I was 18 back in the year 2000. I was a horny bastard as most 18 year old guys are. I used to get my fair share of girls and had had sex a few times but never had fucked a girl in the ass.

I had actually broken up with my girlfriend because I had gotten cheated on about a week before prom so I asked a girl last minute if she would go with me. She was pretty good looking and we had made out a couple of times but we were just going as friends.

She was fun and we had a really good time. As most proms go, we all went back to a friends house afterwards and started partying. We drank pretty often in high school but nothing too crazy. She drank sometimes but never too much. Well as it starts getting later we’re hanging out and she sits on my lap. This wasn’t anything abnormal, we did this all the time back then. After a while I realized this might be changing our friendship a bit when she reached behind her back and started touching my dick. We were outside so no one could really see anything but I got immediately hard.
In my head I’m thinking “maybe she’ll jerk me off tonight.” I wasn’t expecting too much, I had never heard that she was slutty or anything.

We were friends and she had told me about a few things but never more than her giving a blowjob. Pretty standard for 18 year olds. We did talk about what made us horny sometimes but again we were just friends and had fun talking. Back then I remember calling her on my house phone and just talking for hours about dumb shit.

Anyway, she’s still rubbing my dick from behind and I have my hand around her waist, I think I was rubbing her waist with my fingers. I remember she was squirming a bit so I knew she was liking it. She had a sweatshirt on, that hung over her legs and ass so I decided to put my hand under her sweatshirt and inside her pants. I slowly inched my hand lower so that no one could see until I reached her pussy. She had told me before that she shaved her pussy so I wasn’t surprised to not feel any hair. Still though, thinking about it now it was fucking hot. She actually spread her legs a bit so I could touch her, but not too much so anyone would notice. I slowly put my finger in her pussy and spread her lips so I could finger her. She was wet when I finally got my fingers in. I moved my middle finger in and out as much as I could for a while, after a few minutes my fingers were soaked. I could tell she was loving it for obvious reasons, most of all when she whispered in my ear “let’s go take a walk.” I was drunk but not hammered or anything so I took my hand out from under her pants and we stood up.

My friends house was in a pretty wooded area so we just walked down the street a bit when she stopped and looked up at me and started kissing me. As we started kissing I took my hand and slipped it under her shirt and under her bra. She had nice tits, not gigantic or anything but firm 18 year old tit. Her nipples were so hard either from the cold or from being turned on. I’d like to think both. lol.

We made out like this for a while when I asked her to go behind some trees. I remember there was a giant rock in the trees so I took her there and we laid on the ground. It was pretty hot, just laying there together making out. I lifted her shirt up and started sucking on her tits. She was nervous, but I was too. I remember I asked her if she wanted to keep going and she nodded. After a while I slipped her pants down and started fingering her again, this time just a little harder. She was really really wet and she was breathing heavy. Neither of us were that experienced but I know we had talked about sex when we would talk on the phone. I remember after a while I asked her if she wanted to do more, she said yes. I didn’t have a condom, like I said I wasn’t expecting sex, so I actually told her to get on top of me while I laid on the ground. She took off her pants completely and straddled my face. I remember she was nervous, kind of breathing heavily and a little shaky, but also had an urge. She wanted more.

As she straddled my face she took my pants down too and started sucking my dick. I had never 69’d before so for 18year old me it was ecstasy. I tried hard not to show how horny I was but it was fucking hard! I’m in the woods, behind a rock, 69’ing with my friend, who I had never expected to be doing this with. I remember my hands were shaking. lol.

We 69’d for a while and in my head I kicked myself for not bringing a condom with. I had eaten pussy before so I kicked her clit and stuck my tongue in her pussy a bunch. It was so fucking hot. I remember at one point she asked if I had a condom but I shook my head no. I was horny as shit so I asked “do you want to try it a different way?” She responded “How?” I remember not being sure how to answer that so I stumbled through my words and said “uh, you know from behind.” She thought about it for a bit and actually said “okay.”

I remember sitting up and thinking “Holy shit, I wonder if this will work.” We were both pretty inexperienced, but I remember saying “maybe get on your hands and knees and I’ll try to put it in.” lol. Worst line ever but she must’ve been so horny that she said okay and got on all fours. I got on my knees behind her but I really couldn’t see anything, it was pretty dark. I grabbed my dick and used my tongue to get some saliva on my head and put it right on her asshole. I think I tried to just shove it in but it hurt her and she jumped a little. She said “try going slower.” So I licked my hands and put more saliva on my dick and put it on her asshole. I remember thinking “how the hell is this going to work?” So I decided to try and stick my finger in her ass. This was much easier. I stuck my finger in her ass slowly. She grunted a bit but didn’t tell me to stop. I had my finger up until the knuckle and started pushing it in and out. She was breathing hard so I guess she was okay and maybe enjoying it. I asked her if it hurt and she said “ A little but it’s okay.” I fingered her ass for a bit more, then started going a little harder. After a bit she said, “okay try putting it in again.” I was so fucking horny. I took my finger out of her ass slowly and put more saliva on my dick. This time I put it right on the edge of her asshole and slowly stuck it in. Again she was grunting and breathing hard but she didn’t say stop. She actually said “keep going.” I replied “are you sure?” And she nodded yes. I kept inching it in slowly until I had the head of my dick in her ass. I remember thinking in my head “holy fuck. My dick is in her ass.” I slowly pulled back then pushed in again. She kept breathing hard and would grunt but still we kept going. I’m sure it was hurting her, but she was game. After a while I started to go a bit faster, and it started to feel good for me. I think she was enjoying it, she moaned as I pushed it in and out. Each time I pumped I went a little deeper. Ugh, thinking about it now what a lucky mother fucker I was to ass fuck this girl. I fucked her in her ass for about 10 minutes but I wasn’t close to cumming. The next part is kind of funny. We heard some of our friends calling us. I was still inside of her but their voices kept getting closer. Finally she said “I think we need to stop.” I as disappointed but I didn’t want our friends to find me fucking her in the ass. I said okay and slowly took my dick out of her ass. She grunted again as I pulled it out, but never said anything about it hurting. We sat there for a bit then she out her underwear back on then her gray sweats. I put my clothes on too and I kissed her again before we stood up and headed back.

I will never forget that night. We never ended up hooking up again. We talked for a while, thinking maybe we would get together but we never we did. Summer before college was coming and we ended up heading off to college. We saw each other a bunch over our college years and only one time did I bring that up. We both laughed about it and she said it was a fun hook up that night. I remember she said her ass hurt for a few days after that. We both laughed and said “of course it did, why the fuck did we have butt sex?” She laughed and looked me in the eye and said “It was fun.”. We are both married with kids now, and I haven’t seen her in like 15 years, but I will never forget when I ass fucked her that night in the woods. I have my 25 year reunion coming up this year. I hope she’s there. I kind of want to talk about it again all these years later.

JMary(almost her name). We had a great horny prom hook up that I will never ever forget. I hope you remember that night if you ever have anal with your husband.

100% true story. Feel free to message with any questions. Would be glad to answer any and all.