When I was dating my first boyfriend David he was over at my house the night before thanksgiving. I had just turned 18 and we were seniors in high school, so we were at my parents’ house and had to be sneaky when trying to hook up. When you walked into my house there was a small bedroom right next to the front door that my mom would let us hang out in with the door open.

I was wearing jeans and at one point he pulled them down and got on top of me so that I was laying on my belly (prone bone) and he started fucking me. I’m being as quiet as I can be as he fucks me hard, when suddenly I feel a sharp pain as I nearly scream and completely lose my breath. I remember feeling like my ass was ripped in half and I realized he slipped in the wrong hole. He pulled out immediately and I curled into a little ball trying to catch my breath. I remember it feeling like my insides were on fire. I was also trying to stay quiet so we didn’t get caught but I felt like I was going to throw up. I wanted to cry but was also kinda in shock. He comforted me and apologized and said it was an accident (I believed him) and was really sweet to me. After a few minutes, I felt better but my ass was sore for a few days.

This experience and another failed attempt at anal with him a few months later scared me away from any and all butt stuff for years, until I met my now husband actually. I don’t really count it as losing my anal virginity and I still consider my husband to be the only man that has had my ass, but I’ll never forget the night it accidentally slipped in.