First time sex

by Tony

29 Feb 2024 4926 readers Score 7.0 (39 votes) PDF Mobi ePub Txt


This is the story of my first time having anal sex. I had hooked up with a few guys already at this point but it was all just oral and other things never actually done anal.

 So I am somewhere around 25 at this time, not sure exactly how old but it was somewhere around there. So one night I’m just hanging out not really doing anything, I’d had a couple drinks but I was bored and started thinking getting kind of horny and started to think about maybe hooking up. 

So I say fuck it I’ll sign into Grindr and just see what’s up on there, why not can’t hurt to look around. So I sign in and within a couple minutes I have a million messages (which happens every time I sign in on there I don’t even respond to most of them) But I see one catches my interest who is the same age as me and happens to be like right down the street. 
So we are talking for a few minutes and we are getting along pretty well. I told him that I’m looking to bottom, he says he’s looking to top. We exchange some pictures and we both like what we see. He tells me that he has the house to himself and I could go over there right now if I wanted. 

I decided fuck it why not, if I’m not into it when I get there and meet him I can say I’m sorry and leave. So I tell him that I want to come over and he sends me the address. I know exactly where that street is so I tell him I’m gonna take a quick shower and then I’ll head over, probably be there in a half hour or so. He just says ok message me when you’re here.

so after getting cleaned up I’m head over. Once I’m out front I message him saying that I’m there. He says to just walk up to the side door, when I get there I don’t even have to knock he is already there and I walk inside.

he is a pretty good looking guy, In pretty good shape. We hadn’t exchanged face pics just body shots so it’s a relief that he’s not totally ugly. So I follow him as he starts walking and he leads me into the living room where we sit down on the couch. He asks if I need anything and I said you know what I actually could use a water if you got one and he said sure and goes and gets one.

after I take a sip he says so do you want to hang out for a little bit or something. I said no I think I just wanna get tight to it. He says ok and moves over and starts kissing me. I kissed back for maybe like two seconds before pulling away and telling him I’m not really into kissing. He said ok that’s fine let’s just go to the bedroom now then. We get in there and he immediately starts undressing so I do the same. We climb in the bed and I move down towards his dick, which isn’t all the way hard yet but it’s already very nice looking. So after sucking it for a few minutes it’s fully hard. And to this day it is the best looking dick that I’ve ever seen in my life, before or since. It’s so nice that I’m going to town on it, blowing him for at least 10 minutes maybe 15. Eventually he says so do you still want me to fuck you, to which I said yes and he said well we should do it now then because if you keep sucking it let that I’m gonna cum before we get the chance.

so I said ok let’s do it and moved up next to him on the bed and rolled over onto my back. He got up and grabbed a condom from next to the bed and put it on. After lubing me a little bit he asked if I was ready and I said yes. 

So I’m really nervous but very excited at the same time because I’ve fantasized about this for a long time. He gets it in easier than I expected. I thought it was going to be more painful than it was too but it didn’t really hurt at all honestly, maybe because I was kinda drunk. So he just kept going for a few minutes, he picked up the pace as it went on but he was never very rough, he wasn’t trying to smash me or anything obviously. So after a few minutes he said he was about to cum and makes  a loud noise and then cums in my ass. I couldn’t feel it when it happened since he was wearing a condom. 

After he was done he took off the confom and said he needed a nap and rolled over and went to sleep. I waited there for a few minutes to see if he was gonna wake up or something but after getting no response from him for a while I got up got dressed and left.

 I never talked to or heard from him again after that lol.