Take, for example, this past winter break. Darryl is a close friend of one my good friends. He is also fabulously gay and I find him to be fantastically hot.
This is not Darryl, but he's similar enough for our purposes:
For more of this story and for more images of hot naked boys, please continue after the jump.
Darryl goes to college in my hometown but is originally from somewhere in the middle of nowhere. Let's say Nebraska or Kansas or Iowa or something. He's a short, skinny emo kid who is constantly changing his hair color and carefully removes every single hair he has below the neck. And whatever grows on his face. Our mutual friend, rather uncharitably describing my taste in boys as "those who can pass as 12 year olds," and knowing, for reasons to be told in a later story, of the immense size of my cock and Darryl's love for immense cocks, thought that we should get in touch. And probably fuck.
In the early hours of the morning of November 20th, 2010, Darryl and I chatted on skype for a few hours. One thing led to another, and we stripped and then jacked off on cam for each other. After that, we compared schedules, and realized that we wouldn't be in the same city together until the tail end of my winter break when I would still be home and he'd be coming back to school.
We tentatively made plans to get together then and chatted a few times in the couple months that followed. All seemed relatively well.
I returned home for winter break on December 20th, and immediately I realized that I had no gay friends with whom I could hook up with until Darryl arrived. As for girls back at home, the only one I had a chance at was my ex-girlfriend, Mei, who was in town for a week, but she had no desire to sleep with me. Though, we did see a couple plays together, grab some meals, go shopping, and she even spent a night at my house. I have a nagging suspicion that this is what marriage is like.
To satiate my eternal lust, I went online to search for possible hook-ups the minute I returned home. The first one to come up with any real promise was Neil. Though not exactly my type, he was reasonably cute, lived nearby, and was fun to talk to. He also, conveniently, was the only one of his housemates in his house for the holidays.
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| Not Neil, but close enough. |
We made plans for me to come over early the next morning on the 21st. I was going to the library near his house that morning anyways, and morning sex is always fantastic. I arrived at his house at the time we agreed to and spent 20 minutes stamping my feet in the cold, knocking on every entrance to the building I could find, and generally freezing my balls off. Cold and decidedly unhorny at that point, I went to the library.
That night, Neil messaged me on skype. He explained that he had slipped on some ice and had spent the day in the hospital. I told him that I'd be in the library reading for the next day. If he wanted me to come over, he could text me. He never texted me.
I spent the next week hanging out with friends and my ex-girlfriend, seeing plays, shopping, enjoying Christmas, forcing my friends to play me in a complex variation of Go I had developed, and generally enjoyed life.
After the new year, though, I felt myself longing to fuck someone, so I once again went online, waiting for Darryl to return to school.
On January 2nd, I talked with a boy named Lucius who lived in the midwest but went to school in my hometown and was coming back the 8th. He was thin and short, 5'7 and 130 lbs with dark blond hair.
And on January 3rd, I talked with a boy named Allan who lived very close to me and was home for break until he had to return to his state school. Dark haired, short, and horny, he was also a good opportunity and told me in great detail how he wanted me to fuck his ass. Within a couple days, I had three likely hook ups in the coming weak and was contented that I would get plenty of ass before I returned to school on the 9th.
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| Again, not actually Allan... you get the idea at this point. |
But Allan never contacted me again, and my attempts to reach him elicited no reply. Darryl, who was back in town, didn't contact me. I found through our mutual friend that he wasn't interested anymore. And then, on the 8th, Lucius told me that his flight was moved and he wasn't coming back until the 9th.
Fortunately, the story doesn't end there. I had an argument with my parents that ended in me deciding to take the greyhound back to school. Since the 10th was cheaper than the 9th, I delayed my return and had another shot at Lucius.
So, we agreed that he would call me when he got to campus, which he estimated would be sometime between 2 pm and 6 pm.
At 3 pm, I texted him and received no reply. At 6 pm, I called him and left a message. Finally, at 7:40, I sent him a message saying "not meaning to spam you... ... but in the remote possibility that you lost your phone or something, but let me know when you're back on campus." Despite the horrible grammatical mistakes, I left it at that. I then walked my dog with my dad, skyped with my sister, and fell asleep. At 12:19, on the morning of the 10th, I checked my computer again.
Lucius had messaged me at 12:18:
"you hit the nail on the head. i left my phone in the car on accident when my parents dropped me off at the airport. it must have fallen out of my pocket.... and then i went to check in at the airport, and the lady at the counter wouldn't check me in at first without paying a $150 service charge for switching the date of my flight, even though i was expressly told on the phone that there would be no fee... so she finally checked me in... only because she was such a stubborn bitch at first, she made me miss my flight... and of course i couldn't call anyone to help me get things sorted out... so i talked to a different and much more helpful representative who got me on a later flight. i finally got into pittsburgh tonight and nowwww im back on campus, with a migraine (probably from not eating)...... i'd call that an epic win of a day."
We spent the next several minutes chatting as I packed my bag for school.
So by, 12:40 am, we agreed I was coming over, possibly for gentler, lower key sex.
We met up, stripped down to our underpants (boxers for me, boxer briefs for him) climbed into his bunk (which is over his desk), and lay next to each other, gently kissing each other before exploring each other's bodies with our hands.
After a few minutes, I began working my way down his body with my mouth, teasing his nipples, rubbing my face against his stomach, eventually stripping off his shorts and sucking his dick.
Lucius is 5'7, 130ish lbs, thin, with a smooth, mostly hairless body. Armpit hair, of course, and a little bit of scruff on the face from not shaving. Dark blond hair, mostly. He shaved his pubes. I asked him if he preferred them shaved, he said honestly, he thinks it's a waste of time, but other guys like it, so he does it. It did look good on him. His dick was small in comparison to mine... they all are, so I'll say he's average in size with a small pair of nuts in a tight sack.
I brought him to the edge of cumming before he made me stop.
"I don't want to cum yet"
"I wasn't about to let you"
We rolled over so I was on my back and he lay on top of me, rubbing his dick against my thigh as we kissed and I caressed his perfect, gorgeous ass. I ran my fingers along his hole, and asked him if he wanted me to fuck him. He handed me a bottle of KY, and I slipped a finger inside his hole. Then another. Then one more. After fingering him with three fingers, I thought he was ready. He put a condom on me, and he lay on his stomach as I got up behind him. I plunged my dick into ass quickly. Too quickly, he flinched in pain and I took it out. I apologized, and found that my aggressive stroke had caused him to tighten up again. So, I took my time to finger him again, this time working up to four fingers. At this point, I had gotten soft, so after trying to fuck him with my soft dick (it doesn't work), I took off the condom, got myself hard, put it back on, and slipped the tip in. I paused, and waited for him to adjust, and slowly fucked him as he lay on his stomach.
Then, I flipped him onto his back, hooked an arm behind his left knee, and fucked him that way.
Then we fucked lying on our right sides, my arms wrapped around him to hold him in position. At that point, he decided we needed more lube, but the KY bottle had been knocked off by the seismic activities of the bed, so he jumped down to get it.
When he came back up, I lay on my back, and he rode my dick cowboy style before finally cumming on my chest.
After that, his head was spinning, either from the migraine or the dicking he just received, so we lay next to each other and spooned.
After dozing off for a little bit, I woke up and woke him up by jacking him off with my left hand. He returned the favor, and then we switched to our own hands. He came first. I, held down by my legendary endurance, took forever, but when I finally did come, it was while on my knees overlooking him, and splattering his chest, face, sheets, and pillow. I cum alot. While we were jacking it, we talked. I was his 9th, his first was May 2010, a boy in his high school. He is my 12th boy, and it's been 402 days since I slept with Alex.
We then spent the rest of the night cuddling together, forgoing covers as our bodies were warm enough, although eventually the cold caught up to us, and we pulled the covers halfway up.
At 6:00 am, the alarm went off, and i hustled out of bed, he did as well. I enjoyed the sight of his naked body in the early morning as I pulled on my clothes, and let me out. By 6:10, I was out the door.
I had been home for three weeks. I had hit on an absurd number of boys. Four of them, I had been likely to fuck. But only through what can be considered an absurdly fortunate coincidence was I able to fuck one of them, and that was literally at the last minute. That's the frustrating thing about hooking up. There are a vast number of rejections, missed opportunities, and seemingly divine interventions all for the chance of a few hours at most of sex. Is it worth it?
Hell yes. Lucius has one of the finest asses I've ever seen, and it was a fantastic pleasure to fuck it.
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