I first saw Jason in a gay bar on a warm night in August. He was wearing a designer shirt that left absolutely nothing about his upper body up to my imagination and, in contrast, baggy cargo shorts that went down below his knees.
"I'm straight," he said. "Just ... you know, curious. I heard that guys give better ... y'know ..." he trailed off, looking nervously around him, as if he was going to recognize someone else in the bar.
"Better head?" I finished his sentence for him. He flinched, like he wasn't quite comfortable with me being that explicit. Fuck that. "Yeah. Most of the guys whose cocks I've sucked have said I was better than any chick they'd ever been with."
He looked even more agitated than before. "So, you're ... you're gay?"
I laughed. "This isn't a straight bar you're in, Jason."
He laughed, too, but his laugh was a lot more nervous than mine. "I guess I didn't expect someone like you to be gay."
"Does that mean you're interested in me?" I said, just going through the motions. I already knew he wanted me, and he already knew it, too.
"Yeah."
"I have a place we can go to, if you want," I said.
He finished his beer and nodded. "Is it close?"
"We can walk."
So we left the bar and walked to my place, a three- or four-block walk that consisted entirely of awkward conversation punctuated by even more awkward silence. He was trying to establish that I was a person, and I was fine with that, but there was something I was looking for that night, and it wasn't a "soul mate".
When we got to my place, I told him to make himself comfortable and went to the other room to get two bottles of water. When I came back into the room, he had stripped his shirt off and was sitting down on my couch. I took off my shirt, paused, and decided to up the ante by kicking my shorts off, too.
I handed him the water bottle and made some crack about keeping hydrated that I'm sure he didn't hear: his attention was focused very plainly on the front of my boxer-briefs, which were (I assume) getting more interesting by the moment with that kind of attention focused on them.
"Why don't we head into the bedroom now?" I asked him. He nodded dumbly and set down his water bottle on the coffee table as I led him through into the adjoining bedroom.
He fumbled with his belt for a moment before he managed to undo it, letting his shorts fall to the ground and revealing his underwear of choice: a pair of plain white briefs.
I'm normally not one for white briefs -- they look boring most of the time, and indicate to me a man who never got the idea that there was something else out there besides tightie-whities -- but he looked amazing in them. I stood there for a moment, admiring him: his package, his ass, both looking great in his tight underwear, and then I moved in to kiss him.
He was a pretty passive kisser, but I didn't mind. I explored his mouth with my tongue for a while, then moved down across his body in a slow zig-zag: biting his earlobes, sucking his nipples (that got me an arched back and a hiss from him), then licking down from his navel to his briefs, which, having been on him long enough by this point, were stripped off.
As good as he looked with the briefs on, he looked better with them off. His cock was about the same size as mine, so I estimated seven-and-three-quarters inches long, but with a better girth than mine. I looked up at him, my hand barely touching his cock, and looked up at him as I pulled his foreskin back and gave a long lick starting all the way down at his shaved balls and continuing up along his hard shaft.
His eyes closed, and he let out a whimper. I was tempted to ask him how long it had been since he'd last gotten off, but he obviously wanted this at least as much as I did, and I'm not always that cruel.
I took his cock into my mouth slowly, focusing just on the head at first, but eventually working down all the way until my nose was brushing his buzzed pubes. Every now and then, I glanced up at him to see if he was enjoying it. He was.
I came off his dick, letting it slap, wet and hard, against his abs. His eyes sprung open and he looked down at me with a face like a wounded puppy. "Why'd you stop?" he managed to say.
I smirked at him and gave his cock a lick, sucking on his balls and working my way further down, lifting his legs onto my shoulders. I kissed his tight hole, and he just about jumped out of the bed, groaning. I figured nobody'd ever played with his ass before.
"I don't know if I want this," he said after I had flipped him over and had my tongue buried in his hole as far as it would go.
I pulled my tongue out and moved back a little bit. He wanted it, and we both knew it, but now I was willing to let him tell me. "Really?"
He didn't say anything, obviously expecting that I was just going to go back into his ass.
"Really?" I said again. He was going to need some prompting. "If you don't really want this, I won't do it."
His cock was leaking precum, dripping it onto my bed. He mumbled something.
"What?"
"I said, I do want it," he said.
"You want what?" I asked him. I wanted to hear this.
"I want ... I want your tongue up my ass."
I pushed two fingers into his wet, slippery hole. "I don't know. I don't think my tongue is going to do much good here. What about some fingers?"
He grunted and pushed his ass up further towards me, obviously enjoying the stimulation I was giving his prostate. "Yes ..."
I pumped some lube onto a third finger and pushed it in, grabbing one of the condoms I kept right next to my bed for occasions just like this. "Yeah? You think maybe you want something more?"
The moaning and thrusting stopped abruptly as he realized the implications of what I'd just said. "Like what?"
"I think you know." I didn't stop the stimulation, even if he stopped moaning; if anything, I intensified it, reaching around to his dripping cock and jerking it slowly.
"Yes." There's a clear answer.
"Yes, you want it, or yes, you know?"
He moaned and thrust his cock into my hand, which had since stopped moving. "Both!"
I withdrew my hands from his ass and cock, ostensibly to put the condom on, but more because I can be a mean bastard like that. "So, what you're saying is ..."
He stayed quiet for a few minutes, trying to find another way to get what he wanted, but he finally realized that he wasn't going to get my cock up his ass unless he specially requested it. "I want you to fuck me!"
I turned him onto his back, raising his legs over my shoulders and pushing my cock into his hole to the same rhythm that I jerked his cock. He moaned and whimpered and yelled with an enthusiasm I hadn't heard for a long time until I silenced him by pressing my mouth firmly over his.
Barely half a minute later, I felt his ass contracting around my cock at the same time that he sprayed the biggest load of cum I've ever seen across both of us. I followed suit shortly after; it was always a pleasure to unload deep inside a boy who, a few hours ago, had considered himself entirely straight. I wondered if he still had any illusions like that.
I haven't seen Jason since: he moved away, but we've kept in decent contact through email. I recently got an email from him saying he was heading up this way with a definite subtext to it, so we'll see how that turns out.
Comments or constructive criticism are welcome; if people like this, I'm definitely willing to write more, and in the absence of any comments one way or another, I'm probably going to write more anyhow. :)