"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?"
