A First Date

She grinned but said nothing.

"Can I ask what you liked about the profile? I don't even remember what I put on there, just trying not to come off as too weird."

"Well you failed, but in the best possible way," she said. She got out her phone, did some quick tapping, and turned it to show him his profile:

Are you cool?

I eat ass

That was it; all his editing and reediting had somehow been lost. He decided he would never understand the vagaries of modern user interfaces, but silently thanked whatever hapless developer had coded in whatever bug caused this girl to enjoy his profile.

"Ah," he said. "well I guess I found how to attract cool people, anyway."

"Oh, yes," she replied. "Short and to the point is the way to go."

"To the point, indeed," he said. The point being, he thought, I desperately need to eat your beautiful ass. He weighed the pros and cons of being this direct with her, but ultimately decided to play it cool. "Interested in dessert?"

She did a little head bobble as if weighing her options. "I was thinking of some after dinner drinks, maybe. Besides, the dessert would go straight to my ass." She shifted slightly in her chair and slapped her ass (he assumed from the surprisingly loud sound, as he could not see from his position) as if to emphasize the point.

"There are worse places to go," he said, and quickly continued before should could object or otherwise respond, just in case, "Know any good places for a drink around here?"

"Oh, I can think of one. My apartment has just the vibes we're looking for, I think." She again did that thing where she waited just long enough for a response before cutting him off. "If you don't mind."

"Why would I mind?"

"I have no idea. It's kind of a mess, I guess." She shrugged. "But I have Nintendo."

...

She was not lying about the Nintendo. He had driven them the few blocks to her apartment, which was indeed a huge mess. She threw some clothes off a couch and onto the floor to offer him a spot to sit.

"Beer ok? I may have forgotten to mention that his particular bar has a limited stock. As in, just beer. Or I guess milk."

"Beer's good," he added, settling in on the couch. She headed into what he assumed was a kitchen. He looked around and noticed a Nintendo 64 in the middle of a mass of cords and controllers from various console generations, none looking like they were from the last ten years.

It was taking a surprisingly long time to extract two beers from a fridge, even under the assumption that said fridge was as disorganized as the rest of the apartment. John tried to crane his neck around the corner of the doorway Riley had disappeared into but had come to the conclusion that it would be hopeless. He turned his attention back to the tangle of cables amassed in front of what looked to be an old, very much not flat screen, tv. Would it be weirder to look through her games or just to sit here twiddling my thumbs.

Before he had worked out an answer, Riley reappeared from the doorway, holding a bottle of beer in each hand. "Hey," she said, "Sorry to keep you waiting. I hope you don't mind..." she continued, entering the room, clad in an entirely different outfit from the one she had been wearing on the date. She was now in a grayish hoodie, of a size that indicated to John that it was intended more for lazing around the house on weekends than for anything like a date, and below the waist, a garment he was unsure of how to classify: shorts or simply underwear. Regardless, they were pink and left little to the imagination. "The jeans were meant to be just the right level of casual for a first date, but I guess all that Thai food has only made my big fat ass even bigger and fatter."

"Oh, uh, no, no, it's cool," John stammered as he finally managed to pry his eyes back upwards. If she noticed his staring, she didn't seem to mind. "By all means. Good to see you weren't lying about not being prepared for a date. I was starting to feel like the only awkward pervert again."

"So, do you like Mario Kart? Goldeneye, maybe?" She placed one of the beers gingerly in front of him. "Or you can just keep staring at my crotch if you want."

"Uh... uh..." his brain kept failing at constructing a plausible, let alone clever, response. The only thought that seemed to be repeating in his mind was not lying about being trans.

"Relax," she said. "If I actually wanted you to stop staring at my crotch, I would just turn around so you can stare at my fat ass instead."

"It's not fat," he said. "It's nice." Well, that's better than stammering, I guess.

"Can't it be both?" she said, before placing the other beer on the table, turning and stepping over some more piled laundry to the console mess. She got down on her hands and knees and started rummaging through the mess, looking for something, and giving John quite a view of that lovely, round ass in the process.

"Oh, it can definitely be both," he answered. "But 'nice' is the word I would use to describe yours. Among other terms."

"Such as?" she asked without turning her head to look.

"Perfect?" he offered.

She scoffed. "You exaggerate." She seemed to have stopped even looking for whatever game she had at least pretended to be searching for.

"Shapely? Juicy? Delectable?"

She stifled a laugh. "Delectable," she repeated. "Are you going to get over here and help me like a gentleman, Mr. Thesaurus, or are you just going to sit there staring at my juicy, delectable, FAT ass?"

"I'll help," he answered, getting up. "'Gentleman,' though..., well, I can't make any promises."

He thought he might have heard a giggle at that. He got down on his hands and knees beside her. "What are we looking for, anyway?"

"Mario Kart. Mario Kart 64, actually," she answered. "At least that's what I'm looking for."

John flicked his eyes towards her to assess what she could be implying.

"What?" she said, "It's a great game."

"Oh, definitely, a true classic. Takes me back to junior high."

"Junior high, huh? You really are old." She stuck out her tongue as if to emphasize it. "I only know it from playing it with my dad and it was old then."

"Oof," he responded. "Better not look too hard for it, then, since this old man is going to whip your ass at it if you ever find it."

"Ooh, we'll see who whips whose ass tonight," she teased. "Why don't you take a look back there?" She wiggled her hips to indicate the direction.

He turned around, still on his hands and knees, to face to the region of piled cartridges and cds she had indicated with her little hip shake. This, of course, brought his face within inches of that perfect, juicy ass. He just failed to stifle an "mmm" of admiration.

"Did you find it?" she asked.

"I found something," he said, trying desperately to relax.

"Oh yeah?" she said. Her hand reached back to her shorts and pulled them down to the floor, exposing her beautiful ass right next to his face. "How about now? Find what you wanted?"

"Oh god yes," was all he could say before burying his face between her soft warm cheeks.

He hungrily lapped at her pretty little asshole, a lovely dark brown, contrasting with the pale pink flesh of her soft, round ass cheeks. It drew his tongue to its darkest depths. He couldn't stop himself from stabbing his tongue as deep as it would go into her delicious butt. That wonderful, slightly bitter taste he hadn't experienced in months, but somehow even better. He couldn't get enough. His tongue danced up and down her crack, darting in and out of her hole, stretching to taste her deepest depths.

"Mmm, fuck, mmm..." she moaned, "yes, baby, eat that ass so good."

He pulled back for a second to admire it again. Her little brown hole winked at him, his spit overflowing it and oozing down her crack, over her hairless ballsack, and finally dripping down, down onto the floor. He dove right back in for more, his tongue forcing another cascade of spit out of her shitpipe, only to replace it with more, his mouth unable to contain it.

He could have eaten this ass all night, but the sight of those cute balls drew his mouth downward. He sucked her left nut, then her right, coating her skin with more and more spit. His spit dripped down her crack and onto his face but he didn't care.

Propping himself up on one elbow, he reached between her legs and found her cock with his fingers. So warm, so thick, he pulled it gently towards him, pointing its head back between her smooth, creamy thighs. It poked its red head past her balls, pushing them to one side. He wrapped his lips around it as best he could from this angle, taking its warmth into his mouth.

"Ooh, yes...oh fuck that feels so good..."

He didn't really know what he was doing when it came to anyone else's cock. This was only the third time in his life he had even touched a cock that wasn't his own and only the second one he'd ever had in his mouth, but he did what came naturally, sucking, licking, exploring it with his tongue.

Her precum was warm and delicious on his tongue, but he knew he had to compare this new taste with the previous one. He licked his way back up to her asshole and rammed his tongue back in her. She let out a sound that was somewhere between a moan and a squeal and he let his tongue linger inside her, slowly moving it around, prodding her tight little hole this way and that.

"Fuck my ass, baby," she moaned.

He stopped licking her tight little hole and straightened up. Fuck, he remembered. "I don't have a condom." He'd forgotten all about that. Chalk it up to being out of the game for so long.

"I don't fucking care," she said. "Put your fucking cock in my ass NOW!"

He supposed that even had he known with 100% certainty that he would catch an unspeakable disease from doing so, he would be unlikely to prevent himself from following that order at that very moment. He opened his fly and pulled his jeans down faster than he ever had in his life, grabbed his cock, which had become almost embarrassingly hard from the instant he'd seen her hole, and pressed it against her ass.

"Fucking do it!" she was almost screaming now "Shove that fucking cock up my little asshole!"

He pressed forward; she pushed back. After a moment of ecstatic tension, his dick forced its way into her.

"Uuggghhh..." a sound of pleasure came from somewhere deep inside her.

"Fuck, your ass is so tight..." he tried to move, but her asshole gripped him with all its might. "So fucking good." He was feeling very hot and so stripped off his shirt and tossed it onto whatever pile of clothes was closest.

She started moving, slowly at first, but rapidly picking up speed. Her ass released its death grip on his cock and he was able to start meeting her motions. Soon they had built up a steady rhythm, his cock sliding in and out of her, nearly its full length entering and exiting her ass with each stroke. Her beautiful butt cheeks jiggled each time his body slammed against them.

"Oh fuck," she kept repeating, "fuck fuck fuck me. Fuck me with that big fucking cock. So fucking big...fuck fuck fuck...." She had gradually shifted her whole body, her face now against the floor, her right arm uselessly next to it, and her left arm moving furiously as a she stroked herself in time with his fucking.

He pressed against her and reached under her to meet her hand. She stopped momentarily to let him get a feel, then started up again. For a few strokes, their hands moved in one, his on hers, a new sensation for him. He let his fingers drift up the shaft to the head. Precum was oozing out of the tip and coated his fingers. He straightened back up and brought his fingers to his mouth, licking them clean. Delicious.

Riley evidently took the pause in his thrusting as something of a cue and pushed herself forward, letting his hard cock pop out of her and giving him a gorgeous if momentary view of her gaped asshole. She rapidly turned herself around without leaving her knees, and in one fluid motion, grabbed his cock and shoved it into her mouth.

Her tongue worked rapidly, coating the length of his cock with spit, while her mouth and hand worked in tandem, pumping him in and out of her, stimulating here and then there and then there, driving him crazy. She noisily slurped up her spit, gathered it in her mouth, then spit it back out onto his cock, before repeating the process over and over again, each time more sloppily, more loudly.

"Oh fuck..." was all he could manage. This was the best blowjob he'd ever had, he surmised. He knew he was going to shoot any minute if he didn't get a break in stimulation. He pulled away from her slightly, which elicited a look of mild surprise. "Just let me sit down," he explained, "you're making me weak in the knees." She smiled at that one.

He managed to stumble back to the couch while kicking his jeans off from around his ankles. She was on him in a second, her mouth immediately clamping back onto his cock. Her head bobbed up and down, spit falling out of the corners of her mouth as she forced it in and out of her throat, seemingly unconcerned with the fact that he was this close to firing a huge load of cum down her throat at any second.

When she finally took a break for some air, John could see her saliva had dribbled down her chin and soaked the hoodie she hadn't bothered to take off. She finally stripped it off, revealing a pair of pert little tits, an A-cup, John estimated, with little puffy pink nipples standing at attention. She went right back to work, her tongue moving sloppily but determinedly down his shaft.

When she reached his balls, she switched to smaller, gentle lapping. Her left hand moved to his cock, stroking it lazily up and down as she teased every last square millimeter of his nutsack. He took the opportunity to shift his position to a more horizontal one, pulling his legs up and exposing his asshole for (he hoped) Riley's easier access.

Her eyes flicked up to meet his, silently asking for approval. He just licked his lips and pulled his legs up closer to his chest.

Having apparently gotten the message, Riley slid her tongue lower, leaving his balls and taking a first tentative lick of his asshole. Her hand had stopped, grasping his cock firmly but motionlessly and her eyes locked onto his.

"Mmm..." he let the sound of pleasure escape his lips at the warm, wet sensation of her tongue beginning to open him up. For some reason, his mind went to Carrie. She had never once given him a rimjob, although to be fair, he had never asked. He'd never bothered. She barely ever even let him rim her, although even the most clueless lover could have told by how her body reacted whenever he did that her reticence was purely an act.

Riley tongued his asshole a few times probingly, then slowly and gently kissed her way back up his balls and shaft to his cock head, which she lovingly flicked with her tongue. This was almost pleasurable enough to keep him from noticing what he supposed was the forefinger of her right hand gently make contact with his asshole.

She watched him intently as her left hand resumed its stroking, her lips wrapped around his cock head. Her finger pushed in.

"Fuuuck, oh yeah..." he reacted to the sudden jolt of pleasure.

"You like that, baby?" she was almost whispering. "You like my finger up your asshole while I suck your big, hard cock?"

"Oh yeah," he was almost panting as the finger in his ass had started moving in rhythm with the hand working his cock.

"Cum for me, baby," she purred. "Give me your cum. I want it in my mouth. I want it all in my mouth." While she talked, her hand continued to work his shaft, spit flowing between her fingers as she moved up and down the length of him.

"Shit..." cum spurted from the tip of his cock. Her mouth immediately latched onto it, her lips wrapping around his cock head as his shaft pulsated and jerked, shooting what felt like the biggest load of his life into her waiting mouth.

"Mmm, gggg, mmmm..." she sucked it down without losing a drop, never stopping her constant jerking the entire time. Finally, when his cock had stopped shooting hot cum and had started to grow soft in her mouth, she released her grip and smiled. She said nothing and went back to gently kissing up and down his softening shaft, up to the tip and down to the balls.

She pulled the finger from his ass. "That was so hot..." she began.

"We're not done yet," he said. "It's your turn."

"Have you ever even..." she began, but he cut her off.

"I don't fucking care," he said, doing a terrible impression of her. "Put your fucking cock in my ass NOW!"

She laughed, kissed him on the lips, and shifted to an awkward sort of squatting position so she could get her cock against his hole.

"Would it be easier if I moved...?"

"No, shut up and take my cock, you little slut," she giggled at her own words, then rammed her dick up his ass.

The sensation was, well, painful, but in an amazing way. John had never in his life had an object so large up his ass. His max to this point had been three fingers. This felt like a whole fist. While he had been sucking her earlier, it had been hard to get a good estimate of her size, since her cock had been twisted back between her legs at the time. He had surmised then maybe six inches or so, a little on the thick side. So it was a little odd that it now felt like he was being stretched open in the best possible way.

"Fuck, you're tight," she panted, bringing her face close to his. "You've never..." she was almost out of breath; her hips were moving like crazy "...taken it...up the ass...have you?"

"Nuh uh," he moaned. Her dick head was hitting something deep inside of him, sending jolts of a pleasure he had never experienced through him. His cock even twitched a bit at each thrust.

"I'm gonna..." she was failing to get the words out, her face a mask of pure pleasure.

"Do it," he moaned. "Cum in my tight virgin asshole..."

"Fuck fuck fuck, shit..." she sucked in breath loudly. "Fuck I'm cumming..."

He could feel it, her cock jerking and twitching rapidly inside him, sending a flood of hot cum into his deepest depths.

"Oh my god," she pulled out of him, leaving a trail of cum oozing out of his hole. She collapsed on top of him.

...

"You suck at this game," Riley said as her character pulled off another flawless drift around a corner.

"I haven't played this game in twenty years," he said, thumbing his own controller far less adroitly. They were both still naked; he had followed her lead in not getting dressed when she had eventually recovered enough to get up and turn on the tv. It was at this point that she had finally found the game cartridge she had been searching for, it having fallen behind the tv for some reason.

"Excuses, excuses..." she taunted him. "That was really your first time?"

He took his eyes off the screen to look at her for just a second, which was of course enough time for his character to crash into a wall. "First time with a cock in my ass," he answered. "First time with a trans girl. Not first time fucking a girl or anything."

"Ah," she said, her eyes not moving from the screen. "Well, you must just be a natural."

"I guess I did make you cum in about thirty seconds," he teased.

"I came in thirty seconds," she paused the game to look at him, "because I've never fucked a guy in the ass before."

"Really?" he was genuinely surprised. "I imagine a girl like you could kill on those dating apps, just pick up whatever guy you wanted."

"I can," she said. Her tongue moved around visibly in her mouth as she navigated a particularly tight curve in the virtual track. "But that isn't the same thing."

"How so?" he asked.

"It's like this," she began to extol. "Most guys are either gay or straight. Gay guys obviously aren't interested in a girl, regardless of if she has a cock or not. Straight guys, well, most of them, even if they aren't explicitly transphobes, don't want to get with a trans girl, probably wouldn't know what to do with one if they found them. That leaves the surprisingly rare true bi guy and whatever percent of straight guys are into it."