Taking Penis for a Test-Drive

"Well," Jack thought to himself, "It's now or never. Am I really doing this?"

It was a warm, lightly rainy summer night in the financial district, and Jack stood nervously outside the doors of the brightly lit gay bar. It was a weeknight, pretty early. Not busy. Jack had wanted to come when it was quiet. He gulped and thought back to the long and winding path that had taken him here.

Jack had always thought of himself as straight. Well, mostly. He was young, 26, only a few years out of college. Like just about every child of the internet age, Jack had been a confirmed lover of internet porn since early adolescence. The great majority of the time he watched girls, but yea, once in a while he dipped a toe in to gay porn. But that had never really bothered Jack. He knew the unspoken truth that pretty much all straight guys watched gay porn from time to time, and plenty of them had even experimented a time or two with guys, if only to find out that they weren't in to it and then never speak of it again. Jack had never had trouble getting attention from girls, and he liked them. He'd known a fair number of gay guys in college and in his professional life, and never felt attracted to them. So Jack was pretty confident that even if he liked to watch a twink get butt fucked from time to time to change up the pace when jerking off, in his real life he was confirmed hetero.

Not that Jack had any problem with homosexuality, it just wasn't for him. Right? When Jack did watch gay porn, he typically liked videos where large and muscular men fucked smooth and effeminate twinks. He always imagined himself in the role of the dominant top. In that sense it really wasn't that different from the ditzy whores he got his rocks off to when he was jerking off to straight porn, which was most of the time.

It actually wasn't gay porn at all that had set Jack on this path. He had been watching a straight video where a typical busty, made-up slut was licking a guy's ass, and the little whore had stuck a finger in. It looked like it felt good. Jack found himself curious.

So, he decided to try it. Slathering a generous portion of hand cream on his index and middle fingers, Jack had reached down and tried giving his asshole a little massage. He shocked himself with how good it felt. The only thing left to do was to stick a finger in, so that's what Jack had done.

He'd never experienced anything like it. The strange, painful at first but definitely pleasurable feeling of being stretched and opened had caused Jack to quiver all over, and made his dick go from half-chub to hard as a rock in a blink. It wasn't long before he was fucking himself - sort of. Jack couldn't really reach as far in to his ass as he wanted to, and fingers were too skinny. It had left him wanting more.

Still, the rest of that afternoon Jack had walked around with a thrilling, sexually exciting feeling of being, well, stretched. For a long time afterward whenever he sat down he'd feel waves of pleasure run up his rectum. It was a kind of all-body high - way different from regular penile orgasms, which often felt like they were over as soon as they started. He'd run some errands that afternoon and it had given him an erotic, naughty thrill to have that little secret, that he had fingered himself and that his asshole had been stretched and entered, even if only by himself.

Jack had found himself doing more and more of that over the ensuing days and weeks. He'd discovered that he liked to position himself in submissive postures. He'd bend over deeply and brace himself against the wall, or sometimes in the shower he'd stick his middle finger up his butt and then squat down, like a porno whore riding cowgirl, coaxing his finger up deeper in to his asshole. He found his prostate a few times, and the feeling of poking it with the tip of his finger sent shockwaves of pleasure through his whole body. He never quaked and shaked just jerking off the way he did when he fingered himself.

At first Jack had watched straight porn while he indulged in his new hobby, choosing videos where girls fingered or licked their male co-star's assholes. But it wasn't what he wanted. More and more, Jack was sticking his fingers up his rear to gay videos. And for the first time, he wasn't imagining himself as the dominant one. Jack found himself noticing the bodies of the muscular tops in ways he hadn't before. He liked guys with large, muscular asses and thick thighs. He thought it must feel nice for the bottoms to get mounted by guys like that. Jack had always conceived sexuality in terms of his desire for an object of gratification - most often women, but sometimes male bottoms in the gay pornos. But more and more Jack was thinking in terms of being the desired object. It was a different approach and, he found, a satisfying one.

But his finger wasn't enough. It didn't stretch him out far enough, and Jack never came from fingering his ass. He'd do it for a while, then pull out and jerk off. He had more powerful orgasms that way, but it was frustrating. He tried jerking himself off with a finger or two inserted a few times, but the mechanics were awkward.

Jack went on and enjoyed dates with women all through this period. He was handsome and well-educated, and never had any trouble finding a girl to spend the night with on the usual apps. A few times he'd asked them to stick a finger up his butt when they went down on him. They'd always been obliging, and it was pleasurable, but still, not enough.

As time passed, the certainty grew in the back of Jack's mind. He wanted to know what a penis would feel like. It was a strange feeling. As mentioned, he'd never had any objection to homosexuality as such. But the idea of submitting to another man, of getting fucked, was a definite shift in Jack's identity and conception of himself. It was also a thrilling one. More and more, he wanted to try it.

So that was what had brought him here, to this gay bar on a quiet weeknight. Swallowing, Jack took a breath, steeled himself, and walked in.

"Here goes nothing."

Jack felt eyes on him as soon as he walked through the doors. The place wasn't slammed, but there was a decent crowd, and men eyed Jack hungrily as he approached the bar. A charged little thrill ran up his spine. He liked the feeling of their gaze on him, of being desired.

Jack ordered a vodka soda. The cute bartender smiled wolfishly at him as he poured. Then Jack just stood there, sipping it. He wasn't really sure what to do next. All his life Jack had been the one approaching women in situations like this. What were you supposed to do when you wanted a man to approach you?

Jack felt and heard the presence of the figure next to him before he turned to look.

"Another whiskey, please. On the rocks."

Jack turned to see a tall, muscular man in a charcoal gray suit. He wore no tie around his white Oxford shirt, which was unbuttoned at the top, giving Jack a view of his hairy chest. The man had tight cropped hair, black running to gray. The stubble of the close-shaven beard running along his chiseled jaw was the same color. The man turned to smile at Jack. He had thick, well-defined lips. Jack thought they looked kissable.

"Hi, there. I'm Sebastian. What's your name?"

"Hey, I'm Jack."

Sebastian extended a hand to shake Jack's. It was large and his grip was strong. On his right wrist, Sebastian wore a silver, expensive looking watch. On his right hand, a gold wedding ring.

"Do you come here often?"

"First time, actually." Jacked laughed nervously.

"That's funny. Mine too. Care to join me?"

Jack nodded, and Sebastian led him back to his booth in a quiet corner of the bar. Sebastian sat down, and Jack slid in next to him, on the same side.

Jack had noticed right away Sebastian's sexy, European-sounding accent. It turned out he was Spanish, just in the city for a few days for some business meetings. Jack liked that he was from out of town. He didn't really know what he was doing or how he was going to feel about it after, and the last thing he needed was to hook up with some guy, hate it, and then find himself bumping in to him around the city.

They talked for a little while, chit chat about nothing. Jack's gaze kept returning to those kissable lips. Finishing his drink, Jack decided to go for it. This was what he was here for, right?

Jack placed a hand on Sebastian's thigh and leaned forward. Sebastian leaned back, confidently bringing his lips to Jack's. His strong tongue slid in to Jack's mouth. Jack moaned. He had kissed plenty of girls, but this was the first time someone was really kissing him. He liked it.

After a while their mouths parted. Jack removed his hand from Sebastian's thigh and placed it on his muscular chest.

"My hotel is right down the block," Sebastian said, grinning, "Want to get out of here?"

Jack smiled back, "Yea, I do".

Sebastian picked up the tab and they were out the door. It was only a short walk to Sebastian's hotel. He was staying in an expensive-looking suite on the thirty-fifth floor, and a large window adjacent to the bed gave a great view of the city. Jack liked the idea that Sebastian was an important, wealthy man. It turned him on to think of someone like that wanting him.

In his hotel room, Sebastian kissed Jack again, deeply. He was wearing some kind of expensive smelling cologne Jack didn't recognize. It smelled masculine. It turned Jack on, and he moaned slightly in to Sebastian's mouth.

"Listen, I'm going to use the restroom," Sebastian said when they broke off their kiss. "Why don't you take your clothes off?"

Jack nodded, biting his lower lip as he watched Sebastian walk in to the adjacent bathroom and close the door behind him. He was tall, large and powerfully built. Sebastian had the kind of thick tree trunk thighs and large butt that Jack had fantasized about.

Jack pulled his sweater over his head, then undid his belt and took his pants and boxers off. Jack was muscular as well, an athlete, if a little shorter and slighter in build than Sebastian was. He was proud of his body. Jack was already hard, but he took a seat on the end of the bed and started jerking himself off slowly, not really sure what else to do.

The sink turned on briefly, then off, and Sebastian came out. He was completely naked other than the wedding ring and the wristwatch that he still wore. Jack sucked his breath in slightly at the sight of him. Sebastian was tall, built with powerful muscles. Thick chest hair ran down his abdomen, turning in to a happy trail at his belly button. His cock was long, girthy and veiny. Sebastian was circumcised, and the bulb-head of his penis was very attractive. He had a large and heavy-looking set of balls and a fair amount of bush, hairy but not overwhelming.

"So, listen, Sebastian. This is actually like, my first time. With a guy, I mean. So maybe you could just, you know, be gentle?"

Sebastian moved to stand over Jack, smiling and bending over to give him another deep kiss.

"Of course, Jack. Don't worry, it's far from my first. I know what I'm doing."

Sebastian returned to a a full standing position, raising his muscular arms to entwine his fingers around the back of his head. Jack was at eye level with his penis, and it pointed insistently in to his face.

"Why don't you give it a try?"

Jack nodded, gazing up at Sebastian and swallowing some of the saliva that was rapidly pooling in his mouth. Sebastian's cock was beautiful - Jack had really lucked out.

Parting his lips, Jack leaned forward and took Sebastian's penis in his mouth. He was surprised at the feeling. Sebastian's hard dick was warm, and had a kind of rubbery texture. The pronounced veins running along his shaft felt nice on Jack's lips and tongue.

Jack started bobbing his head back and forward slowly, exploring what it felt like. He began to run his tongue in slow circular motions around Sebastian's penis. Sebastian had a definite musk, masculine, not sweet but not unpleasant. Jack enjoyed the taste of him in his mouth.

Sebastian groaned, lowering one hand from his head and placing it confidently on the back of Jack's. He began guiding the motions of Jack's mouth, firmly but not in a rough or dominating way. Sebastian was groaning more often now, and the idea that Jack was giving him pleasure sent a little thrill up his back. It felt dirty, sitting on the bed in this married stranger's hotel room, sucking his cock, submitting his mouth to an older and more powerful man. Jack liked it.

The tip of Sebastian's penis began to poke in to the back of Jack's throat, and he gagged a little bit, unused to the feeling of a foreign object not under his control being inserted in to his mouth.

"Just relax, Jack. You're doing great." Sebastian instructed, breathing a little harder now.

Jack did as he was told. He focused on relaxing his throat muscles, letting Sebastian's girth slide in and out, in and out, a little farther each time. Jack's eyes wandered over Sebastian's muscular body, drinking it in. He thought about Sebastian's spouse at home, whoever she was, and whether she suspected her husband was getting his cock sucked by boys on business trips. Jack liked the guilty, naughty feeling it gave him to think he was sucking a married man's cock.

Jack regretted it a bit when Sebastian pulled his penis out of his mouth. A long string of saliva still ran from Jack's lower lip to the bulbous head of Sebastian's veiny cock.

"Okay, Jack. Get on the bed."

Jack looked up at Sebastian and nodded obediently. He was excited, but scared. He had never had anything more than a couple of fingers in his rear. The well-endowed Spanish businessman was going to be a big step up.

Sebastian must have felt Jack's nervousness. He smiled warmly. "Don't worry, I'll be gentle."

Jack crawled on to his hands his knees, facing away from Sebastian. He raised his hips in the air and lowered his face in to the pillows, offering up his hole in a submissive posture. Jack started slightly when he felt a dollop of cool lube squirt against his sphincter. Sebastian's thick and powerful fingers were massaging his rear. Jack moaned when Sebastian slid first one, then another finger in to him. That familiar stretching sensation was back now, but Sebastian's hands were much larger than Jack's, and it was all the more powerful.

Sebastian worked his hands at Jack's asshole for a little while, loosening up his entrance. Jack was enjoying himself, pushing himself back on to Sebastian's fingers and bucking his hips, getting more and more used to the feeling of his butt being stretched and loosened.

Sebastian removed his hands and climbed up behind Jack, his thick and powerful thighs framing Jack's smaller legs. Jack whimpered in spite of himself when he felt the round head of Sebastian's penis press up against his anus, strong hands gripping his hips tightly.

"That's it, Jack. Nice and easy."

Jack cried out as his virgin sphincter began to stretch, Sebastian's penis pushing slowly inside him. Sebastian's head was through now, and Jack could feel his narrow hole clutching tightly around its girth.

"Ahh... Jack... you're so fucking tight..."

The long and veiny shaft was driving forward, slowly but insistently, Sebastian burying himself deeper and deeper in Jack's clenching butthole. Jack cried out, his face contorting and his hips quivering. The feeling was undoubtedly painful, a kind of sharp stabbing as Jack accepted a man's penis in to his ass for the first time. Still, Jack found it erotic, the idea of submitting to a powerful male, of bending over for him and giving up his body to serve as the vehicle of his pleasure.

Sebastian was in all the way now, his heavy balls resting against Jack's own. He pulled out slightly, then pressed back in. Then out and in. Out and in. Sebastian was fucking Jack gently, but with authority. He placed his arms close around Jack's face, making fists on the bed. Jack gripped Sebastian's strong biceps for support, feeling the heat of Sebastian's abdomen lowering down over his back. The feeling of the businessman's muscles contracting against his ass and back excited Jack as Sebastian mounted him fully now and began to fuck him steadily.

"Ahhh... Sebastian!" Jack cried out, digging his nails in Sebastian's arms, gasping as the painful feeling of his prick filling Jack's ass started to turn to one of pleasure.

"Yes, Jack... good boy.... take that cock like a good, submissive bottom."

Jack's was moaning more and more steadily now, the feeling of his passage stretching and Sebastian's penis pressing in to him sending waves of pleasure through Jack's body.

"Ohhh... ooooohhh yes... fuck me, Sebastian!!"

Sebastian started to pick up the pace, his tree trunk thighs slapping hard in to Jack's rear end. The hotel suite echoed with the sound of their clapping flesh. Jack glanced up at the window. The blinds were still wide open. The entire city could see him bent over on his hands and knees, getting butt fucked by this suave foreign businessman.

"Jack... fuck... your asshole is so tight, Jack... you feel so good wrapped around my cock!"

"Yes Sebastian! Oh yes, please, please fuck me!!"

Jack was moaning and crying like a gay porno bottom now, the bed shaking, the headboard banging against the wall, loud enough to wake anyone sleeping in the next room.

"Sebastian! Ohhh, Sebastian!!"

Jack removed his hands from Sebastian's arms and reached back around him, gripping hard on his lover's muscular asscheeks, feeling his hips driving back and forth as Sebastian's hard cock pistoned in and out of Jack's virginal asshole.

Sebastian was breathing hard and grunting, humping Jack harder and faster. His long penis was poking repeatedly in to Jack's prostate, and Jack could feel his long-awaited anal orgasm approaching. Jack was diamond hard, his balls swinging freely beneath him as Sebastian pounded away.

"Ohhh, Sebastian! Fuck me, Sebastian! You're so deep in my ass!!"

Jack's face was contorting, his eyes clenched shut, his mouth wide open. He was panting and gasping for breath, his body rocking back and forth as Sebastian drove himself in to him.

"Ohhhh, Sebastian!! Ohhhh! Oh my go... oh my god I'm gonna fucking cum!!"

Jack moaned and cried as his hard cock began to quiver, spurting hot cum across the hotel bedsheets, driven to anal orgasm by the force of Sebastian's large and girthy penis driving over and over in to his tight, clenching butthole.

"Fuck... Jack! You're so... fucking.... tight!!! AHHHH!!"

Sebastian cried out as his came. Jack pushed his hips back and ground himself in to Sebastian's pelvis, moaning and crying as the muscular Spaniard's big cock jerked and twitched inside of him, spurts of hot cum shooting up Jack's rectum.

Jack collapsed on the bed, laying in his own warm cum, and Sebastian collapsed on top of him. His penis was still buried deep inside Jack. The feeling of Sebastian's powerful, muscular, gratified body pressing him down in to the sheets was an erotic thrill. Jack moaned as he wiggled his ass on Sebastian's cock, pressing the back of his thighs up against the larger man's hips and testicles.

Sebastian cupped Jack's chin in his hand, turning his head back toward him, kissing him hungrily. Jack and Sebastian's tongues danced against one another, both men still breathing heavily as they came down from their mutual orgasms.

"So, how was your first time?" Sebastian asked, his lips curling in to a grin against Jack's as they broke their kiss. Jack liked the feeling of his rough stubble on his own clean-shaven face.

Jack gazed in to Sebastian's dark eyes adoringly, "That was amazing. You fucked my ass so good."

They lay there for a while, Sebastian holding Jack in his thick and powerful arms. Afterwards, they took a shower. Sebastian fucked him again beneath the steaming water, and came in his mouth this time. Jack found he liked the taste of Sebastian's warm and salty sperm on his tongue.

When they'd gotten cleaned up, they exchanged numbers. Sebastian promised to text Jack the next time he was in the city. They paused for one last passionate kiss before Jack left Sebastian's hotel suite, well-fucked and feeling used like a dirty slut. When Jack climbed in to his uber, he relished the feeling of his stretched out rectum pressing against the firm seat, a lasting memento of his lover's penis.

Jack gazed out the window at the city lights contentedly as the car drove off toward his apartment. Things were never going to be the same.