NOTE: This is my first attempt at writing a story after years of enjoying the work of other authors on this site. All feedback is welcome - please be gentle with a first-timer!
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"I am going to fuck you until you've had enough, and then I'm going to keep on fucking you."
That was the sentence that had sealed it. It was the closing seduction in a series of emails with a stranger I knew then only as "Dave" that had begun when I posted an anonymous Craigslist ad. I was in Las Vegas for a conference, but traveling alone and with plenty of free time on my hands. It had been many years since my occasional, youthful experimentation with other men, and for one reason or another — despite a healthy existence of happy heterosexuality and a successful marriage — I'd been having that long-dormant itch lately. To suck a cock. To swallow a load of cum. To get fucked? God, I don't know why — I'd only done it maybe a handful of times back in my twenties — but lately it had become a growing distraction.
So I sat in my hotel room on the Strip and posted a short ad identifying myself as a married, occasionally bi-curious, fit 40-year-old guy looking to give head and "possibly more." I attached a dick pic and one with my bare torso — glad that I'd continued to keep myself in shape — and asked for tall and masculine tops to send pics and info.
A short while later, my inbox started to fill with more responses than I'd anticipated. I guess Vegas is a good spot for this sort of thing. Most of them were not what I was looking for and easy to weed out right away, but a couple of them showed promise. One in particular was from "Dave."
Dave's initial reply included not just the obligatory photo of his cock, but a full nude body shot from the neck down, and it made an impression. The photo showed the figure of a powerfully built man, broad in the shoulders, with very little body hair, well-developed arms and thick, muscular legs, between which hung a barely aroused but amply sized penis that, at maybe five or six flaccid inches, held the promise of reaching considerable size once stimulated.
Dave let me know up front that he wasn't interested in a protracted back-and-forth. In the space of just a few messages we covered all the necessary ground. He told me he was 52, gay, disease-free, a dominant top, and lived in the area. I confirmed that I didn't have any diseases either and told him I hadn't done this in a long time, that I definitely wanted to give head, and that I was curious about trying anal again sometime but really doubtful I could handle it, especially with his intimidating size. It startled me a little to realize how readily I was sharing my most intimate thoughts and secrets with a total stranger. And then he sent the email that set things in motion:
"It's totally normal to be nervous," his email said. "Don't let that hold you back. You put up your ad, and you responded to my reply, because you want to feel a dick inside you. Part of you is thinking you'll just suck somebody off and satisfy your curiosity and that'll be that. But another part of you wants more. You don't have to admit it to me. You just have to admit it to yourself. That you want to be taken. That you want to have your body filled by a real man. That you want to be somebody's hole to fuck. You're worried you can't take it? That you're just too tight? Boy, yours would not be the first tiny little asshole I opened up. Don't you worry — I'll take care of that for you. And it will feel so good.
"So here's what we're going to do," it continued. "At 8:00 pm you're going to meet me in the main casino lounge of your hotel. We're going to have a couple of drinks, let you relax a bit and get comfortable. And then we're going to go up to your room together, and I'm going to take charge. I'm going to tell you what to do, and you're going to do it. And you're going to love it. Yes, you're going to suck my cock, and yes, I'm going to fuck you. I'm going to fuck you until you've had enough, and then I'm going to keep on fucking you."
That line sent a shiver through me — excitement, dread, possibility, foreboding — and when I read it I couldn't turn back. His message concluded:
"Send a reply to confirm, and include a photo of your face so I'll recognize you. And two more things: be punctual and don't wear any underwear."
I read the preceding paragraphs again, and then again, and realized I was holding my breath. I let it out slowly, and tried to corral the conflicting thoughts that were racing through my mind.
It was like a spell had been cast. My mouth was dry. My eyes flicked back and forth from his words — "I'm going to keep on fucking you" — to his picture, his cock hanging heavy with the threat. I was rock hard; I had a telltale wad of pre-cum leaking through my boxer briefs. I started to imagine what it would feel like to take him into my mouth. I briefly worried that I wouldn't be able to please him at all — that for all my fantasies I'd be a useless amateur not worth his time. He'd just laugh at me and ... no, he knew I was an amateur. That was probably part of the kick for him. What I didn't have the experience to provide, that huge man would simply ... take from me, I supposed ... from my body. I shuddered.
Before I could lose my nerve, I took a pic of my face and sent it back in a new email that simply said, "Confirmed." Shit, if I failed to show up now, who knows what he would do with my pictures.
I had about an hour and a half until 8:00. I stripped and got into the shower. As keyed up as I was about Dave's "threat" to fuck me, I was also pretty nervous about the inevitable pain involved. Maybe I would just be able to blow him and explain that I simply can't physically take being fucked. That could make him mad. I wondered what he would do then; there was no way I could know how he would react or whether I'd be in any danger. But I was going to go ahead anyway and put myself in that situation. It was reckless. It was exhilarating.
All of this had me at peak arousal, and I fought the urge to jerk off. I was afraid if I got off I'd lose my edge and not go through with it. And the nervous tension I was feeling was something I wanted to savor. So I just ended up keening on the edge as I got ready. As I ... fuck, as I prepared myself for him. My stomach fluttered a little at thinking about it that way.
I finished my shower and got dressed — no underwear though, per Dave's instructions. While primed and ready, this is when I really thought through potential safety issues. Dave could be some sort of psycho, after all, or try to rob me or blackmail me, or who knows what. I couldn't eliminate all the risk (and, in that moment, wouldn't want to), but I stashed my valuables and anything containing my full name in the safe, and pocketed only my phone, room key and some cash, hoping the bar didn't have a policy of checking the ID of every customer appearing to be under age 80.
Finally, I straightened up the room and took a long look around, realizing — hoping and dreading — that the next time I walked in there I would be inviting a man who could easily overpower me inside to use me.
Riding the elevator down to the casino level, I was literally trembling. When the car stopped along the way and more guests entered, I felt a rising paranoia that they could tell what I was on my way to do. Like I was emitting a pheromone that signaled to everyone on an instinctive level, "I'm not a real man; I'm a faggot who craves dick." In my mind they were all laughing to themselves at the pathetic cocksucker. I stared a hole in the floor until the doors finally opened to the casino, and then I stepped out into the cacophony.
The casino was buzzing. Row after row of slot machines jingled and rang and formed a maze around gaming tables. Gamblers flitted from one attraction to the next, oblivious, I hoped, to my shameful purpose. At the center of the clamor was a lounge area where twenty or so tables surrounded a circular bar, all protected from the controlled chaos of the casino floor by a waist-high half wall and strategically placed flora.
I was a few minutes early — I'd taken Dave's admonition about punctuality to heart — and I figured I'd have a quick drink to temper my nerves before he showed up. Unless he was already there, I realized. I furtively scanned the lounge as discreetly as I could, but there were too many people, they were all clothed, and Dave hadn't sent me a picture of his face. He would recognize me first, and so I would have to let him make the first move. I supposed that was intentional.