So..

I’ve (22M) been fwb with this girl (23F) for a few weeks and we’ve had a lot of fun. She’s very open minded and I’ve always been kinky. I mentioned how I wanted my anal cherry popped by a girl in a strap on, so.. she was down lol.

We started with a dick that’s my size but more thick, (8 and my cocks thick, but this was more thick), she started with fingers and lube, and feeling those fingers in my ass were life changing… I loved being finger fucked!!! Especially when she was getting into it! Then we tried the dildo! We put the head in with plenty of lube but we couldn’t go farther.. I felt my ass was going to start bleeding if we went more and it wasn’t happening.. so we went back to fingers and I ate her out after. (I ate her to 6 orgasms throughout the night for being willing to try!)

However! We got a smaller 6 inch dildo that’s not as thick and we started the next time! She started by putting it in slow, but it accidentally went all the way in fast, it hurt but honestly I’m glad cause it helped me get used to having something in my ass 😅 after holding it in to get used to it, she started fucking me, first with the strap on then she used her hand so she could go faster!!! It felt so good in my ass! I may have went back for a second ass fucking a few days later 😅 we tried using the bigger dildo again, but it didn’t work.. however it was still too thick… I feel I could get all 8 inches in me but it was too thick and was gonna tear my ass up. We are talking about getting a dildo that’s thicker then the one we have but not as thick, next 😅