[M]y [F]irst anal

This happened almost ten years ago. I wanted to capture why I still think about it even now, but I’m not a writer and English is my second language, so I’m sorry its not a pretty writing style.

After school, me (23) and my girlfriend (20) were living in a house with a friend of mine. He had the first floor, we lived upstairs. The only inconvenience was that the downstairs kitchen was not finished and we didn’t have the motivation to do anything about it. That meant that we had to share the kitchenette in our living room with him. We were used to this, so the sex was reserved for the bedroom, as he could come upstairs anytime.

My girlfriend was a curvy girl with short dark hair, she was shorter then me and had gorgeous big boobs. We were both horny all the time and we really enjoyed each other. Before her, I was always shy and insecure, but it was changing a lot while I was with her. She wasn’t afraid to tell me what she liked and always let me know when I did something she liked. I started doing the same and we became very good at enjoying sex and making the other enjoy it.

One day we were spooning on the couch while watching TV in the living room and we heard my friend coming up. We just threw a blanket over us, because I wore only my boxers and she was only in a shirt and panties. This was completely normal and it wasn’t the first time he went cooking while we watched TV under blanket. He comes into the room, we chat a bit about the day and random stuff, he starts cooking, we watch TV.

Suddenly I feel my girlfriend slowly moving her hand back under the blanket and getting into my boxers. I didn’t really like the thought of my friend catching us have sex so I didn’t do anything, but still silently enjoyed the touches. After a few minutes, our friend had to go to use the toilet and when he disappeared in the bathroom, my girlfriend without a word took her panties off, threw them under the couch, got back under the blanket and pretended like nothing happened.

By this time, the touching and her stripping her panties started to get me pretty hard and I was sure what she wants. The deal was closed when she pushed her ass against my dick and started to tease me. During all this time, we haven’t said a word to each other, partly because we were woried he could hear us (even though it was impossible through the bathroom door) and partly because we were completely captivated by what was happening.

When he returned, it seemed that the only change is that we were suddenly much more quiet. I asked him a few questions about unimportant stuff, to cover up the quiet while my girlfriend was slowly, but very firmly grinding my dick with her bare ass. My brain was already somewhere else. I began slowly moving my upper body a bit back to have a better angle if she really wanted to go all the way and fuck. To be honest, at this point I stopped caring about my friend and even though we were still trying to be super stealthy, I also just wanted to fuck her right that moment.

While my friend continued with preparation of his chicken pasta (he always prepared multiple meals at once and it took a long time), she changed her movement, got her hand back behind her and slowly started to guide my penis inside her. As we were moving very slowly and couldn’t make big moves, it wasn’t as easy as it usually is. After some time, my friend suddenly asked us something about the program in TV, so we had to freeze for a bit, with the tip of my dick between her cheeks and chat about the fucking weather or whatever. When he finally got back to cooking, to my surprise, instead of moving again, she just pushed against me and I felt my dick very slowly started getting inside her ass. We never did anal before and it wasn’t some great fantasy of mine, but when I realized what’s happening my already high pulse went through the roof. My dick is slightly below average size, which was now an advantage and it was completely covered with precum from the action before, but to be sure that I don’t hurt her, I didn’t push at all and just waited as she slowly pressured my dick inside her. I felt the tightness and how she was compressing and relaxing the muscles, every move. I was totally out of my mind and just trying neither to cum immediately nor to start wildly fucking her. When I was all the way in, she turned her head slightly to me, moaned and whispered: “You know where you are?”. It’s up to this day one of the hottest sentences anyone ever told me. We managed to be almost still and silent, with my dick buried in her ass for what felt like an unbelievably long time. I also managed to squeeze her boobs a little and she kind of let out a loud moan, which she tried to cover as a yawn. I had no idea if it worked but my friend continued with his cooking. I could feel that I can move my penis inside her quite easy now.

It’s a luck that my friend was leaving because in a few seconds, I would just fucked her in front of him. The moment he shut the door, I threw the blanket on the floor, turned her on her belly and holding her hair, only after two or three big thrusts I came in her ass for the first time. She was biting the pillow the whole time, and it felt like she almost came too. After I came back to my senses, with my dick still inside, I reached under her between her legs to also make her cum. She was dripping wet and even her thighs were wet after the long time and movement. She was so close, that it took really only a minute and my hand before she also came. We lied down for a minute to catch a breath and went to get a shower. No hygienic problems happened. Then we moved to bedroom and spent the rest of the day having more conventional sex, sleeping and talking about what happened.

Since that day, she really enjoyed anal from time to time and so did I.

Sadly, we broke up after a year and almost made each other crazy before that, but the sex was great and I have many memories of her.

Source: reddit.com/r/gonewildstories/comments/pgr5k2/my_first_anal