Coffee and a Purple Bra

This story is is about a pervish cis man and trans man and leans HEAVILY about being about the trans man's chest. The trans man has zero chest dysphoria, and the story does not contain misgendering or misinterpretation of the trans character whatsoever. I realize this won't be for most people. Also I'm not good at writing. Enjoy idk LOL

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Jason's roommate Oliver left each morning to buy a $7 coffee. He assumed this was a treat he did every now and then, but as they lived with eachother longer, it was soon evident that this was an every day thing, whether he went to work or stayed home. There was always an expensive espresso in his morning. 24 ounces, no less.

Jason wasn't against treating yourself, but it seemed slightly excessive, but he knew he was much more stingy with his funds and caffeine intake.

His roomie grew no anxiety over such things, and Jason could at the very least admire this about him. On weekends, Jason would be preparing either bottled cold brew, or brewing a (frankly disgusting) coffee from the keurig. Then, Oliver would waltz back in with a 24 oz cup of flavored latte. Every once in a while, Oliver would offer to buy him one. The times he accepted, it was much too sweet and strong for him, no matter how many times he asked "make it smaller and less sweet, please."

When Oliver first moved in as a roommate, he usually wore oversized tshirts and boxers as lounging clothes or pajamas, and tried to keep to himself, but that's hard to do in a little apartment. His curiosity got the better of him and he asked about Oliver's medication, and Oliver confirmed his suspicions in that he was transgender.

After Oliver saw Jason's subdued and positive reaction to his identity and learned of Jason's own sexuality, the man grew much less cold to him. He chatted with him, shared video games with him, cooked for him sometimes...

But was also a bit more bold in his clothing.

His lounge sets suddenly turned from oversized tshirts and pajama pants to pajama pants and small tops, bras, and bralettes. The warmer seasons could have played a part, but Jason was comforted that he seemed okay in Oliver's eyes to wear what he liked around him, despite the average person's expectations from a man like him.

But god. Jason couldn't help but stare, sometimes.

Oliver's physique while more masculine than feminine, leaning a bit androgynous. His limbs were quite hairy and shoulders a bit broad, but his chest was, how could he say.. round, but perky? And it didn't take a lot of staring to understand that information.

His little tops were usually a cute pattern or color, some had lace, and some revealed more than others. The cups lazily caressed each breast, always holding them in place but just barely so. Sometimes, Jason felt Oliver was one move away from his nipples slipping around the inner seams of each cup, but they would always barely hold it together.

All of them were definitely bras, or pieces of lingerie. Once, one managed to get washed with his clothes. "You can call it a bra," he remembered Oliver commenting after Jason struggled to know what to call it upon return. Every now and then, he wore this one bra that looked like it was either crocheted or knitted, which had enough gaps to understand that Oliver's areolas were a soft, rosy pink. Other times, the cups were shaped like flowers. That one was really cute on him, and barely covered anything.

This was the hot body Jason got to see the most every day. Weekends and days off were the best because he would wear this get-up the entire day, oblivious to how if Jason wasn't careful, he'd be left with an uncomfortable hard-on until his earliest convenience.

He couldn't help it. While hanging with his roomie, if he felt himself grow stubbornly hard, he would "suddenly remember" an email he has to send, or a bill he's got to pay. He would scurry off into his room before quickly taking care of business while imagining Oliver underneath him, breasts bouncing and handsome face moaning as he gave him his cock.

He felt he was good at hiding his feelings, Though.

---

On one fateful Saturday in June, their apartment air conditioner broke while the temperature outdoors reached over 90 degrees. Nonetheless, Oliver left the building for his daily expensive heart-stopping iced latte.

As Jason was sticking his head in the freezer, Oliver came back in a huff.

"Guess who's air conditioner also broke and was CLOSED for the morning."

Jason barely moved his head, but glanced at his roommate throwing his keys on the entry table. "Coffee stand?"

"Did you message the landlord yet?" Oliver hastily pulled his shirt right off and was suddenly looking like he never left the house.

His little bra today was purple. Cute.

"Yeah I did," Jason sighed, giving the freezer a close to prevent any precious groceries from thawing, but not without removing an ice pack to take with him. "She said the soonest someone can be here is tomorrow morning. Which is a lie, but whatever."

"Jeeesus..." Oliver moaned. "No air conditioning, no coffee..." he whined as he slumped down on the couch.

"You couldn't go to Starbucks?" Jason asked. Oliver made a face.

"Starbucks can't make them like the coffee stand!" Jason didn't know what he meant by this. Oliver in addition to being beautiful, was also a little pretentious. He shrugged and headed back to his room.

"Im going to try to sleep off the heat."

----

Later that afternoon, a shirtless Jason was surprised awake with a large clunk sound. Opening his eyes felt gross with sweat built up on his eyelids. He removed the now-warm ice pack from his neck and was delighted to realize that the clunky noise he heard was the air conditioner starting back up.

With a sigh of relief, he quickly got up and fast walked to the living room and stood under the large living room vent. He never felt better. Crisp, cold air hit his scalp and face. He only guessed it was a miracle.

"Fuck yes," he groaned, feeling the air roam his long, sweat-matted hair. It almost felt worth it to suffer in the heat for so long.

Glancing at the couch, his roommate was sound asleep and giving soft snores. Without his coffee addiction satisfied, he seemed to be unwakable if the loud air conditioner or Jason didn't wake him.

After being thoroughly chilled, Jason removed himself from the air vent and grew closer to the couch and Oliver. This was a free chance to gander at his pretty body more, so he took it.

Oliver lied on his back, one hand on his stomach and the other dangling to the floor. He wore thin pajama pants that rested just a few inches below the crests of his hips. His boxer briefs sat higher and matched the hue of his bra. A neat trail of hair climbed the visible area of his abdomen.

Oliver's face had a sheen of sweat, his round glasses partially falling off his face. His hair, which was long by guy standards, caressed his face while the rest dangled off the couch cushion. A fuzzy dirtstache graced his upper lip. Oliver reminded Jason of a beautiful prince in all his physical characteristics. So precious, infuriatingly hot.

Jason was bi, but definitely had a sexual preference for men. However, he was 100% a boob guy, which only added another thing he found hot about Oliver that he seldom believed could be a preference fulfilled by a man. Oliver was, quite literally, a boob-guy, and didn't seem ashamed about it.

Jason studied every soft curve and crest while he could. Each breast balanced perfectly on his chest. In between each, he had a small amount of chest hair, but not too much. Usually, the fabric didn't appear sheer on this one bra when Jason would casually glance at his roommate, but because he could gaze longer at Oliver as he slept, it was much more obvious. His pink and lightly puffed areolas shined right through the fabric as his breasts softly rose with each breath. They looked so squishy. So touchable. So..fuckable.

Jason felt his member bulge against the front of his underwear, growing more and more uncomfortable being contained the longer Jason ogled Oliver's tits. He grazed his hand against the struggling shaft which only caused more blood to rush onwards. He let his cock respond with a few earnest twitches.

"Mmph," Jason vocalized, dragging a nervous thumb down his clothed tip. He could feel a damp spot of precum, already. Yeah, he really couldn't help it. He slowly pushed his underwear waistband down, popping out a thick and pent up erection. He had to touch himself while he could.

His hand slid up and down his cock repeatedly, eyes fixated on the inviting, plump tits of Oliver. A new, heavy drop of precum emerged and Jason quickly swiped it with his thumb and used it as lube. His balls were ridiculously heavy, but that was maybe due to the heat.

All his mind could imagine was pulling Oliver's bra down and popping his perfect boy tits out. He imagined his hands squeezing them together and Jason slipping his erection in between. First thrusting nice and slow, but quickly gaining speed, pleasuring himself over and over while Oliver's face reddened and released soft, needy moans.

His thumbs would roll over each perky nipple as his hips found an unbreakable rhythm, getting closer and closer to orgasm until he could feel the cum well up in his balls until, until-

"Mmmm-" Oliver moaned, shifting.

Jason's heart skipped a beat as he quickly yanked his underwear up, pinning his cock to his belly, and quickly backed up. His cock uncomfortably throbbed.

Oliver groaned again, clearly awake.

"Hey... did the ac start up?" He mumbled as he slowly sat up, wiping his eyes. He gave a tired, sucked in sigh, then turned to see his roommate standing not too far from the back of couch, standing a bit oddly. "Oh. Hi."

"Ah, yes, it did randomly like 10 minutes ago." He looked over his shoulder to see his dazed but pleased roommate.

"Hurraaay...." He lethargically cheered. He paused, still glancing at Jason. "What're you doing?"

"Ah, nothing."

Oliver stared, then sniffled. "Kay." A loud fwump was heard as he fell back into his sleeping position.

All Jason could do was stare at the back of the couch for maybe a full minute. Finally, he heard-

*snore*

Wow, that boy can really sleep, thought Jason, both relieved and excited all over again. He made his way over to Oliver once more and saw his face sound asleep, mouth slightly agape. His tits somehow looked even more pronounced. Jason flipped his underwear waistband down and continued where he left off. He soon found his rhythm again.

This time, his brain conjured up the scenario of him plunging his member not between his breasts, but in his pussy. His tip would tease his entrance and boyclit relentlessly until Oliver was begging for it. He would first pop the head in first, then slowly sink the shaft all the way. Then, he'd fuck him just like how he's fucking his hand right now.

"Fuck yes, fuck yeah-" he mindlessly chanted, barely a whisper. He continued his intense gaze at Oliver's chest, imagining each breast bouncing to his thrusts as he pounded himself into his pussy. God, what would it feel like to go in raw? To pump cum inside him? To have his sperm swimming inside of him?

It was between Jason's fast pumping that he noticed Oliver's tits react to the new, cool air. His once-flat nipples had risen, obviously stimulated. They were starting to poke against his bra.

"Oh, oh god-"

His balls flexed against his hot and trembling shaft. His climax was coming fast. How badly he wanted to spray his precious face with cum, or his tits, his hard nipples, his toned happy trail, his slightly agape mouth, his..everything.

But he halted in frustration, having just greeted the edge. Of course he wouldn't cum on him. He already felt horrible and dirty for this. He sighed and took his time taking in one last look at the beautiful man, before he would concede and finish himself in the privacy of his room-

"Why'd you stop?"

Wh-

Jason's heart practically stopped and eyes went wide. He stumbled back quickly. Oh fuck. He had been awake.

Oliver opened his eyes and smiled. "Hey, why'd you stop?"

Jason stood there, frankly scared and embarrassed. His right hand was less holding his cock now and more covering it than anything. "....I-"

Chuckling, Oliver grabbed the edges of his bra cups and yanked them down, revealing the two soft items of interest that kept Jason hard at night. "Please, continue."

Oh fuck.

His tits softly bounced as Oliver bounced his body ever so slightly, pink areolas and stiff nipples rotating around mesmerizingly. The combination of weary relief and rabid arousal allowed him to cautiously continue stroking himself.

"You think I didn't know you liked me? You think I'm that dumb?" Oliver said with a sleepy smug. It was hard to respond at all. Jason just kept stroking slowly, not wanting to spoil this. "I don't wear these around you for no reason," Oliver continued, as he unhooked his bra and completely removed it off his little frame. He gave a long stretch, then looked at Jason expectantly, who was holding back stroking as fast as possible and blowing his load right then.

"I don't suppose," Oliver started, sitting up on the couch and leaning back into the cushions, "you'd like to see how it is to fuck them?" He giggled and stared back outwardly innocent. His tits jiggled and dropped so perfectly when he sat up. And Jason just got the invite to slip his cock between them, right now.

"Yes," he barely breathed. His hand stroked faster, hips twitching, now only looking for permission to run up, kneel above his lap and squeeze his tits around his cock. And he got just that.

Oliver spit in his hand, and rubbed it between his breasts.

"Cmon, then."

In an instant, Jason had positioned himself on top of Oliver's person, who aided by lightly squeezing his breasts together as Jason dipped his cock beneath them and giving a testing thrust. The sight of his own wet cockhead squeezing up between the pink, shiny tits fogged his brain once more.

"Go on."

Jason gave another wet thrust.

"O-oh-" he involuntarily moaned. Oliver chuckled.

"You like it?"

Jason couldn't even vocalize a proper sentence. "F-fuck.-"

He gave another thrust. And another. And finally the instinctive rhythm in his hips kicked in.

His milky gaze couldn't tear away from his own fantasy playing out right in front of him, and Oliver just gazed back up at him, both smug and aroused. It's like he got a kick out of Jason finally experiencing sexual satisfaction, and god was it about to send Jason over the edge.

"I'm already close," he managed to admit.

"I know."

He began to vocalize his panting- he was on the brink of no return, and it was at that moment Oliver's gaze turned expectant. His tongue rimmed the edges of his teeth before biting his lip, as if to say "I'm ready for your cum."

It was all over from there.

Jasons rhythm finally broke as pleasure flooded his lower half. His orgasm rushed through his body like thunder before finally leaving through his trembling member.

"Fuck," He breathed, hips jerking forward, as the first eruption of cum graced Oliver's chin, followed by countless more, spurting out with such velocity all over him: On his chin, his tits, his mouth, his tits again, and again, his chin one more time, tits again...

Finally the spurts turned to drips, and then nothing. Completely drained. Jason stilled, but remained panting in a daze. A second later, he removed himself from Oliver and the couch, legs trembling a bit.

Oliver chuckled under the layers of cum. "I was getting worried you would never do that."

There was no time or energy in Jason to postulate or be confused by what just happened, but before he could think of something, Oliver rose and strutted to the kitchen, wiping himself off with a large fistful of paper towels. Finally, he picked up his once discarded shirt and put it back on. It clung to the still-tacky surface where Jason spent himself. He wasn't sure whether to feel grossed out or obscenely aroused by that.

"I'm gonna go check to see if they have power."

A still naked Jason responded "The... coffee stand?"

He grabbed his keys and wallet, slipping his feet into flip flops. "Yeah, I'll need the energy to ride you later."

Jason's eyes widened and glanced around at nobody and nothing in particular. "I... uh-"

Oliver turned, rolled his eyes and quickly went back to Jason, catching him in his stutter through an open mouth kiss, slowly but aggressively inspecting and prodding his tongue with his own, before pulling away with a spit trail and a smirk. Oliver then quickly turned back towards the exit of their apartment.

"I'll be back in 20, so... be ready.

Slam.

Despite his orgasm from a mere handful of minutes ago, his erection was on its way to full mast again. He figured he should shower, but it would be a few minutes before he could unfreeze himself from his spot next to the couch.

The apartment was quiet except for the rushing sound of the AC. All he was left with was anticipation and Oliver's discarded purple bra at his ankles.