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Cancun + Best Friend

Posted by: Author: Age: 28 Posted on: 2 comments
3 likes 1534 views Category: Masturbation Male-Male Tags:


Finally decided to write this story of very well treasured memories and jealously guarded. If you stay with me, I bet you will be delighted.

Picture this, two guys meeting for the first time in high-school, few months later they become best friends, both 6' slim and not bad looking, both straight by the way. He was kind of a loner, I was the kind of socially unique open, friendly, but reserved guy, if you get what I'm trying to say.

The first semi-nudity encounter, which might not me much for many of you, was when I slept over at his house and had to change into our PJs so we stripped to our boxers. Very exciting for me at the time.

Few months later he invited me over to his family's apartment, right next to the beach. Well things are getting more interesting in this story. So, back at the apartment, only three remarkable things happened: saw him in his briefs (first time ever) and took a few pictures of him (non-digital camera, I can't imagine the face of the clerk while developing the film), picked the bathroom door while he was showering and got to see his nice ass, and saw his brother's hairless penis and balls under the leg opening of his PJs shorts.

Now here's the best part, that keeps my penis hard every time I go back to these moments. Let's set this story in our HS sophomore year, more precisely, summer.

We decided to go to Cancun and stay at my friends house where only one room was available and a full size bed (don't get ahead, well if you must, yes, this played a key factor). First day we decided to go to the beach so I told him to turn back as I was going to get my swim suit on, and he said the same to me with a shy smile, and I took a chance to look down under his butt to see a glimpse of his ball sack, I almost get a full erection.

Back from the beach, 6pm. As you can imagine, Cancun is really hot, so we decided to stay in our briefs, and yes, me with semi boner and leaking pre-cum. So I was there, laying my head on his stomach three inches from his bulge, admiring it, and 'accidentally' brushing my lips in his undies.

Out of the blue I tell Greg, hey we are really good friends we should be comfortable naked around each other. He was shocked, blushed and said mmmm no.

Me: but were very close, there should be no problem, we're both guys.

Greg: yes but I don't feel comfortable.

Me: come on!

Greg: ok, you first.

I then pull my briefs down exposing my semi hard penis. His face, priceless, blushed and shyness all over it. He then proceeded to pull his down. Wow, wow, now there's a tingly sensation in by balls, penis, stomach, heart racing.

Me: see, we're the same.

We then lay down.

Me: Can I touch you?

Greg: Why?

Me: Just because.

Greg: Ok, but if I get an erection don't you think it is because of something else, I believe he was referring to not think because he was gay-ly attracted

This got me really excited, I don't remember if mine grew to a full hard on.

Me: Yeah, I know! Happens to me too! I'm a dude!

But by the time I, with all excitement in the world, I touched his soft penis, mine was fully hard, and his was growing hard. Wow, what a memory.

We were both enjoying the experience. We're both uncut but his foreskin couldn't fully retract. Then told him if he was ever able to fully retract his tight foreskin, he just said 'sometimes'.

I told him he could touch mine too. He just quickly grabbed it with his thumb and two fingers, only two strokes.

Me: Greg, can I just grab you while you're sleeping to see if I can retract it?

And he said yes (yey!). All night I was thinking about grabbing him again, by 2am or so, I guess, I grabbed his dick and tried to retract his foreskin but he got hard really fast.

Next day 8pm, just coming from the beach, we're back in our room, get naked, laid on the bed. My fingers started to make him hard again. While I was still playing he shyishly asked some question regarding amount of sperm ejaculated, so cute of him. I slowly kept playing with his awesome dick, six inches just as mine, but his penis when erect, points right up on the stomach, mine points to the front, 90 degrees from the balls, I told him that was because the way he position his dick in his briefs when he was a kid. Anyway I kept playing with his dick very slowly until, all of the sudden, he cummed shooting in the air, his stomach, my hand. He quickly stood up to clean himself and handed me a kleenex. I told him I was sorry, that it wasn't my intention. He didn't reply, he was sort of ashamed but I insisted he shouldn't be. Wow, what an experience, next morning I was beating it in the shower with the best orgasm ever so far.

We then had some free nights in a nice hotel, with by fate the only rooms available were with only one king bed. I said, wow, fate understand my teen horniness. So many nude nights, but just one was amazing, extraordinary. My ever curiosity lead me to play with his genitals, brushing his balls and asking him if it tickled, hahahaha, and he did the same. I went back to the stroking motion, out of the blue he said:

Greg: but we're going to make a mess.

Me: who cares?

Greg: let me turn off the TV.

Me: leave it on a music channel.

We started stroking, I made a move, bring our dicks together, he loved it. Our pelvises were together, legs interleaved, I twitched my penis he then twitched his. We kept stroking, he came, I came. What an orgasm!!! Then we headed to the shower to get clean, so erotic.

Later that day, while packing, I brushed his ass with my dick (with drops pre-cum of course), he got an erection and walked around with his typical shy smile and his penis pointing straight up, I'll never forget that.

Weeks later we talked about it, he said that what we did was gay and he regretted it. I didn't, I don't.

A year later we went back to his apartment, and I insisted in doing it again, several times, but he didn't want to. Even when he came over to my house, he wouldn't accept.

Friendship was not the same since then, not sure if because of the Cancun experience or why. But I still get excited every time I remember this.



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