on us -- right?" After Dylan confessed, Javon went on, "Then I decided to catch you at your nasty game. So I came in, real quite-like, and saw what you was doing. From there it was easy to get my boys and set up this -- let's call it -- sissy intervention. Now we're going to help you get in touch with your real self. The queer inside."
"But, I'm not that way. Honestly."
"Maybe not. I've seen you getting all dreamy when you look at Julia. But I think your sissy side is the boss of you. It's like some of that truth they teach us in psychology class. Hey, maybe I can get a term paper out of this."
"Please, no," Dylan pleaded.
"That was me funning you. But the other part is deadly serious. Tomorrow night. Eight. You know where. See you then, sweet cheeks."
After that Dylan had a restless night. All the next day in classes his mind was elsewhere. After classes he had time to kill. As he wandered around campus, he kept thinking that people were looking at him with knowledge of his secrets. At 7:30 he went to get a dress from the theater. He held it against him and tried to think positive thoughts about Julia. But she was the one who had outed him. And Javon might have told her what they'd discovered. Maybe even shown her some of those incriminating photos. He was devastated. Well, he told himself, he had to get this over with. Dylan decided that, if he endured more of their torment, and tried to act like the situation wasn't overly serious, they would just lose interest in upsetting him and that would be the end of it. Sure. It wasn't like they were going to do more than make fun of him and have their cruel entertainment. Was it?
He got to the darkened old gym precisely at eight, figuring that tardiness was a bad idea. The door was unlocked and there was a light on in the locker room. He had bad memories of locker rooms past, where classmates had seen and mocked his supposedly undersized endowment. He went to where light was showing under the door and, not sure how to approach them, knocked respectfully.
There was laughter from inside and Javon's voice told him, "Come on in, missy."
Dylan entered the locker room and found all four of them waiting. One of them, who he had heard Javon call Tyler, told him to get naked. With their eyes on him, the sole white person in the room had to strip down. He stood there shifting his feet until Tyler barked at him to stay still. The threatening Black figure came close to him and put his hand on Dylan's bare shoulder with easy familiarity.
He said, "Hey, boy, you got to trust us. All we're doing her is settling a score. You spied on our main man and his woman. You know who I mean. That blond girl who loves spreading her legs for his big... black... pussy-splitter. So we have to do what we have to do." His hand slid down Dylan's back and caressed his bottom. "Then, since you look like a white girl yourself, it just makes sense for us to treat you like one. And for you to play along. Get into the part. You know, cause your an actor and all. Or actress." He laughed at his own humor. The others joined in. "But we don't want to make it too rough on you." He moved his hand to Dylan's wrist and gripped it tighter than the student would have preferred. Tyler rubbed his thumb over Dylan's palm and said, "Now one thing you got that's real girly is how soft you are. This hand is damn soft. Feels like a pussy almost. And a pussy feels good on a cock. So how about you put on that slutty dress, get down on your knees, take my rod out of my pants, and give me some hand pussy. You want to do that for me? Just to help make things right?" When Dylan was too scared to speak, Tyler added, "Or would you rather do something else girly for me, instead?"
"No, Sir. I mean, yes, Sir. I'll do that with my hand. Just please, not the other thing."
The barely veiled threat set Dylan into action. He got the dress and, with all of them still eyeing him and snickering, put it on. Having Tyler call it slutty made him understand that, just as he'd seen it that way before, others could perceive it the same way. Dylan suddenly felt like a courtesan or, perhaps more accurately, a fallen woman. Once he was dressed he sank to his knees in front of the waiting Black guy. His unsteady hands came up and he began to undo Tyler's pants. Less than a minute later, despite clumsiness born of fear, he had Tyler's cock freed and in his hand. It was alarmingly big, like Javon's. As soon as Dylan began to gently knead it, the length began to grow. It quickly went from six inches soft to eight hard.
"That's my little snowflake," Tyler encouraged. "You take care of me and I won't have to do nothing bad to you. Show me you want to be a good sissy. Let the other brothers know that you're the kind that satisfies."
Dylan got his second hand into the action, using it to hold and manipulate the knob while he continued to stroke the thick shaft. Tyler hummed a few tuneless bars under his breath. He told Dylan to take his time and that they had all night if they needed it. The kneeling young man sniffled and bit his lips. His new rationalization was that they just wanted to prove how much they could control him. It was something they needed, to feed their egos. Fine. He would submit to this and it would let them feel victorious. After that he could put all these indignities behind him. He kept working on the heavy organ, his fingers stretched around it, the contrast between his pale skin and the darker shades of Tyler's body so vivid.
"There you go," Tyler said between deep breaths. "You got me right on the edge, girl. Now take me the rest of the way."
The way Dylan was positioned, if Tyler shot now, it was going to get all over Dylan's face and the front of the dress. He started trying to lean to the side but Javon saw what he was doing and understood why.
"Hey, sissy," Javon told him. "Watch your posture. Get that back straight. You don't want that sexy dress to get all scrunched up."
When Dylan did as he was told, it put him back in the line of fire. Tyler grunted and his cock spurted. A gob of white cream caught Dylan in the cheek. The next one struck him in the chin. And the third landed on the formerly clean bodice of his dress. Tyler took half a minute to relax after his burst of pleasure. He seized Dylan's arm and brought it up so he could wipe the end of his cock on the sleeve. He took some pictures of Dylan's messy face and reminded the others to get shots.
Tyler said, "Next", and another of Javon's off-campus friends stepped in.
This one told Dylan he wanted his balls massaged and that, if he did it too hard, he would get his own balls treated in ways he wouldn't enjoy. The sufferer's knees were getting sore. He wanted to wipe off his face but was afraid of angering his captors. Besides, he didn't want to use his sleeve and get the dress even dirtier. The standing figure took several pictures while he was being stroked. This time was a lot like before and a load was fired against Dylan's closed mouth, chest, and into his lap. It went on like that. The third guy wanted his cock talked to, for Dylan to use a lisping voice to tell the long member how much he loved fondling it. That ended with the cock's owner groaning something about busting a nut and then suiting his actions to the words. Dylan was beginning to feel like he was going to be soaked through. In fact, he could feel dampness seeping through the fabric in a few spots.
The only Black man left unserved was Javon. But he wouldn't want to be hand-pumped because he was dating Julia. Having sex with Dylan's dream girl. And from all evidence, emptying his balls frequently with her willing participation. Yet Dylan's initial assumption was wrong. Javon did want his impressive meat manipulated. He chuckled as Dylan got it out of his pants and began stroking it, leading to an engorgement that made it the largest one yet. With his thumbs on its sensitive underside and his fingertips on its top, Dylan performed unhurried, two-handed maneuvers. Javon grinned down at him, as if he was gloating at both the white guy's helplessness and the fact that Javon had taken the object of his longing away from him. As clear fluid appeared at the tip of Javon's penis, Dylan began to quietly sob.
The big man kept him at it for nearly a half hour, while the others drank beer and ate pretzels. They even handed their leader a can that he took occasional swigs from, as Dylan submissively tended to his rampant organ. At last signs appeared that Javon was about to relinquish control to his urges. Dylan dreaded having his features spattered with semen one more time. He subtly tried to angle that massive tool lower so its output would all land on the already messy dress. But Javon saw what he was doing and ordered him to aim it straight at his own face. Javon felt hot tears rolling down his warm cheeks. He gave three more pumps and the well-primed prick fired point blank at his eyes, nose and mouth. He got the full amount on his writhing face. There was so much that it ran down and dripped from his chin. His nose began to run. He blinked cream out of his right eye.
Javon laughed. "I seen you take care of your skin with that crap you sneak onto it during rehearsals. Some expensive girl-type product. Well, now you got a full facial, and it didn't cost you a thing. How about you thank me for that."
"I... yes, Sir. Thank you, Javon. Thank you for my... free facial."
"Hey, no problem, buddy. What are friends for?"
That set off more laughter from the watchers. Javon made Dylan began to frig himself. Even though his mind was in turmoil, the white guy was hard in record time. That triggered more taunts about his lack of size. They made him undo the front of the dress and bare his narrow, now hairless chest, so he could finger his nipples. That got him even more excited and it was obvious that he didn't have enough self control to contain himself much longer. His little dick squirted a line of spunk across the floor, though much less than what any of the others had produced. More pictures were taken as Dylan was made to smile as if he was happy with what had just happened.
At last Javon said, "Now look at that mess you got on our clean floor. That's got to be wiped up. Do you want to do it with that dress? Or with your tongue?"
The thought of getting semen on his tongue made him nauseous. He grabbed the hem of the dress and began dabbing up the string of sperm in front of him, at the same time picking up some of the accumulated filth on what Javon had intentionally misrepresented as the 'clean floor'. When he was done, Dylan looked up at the man who had so easily mastered him.
"I... hope I did everything... right," he choked out. "And I'm glad I was able to cancel out what I did wrong by... doing all this."
"Cancel? What cancel?"
"Well, I mean, didn't this make up for me sort-of-accidently seeing you and Julia while you... made out?"
"No," Javon told him bluntly. "It did not. You still got repayments to make, white bread. So be back here tomorrow at the same sissy time."
"But will tomorrow be the end?"
"Not damn likely. It's like the Bard himself said... 'Tomorrow and tomorrow and tomorrow'. So get another of them old-time-tramp dresses and we'll see what we feel like doing when you get here."
The mental torture Dylan went through after that was nearly unbearable. He was trapped. Reduced to a living sex toy for those four Black overseers. How was he ever going to escape? The dress he had worn was so messed up, especially after using it to wipe the floor, that he had to take it back to his place until he could figure out how he would get it and the others properly cleaned. The next day he stole another and took it to the gym. He stood outside, a nervous wreck, while waiting for eight o'clock to arrive. When it got there he went in unhappily, fearing he would have to give more 'handys', as he had heard them refer to his manual sex efforts.
When he got inside the locker room they had brought four chairs from somewhere. The guys were all sitting in them -- and they were naked, their long relaxed cocks fully on display. Dylan got a bad feeling about his situation. Javon casually told him to undress and get into his new sissy dress. He also wanted his phone and the password to his homepage, as well as his credit cards. Once their boy toy had stripped and then dressed, they made him parade around and kneel in front of each of them, to kiss their feet. It was incredibly upsetting but the most worrisome part was that Dylan kept having sexual stirrings all through his body. Why was that happening? He didn't want any of this to be occurring.
When they made him raise the front of his dress and pin it up, he was crushingly shamed to have them witness his arousal. It set off a diss-storm of insults and nasty remarks about his sexuality. Tyler had him pull up his skirts in the back and show off his smooth bottom. He had to put himself before each guy so they could cop a few feels and talk about how it was just like touching a girl. He even had to sit on the lap of the biggest of them, named Able, who also had the most muscular physique. On Able's lap, facing outward, Dylan had to reach between his own legs to fondle a huge ebony cock. Soon it was standing, thrusting up between the white boy's hairless thighs.
"Day-am," Tyler marveled. "Our Miss Pinky finally got a real cock between her legs. It just ain't color-coordinated with the rest of her."
Dylan had to lightly stroke Able's superior cock and then bring his thighs together so they were holding that impressive piece of man meat between them. Able made him move his thighs to increase the stimulation. After the Black man was highly aroused, he ordered Dylan off his lap.
"Just you get down there on your knees, lily white."
"Y... yes, Sir," Dylan said. Once he was in position he began to run his hands up and down the pole without being told to.
Able said, "That's nice, but rubbing us off was yesterday. Today you start in with sissy sucking."
"I can't do that," Dylan insisted. "I'm not gay."
"Maybe you ain't gay, but you sure are a sissy. Those hand-jobs you gave us sure weren't something a straight guy would do. So don't get all fussy-picky now. You already had your hands on me, now give a few licks and I know you'll figure out the rest real quick."
"Yeah," seconded Tyler. "Sissy knows what to do with a cock like a dog knows what to do with a bone. It's in your blood, pansy."
Dylan ran his tongue up the underside of Able's massive weapon. He capped the knob with his mouth and fastened his lips around it. When he sucked, the seated man made an approving sound. Dylan took in the next few inches but that was his limit. He used his hands on the remainder of it, remembering from that night before that they liked to have their scrotums lightly handled too. Pictures were taken of him giving his first head. OMG, if anyone ever saw those he would be ruined. Now, more than ever, he had to keep these four happy, no matter what it took. Able kept him at it for another ten minutes before launching a load into his mouth. Dylan gagged and thick semen leaked out around his wide-stretched lips. It ran down his chin and he knew another dress was getting filthy.
As he swallowed as much as he could, he felt queasy. The reality of having sperm in his stomach made him feel used. He thought of the terms 'cum dump' and 'jiz jar', as they were applied to cheap girls. He was permitted to take his mouth off Able's cock, but the next guy was already calling to him for similar service. Able got hold of Dylan's hair and kept him where he was for an extra half minute, long enough for the Black man to milk out a final dollop of cream into Dylan's auburn locks. Then the oral slave crawled to the impatient second guy. He had to pleasure him and the one after. His stomach was rebelling from all the cum he swallowed. That left only Javon, who still had Dylan's phone.
The Black man said, "I did you some favors. Took some really flattering shots of you with cocks in your mouth, so now you can look at them whenever you want. Feel free to tug on your mini-dick while you're drooling over them and reliving pleasant memories." He laughed. "And I used your credit card to sign you up for a few web sites. After you get out of here I want you to go to them and check out what you find. It's all stuff a sissy like you will get off on." He looked down at the kneeling student in a dress. When Dylan gave him a meek nod of acceptance, Javon went on, "And now you're going to do me with that pretty mouth. But look here." He took something from the floor next to his chair. "Julia's lipstick. She didn't like this color but I thought it would look terrific on you. Get that cute face up where I can reach it."
Dylan complied and Javon gripped him by one ear, holding it firmly, avoiding the spunk that was everywhere else. He applied lipstick all over Dylan's mouth, not being careful about 'coloring inside the lines'. Javon made a joke about the cosmetic being not only waterproof, but 'cream-proof'. Then he sent Dylan to one of the lockers and told him to open it. There was a mirror on the inside. What Dylan saw made him gasp. His mouth was a mess of bright magenta, looking like a child had scribbled on and around it. Javon summoned him and he got back down on his knees at the locker, then crawled back, figuring that was how he was expected to move. The Black leader had him sit up on his heels so he could write on Dylan's chest. First he circled his nipples with lipstick and then he wrote something. He made the white boy look down and decipher the letters from his upside down viewpoint.
"What's it say?" Javon demanded.
"It says," Dylan answered slowly, full of shame, "pussy mouth."
"Right. Mouth like a pussy for Black cock. Say it, girl. Tell everybody that's what you've got."
"I've got a... pussy mouth... for Black cock."
"Sounds good, especially because you did it all whispery. And remember, snowflake, when you say 'Black cock', you've said a mouthful."
That caused more laughter at Dylan's expense. Then Javon pointed toward his own fat cock. The kneeling young man understood and began to handle it, by then knowing what they wanted and how to achieve it. He coaxed it to full erection and then spent a few minutes adulating it with his mouth without putting it between his colored lips. Next he took the first four inches all at once, hoping the move would surprise and please Javon. It was important not to upset him. Dylan gave a dirty blowjob, purring and lapping and making wet sounds. Javon noted how eager his prey was to do a whorish job. He made Dylan draw it out for a while before allowing himself to firehose a heavy load down the smaller guy's throat.
"Not bad for a first-timer," Javon concluded. "But don't worry. We'll keep letting you practice on us. Every night. And I don't want to call you by your boy name when you're acting so girly. How about we call you... Deena? Yeah, I like that. Deep throat Deena. Or you will be soon. With all that practice. And it looks like you got everybody's jazz on that dress. Better learn to swallow more." He shook his head and chortled. "See you tomorrow, Deena. Parting is such sweet sissy sorrow."
When he got back to his place, Dylan put the dress on top of the previous one. He was so shaken up that he wasn't worrying about getting them in fit condition to return to the stock of costumes. And he would have to find another one for the next night. But he also remembered what Javon had said about using the credit card to buy something that would show up on his computer. Dreading what he might see, Dylan went on-line and sat there in his underwear, trying not to think about how he had to keep his body denuded of hair. It felt so feminine. He unconsciously ran his fingers over his satiny thighs as he checked his inbox.
There, right in the middle of the usual ads and notices and Friend Book posts, were several unfamiliar senders. They were SUBMISSIVE SISSIES, DADDIES AND WIMPS and BETAS IN BONDAGE. As soon as he opened the first one and started looking, he was horrified. Everything he saw involved strong Black mean and weak white guys, the latter group all presented in unmanly ways. The sissies were obviously in thrall to their Black Masters, as the big men were called. The white guys all had tiny dicks and the Black ones were all hung like stallions. The second site was more of the same, except that now, instead of just making the sissies pleasure them with their hands and mouths, they were making them lick boots, kiss jock straps, and nuzzle backsides. The last was even more extreme, with the white victims tied up, strapped down, or in very restrictive bondage outfits -- and being used by the powerful Black men as sexual playthings, even to the point of backdoor penetration.
In a near stupor, Dylan gazed at the images. He touched his smooth chest and belly and groin. His hand encountered his penis and he was unsettled to find it at full attention. His fingers closed around it and in his mesmerized state he gave himself a slow motion stroking. He really needed to finish. Just to relieve all the stress he was under. But he didn't want to. Not while looking at guys like himself worshipping the bodies of Black men like Javon and his buddies. He forced himself to leave the computer, though he didn't turn it off. For comfort, Dylan turned to those beloved dresses. He found one that wasn't as badly spotted with his spunk as the others and carried it to his bed. He lay there, curled into a fetal position, hugging it tightly.
Dylan was feeling more in control of circumstances until his eyes drifted to the computer screen. There was a picture of a small white guy kneeling alongside a muscular Black man, hugging his sinewy thigh, his lips pressed against the dark skin of a hip. Dylan groped under the dress and found his little pecker, which was still stiff. He wished it would just go limp, and that his urges would fade away. But that wasn't happening. The on-screen picture changed to something more explicit. He began to pump his hand, which the Black guys had called his hand-pussy. They had remarked on how soft it was and he couldn't deny it. He wanted to close his eyes and think about Julia. She might be unobtainable but he could still dream about her. Instead he continued staring at the compelling images on the computer. Now it was a sissy with his face wedged between the buttocks of a muscular stallion. It had been so wicked of Javon to spend Dylan's money to buy him interracial sissy porn. Still, that was already done and it wasn't worth the risk of upsetting Javon by trying to cancel it. Dylan attempted to call up Julia's face in his mind but instead saw himself in the place of the kneeling figure on the computer and Javon as the standing one.
"Please, no," he murmured. "That's not what I want. I only want J... Jul... J... Ja... Java..." He sobbed loudly. "I don't know what I want." And with that he shot his meager load all over the dress, the one that had until then been the cleanest of his growing collection.
For the next week his nightly visits to the old gym's locker room involved giving hand jobs and improving his throating skills, along with plenty of lipstick that always got smeared. He defiled one dress after another. And then he got an additional unwelcome shock. When he arrived one evening, still trying to puzzle out how to reverse his ongoing emasculation, he found a mattress on the floor.
Javon told him without preamble, "Time to pop your cherry, Deena. Turn the rear exit into an entrance. But don't worry, we got plenty of lube." He laughed unpleasantly. "So get all naked like usual, and into that dress you got hidden in the plastic bag like always. I hope it's a good dress for this special occasion."
Without thinking, Dylan said, "The dress has a corset waist. It will make me look more like a girl. It's kind of uncomfortable but..."
What was he telling them? How would that sound to the rapacious slave-makers? Especially with him using such a feminine voice. He silenced himself while he stripped in front of them and got into the dress that was tight in the middle and billowed out below. They made him circle the mattress and then stand on it and do a slow twirl. There was enough padding sewn into the breast cups to give him the illusion of a modest bust. The room was still as he waited to find out what happened next. Javon came to him and pointed at the mattress. Dylan got into the familiar kneeling posture.
His Black Master, like one of those in the videos, told him, "Get that chin down and your cute ass up."
When that was done, Javon threw the skirt up in the back. The corset waist enhanced Dylan's figure but it was also squeezed him. The Black man got on his knees behind his target and Tyler tossed him a big bottle of lube. Javon caught it easily in his large hand. He rubbed his cock against Dylan's waiting ass to get himself hard. Then he lubed up. The thick business end of his member pressed against Dylan's pucker. The trembling white guy couldn't believe this was happening. It was too much. He might never recover his male identity if he was violated. Javon leaned into him and his knob was forced past Dylan's tightness. The recipient grunted and let out a long moan. Javon gave him time to get used to being stretched.
The Black penetrator said, "I don't do this to Julia. She don't want to be all stuffed back there with my Black jungle snake. Don't want to be all sore the next day. And definitely don't want to take a chance of getting hooked on it. You want to get hooked on it, Deena?"
"N... no," he mewled. "No, Sir."
Javon got a hand between them and groped for Dylan's genitals. He felt them and wanted to know, "If you don't want your ass plugged with big Black cocks, then how come you're puny dick's all hard again?"
"I... don't know," Dylan wailed miserably. "Please, don't make me want this." He sobbed. "Don't get me hooked on it."
"Ain't me making you want it, girl. It's Deena making Dylan want what I got."
As if to drive home his point, he buried another two inches into his captive. Then he invaded him further and further, until he was in up to his weighty balls. As Dylan whimpered, Javon began an evenly paced in-out motion. He took long strokes to make sure Dylan knew he was being well and completely used. Javon's fingers dug into the softness of Dylan's hips. The bigger man rode him steadily for over a half hour, wearing down the last of his resistance. He invited Dylan to push back against him, saying it would make everything easier. Either because he thought it would ease his suffering, or maybe because he was responding to being used that way, the white guy did begin to meet Javon's thrusts with his own backward shoves. That was what it took to drive the Black stud to an orgasm. He gripped Dylan even harder and, with three short hard jabs, was creaming inside him.
Having cum in his mouth and stomach was bad but this was so much worse. He had been taken in the most sissy-like way possible. And his betraying penis was still hard. Javon hunched over him, descending from the heights of his climax. He withdrew slowly, a long strong of glistening spunk attached to his cock even after it was out. He wiped himself off on Dylan's buttocks and got up.
Javon said, "Sloppy seconds for whoever wants them," and Tyler took the spot he had just vacated.
Dylan groaned in expectation of another rampant tool entering him. That was exactly what he got. The final two guys waited, beers in hand, for their turns. By the end there was spunk leaking out of his rear and getting on the mattress. After they were done they made him clean up as much as he could with his dress. He was left sore and beaten, lying on his side.
His Black Master announced, "Not too much longer now, Deena. Maybe another week. Then we'll be done with you. Your debt will be paid."
As stimulated and shaken up as he was, with visions of IR sissy porn dancing in his head, all Dylan could think of was grabbing his own dick and rubbing off a finish. But he didn't want them to see him display a lack of restraint. All he could think about was sex, except that now his thoughts centered on Black men and white sissies. He covered himself and struggled to where his clothes were. Javon didn't like the effort he was seeing. It showed too much spine. It had been a while already since he had drilled that tight virgin tail. Watching the other guys nail Dylan had aroused him. He was capable of another go already. So he grabbed Dylan by his hips and dragged him back to the center of the mattress. He made the white guy take his dark, still unwashed cock and revive it with his hands. Then Javon got where he needed to be and put his battering ram against that overused entrance.
He called out, "Once more into the breach!" and planted himself in it all the way with one mighty effort, making Dylan wail and begin to cry.
After that was over they let him limp away. The promise of more of the same in less than 24 hours was almost unbearable. But Javon had also said there was only a week more of this nightmare. Dylan made a silent oath that he would get through it, if not for himself, then to honor Julia. He muttered her name and Javon didn't miss it.
For the rest of the week they used Dylan any and every way they pleased. He spent his time in class thinking about the night and trying to sort out his mixed up feelings about it all. After his visits to the locker room, he went back to his place and watched more porn, as ordered to by Javon. He was trying as hard as he could not to become, as Javon had said, hooked on everything. Dylan just had to hold on a while longer.
The final evening arrived. Dylan went to the gym with another dress. This one had a much lower neckline. He had to start replacing them before their dwindling numbers were noticed. There were so many lying around at his place. The night before he had slept with three at once. As soon as he was changed into his dress, Javon surprised him.
"We got to celebrate, Deena. How about you have some wine? It'll make you feel better. Get you relaxed."
"Well, you've haven't been very nice to me and..."
Javon held up an interjecting finger and reminded him amiably, "We've just been trying to help you pay your debt, and let you get in touch with your feminine side. You know, sometimes you've got to be cruel to be kind, in the right measure. But no hard feelings. Right?"
Dylan appreciated Javon's consoling tone. He accepted a glass and sipped it. Able wanted his balls lapped right away but Javon told him to wait. Again Dylan was soothed. He drank more wine. Then two of the guys got into a discussion. They were saying that someone could take wine in an enema and it would get them *****. It sounded like it was something they had debated before. They went back and forth until Javon interrupted.
He said, "I got fifty bucks says it's true. And I got a enema set-up in one of the lockers to prove it. I wanted to be ready to take your money."
Tyler said, "You're on." The other guy said the same. "Now let's see some proof. Otherwise just shut up and pay up."
Javon pointed out, "Yo, I ain't got nobody to try it on."
"Then you owe us. Unless maybe Deena there wants to let us try it on her."
"No," Javon told them. "This is her last night and that wasn't part of what we planned." He got out his wallet and cursed. "Damn. I should have waited till I figured who to use."
Dylan, seeing a chance to really clear himself from any carryover trouble, and deciding that the treatment wasn't harmful, said, "It's okay, Javon. Sir. I'll do it."
"You don't have to."
"No. I want to. So you'll understand that... I don't know... that I'm okay."
"Well damn," Javon said, giving Dylan's small hand a hearty shake. "Guess I'm going to earn some easy money now. Maybe I'll split it with my new business partner."
He made Dylan fetch the rubber bag and tube. Able grabbed a half empty bottle of red. Their test subject had to kneel on the edge of the mattress with his bare bottom raised. They quickly got everything ready and Tyler popped the nozzle into his rectum. As the valve was released, Dylan felt liquid rush into his bowels. He got a full feeling and then the valve was shut and the piece in his bottom was separated from the tube, so he could move around. Very soon he felt the effects of the alcohol. His head was spinning. Tyler said something about how Dylan could just be faking drunkenness. Javon considered that.
He said, "Yeah, guess you're right. How about we cancel the bet?"
"Sure. No big deal."
Dylan, now reeling *****, was vaguely disappointed. Weren't he and Javon buddies now? Working together? Maybe going to split the money?
"And I got to step out for a while," the group's leader said. "You guys keep Deena entertained. Show her a good time for her last night. Help her get in touch with her party girl part."
Feeling too ***** to get back up, Dylan watched hazily as one of the others dropped his pants and knelt in front of him. By reflex, Dylan used his mouth to get the proffered cock hard, then began to suck it. He used all the tricks he could remember learning. This was like being in one of those IR sissy videos. And he was the star. He finished the very sloppy BJ, gulping down semen but also getting it on his chin. The wine was sloshing around inside him. When he seemed like he might pass out they helped him up and walked him, between two of them, to the bathroom. Then they positioned him over the toilet and pulled his plug just as he sat. Dylan emptied himself into the bowl and sat there with a lopsided smile on his face. Someone used the lipstick on his mouth, doing an amateurish job but not as intentionally bad as Javon had before. He was taken back to the mattress and put on his knees.
Dylan was aware of two more cocks being offered to him. He handled them, went back and forth between sucking the one on the left and the one on the right, and then finished each in his mouth, letting cream mixed with saliva run freely over of his lower lip and down his front. He saw how badly the dress was getting streaked with it and laughed. The room was spinning. Someone gave him a pill that they said would help him sober up and a swig of wine to wash it down. They left him the bottle. He laid back, clutching the bottle to his chest, dimly aware that wine was running out onto the dress. He was dimly aware of the lipstick being tucked into the top of his dress.
Then, for some reason, they were putting something around him on the mattress. Pieces of paper? Pictures? His head felt funny. Maybe a side effect from that sobriety pill. He wondered when it was going to start working. And then he passed out.
Meanwhile, Javon had showed up at the rehearsal space shorty after leaving the gym. Julia had asked that everyone involved with the show gather there. She had noticed that the dress she was supposed to wear for the impending performance was gone. When she searched for it she found that many others were also missing. Everyone showed up to discuss the situation. Everyone except Dylan. Professor Smyth was concerned.
Javon defended the missing student. "I mean, why would he do anything with the dresses? They were his responsibility." He made a show of thinking for a few seconds. "On the other hand, why didn't he notice that a bunch were missing? And report it?"
That was all it took to set the others off. They had all noticed how oddly Dylan had been acting for weeks. Like he had something to hide. The girls were especially suspicious. As they discussed it now, Javon still occasionally tried to defend him but opinions were solidifying against the only missing person involved. Javon joined them, but with a show of reluctance.
He said, "Now that I think of it, I have noticed his car at the old gym a few times recently. I figured he was working out. You know, because he's so slender and kind of a weakling."
Julia said, "Maybe we should go over there and take a look."
The Professor backed her up with, "Whatever's going on, I'd like to get this straightened out before opening night."
"Well," Javon said optimistically, "it'll be worth it if we can clear the kid's name."
They all piled into cars and drove across campus. When they got there, Dylan's car was the only one on that lot and the side entrance of the building was open. The group entered and someone saw light coming from under the locker room door. They went there and when the door was flung open and they went in, they were stunned by what they found. There was a mattress on the floor and on it was Dylan, in a dress, his lower body *******. He had one hand on his tiny flaccid penis and the other reaching for a bottle of wine. Spread around him were print-outs from a computer. As people began to pick them up they gasped at what they saw. In every picture Dylan was involved in some sort of lewd sex act, while in a dress, and often looking quite happy about it all. Then they realized that he had semen on his lipstick-colored mouth and his lower face. It was also on the front of the dress, which was stained with wine.
"That's my dress for the show!" Julia lamented. "And there's my missing lipstick sticking out of the neckline."
"This is scandalous," Professor Smyth cried. "I don't want anybody talking about it outside this room."
"It could make the college look terrible," said someone from the rear, someone who sounded like Javon. "It should be handled quickly and decisively. By the college authorities."
A moment later Dylan sat up, blinking his bleary eyes. He said in a slurred voice, "We had a party. I'm a party girl. My name is Deena. Don't call me Dylan."
"Young man," Professor Smyth said, sounding uncharacteristically stern, "you are in serious trouble."
"Wh... what?" Dylan got shakily to his feet and stood there swaying. He was coming to his senses. "It's not my fault," he whined. "It was Javon." He spotted him and pointed. "He was here the whole time. He's the ringleader. There's a whole group of them. I'm not a sissy. I'm not gay."
"What?" It was Julia. "He couldn't have been here. Javon was with us for the last hour." She took his hand. "And I know he could never be involved with anything like this."
Professor Smyth said, "I'm calling campus security. This will not go unpunished."
"And there are still a lot more dresses to be accounted for," Javon added with concern. "You don't think they could be... at his place?"
They went there next and found not only the stained dresses, but Dylan's computer turned on and IR sissy porn running on it. Someone realized it must be a pay site and someone who was a computer science major checked the machine, discovering that he belonged to three pay sites, all with variations of that theme.
The next morning, with the Professor laying out the evidence, and Javon and Julia present as concerned members of the theater group, a hungover Dylan was expelled. He couldn't believe it. At the same time, more demeaning pictures were being leaked anonymously to everyone in the theater group and a number of other students.
As Dylan walked dispiritedly away, a car pulled up alongside him. It was Tyler and Able.
Tyler told him, "I don't think you want to run home to your ******. If you do, somebody might send them a bunch of nasty pictures of you, Deena."
"Yeah," agreed Able. "You need to like get a job and someplace to stay. So I talked my uncle into hiring you. Get in the back of the car."
Feeling like his world was crumbling around him, Dylan numbly obeyed. It turned out that Able's uncle had a janitorial business. They took Dylan there and got him some coveralls. All the ones on the rack were orange except one, which was pink. That was what they gave him.
"Now strip down," Able's uncle told him. He was a hard-faced Black man with a cigar stuck in the corner of his mouth. "You can leave your street clothes here."
Afraid to protest, Dylan got naked. Tyler handed him a rainbow-striped shopping bag. Inside were pink, bikini-cut panties, and a matching garter belt and stockings set. He obediently put them on, having some trouble with the stockings but ultimately donning them. Then the coveralls went on over top. He was given pink running shoes to complete the demeaning outfit.
"Now," Able said, "we'll hold onto the keys for your old place. Help you get moved out. Try not to accidently give all your boy clothes to charity. If we did that, you'd be stuck in the girly stuff we're going to buy with the cash from your wallet, and order with your credit card."
"But... where can I stay?"
"We'll move you into a little apartment my uncle is renting you. Of course, he can't afford to pay you much, since you lack experience in the janitorial field. But you'll be able to make the rent. Barely. Now we'll drive you to your regular assignment."
Still feeling disassociated from himself, Dylan let them drive him again. But why were they taking him back to the campus after his expulsion? As they got him out of the car, passing students gaped at him in that pink jumpsuit and shoes. Some of them had seen the photos of him. Others had heard whispered stories.
"Now just walk yourself across campus to the administration office and report in. I think today they have you cleaning the bathrooms in Alpha Afro Alpha."
"The Black fraternity house? But I can't go in there. If those guys see me like this, I don't know what they might do."
"Yeah. Who knows? And it would be even worse if somebody fired off a bunch of them pictures of you, with Black cocks in your hands and mouth, to them brothers. Pictures with Black cocks but no Black faces. Just your face."
As Dylan started toward the administration building he saw familiar figures strolling toward him. It was Javon and Julia, hand in hand.
She looked at him critically and said, her voice furious, "You are pathetic. I was sickened when I saw you lying there, ***** and covered with semen, your dick hanging out. And that thing between your legs is so small. What is that? Some kind of medical problem? You are a complete freak, Dylan."
Javon told her in a calming tone, sounding not at all urban like he had when he was in the locker room, "I think he told everyone last night that he prefers to be called Deena now. And he can't help it if he has an impossibly small dick, something no girl would ever want. His issues with being sexually different and seeking certain types of partners and abnormal acts, well, that's for him to deal with. Deena may seem like what the Bard would have called a puling whelp, but there's always hope. For now, we can only offer him our pity."
Julia took Javon's arm. "Oh, baby, you are such a good person. I'm so lucky to have you." She gave Dylan a final withering look. "And I'll try to be sympathetic toward creeps like... Deena. But it's not easy. I'd be just as happy if I never had to set eyes on him -- or her -- or whatever -- again."
Javon concluded, "Thus ends our drama." A moment later he gave Dylan a private wink and added, "All's well that ends well."
As they walked away, Dylan began to tremble. His last dream had just been shattered. Julia despised him. Soon he had to face the Black members of Alpha Afro Alpha house. And he couldn't see any way to get out of the trap he was in, especially with those blackmail pictures available to send to friends and ******. Everyone's address had been on his computer. He was doomed.
Even though he had been unceremoniously thrown out of college, he was still going to get a lot more schooling.
*********
(This story is from an outline by Devin Dickie, who also provided the clever title.)
Dylan didn't fit well into most groups of guys. Not only didn't he play sports, but he didn't follow or bet on them. He wasn't interested in cars. And though he had a longing for girls, his record with them was a string of failures. The last problem was especially hurtful to him. He wanted to date someone and couldn't understand his inability to do it. He was short, but so were plenty of girls. And his slender build shouldn't be a deterrent. His modest frame made it easy for him to dress well, with nice designer shirts and straight legged jeans, plus a selection of crewneck sweaters and the like. He took care of his grooming, using gel on his full head of auburn hair, as well as emollients and exfoliating products on his skin. Still, something was lacking.
After he got into college he joined the drama club to try to build a social life. But as shy as he was, they usually relegated him to handling props and costumes. He preferred the latter, because carrying a dress was easier than assembling a set. Besides, Dylan had gotten the idea that bringing dresses to girls would be a good way to get to know them, and that might lead to more. Particularly with one girl -- Julia. He was especially excited when the group decided to present a modernized version of Othello. The actors could improvise and rework their lines if they kept to the Shakespearean feel and the director approved.
Everything was progressing nicely when one of the cast members dropped out. He had been playing Clown and, for some reason, several others thought of Dylan as a replacement. When the young man objected that he hadn't acted on stage yet, they pointed out that the character only had fourteen lines in the original play. Dylan could certainly hold his own with such a small part, especially since he didn't have to remember the lines exactly, but only their essence. He accepted it with a mix of unfamiliar pride and nervous trepidation. He was most motivated to make the effort, however, by the chance to see more of Julia. In his imagination she was his fair maiden, and he her noble gallant. She was the finest actress in the group.
Julia was a willowy blond, her flaxen hair falling to her milky shoulders. Her bust was rather full for the rest of her figure, and showed itself to good advantage in the Elizabethan dresses she wore when performing The Bard. Often she would play opposite Tyler, who was tall and handsome, his reddish-gold hair worn short and neat. He was also on the swimming team. For this play they had a recently transferred student joining them. That was Javon, who shared Tyler's superior height but not his Scandinavian complexion. The new student was Black and excelled at basketball.
So there Dylan was, still handling costumes, but now about to wear one himself. He liked to go to the wardrobe area when no one else was around, just to appreciate the workmanship and design of them. Sometimes he would hold a mutton-sleeved shirt or pair of breeches up in front of himself and admire the effect in one of the full length mirrors backstage. He would perch a jaunty cap, perhaps with a long feather projecting from it, atop his head and strike extravagantly theatrical poses. Once or twice, thinking of how young men had portrayed women before females were permitted to perform on stage, he would even pose with a dress in front of him, marveling at the intricate brocade work and flowing skirts.
Once, he took a dress that Julia had recently worn and hugged it against his narrow chest, inhaling the lingering traces of her perfume. That made his heart beat faster and, even though it was embarrassing to admit it, even to himself, his penis throb. He'd had some problems in that latter area back in high school. In the locker room some of the bigger guys, and most of the guys were bigger, had taunted him about having a small dick. He tried to take it good naturedly, telling himself that it was simply how guys behaved in that environment. He also told himself that he was of average size down there, and that the impression of him being small was because they weren't allowing for his lesser stature, and the fact that his body parts were in proportion with that.
One afternoon, at a rehearsal, he determined to listen more closely to the leads as they spoke their rewritten dialogue, in the hope that it would help him to do better with his own. Julia, as Desdemona, swept out from behind one of the flats. Tyler, in the title role, entered from the opposite side. Javon, who of course portrayed the Moor, waited patiently in the wings. Their director, the gay but not effeminate Professor Smyth, suggested that they simply improvise a scene to warm up.
Tyler went to Julia and proclaimed, "Verily, charmer of my heart, the blossoms of the fields would lower their heads in modest surrender to your beauty."
She looked directly into his eyes and responded, "And the stags of the forest declare themselves less than thou in poise and courage."
Javon swept in and declaimed, "But hark, what darkness from offstage struts?"
Everyone laughed at his intentionally humorous line. He bowed to his fellow players.
Tyler asked, "Good friend, brother of my trust, why is your countenance clouded?"
Now serious, Javon said, "There is a storm aborning and it casts its shadow far. Fair weather is foul and foul fair when men do not speak their minds truly. Even the devil may quote scripture to his purpose. And brothers we may be, good Othello, but are we bonded by barefaced trust or that which but wears the mask of trust, and thus leads us to false fellowship?"
Barely missing a beat, Tyler told him, "What have such as we to fear of truth made its opposite? What silver tongued imp would speak midnight words to us on such a noon-bright day?"
The Black actor spoke with sly persuasiveness when he said, "Who indeed, when friend is foe and foe friend?"
Julia put herself between them, as if it discourage an impending conflict. "Pray, list to me, good men. For good you both are, though perturbing riddles might your minds confuse and sway."
The three of them stood there, with no one sure who should provide the next line. As one they broke up laughing. The director joined them, clapping without moving his hands very far apart.
"Bravo," he congratulated. "That's the sort of thing I want to hear. You have the rhythm and intonations I'm listening for. And I like what I've heard the last week or so, with a soupcon of contemporary English. I hope you've been working together and writing down the lines you come up with."
They all agreed that they'd been doing just that. Professor Smyth suggested that just Julia and Javon work on one particular scene together. Tyler said that if they wanted to talk with him later, they could just call. He left with the professor, but Dylan remained, unseen, lurking in the shadows offstage. The two actors ran some lines, exchanging them impressively. Javon offered a different way for them to stand in relationship to each other.
Julia told him, "You have a terrific sense of stagecraft. I can picture you directing."
He said confidently, "I know someone I'd like to direct."
"Who," she asked coyly. "Me?"
"That's right. In a love scene."
She extended her hand and he took it, bringing it to his lips so he could place a kiss on it. Then he gently pulled her toward him. She allowed it willingly and they embraced. Julia turned up her face and he lowered his, both meeting in a tender kiss. His large hands ran down her back and settled on the top of the rise of her bottom. From his hiding place, Dylan froze up inside. He watched as the recipient of his passionate-but-unvoiced love kissed Javon again, with growing fervor. Dylan backed into the dressing closet where he would be invisible. He was squeezed between two female costumes hanging from the crowded overhead bar. Instead of being discouraged by what he was witnessing, he felt himself become more emotionally involved with Julia. Seeing her taken by someone else made her even more desirable. His already deep crush swelled into obsession.
Dylan watched intently as they alternately kissed and talked. Javon was so confident and relaxed. She was obviously smitten with him. But she was still somewhat shy around his overwhelming masculinity. Dylan could see the conflict in her body language. It was like something you might learn in an acting class. Except that this was real. She finally stepped away from Javon and held up her hands.
"Really," she said breathily. "We've got to slow down. I mean, I don't want this to stop but..."
When she couldn't finish her sentence, the Black student offered, "But it's all happening too fast. Right? No problem, angel. Slow and steady. How about if we get together after tomorrow's rehearsal? Go out for coffee. Or a drink, if you'd like." He took her hand in both his. "It's what we both want."
She brought her hand up to her chest, so that his hands were between her breasts. "Thank you, Javon. It's like you can read my mind. Tomorrow would be fine." She smiled impishly. "Give me a chance to catch my breath."
"And give me time to think about you and how sweet you are."
They kissed once more. Javon looked directly toward where Dylan was cowering. Then the Black stud walked Julia out with his arm around her shoulders, her head leaning against him. Dylan was trembling from unfamiliar feelings. It was somehow exciting to see her with that superior male. And to witness how she melted under his subtle approach. Still between those two dresses, he held the sleeve of one against his cheek as his other hand drifted downward. Almost without knowing he was doing it, he put his fingers against his crotch and moved them up and down, ever so slowly. The paired sensations of that sleeve and his self-stimulation worked so well together.
His thoughts went back to how young guys had historically played female parts. It was a perfectly normal occurrence. And it would be a good acting exercise for him to try it. He stepped out of that confined space, reached back, and took the dress he had been fondling. It was gorgeous, with short ruffles at the cuffs, a high neck, buttons down the front, a corset waist, and billowing, ankle-length skirts. There were even breast forms sewn into it. Maybe it actually had been worn by a guy before.
In a trance, images of Julia and Javon still dominating his mind, he unzipped the back and set it aside. It would be awkward and uncomfortable to still have his own clothes on under it. Dylan began unbuttoning his shirt. He was impressed that his erection was still 100%. His fingers massaged it lightly for a minute. He reached into his half opened shirt and felt his nipples, which added to his arousal and mesmerized state. Soon he was naked, taking deep but calm breaths as he stepped into the dress, got his arms into the sleeves, and reached around to zip himself into it. The raised neck fit close against his throat and the insides of those breast pads rubbed against his chest intimately.
A new thought flashed into his consciousness. What if Julia had worn this very dress? Did he dare to believe that? Dylan wanted to pay tribute to her, to express his affection, even though she wasn't there. He could be Julia, if only for a short time. He could aspire to that ideal, though it was plainly unobtainable. Dylan took a step, and then another. He raised one arm and made a broad gesture that could be seen from the back rows. His steps were small and feminine. A wiggle became apparent in his walk. He tilted up his small chin and licked his lips. He was dedicating his mini-performance to the girl with who he was so taken.
Dylan sashayed back to the wardrobe and picked a small round hat. It had fake gemstones set around its sides and a short veil in front. He smoothed the netting over his upper face and puckered up his lips to make them more girlish. When he got in front of one of the dressing mirrors he was stunned by the effect. Though he had never worn anything feminine like this before, it seemed very familiar and, more importantly, right. At the same time, another part of his brain was telling him that it was wrong and shameful. Yet how could anything that felt so good be bad? He decided to get back into his street clothes and give himself time to sort everything out.
When he was naked again, he couldn't resist embracing the dress, as if it was a fusion of the girl he longed for and his own idealized version of himself as her. It was all so confusing. Holding the dress against him, he dared to grip his small erection through the layers of material and stroke it until he moaned. No, he had to stop. Was he gay or something, reacting this way to crossdressing himself? And what about being turned on by peeping at Julia and Javon's physical contact? Why had that been so stimulating and unforgettable? Yes, he definitely had to get away from here and restore a sense of normalcy. After all, he always had the option to return and try dressing up again. Just to see how it effected him. He assured himself that he could stop anytime he pleased.
The next day after classes there was one more work session on the play. Another play was going to precede theirs. The sets for that one had been finished during the afternoon. There was a modern looking bedroom interior, and a bed in the middle of the floor. Dylan again watched from the sidelines. He then got to run his lines, which he was having trouble with even though there were so few of them. His part involved confronting a musician who was playing too loudly and annoying the master of Dylan's character. The other actor had been toying with the lines and called Dylan, as the servant Clown, onto the stage. The guy, portly and swaggering, took his place. Dylan uneasily put himself in front of him.
The guy said, "Just follow my lead." He took a moment to fuss with the collar of his shirt, as if he was in costume and was using some acting technique. Suddenly he looked Dylan in the eye and said, "What, good sir? Why do you interrupt our music?"
"It's..." Dylan was aware of the three principals watching him, especially Julia. "It is too much... or too loud, for my Master."
"Do you not appreciate it yourself? Are you a music maker?"
"I... I am not?"
"And yet, but a moment ago, I clearly heard you sound an unfragrant note. What inspired such an effort?"
"I... played no music... Sir."
"You played an air that an ass might play after it eats too many apples. The ass plays his special instrument, whereby hangs a tale."
"I... played that pleasant note... because it was in my heart," he improvised, trying to keep up.
"It would seem sure, minstrel of repasts past, that it issued from a lower region."
That line was met with laughter and spontaneous applause. Dylan was lost and clueless. Javon came out and clapped him hard on the back. Julia wagged her finger teasingly at the uncomprehending performer. Tyler went and congratulated the student playing a musician. Professor Smyth said they would keep the lines in, and that he thought Dylan was very convincing as a fool. The next hour went well and then everyone was ready to leave.
Julia and Javon were making plenty of eye contact with each other. Dylan faded into the background, hoping for a replay of their previous behavior. He was denied that, however, as they limited themselves to a few chaste kisses. But there was a change as Julia pressed her pelvis against Javon's and held it there, her generous bust partly flattened as she hugged him tightly. When she stepped away there was an unmistakable bulge between his legs and running partway down one thigh. It was huge. Dylan couldn't keep from comparing himself to what he was seeing. It contradicted the smaller student's belief that his own penis was average size. But then he told himself that he was still of normal dimensions, and the Black guy was well above the middle range.
Julia reached out hesitantly and ran her fingertips along that impressive length. She pressed her body against his again, this time moving her hips as she did so. Her eyes strayed to the bed in the corner of the stage. She licked her lips nervously. But then Javon moved back and the moment passed.
He told her, "I know someplace more comfortable and private. If you don't mind a short wait."
She said breathily, "All right, Javon. It's just that I've never been around someone quite like you."
"Yeah," he told her without modesty. "I get it. And you'll get it later, girl. Right now let's take a drive and talk, let you make sure you're thinking clear."
Was he being a gentleman? Dylan wondered. Or just enjoying how obviously eager she was? Either way, they left together, Julia with both hands on his upper arm, feeling his muscular bicep. Dylan had to sit down after they were gone. He felt as out of breath as she had been. It was like he had an emotional link to Julia. When he reached behind him, his hand brushed the hem of one of the dresses hanging there. He caressed it softly, pulled it forward, and kissed it tenderly. He pictured beautiful Julia wearing it as he did that. Like after the last rehearsal, Dylan's pecker got stiff. There was no pause for rationalizing this time as he rapidly stripped and got into the dress. Dylan did a reprise of his pantomime, mincing around, adding some more arm movements, and posing in front of the mirror.
Then came a moment of decision. He wanted to touch himself as he had done the other time, but he also wanted to go further. To go all the way, if that term could be applied to a lovelorn young man with only his hand to comfort him. He turned away from his reflection, hoisted up the heavy skirts of the dress, and got a grip on his dick. It was electrifying. He began to stroke himself, at first rapidly, but then at a more measured tempo, not wanting to rush through to the end. He kept it up for several minutes before daring to slowly turn back and face his image in the glass. It was so strange to see himself covered up in that lovely dress from neck to where he was holding it up. Dylan's face, so smooth and with such fine features, didn't announce his maleness. He saw how androgynous he could appear, and that amplified the effect of being in that dress, the one that Julia might have worn.
As his confidence rose, he began striking poses like he had done yesterday. Then he broke away to hook the dress up in front, using large safety pins. Now he could have his hands free. That allowed him to finger-comb his hair, run his hands down his sides, and raise the dress in back so he could turn around and look over his shoulder at the reflection of his shapely buttocks. He stuck his tongue out at himself and giggled at the sight. Facing his reflection once more, Dylan resumed masturbating. He moved away, got a second dress, and went to the bed. When he laid back on the mattress, it was as if he was in another world. He spread the second dress on top of himself, so that he felt completely enclosed by the feminine garments. His hand kept pumping. He shoved the fingers of his other hand into his mouth and closed his jaws. Moaning loudly into the improvised gag, he climbed toward a climax. Before he could consider the consequences, his little dick spurted. His orgasm made him arch his back for a moment before he collapsed back into an exhausted daze, ******* of his surroundings.
Dylan pushed the heavy dress covering him to the side and it dropped to the floor. With the one he was wearing still pinned up, he remained in that state for almost a quarter of an hour. His mini-adventure into fantasy had been so erotic that he was still feeling aroused. He played with his spent penis, using his own spunk as lube. Undoing the front of the dress, he spread the halves of the bodice and used his other hand to play with his receptive nipples. His member didn't get hard again but it was so nice just to be handling it. He writhed his hips, eyes closed and mouth opened. That went on for a timeless time, until he slowly came back to reality.
That was when he got the second dress off the floor and saw that he had shot his mess all over it. What if someone spotted that? And they somehow realized it was him who did it? After all, he was getting known as the 'costume guy'. Dylan sat on the edge of the bed with his head hung. The idea of having his secret practices ******* was heart-stopping. Then he had an inspiration. He was the only one there. No one would know if he -- did he dare? -- if he took it home with him. Naturally, he would only be doing that so he could clean the garment. That was all. And maybe try it on again. Once. Or twice. So he smuggled it out of the building and put it lovingly into the trunk of his car.
As soon as he got home he snuck it into his room and spread it out on his bed. The stains he had made were mostly dried. He folded the dress so that they were covered. Then he got completely undressed and lay on top of it. The contact of all that smooth material against his soft body was wonderful. He lay there relishing the sensations that were running through him. And there was no rush to get the dress back. If he rearranged a few of the others, no one would notice its absence. And if they needed that specific one he could -- well -- think of something. Maybe say that he had moved a few to the backup storage area. Sure. That would cover him.
The new production had started its run, but the theater was empty after each performance. Over the next week and a half, he enjoyed several more episodes of playing dress-up on the vacant stage and playing with himself at the same time. The more times he got spots on the dresses, the less important each one seemed. And he was slipping them out of there to smuggle home, so no one need ever know. Dylan was in deepening denial but he didn't see it that way. He was simply... experimenting. One of the interesting discoveries he made was that he didn't want to masturbate with the dresses at his place. He loved wearing them there, and it got his little prick standing up every time. But jerking off was only a thrill when he was alone on the stage. Maybe it was because that was where Julia was so often. Or it was just the knowledge that he was doing something very forbidden, and even risky. Whatever the explanation, he couldn't stop what he was doing and, more importantly, where he was doing it.
Dylan went to that deep storage area just to see what else might be there. He was delighted by what turned up. There were several dresses that were somehow extra racy. They were still period ones, with full skirts and fancy detailing, long sleeves and high necks. But they were tailored differently and hugged his body in ways the others hadn't. When he looked in the mirror now he saw not a demure woman of the past who might sometimes become sexually abandoned. Instead he saw a lascivious girl who craved male attention and was ready to reciprocate. He was in one of those, on the bed, the skirt bunched up around his waist, happily pulling his small penis, when everything changed.
From the dark he heard a male voice say, "Busted!"
Another called out, "And surrounded."
As Dylan lay there, trying unsuccessfully to push the skirt back down over his naked lower body, several figures emerged from the shadows. The first was Javon, neatly dressed as if for a date. The other three, also Black, looked more thuggish. They penned him in on the bed and one reached out to grab the hem of the skirt and pull it up even higher than it had been. Several phones appeared in dark hands and pictures were taken.
Javon said, "Look at what we got here, men. The white fairy princess all dressed up for the ball. Looking for her prince. Preferably one with a super-size cock."
"She-it," said one of the Black guys. "Maybe we ought to enroll in this place."
"What?" Dylan reached for the hem of his dress again but an angry glance from the guy who had pulled it up stopped him. "I'm not a fairy. I was just... uh... method acting. Getting into a role."
"Whoa," Javon interrupted. "You're playing Clown, the easiest part in Othello. And he sure ain't no pansy cross dresser. Plus, unless I'm forgetting my Shakespeare, there's no scene where he jacks his Jones. Right?"
"Well, yes. I was thinking more of how boys used to play girls in the old days."
"Right. I know my Shakespeare 101. I know that they used to have the stage direction, 'ENTER: Dressed As Girl'. And I know that got shortened to 'drag'. As in, I still don't know what you're doing there in drag, pulling your miniature pud. The only answer I can figure out is that you are a stone faggot wimp sissy. Am I right or am I right?"
"Not... the way you mean it... I just like to... dress this way. But I only started doing it recently."
More pictures were taken. Javon snapped at him to get up. "And don't give me anymore sorry excuses. From here on in, you just do what me and my crew tell you. Otherwise, the shots they been taking are going to go viral. Understood?"
"Go...? You would...? But then I'd be..." It all sank in and Dylan stood there in the dress that was so sexy in a historical way. "Yes, Sir."
"That's more like it. Now you're skirt fell down and I didn't say that was okay." He looked at the other three young Black men. "Did any of you dogs say it was okay? No?" His attention returned to Dylan. "So let's get it back up where it was, candy ass."
Dylan unenthusiastically gathered up the skirt in front, revealing his penis, which was now limp from all the upset. He stood there with his thighs pressed together in a failed attempt at modesty.
Javon went on, "So here's what you're going to do. First, you're almost hairless down there. But I don't want to see that peach fuzz growing above your baby size dick. So tonight you make sure to get rid of it. Buy yourself one of those handy razors like the girls all use. And some girl style shaving cream. And while you're shaving down there, get rid of anymore you have anywhere else. I want you clean and pink all over, like a bitch."
As if to reinforce Javon's words, one of his backups stepped in, fists balled at his sides, and gave Dylan an angry scowl. "Yo. Tell the man you going to do what he says."
"Yes, Sir. Yes, Javon. I'll do that. Tonight. Like you said." His voice was quivering. He wished they would allow him to cover himself.
"And then," Javon continued, "you going to meet up with us, tomorrow night at eight. We'll all get together in the old gym. Now that the new one's done being built, they leave the other locked up. But I got myself a key. So you report for sissy duty and we'll be there to help you get into the new part you'll be playing. Damn, you said you was method acting. Well, you going to get into the method real deep, and with us four to be your acting coaches. Going to help you get into the roll of sissy who don't want to have them pictures sent to the campus cops, and administration, and even Professor Smyth, who might like them, if you know what I mean."
"I... all right," Dylan conceded in defeat. "The old gym tomorrow at eight."
One of the other guys said, "How about if he bring a dress. A real old-time slutty one like he got now."
"I shouldn't," Dylan objected. "I already have too many at my place and..." He ran out of words. Clearly, they didn't care.
Javon made a mental note of that unintended revelation. He said, "Just be there, girly girl. With the dress. Now how about a few more poses for me and my posse? Like get on your knees with -- " He went to a table and picked up a plastic bottle of hair gel. " -- with this in your hand. First up, hold it alongside that shrunk up dick, so everybody can see how small it really is. Then get yourself hard again. It'll be fun for us to watch you do that. And do the size comparison a second time. You still won't come out looking too good. Then, for the big finish, give that bottle some licking, and get your sissy lips around the top of it, like its a cock you be sucking off. Me and my buddy's will make sure there're plenty of pictures, just in case you need more persuasion later."
Dylan followed those mortifying directions, while the quartet or Black tormentors laughed and took many more pictures. They even sent some of them to friends, just for fun, which proved to their victim how ready they were to ****** him more widely. They taunted him too, about how gay he acted, how small his dick was, and how he was lucky he wasn't into girls, because no female would be interested in him with the bad news he had between his legs.
At last, with the foursome satisfied and Dylan feeling exhausted, on the verge of a mini-breakdown, Javon's three friends left. The student in the dress looked at his fellow actor.
"But," Dylan wanted to know, "how did you find out what I was doing in here?"
"Well, stupid, you screwed up and did the humpty dance with your hand in one of the dresses Julia plans to wear for the real performances. And then you didn't take care of them pecker tracks. It freaked her to find your little sissy shots on her dress. She knew something was up. Then she told me because, you know, I'm her boyfriend. And we figured you were doing it right here, and you'd seen me and Julia getting to know each other. You did spy on us -- right?" After Dylan confessed, Javon went on, "Then I decided to catch you at your nasty game. So I came in, real quite-like, and saw what you was doing. From there it was easy to get my boys and set up this -- let's call it -- sissy intervention. Now we're going to help you get in touch with your real self. The queer inside."
"But, I'm not that way. Honestly."
"Maybe not. I've seen you getting all dreamy when you look at Julia. But I think your sissy side is the boss of you. It's like some of that truth they teach us in psychology class. Hey, maybe I can get a term paper out of this."
"Please, no," Dylan pleaded.
"That was me funning you. But the other part is deadly serious. Tomorrow night. Eight. You know where. See you then, sweet cheeks."
After that Dylan had a restless night. All the next day in classes his mind was elsewhere. After classes he had time to kill. As he wandered around campus, he kept thinking that people were looking at him with knowledge of his secrets. At 7:30 he went to get a dress from the theater. He held it against him and tried to think positive thoughts about Julia. But she was the one who had outed him. And Javon might have told her what they'd discovered. Maybe even shown her some of those incriminating photos. He was devastated. Well, he told himself, he had to get this over with. Dylan decided that, if he endured more of their torment, and tried to act like the situation wasn't overly serious, they would just lose interest in upsetting him and that would be the end of it. Sure. It wasn't like they were going to do more than make fun of him and have their cruel entertainment. Was it?
He got to the darkened old gym precisely at eight, figuring that tardiness was a bad idea. The door was unlocked and there was a light on in the locker room. He had bad memories of locker rooms past, where classmates had seen and mocked his supposedly undersized endowment. He went to where light was showing under the door and, not sure how to approach them, knocked respectfully.
There was laughter from inside and Javon's voice told him, "Come on in, missy."
Dylan entered the locker room and found all four of them waiting. One of them, who he had heard Javon call Tyler, told him to get naked. With their eyes on him, the sole white person in the room had to strip down. He stood there shifting his feet until Tyler barked at him to stay still. The threatening Black figure came close to him and put his hand on Dylan's bare shoulder with easy familiarity.
He said, "Hey, boy, you got to trust us. All we're doing her is settling a score. You spied on our main man and his woman. You know who I mean. That blond girl who loves spreading her legs for his big... black... pussy-splitter. So we have to do what we have to do." His hand slid down Dylan's back and caressed his bottom. "Then, since you look like a white girl yourself, it just makes sense for us to treat you like one. And for you to play along. Get into the part. You know, cause your an actor and all. Or actress." He laughed at his own humor. The others joined in. "But we don't want to make it too rough on you." He moved his hand to Dylan's wrist and gripped it tighter than the student would have preferred. Tyler rubbed his thumb over Dylan's palm and said, "Now one thing you got that's real girly is how soft you are. This hand is damn soft. Feels like a pussy almost. And a pussy feels good on a cock. So how about you put on that slutty dress, get down on your knees, take my rod out of my pants, and give me some hand pussy. You want to do that for me? Just to help make things right?" When Dylan was too scared to speak, Tyler added, "Or would you rather do something else girly for me, instead?"
"No, Sir. I mean, yes, Sir. I'll do that with my hand. Just please, not the other thing."
The barely veiled threat set Dylan into action. He got the dress and, with all of them still eyeing him and snickering, put it on. Having Tyler call it slutty made him understand that, just as he'd seen it that way before, others could perceive it the same way. Dylan suddenly felt like a courtesan or, perhaps more accurately, a fallen woman. Once he was dressed he sank to his knees in front of the waiting Black guy. His unsteady hands came up and he began to undo Tyler's pants. Less than a minute later, despite clumsiness born of fear, he had Tyler's cock freed and in his hand. It was alarmingly big, like Javon's. As soon as Dylan began to gently knead it, the length began to grow. It quickly went from six inches soft to eight hard.
"That's my little snowflake," Tyler encouraged. "You take care of me and I won't have to do nothing bad to you. Show me you want to be a good sissy. Let the other brothers know that you're the kind that satisfies."
Dylan got his second hand into the action, using it to hold and manipulate the knob while he continued to stroke the thick shaft. Tyler hummed a few tuneless bars under his breath. He told Dylan to take his time and that they had all night if they needed it. The kneeling young man sniffled and bit his lips. His new rationalization was that they just wanted to prove how much they could control him. It was something they needed, to feed their egos. Fine. He would submit to this and it would let them feel victorious. After that he could put all these indignities behind him. He kept working on the heavy organ, his fingers stretched around it, the contrast between his pale skin and the darker shades of Tyler's body so vivid.
"There you go," Tyler said between deep breaths. "You got me right on the edge, girl. Now take me the rest of the way."
The way Dylan was positioned, if Tyler shot now, it was going to get all over Dylan's face and the front of the dress. He started trying to lean to the side but Javon saw what he was doing and understood why.
"Hey, sissy," Javon told him. "Watch your posture. Get that back straight. You don't want that sexy dress to get all scrunched up."
When Dylan did as he was told, it put him back in the line of fire. Tyler grunted and his cock spurted. A gob of white cream caught Dylan in the cheek. The next one struck him in the chin. And the third landed on the formerly clean bodice of his dress. Tyler took half a minute to relax after his burst of pleasure. He seized Dylan's arm and brought it up so he could wipe the end of his cock on the sleeve. He took some pictures of Dylan's messy face and reminded the others to get shots.
Tyler said, "Next", and another of Javon's off-campus friends stepped in.
This one told Dylan he wanted his balls massaged and that, if he did it too hard, he would get his own balls treated in ways he wouldn't enjoy. The sufferer's knees were getting sore. He wanted to wipe off his face but was afraid of angering his captors. Besides, he didn't want to use his sleeve and get the dress even dirtier. The standing figure took several pictures while he was being stroked. This time was a lot like before and a load was fired against Dylan's closed mouth, chest, and into his lap. It went on like that. The third guy wanted his cock talked to, for Dylan to use a lisping voice to tell the long member how much he loved fondling it. That ended with the cock's owner groaning something about busting a nut and then suiting his actions to the words. Dylan was beginning to feel like he was going to be soaked through. In fact, he could feel dampness seeping through the fabric in a few spots.
The only Black man left unserved was Javon. But he wouldn't want to be hand-pumped because he was dating Julia. Having sex with Dylan's dream girl. And from all evidence, emptying his balls frequently with her willing participation. Yet Dylan's initial assumption was wrong. Javon did want his impressive meat manipulated. He chuckled as Dylan got it out of his pants and began stroking it, leading to an engorgement that made it the largest one yet. With his thumbs on its sensitive underside and his fingertips on its top, Dylan performed unhurried, two-handed maneuvers. Javon grinned down at him, as if he was gloating at both the white guy's helplessness and the fact that Javon had taken the object of his longing away from him. As clear fluid appeared at the tip of Javon's penis, Dylan began to quietly sob.
The big man kept him at it for nearly a half hour, while the others drank beer and ate pretzels. They even handed their leader a can that he took occasional swigs from, as Dylan submissively tended to his rampant organ. At last signs appeared that Javon was about to relinquish control to his urges. Dylan dreaded having his features spattered with semen one more time. He subtly tried to angle that massive tool lower so its output would all land on the already messy dress. But Javon saw what he was doing and ordered him to aim it straight at his own face. Javon felt hot tears rolling down his warm cheeks. He gave three more pumps and the well-primed prick fired point blank at his eyes, nose and mouth. He got the full amount on his writhing face. There was so much that it ran down and dripped from his chin. His nose began to run. He blinked cream out of his right eye.
Javon laughed. "I seen you take care of your skin with that crap you sneak onto it during rehearsals. Some expensive girl-type product. Well, now you got a full facial, and it didn't cost you a thing. How about you thank me for that."
"I... yes, Sir. Thank you, Javon. Thank you for my... free facial."
"Hey, no problem, buddy. What are friends for?"
That set off more laughter from the watchers. Javon made Dylan began to frig himself. Even though his mind was in turmoil, the white guy was hard in record time. That triggered more taunts about his lack of size. They made him undo the front of the dress and bare his narrow, now hairless chest, so he could finger his nipples. That got him even more excited and it was obvious that he didn't have enough self control to contain himself much longer. His little dick squirted a line of spunk across the floor, though much less than what any of the others had produced. More pictures were taken as Dylan was made to smile as if he was happy with what had just happened.
At last Javon said, "Now look at that mess you got on our clean floor. That's got to be wiped up. Do you want to do it with that dress? Or with your tongue?"
The thought of getting semen on his tongue made him nauseous. He grabbed the hem of the dress and began dabbing up the string of sperm in front of him, at the same time picking up some of the accumulated filth on what Javon had intentionally misrepresented as the 'clean floor'. When he was done, Dylan looked up at the man who had so easily mastered him.
"I... hope I did everything... right," he choked out. "And I'm glad I was able to cancel out what I did wrong by... doing all this."
"Cancel? What cancel?"
"Well, I mean, didn't this make up for me sort-of-accidently seeing you and Julia while you... made out?"
"No," Javon told him bluntly. "It did not. You still got repayments to make, white bread. So be back here tomorrow at the same sissy time."
"But will tomorrow be the end?"
"Not damn likely. It's like the Bard himself said... 'Tomorrow and tomorrow and tomorrow'. So get another of them old-time-tramp dresses and we'll see what we feel like doing when you get here."
The mental torture Dylan went through after that was nearly unbearable. He was trapped. Reduced to a living sex toy for those four Black overseers. How was he ever going to escape? The dress he had worn was so messed up, especially after using it to wipe the floor, that he had to take it back to his place until he could figure out how he would get it and the others properly cleaned. The next day he stole another and took it to the gym. He stood outside, a nervous wreck, while waiting for eight o'clock to arrive. When it got there he went in unhappily, fearing he would have to give more 'handys', as he had heard them refer to his manual sex efforts.
When he got inside the locker room they had brought four chairs from somewhere. The guys were all sitting in them -- and they were naked, their long relaxed cocks fully on display. Dylan got a bad feeling about his situation. Javon casually told him to undress and get into his new sissy dress. He also wanted his phone and the password to his homepage, as well as his credit cards. Once their boy toy had stripped and then dressed, they made him parade around and kneel in front of each of them, to kiss their feet. It was incredibly upsetting but the most worrisome part was that Dylan kept having sexual stirrings all through his body. Why was that happening? He didn't want any of this to be occurring.
When they made him raise the front of his dress and pin it up, he was crushingly shamed to have them witness his arousal. It set off a diss-storm of insults and nasty remarks about his sexuality. Tyler had him pull up his skirts in the back and show off his smooth bottom. He had to put himself before each guy so they could cop a few feels and talk about how it was just like touching a girl. He even had to sit on the lap of the biggest of them, named Able, who also had the most muscular physique. On Able's lap, facing outward, Dylan had to reach between his own legs to fondle a huge ebony cock. Soon it was standing, thrusting up between the white boy's hairless thighs.
"Day-am," Tyler marveled. "Our Miss Pinky finally got a real cock between her legs. It just ain't color-coordinated with the rest of her."
Dylan had to lightly stroke Able's superior cock and then bring his thighs together so they were holding that impressive piece of man meat between them. Able made him move his thighs to increase the stimulation. After the Black man was highly aroused, he ordered Dylan off his lap.
"Just you get down there on your knees, lily white."
"Y... yes, Sir," Dylan said. Once he was in position he began to run his hands up and down the pole without being told to.
Able said, "That's nice, but rubbing us off was yesterday. Today you start in with sissy sucking."
"I can't do that," Dylan insisted. "I'm not gay."
"Maybe you ain't gay, but you sure are a sissy. Those hand-jobs you gave us sure weren't something a straight guy would do. So don't get all fussy-picky now. You already had your hands on me, now give a few licks and I know you'll figure out the rest real quick."
"Yeah," seconded Tyler. "Sissy knows what to do with a cock like a dog knows what to do with a bone. It's in your blood, pansy."
Dylan ran his tongue up the underside of Able's massive weapon. He capped the knob with his mouth and fastened his lips around it. When he sucked, the seated man made an approving sound. Dylan took in the next few inches but that was his limit. He used his hands on the remainder of it, remembering from that night before that they liked to have their scrotums lightly handled too. Pictures were taken of him giving his first head. OMG, if anyone ever saw those he would be ruined. Now, more than ever, he had to keep these four happy, no matter what it took. Able kept him at it for another ten minutes before launching a load into his mouth. Dylan gagged and thick semen leaked out around his wide-stretched lips. It ran down his chin and he knew another dress was getting filthy.
As he swallowed as much as he could, he felt queasy. The reality of having sperm in his stomach made him feel used. He thought of the terms 'cum dump' and 'jiz jar', as they were applied to cheap girls. He was permitted to take his mouth off Able's cock, but the next guy was already calling to him for similar service. Able got hold of Dylan's hair and kept him where he was for an extra half minute, long enough for the Black man to milk out a final dollop of cream into Dylan's auburn locks. Then the oral slave crawled to the impatient second guy. He had to pleasure him and the one after. His stomach was rebelling from all the cum he swallowed. That left only Javon, who still had Dylan's phone.
The Black man said, "I did you some favors. Took some really flattering shots of you with cocks in your mouth, so now you can look at them whenever you want. Feel free to tug on your mini-dick while you're drooling over them and reliving pleasant memories." He laughed. "And I used your credit card to sign you up for a few web sites. After you get out of here I want you to go to them and check out what you find. It's all stuff a sissy like you will get off on." He looked down at the kneeling student in a dress. When Dylan gave him a meek nod of acceptance, Javon went on, "And now you're going to do me with that pretty mouth. But look here." He took something from the floor next to his chair. "Julia's lipstick. She didn't like this color but I thought it would look terrific on you. Get that cute face up where I can reach it."
Dylan complied and Javon gripped him by one ear, holding it firmly, avoiding the spunk that was everywhere else. He applied lipstick all over Dylan's mouth, not being careful about 'coloring inside the lines'. Javon made a joke about the cosmetic being not only waterproof, but 'cream-proof'. Then he sent Dylan to one of the lockers and told him to open it. There was a mirror on the inside. What Dylan saw made him gasp. His mouth was a mess of bright magenta, looking like a child had scribbled on and around it. Javon summoned him and he got back down on his knees at the locker, then crawled back, figuring that was how he was expected to move. The Black leader had him sit up on his heels so he could write on Dylan's chest. First he circled his nipples with lipstick and then he wrote something. He made the white boy look down and decipher the letters from his upside down viewpoint.
"What's it say?" Javon demanded.
"It says," Dylan answered slowly, full of shame, "pussy mouth."
"Right. Mouth like a pussy for Black cock. Say it, girl. Tell everybody that's what you've got."
"I've got a... pussy mouth... for Black cock."
"Sounds good, especially because you did it all whispery. And remember, snowflake, when you say 'Black cock', you've said a mouthful."
That caused more laughter at Dylan's expense. Then Javon pointed toward his own fat cock. The kneeling young man understood and began to handle it, by then knowing what they wanted and how to achieve it. He coaxed it to full erection and then spent a few minutes adulating it with his mouth without putting it between his colored lips. Next he took the first four inches all at once, hoping the move would surprise and please Javon. It was important not to upset him. Dylan gave a dirty blowjob, purring and lapping and making wet sounds. Javon noted how eager his prey was to do a whorish job. He made Dylan draw it out for a while before allowing himself to firehose a heavy load down the smaller guy's throat.
"Not bad for a first-timer," Javon concluded. "But don't worry. We'll keep letting you practice on us. Every night. And I don't want to call you by your boy name when you're acting so girly. How about we call you... Deena? Yeah, I like that. Deep throat Deena. Or you will be soon. With all that practice. And it looks like you got everybody's jazz on that dress. Better learn to swallow more." He shook his head and chortled. "See you tomorrow, Deena. Parting is such sweet sissy sorrow."
When he got back to his place, Dylan put the dress on top of the previous one. He was so shaken up that he wasn't worrying about getting them in fit condition to return to the stock of costumes. And he would have to find another one for the next night. But he also remembered what Javon had said about using the credit card to buy something that would show up on his computer. Dreading what he might see, Dylan went on-line and sat there in his underwear, trying not to think about how he had to keep his body denuded of hair. It felt so feminine. He unconsciously ran his fingers over his satiny thighs as he checked his inbox.
There, right in the middle of the usual ads and notices and Friend Book posts, were several unfamiliar senders. They were SUBMISSIVE SISSIES, DADDIES AND WIMPS and BETAS IN BONDAGE. As soon as he opened the first one and started looking, he was horrified. Everything he saw involved strong Black mean and weak white guys, the latter group all presented in unmanly ways. The sissies were obviously in thrall to their Black Masters, as the big men were called. The white guys all had tiny dicks and the Black ones were all hung like stallions. The second site was more of the same, except that now, instead of just making the sissies pleasure them with their hands and mouths, they were making them lick boots, kiss jock straps, and nuzzle backsides. The last was even more extreme, with the white victims tied up, strapped down, or in very restrictive bondage outfits -- and being used by the powerful Black men as sexual playthings, even to the point of backdoor penetration.
In a near stupor, Dylan gazed at the images. He touched his smooth chest and belly and groin. His hand encountered his penis and he was unsettled to find it at full attention. His fingers closed around it and in his mesmerized state he gave himself a slow motion stroking. He really needed to finish. Just to relieve all the stress he was under. But he didn't want to. Not while looking at guys like himself worshipping the bodies of Black men like Javon and his buddies. He forced himself to leave the computer, though he didn't turn it off. For comfort, Dylan turned to those beloved dresses. He found one that wasn't as badly spotted with his spunk as the others and carried it to his bed. He lay there, curled into a fetal position, hugging it tightly.
Dylan was feeling more in control of circumstances until his eyes drifted to the computer screen. There was a picture of a small white guy kneeling alongside a muscular Black man, hugging his sinewy thigh, his lips pressed against the dark skin of a hip. Dylan groped under the dress and found his little pecker, which was still stiff. He wished it would just go limp, and that his urges would fade away. But that wasn't happening. The on-screen picture changed to something more explicit. He began to pump his hand, which the Black guys had called his hand-pussy. They had remarked on how soft it was and he couldn't deny it. He wanted to close his eyes and think about Julia. She might be unobtainable but he could still dream about her. Instead he continued staring at the compelling images on the computer. Now it was a sissy with his face wedged between the buttocks of a muscular stallion. It had been so wicked of Javon to spend Dylan's money to buy him interracial sissy porn. Still, that was already done and it wasn't worth the risk of upsetting Javon by trying to cancel it. Dylan attempted to call up Julia's face in his mind but instead saw himself in the place of the kneeling figure on the computer and Javon as the standing one.
"Please, no," he murmured. "That's not what I want. I only want J... Jul... J... Ja... Java..." He sobbed loudly. "I don't know what I want." And with that he shot his meager load all over the dress, the one that had until then been the cleanest of his growing collection.
For the next week his nightly visits to the old gym's locker room involved giving hand jobs and improving his throating skills, along with plenty of lipstick that always got smeared. He defiled one dress after another. And then he got an additional unwelcome shock. When he arrived one evening, still trying to puzzle out how to reverse his ongoing emasculation, he found a mattress on the floor.
Javon told him without preamble, "Time to pop your cherry, Deena. Turn the rear exit into an entrance. But don't worry, we got plenty of lube." He laughed unpleasantly. "So get all naked like usual, and into that dress you got hidden in the plastic bag like always. I hope it's a good dress for this special occasion."
Without thinking, Dylan said, "The dress has a corset waist. It will make me look more like a girl. It's kind of uncomfortable but..."
What was he telling them? How would that sound to the rapacious slave-makers? Especially with him using such a feminine voice. He silenced himself while he stripped in front of them and got into the dress that was tight in the middle and billowed out below. They made him circle the mattress and then stand on it and do a slow twirl. There was enough padding sewn into the breast cups to give him the illusion of a modest bust. The room was still as he waited to find out what happened next. Javon came to him and pointed at the mattress. Dylan got into the familiar kneeling posture.
His Black Master, like one of those in the videos, told him, "Get that chin down and your cute ass up."
When that was done, Javon threw the skirt up in the back. The corset waist enhanced Dylan's figure but it was also squeezed him. The Black man got on his knees behind his target and Tyler tossed him a big bottle of lube. Javon caught it easily in his large hand. He rubbed his cock against Dylan's waiting ass to get himself hard. Then he lubed up. The thick business end of his member pressed against Dylan's pucker. The trembling white guy couldn't believe this was happening. It was too much. He might never recover his male identity if he was violated. Javon leaned into him and his knob was forced past Dylan's tightness. The recipient grunted and let out a long moan. Javon gave him time to get used to being stretched.
The Black penetrator said, "I don't do this to Julia. She don't want to be all stuffed back there with my Black jungle snake. Don't want to be all sore the next day. And definitely don't want to take a chance of getting hooked on it. You want to get hooked on it, Deena?"
"N... no," he mewled. "No, Sir."
Javon got a hand between them and groped for Dylan's genitals. He felt them and wanted to know, "If you don't want your ass plugged with big Black cocks, then how come you're puny dick's all hard again?"
"I... don't know," Dylan wailed miserably. "Please, don't make me want this." He sobbed. "Don't get me hooked on it."
"Ain't me making you want it, girl. It's Deena making Dylan want what I got."
As if to drive home his point, he buried another two inches into his captive. Then he invaded him further and further, until he was in up to his weighty balls. As Dylan whimpered, Javon began an evenly paced in-out motion. He took long strokes to make sure Dylan knew he was being well and completely used. Javon's fingers dug into the softness of Dylan's hips. The bigger man rode him steadily for over a half hour, wearing down the last of his resistance. He invited Dylan to push back against him, saying it would make everything easier. Either because he thought it would ease his suffering, or maybe because he was responding to being used that way, the white guy did begin to meet Javon's thrusts with his own backward shoves. That was what it took to drive the Black stud to an orgasm. He gripped Dylan even harder and, with three short hard jabs, was creaming inside him.
Having cum in his mouth and stomach was bad but this was so much worse. He had been taken in the most sissy-like way possible. And his betraying penis was still hard. Javon hunched over him, descending from the heights of his climax. He withdrew slowly, a long strong of glistening spunk attached to his cock even after it was out. He wiped himself off on Dylan's buttocks and got up.
Javon said, "Sloppy seconds for whoever wants them," and Tyler took the spot he had just vacated.
Dylan groaned in expectation of another rampant tool entering him. That was exactly what he got. The final two guys waited, beers in hand, for their turns. By the end there was spunk leaking out of his rear and getting on the mattress. After they were done they made him clean up as much as he could with his dress. He was left sore and beaten, lying on his side.
His Black Master announced, "Not too much longer now, Deena. Maybe another week. Then we'll be done with you. Your debt will be paid."
As stimulated and shaken up as he was, with visions of IR sissy porn dancing in his head, all Dylan could think of was grabbing his own dick and rubbing off a finish. But he didn't want them to see him display a lack of restraint. All he could think about was sex, except that now his thoughts centered on Black men and white sissies. He covered himself and struggled to where his clothes were. Javon didn't like the effort he was seeing. It showed too much spine. It had been a while already since he had drilled that tight virgin tail. Watching the other guys nail Dylan had aroused him. He was capable of another go already. So he grabbed Dylan by his hips and dragged him back to the center of the mattress. He made the white guy take his dark, still unwashed cock and revive it with his hands. Then Javon got where he needed to be and put his battering ram against that overused entrance.
He called out, "Once more into the breach!" and planted himself in it all the way with one mighty effort, making Dylan wail and begin to cry.
After that was over they let him limp away. The promise of more of the same in less than 24 hours was almost unbearable. But Javon had also said there was only a week more of this nightmare. Dylan made a silent oath that he would get through it, if not for himself, then to honor Julia. He muttered her name and Javon didn't miss it.
For the rest of the week they used Dylan any and every way they pleased. He spent his time in class thinking about the night and trying to sort out his mixed up feelings about it all. After his visits to the locker room, he went back to his place and watched more porn, as ordered to by Javon. He was trying as hard as he could not to become, as Javon had said, hooked on everything. Dylan just had to hold on a while longer.
The final evening arrived. Dylan went to the gym with another dress. This one had a much lower neckline. He had to start replacing them before their dwindling numbers were noticed. There were so many lying around at his place. The night before he had slept with three at once. As soon as he was changed into his dress, Javon surprised him.
"We got to celebrate, Deena. How about you have some wine? It'll make you feel better. Get you relaxed."
"Well, you've haven't been very nice to me and..."
Javon held up an interjecting finger and reminded him amiably, "We've just been trying to help you pay your debt, and let you get in touch with your feminine side. You know, sometimes you've got to be cruel to be kind, in the right measure. But no hard feelings. Right?"
Dylan appreciated Javon's consoling tone. He accepted a glass and sipped it. Able wanted his balls lapped right away but Javon told him to wait. Again Dylan was soothed. He drank more wine. Then two of the guys got into a discussion. They were saying that someone could take wine in an enema and it would get them *****. It sounded like it was something they had debated before. They went back and forth until Javon interrupted.
He said, "I got fifty bucks says it's true. And I got a enema set-up in one of the lockers to prove it. I wanted to be ready to take your money."
Tyler said, "You're on." The other guy said the same. "Now let's see some proof. Otherwise just shut up and pay up."
Javon pointed out, "Yo, I ain't got nobody to try it on."
"Then you owe us. Unless maybe Deena there wants to let us try it on her."
"No," Javon told them. "This is her last night and that wasn't part of what we planned." He got out his wallet and cursed. "Damn. I should have waited till I figured who to use."
Dylan, seeing a chance to really clear himself from any carryover trouble, and deciding that the treatment wasn't harmful, said, "It's okay, Javon. Sir. I'll do it."
"You don't have to."
"No. I want to. So you'll understand that... I don't know... that I'm okay."
"Well damn," Javon said, giving Dylan's small hand a hearty shake. "Guess I'm going to earn some easy money now. Maybe I'll split it with my new business partner."
He made Dylan fetch the rubber bag and tube. Able grabbed a half empty bottle of red. Their test subject had to kneel on the edge of the mattress with his bare bottom raised. They quickly got everything ready and Tyler popped the nozzle into his rectum. As the valve was released, Dylan felt liquid rush into his bowels. He got a full feeling and then the valve was shut and the piece in his bottom was separated from the tube, so he could move around. Very soon he felt the effects of the alcohol. His head was spinning. Tyler said something about how Dylan could just be faking drunkenness. Javon considered that.
He said, "Yeah, guess you're right. How about we cancel the bet?"
"Sure. No big deal."
Dylan, now reeling *****, was vaguely disappointed. Weren't he and Javon buddies now? Working together? Maybe going to split the money?
"And I got to step out for a while," the group's leader said. "You guys keep Deena entertained. Show her a good time for her last night. Help her get in touch with her party girl part."
Feeling too ***** to get back up, Dylan watched hazily as one of the others dropped his pants and knelt in front of him. By reflex, Dylan used his mouth to get the proffered cock hard, then began to suck it. He used all the tricks he could remember learning. This was like being in one of those IR sissy videos. And he was the star. He finished the very sloppy BJ, gulping down semen but also getting it on his chin. The wine was sloshing around inside him. When he seemed like he might pass out they helped him up and walked him, between two of them, to the bathroom. Then they positioned him over the toilet and pulled his plug just as he sat. Dylan emptied himself into the bowl and sat there with a lopsided smile on his face. Someone used the lipstick on his mouth, doing an amateurish job but not as intentionally bad as Javon had before. He was taken back to the mattress and put on his knees.
Dylan was aware of two more cocks being offered to him. He handled them, went back and forth between sucking the one on the left and the one on the right, and then finished each in his mouth, letting cream mixed with saliva run freely over of his lower lip and down his front. He saw how badly the dress was getting streaked with it and laughed. The room was spinning. Someone gave him a pill that they said would help him sober up and a swig of wine to wash it down. They left him the bottle. He laid back, clutching the bottle to his chest, dimly aware that wine was running out onto the dress. He was dimly aware of the lipstick being tucked into the top of his dress.
Then, for some reason, they were putting something around him on the mattress. Pieces of paper? Pictures? His head felt funny. Maybe a side effect from that sobriety pill. He wondered when it was going to start working. And then he passed out.
Meanwhile, Javon had showed up at the rehearsal space shorty after leaving the gym. Julia had asked that everyone involved with the show gather there. She had noticed that the dress she was supposed to wear for the impending performance was gone. When she searched for it she found that many others were also missing. Everyone showed up to discuss the situation. Everyone except Dylan. Professor Smyth was concerned.
Javon defended the missing student. "I mean, why would he do anything with the dresses? They were his responsibility." He made a show of thinking for a few seconds. "On the other hand, why didn't he notice that a bunch were missing? And report it?"
That was all it took to set the others off. They had all noticed how oddly Dylan had been acting for weeks. Like he had something to hide. The girls were especially suspicious. As they discussed it now, Javon still occasionally tried to defend him but opinions were solidifying against the only missing person involved. Javon joined them, but with a show of reluctance.
He said, "Now that I think of it, I have noticed his car at the old gym a few times recently. I figured he was working out. You know, because he's so slender and kind of a weakling."
Julia said, "Maybe we should go over there and take a look."
The Professor backed her up with, "Whatever's going on, I'd like to get this straightened out before opening night."
"Well," Javon said optimistically, "it'll be worth it if we can clear the kid's name."
They all piled into cars and drove across campus. When they got there, Dylan's car was the only one on that lot and the side entrance of the building was open. The group entered and someone saw light coming from under the locker room door. They went there and when the door was flung open and they went in, they were stunned by what they found. There was a mattress on the floor and on it was Dylan, in a dress, his lower body *******. He had one hand on his tiny flaccid penis and the other reaching for a bottle of wine. Spread around him were print-outs from a computer. As people began to pick them up they gasped at what they saw. In every picture Dylan was involved in some sort of lewd sex act, while in a dress, and often looking quite happy about it all. Then they realized that he had semen on his lipstick-colored mouth and his lower face. It was also on the front of the dress, which was stained with wine.
"That's my dress for the show!" Julia lamented. "And there's my missing lipstick sticking out of the neckline."
"This is scandalous," Professor Smyth cried. "I don't want anybody talking about it outside this room."
"It could make the college look terrible," said someone from the rear, someone who sounded like Javon. "It should be handled quickly and decisively. By the college authorities."
A moment later Dylan sat up, blinking his bleary eyes. He said in a slurred voice, "We had a party. I'm a party girl. My name is Deena. Don't call me Dylan."
"Young man," Professor Smyth said, sounding uncharacteristically stern, "you are in serious trouble."
"Wh... what?" Dylan got shakily to his feet and stood there swaying. He was coming to his senses. "It's not my fault," he whined. "It was Javon." He spotted him and pointed. "He was here the whole time. He's the ringleader. There's a whole group of them. I'm not a sissy. I'm not gay."
"What?" It was Julia. "He couldn't have been here. Javon was with us for the last hour." She took his hand. "And I know he could never be involved with anything like this."
Professor Smyth said, "I'm calling campus security. This will not go unpunished."
"And there are still a lot more dresses to be accounted for," Javon added with concern. "You don't think they could be... at his place?"
They went there next and found not only the stained dresses, but Dylan's computer turned on and IR sissy porn running on it. Someone realized it must be a pay site and someone who was a computer science major checked the machine, discovering that he belonged to three pay sites, all with variations of that theme.
The next morning, with the Professor laying out the evidence, and Javon and Julia present as concerned members of the theater group, a hungover Dylan was expelled. He couldn't believe it. At the same time, more demeaning pictures were being leaked anonymously to everyone in the theater group and a number of other students.
As Dylan walked dispiritedly away, a car pulled up alongside him. It was Tyler and Able.
Tyler told him, "I don't think you want to run home to your ******. If you do, somebody might send them a bunch of nasty pictures of you, Deena."
"Yeah," agreed Able. "You need to like get a job and someplace to stay. So I talked my uncle into hiring you. Get in the back of the car."
Feeling like his world was crumbling around him, Dylan numbly obeyed. It turned out that Able's uncle had a janitorial business. They took Dylan there and got him some coveralls. All the ones on the rack were orange except one, which was pink. That was what they gave him.
"Now strip down," Able's uncle told him. He was a hard-faced Black man with a cigar stuck in the corner of his mouth. "You can leave your street clothes here."
Afraid to protest, Dylan got naked. Tyler handed him a rainbow-striped shopping bag. Inside were pink, bikini-cut panties, and a matching garter belt and stockings set. He obediently put them on, having some trouble with the stockings but ultimately donning them. Then the coveralls went on over top. He was given pink running shoes to complete the demeaning outfit.
"Now," Able said, "we'll hold onto the keys for your old place. Help you get moved out. Try not to accidently give all your boy clothes to charity. If we did that, you'd be stuck in the girly stuff we're going to buy with the cash from your wallet, and order with your credit card."
"But... where can I stay?"
"We'll move you into a little apartment my uncle is renting you. Of course, he can't afford to pay you much, since you lack experience in the janitorial field. But you'll be able to make the rent. Barely. Now we'll drive you to your regular assignment."
Still feeling disassociated from himself, Dylan let them drive him again. But why were they taking him back to the campus after his expulsion? As they got him out of the car, passing students gaped at him in that pink jumpsuit and shoes. Some of them had seen the photos of him. Others had heard whispered stories.
"Now just walk yourself across campus to the administration office and report in. I think today they have you cleaning the bathrooms in Alpha Afro Alpha."
"The Black fraternity house? But I can't go in there. If those guys see me like this, I don't know what they might do."
"Yeah. Who knows? And it would be even worse if somebody fired off a bunch of them pictures of you, with Black cocks in your hands and mouth, to them brothers. Pictures with Black cocks but no Black faces. Just your face."
As Dylan started toward the administration building he saw familiar figures strolling toward him. It was Javon and Julia, hand in hand.
She looked at him critically and said, her voice furious, "You are pathetic. I was sickened when I saw you lying there, ***** and covered with semen, your dick hanging out. And that thing between your legs is so small. What is that? Some kind of medical problem? You are a complete freak, Dylan."
Javon told her in a calming tone, sounding not at all urban like he had when he was in the locker room, "I think he told everyone last night that he prefers to be called Deena now. And he can't help it if he has an impossibly small dick, something no girl would ever want. His issues with being sexually different and seeking certain types of partners and abnormal acts, well, that's for him to deal with. Deena may seem like what the Bard would have called a puling whelp, but there's always hope. For now, we can only offer him our pity."
Julia took Javon's arm. "Oh, baby, you are such a good person. I'm so lucky to have you." She gave Dylan a final withering look. "And I'll try to be sympathetic toward creeps like... Deena. But it's not easy. I'd be just as happy if I never had to set eyes on him -- or her -- or whatever -- again."
Javon concluded, "Thus ends our drama." A moment later he gave Dylan a private wink and added, "All's well that ends well."
As they walked away, Dylan began to tremble. His last dream had just been shattered. Julia despised him. Soon he had to face the Black members of Alpha Afro Alpha house. And he couldn't see any way to get out of the trap he was in, especially with those blackmail pictures available to send to friends and ******. Everyone's address had been on his computer. He was doomed.
Even though he had been unceremoniously thrown out of college, he was still going to get a lot more schooling.
*********
(This story is from an outline by Devin Dickie, who also provided the clever title.)