A Key West Spring Break To Remember

By deanie McSweeny

Published on Apr 9, 2021

Encounters

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I have had many same-sex experiences. I will recount one of them now and try to come back and provide more later. The one that comes to mind right now is an experience I had in Key West FL my senior year in college.

To provide some background, I consider myself to be heterosexual. I don't find men attractive. I don't really fantasize about kissing them. When I have played with men, it's not that they turn me on per se, it's that the idea of doing something that's so wrong and dirty turns me on.

By my senior year in college, I had been with six or seven women. I had a girlfriend who was simply to die for. The thing was we only started dating about three weeks before spring break, so we already had separate plans. This was the first time I would be apart from her. Candidly it was the first girlfriend I've ever had. All of my prior sex experiences had been one-night stands.

I honestly didn't know what I was going to do when I got to Key West. Every previous spring break I'd always spent most of my time trying to get. When it came down to it, with alcohol involved and all these hot women running around I said screw it and hit on women every night. I was largely unsuccessful, but it was a lot of fun.

One night, as was often the case, I got hungry near the end of the night and went to one of the all night pizza places to get some food. When I returned to the bar all my friends were gone, so I was left alone to make the mile and half or so walk back to our hotel. As I was walking back, a red Miata pulled up next to me and the min inside asked me where I was going. I Explained I was walking back to the hotel and he asked if I wanted a ride.

As soon as I got in, he shook my hand and introduced himself. I remember his name, but we'll call him Frank. He asked me if, before I went home, did I want to smoke some weed with him. At this point in my life, I was an ROTC candidate and subject to fairly frequent random drug tests. I had never smoked marijuana before but decided, screw it, I should give it a try. So, I agreed to go back to his place with him.

Once we got to his rented condo, Frank made a couple of drinks and went to go get the weed. I don't remember exactly how it started, but eventually it dawned on me that he was basically trying to seduce me. He was sitting close, he was finding excuses to touch me, and in the parlance of the language I used back in those days, I finally realized he was a fruity little faggot.

He finally asked if he could rub my shoulders and I said yes. It felt so good. The combination of the alcohol buzz I already had plus this new experience of smoking weed and these soft tender hands rubbing me all felt new and great. I started moaning and he took it as an invitation to go further. From behind he unbuttoned my shirt and started rubbing me all over. He eventually came around between my legs and suggested I get very comfortable as he started to undo my pants. This was the first time I took proactive action to escalate things by lifting my hips and letting him pull my pants and underwear down. I was perhaps feigning ignorance but I knew where it was going and at this point my hard dick gave things away.

At any rate he started rubbing my thighs, being careful to avoid making actual contact with my cock. What he did do though, was to lean in and give my balls a sniff. I don't know why, but that was so much hotter than if he had gone right in and started giving me head. At this point I was totally naked with a raging hard on and he was totally clothed. He asked me if I wanted to go lie down in his bed so that I could get a better massage and I agreed.

I sat down on the bed and he gently pushed me over and started rubbing my chest and stomach. In those days, I was very fit and very ripped. I started flexing my pecs and abs as he continued to rub everything. This is when he leaned in and tried to kiss me. I kissed back a little, but he had a scruffy face and his stubble against skin was very uncomfortable. It really burst my bubble. I don't know what would have happened if he had been clean-shaven but I told him I didn't want to do that. He gave a little girlie pout which I found sexy in its own way, but he wasn't too discouraged because he asked if I would scoot over and he could get in bed with me. He was definitely looking for something oral, because in lieu of my face he started kissing my chest and eventually sucking on my right nipple

That got me back in the mood in a hurry. I was moaning and responding and that started an escalation of us both getting into things. For the first time, he touched my dick and I almost came right away. Side note: my cock is oozing with precum now as I recount this story in a fashion very similar to the way it was that night.

At this point I wasn't reciprocating much other than to put my hand on his side and rub back and forth as he continued to fondle my balls and stroke my cock. It wasn't so much that I wanted to please him as much as it was just a comfortable place for my hand to rest. I realize that I'm not quite describing this was well as I should, but I got the sense that he wanted to please me and perhaps be controlled a bit.

As I hope to tell in other stories in the future, I'd been with several men before, but had never done full on anal as either a giver or receiver and for the first time, I realized that might be a possibility for tonight. That's what I was starting to think I really wanted to achieve with this encounter. My mind couldn't help it go back to thinking of all my straight, homophobic friends and what they would think of me if they knew I was letting this little queer explore my body. I thought about what my girlfriend would think if she knew I was cheating on her, much less with a dude. God that kind of stuff just turns me on. I love doing things that are wrong. I didn't believe homosexuality was wrong in any kind of moral sense, but I knew people looked down on it and that's what I was getting into with what was happening right now.

Frank eventually began kissing his way down my stomach and he finally got to my dick. As before he started sniffing it as well as my balls and my taint with big whiffs. That had its own sense of dirtiness and reminded me of literally the girl-next-door from where I grew up. We had our own bizarre relationship where I was very subservient to her and often ate her dirty smelly asshole. I liked being in that role but tonight, I pictured him in that role and me as the almost disinterested object of desire who was lowering myself to let him please me. I knew I'd been up for over 24 hours at this point, sitting out in the sun, dancing and drinking, so my whole crotch was smelly and sweaty and he was loving it... and so was I.

I was trying to think how I could adjust our positions so that I could fuck him. He had other plans though, and finally took my cock in his mouth, giving me a really good blowjob. I'd only had a few blowjobs at this point in my life , more from dudes than from women. But this one was somehow the best. It was such a struggle. It felt so good that I didn't want him to stop, but I didn't want to come either. But, my inhibitions were, down my willpower was down, and I couldn't resist. I shot a massive load of come right down his throat. He didn't miss a beat and swallowed every drop.

As almost always happened in my male-male encounters, as soon as I blew my load, reality kicked back in and without the sexual tension it wasn't a dirty fantasy, it was just me and some dude lying naked on a bed with his slobber all over my dick. Normally, this is when I would have made my exit, but I was drunk, stoned, relaxed and spent. I closed my eyes for a moment and didn't wake up for several hours..

I woke up the next morning not really knowing where I was until the fog slowly lifted and I heard Frank's femmy voice greeting me good morning. I can't really explain how cloudy things felt in my mind. It was like I was still drunk and still in a haze about all that had happened the night before. At any rate he asked me if we were going to spend the day together. I wasn't sure how to respond because I knew the truth was that there was no way I was going to spend the day with this faggot, and he could never see me with my friends. My girlfriend, my military career, and everything about who I was not in line with spending the day on a date with a guy.

I just mumbled we'll see. He got back into bed with me and said maybe we could just spend the whole day here and that was the first twinge of horniness I felt coming back and I thought that might be a possibility. He leaned in to try to kiss me again. I didn't even use words; I just pushed him away. I wasn't even a push so much as a primitive nudge and grunt that let him know to stop. I could tell he was a little hurt and that gave me a bit of a rush, but he was undaunted. Instead of more kissing, he went back to what he knew had worked the night before, sucking my left nipple this time. I started having its intended effect. I was still stark naked and he was in a T-shirt and boxers.

I started feeling like the alpha male in some tribe and I realized that he wanted me to be that way. I started to take charge. I started remembering how, despite how good the blowjob felt, that I had missed my chance to fuck this little queer and I wasn't going to miss my chance again.

Be now he was sucking my dick again, but that wasn't going to be enough this time. So, with no words, I just sat up, pushed him back and rolled over on top of him. I started to pull down his shorts and slid them down his legs, which put my face in proximity with his crotch. At different times, I feel differently and there have certainly been times when I was the little sissy who wanted to be fed cock, but not this time. So, I just worked my way back up to get ready to fuck him He was sitting up and trying to remove his shirt, but that was just delaying me from getting what I was after, so I just pushed him back down and positioned myself between his legts.

He started to roll over and said he needed to get a condom. The thought briefly crossed my mind as this was in the 80s and AIDS was just becoming a concern, but the idea of risking it just raised the stakes and seemed hotter, so again, without words, I just pushed him back flat on the bed and started pushing my dick against his rosebud.

He said out loud, "Oh my God, it's been so long, I hope I can do it, and your cock is so big".

For the record it wasn't. Compared to him, maybe, but I'd been with enough guys to know it was average at best. But that didn't matter. The fact that he might not be ready didn't matter. I was going to take him and nothing was going to stop me.

He asked me to go slow which I also ignored. The only thing stopping me, partially due to my inexperience, was that my dry dick was having a hard time pushing into his dry butthole. I thought about rimming him for a while to lube him up with my spit but instead I just kept pushing against his hole. With each thrust, he didn't necessarily open up, but his entire bottom seemed to collapse, inviting me in. At the same time, I could feel my cock throbbing and with each throb just a bit more precum started working its way down my shaft. He said it wasn't feeling very good and started to squirm, but I was getting off on the power trip I was feeling from totally owning this guy, so I again pushed him back flat on the bed and said nothing. I just kept thrusting slowly, slowly, slowly. He knew his place and just resigned himself to his fate from that point forward.

Eventually enough precum built up between my dickhead and his hole that I started to enter him a little bit more with each thrust. It's so hard to be a good judge of time in situations like this but it felt like a painfully long time before I even got my head all the way into him.

Once I did though it just took two or three more thrusts and I was buried in him up to the hilt. It was a feeling like I'd never experienced before or sense. Even subsequent times when I would fuck men or women in the ass, it never felt quite as good as this, mainly because of the novelty, I suppose.

Whether it's a man or a woman though, nothing compares to that tight, all-encompassing grip and yet with such a soft touch, like a velvet glove surrounding your cock. He was breathing so heavy and started saying how good it felt and asking, then begging for me to kiss him. It showed he didn't completely understand that none of this was about him. He was just my little fucktoy, my thing to be owned.. He was there for my pleasure and nothing else. I felt like the King of the fucking planet, owning this other man, totally possessing him. It was an ultimate rush of power.

I just kept stroking and thrusting and thrusting in and out of his boy pussy. It sucked and pulled me in like a tractor beam.

As pleasurable it all felt this, for the first time I started to feel the effects of the drinking and sun and lack of sleep from the night before. A headache started as a dull pain, then became very acute. I was also realizing how dehydrated I was. I was getting a workout plowing into this quer, but I couldn't sweat to save my life. I wanted things to last longer but I knew I wouldn't be able to keep up this pace for long. I've read that some guys like to bury their cock when they come, but not me. I do like to go really, really slowly, but never stop completely. This way, you can sort of edge yourself and feel every single nerve ending get as close to the edge as you can possibly get. That's exactly how it went this time and when I finally came, it felt like it lasted forever. My dick and balls kept contracting and continued to pump and pump and pump. I don't even know if anything was coming out given how much I had come the night before, but felt like I was filling him to capacity. For those few seconds I didn't think about the headache with the dehydration or anything except how good my entire body felt, like I had just taken a hit of crack or something. And much like that, as soon as the high was over, I crashed. I was suddenly painfully aware of the bright Florida sunshine streaming in the windows and just lied down and covered my face with a pillow to get some relief.

Frank of course was still totally torqued up and he wanted to play some more. He started rubbing me with his hand and eventually, I felt him dry humping my leg. I didn't really mind at first until I felt a slick of precum that had developed along the path of his dick on my leg. I rolled my body with just enough force to topple him off me and he got the message.

He said he was going to take a shower to clean himself and then it could be his turn. I didn't want any part of that, so once I heard the shower running, I gathered up my clothes, got dressed and started to make my exit. I walked by a small table near the door and his keyring with about 30 keys on it. I wondered momentarily what he did for a living to have all those keys, but quickly decided I didn't give a fuck and grabbed them as I made my way out the door. I got my bearings and started heading to my hotel. I crossed a bridge as I walked and tossed his keys in the water. I felt bad about it, but what was I going to do at that point. I didn't have any way to get them back to him and wasn't going to bring them back to the hotel. I have felt bad about it over the years, but I figure that if you are a guy who cruises for drunk college frat boys in Key West during spring break, you know what you're getting into.

I'm married now and have never cheated on my wife, so it's been 30 years since I've been with a different man or woman. I have a decent sex life, but after that much time fucking just one person, you sometimes need a little help getting over the edge. So, there have been times when I'm not fucking my wife. I'm back in Key West, I'm 20 years old, I'm ripped, and I'm completely plowing a little faggot named Frank.

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