Long story short, I'm bi guy that likes to crossdress for sexual pleasure. When I decided to share crossdressing with my (female) partner, I ended up single so sharing is not something I regularly do. When someone asks me about being bi I tell them I'm intimate with women and I occasional hook up with a guy (I only top and oral). When I'm dressed up I like to play with my ass and I've always wondered what it would be like to be pegged by a woman.

I recently met someone (female) who is coming out of a long-term relationship. She described herself to me as sexually repressed for a long time and now she was experiencing things she has always thought about. She doesn't know about my crossdressing but we've talked about how we both perceive sexual attraction as fluid, as opposed to being defined. I explained that I've always wanted to be with a woman while being locked in a chastity cage so I could experience intense intimacy without have the gratification getting hard and having an orgasm. She seemed really into it and she shyly asked me if I'd be open to letting her peg me. I told her i was a virgin back there so I would need an extended period of play to make it happen. She was shocked I was open it. The shock of me saying yes lasted for about a minute and in a playful, but serious tone, she asked me... so you're okay with me dominating you and taking total control? I was instantly erect when she said that to me. Based on her tone she already has something worked out in her head. She told me she has never pegged someone but she tried to talk her x into it many times.

I'm traveling for work for the next 10 days but we are supposed to talk more when I get back. Hopefully i will have a good story to share :)