Video Booth: Lost My Anal Cherry At 20 (Part 1)

I was going to a university in a large Midwestern city and driving for Domino's. White male, 20, with a live-in girlfriend who I'd lost my virginity to in the spring semester. Over the summer I passed an adult bookstore that was in the seedier, older part of town, and after several days of working up my courage to even just go inside, I finally did. At that time I didn't know anything about video booths, just that I might buy a dirty magazine or VHS tape.

So I'm inside and see a sign about "video booths" in the back. I ducked my head through the curtain, but saw a guy so I left. But curiosity got the better of me and in a day or two I was back. Dropped some quarters in the slot, picked a video (I saw the gay ones in the menu, but chose a guy-girl one because that was weird to me), dropped my pants, and proceeded to jack off to this new-found wonder.

That's when I saw a hand through the fairly large hole waving me over. He said to stick my dick through and he would suck it. I did and he did, and it felt great. But before I came he pulled off and stuck his own dick through and asked if I wanted to play with it. Now, before I came in the place I'd have said "hell no," but now I was horny as heck and it seemed alright to just touch it, then maybe he'd go back to sucking me and finish me off. You know how it goes from there: he said I could kiss it if I wanted, so I did, but I didn't suck it. So then he pulled me back through the hole and got me really close, but stopping and sticking his dick back through. They do that to get you worked up to where you'll suck it, and I did. But I didn't want him coming in my mouth or even in front of me, so after a while I stopped. But he was nice and took me back in his mouth, finishing me off and keeping my dick in his mouth until I was more than done.

Then shame at what I'd done kicked in and I thanked him and pulled up my pants and mostly ran out of there. But of course I was hooked, and the feeling of his dick in my mouth made me want another one. And maybe even suck it to completion like he'd done me. So I started coming back, late after work, more to give blowjobs than get them. One guy had come in my booth one time and he put on some gay porn, sucking and fucking. As he was sucking me he asked if I might like something like that (the buttfucking), but I wasn't sure if he meant me giving or receiving. I didn't think I was too interested in giving, but that I might like receiving. I think he sensed that, because when I was on my knees sucking him, some twink (I didn't know the term at the time, but that's what I was: 20yo, 5' 11", 150#, and not too hairy) was getting pounded by a fat cock and he was saying how he'd like to be doing that to me right now. I didn't let him do that, but I did let him come in my mouth, and then he left without finishing me. Rude.

So then I started thinking about taking a dick up my butt, and somehow I knew enough to know that you were supposed to enema. So I bought some of those Fleet enemas and some condoms and lube, and one day when my girlfriend was at work gave myself two enemas. After work that night I went into the ABS with the condoms tucked in one sock and the bottle of lube in the other. Picking a booth, I waited for a dick to come through the hole. When it did I sucked it, but when I asked if he wanted to suck me he said no. So I finished him in my mouth and waited for the next guy.

Now, I didn't know this at the time, but when you're young and inexperienced (and cute?) all the older guys want to have a go at you. So it was only a moment after the first guy left that another one entered. He stuck his dick through and I got to sucking. But he didn't want my butt either, so after trading BJs back and forth for a little bit, I let him cum in my mouth. I sucked the next guy, and when I showed him a condom and the lube he snatched it from me and had that condom on and lubed in no time. I pushed my sphincter back against the hole and felt the cold, slippery head of his dick rooting around back there, and finally he got it in a little, but only a little. And after just a few pumps he was done, I could feel it swelling and pulsing in my butt. He left quickly. And that's how I lost my anal cherry.

Another guy in, another dick through the hole, more sucking, and when I asked if he wanted to fuck me he said he did, but could he come in my booth. I was scared so I said no, but he fucked me through the hole for several minutes. Long enough that my asshole started burning-like. I was rock hard and stroking myself, but I guess I didn't know then that you're supposed to try to come when the guy in your ass comes. I was thinking that like the times before I'd get someone to suck me off to completion. So he came and it felt better this time because he was buried all the way in me. When he pulled out I turned to put my dick through the hole, be he'd left already.

(Only 5k characters allowed, so "to be continued.")