My boyfriend/ex-husband has always dressed as a woman for Halloween, but this year he came out that he is transgender and I'm fine with that. On Friday I thought I was going on my email and discovered it was his and came across some email to this woman that he had a one night stand with. He was telling her about how he wanted to have sex with her dressed as a woman. Yes I confronted him about this because to my knowledge I have been the only woman he has had sex with in the past 9 mouths. He said He wouldn't look if I could fulfilled his fantasies. He said we can talk more and that if I'm up to fulfilling them it would mean a great deal to him. I just dont know where to go with this, i love him with all my heart and I want to support him, but to have sex with him dressed as a woman or while he is wearing panty hose, I just don know how to feel. I have been crying on and off all day because I have know one I can share this with that will understand.  can anyone give me some advice on this and what I should do?

Firstly, welcome to Susan's. I'm glad you've found us. A part that really sticks out to me is this part:

Quote from: scaredandconfussed39 on December 01, 2013, 05:20:20 PM
He said He wouldn't look if I could fulfilled his fantasies.

To me, no matter what they identify as, that is completely inappropriate and unfair. It is unfair for them to put you in that position. If they are willing to cheat on you if you don't fulfil their fantasies then they are not worth having as a partner. It is a lot for an individual to take in and it is completely normal for you to feel the way you do. I hope you manage to speak to them and find an agreement that you are both happy with. All the best.

Big hug! You came to the right place, and the important thing is to remember that the person will always be the same person.  Obviously, you two have issues to be resolved. You can gain a lot of insight on this site, please look around.  Hugs, Devlyn

There are some links here that may provide some of that insight, they are aimed at the transgender person, but may help you understand what's going on: https://www.susans.org/wiki/Category:Family_and_friends

Hiya.

Unfaithfulness is not excusable on grounds of being trans. Considering how open and supportive you seem to be, he does not come across as being very grateful.

I would say, like any sex act, if you have a significant aversion to it then don't do it. It would not be right to pressure you into doing it. If it means that you are no longer sexually compatible then it is unfortunate, but ultimately, it is so. Either way though, I would not be able to excuse the unfaithfulness.

Good luck whatever you decide

Akira x

Hmmmm  Let me get this right.... He had an affair, Then afterwards he wanted to have sex again with her, this time as a woman. YET somehow this is all your fault because NEITHER you nor this other woman had sex with him as a woman?

Me thinks the only T-Card he can play here is testosterone, not transgender

My heart goes out to you. I can kind of relate to your situation. My husband had asked me once to have sex with him dressed as a woman...that it would mean a lot to him and all that. So after some Jack Daniels, I did...even though I didn't really want to. I didn't enjoy it, it was strange and bizarre and I felt odd afterwards. I was afraid that he would turn to someone else for that kind of sex. Looking back, I wish I was more honest.

If he is dropping hints of ultimatums... this is NOT fair to you. I hope you can talk it out. Mostly, I hope YOU feel better soon.