Shame on Me!

For a really long time I was completely against cross dressing and it’s use as a tool of domination. I’ve always been a firm believer in female supremacy, even before I knew that I was a Domme or anything about BDSM. Because of this deep rooted inclination towards thoughts of female superiority I found it highly disrespectful for a man to dress as a woman; I must interject that I’ve always been fine with those who legitimately feel as though they are transgendered. My particular discomfort has been in men that enjoyed dressing like women for arousal and humiliation. The issue being that in the end it was an objectification of the feminine. Over the past few months I have relaxed my point of view and it has opened a whole new world of kink that I never imagined to be so enjoyable.

Some months ago, I want to say at least six or eight I received the first email from him… I read the person’s profile and saw the photo and immediately passed judgment, “he’s a cross dresser, I have no interest…” and I sent a reply stating such. Politely he responded that he was not only interested in that but also had many corresponding interests as me. I ignorantly poo pooed the email and went about my life. Then approximately two months ago the same individual emailed me again and expressed interest, this time asking me to please give him a chance, that he thought we would click well and our interests lined up on many points. I reluctantly said that I would give him a chance. We spoke on the phone and then very quickly decided to meet in person for dinner. He was right, we did have a lot in common and I felt like a complete ass! Think of all the people I had turned down over the years because of this, think of all the missed opportunities…

So, over the past two months now we have continued to see one another and to have play sessions. The more I grew to know him the more curious I became about the use of cross dressing. He and I talked about it at length and the more we talked the more aroused I became at the possibilities of turning him into “my gurl” … “my slutty gurl.” The ideas of playing dress up with her, reversing roles and fucking her like a slutty gurl, and even having men come and fuck her completely gave me an entire new sense of domination and control. Then he showed me photos of him as a her and it sealed the deal, she was passable, she looked like a woman and I loved it!

This past weekend was our first endeavor into this sort of play. The first step for me was to find men, men that wanted to have sex with a t-girl or cross dresser. I searched high and low and found lots of guys willing to come over and play with us. She and I went out and found her sexy things to wear, then got her all dressed as a woman and I even did her make-up. A few minutes before 11pm the first man arrived and three more trickled in shortly after…it was on! I instructed her to  suck cocks and be fucked and have her face doused in cum… I even got fucked during all the action too, which was amazing!! The entire experience was such a turn on, I never would have imagined it would have been so great. But it wasn’t over, when all the men were gone and it was him and I again we enjoyed each other’s company, came down from the whole experience, and had great sex. I felt almost like he had something to prove, I felt as it he was showing me “you see I am a man too”, and that was extraordinarily hot. I kept saying to him things like, “Are you trying to fuck me better than that other guy tonight” and “You like showing me you can be a real man,” which drove him to perform better and strive to please me more. Finally after I came I allowed him to cum from me jerking him off, because he had been such a good boy… or should I say gurl all night!

I’m so excited about the wonderful new kink I’ve found and the sub I have to share it with. I have no clue where things are headed with him/her, all I know is I’m enjoying it and I can’t wait to experience more. I have no clue how all of this fits into my thoughts about female supremacy but I think it’s time I just do what feels right, what makes me happy. I’m a bit sad that it took me so long to open my eyes to the possibilities of this kink, I guess I will just have to try extra hard to make up for lost time!