Chicago Trip By Green

Tracy and I had dated for over two years, our Junior and sophomore years in college. Tracy got an internship in Chicago for the summer. I stayed back in Michigan to catch up on two classes but took them at an accelerated pace so that I had six weeks off before the fall sessions started. I planned on joining her for a couple weeks presuming her roommate (assigned to her from another college) did not mind before going home to rest up for the last year of undergraduate school.

Tracy had always been faithful during our relationship. She was not promiscuous in nature anyway. I had been her fourth lover. I had strayed whenever my studies and work provided the time but finally had decided to settle down and try being monogamous with her. The irony of who was the last one to settle down was not lost on me. I am an average looking guy with a body consistent with the heavy mileage I ran each week. She was an absolute knockout. At 5'9" tall she was nearly my height and voluptuous build. She was a size-7 with a wonderful c-cup build of 37-25-34 (approximate, it is not like I ever measured). Her thighs and backside had the look of a young woman that spent a lot of time on a Stairmaster. She wore her shiny jet-black hair shoulder length and cut away from her naturally tanned face and large almond sized green eyes. She was a mix of Asian, German and Italian. She looked mostly Italian with her height and frame from her German genes and the Asian showed through just a little and gave her quit an exotic look. I was one of four guys that knew where else her Asian genes showed up, ha-ha, she had very little body hair and her woman juices flowed like water when she got aroused. I think most woman are (I guess like most men) general the same in their private areas. you know, small-medium to medium plus. She was small down there; noticeably tight. Growing up in a mostly black school system I thought my penis was small (I later learned the physical fact that some races shrink up when flaccid more than others, of course, speaking in generalities) but once I started having girlfriends found out my erection was medium plus. This made sex with her that much better. There was no such thing as a quickie with her. I needed to get her aroused before sex and needed to take a few minutes with her with gentle penetration before I could "fuck" her. She preferred lovemaking, which is mostly what we engaged in but every now and again..

Anyway, I had not seen her for the entire 8-week semester. I called to let her know that I would be there the following week just a day after my last final. I also told her how thankful I was that she had been patient with me and that I knew that she knew I had played around a little during our relationship. I told her that those days were behind me. That I finally had matured enough to understand what I had with her and was ready to settle down. I informed her in a matter of fact tone that I had not even went out the bars with the guys let alone date the entire time she was gone. I had decided to take the last step a few months back but wanted to prove it to myself before sharing this with her. I expected a positive response. Instead, there was a long pause, a very long pause. "Tracy, are you happy with this?" I asked after nearly a minute of dead air. We went back and forth without her confirming that she was happy to hear this. We ended the conversation with the fact that we would talk when I got there. She did let me know that she was happy that I would be there for a couple of weeks or so and that since her and her roommate had a two bedroom apartment that me staying there the entire time would be okay.

I spent a lot of time trying to figure out what the lack of response could have meant. All I could figure, and I got this from discussion of it with one of my roommates, is that she had taken the opportunity to have an affair or to date around a little while we were apart. After all, I had not been monogamous. It was the perfect opportunity to "sow her wild oats" or whatever, something growing up in Iowa had never provided her a chance to do. Heck, even if it had it was just not her way. She was after all, the naturally innocent type. For many reasons I did not seem to care that much. I was deciding to be monogamous simply to please her. I had no intention of getting married until I was at least thirty. Besides, I was still going to be sharing a room with her when I got there. So, it was not like she broke up with me over the phone. Hell, the whole thing intrigued me. I couldn't wait to hammer the last exam and get to Chicago to see what was up.

After the last test I took off like a bat out of hell for Chicago getting there in five hours. I got there that Friday evening. I settled in quickly to "our" room getting a chance to get "my dick wet" twice with her before even starting the process of catching up on the last couple months. Of course, we went through all the chit-chat about her work and my school and made plans on when I could see where she worked and what I would do when she was at work (be tourists all day long! Chicago is a great place to visit any time let alone the end of summer). She seemed very different. She had really grown by being out in the "work force" in a distant big city (five hours from campus). The thing that really seemed different was that she carried herself with much more confidence. She was a little worldly now.

When we came out of the room her roommate was in the kitchen making dinner. She was making dinner for all of us. Her roommate, Chia, was from Los Angeles and was equal to Tracy in the looks department. Chia was as tall as I was, a couple inches taller than Tracy was, and either a dark Hispanic woman or cocoa skinned African woman. The description depended on which heritage she claimed since she was half Hispanic and half African-American. Chia wore her black hair short and straight back of her beautiful head. She was very thin. She ran track at her college, middle distances, and had the body for it. Don't get me wrong, she was a very attractive woman! She was sleek, lithe and had cat-quick looking sinewy muscles everywhere I could see. She was wearing short-shorts and skin-tight t-shirt. Her rounded breasts didn't need a bra. She may have been an a-cup and had the legs of woman able to run a series of sub 2-minute 800M intervals but she seemed every bit as sexy as Tracy. She had a smile that lite up the room and easy, "I am queen of the world" confidence that I immediately gathered had wore off on Tracy over the last two months.

We had dinner and got to know each other and then decided to go out clubbing that night. Of course that is what we decided to do. It was Friday and we were college students!

We got dressed up clothing for a hot summer night out and went to a place called "Tonight". Chia had put on a surprisingly neon orange summer dress and Tracy wore a lite green summer dress that clung to her angles like a paint job in all the right places. Tracy and I had not even begun to have our follow up "talk" (to her hesitation, lack of response to my declaration) and we never did. As it turned out we never needed to. I just welcomed myself into her Chicago world and found out everything I needed to know as we went along. I had dressed in typical yuppie college clothes that I thought would be fine. Heck, it was good stuff. It was for certain types of places. But "Tonight" was a hip-hop dance place and I think I looked like a nerd. Well, okay, I do not think I looked like a nerd, I did. Everyone there, except me with my "college preppie" appearance looked like professional types (you know, middle class or above business types) dressed out a GQ. Other than one bartender I was the only white guy in the place. Tracy was one of only three white women. The place was hip, neon lite-up and had a fast and furious atmosphere. There wasn't anything like it back near campus in Ann Arbor.

It was a night of fast paced dancing and drinking. I had fun dancing with other woman and Tracy danced with quit a few other men that knew her. "Tonight" turned out to be where Tracy and Chia went to most Friday nights and so Tracy had gotten to know the "regulars". She had even introduced me to a couple of them. She introduced me as her college boyfriend and after introductions and brief greeting she would go dance with them for a few songs. I would either have yet another drink or dance with one of the beautiful black woman I was fortunate enough have gotten a "yes" out of when I asked them to dance.

It was a blast and the beginning of a fun and wild two weeks that involved the wildest sexual things I had ever done in my life. I got to have sex with Tracy a couple times a day. I got to have sex with Chia a few times and twice got to have a threesome with Chia and Tracy. I also got to participate in a group setting once. That incident is what this story is about.

At closing time we went to a 24-hour breakfast place. There were four of us. Chia brought along her choice for the night. His name was David. He was an affable but very dominating fellow that towered over me. Well, I was pretty impaired yet fully functional. I think he was in the same physical state as I. Chia and Tracy seemed the sober ones of the four of us since they had danced so often and freely though they had had enough to drink to be giddy and silly.

I think I took the evening on the turn that took me on a wild ride with a joke aimed at my new lawyer friend, "a black guy named Dave eh?" Being a little intoxicated everyone laughed at the silly joke but really laughed when he replied that his real name was "Kemutabah" and added, "but I go by Dave because my white clients feel a lot more comfortable with that."

It was a fun conversation that we were having over breakfast when this juncture took place. Dave took over the situation at this point and I credit him with making the whole wild night happen. He continued, "so, either Chia has a taste for vanilla or Tracy for chocolate, which is it?" Chia said in a sultry voice, "it's all good." This brought on another round of laughter as much from the comment as way she delivered it. The lite-hearted deliveries continued during the discussion of the rainbow of race but there was a twist to the conversation. I had never been in just a free flowing get together but could sense it. It was clear that there were two guys and two girls at the table. But to David it was not clear who was going to pair up with whom. I was a na've to this type of thought but had enough street smarts to see that he was either keeping the options open or was trying to get them open. Keep in mind that the things that happened on my stay in Chicago that I listed above had not happened yet. This was the first and the wildest.

"You ever been with a black man?" Dave directly and abruptly asked Tracy at this point. This would have been a question too direct but from him and his very domineering personality it seemed normal. He had personality similar to that of Chia, it was his world and he could ask anybody anything. "That is personal information", Tracy responded. The way she said it caught my attention. If you understood my personality and outlook on life you would understand my follow up. See, this was the summer of '98, two years ago, but if I could go back in time I would fit right into the 60's, you know, flower power and each to their own. I took her response as a "yes" and wanted to know more. Dave took it as a "yes" as well. Man, he did not play around and his questions, though delivered gently and comfortably, reflected his controlling personality and profession of a lawyer - he cut right to the point. Though Dave deserves credit for making such a wild night happen I think I did one thing that was critical to keeping everything fun and on the surface. Before Dave asked another question I had felt Tracy slide her hand over to my thigh. I took her hand and gave it a reassuring squeeze. I leaned over and kissed Tracy on the cheek and whispered into her ear, "so glad to see you again, I missed you so much." I had paused for a brief moment after that and then kissed her gently again. Then I continued, "we are in Chicago, let's have the time of our lives." It did not come out as I intended but she seemed to understand what I was saying, "it's all good", as Chia had said earlier. Let's have fun, no regrets and all of that. I felt her hand that was tense on my thigh, relax and go soft and could see her face relax as well.

"Was it just a booty call or have you ever date a black guy?" Dave continued. Tracy responded, the moment of tenseness past, "I have never had a booty call." Dave somehow took the conversation back to a very casual tone. We all talked like friends about relationships and what we are looking for. Essentially, all of us where happy with our current lovers (Chia had a boyfriend back at college and his girlfriend was out with her friends for the night) and circumstances but agreed that things come and go and besides, none of us planned on getting married in the next few years though the time may come and may even happen with our current lovers. Tracy had said this pretty matter-of-factly, a real change for her. As opposed to being jealous, simply not my nature - heck, the whole concept seems so silly and confining, I joked to myself that I had just wasted eight weeks of freedom, ha!

Anyway, Dave brought the conversation back to where he wanted it. (Sidebar: Looking back, which I did before I decided to write this it seems like Dave was a voyeur or something like it and looked for opportunities to make happen what he did that night.). "Either of you woman ever sleep with Mandigo?" Dave asked with a nonchalant air but his eyes were very penetrating as he waited for a response. Heck, that one went over my head. When neither of them responded he elaborated, "you know, the black myth." Wow, he was direct and more than a little curious. At this point, we were all done eating and sipping coffee. I was not sure why he was trying to brag - that is what I thought he was trying to do at that point. I thought it was clear that we would all soon be back at the apartment with him staying over. The only question to be answered and, to me, only for him, was which woman he would be with. For a couple of minutes I thought he was trying to let the woman know he was hung. That was not his angle though.

"That is just a myth", Chia said. David laughed and turned towards me and asked, "you ever been in a locker room with black guys?" I chuckled and said that I do not think it is just a myth but that I didn't really know since I had not slept with too many black men. Of course, I said this as a joke. Everyone chuckled and took it as such (v. thinking I was coming out of the closest). Chia said that she had been with all the races and was pretty sure it was a myth. She continued by pointing out that she had noticed a significant difference in the size when flaccid though. To my surprise Tracy let out a nervous laugh at this comment. "Well, that laugh has a story to it" Dave said with a grin. He looked right at Tracy and waited for a response to his non-stated question. I do not recall her exact words at this point. I was pretty amazed at hearing her talk so sexually and openly at this juncture and have to paraphrase for the story. Tracy admitted to having been with a black man at this point (I later found out that she had had her 5th, 6th, and 7th lover - remember, I was her 4th -while in Chicago and all of the men had been black) and that the first thing they did was take a shower - they had went to a work out at a local gym together - and was taken aback by his flaccid size. She said she was thinking about giving him a great blow job when she was soaping up his penis and felt its size but that when he got hard he was "normal" sized. They wound up having sex and she liked it. She had not thought of his size again until her next lover, also black, and remembered her first impression of her first black lover when the second black guy she had been with went flaccid after his first orgasm. She said that when she held him to start the process all over again she noticed his flaccid penis being large also. Then, when he got hard she noticed that he was "normal" too. Dave asked her what she thought "normal" was. She responded, affectionately touching my thigh at the same time, "Dale (that's me) is normal to me, perfect to be honest." Dave asked her if she thought I was typical of white guys. Happily to me, she said, not exactly, he is an inch or so bigger than the lovers I had before him. I like his size, it fills me up.

Dave really got interested at this point. His questioning got him information that really peaked his interest in Tracy. he found out that I was only her fourth lover and that had just recently had a sexual encounter with someone that was not a long term boyfriend. He had a look on his face like, "ah, fresh blood."

"Well, there is more to the myth than just a difference in the soft state. Some races, well the black race, produces a horse now and again", he chuckled, looked directly at Tracy and continued, "well, more than now and again, you just haven't gotten lucky yet." At this point, Chia chimed in after being quiet for the last ten minutes, "maybe so, but it can hurt." "Ha!" Dave said loud enough to get the attention of those in the breakfast place to look over at the noise. "Thanks for coming clean my sister." Man, Dave was like a kid in a candy store at this point. Like he had just closed a big case. Maybe he was good at his profession of being a lawyer but at sales he could have been king. He got up and said "let's go to my place." Up until this moment I thought he was conveying to the woman that he was hung. I thought he was doing this needlessly since it was clear that he was going to get laid that night but I figured his angle was to get Tracy interested in him and have her be his lover for the night and for me to wind up with Chia (not a bad idea in my book as I later discovered, damn, she had skillz.). Dave hailed a cab and as soon as we got in as if sheep following their shepherd he used his cell to make a call. All I heard was, "wake up sleepy head, I am bringing home a party." He was talking to his roommate that he rented out one of his three-bedroom condo rooms to.

We just settled into his plush living room when a rail thin, dark as night Nigerian walked into the room with nothing on but some jumbo sized basketball uniform pants on. Dave introduced him as Nile. Nile said very little and seemed to be in the process of waking up. It turned out that he was already awake. He was an artist trying to make a living and simply was off in his own world and said very little the whole time. He was awake and alert, it was just his nature to be relaxed like his car had two gears, neutral and first gear. After friendly introductions, Dave got out a bong and we all started taking hits. I was along for the ride and having fun. I had plenty of money in my pocket for cab fare and no one had anything responsibilities the next day. Yep, it was time to get high.

We all took the next fifteen minutes to get a buzz going that we maintained for the rest of the night. After everyone got their buzz going the conversation picked up again.

Dave took things back into the fun zone. He looked at me, I guess out of respect, to make sure I did not have any negative vibes over him sitting next to Tracy as he moved to the couch and sat right next to her. He quickly moved his around her shoulders and gave her a gentle kiss on the face. "I am going to rock your world tonight and that is all I wanted in return", referring to the little peck on the check. He got up and went in to the kitchen to return a couple minutes later with a bottle of Hennessey and a chilled glass. He sat across the room as if at a theater. I was a little lost at this point having thought Dave was alluding to the fact that he was all that in prior conversations. "Come on Nile, let's get the show open", Dave said with a chuckle.

Nile laughed and lazily stood up and went into his room. I did not know what was happening yet did not care. Dave had lite up another big spleef and the girls on the couch and me on a nearby recliner was enjoying it. Just about half way through it Nile returned to the room dressed in a street version of a hockey outfit. he had put black eye on and everything (black eye more for the glare of an outdoor baseball game but I guess it was part of his outfit?!). He put a tape into the stereo system and boom, it was a high paced dance song ideal for stripping. He stood in front of the girls on the couch and started his show. He seemed to be natural talented at this and based upon how casually he went through his routine it seemed like he must do it at least part time for money. He was barefooted so the first thing he got rid of was the jersey. His showed off his muscular and wiry frame, which we had already seen but not in motion, for a while and then started to peel off his "hockey pants". Suddenly the little joke hit me and I laughed. His outfit was that of the New Jersey team, get it? The "devils". Okay, I guess it didn't warrant a laugh but remember I was pretty buzzed and little things seem big time funny in that condition. He turned around and peeled off the pants and did the proverbial hydraulic paced shaking of his butt for the girls for a short while before turning around to gyrate in front of them. He had the athleticism of a gazelle with his movements. When he turned around he sure got the girls attention. His jock strap obviously had been stuffed with a small pillow for affect but I guess when it comes to shows that costumes enhancements are part of it.

Nile danced in his jock strap facing the girls for the last minute of the dance tune coming out of the stereo and when it was done he stepped up to them as if to get some dollar bills tucked in his strap. Chia played along and reached for her purse for some singles and tucked a couple of them in as another song started. Nile continued his routine for a couple of minutes and then teased the girls, repeatedly starting to pull his jock off but then letting it snap back without taking it down. Chia got the hint and took out a five-dollar bill and tossed it on the "stage". Continuing to dance he looked down and then shook his head "no". I pulled a twenty and gave it to Tracy. She tossed it on the stage and that brought a smile to his face. I think it was go with that amount. He turned around and so that his back side was facing them and then peeled it off as slowly as he could. "Holy.", I started to say but did not finish. The girls could not see what I could see given their vantage point. I was absolutely amazed. His cock was not normal. The only thing I have seen similar to it are the enhanced pictures you can find on "massivecocks.com"!!!

Then Nile did a 180 dance spin in the air and there he was in all his glory for the girls to take in. They both brought their hands up to their mouth reflexively and sat back deep into the couch as if hit by a sonic boom.

"You can touch it" Nile said in his deep, quiet voice to whomever would be the first taker. Neither moved, they seemed hypnotized by his cock. Both of them simply staring wide-eyed, scared and enthralled simultaneously. Chia moved first but not for herself. "I am not going near that monster," Chia said as she grabbed Tracy by the wrist and brought her hand out to the "thing". "Oh come on now, just do him," Dave said jokingly but impatiently. Chia moved to the far side of the couch and then moved over to me and sat on my lap. She had left Tracy to the experience.

Tracy had grabbed a hold of Nile's cock with her hand. He was moving slowly sensually moving his cock through her hand. "Go ahead, use the other one too," Nile instructed and Tracy obeyed. He continued to move seductively between her hands. Tracy then put her mouth on the end of it. She could not get her mouth around it but used her tongue and lips to get the head wet. It was a pretty sexy vision. He was a pretty horny guy given how often he must get laid. He was already dripping precum and it made stray strands connected by his cock head and Tracy's lower lip and tongue. Impossibly, he was getting bigger as he was getting harder.

"You like this?" Chia whispered to me obviously feeling my erection as she was cuddling with me on my lap. I felt her soft bubbled butt grind into my hard erection. I did not need to response.

Apparently, Nile was not really planning on making this an all night event. He enjoyed Tracy's wet hand job for a few minutes then directed her with his hands on her shoulders to stand up. Nile took less than a minute to disrobe Tracy and then moved to embrace her as he kissed her. I cannot imagine how big Nile was since I really do not have reference point. But, he must have been in the area of a foot in length. I guess this because as they were kissing he had positioned his cock between her legs and there was over a half foot sticking out as if she had been stabbed by a sword and it was coming through her body. He was humping her crotch with his cock and either he was dripping an amazing amount of precum or she was very, very wet by all this because the top of his cock was wet and glistening after a couple of strokes. I knew Tracy loved this because I do it to her myself. She loves it when I stroke my cock between her lips, running the back side of it through her pussy lips and over her clit for a while before entering her. He was doing it with the top of his cock but it seemed to be a facsimile of the foreplay she loves so much.

They continued this foreplay for quit a while as their kissing became quit passionate. Next, Nile showed how flexible he was. "Put it in" he directed as he arched his back like a cat and dipped downward to position his cock head against her vulva. She reached around behind her butt and put the end of her fingers on his cock head. Apparently, it was properly positioned at her entranced, "be gentle," Tracy said. Nile pushed up with his legs and Tracy let out a gasp as she wrapped both arms tightly around Niles' shoulders. Nile was pushing in and out with very short strokes likely intended to let her adjust to his width, which was as impressive as his outsized length. "Careful, its too big for me" Tracy said. Nile took a hold of both her ass cheeks and lifted Tracy off the ground and set her down on the couch. He sat her ass on the edge of the couch and kneeled down on to the carpeting. Man, what a sexy site this was. Nile spread her legs open and Tracy put her hands down on the outer lips of her pussy. She was spreading the natural lubricant the two of them were generating around his shaft, the nearly 8-9 inches that he was not even putting in with his 3-4 inch strokes. Sweat beads were on Tracy's forehead and her breathing was short and in gasps. She would make a gasping noise with every inhale that she was instinctively timing with his inward thrust and then make a moaning noise almost a sound of relief whenever he would pull it out to the head.

"Are you going to fuck her or what?" Dave asked Nile. "This is enough," Tracy answered for him. Nile back at Dave and they engaged in some type of nonverbal communication as Dave nodded. Dave got up and took one of the cushions from the couch and set it down on the floor just a few feet from Chia and I. Nile then picked Tracy back up and then set her down with her back squarely in the middle of the cushion. Dave sat at our feet and took a hold of Tracy's wrist and pulled her arms back over her head. Nile resumed his short little thrust into Tracy. Dave was holding Tracy in place though she was not squirming. "Okay, get re." Nile thrust in a few inches before finishing his statement to Tracy. "Aaaarhh," Tracy screamed at over half of his cock thrust into her small pussy. I am telling you that he was one thick cocked guy. Tracy had experienced 7 inches before - mine - and though it "filled" her up she did not react like this. It was his width that was tearing her up at this point. "Please stop, it is too big" Tracy pleaded. Nile seemed to be deaf at this point or simply too into it to care. He was thrusting rapidly in and out of her with each thrust going past the half way of his cock. Even though he had been fucking her hard for a couple straight minutes her pussy simply could not adjust to his side. Tracy was literally squealing and was trying to buck her hips free of him. Nile held her hips firmly in place with his strong hands though and continued to hammer away. Her pussy lips were so tightly pulled by his width that it seemed like part of the inside of her pussy was coming out with his withdrawing motion. And then her vulva would follow his cock inside of her nearly an inch with his half foot thrust. I could see her arching backside down as Nile attempted to thrust in a little firmer to deny him clear access. He was dripping sweat now and had the look of being intensely focused. He seemed driven to get his nut. He reach for her ankles at this point of her pushing her butt down into the cushion and spread her legs apart and moved her legs up against her chest. This was another amazing view. I could see her pussy lips going in and out an inch as he went in and out over a half of foot and then a full nine inches in and out rapidly and fiercely. She let out a screech loud enough to prompt Dave to let go of one of her wrist and to cover her mouth when Nile pushed in past the half way point towards the three quarter point of his cock. He seemed to run smack into a wall with the thrust likely hitting the bottom of her pussy and being physically forced to not go any further. He ripped into at this depth for over a minute fully bring his cock all the way out to the middle of the head and then sliding forcefully back into the much too tight pussy. "Dave, this is the tightest pussy you ever brought me." Nile said and before he seemed to complete his thought he grunted something and then pulled out his massive cock and let go three full spurts of his cum that shot in and high arc and landed onto Tracy's breast area. "Man, that was a good show Nile, let's have another joint", Dave said as the two of them got up and went over to the couch to share a freshly rolled one.