A First Date

Heard your gay now

John glanced at his phone. Carrie, again, of course. He decided to ignore it. It had been, what, three months, now, of this? In fairness to her, he had been at least as bad as she was in the first month or so after their break-up. It was, he told himself for at least the hundredth time, a backhanded compliment, in a way. He'd hurt her and that was only possible if it had meant anything to her in the first place.

This was, of course, little comfort. Oh, he didn't really need comfort by this point, at least not in the shoulder to cry on sense. He'd gone through that phase already, had spent plenty of time lamenting to anyone who still considered him a friend how terrible it was and how he'd never find anyone else and all that nonsense that people do when a relationship that has gone on too long for its own good ends, and now he was squarely in a phase of being more embarrassed by that previous phase than anything else. Carrie would get there, too, he told himself, and maybe stop blowing up his phone at random intervals to snipe at this or that, to rehash old arguments.

Not that he didn't feel, somewhere deep down in his guts, the urge to take the bait. It just wasn't really worth doing at the moment, not worth ruining a perfectly good Friday night that could otherwise be spent more productively drinking a craft beer he'd probably paid too much for while trying to make out constellations through the light pollution. He lifted the bottle of overpriced alcohol to his lips, thinking to himself how it was probably produced at the same brewery as the cheap cans of horse piss he used to guzzle back in college. He'd just gotten a first taste when he was distracted by the phone vibrating once again on the table where he'd tried to ignore it.

Linda saw your profile on that dating app

your into guys now

I knew it

that's why you were always trying to get in my ass

He was almost more annoyed by her consistent misuse of "your" for "you're" now than anything else.

That same part of him deep down in his guts had him almost texting back something about how it had been her terrible pussy that drove him to it, but his more sensible brain parts pushed him to delete the half-completed thought. He replaced it with a simple bi, bye , and amused at the word play, set the phone back down.

What the fuck was Linda doing on there, anyway? he mused. Last he knew she was still with that, what was his name, Steve? Rick? Some generic white guy name, anyway. Not that John was going to come off as exotic to whoever happened on his dating profile, man, woman, or anything else. He briefly considered asking Carrie but decided the better of it. The thought did lead him to pick up the phone, again, though.

Ignoring another couple texts, he decided to check the dating app. He'd filled out the form a week or so ago, initially not knowing what to write in the profile and just typing "I eat ass", then restarting with a far more generic "Looking for someone cool to..." and then getting stuck again, this time on what he was looking for someone cool to do. Hang out? Start a relationship? Settle down with? Just fuck? He didn't really know what at that moment, and so he'd eventually settled on something so anodyne he couldn't now remember it, and then before he'd even gotten a chance to punch it up, work had distracted him and he'd forgotten to even check it. Was that even how it worked? Did one check it? He had largely tried it out on a lark, a sort of declaration of moving on, but he'd never really used one. Never really needed to. Bars had always been sufficient but he'd been going out less and less these days and it was the digital age, for better or worse. Besides, the last time he'd picked up a girl in a bar it was Carrie...

It turns out one did, in fact, check it. There were a few messages that appeared to be spam bots, a handful of overly eager older gay guys, a boy whose picture made him look like this was his first, tentative step at embracing his sexuality, and a lone girl. He took a look at the boy's profile and confirmed: had just moved to the city from a small town in the middle of nowhere and was looking to try stuff out. Fun, probably, John surmised, although he was probably not the ideal guy to usher someone into a world of attraction he himself had only recently discovered. He shot off a quick "hey" and some perfunctory, yet up for anything message, and moved on. Probably the kid would have found somebody more suitable since...three days ago, he noticed the original message had arrived.

The girl, by the name of Riley, was more of a puzzle. Her message just said "I'm cool B-)". He took a look at her profile. She was cute, anyway. Medium length brown hair, white, brown eyes, cute half-smile in the one picture she'd uploaded, which looked like the type of picture snapped without preparation or forethought. He could make out a rather disheveled bedroom scene behind her.

Prove it : P

He messaged back. Low effort, perhaps, but so was "I'm cool," and low effort meant low stakes, which was fine with him. He put the phone down and considered whether he should keep wasting time tonight or head to bed and find something more entertaining for his weekend in the light of day, when his phone buzzed again beside him.

Jesus Christ, Carrie, he thought, but checked anyway. It was not, in fact, Carrie. Evidently one had to opt out of notifications for this app, as he'd gotten a message back from Riley.

Sure. How's tomorrow?

Low effort sometimes worked.

Works for me. Eager to see how you're planning to impress.

Shouldn't be too hard. Where are you buying me dinner?

Ah, the well-practiced pseudo-forwardness of a girl who knows how cute she is.

Depends on if you're cool enough to like Thai food.

Pretty sure everyone is cool enough for that.

The reply had come before he'd put his phone down, so he sent a link to the restaurant's page. It had been a favorite place of his to order from recently but he'd never actually gone inside. He'd mostly adapted well to being single again, at least has he judged it, but still going into restaurants alone was a strange experience and online menus provided none of the same feelings of self-consciousness.

Nice. 7?

Now who's easy to impress? Do you want me to pick you up?

I'm probably too heavy for a piggy-back ride :P

Not the kind of ride I had in mind :P

And what kind of ride did you have in mind ;)

He was still trying to decide how to reply when another string of messages in rapid succession made the phone vibrate in his hand.

Guessing from your profile that wasn't too forward but either way I can get there myself.

Strong, independent woman, after all

strong, independent TRANS woman, I mean

just in case you're the 1% of bi guys who hate trans girls

He was tapping out a reply about how he was squarely in the 99% when another message appeared.

gotta go but see you tomorrow unless you're in that 1% in which case fuck off :)

He quickly modified his response and sent it.

See you then! squarely 99%, don't worry

He waited a second to see if another reply was coming, and when it didn't opted to finish his beer off in one long drink and then head to bed. It had been a while since he'd been on a first date and he wanted to be well rested.

John spent the following morning doing what he loved nearly best in the world: sleeping until the pressure on his bladder was too great to ignore, and then and only then getting up, to be followed by very little of importance. By the time he finished his second cup of coffee and had showered, it was already nearly 1 o' clock. He had some important calculations regarding the night's planned date: precisely when should he jerk off?

The key was to do it far enough in advance of the date so that one would still be able to get it up should the need arise, but not so far in advance that there was time to get overly excited before the date. It was a delicate balancing act.

In his experience, which seemed now to be rather too far in the past for his liking, the former was rarely, if ever, a problem. Over the course of their recently ended relationship, Carrie had gone from enamored with to amused by to eventually annoyed with his seeming lack of a refractory period. Still, the first load after a respite was always the best one, so he still wanted to aim for sufficient recovery time.

In the end he opted to start around 3 o'clock and take his time. One of the advantages of being single, he'd found, was that you could do this sort of thing, so after more aimless wikipedia deep dives and a short walk just because it would have been a waste of a warm sunny day otherwise, he headed to the bedroom, closed the curtains, stripped, and set his laptop on the nightstand before getting comfortable on the bed.

He weighed the pros and cons of jerking to trans porn specifically before his first ever date with a trans girl, decided he was too in his head about the possibility of being one of those dreaded "chasers" and pulled up a tube site specializing in girls with cocks.

The first video that caught his attention was a gorgeous latina girl with a fat cock and a fat ass getting double teamed by a couple of black guys. Skipping the bullshit at the beginning, he found where she had begun working both their dicks at once, trying and failing to fit both of their hard, beautiful cocks into her mouth. He stroked himself, imagining how good it must feel to share a mouth with another man, tongue and cock and cock all moving together.

He imagined sucking a big black cock, thinking how satisfyingly thick it must be forcing its way into your throat. On screen the performers changed position, one guy sitting on the bed, the girl turning to suck him off, big ass up in the air, waiting.

Oh to taste that asshole, he thought, to jam one's tongue up that tight little shitpipe. John was rock hard, pulling on his cock slowly and steadily. The second guy squirted a bottle of lube all over the girl's ass, letting it drip down her crack. Inspired, John reached over to the nightstand, and without taking his eyes off the screen, pulled out his own bottle of lube. He squirted some onto his hand and worked it over his fingers.

He turned onto his side, returning his left hand to his cock, and ran the lubed up middle finger of his right hand up and down his ass crack. The girl on screen was already making vaguely Spanish sounds of pleasure as the cock pistoned in and out of her asshole. John jammed his finger up his ass.

Fuck he almost blurted out. He imagined that big black cock stretching out his own asshole. God, I need a real cock soon he thought. The performers on screen switched positions again. The first guy pulled his legs up as the camera zoomed in on the girl licking his asshole. The second guy disappeared off camera somewhere. I hope he fucks that other guy's mouth, John thought, although he knew this was unlikely.

By the time the girl had shoved her cock up the smaller guy's ass, John was about ready to explode. The second guy reappeared, face fucking the girl as she topped. John quickly fast forwarded to the last minute of the video. The guys were jerking furiously. John timed his own orgasm to match the second one, imagining he was shooting it all over the two fat cocks that were busy covering the girl's face with a creamy double load.

He made a note to see what he had fast forwarded past later and got cleaned up, while the laptop began to autoplay some a skinny white girl's lazy webcam session.

...

He arrived at the restaurant at 6:53, according to whatever unseen timekeeper his phone trusted. Seven minutes early was probably nearly ideal, he had decided, essentially arbitrarily. This seemed to him to be, despite no solid evidentiary basis, enough time that he could not be faulted for keeping his date waiting, even assuming she had also decided to appear slightly early, or her own timekeeping device disagreed with his, or any number of other, unforeseeable reasons she might arrive before the appointed time. It was also not so early as to appear overly eager, or as if he had nothing else to do. He pondered if his date would find the contents of this little inner monologue entertaining or bizarre or off-putting or some combination of those before deciding he was probably just overthinking it since he hadn't been on a real date in quite a while and maybe four minutes early would have allowed less time for this type of ultimately pointless train of thought.

Fortunately he did not even have to wait the full seven minutes before Riley arrived. He had informed the hostess of the reservations he had made, but she had not yet returned from having the table prepared, so the timing was just about right. Riley had easily found him waiting and sidled up next to him. She was even prettier in person than her profile pic had made her out to be. Her shoulder-length hair was brown, as were her eyes. She had a wonderfully girl-next-door look to her in her short-sleeved top and jeans. The jeans were tight enough that he felt he should be able to verify if she was really trans, since he could not have told (nor would he have cared, particularly) otherwise, although he did his best not to think about it for fear of being caught looking. He, did, however, make a note to let her walk a step ahead whenever they would be seated to get a quick look at her ass.

"Hi," he said. As good an opening as any, he supposed.

"Hi," she smiled politely. Her eyes met his briefly and quickly flicked away and continued to observe anything but him, as if the operations of a small Thai restaurant were now the most interesting thing in the world to her.

"The table should be ready in a minute." He said. Yeah, that's the ticket, sure to break the ice with that one...

"I hope so," she said, her gaze finally returning to his general direction. "I'm kind of starving."

"Ah, so that's your plan," he said, eliciting the precise look of slightly amused confusion he was hoping for.

"Plan?"

"For impressing me," he answered. "Like one of those Mukbang things. You think I'm going to be impressed with how much you can eat."

She seemed amused. Nodding, she responded, "That's it, you got me. I know guys love a girl who eats like a hog."

"Oh, yeah," he replied, playing along. "That's why those mukbang videos are so popular, you know. Some people don't get the appeal, I guess, but you know there's a whole audience of guys out there just cranking off like crazy to videos of cute girls slurping down a month's worth of noodles."

"Cranking off?"

Shit, he thought, I'm really out of practice with this stuff. You can't just talk about dudes jerking off before you've even ordered.

"I knew from your profile you were a bit older than me, but where did you get that one from, 'cranking off'?" she continued before he even had a chance to stammer out an apology. "'Jerking off'? 'Jacking off'? Maybe 'beating off' or something."

She paused briefly, and, perfectly timed so as to prevent him from actually responding, continued, "But slang from half a century ago aside, you're right. There's absolutely a group of guys out there spanking the monkey to that stuff."

"'Spanking the monkey?' What decade is that from?"

"Early 90's, I want to say, but I'm not really a history of masturbation expert, so I'll defer to you on that one."

As Riley was saying this, the hostess returned, and waited, pretending not to hear what Riley was saying. With a look that made it clear that she was fully aware the hostess was in earshot, Riley added, "But linguistics aside, I'm picking up what you're laying down. Don't worry, I will put so much spicy noodles down tonight you're going to fill your pants with jizz."

Ahem. "Your table is ready."

To her credit, the hostess had almost managed to keep a straight face. John made a mental note to tip her a little extra just for not complaining. And to Riley's credit, she had not been lying about her ability to put away Thai food. John almost wished he was one of those mukbang weirdos. Also to her credit was her ass; he had surreptitiously taken a look as they had made their way to the table, and it did not disappoint, round and gorgeous in those tight jeans.

"I guess you weren't kidding," he said as she had begun to slow down. The conversation till then had been pleasant enough, if forgettable and bland in the way that first dates tend to be: where are you from, etc. She had only been in town a few years, moving for the only job she had found straight out of college that didn't involve flipping burgers. He, for his part, had been doing an admirable job of asking questions and listening instead of just going on and on about himself. At least he thought so, though it was hard to judge these things and he was feeling very out of practice. "You really like Thai food."

"Just wanted to give you your money's worth," she said. This time she bothered to make sure that there were no other customers within earshot before adding, "in case you really are one of those mukbang perverts."

"Oh, no, just an ordinary, run-of-the-mill pervert, I'm afraid."

"Oh, thank god," she said. "I was beginning to think you were a normie. Seriously, it's surprisingly hard to find anyone who's not just a sexless weirdo in this city."

"Well, I can't say I've never been called a weirdo..."

"Oh, weirdos are fine. I love weirdos. Just not the sexless ones." Riley paused as if considering her next words.

Or is she waiting for him to say something? Or is she just chewing? Am I overthinking this? Fuck it, it's just a random date from an app, and the first one, at that.

"Hey," he said after what felt like hours but was realistically maybe thirty seconds. "Am I doing alright? It's probably pretty obvious, but I haven't actually been on a date in a while."

Her face took on a peculiar look, but not a bad one. Since she showed no sign of wanting to respond immediately, John just continued.

"I feel like I'm doing alright, right? You seem cool, I mean, like, it would be fine to ask you how I'm doing. Like you're not going to mind." After a second, "But, if you do, sorry, never mind." Another second. "So, yeah, weirdo was not inaccurate."

She almost choked. "Yeah, you're doing fine, weirdo. Listened to the girl talk about stuff instead of just talking, etc., etc. You're going to do just fine on the app."

John sighed audibly.

"Plus you're cute," she added. "You're going to get plenty of ass on there, if that's what you're worried about."

"Oh, uh, I wasn't worried , " he started. "Or, like, what I mean is..."

She watched, seemingly amused at his stumbling.

Screw it, she's cool. "I was really just asking about tonight."

"Oh," she smiled, "so you wanted to know if you're going to get any ass tonight?"

"No, I meant, like..."

Before he could even conceive of a way to end that sentence she interrupted, "we'll see. I mean, you're not the only one who has no idea what he's doing." She took another bite, chewed purposefully, swallowed, then continued, "Obviously I come off just as cool as I did online. But!" She paused. "But, it may surprise you to know that I'm not actually that practiced at all this. I just kind of liked your profile and sent a message randomly. I didn't even expect a response."

This surprised John mildly. "Thank god, I thought I was going to be the only awkward pervert on there. Glad to know I fit in with at least some of the user base."