Vacation Blues

I confess: during sex, I’m guilty of imagining how my adventures will translate to prose.

Now, there’s a significant part of my brain during sex that simply acts as court reporter, silently tapping keys that will help me afterward review what happened, so I can jot it down and write up a full account. There’s also a little bit of myself, however, wearing a beret and perched in one of those folding movie director’s chairs, shouting out instructions in order to get the best performance possible. “Hey!” it’ll bark at me through its megaphone. “Why don’t you say this?” Or, “Now would be a good time to suck on your second and third fingers then stick them there!”

As crimes go, it’s pretty mild. Probably not even a misdemeanor. I’m really only indulging in a framing device, of sorts—I’m not only focusing on what’s in front of me, but seeing how my experience might translate into narrative at some later point. This perspective isn’t artificial; I’m not pretending to be someone I’m not, or attempting deeds I wouldn’t ordinarily perform. If anything, I’m looking to bring in experiences that might enhance my partner’s pleasure, to make the encounter more vital. More interesting.

Instead of lying there and staring at the ceiling while I’m letting some guy blow me, I’m finding and saying words I know he longs to hear—not just because it reads better in a blog entry (although it does), but because it inspires him to suck better, to sex me harder, to work more assiduously for that load. I push my encounters a little further than most men not solely because I know it’ll make a hotter story, after I do it to make the sex spicier. I’m bringing my A-game when I fuck, each and every time, just because I know that when I do so and I write about it afterward, the resulting story will inspire boners in anyone who comes across my blog.

Pun intended.

Last week I went on vacation—a birthday week trip to someplace sunny and warm. I spent most of my days doing the kinds of things one does on vacation, walking around, reapplying sunscreen, sipping frozen drinks by the pool. At night, though, there was a cruising area near my quarters that I’d visit late in the evening, when the shadows would be teeming with men looking for sex.

Hot damn, I thought to myself every night, when I’d arrive on the scene, cock ring gripping my nuts, cock bouncing through the thin fabric of my shorts. I’m going to have some stories to tell after this! I’d dress as minimally as possible—a T-shirt and shorts and sandals, most nights. My pants were going to be coming down anyway, I reasoned. Why place any impediments between the guys I was meeting and what they wanted?

And I met some hot guys, last week. Like:

• A skinny, sexy nerd in Warby Parkers and a plaid short-sleeved work shirt who was so shy and nervous the first time I touched him that he nearly flinched when my hand touched his arm. When he unzipped his pants, out flopped one of the largest cocks I’ve encountered—easily nine and a half inches and probably a good seven around. “Jesus,” I whispered, as it thumped into my outstretched palms. “That’s huge.”

“You think?” he whispered back. “It doesn’t seem bigger than yours.”

“Trust me,” I said. I know when I’m outclassed. “It’s bigger.”

• A bearded fucker who, upon seeing me, yanked down my shorts and shoved me up against a nearby wall. “Let me see that hole,” he begged. “You like your hole eaten?”

Yeah. I liked my hole eaten. I widened the stance of my legs and stuck out my ass, only to feel his hot breath on my cheeks. A moment later he was grabbing them and pulling them apart, roughly shoving his mouth and stubble in my most sensitive spot.

“Fuck! I love this hole!” He didn’t keep his voice to a whisper, like most of the men in the area. He shouted it. Anyone could’ve heard his testimony for a block in any direction. “Fucking LOVE the taste of this sweet HOLE!”

A crowd gathered around as he used his weight to keep my face pinned to a railing next to the wall. “Maybe I even want to FUCK this HOLE!”

• Same night. One of the men from the crowd who’d watched the guy rim me approached. Grabbed his meaty groin, rubbed the bulge inside. He was a Latin man. Beefy. Muscular. Mustached. I rubbed him back, only to find myself up against the wall again, legs spread, arms clutching for a hold. He ground his meat against my crack for a moment, then yanked down my shorts until they puddled around my ankles. I felt his lips against my ass, kissing the soft skin as he grappled with the buttons of his 501s. I gasped when he shoved two fingers up my ass. Then I felt the searing heat of his unleashed cock, like a brand, against my pucker.

• Different night. There was a skinhead standing in the cruising grounds. Shirtless, wearing jeans and a leather halter. There were tattoos covering his chest, reaching down from his shoulders in curlicues to encircle nipples pierced by bars. He was muscular, good looking. The other men were frightened of him—frightened of his rough look, put off perhaps by his hardcore appearance. I approached. He leaned back against the railing when I came near, let his fingers dangle near his crotch.

When I reached for those nipples, intersected by cold steel, he melted. His mouth opened and breathed out a gasped “Ohhhhhh—!” Then he lunged for me and wrapped his arms around my chest as his mouth pressed against mine.

“Good boy,” I whispered to him, as the kiss ended. He groaned again, and my fingers plunged down the crack between his jeans and his ass to snake through the canyon of his cheeks until I reached his hole. When I slid the tips inside, I found that it was already sopping wet.

“Suck my dick,” I whispered. He looked at me with the adoring eyes of the submissive, and dropped to his knees.

Now, any of these encounters—and there were more like these—could be a story unto themselves, right? When they were unspooling before me, I kept thinking of the ways that they should go, and for every single one of them, my imagination led me to believe I was headed straight into bow-chicka-bow-wow porn movie territory, with some high-voltage fucking and dicking

And I was terribly, terribly wrong. Because in every single one of those cases—and in all the others I didn’t present here—the story would’ve ended like this: “And the dude jacked himself so hard that he came. Then he ran off.”

Mr. Warby Parkers? I barely had his thick meat in my hands, and I was ready to kneel down and attempt to unhinge my jaw enough to take it in my throat, when he dribbled out a small load. “Sorry,” he said, fleeing before he could even zip up.

The guy rimming me? He actually came while he was shouting he wanted to FUCK my HOLE. Then he was done.

The Latin guy? He got his cock out of his pants and, while I was begging him to shove it in, he leaked out a sloppy few spurts into my shorts, rendering them very messy to wear afterward.

The skinhead? It’s true that I got a good thirty seconds of sucking out of him, and that I pissed on him after that while a group of guys watched. But the second time I said “Good boy” while twisting his nipples, he came so hard that he nearly lost his balance and tumbled over. Then he nodded and scampered away.

After each encounter, I’d see the giant words THE END emblazoned over any hopes I might have for a hot sexual tryst, and hear the sad trombone in the background playing a great big waaah-waaaaaaaah. I found it incredibly hard to believe the weird sameness of my encounters, as they approached their inevitable conclusion; whenever I’d encounter a new guy, I would think to myself that all the previous men had just been a bad streak, that my sexual mojo was off.

The more it happened, though, the more I was convinced that someone was playing a cruel joke on me. What are the odds, after all?

Then I had an encounter that put everything into perspective.

Midweek through my stay, after midnight I wandered out to the cruising grounds. A cluster of men huddled together in a group of about a dozen off to one side, where light wasn’t reaching. I could easily have wedged my way through and found someone to grab at me—but temperamentally, that’s simply not my style. I don’t try to get in with a crowd; I’m arrogant enough to expect the crowd to come to me. It usually does.

So I leaned up against a wall a couple of dozen feet away from the group, casually watching as shadowy figures would walk by to see what was going on. Some of the figures would stride over to the crowd, observe for a moment, then wander back to make eye contact with me. So it wasn’t long until I had a smaller number of men around me, waiting to take turns on my cock.

I’d already had one cocksucker kneel down, take me into his mouth, and immediately blow his cum all over the planking beneath our feet. Three men were watching as another took his place. The guy sucking wasn’t bad looking by any means, but his technique could use some improvement. He was the sort who assumed that I’d be impressed by the sounds of gagging and of him generally struggling to get all of me in his throat. To be blunt, he assumed wrong. What I prefer to hear is a hum of pleasure and the sound of gratified silence, thanks very much; if I want to hear gargling and phlegm, I can visit my dad’s place and sit at the breakfast table with him as he attempts to empty his clogged nasal passages into a much-used handkerchief.

One of the men witnessing the carnage leaned in close next to me. His hands roamed over my chest, down to the root of my cock, to my ass. While the cocksucker struggled to gulp me all down, he whispered into my ear, “I can take better care of that than this guy.”

A vacuum cleaner retrofitted with a wet paper towel attachment could’ve taken care of me better than the guy in front of me right then. I let the statement pass unremarked for a few moments, as we both watched the guy kneeling down bob awkwardly back and forth. “Yeah?” I said, finally.

“Yeah.” He nodded as our eyes locked. “A lot better.”

I could tell at this point that the guy sucking me was close to shooting. He had his pants around his ankles and was furiously jacking. Besides, I was nowhere near close to shooting, what with the massacre he was making of the job. “What do you propose?”

“Come back to my room and find out,” he murmured.

Now, that was what I was hoping to hear. As much as I like public sex, there are times and circumstances when I’m all about the private one-on-one. So I withdrew from the cocksucker’s gullet, pulled the elastic of my shorts over my erection, and plunged my hands in my pockets in an attempt to conceal the hard-to-miss outline of my eight-ish inches of rigid dick before we stepped back into the light and made our way back to the resort’s rooms.

Okay, I thought to myself once we got behind closed doors. This story is going to have a happy ending. The guy stripped me down while I got a good look at him. Smooth body—not super-fit, but at least he was height and weight proportional. Balding. Gray-haired, maybe slightly older than I. Bearded. A decent-looking man. What I liked better, though, was how he seemed to know what he wanted. Once I was naked, he threw me onto his bed, stripped off the polo shirt he’d been wearing, dropped his shorts, and climbed right on top of me, pinning me down with his weight.

The dude’s cock was soft as he made out with me. Not surprisingly, I didn’t mind. A soft cock is a cock that’s unlikely to shoot prematurely, in theory at least. He chewed on my nipples, licked my balls, did all the things I like as a preface to sucking my dick. And the guy sucked well. I oozed out precum as he slobbered up and down the shaft. He was indeed doing a much, much better job than the cocksucker outdoors.

When he pulled himself off, a few minutes later, I was a little bit surprised when he climbed all the way up on the mattress and straddled my hips. With one hand he grabbed my cock and pulled it into the crevice of his ass; with the other, he pulled one of the cheeks up and back so that my slimy head could nudge his hole. Then he began to sit down on it.

“Hey,” I started to say, before we went any further. We hadn’t discussed fucking.

“It’s okay,” he reassured me. “I’m on PrEP.” I nodded. “I freaked out when I had a condom break in me last year, and I figured it was for the best. Fuck me bare. You know you want to.”

“All righty, then,” I said. The guy sounded like he knew what he was talking about—and he acted like he knew what he wanted. I like both things. I took the statement that he was on PrEP to mean that he wasn’t too concerned about my status and that he wanted the raw fuck. “How about some lube?”

Thirty seconds later I had the guy’s legs in the air, my hands gripped firmly around his ankles, as I was sliding my raw dick in and out of his ass. It was the first time I’d actually fucked on vacation, and I was determined to relish the hell out of it.

My partner seemed to be enjoying himself, too. “Fuck fuck fuck,” he kept saying. “I haven’t had dick in my ass in so long and this feels so amazing!”

“Good,” I’d grunt, fucking harder. I switched to long-dicking him, my shaft pulling all the way out before plunging back in again. “I want your hole feeling amazing.”

That’s when it happened. He came. I hadn’t noticed his cock become erect. He certainly hadn’t been jacking it. I just know that as he gyrated and writhed around my meat, suddenly a thick load of sperm puddled around his semi-erect head. He cursed and moaned as the orgasm subsided. Then he looked at me.

Fuck, I thought to myself. End of story. He’s going to tell me he can’t go any more now that he’s shot.

I was half-wrong. “Get out of me,” said the guy. Everything about his demeanor had changed in the space of a few seconds. That open and friendly face now looked angry—mean, even. Moments before he’d been pushing his hole against my dick to take as much of it as possible. Now he was trying to scrabble away from me as fast as possible. “Get that dick out of me!” he yelled, loudly enough that I was afraid people in the rooms on either side might hear.

“Okay, okay,” I said, withdrawing. My dick flopped out, wet and red and swollen. “You’re good. It’s all right.”

“Did you cum in me?” he demanded. I shook my head. “I said, DID YOU CUM IN ME?”

“No, I didn’t cum in you!” I exclaimed. I was baffled at his overreaction—and quite frankly, more than a little frightened by it. “We didn’t talk about where you wanted me to shoot. So I didn’t cum, and I definitely didn’t cum in you.”

“You might have secretly cum in me,” he said, suddenly all paranoia.

“I didn’t secretly cum in you.”

“That’s what you would say if you’d secretly cum in me,” he pounced, seeming to take that as proof.

“I didn’t,” I repeated, “secretly cum in you.”

“You might have.”

I felt like I was staring down a borderline hostile dog. I kept my voice calm and reassuring, but my eyes didn’t waver from his. I raised my eyebrows. “I did not,” I said, slow and steady, “cum inside you.”

For a moment he glared back, still hostile. “Okay,” he said. “You better not have.”

By now I was searching for my clothing. I was angry. “If I can be frank,” I said, trying not to lecture him and to soften it down to sound like advice from a friend, “maybe you’d be better off stating your expectations before you ask guys to fuck you bareback?”

“I can’t help that I asked you to fuck me raw in the heat of the moment.”

It seemed to me that was indeed the one thing he could have helped, and should have helped. “If you’re on PrEP, you really don’t have to be worrying about—“

“I’m a physician,” he snapped. “I know what PrEP is for. I also know that it’s not one hundred percent effective.”

A physician? A fucking M.D.? Then he should've known better. I thought of all the counterarguments I should be making right then—most of them centered around the regimen’s proven efficacy in preventing HIV transmission and that the primary reason he’d originally started taking it, according to what he’d told me earlier, was so that he wouldn’t have violent freak-outs like the one he was having before me. Instead I just shrugged. I wasn’t in the mood.

“Where’re you going?” he asked, as he watched me pull on my shoes.

I would’ve thought that was apparent. “Back to my room. To sleep.”

He got up and stood between me and the door. “Well, let me get a look at you.” He held me at arm’s length by the shoulders, and positioned me so that I was somewhat in the overhead hallway lamp. “I didn’t get to see you in the light before. I want to be able to recognize you if I see you around and I’m horny again.”

Now, this is the point of the story at which I’d like to stress that as bad as it was at this point, after this asshole blew his load, we still haven’t gotten to the really bad part yet. But when he indicated that after his little temper tantrum, after his suspicion and accusations, after his snapping and shouting at me, that he assumed I’d still be willing to have sex with him again, I knew he was a fucking lunatic.

Okay. With that established, I’ll say that what came next was the really bad part of the encounter.

“Yeah,” he said, looking me over. “I’ll be able to recognize you. Bulbous nose. Rosacea on the face—or sunburn? Tall guy, posture could be better. Little bit of a belly. Maybe twenty pounds overweight? Definitely a little bit of love handles. Squinty eyes.” While I blinked at him, he rattled off maybe a dozen more of my physical characteristics—every single one of them phrased as a fault. A lot of them, I hasten to add, purely imaginary.

Now, I am not so emotionally delicate that I shatter into a thousand pieces when someone tosses a little bit of an insult my way. My sense of self-esteem is not crushed when someone says I have a bulbous nose or a little bit of a belly. It takes a hell of a lot more to make me feel badly about myself than that. But as I stood there, listening to this dimwitted, medical-school-trained fuckmonkey rattle off a list of what he found to be my physical shortcomings, all I could do was stand there and wonder who the fuck he thought he was, and where the fuck he could get off.

“Yeah,” he concluded. “I should be able to recognize you. Maybe we can do this again.”

“Excuse me,” was all I said. Then I moved him out of the way, and got the hell out.

I guess I shouldn’t be surprised that I had so many bum encounters during my week away. It’s not as if men suddenly lose their neuroses and insecurities when they’re on vacation; they’re just as inept and stupid and unfit for adult sexual encounters in warm climates as they are somewhere more wintry.

But compared to being shoved off mid-fuck and then having my shortcomings served to me warm? Those abortive blow jobs, earlier in the week, were suddenly looking pretty darned good.