This is the story of my first time ever with another man.
When I look back on it, I think that this whole thing started on the night of my
friend's Bar Mitzvah. At this point, I was nineteen and was about 5' 10"
tall. I was well built, had pretty strong legs and worked out regularly, so I had pretty
big muscles.
My friend, Josh, was eighteen, and a bit shorter than I. He was about 5'
8" and had a sprinter's body. His parents had let him have a few friends over
for a sleepover that night. At first it started out as a typical young guys'
sleepover. We played video games, and we drank a little beer.
I had been looking at every type of porn for about a year at this point, with a
liking for gay porn best. Around midnight, Josh's parents went to bed. At this point,
we were a bit intoxicated and started getting horny. It started out with the three of us,
myself, Josh, and our other friend, Chris, all striping down into our shirts and
underwear. I remember that I was wearing blue boxer briefs, and Chris was wearing
blue-green boxers. Josh was wearing red briefs.
At first we were just goofing around, daring each other to touch each other's
dicks through our underwear. Then, we started getting a little hornier and started
mooning each other, and pulling down Chris's boxers to expose his butt.
Then Josh dared me to hump his bare butt. I jokingly asked if I should put my bare
dick on his butt. He said no, just do it through my boxers. Well that wasn't going to
stop me. Chris didn't want to see this, so he turned off the lights in the basement,
and Josh went onto the couch and put his butt in the air. Little did either of them know
that as soon as the lights went out, I pulled my stiff member out and was getting ready to
use it.
I had seen anal sex before but didn't know that you needed lubrication. So
what happened was I rubbed my stiff cock against his butt crack and started trying to
force it in. At first he didn't say anything, but then he said to stop, and that that
was enough of that. So I quickly pulled my briefs up just as the lights were coming up.
We didn't talk about it for the rest of the night. That was the very first
time I had every done anything with a guy, and I couldn't get it out of my mind.
Fast forward three weeks later. I got a call from Josh again, asking if I wanted to have
another sleepover at his house. I said sure and asked what time. I was planning on jacking
off, but I half-expected something to happen, so I had held off.
When I got to Josh's, it was pretty much like any typical sleepover before. We
had pizza, watched some crappy movie, and played video games until 12:30. While we were
sitting there playing Super Smash Bros., Josh lost and said that he was bored.
So I said, "Well, what do you want to do?"
He replied that he wanted to do something like what we had done three weeks
earlier.
I thought about masturbating each other, so I suggested it to him, and he said that
he wasn't sure what masturbation was; he was really a sheltered kid! I said to him
that I would show him, but he had to take off his shorts first. He said okay, but first he
had to dim the lights. So I let him do that, and he pulled down his shorts to reveal
Hawaiian-themed boxers.
I told him to sit next to me on the couch and to spread his legs apart. As he was
sitting down, I noticed a slight poke in his boxers, signaling that it was a good time to
start. So I said to him that masturbating was a way of making yourself feel good by
rubbing your dick. He nodded and asked me to show him.
I said all right and grabbed his cock through his boxers. I started rubbing his
dick, and he began moaning. I rubbed his penis for about a minute and then stopped and
said that that was masturbating. I told him that if he wanted me to do anything else, that
he would have to do the same. So he reluctantly agreed and grabbed my hard dick and
wrapped his hand around it.
His first words were, "Holy shit, your dick is HUGE!"
I laughed and said that I was lucky. So he slowly started jacking me off, and I
went back to doing it to him. We sat there for a good ten minutes, slowly jacking each
other off, until suddenly Josh said to stop, that he was going to pee. I said that we were
getting close to the best part, but he wouldn't have it. He stopped jacking me off
and pulled away.
He went back over and turned on the lights. It was at this point that I noticed
that he had a slight wet spot on his boxers.
”Come on, lets see it," I said.
"What?"
"Your dick!" I replied.
He pulled his boxers back to show me his dick, and then he pulled the boxers up and
said that he had to go to the bathroom. I knew what he was doing in there, so I finished
off myself.
We didn't talk about it the next day, but a week later I got another request for a
sleepover. This time, I said that it should be at my house. So he came over, same formula,
pizza, movie, video games, blah, blah, blah. At about 1:00 a.m. I asked Josh if he wanted
to do that thing again. And he said yeah, but this time we should do it without boxers. As
soon as he said that my dick went rock hard. We pulled down our pants and boxers to reveal
our hard cocks. He looked at mine and said, that it really was big. I replied that his was
pretty big too...even though it wasn't.
So we started jerking each other off. We were both groaning and moaning. It felt a
hundred times better than doing it yourself. Suddenly I noticed that Josh's breathing
had quickened and that he was thrusting his hips slightly. I looked over at him to see if
he wanted to stop, but his eyes were shut.
Suddenly his hips thrust forward and out came the most cum I had ever seen in my
life, apart from my own first time. It got all over him, his dick, my hand, everywhere. He
stopped and said that he had had enough. But I said, "C'mon, you've still
got to do me."
So he said okay and jacked me off until I came. So there we were sitting in a
puddle of cum, both having just given our first full hand job to another guy. The air was
filled with the smell of our sperm.
We didn't say a word and instead just grabbed some tissues and cleaned
ourselves up. We went to bed and slept in each other's arms.
A week later, he called to see if I wanted to hang out for the afternoon. I went
over and found out that his parents were going to the airport to pick up his brothers from
college. So he and I went downstairs and stripped down completely. Then Josh said that he
had heard of something called oral sex. I decided to play dumb.
He told me that it was when someone either got their dick sucked on or sucked
another dick. He asked me if I wanted to try it with him. I said, "Sure, why
not?" and I agreed to suck Josh's dick first. He sat down on the couch and I
moved my mouth toward his cock and then engulfed it. The taste of his cock was incredible.
It was like a mixture of a non-greasy sausage with a slight salty taste.
He started moaning and groaning as I kept sucking. After about five minutes, he
said, "Oh God, I'm gonna cum!" And he started thrusting his hips forward,
and suddenly let out this high-pitched yelp, and I felt the cum gush out of his cock. This
was my first time ever tasting cum, and I have to say that it tasted great! It tasted a
bit like unsweetened eggnog. I swallowed it. Mmm.
I let Josh cool down and told him that a promise was a promise. So I sat down and
he kneeled down and started sucking on my cock. At first, he wasn't all that good,
mainly because he couldn't get it down, but he slowly found a way to get it in. That
was probably the best feeling that I have ever had. It really is indescribable how it felt
to have my dick sucked. I came right inside of Josh's mouth, and he swallowed it all.
We got really lucky, because right as we had both gotten our clothes on, his parents came
back, and I had to go home.
Unfortunately, by this point, it was mid-November, just about to be winter time,
and we lived on opposite ends of town, so it made it hard to do any sleepovers. But one
night, about a week after Christmas, Josh said that he could have a sleepover at his
house. I jumped at the idea of another night with Josh. So when I got over to his house,
it was same routine.
Around ten, Josh said that once his parents went to bed he had something special.
Around twelve, his parents went to bed and he said that he would be right back. He went
over to his brother's room and came out a minute later holding a CD. I asked him what
shitty CD we were going to watch, and he said to just wait. He put the CD in and hit play.
He told me to turn around so he could get to a certain point. After about a minute, Josh
told me to turn around. I did and was immediately hit with a video of two guys making out
on a table. He said that his brother had this in his room and that he had watched it and
wanted to try some things. I already had a pretty good idea what "things" were,
but I asked what. He said that he wanted to fuck me. I hid my enthusiasm pretty well and
asked him if he knew how. He said that his brother had told him what to do and had even
shown him how. So I said all right.
He reached over and grabbed my crotch and started rubbing it. Instinctively, I
reached for his. We sat down, rubbing each other's crotches. Then he stopped and
stood up. He took off his shirt and his shorts to reveal a very tight pair of light blue
briefs. I grabbed my shorts and yanked them down and took off my shirt and revealed to him
my red boxers.
He sat down on my lap and leaned in closer to my face. I knew what was coming, so I
opened my mouth and sure enough, his tongue slipped right into my mouth. I don't know
how long we sat there just kissing, but eventually, I stopped and slowly pulled down his
briefs. I revealed his penis, standing at attention, waiting to do anything.
I got down on my knees, but Josh said, "No, no blowjobs."
So, I knew exactly what that meant. I managed to stammer, "Do you want to fuck
me?"
He nodded and grabbed the CVS bag and pulled out a jar of Vaseline.
He asked, "Do you know what to do?"
"Of course," I replied.
So, he pulled down his briefs and got on the couch on all fours, doggy style.
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