This is a moment that probably tops the leaderboards for both my me at my horniest and my scummiest, and I’ve been asked to write out more details about it before, so here goes nothing…
This was in the Spring of 2010. I was a college junior, but I was living close enough to my home town that my social circle (and dating pool) lined up enough with typical social places in my small home town. Which usually meant churches. I caught the eye of a Baptist girl while doing a social event, we started talking, and I found her cute. She was 19, a bit younger than me, but it didn’t take long for us to become interested in dating.
After asking her dad if he’d be OK with us dating (he gave a reserved yes), I learned a well-kept (or maybe not so well-kept?) secret about Baptist girls: They are freaky as hell. Despite being in such a conservative environment, she had no issues sneaking around and fucking around. I quickly discovered all sorts of creative ways of having sex out of the eyes of her conservative parents. We’d wait until her parents weren’t home, or head back to my dorm (under the guise of “seeing a movie”), or sneak into the bathroom of a public place. She loved giving and receiving head, and we tried basically every position in the back half of the Kama Sutra. She basically admitted that she isn’t especially loyal to the aspects of the faith about keeping chaste, though she’d never say that to her parents, who blissfully assumed she was a virgin.
But as the initial euphoria that came with us starting to date wore off, and I realized we didn’t have a ton in common. She had completely different life goals (wanted to live in our small town forever), different interests, and very little chemistry whenever we weren’t having sex. I found real date-dates with her to be a chore, and eventually I made the internal decision that the next time I saw her, I’d have to break the news that we weren’t going to work out long-term.
The evening I planned to do the break-up, I picked her up in my car that evening and planned on taking her to a church event. But hormones decided to intervene in my plans: We barely got a few block from her house, when she started to fuck with me, rubbing her hands over my crotch and teasing about giving me road head. It’s a breakup-date, I shouldn’t indulge this, should I? But I do. At a certain point, my dick takes control of the situation: I undo my pants and she’s stroking me. We’re out in the country, and I spot a side-road that I suspect isn’t well travelled. It’s getting dark, and I know we won’t be seen. I chance it, pull off, and invite her into the backseat of my (small, cramped) car.
It took maybe 90 seconds for us to get back, get a condom on, and start going at it doggy style. I kept telling myself I’d break the news to her after we were finished. She gives me an offer I find hard to refuse: “You know, we can try putting it in my ass if you wanted.” Besides fingers, I knew she’d never done that before… hell, at that point, _I’d_ never done it before. Hmm. I laugh, trying to put the brakes on the situation, slowing myself down and implicitly refusing her offer. But she continues to tease, spreading her cheeks. “I actually really want it,” she tells me. Fuck it – we’re already doing it. Why not go out with some final, triumphant assfucking?
So I dive in, offering a simple “tell me if it hurts too much” as I move my cock up and press it against her star. As soon as the head got in, she asked me to slow down. Getting myself situated was quite a task – turns out a cock is a lot harder to get in there than fingers – but as soon as I could get myself and her both comfortable, I started to pump.
I could certainly tell it hurt, but not to a degree of “too much.” She moaned and squealed the whole time, but after maybe half a minute, she was already playing with herself, rubbing her clit as I started to pump faster and faster. The whole time, I was one-third ecstatic (it felt incredible), one-third nervous about being caught, and one-third pondering what would come after I did. I felt myself building to a climax. My thrusts got faster, and so did her motions. We were hitting a point of almost cumming at the same time. “You can cum anywhere you like,” she tells me amidst deep breaths, before hitting an orgasm herself, quivering. Still wearing the condom and feeling myself close to finishing, I pull myself out (prompting an “AH!” from her) and slip the condom off, then stroke myself quickly and cum right on the surface of her asshole. It was the most I’d came in ages, and a huge mess. She teased me about it, and asked that I clean her up with wipes (I was happy to).
After a very short cuddle break, she was worried about being late, so we were on her way. With endorphins still rushing through me, I decide to take the plunge and just tell her what’s up. That we probably won’t work out long term, that it’d be better if we called it good then and there. She was understandably upset, started crying, and asked that I just drop her off and she’d find another ride home. I left with a feeling of just being happy that it was done. She’d texted me following up several times over the next few weeks, asking if I’d rethought anything, to which I gave a flat “no.”
I definitely won’t defend my judgment that evening, and would have almost certainly broke the news to her long before anything got going if I had a chance to redo things, but man, even in retrospect, her ass felt _fantastic_.
Source: reddit.com/r/gonewildstories/comments/f3mdsu/my_anal_breakup_experience_mf
Nice tecollection! Well written, too!