This was in one of my previous long-term relationships in my early 20s. Our usual sex life would be relative vanilla, she occasionally would give oral, ask me to fuck her a bit harder and I maged to introduce some toys, which however got very little use. Otherwise sex in missionary, doggy and cowgirl positions was about the extend of the usual routine.

After a while in the relationship, I discovered that my girlfriend would get more adventurous when we would be in situations, where it would be important to be quiet or otherwise be caught or noticed in the sexual act. These situations would be when sleeping over at friends house, where we would sleep on the mattress in the living room or in the guest room next to her parents with thin walls. On one of these occasions I noticed that the would do or ask for things that were not part of our usual routine, most prominently changing it up from the rather tame usual blowjobs to full sloppy deep throats.

While I always had a big fascination for anal sex and we had talked about it, we never got around to doing it. Until on a particular Christmas: We already had gone to bed, her parents sleeping in the room next to us and I already had written off sex for the night. While we were slowly getting more intimate, she suddenly whispered into my ear that she wanted me to fuck her ass, right then and there. Her eyes were filled with lust and there was no foubt about what she wanted.

While in disbelief I of course immediately agreed. She had brought the lube we had at home, which I bought on an earlier occasion for getting into anal play, but which we never had used. After some more foreplay and applying plenty of lube I ended up slowing penetrating her rear entrance in missionary position. It was an amazing experience and I had to hold back not to cum in the instance when pushing past the gentle initial resistance and sliding into her ass. We went slow and it was one the most intense sex sessions of our relationship. We both ended up cumming, me from the arousal of having my first anal sex, she from having anal sex only a few meters away from her parents bedroom.

While this was the most intense occasion, this subconscious kink of her helped to expand our sexual horizon a few time more, but the spiecier sex acts would only happen in similar settings.