Akira focused on keeping his nervousness under control as his girlfriend hummed happily beside him. Sadayo was listening to the song playing from the CD player in her car. Akira didn't really recognize it, but he thought it might have been popular a decade ago. His girlfriend was driving them to their destination for the night. It was the house of one of her old clients. Though Sadayo had quit her job as a maid months ago, she had retained the phone numbers of some of her clients.
Sadayo had told him that she hadn't intended on calling any of them again. It had just been a pain to delete their contact information. As it turned out, those numbers were pretty convenient to have. They made setting up tonight's activity positively easy. At least, logistically.
"We're almost there. Are you sure you want to do this? I told him that it's not a done deal until we show up at his door." Sadayo asked Akira beside her, just as she had when they had first got into her car.
"I'm sure. It would be a shame to back out now." Akira replied from the passenger's seat, trying to sound more at ease than he was.
Akira had good reason to be nervous. His girlfriend was intent on fulfilling his fantasy tonight. Akira's fantasy just happened to be a desire to see his girlfriend get fucked by another man. Which was going to happen, assuming everything went well. That was enough for anyone to feel a little nervous about, but Akira had something else to worry about. Maybe his unease was readily apparent because his girlfriend glanced over at him again.
"I think you look great in that outfit. Almost as good as I do." Sadayo said cheerfully.
Sadayo did look pretty good in her black and white maid's outfit. It wasn't exactly demure, but it wasn't meant to be. The low-cut front showed off her breasts nicely, and the black skirt on her outfit ended at mid-thigh. Sadayo wore white stockings that contrasted well with the skirt and had a pair of black stilettos on her feet. His girlfriend had her jet-black hair tied in two long ponytails and topped it all off with a fluffy white maid's cap.
The car Sadayo owned was an old, fairly beaten-up Nissan Sunny that his girlfriend had purchased for a song. From what Sadayo had told him, it always seemed on the verge of breaking down but (thankfully) never did. Though the car was of dubious quality, it had been a necessity while Sadayo had been working at her night job. After all, she could hardly board the subway in her maid's outfit, nor was changing in an alley a realistic possibility.
They came to a stoplight as they entered Azabu-Juban, the district where Sadayo's former client lived. Sadayo took advantage of the delay and flipped down her visor, revealing the mirror there. Akira watched his girlfriend rummaging in her purse until she pulled out some lipstick. Sadayo used the bright streetlights around them as illumination while she refreshed her soft-pink lipcolor in the mirror. The light turned green soon after, and Sadayo passed Akira her lipstick as she drove onward.
"Here, try this." Sadayo said in the same cheerful voice.
Offering her boyfriend her lipstick might have been a strange thing to do most of the time, but not now. Akira glanced down at what he was wearing, reminding himself that this was a two-way street. His wasn't the only fantasy that was being fulfilled tonight. Sadayo had been uncertain about engaging in the cuckolding play Akira wanted until he had asked her if he could fulfill a fantasy she had. As it turned out, Sadayo had a secret desire to see her boyfriend in drag.
Though Sadayo had couched it by claiming that the client would only let Akira watch if he was dressed as a maid as well, he had seen how enthusiastic Sadayo was at the idea. His girlfriend had happily spent hours on her sewing machine altering her spare maid's outfit to fit Akira's different physique. Sadayo had then dashed out to buy some feminine accessories that she couldn't alter from her own, like a bra and some stockings.
Akira had put on the completed outfit an hour earlier and had been surprised by how he looked. It wasn't exactly the first time he had been in drag (that policewoman's costume still hung in the back of his closet), but he had been expecting to look ridiculous. That wasn't the result at all. Sadayo was an excellent seamstress, and she had altered her spare maid's outfit to fit him perfectly.
Though no one was going to confuse Akira for an actual woman (he was too tall, even without any kind of heels), he didn't look too bad. Especially with the double D's he was sporting, courtesy of the bra and breast forms Sadayo had bought for him. His girlfriend had been walking on air as she had inspected him head to toe afterward. It might have led to some interesting times between them, but they were running late for their appointment. Sadayo had hurriedly changed into her own maid's outfit, and together they had gotten into her car and headed toward the client's house.
Akira took the proffered tube and flipped down the visor on the passenger's seat. His reflection stared back at him. Fairly normal looking so long as he didn't look at his neck, where a black lace ribbon was tied. Akira twisted the bottom of the lipstick tube until it rose out of the casing. He brought it to his lips, pausing for a moment as he realized that the soft pink substance had touched his girlfriend's lips only moments before. Akira wasn't exactly excited to put it on, but he couldn't help noticing that Sadayo was splitting her attention between him and the road. Wanting to make his girlfriend happy, Akira applied the pink lipstick to his lips just as Sadayo had earlier.
Sadayo grinned as Akira handed back the lipstick. His girlfriend was definitely getting a kick out of it, at least. That was something. Sadayo hummed happily as she pulled up to the curb of a large, gated house. Akira looked out the window, thinking that the client had to be pretty wealthy to own a house like this.
"Is this the place?" Akira asked quietly.
"Yep. Want to go over a few more ground rules before we go in?" Sadayo replied as she put the car in park, reaching for her purse once more.
"Sure." Akira said easily, thinking that sounded like a good idea.
They had discussed this days beforehand, but they hadn't gotten into the particulars of Akira's involvement. Akira had let it be known that he was fine with Sadayo going as far as she wanted to with the client, a man named Hideji Takeda. It was a stipulation that put power over the proceedings mostly in his girlfriend's hands, and (naturally) she had no problem with that. Sadayo had a good grasp of what Akira liked, and he trusted his girlfriend completely.
"Alright. Are you okay with a little teasing from either of us? I can imagine he's going to want to do some of that, but I can text him not to." Sadayo prompted, taking out her phone.
"Well, what counts as teasing, exactly?" Akira asked, gulping slightly.
"Hmm. Let's say that I happen to let slip that you're wearing my panties." Sadayo said wickedly, raising her eyebrows at him.
Akira's cock hardened at Sadayo's words. He was indeed wearing her panties tonight. It had been the price for asking Sadayo to refrain from wearing any of her own. The idea of this Takeda guy flipping up her skirt and having easy access to his girlfriend's pussy was explosively hot. Sadayo had protested that wearing a short skirt without panties on was embarrassing, so Akira would have to do something equally embarrassing in return.
Sadayo glanced down at Akira's skirt and noticed the obvious bulge there. His girlfriend ran her hands over the front of Akira's skirt and giggled as Akira squirmed slightly in the passenger's seat. The feeling of Sadayo's delicate hands running over the thin, lacy fabric over his cock was amazing.
"That's a yes on the teasing, then. What about showing him some respect as his maid? You don't have to call him Master like I will, but maybe you should curtsy when he opens the door." Sadayo whispered huskily, clearly enjoying herself.
"That's...that's fine." Akira replied slowly, closing his eyes at the thought.
"Good. I've already told him that you want to watch the proceedings, and he's alright with that. You don't mind doing some light housework in between rounds though, right? I imagine I'll be needing some time to recover." Sadayo said with a laugh, her dark eyes twinkling.
"What kind of housework?" Akira asked lightly, opening his eyes again.
"You've seen me do it. It's nothing too strenuous. Some light dusting and laundry is probably all he'll want. Who knows, if you do a good job, he might pay you." Sadayo said teasingly.
"That's probably not necessary." Akira replied ruefully.
"Hey, I wouldn't turn down free money, but it's up to you. Are you ready?" Sadayo asked with clear anticipation in her voice.
"I am." Akira replied, again projecting more confidence than he necessarily felt.
"I'd kiss you, but I don't want to smudge our lipstick..." Sadayo said quietly, leaning close to Akira in the car.
Akira blinked, never having encountered this problem himself before. Sadayo grinned at him again and leaned even closer. From the gleam in her eyes, Akira could tell how excited his girlfriend was.
"...Oh, who cares, we can reapply it." Sadayo said breathlessly.
Akira and Sadayo kissed for several long minutes, neither of them in any hurry to leave. They needed to make it count, anyway, if they wanted to make it worth the effort of fixing their makeup.
Sadayo rang the doorbell. Akira hung back a little, trying to distract himself from his own nervousness by checking out his girlfriend. How had he not noticed how sexy she was in her maid outfit before? Akira had seen her in it so many times by now that the novelty had worn off, or so he had thought. But the knowledge that another man was about to enjoy her charms made it seem like Akira was seeing Sadayo for the first time. His girlfriend's sexy, womanly figure was accentuated nicely by the short skirt and low cut front of her outfit. Since she wasn't wearing panties, Sadayo had also decided not to wear a bra either. Her breasts had bounced appealingly with each step she had taken to the door.
The door opened and a man appeared. Hideji Takeda was tall, fairly fit, and looked to be in his 30's. He had short dark hair, and possessed an aura of wealth and sophistication. Maybe it was because of the gray kimono he had on, or maybe it was because of the glass of sake in his hand.
Sadayo curtsied to Takeda as soon as he appeared. Akira grasped the ends of his skirt and did so as well, dipping respectfully to the man in front of them. His curtsy looked nothing like Sadayo's immaculate one, but then, Akira certainly hadn't practiced the motion before. Regardless, Takeda smiled at both of them.
"Hello, Master." Kawakami said, greeting the man in a cloyingly sweet tone.
"Kawakami-kun! It's great to see you again." Takeda declared, spreading his arms wide.
Sadayo stepped forward and hugged Takeda, who hugged her back. Akira watched where the man's free hand went, but Takeda contented himself by keeping it on Sadayo's lower back. It seemed the man wasn't so crass as to grab Sadayo's ass then and there. Their hug ended and Takeda moved aside to allow Sadayo to enter. Akira stepped up to the door but didn't go inside quite yet. He hadn't been invited in, after all. Takeda checked him out for a second or two before grinning at Akira.
"So you're her boyfriend, then? Nice to meet you, Akira-chan." Takeda said with a laugh.
Akira's cheeks reddened and his eyebrows rose slightly at the honorific he had been assigned, but he couldn't complain. He was wearing a maid's outfit, after all. In lieu of a bow or a handshake (neither of which felt appropriate with the clothes he had on), Akira curtsied once more, thinking that he had at least escaped a hug.
"Nice to meet you, Takeda-san." Akira replied quietly, stepping into the man's house.
From outside, the house had looked Western, but it was a totally different story on the inside. There were sliding doors along the walls, and the floor was made of tatami mats. In addition to that, it seemed as though Hideji Takeda was a patron of the Japanese arts. A number of old Ukiyo-e paintings and framed calligraphy pieces hung from the walls. There were several bonsai trees that Akira could see, and there was even a ceremonial sheathed katana in the corner of the room next to the entryway. It might have even been real, considering how wealthy this man clearly was.
Sadayo had taken off her black stilettos. She waited for Akira to take off his shoes and place them by the entryway, and as soon as he was done, she took a hold of his hand. Akira was privately grateful to have his girlfriend's support. Sadayo smiled at him and led Akira further down the hall with Takeda following behind. Akira found it uncomfortable to have the man behind them. His skirt suddenly seemed way too short, even as he knew that Takeda was almost certainly checking out Sadayo's butt and not his.
Their destination turned out to be the kitchen. The kitchen was large and modern and featured a bar that connected it and the dining room beside it. The bar had many liquor bottles resting on top of it, with different kinds of glasses stacked neatly and several tall stools lined up on the opposite end. Sadayo led Akira there. She sat down on a stool, with Akira doing likewise beside her.
Takeda walked over to the kitchen side of the bar and downed his sake glass in one gulp. He then set the glass down and got to work preparing drinks for each of them. Akira watched the man's experienced motions, thinking that Takeda had likely been a bartender at some point in the past. In no time at all, he had poured himself a new glass of sake and had prepared two fancy umbrella drinks for Sadayo and Akira.
"Here you go, ladies." Takeda said with a laugh as he offered them both their drinks.
They accepted their drinks, Sadayo giggling while Akira blushed. The teasing had already begun. Akira was no expert on liquor, so he had no idea how Takeda had managed to keep the blue-colored liquor on the bottom from mixing with the pink-colored liquor on top. All Akira knew was that this was the kind of drink only a girl would order. Akira sipped it regardless, hoping the alcohol would loosen him up a little.
"I was pretty surprised when I got your call, Kawakami-kun. I thought you quit that job months ago." Takeda said politely, beginning the conversation.
"I did. They let me keep the outfits, though." Sadayo replied with a grin.
"Ah. From what you've said, I'm hoping you've reconsidered your stance on certain things." Takeda said with hope evident in his voice.
Sadayo laughed and set her glass down. She turned to Akira and leaned close to whisper in his ear.
"He's talking about his many, many attempts to offer me money for sex. I always turned him down, though." Sadayo explained in a carrying whisper.
"Indeed she did. Of course, that was before she got a boyfriend with such interesting tastes." Takeda stated with a laugh, looking over at Akira.
Akira blushed again, wondering just how much Sadayo had told Takeda. Filling the man in with some of the details was unavoidable, of course, and his girlfriend had offered to let Akira read her texts with him, which he had. He hadn't been present for every phone call between the two of them, however.
"So, Kawakami-kun. Shall we negotiate a little?" Takeda asked leadingly after a moment, returning his attention to Sadayo.
"Hey, I'm not doing this for the money." Sadayo protested good-naturedly, notably not turning down his offer outright.
"Oh, you know just how to bargain, Kawakami-kun. How about...30,000 for the night?" Takeda offered, setting his empty sake glass down.
Akira blinked at the man's easy offer. That was six times what he had given Sadayo for showing up at his house during the early part of their relationship. Of course, she had done nothing more than clean his attic bedroom.
"30,000, huh?" Sadayo replied coolly, neither accepting nor declining his offer as she leaned forward a little more on her stool.
Takeda glanced down at her cleavage and (perhaps unconsciously) licked his lips slightly. If he hadn't realized that Sadayo wasn't wearing a bra before, he knew it now. The man was very, very into his girlfriend, that much was clear. Takeda looked back at her face once again and appeared to get serious.
"50,000. But I get to have you as many times as I want tonight." Takeda said firmly.
"Oh my. What should I do, Akira?" Sadayo asked in a seemingly innocent tone, looking over at him.
Akira's cock hardened as soon as the man had mentioned his additional stipulation. How many times was Takeda planning to fuck his girlfriend? And all while her boyfriend watched, dressed submissively in a maid's outfit. The thought was explosively hot, and Akira knew immediately what his answer was.
"Do it. Please." Akira said quietly, gulping.
"If that's what you want. But maybe you should ask him, too." Sadayo said wickedly, the gleam returning to her eyes.
Akira's blush deepened as he looked over at Takeda. The man's eyebrows were quite high as he regarded Akira in his maid outfit. Takeda likely couldn't understand why Akira would intentionally demean himself like this, but he was nevertheless being entertained by the proceedings.
"Please sleep with my girlfriend, Takeda-san." Akira asked him in a respectful tone.
"I'd love to, Akira-chan." Takeda replied with a very amused laugh.
Takeda kept laughing as he came around from behind the bar. Akira could only watch as Takeda bent down and embraced Sadayo, kissing her deeply. His girlfriend embraced him back, seeming to melt into the man's arms. She was not unattracted to him, clearly. After a few seconds of this, Takeda put one arm beneath Sadayo's legs and lifted her up in a princess carry. Takeda then carried her out of the room with Sadayo giggling in his arms. Akira followed in a daze, his cock as hard as it had ever been in his life.
Takeda dropped Sadayo onto the large, king-sized bed in his room and untied his kimono. He was wearing a pair of dark gray boxers, and from the bulge there, the man was just as hard as Akira was. Akira wasn't sure what to do as he watched. Standing seemed awkward and there was nowhere to sit, so he decided to simply settle down on the floor on his knees next to the bed only a few feet away from them.
Sadayo extended a stocking-clad foot and rubbed Takeda's cock slowly through his boxers. The man's cock gave an extra throb at this, and Sadayo glanced over at where Akira was kneeling. Their eyes met for a few seconds. Perhaps she was checking with him one last time? If so, Akira wanted to make his feelings clear. He nodded at Sadayo, who grinned at him before turning her attention back to the man who was going to fuck her.
Takeda was watching Sadayo on the bed and seemed to notice something. He grabbed Sadayo's ankle gently and raised it higher, causing her skirt to rise. He chuckled to himself at the sight.
"No panties, Kawakami-kun? Do you always forgo them when you're working?" Takeda asked with interest, having seen the truth for himself.
"Of course not. Akira wanted me to skip them tonight, that's all." Sadayo answered honestly, not making any attempt to cover herself.
"Is that so?" Takeda asked again as he pulled down his boxers.
Takeda's hardened cock came free and Akira couldn't help but be impressed. The man's cock was easily longer and thicker than Akira's, and from the quick intake of breath he heard from Sadayo, his girlfriend was just as impressed.
"I told my boyfriend to put them on instead." Sadayo confessed wickedly, giggling.
The man glanced over at Akira and laughed loudly. Akira blushed again, embarrassed even as he realized Sadayo was attempting to keep him involved. His cock was still as hard as a rock even while his girlfriend's white lace panties constrained it.
"I hope you're enjoying yourself, Akira-chan. I'll make sure Kawakami-kun has fun, too." Takeda promised as he climbed onto the bed.
Takeda flipped up Sadayo's skirt and tucked it out of the way. He was going to fuck Sadayo with her maid outfit on, it seemed. Sadayo blushed slightly for the first time as she spread her legs in front of him, giving the man a clear view of her hairless pussy. Sadayo always kept herself hairless there, perhaps because it made her feel younger. Her pussy was quite wet already. Akira couldn't help wondering whether she was that attracted to Takeda or whether teasing her boyfriend so thoroughly had gotten her excited. Maybe it was both. If the second part was true, then Akira could play into that a little bit.
"I'm definitely going to enjoy this." Takeda said appreciatively as he brought himself next to Sadayo, positioning his cock at the entrance to her pussy.
Takeda pushed his cock into Sadayo's already-wet pussy and drove it all the way inside, letting out a satisfied grunt as he did so. His girlfriend arched her back and let out a gasp, reacting to the sensation of being penetrated by a larger cock than she was used to. Akira rubbed himself slowly over the skirt on his outfit as he took in the sight in front of him. He didn't want to cum until the very end, however. Previous experience told him that it was always better if he held himself back as long as possible.
Takeda kept his cock all the way inside Sadayo's tight pussy, clearly enjoying the sensation of having claimed her. He then reached out with both hands and pulled down the low-cut front of Sadayo's maid outfit. Without a bra there to keep them in check, her beautiful white breasts spilled out over it, and Takeda wasted no time before fondling them with both hands.
"I've wanted to do this for a long time, Kawakami-kun." Takeda said, sounding quite happy indeed.
"Then...you should thank Akira for giving you the chance." Sadayo replied breathily, continuing to keep her boyfriend involved.
"Thank you, Akira-chan." Takeda said swiftly as he started to move, not bothering to look over at him.
"I should be thanking you for pleasuring my girlfriend, Takeda-san." Akira stated very respectfully, not for the man's sake but for Sadayo's.
Sadayo gave a surprised glance at Akira and giggled. She was clearly getting something out of having her boyfriend kowtow to the man fucking her. Akira smiled slightly in return. Increasing his girlfriend's enjoyment was worth the embarrassment Akira was putting himself through. It was close, though.
From the way Takeda began fucking Sadayo with slow, rhythmic thrusts, he had taken Akira's words to heart. For the first time, Akira reflected on the fact that the "bull" in this kind of situation had a lot of responsibility. Sure, he was getting quite a bit of enjoyment out of fucking a beautiful woman, but it was also incumbent on him to provide the other two people with heaps of pleasure, though of a differing kind. Akira couldn't help but feel a little bit of gratitude toward the man busy pleasuring his girlfriend; this whole thing wouldn't work without his efforts.
The older man was indeed working hard. Even as Takeda maintained the steady rhythm of his thrusts, he kept his hands on Sadayo's soft breasts. Akira watched, spellbound, as Takeda skillfully stimulated his girlfriend's sensitive nipples, rolling and pinching them between his fingers.
The result was that Sadayo began letting out quietly pleasurable cries that crested each time Takeda drove his cock all the way inside her. Akira watched as Sadayo wrapped her long, stockinged legs around the man, implicitly trying to draw his cock deeper. His girlfriend was getting into it far more quickly than usual. She might have been experiencing sensations that Akira's smaller cock couldn't give her. But that probably wasn't the whole story. Sadayo kept glancing over at Akira every few seconds. As much as she was evidently enjoying herself, she didn't seem to want to forget that Akira was there.
Akira wasn't certain what Sadayo wanted, but he reached out and took hold of her hand, trying to convey his feelings. Sadayo held his hand tightly and smiled at him, letting out appealingly sexual cries every second or two as she was fucked by Takeda.
"How does it feel?" Akira asked intently.
"Amazing. Absolutely amazing." Sadayo answered rapidly, closing her eyes in satisfaction.
"Is it better than when we do it?" Akira asked quietly, knowing the answer but wanting to hear it from his girlfriend.
Sadayo didn't answer at first. She was silent for a few seconds, aside from the small cries that she couldn't help but make after every thrust from the man fucking her. Takeda, for his part, was keeping himself out of their conversation for the moment. Sadayo then opened her eyes and looked at Akira for a moment before smiling at him.
"Way better. But part of it's because I love having you here watching me." Sadayo answered happily, sounding entirely honest.
Akira's cock gave an extra throb as he heard the confirmation he was looking for. There was something particularly hot about the knowledge that another man was indeed doing a better job of satisfying his girlfriend than he ever could. Although, Akira could certainly do his part by watching her as she wished. He squeezed her hand and smiled at Sadayo, who smiled back.
"I'm getting close. Watch me cum." Sadayo instructed breathily, too distracted to bother phrasing her words as a request.
Even though Takeda wasn't speaking, he had clearly been listening. Hearing Sadayo say that she was getting close to cumming made him increase the speed of his thrusts. Sadayo began letting out the particular kind of cries that Akira recognized. His girlfriend only sounded like that when she was on the cusp of an orgasm.
Sadayo arched her back on the bed and came hard. The proof was the way her grip on Akira's hand became crushingly tight. Akira couldn't help but wince. He didn't know Sadayo had that kind of strength. Takeda, who must have felt the wonderful sensation of Sadayo's silky pussy tightening around his cock, drove it all the way inside her and let out a series of very satisfied grunts. Akira's cock throbbed after each grunt he heard, knowing that each one meant a spurt of cum was being shot into his girlfriend's pussy.
Sadayo's grip loosened as she came down from her climax. Takeda lowered himself closer to Sadayo and began kissing her softly. Sadayo kissed him back, and after a few seconds, Akira saw her open her lips slightly to accept his tongue. Akira knew how pleasant that kind of post-coital kiss could be, only instead of partaking in it himself, he was in the position of watching his girlfriend share it with another man. Akira didn't mind, though. Takeda was the one who had given her an orgasm, after all.
Akira continued to hold her hand regardless, and after a minute or two of kissing Takeda, Sadayo broke off their kiss. She looked over at Akira and smiled, seeing him still kneeling there.
"That was wonderful. But I'm not as young as I was. I'm going to need a little while to recover." Sadayo said tiredly, more to Akira than Takeda.
Takeda looked to be in similar need of rest, so Akira stood up. His cock was still quite hard, but he remembered what his girlfriend had said earlier in the car. Combined with the knowledge that Sadayo enjoyed seeing him kowtow to Takeda, Akira knew what would make his girlfriend happy. It was just a question of whether he could swallow his pride sufficiently. He smoothed the skirt on his maid outfit in the seconds it took to gather himself.
"Is there any housework you need me to do...M...Master?" Akira asked quietly, tripping over the very embarrassing word at the end.
Sadayo let out a pleasurable gasp at the word and regarded him with amazement. She hadn't asked him to go that far, after all. Takeda chuckled and pushed himself off Sadayo. He laid down beside her and put his arms back behind his head, thinking for a moment before answering.
"There's some laundry you can do. Take the hamper in the closet with you. After you put it in the washer, you can start dusting the house." Takeda said with a casual air, as if Akira was really his maid.
Akira gave one of his less-than-practiced curtsies and slid open the closet door. A hamper full of clothing was in the corner of the man's very spacious closet. He picked it up and closed the door behind him.
"The washer is in the back of the house. Take the entryway past the kitchen and you'll see it." Sadayo called out helpfully, having done the man's laundry in the past, after all.
Akira nodded and gave his girlfriend a small wave to show that he had no hard feelings about this. Instead of waving back, Sadayo blew him a kiss and gave him a look of pure gratitude and tenderness. Akira couldn't help but smile at his girlfriend as he walked out of the room. The sliding door to the hallway was open, as Takeda had been carrying Sadayo, and Akira had been too dazed to close it behind him.
Akira put the clothes hamper down in the hallway and moved to slide the door shut. As he did so, he thought he heard the beginning of a conversation between Sadayo and Takeda, but he didn't try to eavesdrop. Instead, he shut the door, giving them both some privacy. Sadayo would fill Akira in if their conversation had something to do with him, anyway.
It was time to put the knowledge Akira had gained from washing all those sooty garments to good use.
Akira found the washing room easily enough. He put the man's clothes in the washer and turned it on. Having done that, Akira searched the small room until he found a feather duster. Akira then got to work dusting various areas of the house. He wandered aimlessly from room to room, admiring the excellent decor but not possessing much enthusiasm.
Takeda was even more wealthy than Akira first thought. His house was veritably filled with expensive works of art, all of which appeared quite real. He even thought he recognized a painting that might have been lent to the museum Madarame had been featured in so many months ago. Akira admired it for a moment before his attention wandered again.
When would his girlfriend be ready for another round? Sadayo hadn't said anything about when she would be, but Akira had his cellphone stowed in his apron's front pouch. She would probably text him then. With that thought in mind, Akira dusted every surface he saw. The dainty, effeminate movements this required didn't bother him too much, considering that nobody was there to see him do it.
About 15 minutes had gone by before Akira got a text. Even though he knew Sadayo wouldn't begin the second round without him, the slight possibility that she was indeed fucking Takeda as he was doing housework made Akira's cock stay hard throughout his task. But his phone buzzed as he thought it would. Akira happened to be in the kitchen when he got it, so he dropped the duster on the kitchen counter and reached for the buzzing phone stowed in his apron.
I'm ready. You're so wonderful for doing this, you know? If it's not too much, could you bring some drinks and snacks with you? There's a serving tray under the bottom counter next to the sink, I think.
Akira read the text and put his phone back where it was. He opened the indicated counter and retrieved a small circular serving tray. Akira then put the tray on the counter and opened the fridge, wondering what to bring with him. He wanted to impress his girlfriend, if possible. With that in mind, Akira found a block of cheese in the fridge and took it out. Akira also spied a few apples in a bowl on the counter.
Though it took a few extra minutes to so, Akira sliced the cheese and one of the apples into small bite-sized pieces. He then poured two glasses of sparkling water, arranged everything nicely on the tray, and walked back to the bedroom. Akira almost went right in, but he stopped himself before doing so. Instead, he knocked softly on Takeda's bedroom door and waited for permission to enter.
"Come in." The man said in the same casual tone as before.
Akira slid the door open and saw a different sight than he had been expecting. Takeda was still lying on the bed comfortably, but Sadayo was standing up. His girlfriend looked over her shoulder at Akira seductively and chose that moment to pull her maid uniform off. She had already taken off her stockings and hadn't been wearing any underwear, which meant that just like that, she was completely naked.
Both Akira and Takeda were temporarily spellbound by the sight of her fantastic body. Maybe it was because Akira had seen it a number of times before, but he was the first to recover. Akira walked over to the nightstand next to the bed and placed the serving tray there. Sadayo saw what he had brought and immediately smiled.
"See, Hideji, he would be perfect." Sadayo said in an oddly proud tone.
"Perfect for what?" Akira asked quizzically.
It did not escape Akira's notice that Sadayo had stopped referring to Takeda as "Master" and had started to use his first name. Given that Akira was the one who was adopting the role of a maid, it made sense. And privately, Akira was a little turned on to hear Sadayo referring to the man in such a familiar way.
"She wants me to hire you to be my maid. Part-time, of course." Takeda said with a laugh, reaching for a glass of sparkling water.
Akira went red at hearing that, even as his cock throbbed at the idea of being a maid to the man fucking his girlfriend. Sadayo hadn't discussed this with him yet. Perhaps she had forgotten that, because Sadayo adopted a soothing look on her face and embraced Akira. The feel of her breasts pressing against him was monumentally distracting, and that was no doubt what his girlfriend intended.
"I was going to talk to you about it later. I'm too busy teaching to be a maid anymore, but you have plenty of time on your hands, don't you? I just think it's an arrangement where everyone wins." Sadayo said brightly, continuing to hug Akira tightly.
"Everyone, huh?" Akira asked with a touch of skepticism.
"Yes! You'll make double what any other part-time job can give you. Hideji will get an obedient and respectful maid, and I'll be over here pretty often. Both of you want that, don't you?" Sadayo asked with a giggle, continuing to press her breasts against Akira in an even-more transparent way.
"I know I do." Takeda said with a laugh, sampling some of the apple slices Akira had made for him.
Sadayo reached down and slipped her hand underneath Akira's skirt. She found Akira's hardened cock and rubbed it slowly over the panties he was wearing. Akira groaned slightly, knowing that his capacity to decline to do anything Sadayo wanted was rapidly diminishing.
"You want me to come over here a lot, don't you? So Hideji can fuck me as many times as he wants?" Sadayo asked wickedly, dropping her voice at the end.
Akira almost came at his girlfriend's words. But Sadayo knew his body language very well by now and swiftly removed her hands from underneath his skirt before he could do so. She giggled and retrieved an apple slice, popping it into her mouth and waiting for Akira to answer her.
"I do want that." Akira said after a moment, unable to deny what he truly did desire.
"Then you'll be his maid?" Sadayo asked leadingly, making it clear which answer she would be most excited to hear.
"I'll...think about it." Akira replied after a moment, almost giving in then and there.
Sadayo giggled and nodded. They had been together long enough for her to know that when Akira said that, it was only a matter of time before he agreed. Sadayo gave him a very loving kiss. Akira appreciated his girlfriend's kiss, and the hint of apple on her lips made it all the more enjoyable. Sadayo then turned around and walked over to the bed where Takeda was lying down.
"Let me demonstrate what you'll get to see, then." Sadayo said in a wickedly sweet tone as she climbed onto the bed.
With a simple movement, Sadayo pulled down Takeda's boxers and freed his hardened cock once more. Akira stared at it, unable to keep himself from comparing the man's impressive cock with his own, which was still constrained by his girlfriend's lace panties. Akira then sank to his knees by the bed once again, knowing that he was in for another incredible show. Sadayo took it in her mouth, sucking the man's cock gently. It had been mostly hard beforehand, but Takeda's cock quickly grew to its full size in Sadayo's mouth, making it difficult for his girlfriend to go very far down on it.
Sadayo's eyes flicked over to Akira. Somehow he knew what his girlfriend was thinking: that she hadn't had any such difficulty with Akira's smaller cock. Still, Sadayo did her best to give Takeda a sensual blowjob, moving her beautiful lips up and down on his shaft.
"She's an amazing woman, Akira-chan. You want me to make sure she's good and satisfied from now on, right?" Takeda asked with a chuckle, clearly enjoying the blowjob he was getting.
"Yes, Master." Akira agreed readily, no longer tripping over the man's honorific.
Sadayo let out an audibly pleasurable noise at Akira's answer. The vibration made Takeda's cock give an extra throb, but Akira was too focused on his girlfriend to take much notice. For whatever reason, hearing her boyfriend answer as a maid would definitely excited her. His girlfriend reached between her legs and began touching herself lightly. Sadayo's actions certainly did not go unnoticed by either of them.
"What do you say, Akira-chan? Should I give her what she deserves?" Takeda asked good-naturedly.
"Please do, Master." Akira answered in the same respectful tone, the one he knew Sadayo loved to hear.
His girlfriend once more let out a muffled noise of excitement. Takeda's cock throbbed again, but he kept himself from cumming. Akira couldn't help but be a little impressed. He never lasted very long on the occasions when his girlfriend had given him oral sex. Akira would have cum long before now if he had been the subject of Sadayo's excellent oral skills.
Sadayo ceased her blowjob, her lips making a bit of a popping sound as she came off his cock. She kept her eyes on Akira as she crawled forward, positioning her pussy over Takeda's thick cock. Akira saw how wet she was. This time, Akira was fairly certain that she was more excited by him than by Takeda. Of course, her pussy had yet to be filled by his cock. Akira suspected that might change as soon as it was.
Takeda guided his cock head into Sadayo's pussy, and his girlfriend did the rest, sinking down onto it slowly. Once again, Sadayo let out a sound of pure satisfaction as Takeda's cock filled her tight pussy. Akira saw how perfectly their bodies seemed to be made for each other, and thought that even though he may not have meant his previous words, now he did. Akira wanted Sadayo to be as physically and emotionally satisfied as possible. He was pretty sure he had a good handle on his girlfriend's emotional needs, but now he was just as sure that Takeda was the man to handle her physical needs.
As soon as she got used to his size again, Sadayo began bouncing up and down in a slow, languid fashion on Takeda's cock in her chosen cowgirl position, moaning prettily every time she came down on his cock. Her beautiful breasts bounced freely as she did so, and Takeda grabbed them both and held them in his hands, clearly enjoying their feel. Akira knew that Sadayo loved having her breasts stimulated. Even though he wasn't the one doing it, seeing that his girlfriend was enjoying herself was the next best thing.
"F-Flip your s-skirt up, but k-keep my p-panties on. R-Rub yourself t-though them." Sadayo exclaimed suddenly to Akira after a minute or two of increasingly enjoyable sex, her voice stuttering each time she came all the way down on Takeda's cock.
Akira blinked but did as his girlfriend ordered. He tucked his skirt out of the way, ******** his panty-covered cock. It was still trying to grow to full size, and Sadayo's lace panties were still preventing it from doing so. Nevertheless, he began rubbing his cock as his girlfriend wished. The pleasurable cries Sadayo was letting out spurred his fingers, but he didn't want to cum until Sadayo did.
"A-Ask Hideji if y-you can be his m-maid. Go on." Sadayo said firmly, sounded ever closer to orgasm.
"Will you hire me as your maid, Master?" Akira asked without any hesitation, far too turned on to do anything but obey Sadayo's instructions.
"Of course, Akira-chan. You're hired." Takeda said with a short laugh, even as he was clearly getting closer to cumming himself.
"G-Good. You c-can cum when I d-do." Sadayo said with clear satisfaction in her voice, having got what she wanted.
It wasn't too long before all three of them came together. Sadayo went all the way down on Takeda's cock and let out a beautifully sensuous series of moans, her pussy spasming around Takeda's cock. The man let out the same grunts as before, with Akira's quieter ones mirroring him. But while Akira's cum shot into the panties he was wearing, Takeda let out spurt after spurt of his cum directly into Sadayo's spasming pussy.
Akira sank to the floor in sheer tiredness, his long-delayed orgasm taking the energy right out of him. It was quite a wonderful feeling to cum after holding himself back for so long. It was a minute or two before he pushed himself back up, his skirt falling down and covering his panties once more. As he rose to eye-level with the bed, he saw that Sadayo and Takeda were once again partaking in their post-coital bliss, sharing a long, deep kiss with each other.
Akira stood up and waited patiently for their kiss to end, folding his hands in front of him in the kind of submissive way that maids did in certain anime shows he had seen. If this was his new part-time job, then the faster Akira could get acclimated to his new role, the better it would be for everyone. Eventually, Sadayo and Takeda broke off their kiss and separated from each other.
"I should check on the laundry. Is there anything else that you need, Master?" Akira asked politely, getting into his role by now.
Takeda shook his head, while Sadayo reached for the other glass of sparkling water. Akira watched as Sadayo drank it down quickly. She had obviously used up a lot of her energy so far. There likely wouldn’t be any round three.
Akira could have waited for his girlfriend to finish drinking, but there would be plenty of time for them to talk later. Sadayo and Takeda wouldn't have the same chance for a while, so Akira wanted to give them some privacy while he could. Akira curtsied for the both of them and stepped out of the bedroom, sliding the door shut behind him. Before the door closed, he could see Sadayo giving him a warm smile, which he hastened to return.
Akira really did need to check the laundry. Aside from the need to wash the panties he had on, It would be a bad sign if his first act as Takeda-san's maid was to ruin his dress shirts.
Sadayo had told him that she hadn't intended on calling any of them again. It had just been a pain to delete their contact information. As it turned out, those numbers were pretty convenient to have. They made setting up tonight's activity positively easy. At least, logistically.
"We're almost there. Are you sure you want to do this? I told him that it's not a done deal until we show up at his door." Sadayo asked Akira beside her, just as she had when they had first got into her car.
"I'm sure. It would be a shame to back out now." Akira replied from the passenger's seat, trying to sound more at ease than he was.
Akira had good reason to be nervous. His girlfriend was intent on fulfilling his fantasy tonight. Akira's fantasy just happened to be a desire to see his girlfriend get fucked by another man. Which was going to happen, assuming everything went well. That was enough for anyone to feel a little nervous about, but Akira had something else to worry about. Maybe his unease was readily apparent because his girlfriend glanced over at him again.
"I think you look great in that outfit. Almost as good as I do." Sadayo said cheerfully.
Sadayo did look pretty good in her black and white maid's outfit. It wasn't exactly demure, but it wasn't meant to be. The low-cut front showed off her breasts nicely, and the black skirt on her outfit ended at mid-thigh. Sadayo wore white stockings that contrasted well with the skirt and had a pair of black stilettos on her feet. His girlfriend had her jet-black hair tied in two long ponytails and topped it all off with a fluffy white maid's cap.
The car Sadayo owned was an old, fairly beaten-up Nissan Sunny that his girlfriend had purchased for a song. From what Sadayo had told him, it always seemed on the verge of breaking down but (thankfully) never did. Though the car was of dubious quality, it had been a necessity while Sadayo had been working at her night job. After all, she could hardly board the subway in her maid's outfit, nor was changing in an alley a realistic possibility.
They came to a stoplight as they entered Azabu-Juban, the district where Sadayo's former client lived. Sadayo took advantage of the delay and flipped down her visor, revealing the mirror there. Akira watched his girlfriend rummaging in her purse until she pulled out some lipstick. Sadayo used the bright streetlights around them as illumination while she refreshed her soft-pink lipcolor in the mirror. The light turned green soon after, and Sadayo passed Akira her lipstick as she drove onward.
"Here, try this." Sadayo said in the same cheerful voice.
Offering her boyfriend her lipstick might have been a strange thing to do most of the time, but not now. Akira glanced down at what he was wearing, reminding himself that this was a two-way street. His wasn't the only fantasy that was being fulfilled tonight. Sadayo had been uncertain about engaging in the cuckolding play Akira wanted until he had asked her if he could fulfill a fantasy she had. As it turned out, Sadayo had a secret desire to see her boyfriend in drag.
Though Sadayo had couched it by claiming that the client would only let Akira watch if he was dressed as a maid as well, he had seen how enthusiastic Sadayo was at the idea. His girlfriend had happily spent hours on her sewing machine altering her spare maid's outfit to fit Akira's different physique. Sadayo had then dashed out to buy some feminine accessories that she couldn't alter from her own, like a bra and some stockings.
Akira had put on the completed outfit an hour earlier and had been surprised by how he looked. It wasn't exactly the first time he had been in drag (that policewoman's costume still hung in the back of his closet), but he had been expecting to look ridiculous. That wasn't the result at all. Sadayo was an excellent seamstress, and she had altered her spare maid's outfit to fit him perfectly.
Though no one was going to confuse Akira for an actual woman (he was too tall, even without any kind of heels), he didn't look too bad. Especially with the double D's he was sporting, courtesy of the bra and breast forms Sadayo had bought for him. His girlfriend had been walking on air as she had inspected him head to toe afterward. It might have led to some interesting times between them, but they were running late for their appointment. Sadayo had hurriedly changed into her own maid's outfit, and together they had gotten into her car and headed toward the client's house.
Akira took the proffered tube and flipped down the visor on the passenger's seat. His reflection stared back at him. Fairly normal looking so long as he didn't look at his neck, where a black lace ribbon was tied. Akira twisted the bottom of the lipstick tube until it rose out of the casing. He brought it to his lips, pausing for a moment as he realized that the soft pink substance had touched his girlfriend's lips only moments before. Akira wasn't exactly excited to put it on, but he couldn't help noticing that Sadayo was splitting her attention between him and the road. Wanting to make his girlfriend happy, Akira applied the pink lipstick to his lips just as Sadayo had earlier.
Sadayo grinned as Akira handed back the lipstick. His girlfriend was definitely getting a kick out of it, at least. That was something. Sadayo hummed happily as she pulled up to the curb of a large, gated house. Akira looked out the window, thinking that the client had to be pretty wealthy to own a house like this.
"Is this the place?" Akira asked quietly.
"Yep. Want to go over a few more ground rules before we go in?" Sadayo replied as she put the car in park, reaching for her purse once more.
"Sure." Akira said easily, thinking that sounded like a good idea.
They had discussed this days beforehand, but they hadn't gotten into the particulars of Akira's involvement. Akira had let it be known that he was fine with Sadayo going as far as she wanted to with the client, a man named Hideji Takeda. It was a stipulation that put power over the proceedings mostly in his girlfriend's hands, and (naturally) she had no problem with that. Sadayo had a good grasp of what Akira liked, and he trusted his girlfriend completely.
"Alright. Are you okay with a little teasing from either of us? I can imagine he's going to want to do some of that, but I can text him not to." Sadayo prompted, taking out her phone.
"Well, what counts as teasing, exactly?" Akira asked, gulping slightly.
"Hmm. Let's say that I happen to let slip that you're wearing my panties." Sadayo said wickedly, raising her eyebrows at him.
Akira's cock hardened at Sadayo's words. He was indeed wearing her panties tonight. It had been the price for asking Sadayo to refrain from wearing any of her own. The idea of this Takeda guy flipping up her skirt and having easy access to his girlfriend's pussy was explosively hot. Sadayo had protested that wearing a short skirt without panties on was embarrassing, so Akira would have to do something equally embarrassing in return.
Sadayo glanced down at Akira's skirt and noticed the obvious bulge there. His girlfriend ran her hands over the front of Akira's skirt and giggled as Akira squirmed slightly in the passenger's seat. The feeling of Sadayo's delicate hands running over the thin, lacy fabric over his cock was amazing.
"That's a yes on the teasing, then. What about showing him some respect as his maid? You don't have to call him Master like I will, but maybe you should curtsy when he opens the door." Sadayo whispered huskily, clearly enjoying herself.
"That's...that's fine." Akira replied slowly, closing his eyes at the thought.
"Good. I've already told him that you want to watch the proceedings, and he's alright with that. You don't mind doing some light housework in between rounds though, right? I imagine I'll be needing some time to recover." Sadayo said with a laugh, her dark eyes twinkling.
"What kind of housework?" Akira asked lightly, opening his eyes again.
"You've seen me do it. It's nothing too strenuous. Some light dusting and laundry is probably all he'll want. Who knows, if you do a good job, he might pay you." Sadayo said teasingly.
"That's probably not necessary." Akira replied ruefully.
"Hey, I wouldn't turn down free money, but it's up to you. Are you ready?" Sadayo asked with clear anticipation in her voice.
"I am." Akira replied, again projecting more confidence than he necessarily felt.
"I'd kiss you, but I don't want to smudge our lipstick..." Sadayo said quietly, leaning close to Akira in the car.
Akira blinked, never having encountered this problem himself before. Sadayo grinned at him again and leaned even closer. From the gleam in her eyes, Akira could tell how excited his girlfriend was.
"...Oh, who cares, we can reapply it." Sadayo said breathlessly.
Akira and Sadayo kissed for several long minutes, neither of them in any hurry to leave. They needed to make it count, anyway, if they wanted to make it worth the effort of fixing their makeup.
Sadayo rang the doorbell. Akira hung back a little, trying to distract himself from his own nervousness by checking out his girlfriend. How had he not noticed how sexy she was in her maid outfit before? Akira had seen her in it so many times by now that the novelty had worn off, or so he had thought. But the knowledge that another man was about to enjoy her charms made it seem like Akira was seeing Sadayo for the first time. His girlfriend's sexy, womanly figure was accentuated nicely by the short skirt and low cut front of her outfit. Since she wasn't wearing panties, Sadayo had also decided not to wear a bra either. Her breasts had bounced appealingly with each step she had taken to the door.
The door opened and a man appeared. Hideji Takeda was tall, fairly fit, and looked to be in his 30's. He had short dark hair, and possessed an aura of wealth and sophistication. Maybe it was because of the gray kimono he had on, or maybe it was because of the glass of sake in his hand.
Sadayo curtsied to Takeda as soon as he appeared. Akira grasped the ends of his skirt and did so as well, dipping respectfully to the man in front of them. His curtsy looked nothing like Sadayo's immaculate one, but then, Akira certainly hadn't practiced the motion before. Regardless, Takeda smiled at both of them.
"Hello, Master." Kawakami said, greeting the man in a cloyingly sweet tone.
"Kawakami-kun! It's great to see you again." Takeda declared, spreading his arms wide.
Sadayo stepped forward and hugged Takeda, who hugged her back. Akira watched where the man's free hand went, but Takeda contented himself by keeping it on Sadayo's lower back. It seemed the man wasn't so crass as to grab Sadayo's ass then and there. Their hug ended and Takeda moved aside to allow Sadayo to enter. Akira stepped up to the door but didn't go inside quite yet. He hadn't been invited in, after all. Takeda checked him out for a second or two before grinning at Akira.
"So you're her boyfriend, then? Nice to meet you, Akira-chan." Takeda said with a laugh.
Akira's cheeks reddened and his eyebrows rose slightly at the honorific he had been assigned, but he couldn't complain. He was wearing a maid's outfit, after all. In lieu of a bow or a handshake (neither of which felt appropriate with the clothes he had on), Akira curtsied once more, thinking that he had at least escaped a hug.
"Nice to meet you, Takeda-san." Akira replied quietly, stepping into the man's house.
From outside, the house had looked Western, but it was a totally different story on the inside. There were sliding doors along the walls, and the floor was made of tatami mats. In addition to that, it seemed as though Hideji Takeda was a patron of the Japanese arts. A number of old Ukiyo-e paintings and framed calligraphy pieces hung from the walls. There were several bonsai trees that Akira could see, and there was even a ceremonial sheathed katana in the corner of the room next to the entryway. It might have even been real, considering how wealthy this man clearly was.
Sadayo had taken off her black stilettos. She waited for Akira to take off his shoes and place them by the entryway, and as soon as he was done, she took a hold of his hand. Akira was privately grateful to have his girlfriend's support. Sadayo smiled at him and led Akira further down the hall with Takeda following behind. Akira found it uncomfortable to have the man behind them. His skirt suddenly seemed way too short, even as he knew that Takeda was almost certainly checking out Sadayo's butt and not his.
Their destination turned out to be the kitchen. The kitchen was large and modern and featured a bar that connected it and the dining room beside it. The bar had many liquor bottles resting on top of it, with different kinds of glasses stacked neatly and several tall stools lined up on the opposite end. Sadayo led Akira there. She sat down on a stool, with Akira doing likewise beside her.
Takeda walked over to the kitchen side of the bar and downed his sake glass in one gulp. He then set the glass down and got to work preparing drinks for each of them. Akira watched the man's experienced motions, thinking that Takeda had likely been a bartender at some point in the past. In no time at all, he had poured himself a new glass of sake and had prepared two fancy umbrella drinks for Sadayo and Akira.
"Here you go, ladies." Takeda said with a laugh as he offered them both their drinks.
They accepted their drinks, Sadayo giggling while Akira blushed. The teasing had already begun. Akira was no expert on liquor, so he had no idea how Takeda had managed to keep the blue-colored liquor on the bottom from mixing with the pink-colored liquor on top. All Akira knew was that this was the kind of drink only a girl would order. Akira sipped it regardless, hoping the alcohol would loosen him up a little.
"I was pretty surprised when I got your call, Kawakami-kun. I thought you quit that job months ago." Takeda said politely, beginning the conversation.
"I did. They let me keep the outfits, though." Sadayo replied with a grin.
"Ah. From what you've said, I'm hoping you've reconsidered your stance on certain things." Takeda said with hope evident in his voice.
Sadayo laughed and set her glass down. She turned to Akira and leaned close to whisper in his ear.
"He's talking about his many, many attempts to offer me money for sex. I always turned him down, though." Sadayo explained in a carrying whisper.
"Indeed she did. Of course, that was before she got a boyfriend with such interesting tastes." Takeda stated with a laugh, looking over at Akira.
Akira blushed again, wondering just how much Sadayo had told Takeda. Filling the man in with some of the details was unavoidable, of course, and his girlfriend had offered to let Akira read her texts with him, which he had. He hadn't been present for every phone call between the two of them, however.
"So, Kawakami-kun. Shall we negotiate a little?" Takeda asked leadingly after a moment, returning his attention to Sadayo.
"Hey, I'm not doing this for the money." Sadayo protested good-naturedly, notably not turning down his offer outright.
"Oh, you know just how to bargain, Kawakami-kun. How about...30,000 for the night?" Takeda offered, setting his empty sake glass down.
Akira blinked at the man's easy offer. That was six times what he had given Sadayo for showing up at his house during the early part of their relationship. Of course, she had done nothing more than clean his attic bedroom.
"30,000, huh?" Sadayo replied coolly, neither accepting nor declining his offer as she leaned forward a little more on her stool.
Takeda glanced down at her cleavage and (perhaps unconsciously) licked his lips slightly. If he hadn't realized that Sadayo wasn't wearing a bra before, he knew it now. The man was very, very into his girlfriend, that much was clear. Takeda looked back at her face once again and appeared to get serious.
"50,000. But I get to have you as many times as I want tonight." Takeda said firmly.
"Oh my. What should I do, Akira?" Sadayo asked in a seemingly innocent tone, looking over at him.
Akira's cock hardened as soon as the man had mentioned his additional stipulation. How many times was Takeda planning to fuck his girlfriend? And all while her boyfriend watched, dressed submissively in a maid's outfit. The thought was explosively hot, and Akira knew immediately what his answer was.
"Do it. Please." Akira said quietly, gulping.
"If that's what you want. But maybe you should ask him, too." Sadayo said wickedly, the gleam returning to her eyes.
Akira's blush deepened as he looked over at Takeda. The man's eyebrows were quite high as he regarded Akira in his maid outfit. Takeda likely couldn't understand why Akira would intentionally demean himself like this, but he was nevertheless being entertained by the proceedings.
"Please sleep with my girlfriend, Takeda-san." Akira asked him in a respectful tone.
"I'd love to, Akira-chan." Takeda replied with a very amused laugh.
Takeda kept laughing as he came around from behind the bar. Akira could only watch as Takeda bent down and embraced Sadayo, kissing her deeply. His girlfriend embraced him back, seeming to melt into the man's arms. She was not unattracted to him, clearly. After a few seconds of this, Takeda put one arm beneath Sadayo's legs and lifted her up in a princess carry. Takeda then carried her out of the room with Sadayo giggling in his arms. Akira followed in a daze, his cock as hard as it had ever been in his life.
Takeda dropped Sadayo onto the large, king-sized bed in his room and untied his kimono. He was wearing a pair of dark gray boxers, and from the bulge there, the man was just as hard as Akira was. Akira wasn't sure what to do as he watched. Standing seemed awkward and there was nowhere to sit, so he decided to simply settle down on the floor on his knees next to the bed only a few feet away from them.
Sadayo extended a stocking-clad foot and rubbed Takeda's cock slowly through his boxers. The man's cock gave an extra throb at this, and Sadayo glanced over at where Akira was kneeling. Their eyes met for a few seconds. Perhaps she was checking with him one last time? If so, Akira wanted to make his feelings clear. He nodded at Sadayo, who grinned at him before turning her attention back to the man who was going to fuck her.
Takeda was watching Sadayo on the bed and seemed to notice something. He grabbed Sadayo's ankle gently and raised it higher, causing her skirt to rise. He chuckled to himself at the sight.
"No panties, Kawakami-kun? Do you always forgo them when you're working?" Takeda asked with interest, having seen the truth for himself.
"Of course not. Akira wanted me to skip them tonight, that's all." Sadayo answered honestly, not making any attempt to cover herself.
"Is that so?" Takeda asked again as he pulled down his boxers.
Takeda's hardened cock came free and Akira couldn't help but be impressed. The man's cock was easily longer and thicker than Akira's, and from the quick intake of breath he heard from Sadayo, his girlfriend was just as impressed.
"I told my boyfriend to put them on instead." Sadayo confessed wickedly, giggling.
The man glanced over at Akira and laughed loudly. Akira blushed again, embarrassed even as he realized Sadayo was attempting to keep him involved. His cock was still as hard as a rock even while his girlfriend's white lace panties constrained it.
"I hope you're enjoying yourself, Akira-chan. I'll make sure Kawakami-kun has fun, too." Takeda promised as he climbed onto the bed.
Takeda flipped up Sadayo's skirt and tucked it out of the way. He was going to fuck Sadayo with her maid outfit on, it seemed. Sadayo blushed slightly for the first time as she spread her legs in front of him, giving the man a clear view of her hairless pussy. Sadayo always kept herself hairless there, perhaps because it made her feel younger. Her pussy was quite wet already. Akira couldn't help wondering whether she was that attracted to Takeda or whether teasing her boyfriend so thoroughly had gotten her excited. Maybe it was both. If the second part was true, then Akira could play into that a little bit.
"I'm definitely going to enjoy this." Takeda said appreciatively as he brought himself next to Sadayo, positioning his cock at the entrance to her pussy.
Takeda pushed his cock into Sadayo's already-wet pussy and drove it all the way inside, letting out a satisfied grunt as he did so. His girlfriend arched her back and let out a gasp, reacting to the sensation of being penetrated by a larger cock than she was used to. Akira rubbed himself slowly over the skirt on his outfit as he took in the sight in front of him. He didn't want to cum until the very end, however. Previous experience told him that it was always better if he held himself back as long as possible.
Takeda kept his cock all the way inside Sadayo's tight pussy, clearly enjoying the sensation of having claimed her. He then reached out with both hands and pulled down the low-cut front of Sadayo's maid outfit. Without a bra there to keep them in check, her beautiful white breasts spilled out over it, and Takeda wasted no time before fondling them with both hands.
"I've wanted to do this for a long time, Kawakami-kun." Takeda said, sounding quite happy indeed.
"Then...you should thank Akira for giving you the chance." Sadayo replied breathily, continuing to keep her boyfriend involved.
"Thank you, Akira-chan." Takeda said swiftly as he started to move, not bothering to look over at him.
"I should be thanking you for pleasuring my girlfriend, Takeda-san." Akira stated very respectfully, not for the man's sake but for Sadayo's.
Sadayo gave a surprised glance at Akira and giggled. She was clearly getting something out of having her boyfriend kowtow to the man fucking her. Akira smiled slightly in return. Increasing his girlfriend's enjoyment was worth the embarrassment Akira was putting himself through. It was close, though.
From the way Takeda began fucking Sadayo with slow, rhythmic thrusts, he had taken Akira's words to heart. For the first time, Akira reflected on the fact that the "bull" in this kind of situation had a lot of responsibility. Sure, he was getting quite a bit of enjoyment out of fucking a beautiful woman, but it was also incumbent on him to provide the other two people with heaps of pleasure, though of a differing kind. Akira couldn't help but feel a little bit of gratitude toward the man busy pleasuring his girlfriend; this whole thing wouldn't work without his efforts.
The older man was indeed working hard. Even as Takeda maintained the steady rhythm of his thrusts, he kept his hands on Sadayo's soft breasts. Akira watched, spellbound, as Takeda skillfully stimulated his girlfriend's sensitive nipples, rolling and pinching them between his fingers.
The result was that Sadayo began letting out quietly pleasurable cries that crested each time Takeda drove his cock all the way inside her. Akira watched as Sadayo wrapped her long, stockinged legs around the man, implicitly trying to draw his cock deeper. His girlfriend was getting into it far more quickly than usual. She might have been experiencing sensations that Akira's smaller cock couldn't give her. But that probably wasn't the whole story. Sadayo kept glancing over at Akira every few seconds. As much as she was evidently enjoying herself, she didn't seem to want to forget that Akira was there.
Akira wasn't certain what Sadayo wanted, but he reached out and took hold of her hand, trying to convey his feelings. Sadayo held his hand tightly and smiled at him, letting out appealingly sexual cries every second or two as she was fucked by Takeda.
"How does it feel?" Akira asked intently.
"Amazing. Absolutely amazing." Sadayo answered rapidly, closing her eyes in satisfaction.
"Is it better than when we do it?" Akira asked quietly, knowing the answer but wanting to hear it from his girlfriend.
Sadayo didn't answer at first. She was silent for a few seconds, aside from the small cries that she couldn't help but make after every thrust from the man fucking her. Takeda, for his part, was keeping himself out of their conversation for the moment. Sadayo then opened her eyes and looked at Akira for a moment before smiling at him.
"Way better. But part of it's because I love having you here watching me." Sadayo answered happily, sounding entirely honest.
Akira's cock gave an extra throb as he heard the confirmation he was looking for. There was something particularly hot about the knowledge that another man was indeed doing a better job of satisfying his girlfriend than he ever could. Although, Akira could certainly do his part by watching her as she wished. He squeezed her hand and smiled at Sadayo, who smiled back.
"I'm getting close. Watch me cum." Sadayo instructed breathily, too distracted to bother phrasing her words as a request.
Even though Takeda wasn't speaking, he had clearly been listening. Hearing Sadayo say that she was getting close to cumming made him increase the speed of his thrusts. Sadayo began letting out the particular kind of cries that Akira recognized. His girlfriend only sounded like that when she was on the cusp of an orgasm.
Sadayo arched her back on the bed and came hard. The proof was the way her grip on Akira's hand became crushingly tight. Akira couldn't help but wince. He didn't know Sadayo had that kind of strength. Takeda, who must have felt the wonderful sensation of Sadayo's silky pussy tightening around his cock, drove it all the way inside her and let out a series of very satisfied grunts. Akira's cock throbbed after each grunt he heard, knowing that each one meant a spurt of cum was being shot into his girlfriend's pussy.
Sadayo's grip loosened as she came down from her climax. Takeda lowered himself closer to Sadayo and began kissing her softly. Sadayo kissed him back, and after a few seconds, Akira saw her open her lips slightly to accept his tongue. Akira knew how pleasant that kind of post-coital kiss could be, only instead of partaking in it himself, he was in the position of watching his girlfriend share it with another man. Akira didn't mind, though. Takeda was the one who had given her an orgasm, after all.
Akira continued to hold her hand regardless, and after a minute or two of kissing Takeda, Sadayo broke off their kiss. She looked over at Akira and smiled, seeing him still kneeling there.
"That was wonderful. But I'm not as young as I was. I'm going to need a little while to recover." Sadayo said tiredly, more to Akira than Takeda.
Takeda looked to be in similar need of rest, so Akira stood up. His cock was still quite hard, but he remembered what his girlfriend had said earlier in the car. Combined with the knowledge that Sadayo enjoyed seeing him kowtow to Takeda, Akira knew what would make his girlfriend happy. It was just a question of whether he could swallow his pride sufficiently. He smoothed the skirt on his maid outfit in the seconds it took to gather himself.
"Is there any housework you need me to do...M...Master?" Akira asked quietly, tripping over the very embarrassing word at the end.
Sadayo let out a pleasurable gasp at the word and regarded him with amazement. She hadn't asked him to go that far, after all. Takeda chuckled and pushed himself off Sadayo. He laid down beside her and put his arms back behind his head, thinking for a moment before answering.
"There's some laundry you can do. Take the hamper in the closet with you. After you put it in the washer, you can start dusting the house." Takeda said with a casual air, as if Akira was really his maid.
Akira gave one of his less-than-practiced curtsies and slid open the closet door. A hamper full of clothing was in the corner of the man's very spacious closet. He picked it up and closed the door behind him.
"The washer is in the back of the house. Take the entryway past the kitchen and you'll see it." Sadayo called out helpfully, having done the man's laundry in the past, after all.
Akira nodded and gave his girlfriend a small wave to show that he had no hard feelings about this. Instead of waving back, Sadayo blew him a kiss and gave him a look of pure gratitude and tenderness. Akira couldn't help but smile at his girlfriend as he walked out of the room. The sliding door to the hallway was open, as Takeda had been carrying Sadayo, and Akira had been too dazed to close it behind him.
Akira put the clothes hamper down in the hallway and moved to slide the door shut. As he did so, he thought he heard the beginning of a conversation between Sadayo and Takeda, but he didn't try to eavesdrop. Instead, he shut the door, giving them both some privacy. Sadayo would fill Akira in if their conversation had something to do with him, anyway.
It was time to put the knowledge Akira had gained from washing all those sooty garments to good use.
Akira found the washing room easily enough. He put the man's clothes in the washer and turned it on. Having done that, Akira searched the small room until he found a feather duster. Akira then got to work dusting various areas of the house. He wandered aimlessly from room to room, admiring the excellent decor but not possessing much enthusiasm.
Takeda was even more wealthy than Akira first thought. His house was veritably filled with expensive works of art, all of which appeared quite real. He even thought he recognized a painting that might have been lent to the museum Madarame had been featured in so many months ago. Akira admired it for a moment before his attention wandered again.
When would his girlfriend be ready for another round? Sadayo hadn't said anything about when she would be, but Akira had his cellphone stowed in his apron's front pouch. She would probably text him then. With that thought in mind, Akira dusted every surface he saw. The dainty, effeminate movements this required didn't bother him too much, considering that nobody was there to see him do it.
About 15 minutes had gone by before Akira got a text. Even though he knew Sadayo wouldn't begin the second round without him, the slight possibility that she was indeed fucking Takeda as he was doing housework made Akira's cock stay hard throughout his task. But his phone buzzed as he thought it would. Akira happened to be in the kitchen when he got it, so he dropped the duster on the kitchen counter and reached for the buzzing phone stowed in his apron.
I'm ready. You're so wonderful for doing this, you know? If it's not too much, could you bring some drinks and snacks with you? There's a serving tray under the bottom counter next to the sink, I think.
Akira read the text and put his phone back where it was. He opened the indicated counter and retrieved a small circular serving tray. Akira then put the tray on the counter and opened the fridge, wondering what to bring with him. He wanted to impress his girlfriend, if possible. With that in mind, Akira found a block of cheese in the fridge and took it out. Akira also spied a few apples in a bowl on the counter.
Though it took a few extra minutes to so, Akira sliced the cheese and one of the apples into small bite-sized pieces. He then poured two glasses of sparkling water, arranged everything nicely on the tray, and walked back to the bedroom. Akira almost went right in, but he stopped himself before doing so. Instead, he knocked softly on Takeda's bedroom door and waited for permission to enter.
"Come in." The man said in the same casual tone as before.
Akira slid the door open and saw a different sight than he had been expecting. Takeda was still lying on the bed comfortably, but Sadayo was standing up. His girlfriend looked over her shoulder at Akira seductively and chose that moment to pull her maid uniform off. She had already taken off her stockings and hadn't been wearing any underwear, which meant that just like that, she was completely naked.
Both Akira and Takeda were temporarily spellbound by the sight of her fantastic body. Maybe it was because Akira had seen it a number of times before, but he was the first to recover. Akira walked over to the nightstand next to the bed and placed the serving tray there. Sadayo saw what he had brought and immediately smiled.
"See, Hideji, he would be perfect." Sadayo said in an oddly proud tone.
"Perfect for what?" Akira asked quizzically.
It did not escape Akira's notice that Sadayo had stopped referring to Takeda as "Master" and had started to use his first name. Given that Akira was the one who was adopting the role of a maid, it made sense. And privately, Akira was a little turned on to hear Sadayo referring to the man in such a familiar way.
"She wants me to hire you to be my maid. Part-time, of course." Takeda said with a laugh, reaching for a glass of sparkling water.
Akira went red at hearing that, even as his cock throbbed at the idea of being a maid to the man fucking his girlfriend. Sadayo hadn't discussed this with him yet. Perhaps she had forgotten that, because Sadayo adopted a soothing look on her face and embraced Akira. The feel of her breasts pressing against him was monumentally distracting, and that was no doubt what his girlfriend intended.
"I was going to talk to you about it later. I'm too busy teaching to be a maid anymore, but you have plenty of time on your hands, don't you? I just think it's an arrangement where everyone wins." Sadayo said brightly, continuing to hug Akira tightly.
"Everyone, huh?" Akira asked with a touch of skepticism.
"Yes! You'll make double what any other part-time job can give you. Hideji will get an obedient and respectful maid, and I'll be over here pretty often. Both of you want that, don't you?" Sadayo asked with a giggle, continuing to press her breasts against Akira in an even-more transparent way.
"I know I do." Takeda said with a laugh, sampling some of the apple slices Akira had made for him.
Sadayo reached down and slipped her hand underneath Akira's skirt. She found Akira's hardened cock and rubbed it slowly over the panties he was wearing. Akira groaned slightly, knowing that his capacity to decline to do anything Sadayo wanted was rapidly diminishing.
"You want me to come over here a lot, don't you? So Hideji can fuck me as many times as he wants?" Sadayo asked wickedly, dropping her voice at the end.
Akira almost came at his girlfriend's words. But Sadayo knew his body language very well by now and swiftly removed her hands from underneath his skirt before he could do so. She giggled and retrieved an apple slice, popping it into her mouth and waiting for Akira to answer her.
"I do want that." Akira said after a moment, unable to deny what he truly did desire.
"Then you'll be his maid?" Sadayo asked leadingly, making it clear which answer she would be most excited to hear.
"I'll...think about it." Akira replied after a moment, almost giving in then and there.
Sadayo giggled and nodded. They had been together long enough for her to know that when Akira said that, it was only a matter of time before he agreed. Sadayo gave him a very loving kiss. Akira appreciated his girlfriend's kiss, and the hint of apple on her lips made it all the more enjoyable. Sadayo then turned around and walked over to the bed where Takeda was lying down.
"Let me demonstrate what you'll get to see, then." Sadayo said in a wickedly sweet tone as she climbed onto the bed.
With a simple movement, Sadayo pulled down Takeda's boxers and freed his hardened cock once more. Akira stared at it, unable to keep himself from comparing the man's impressive cock with his own, which was still constrained by his girlfriend's lace panties. Akira then sank to his knees by the bed once again, knowing that he was in for another incredible show. Sadayo took it in her mouth, sucking the man's cock gently. It had been mostly hard beforehand, but Takeda's cock quickly grew to its full size in Sadayo's mouth, making it difficult for his girlfriend to go very far down on it.
Sadayo's eyes flicked over to Akira. Somehow he knew what his girlfriend was thinking: that she hadn't had any such difficulty with Akira's smaller cock. Still, Sadayo did her best to give Takeda a sensual blowjob, moving her beautiful lips up and down on his shaft.
"She's an amazing woman, Akira-chan. You want me to make sure she's good and satisfied from now on, right?" Takeda asked with a chuckle, clearly enjoying the blowjob he was getting.
"Yes, Master." Akira agreed readily, no longer tripping over the man's honorific.
Sadayo let out an audibly pleasurable noise at Akira's answer. The vibration made Takeda's cock give an extra throb, but Akira was too focused on his girlfriend to take much notice. For whatever reason, hearing her boyfriend answer as a maid would definitely excited her. His girlfriend reached between her legs and began touching herself lightly. Sadayo's actions certainly did not go unnoticed by either of them.
"What do you say, Akira-chan? Should I give her what she deserves?" Takeda asked good-naturedly.
"Please do, Master." Akira answered in the same respectful tone, the one he knew Sadayo loved to hear.
His girlfriend once more let out a muffled noise of excitement. Takeda's cock throbbed again, but he kept himself from cumming. Akira couldn't help but be a little impressed. He never lasted very long on the occasions when his girlfriend had given him oral sex. Akira would have cum long before now if he had been the subject of Sadayo's excellent oral skills.
Sadayo ceased her blowjob, her lips making a bit of a popping sound as she came off his cock. She kept her eyes on Akira as she crawled forward, positioning her pussy over Takeda's thick cock. Akira saw how wet she was. This time, Akira was fairly certain that she was more excited by him than by Takeda. Of course, her pussy had yet to be filled by his cock. Akira suspected that might change as soon as it was.
Takeda guided his cock head into Sadayo's pussy, and his girlfriend did the rest, sinking down onto it slowly. Once again, Sadayo let out a sound of pure satisfaction as Takeda's cock filled her tight pussy. Akira saw how perfectly their bodies seemed to be made for each other, and thought that even though he may not have meant his previous words, now he did. Akira wanted Sadayo to be as physically and emotionally satisfied as possible. He was pretty sure he had a good handle on his girlfriend's emotional needs, but now he was just as sure that Takeda was the man to handle her physical needs.
As soon as she got used to his size again, Sadayo began bouncing up and down in a slow, languid fashion on Takeda's cock in her chosen cowgirl position, moaning prettily every time she came down on his cock. Her beautiful breasts bounced freely as she did so, and Takeda grabbed them both and held them in his hands, clearly enjoying their feel. Akira knew that Sadayo loved having her breasts stimulated. Even though he wasn't the one doing it, seeing that his girlfriend was enjoying herself was the next best thing.
"F-Flip your s-skirt up, but k-keep my p-panties on. R-Rub yourself t-though them." Sadayo exclaimed suddenly to Akira after a minute or two of increasingly enjoyable sex, her voice stuttering each time she came all the way down on Takeda's cock.
Akira blinked but did as his girlfriend ordered. He tucked his skirt out of the way, ******** his panty-covered cock. It was still trying to grow to full size, and Sadayo's lace panties were still preventing it from doing so. Nevertheless, he began rubbing his cock as his girlfriend wished. The pleasurable cries Sadayo was letting out spurred his fingers, but he didn't want to cum until Sadayo did.
"A-Ask Hideji if y-you can be his m-maid. Go on." Sadayo said firmly, sounded ever closer to orgasm.
"Will you hire me as your maid, Master?" Akira asked without any hesitation, far too turned on to do anything but obey Sadayo's instructions.
"Of course, Akira-chan. You're hired." Takeda said with a short laugh, even as he was clearly getting closer to cumming himself.
"G-Good. You c-can cum when I d-do." Sadayo said with clear satisfaction in her voice, having got what she wanted.
It wasn't too long before all three of them came together. Sadayo went all the way down on Takeda's cock and let out a beautifully sensuous series of moans, her pussy spasming around Takeda's cock. The man let out the same grunts as before, with Akira's quieter ones mirroring him. But while Akira's cum shot into the panties he was wearing, Takeda let out spurt after spurt of his cum directly into Sadayo's spasming pussy.
Akira sank to the floor in sheer tiredness, his long-delayed orgasm taking the energy right out of him. It was quite a wonderful feeling to cum after holding himself back for so long. It was a minute or two before he pushed himself back up, his skirt falling down and covering his panties once more. As he rose to eye-level with the bed, he saw that Sadayo and Takeda were once again partaking in their post-coital bliss, sharing a long, deep kiss with each other.
Akira stood up and waited patiently for their kiss to end, folding his hands in front of him in the kind of submissive way that maids did in certain anime shows he had seen. If this was his new part-time job, then the faster Akira could get acclimated to his new role, the better it would be for everyone. Eventually, Sadayo and Takeda broke off their kiss and separated from each other.
"I should check on the laundry. Is there anything else that you need, Master?" Akira asked politely, getting into his role by now.
Takeda shook his head, while Sadayo reached for the other glass of sparkling water. Akira watched as Sadayo drank it down quickly. She had obviously used up a lot of her energy so far. There likely wouldn’t be any round three.
Akira could have waited for his girlfriend to finish drinking, but there would be plenty of time for them to talk later. Sadayo and Takeda wouldn't have the same chance for a while, so Akira wanted to give them some privacy while he could. Akira curtsied for the both of them and stepped out of the bedroom, sliding the door shut behind him. Before the door closed, he could see Sadayo giving him a warm smile, which he hastened to return.
Akira really did need to check the laundry. Aside from the need to wash the panties he had on, It would be a bad sign if his first act as Takeda-san's maid was to ruin his dress shirts.
