Work Header

Peeking Under the Skirt of the Blue Sky

Work Text:

Before she left the school, the Lord of the Pleasure Seekers sought out Tsugumi Aozora. She had heard the rumors, and wanted to see if they were true. If they were, she was going to get laid. It was rare for a day to go by without her having sex with someone, and a crossdresser would be a great story to add to her litany of stories over the years. The gap there was enough to make her wet at the very thought of it.

She walked to the equipment shed behind the school. Tsugumi was standing there, looking for all the world like a beautiful girl. The Lord approached, holding her hand out and asking for the money first. She didn’t think of it as prostitution. She thought of it as a commission. Artists get paid for what they’re good at, and what she was good at was bringing people to orgasm. All of her holes and every soft, fleshy part of her body was a tool for making dicks splurt out what they’d been holding up, a feeling that eclipsed even the best masturbation. That kind of talent can’t be found anywhere.

“Money first, then you show me the goods,” said the Lord.

Tsugumi handed over a wad of bills. This was more than the Lord usually got paid for her sexual services. With this, she could easily spend the whole hour playing around. After the money changed hands, Tsugumi’s skirt was raised to reveal an erect cock emerging from a pair of panties. When at home, it was contained in either a pair of boxer briefs or nothing at all, but in public it was a pair of sky-blue panties much like these. Tsugumi lowered the underwear, letting the cock and balls breathe free.

“Thank you. It’s, like, so hard studying for all these finals. I mean, I’m going to get good grades anyway, but sometimes I just want to relax and suck a cock, you know? I’ve heard yours is one of the biggest in town,” said the Lord of the Pastimers.

“You’re free to do as you please with it, as long as you swallow,” said Tsugumi.

“Are you silly? I always swallow,” said Tsugumi. “Every meal is served with a topping of cum in my belly. Though I’ve never had cum from an androgynous dick like yours.”

“I assure you, it’s quite thick,” said Tsugumi.

There, in the shadow of the setting sun, the sounds of slurping could be heard. Tsugumi was getting sucked off, the Lord of the Pastimers using her expert fellatio technique to massage Tsugumi’s cock and balls. This was meant to be a quickie, and Tsugumi had a serious case of blue balls after spending all day spying on the girls’ school. One girl in particular stood out from the crowd, but her loser friends kept getting in the way. Soon, Tsugumi would find a way to claim her, after busting a nut with this surprisingly smart gal.

“Can you believe I almost had a boy from my old class ask to have sex with me? I think he might’ve blown me anyway, I’m just so cute,” said Tsugumi. “I prefer girls, and you’re the trashiest, sluttiest girl I know.”

“You can stop praising me,” said the Lord of the Pastimers. “I heard that the club your crush is in, like, recently invented some sort of sex android. She was hitting on the teachers around your school.”

“I have to investigate this further,” said Tsugumi. “Oh, damn! I’m gonna cum! Swallow every drop.”

Tsugumi came inside the Lord of Pastimers’ mouth, filling her cheeks with sticky cum. She stayed attached to his dick, sucking on it like a lollipop until every last drop of semen had emptied from Tsugumi’s balls. The Lord swallowed the salty, sticky cum, and let out a loud cum burp. She kindly thanked Tsugumi, and went off in search of the next man to fuck for the night. As for Tsugumi, the Pastimers Club was the next target. Especially with the news of that sex robot.

After Hanako insinuated that Olivia’s brother was fat enough to be a sumo wrestler, Olivia convinced Hanako that the Pastimers Club had to try female sumo wrestling for their next game. The problem was that none of them were plump enough to be sumo wrestlers. So Olivia, trying to fake her knowledge of foreign culture, took them to McDonald’s, the most quintessential of American restaurants. After ordering large meals for all of them, they set about eating on Hanako’s dime, with plans to return to school in the afternoon and attempt sumo.

Kasumi had ordered a milkshake, which Hanako swiped away from her and started drinking herself, leaving Kasumi to take Hanako’s Coke. This unofficial exchange had happened out of Hanako’s jealousy and misguided belief that if Kasumi drank this milkshake, her already large breasts would get even bigger. She, of the AA Cup, could not stand such a thing. Olivia was more focused on the food than the drinks, and ended up eating most of everyone’s meals.

The plan had not worked as intended. Kasumi said her bra was feeling tighter, and as Hanako suspected, she had somehow gotten even bigger breasts during their trip. Hanako had only become constipated. As for Olivia, stuffing herself on fast food did give her a bit of a pudgy belly, but she knew that with her young metabolism, it would have vanished entirely by the time she got home. She wanted to make the most of her brief trip into belly fat and do their sumo game.

Higuchi was attending a teacher’s meeting that afternoon, so they had the club to themselves. At Olivia’s suggestion, the three undressed in front of each other for the first time outside of gym class. Three loincloths had been prepared for them to wrap around their lower bodies. Their upper halves were going to be completely naked, leaving them topless in the middle of a school day. It was toughest on Kasumi, since she was fighting against gravity with her well-developed chest.

They admired and envied each others’ bodies. Kasumi and Olivia were already growing in more pubic hair than Hanako, though she wasn’t completely hairless. Hanako had a much bigger butt than they expected, but it was ruined by her grabbing her stomach and complaining about the constipation that had been bothering her to no end during class. She blamed the entire country of America for her discomfort.

The match was set to begin, with Olivia and Kasumi squaring off in the first sumo match. Kasumi’s breasts, unrestrained from any sort of cloth, swung freely with her steps. Olivia and Kasumi dashed towards each other, grabbing each others’ arms, when Hanako, still clutching her stomach, asked if they had heard something coming from the closet in the Pastimers Club room.

“That’s just your indigestion,” said Kasumi.

“It is not! My indigestion isn’t that sloppy!” said Hanako.

“Then open the closet if it’s bothering you so much,” said Kasumi.

Hanako walked to the closet and slowly opened the door. Inside was Tsugumi Aozora, skirt raised and panties hanging from the front of the door. Hanako thought she had been disposed of after going rogue, but Olivia Newton Einsten, the robot her grandfather had created for the English competition, was there, sucking Tsugumi off. The robot’s front and back holes were dripping with freshly squeezed semen, having been used for her true purpose.

The robot removed her lips from Tsugumi’s cock, and looked at Hanako with the one expression it was capable of having. Being based on a sex doll meant that she couldn’t emote, but her voice, which spoke perfect English, was filled with hedonism and disdain for the members of the club.

“Knock first when I’m blowing a dick!” the robot said. Hanako, who did not understand English, only grasped some of that. “Fuck you!”

“Thank you, robot Olivia,” said Tsugumi. “That was a satisfying fellatio, but I think the real Olivia would be much better. The wetness and warmth of an actual human can’t compare to a piece of rubber. Even the Lord of the Pastimers is better than you are. It was a novel experience, I’ll admit.”

“Aozora?” said Hanako. “What the hell are you doing here?”

“I was going to watch Kasumi try out sumo. Seeing her tits swing about while she threw you to the ground would have made for an amazing wank. I was content to have my way with the sex robot here, but let me tell you a secret,” said Tsugumi.

Tsugumi stepped out of the mop storage, skirt dropping to the floor. Dripping with fresh cum and sweat, there was a cock. A somewhat above average thick cock with a dangling set of balls. “You got me,” said Tsugumi. “I am, in fact, a boy from the nearby boys’ school. Now, I could get expelled if that was found out, but I’ll offer you a deal. Neither of you three losers have boyfriends.”

“No,” said Olivia.

“Don’t rub it in!” said Hanako.

“Well, I mean...” Kasumi replied.

“I’ll let you play with my cock. I haven’t even been able to masturbate since I sneaked in here, and I’m severely backed up. I’ll let you experience what a real boy, a real boyfriend, a real raw cock is like, if you keep this our little secret. I know all about sex, and I’m willing to teach you. Just looking at you, standing around topless in this classroom, is making me rock hard. Let’s have fun,” said Tsugumi.

Hanako ran over to Kasumi and Olivia, putting herself in the middle of the sumo match. “Should we accept it?”

“I don’t trust Aozora,” said Olivia.

“I thought we were getting closer...” said Kasumi.

“Once he gets a whiff of Olivia’s pits, he’ll make headway out of the classroom and we can forget this whole thing ever happened,” said Hanako. “Besides, Kasumi, you don’t like men, right?”

“I mean... in theory, but I’ve never been around one...” said Kasumi.

“What was that about my armpits?” asked Olivia. “Look, I’ll try talking to Aozora and you two can watch. I’ve read enough of my brother’s doujinshi to know what you’re supposed to do around a boy.”

Olivia approached Tsugumi. She had worked up a sweat during her failed attempt at a sumo match, and the smell of her foreign pit stink was lingering just underneath her arms. Seeing Tsugumi’s raw, throbbing cock was making her loins start to itch. She had considered dressing fashionable and heading out on the town to meet a boy. That she’d be able to do it nearly naked and at school had never occurred to her even in her wildest dreams.

“I... I be Olivia, would you like making suck?” asked Olivia, slipping into her fake “foreign” Japanese. “I study all sorts of techniques!”

“You don’t have to pull that on me,” said Tsugumi. “Just raise your hand and say hello.”

“Hi!” said Olivia.

On cue, she lifted her armpits. Tsugumi approached her left armpit, and took a deep whiff. It was sour, salty, spicy and stank worse than any girl in the entire school. Olivia hadn’t used deodorant today since she knew she’d be doing sumo, and had been nervously excited about it all day. The smell had built up to where it was something rank and fierce, the kind of smell that could knock out anyone who got too close.

“Delicious,” said Tsugumi. “What a boner-inducing stink you have, Olivia.”

“You... LIKE it?” Olivia asked.

“Of course,” Tsugumi said. “A girl being her natural self, that gets me harder than anything. You can’t create a smell fetish with videos or pictures. It’s something you have to experience in person. Your armpits are so erotic, I might cum just from smelling them.”

Tsugumi licked Olivia’s left armpit, taking a big mouthful of her sweat. Olivia was shocked that someone was doing such a thing, but Tsugumi swallowed it. Tsugumi’s cock and balls twitched, dripping precum onto the floor. He asked Olivia to get on her knees. Olivia hadn’t even known that armpits could be used for fucking, but Tsugumi was going to stick his cock right inside her smelly pit.

With her left armpit’s sweat drunk, Olivia lifted her right arm. Tsugumi’s cock slid into her pit, the side of it being brushed in a layer of her sweat and smell. Olivia put her arm down, closing the other side of the cock in her aroma. Tsugumi found Olivia’s armpit plump enough, and coated in a layer of sticky sweat that made it feel rather pleasant to slide his dick into. Olivia was freaked out by the image of Tsugumi’s glans sliding out under her arm, but she had a sense of its thickness and warmth in her upper arms. So she accepted it, and got used to it.

“Fucking this stinky pit is amazing. I guess what they say about foreign girls is true,” said Tsugumi.

“Ye-yes,” said Olivia. “So glad I’m still a virgin.”

Tsugumi started thrusting, moving his cock in and out of Olivia’s armpit. It became coated in a film of her sweat, precum dripping from the glans. Olivia didn’t mind the smell of her own armpits. Everyone liked their own brand. Seeing a cock up close, however, was a new experience. She watched it, wriggling and twitching, a living, breathing organism. Every part of it responding to the heat and warmth of her sticky armpits.

Testicles slapped against her shoulder. Balls that had already been emptied multiple times today, but were still full for several more rounds. The libido of teenage boys was not to be underestimated. At the moment when a drop of white cum started to appear on the tip, Olivia lifted her arm and pushed it back down on the dick, creating a wet, sloppy sound that sounded like an armpit fart. Drops of sweat went flying, and Tsugumi turned to angle his dik towards Olivia’s bloated stomach. Cum splattered over her belly, making her body smell like semen.

“That was fun,” said Tsugumi. “I don’t remember you being this fat, Olivia.” He reached for her belly, shaking it and rubbing the freshly squeezed semen into her skin.

“I wanted to do sumo!” Olivia said.

“You really are a foreigner. I’ve seen your brother, too. Tell me, Olivia. Do you think you’d still be cute even if you were fat? I doubt your breasts could get bigger than Kasumi’s, but there are certain men out there who love girls...” he whispered in Olivia’s ear. “With a big belly.”

Tsugumi stuck one finger in Olivia’s belly button, while moving his other hand down to her pussy, brushing past her blonde pubic hair. He stuck a finger inside Olivia’s pussy, playing with her folds. Olivia moaned, the pleasurable sensation overriding her body. She felt her nipples and clit getting hard, being gently massaged by Tsugumi’s touch.

“Sumo girl Olivia,” said Tsugumi. “Give in and become the ugly American people think you are. I want to see you with a belly so big your school uniform can barely hold it in. Make your belly button deeper.”

“I’ll become a yokozuna!” said Olivia.

Tsugumi pushed Olivia’s loincloth aside, fully exposing her swollen pussy to the classroom. As he fingered Olivia’s clit, she came. Olivia let out the lewdest moan any of the girls had ever heard, and pissed onto the floor moments later. A stream of golden pee flowed from between her legs, creating a puddle on the floor that looked like a sparkling lake of urine in the middle of the room. The kind of lake that Thomas Kinkaide would paint a quaint little cottage near.

“Olivia couldn’t hold it!” said Hanako. Olivia collapsed to the floor, panting and grasping her cum-stained belly. Tsugumi, already aroused from drinking Olivia’s armpit sweat, looked in Hanako’s direction.

“Hanako Honda. You’re a rich girl. I never thought I’d find my way into wealth so easily,” said Tsugumi.

“Don’t underestimate me! Olivia and I have studied in the ways of killing virgins! I’ll blast you away with my shogi!” said Hanako.

Hanako pulled down her loincloth, exposing her bare butt and becoming completely naked. She didn’t even feel shame, her mind having already tricked itself into thinking this was some sort of game. Tsugumi looked at Hanako’s butt, admiring how plump and fat it was, nearly equal to Kasumi’s breasts. While Hanako had no chest to speak of, she had an amazing ass that, unknown to Tsugumi, was heavily constipated. Hanako’s belly was bloated like Olivia’s, but for an entirely different reason.

“I’m a breast man, but I can appreciate a fine rump like yours,” said Tsugumi. “As expected of a Pretty Guardian to moon me. Don’t worry, I won’t penetrate you either. But I do want to have some fun with your fat ass.”

Tsugumi slapped Hanako’s butt. She could take a spanking, even if her face twisted into something that was not sexy at all. Her ass cheeks jiggled, bouncing off each other like a Newton’s cradle. It was a perfect ass, with smooth skin and no markings at all. Tsugumi placed a hand on each ass cheek, moving his cock to the level of Hanako’s butt. He saw her twitching asshole, overworked from dealing with her constipation.

“Where’s your shogi?” asked Tsugumi.

“It’s coming!” said Hanako.

“I don’t see anything. I’ll enjoy myself with your asscheeks,” said Tsugumi. “I think you’ll enjoy how hot and hard a man’s cock can get.”

Tsugumi planted his hard dick between Hanako’s cheeks. It was still covered in Olivia’s sweat, and Hanako had been sweating herself, enough that her ass cleavage was filled with it. Tsugumi started rubbing up and down the length of Hanako’s butt, her squishy ass cheeks pressing against his dick. Hanako’s stomach was audibly growling, still working its way through the very American meal earlier.

“If you played up your anal appeal, you might actually get a boyfriend,” said Tsugumi. “Big butts are in these days.”

“But I want boobs!” said Hanako. “I won’t be an AA cup for any longer!”

“Stop trying to outdo her, you weirdo,” said Tsugumi. “Can you not feel how stiff I am inside your ass?”

Tsugumi pushed on Hanako’s ass from the side, closing her cheeks in around him. Continuing to thrust, he spanked Hanako again. A red mark appeared on her right cheek, hot and stinging. He slapped the other cheek, leaving a matching mark. Hanako’s ass felt hot, but she was no longer sure if it was from the spanking or the hot dick rubbing against her twitching asshole.

“My stomach isn’t feeling so good...” said Hanako. “Your cock reeks like Olivia’s pits. I can smell it all the way over here.”

“That only gets me harder,” said Tsugumi.

“That’s not good,” said Hanako.

Tsugumi’s dick was approaching another orgasm. Hanako’s asshole twitched, and just as she came herself from the light stimulation to her anus, a filthy sound echoed through the classroom. Hanako’s asshole contracted, and sprayed a loud, foul-smelling fart onto Tsugumi’s dick. At the moment of her flatulence, Tsugumi came hard, spraying drops of cum onto Hanako’s back, where it rolled down onto her butt.

Hanako kept farting, the shogi she had spoken of. The smell shot right up into Tsugumi’s nostrils. It was a deeply smelly fast food fart, with the milky scent of a milkshake mixed in. Tsugumi took deep breaths, enjoying how foul it smelled. He could feel his erection returning as Hanako unloaded fart after fart onto his crotch, her constipation blasting itself out with loud sounds.

When she had blown her last fart, Hanako collapsed onto the desk. Her ass was stinging, and she couldn’t move. Tsugumi was hard again. He gave Hanako’s ass one last slap, and looked in Kasumi’s direction. He walked towards her, his hard dick bouncing as he did so, the cock and balls jiggling and shaking with every step.

“Kasumi, I’m familiar with your work,” said Tsugumi. “I read one of your fics online. ‘Two Golden Snitches,’ I think it was called. Where Harry finds himself looking for Oliver Wood’s golden balls while Fred and George beat off over him, ultimately leading to him putting his wand in Malfoy’s goal. It was a decent read for a jerk off session, but you have no understanding of how penises work, do you?”

“You got off to my work?” asked Kasumi. “Even I don’t do that regularly... Wait, what kind of constructive criticism is that? What was the part that got you hard?”

“The scene of Harry playing with his own balls in the beginning. If you want to understand how a man’s penis works, you have the perfect pair for holding one out in the open. Kasumi, I want you to give me a titfuck. To feel your soft, squeezable breasts around my cock would be delightful,” said Tsugumi.

Kasumi pressed her breasts together from the side. She had never thought of them in that way, but it was hard to deny the erection in front of her. She lifted up her breasts, revealing the waterfall of underboob sweat trickling down from her tits. Tsugumi sat on the edge of the desk, and invited Kasumi to press them against him. When Kasumi got close, she almost recoiled. The stench of sweat and semen...

“Olivia’s armpits and Hanako’s farts,” said Kasumi. “It reeks!”

“I love it. Titfuck my dirty cock, Kasumi,” said Tsugumi. “Give into your naughty side.”

Tsugumi pushed down on his hard dick, making it spring back and forth. Kasumi clapped her breasts around it, keeping it firm. The smell was still too much for her nose to handle. Tsugumi gave her a look, ensuring that she didn’t have to lick it. She just had to use her breasts. Kasumi opened her mouth and let her saliva drip into her cleavage, lubing up the cock.

She started rubbing her breasts against the shaft, brushing her nipples against the head. In the middle of her warm cleavage, Tsugumi started doing something he hadn’t done with any of the other girls. Moaning. Even his moans were sensual, making Kasumi feel like moaning herself. The way her pillowy-soft breasts wrapped around his penis was exhilarating, making him more aroused than anything he’d done before.

“This is even better than Honda’s ass,” he said. “Your faintly milky breast sweat is so erotic, Kasumi. You oughta be proud of those big boobs.”

“It’s not like I wanted to do this, but I’m sort of getting into it,” said Kasumi, brushing her breasts against Tsugumi’s dick as she tried to keep her nose from getting too close. Still, the smell, being so close to her, was something she had gotten used to. During sex, her mind was so focused on feeling good that even feelings of disgust were downplayed.

As Kasumi’s sweaty breasts squeezed tighter around his dick, Tsugumi felt himself about to cum. His cock was overly sensitive from being pushed to its limit today, and even the slightest bit more stimulation from Kasumi would drive him over the edge. Kasumi rubbed her breasts, the tight pressure of her cleavage enveloping his dick. Then, Tsugumi came. Hot, thick cum sprayed over Kasumi’s breasts, covering her in a layer of jizz. Some of it shot out so hard it landed on her glasses, obscuring her vision with semen.

“It smells weird,” said Kasumi.

Tsugumi took Kasumi’s glasses and licked his cum off the lenses, showing Kasumi how it had gathered on his tongue, before wiping them off and giving them back to her. “But it tastes delicious. Kasumi, you’re the one I’ve wanted to have sex with the most. Will you let stick it in you?”

“I can lose my virginity before Olivia and Hanako. F-fine. You can dock with me! But go gentle!” said Kasumi.

She took off her loincloth, dropping it to the ground. Her ass wasn’t as big as Hanako’s, but she had by far the thickest mat of pubic hair of all three. Her early development on her breasts had spread to the rest of her body, too. Tsugumi spread open Kasumi’s vulva, looking at her pink insides. A sweet and sour smell came from between her legs, her folds ready to welcome his dick.

“Congratulations on losing your virginity,” said Tsugumi.

Kasumi didn’t know how to react to her lower body being overwhelmed by the fullness of a dick for the first time. Her entire body was hot. She was aware of the weight of her breasts and the hardness of her nipples, her clit rubbing against the edge of the desk. Tsugumi’s dick pounded her, making her oversized breasts shake and jiggle with every thrust, the fat inside them wobbling about.

Tsugumi reached forward, grabbing a handful of Kasumi’s breasts. Her soft flesh wrapped around his fingers, her hard nipples digging into his palms. They were covered in sweat and cum, and felt slightly sticky to the touch, giving his fingers something to grip on. Tsugumi moved them around, watching how they changed shape and reacted to his touch.

“Your breasts could give any man a hard-on,” said Tsugumi. “I love them.”

“My nipples... they’re really sensitive...” said Kasumi.

“So are mine,” said Tsugumi. “Imagine how much fun it would be to press our nipples into each other.”

Tsugumi pinched down on Kasumi’s nipples. She let out a moan, beads of sweat rolling down her body. Hanako and Olivia could do nothing but look in amazement as Kasumi was fucked in front of them, giving into the pleasure of the cock that was buried deep inside her. Tsugumi’s balls kept slapping against her body, making lewd fleshy sounds that overlapped with Kasumi’s moans.

“Do you like it?” asked Tsugumi.

“It... feels good...” said Kasumi. “I may... like sex... after all...”

“I hear you girls go on about your periods all the time, so I know it’s a safe day for you,” said Tsugumi. “That’s why I’m going to give you the full experience on your first time. I want to cum inside you.”

“Yes, cum inside me!” said Kasumi.

Tsugumi bent over, grabbing onto Kasumi’s breasts and squeezing them tightly. With his dick all the way up to the base inside her, he came. Even after releasing multiple loads in one day, the one he pumped inside Kasumi was thick and sticky, giving her a feeling of pleasant warmth that spread up to her belly button. Perhaps it was because Tsugumi regularly played with his prostate that he was able to have such incredible sexual stamina.

With all the members of the Pastimers Club worn out and covered in sweat and cum, Tsugumi pulled up his panties and his skirt and looked towards the door. “Thanks for the sex, girls. Let’s do this again sometime.”

As the door closed behind him, Hanako and Olivia looked at Kasumi angrily.

“Wait, you’re the only one who lost your virginity!” said Hanako. “That’s not fair!”

“We never got to do sumo! And you two didn’t even get fat enough for it!” said Olivia.

“How is it my fault? Now both of you know the plot of my fanfics!” said Kasumi. “Forget everything you just heard!”

When Higuchi entered the classroom, she would have no idea what had gone on. Other than the faint smell of sex, the girls had cleaned up the room well enough. The next day, in Kasumi’s locker, she found a picture of her orgasm face inside an envelope that had been sent to her by Tsugumi.

That’s when she knew which game she was going to have the Pastimers Club do next. Mutual masturbation.