X/post from /r/bigonewildstories

Quick preface, I’m happily married (to a woman) but I certainly had my share of same sex experiences. I haven’t been with a guy since I got married, but who knows what the future brings.

This is the story of the first time I got fucked by another guy.

So I’m about 20-21 at the time (this is like… man ~ 15 yrs ago)… about 5’11, 180lbs (a muscular 180 actually. I had just ended a long term relationship and started hitting the weights hard) and 7″ cut.

I’m craving cock again and surf to my go to back then, gay.com. Once again, the usual start to message me. Much older guys, out of shape guys, sketchy guys… anyway…. After a while this guy about 23ish or so messages me and lives kind of close. He’s attractive enough… but of a thin build and plain face but certainly not hard on the eyes.

Any who.. we’re chatting it up about our likes and dislikes.. and it’s getting kind of steamy. I start to gather this guy’s really more bi-curious then gay or bisexual. He doesn’t want to get fucked, doesn’t want to suck cock but sure wants to get blown and fuck someone.

Look, I could detail out this back story more but you’re holding your cock; or rubbing your clit and delaying what you’re here for. Long and short, I found a match. I’ve only sucked cock to this point in life but I’m uber curious for more and have done a lot of “personal’ ass play up to this point in life. Even a failed “take it from a guy” attempt (Another story, another day). I can’t remember dude’s name for the life of me, so we’ll call him Chad.

Chad lives about 15 minutes away and Chad’s on his way.

So he gets to my place, he’s about what I expected and I could tell pretty nervous. We have a few quick minutes of small talk, but I figure let’s get the nervous out of him so I push him down onto the couch.

I start kissing and making out with him. At first he’s not quite into it but that turns around pretty quick. I begin to unbuckle his pants and them and his underwear down while still making out. His cock is still pretty soft- he’s definitely nervous. As I’m slowly massaging and jerking it doesn’t take too long to get him hard. Chad’s about 5’8” maybe… 160 lbs.. and only about 6” cut and sort of thin. I love this though because I think it’ll be good for my first time “taking it”

After a few more minutes of that, he starts to undo and pull my pants and underwear down too. I stand up to remove them completely and his as well. They were only around his knees. I give him a few quick kisses and then get on my knees, lean over the couch and take his cock in my mouth. I tease a little at first but it’s not long until I’ve got as much as I can fit in my mouth. He puts his hand on the back of my head and I’m giving him the sloppiest, wettest blowjob I’ve ever given a guy. Chad’s loving it! Several minutes pass, I don’t want him to cum quite yet so I get up and straddle him to resume making out.

While our tongues are dancing against each other, he starts to rub his sloppy (thanks to me!) head against my hole. He’s not yet trying to get inside so I let him continue for a minute or so while we’re making out. Once it becomes apparent that he’s ready, I quickly rush off and get a condom from my room. While I’m in there I quickly grab a pull of lube and give myself a quick once over.

I return to the living room, tear open and put the condom on Chad’s cock. He’s still rock hard. I resume my straddling position and begin to make out with him again all the while he positions his cock pointed right at my hole. I slowly start to push back and he pushes up in small little thrusts. It doesn’t hurt one bit! The pace begins to quicken until he’s all the way inside me.. This feels AMAZING!

I sit up and slowly start to ride. Chad grabs a hold of my hips while I start to slowly start to bounce on his perfectly sized (for me) cock. It feels so good that I start to jerk myself off slowly while riding. Chad I think liked his new experiences, as he starts to thrust deep and hard as best he could in his position. Although I’m riding him, he’s fucking me like a champ from his position. It doesn’t take long and his breath quickens, his thrusts go deeper and he feels just a little bit bigger and begins to moan. Despite the condom, I could feel him cumming in me. I loved it! I rode back as hard and deep as I could until he was done, the look on his face said it all.

Now, I’m close…. Real close. I could tell Chad had enough “new experiences” and just wanted to finish and go home now.. (c’mon guys.. you know the feeling after a hard cum) but nope… he wasn’t going to blow me (know going in) or let me fuck him (same deal) then I’ll do it myself and he’ll deal with it.

Chad’s now… almost flaccid cock is still in my ass (and still felt pretty good) and I’m giving my cock a real good tug. I’m trying to rock back and forth a bit, because I really wanted that prostate pressure when I cum. After only a minute or so he gets kind of semi hard and it’s all I need to finish the job. I must have had a good 4 or 5 solid jets when I came… 2 landed on his face… I’m sure some of it in his mouth. The feeling was like nothing I’ve had before.

He didn’t want any part of kissing or anything after, I don’t think he regretted it but think he knew what to do next. After I climbed off, he went to the bathroom and cleaned up. He came out and got dressed and we had a few words of small talk again and he left.

I never heard from him again, but that’s the first time I had a cock up my ass.

This story was originally published here

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