Content warning: gay stuff
Because this is about role-play, I'm not sure if this should go in the fantasy section, or in the fapping material section, but since I did this IRL I decided to post it here.
So, I'm a 29 year old bi sissy, and I've have had fantasies about my high-school bully fucking my mom for a while. However, I haven't seen him since my graduation, and I don't live in the same state as my mother, which makes arranging something with a friend logistically impossible.
A couple weeks ago I found an opportunity to kinda fulfill this kink; I met male escort who looks a lot like my old bully, and I decided to try some role-playing. We agreed that I would shave, cross-dress, use my mom's real name, and call him by my former bully's name, and that he would role-play as my bully, make degrading remarks about "her son and her husband" (using the real names of my dad and I) and even refer to my ass as her pussy.
In our encounter, I pretended to be asleep in my room, and he came in naked without saying a word. Then he spooned me, rubbing his cock against my ass, while he started grabbing my tits. I pretend to woke up and be in shock as I turned around and saw him. We began what's essentially rape role-play, but with a twist. As he kept fucking me, my acting changed from struggling to giving in. I let myself moan from pleasure, and he started saying things like, "so, you enjoy being fucked by a real man, bitch?" to which I answered in the sluttiest ways I could think of. Then he stopped, pulled out and made me beg for his cock, to beg for him to bread me. Finally, after he came inside me and we just lied down for a bit, he teased me about how from now on I was his personal cum deposit, that I would bear his child and leave my looser husband and son.
What do you guys think? Have you ever tried something like this? Would you be willing to do so?
EDIT: Note, at no point of our encounter did he touched my wiener.
