A
male
age
41-50,
*laire1985
writes:I'm engaged to a wonderful girl. I've always considered myself a female in my heart. I have been crossdressing secretly in the past but I can't anymore. I really want to go out and be feminine once in a while. I explained my fiancee my situation. I was very clear I'm not attracted to males but in my heart i truly wish i was born a woman. I think i would be a lesbian. LolShe understood me and accepted me with a couple of conditions. To remain faithful (which I am. I love her) and never let her see me dressed up. How to address her the situation that i want to go out and have fun as a female without hurting her feelings? I could do it secretly. But she will find out eventually and i don't want to break her trust.
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engaged, fiance, lesbian Reply to this Question
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male
reader, anonymous, writes (28 October 2017): Even if you're a woman who is a lesbian stuck in a man's body,what she wants is a man. Not somebody who looks like a man. She is a woman who thinks of herself as a woman and is straight. Make of that what you should but to me that doesn't add up.
A
male
reader, Claire1985 +, writes (28 October 2017):
Claire1985 is verified as being by the original poster of the question@honeypie Thank you, You're right. She deserves to know at least what is going on in my mind.
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A
male
reader, Claire1985 +, writes (28 October 2017):
Claire1985 is verified as being by the original poster of the question@Aunthonesty: Thank you, I'm considering therapies.
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A
male
reader, Claire1985 +, writes (28 October 2017):
Claire1985 is verified as being by the original poster of the questionDear jls022 your comments are very reasonable. Thank you so much for your insight. Despite the fact that deep in my heart and mind I truly feel as a female I'm very aware was born as a male and sadly there's nothing i can do to change it. I don't intend to alter my body with surgeries or hormones. Your comment is spot on about the woman I love is in love with a man. I respect her and her feelings. That's why I 've never consider to let her see me dressed up. Certain things are too private and is better for her to not to see me as a TG.
She is Ok about the crossdressing thing. I'm not sure if she would be ok about me going out in public.
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A
male
reader, TylerSage  +, writes (28 October 2017):
 When you two got together you clearly explained the situation to her. I don't believe for a second she understands because if she really did she would allow you to dress up as you please. I'm sure you can see how big of a problem this will be later down the line. Have another talk with her but you must realise she may not want you to do it. If that's the case you need to make a decision about who or what you can live without for the rest of your life.
Don't suppress the woman you are.
All the best.
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A
female
reader, holeymoley  +, writes (28 October 2017):
 If I understand your post correct, her conditions are NOT to let her see you dressed as a woman. I think you are on a winner with this woman mate. She seems to have accepted this is a part of who you are and want to express, that takes great love. It also takes great love to respect her wishes by not doing so. Talk to her a bit more, if you cant maybe through counselling and try to establish some boundaries that can work for both of you. You seem to have a fairly open and honest relationship so personally I would not want to be doing things behind her back and have that go to rack and ruin. Have you investigated transvestite places of entertainment in your area by chance? Maybe that could be a good place to start. Now please let me be clear, I don't mention this because I am of the opinion that you should hide who you are in anyway, more because if you are wanting to go out and about what might be the consequences for your fiancee? Hopefully none but lets face- people can be judgmental arseholes. Ever thought about taking her to a drag queen show, personally I love them, good fun, great people and atmosphere and I'm straight. Good luck with it all
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A
male
reader, Billy Bathgate +, writes (27 October 2017):
I don’t understand. You told your fiancée, she said okay but no cheating and she doesn’t want to see you. What more do you want?
Go out when she is not around and don’t go to places you know she goes. You’ll have to cultivate friends outside your current circle but that shouldn’t be hard. Every medium sized city has at least one cross dressing club. Look them up. They can help you come out of your shell
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A
female
reader, aunt honesty  +, writes (27 October 2017):
 I don't think your fiance wants to see your dressed as a woman and that is what might make this situation very difficult for you both.
Taking your partner out off the equation for a moment you need to work on your life and what and who you want to be. You say you feel like a woman inside so I think you need to dig in to that part off you. If that is who you feel like then what is stopping you getting a sex change and being who you feel you are? I think deep down you think off yourself as a lesbian but I also think deep down you don't want to admit it because you have falling in love with a woman and she is straight and loves you as a man. You have a lot off issues here and you really need to be true to yourself. At the moment you cross dress, now you want to go out as a woman, how long until you want to be a woman? I think you and your fiance would benefit from going to see a therapist. However don't try and be someone that you are not because you are afraid off loosing her, be true to you and who you are, good luck.
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A
female
reader, jls022  +, writes (27 October 2017):
All you can do is ask her, but you’ll need to do so knowing that you must respect her wishes if she says no.
I know some people might argue that you have the right to express yourself in any way you see fit, which is right to an extent, but not if it breaks the trust of your partner.
OP she’s already been very accepting of your confession so far. Much more than I think I could have been. Personally I’d have no issue with the cross-dressing, but your confession that you feel like a woman inside would worry me a lot because I’d be scared you might want to make a permanent transition one day. And as a straight woman, that’s not something I could accept in a partner.
And to be brutally honest, I think your partner might feel the same way. The fact that she doesn’t want to see you as a woman tells me that while she’s willing to accept it, she doesn’t want to actually have to SEE you as anything other than the man she fell for. For that reason, I’d be very surprised if she would be comfortable with anyone else seeing you like that either.
And I really can’t blame her for that. You might feel like a lesbian, but she doesn’t. She is a straight woman, who signed up for a heterosexual relationship with a straight man. That was the deal from the get go. You’ve now changed it and she told you her conditions around accepting that, yet now you’re trying to push the boundaries a bit further again. Which makes me think you haven’t truly accepted the extent of your feelings on this matter.
So, I think instead of focusing on your desire to dress up in public now and again, you need to have a long think about how you envisage your future. Will you be happy living your life as a (at least on the outside) heterosexual man forever? Or will that feel too much like living a lie to you? Do you think you might want to become a woman for real one day? Either via hormones, surgery, both, or even just in name only? Because all of those things SIGNIFICANTLY alter the deal your girlfriend signed up for, and you owe it to her to try to resolve that and be honest with her about it rather than drip feeding her the information and continually asking her to accept a new type of relationship.
That’s not fair to her or you. Sure it might be difficult, and it may cost you your relationship, but if you love her you need to do it to give her the chance to make an informed decision. And you need to do it now, before you make a proper commitment to her.
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A
female
reader, Honeypie +, writes (27 October 2017):
 Just ask her how she would feel about it and go from there.
I think if she can ACCEPT that you crossdress and STILL want to marry you, it might not be as big of a deal as YOU think.
And honestly? I think hiding your dressing up from her is a bad move. LET her see YOU - ALL of you. She seems pretty openminded to me.
One thing I would suggest IF she is OK with this don't go out ALONE or without her dressed as a woman. Because that is hiding it.
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