“I can’t believe I’ve never done this” [MF] Anal

My buddy invited me to a pool hall with a clubby vibe downtown, a few years after college. Lots of pool tables, foozeball, and other games, in a black light setting with a lot of music and a bar. It was a fun scene. I don’t know if I had realized when he invited me, but it was the birthday party of a friend of his. This friend had gone to school with us but I had never met her.

His friend was an Asian woman named Jessica. Maybe 5’4” or 5’5” with B cup tits and a cute little butt. She could’ve stood to lose ~5 lbs, but can’t we all? She wouldn’t drop any jaws, but she looked nice. She was also really friendly and bubbly. We all had a good time, playing pool, drinking, occasionally breaking to dance. The kind of chill night you look forward to.

I’m not sure how it happened, but Jessica and I started getting closer and flirting more and more. It wasn’t my goal to hook up with her, but I started to think she was interested. Eventually, I mentioned I needed to get some air was going to go outside for a couple minutes and she was interested in coming with me. We got outside and started to do a lap of the block. She was cutely giggling and laughing at everything I said. Eventually, as we were passing a dimly lit doorway, I spun her in and kissed her. She was clearly into it and we had a couple more quick makeout sessions before we got back to the bar. The rest of the evening, we were just biding our time.

At the end of the night, folks drifted away, and when Jessica went to leave, it was clear I was welcome to come. We headed back to her apartment and picked up right where we left off. Casual, carefree, though somewhat frantic making out.

I got her shirt and bra off and started to really enjoy playing with her boobs. Nothing too big, but perky and pointy. We were in our mid 20’s at the time and she was proud that her tits were still nice and perky. (She later told me that she wouldn’t do a threesome until she got old and saggy, and needed to makeup for it with other things.) Eventually I worked my way down to her cute little pussy. It was wet and slippery and took my fingers quickly. She clearly had been waiting for this and was into it.

Now, if you’ve read my other story, you know I’m a fan of butt play. So, as I was fingering her I’d do the “graze her ass” move and gauge reaction. It’s sort of fun to do – you slowly increase the pressure and frequency as long as you’re still getting positive reactions, until it’s clear it’s deliberate and not incidental. (Not sure I’d take that approach today, as consent has thankfully shifted to a more communicative paradigm.) It was clear, though, that she liked a finger in her ass. Soon I pounding both her holes with my hand, with my thumb up on her clit. She loved it and clearly had some experience with getting her ass fingered. She thrust her hips up to take my fingers and was desperate for more.

At this point, we discovered we had an issue. She was not on birth control and neither of us had a condom. I didn’t want to knock her up any more than she wanted a kid. We were a bit disappointed we couldn’t fuck, so we decided we’d 69.

We were both loved the 69 though! She was hungrily shoving my cock down her throat and I was enjoying being smothered by her cute wet cunt. At one point I had an idea that would get us around the condom issue. As I was eating her, I started fingering her ass again, and when she reacted in pleasure, I said, “I like what you like.” Forgive me, reader, that I was bashful and not as communicative as I would be now. I was trying to get across the idea that she liked when I played with her ass, and I liked playing with her ass. My statement only confused her though. So, as she was throating me, she worked her fingers over to my ass and started to apply pressure, still unsure what I meant. If this happened today I’d have rolled with it and frankly probably just encouraged her to use her tongue (and I have little doubt she would have). However, even though the pressure felt nice, I became self conscious and stopped her.

Instead, I explained that what I meant was that I liked playing with her ass, and she clearly liked it, so maybe we should try anal to find a way to fuck. She’d never done it before but agreed it was promising given how much she loved getting her ass fingered. We both considered our mutual friend to be a really good friend, so we figured if he trusted each of us, we could trust each other to be clean (still too risky, but we were pretty drunk). We didn’t have lube, but as this point everything was soaked.

From my experience with Jen in my other story, I had an idea of how to best do this. I got her on her hands and knees and slowly pushed my dick against her puckered asshole. I’d apply a little bit of pressure and then pause, letting her adjust. Then a bit more, and a pause. Little by little, I worked my cock into her ass – the first time she’d ever taken a dick in her ass! Now here’s where it got especially exciting. You would think that the first time she let a guy fuck her ass, she’d need/want it to be gentle. Gentle in and out, maybe picking up the pace a little bit. NOPE. Within a few minutes of feeling the head of a dick push past her sphincter for the first time, she’s grunting, groaning, and moaning for me to pound her tight little ass. She was a natural. She loved it and was truly screaming at the top of her lungs. I was worried she’d wake up her roommates, but she loved being filled and pounded so much that she didn’t care at all. At one point she even yelled out, “I can’t believe I’ve never done this before!”

I can’t effectively convey how intoxicating it was to watch my dick pound her ass while I held her by the hips with both hands. To feel her tight ass grip my dick with each thrust. To know that I was the first guy to corrupt her this way, to make her my little anal whore. And to know that not only did she like it, but she LOVED it. You can imagine that I didn’t have any trouble filling her ass with cum, and you can imagine how she loved feeling my dick pulse when I filled her up.

What followed that night was a casual FWB arrangement that lasted for maybe 6 months. It was great. I’d come by and we’d go out to dinner. Have a couple drinks and hang out. We were pretty compatible as friends. I made sure not to catch feelings. It was a relatively low stress arrangement. We were better prepared in the future, so I got to fuck her pussy plenty. But every time I came by, there was an expectation that she was going to get her ass pounded. I have an image burned into my brain from one of those nights of watching her in reverse cowgirl, reaching around and pushing my cock up her ass as she lowered herself down into my lap, and then watching her bounce up and down as she used my dick as a toy to fuck her own ass.

All good things come to an end. She met another guy and we tapered off. That was fine though! Had plenty of great times until that happened.

I do take pleasure in knowing that she’s now an anal convert. When she sleeps with other guys, and they marvel at the fact that she’s into a guy putting his dick in her ass, I was the one who introduced her to it.

Source: reddit.com/r/gonewildstories/comments/prw25u/i_cant_believe_ive_never_done_this_mf_anal