I really love anal sex and I’ve given it and received it. (I’m a bisexual male). One past anal sex partner of mine we’ll call “Rosie.” Rosie was a short, white woman who wore think, but stylish, glasses and had brown, straight hair. Her body was average sized but she had a really thick ass that I noticed when I first met her through a mutual friend. What I learned being with Rosie from the time we spent together was that she was a very openminded woman, sexually speaking. Rosie once told me she wanted to anally penetrate a man, and I willingly volunteered to be her victim while we were hooking up. Rosie was delighted and pulled out a large, black and red dildo and a bottle of lube.
I got up on Rosie’s bed, undressed and faced her nightstand and a mirror that was hanging behind it so I had a full view of my face and Rosie as she crouched down on her knees behind me, putting lube onto the dildo as well as rubbing some on my butthole, which took me by surprise. Rosie applied a generous amount of lube on me and the dildo and then said “Are you ready?” I took a deep breath and said “Yes,” and the next noise I heard was the dildo turning on, vibrating as Rosie held it in her hand. The dildo was black and was large. I remember thinking to myself “I hope my butthole can handle it.”
Rosie then put her free hand on my right butt cheek and spread it so that she could, as she told me “get a clear line of site to where I need to insert this thing,” which was the first time someone was going to do something of this magnitude to my backside. I then felt the vibrating dildo’s tip up against my butthole and then Rosie gently but firmly inserted the dildo up my butt. I yelped out but Rosie pushed deeper into me. I was bent over, vulnerable and now had a large dildo up my ass. Rosie kept in position behind me as she also gave me bottom a spank or two (or five) and seemed to be loving the fact that she was anally penetrating me. I loved it too to be honest. First time for everything!
Source: reddit.com/r/gonewildstories/comments/bj1uot/a_f_shoves_a_big_dildo_up_my_bisexual_ass
I’m hoping I can eventually have this kind of experience