My boyfriend and I have always been open-minded. We aren’t each other’s first sexual partners (far from it in fact), but we have achieved a lot of firsts together – first public sex, first group sex, first extensive bondage, etc. I could potentially be convinced to write up these stories another time. Who knows? We’ll see. But, without a doubt, the biggest, sexiest first for us was the first time I played with his ass.
For some background on us, we were in our mid-twenties and had been together about six months when this finally happened. Pegging and anal play had been a joke between us for so long that I didn’t think it would ever actually happen. We even joked about it the first time we had sex; we had talked about Broad City earlier in the evening, and when we changed positions I joked that I was going to peg him like in one episode. From then on it was almost a meme. We’d be lounging around on a weekend morning and he’d ask what I wanted to do that day and I’d say “oh wasn’t I supposed to peg you today?” or “oh my gosh I totally forgot that I have an appointment to peg you raw.” I never actually expected it to go anywhere.