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My boyfriend is a cross dresser and he's decided he may want to become a woman!

Tagged as: Big Questions, Dating, Troubled relationships<< Previous question   Next question >>
Question - (2 August 2007) 3 Answers - (Newest, 3 August 2007)
A female United Kingdom age 41-50, anonymous writes:

I'm a lady with 3 kids, one is disabled. My partner lives in Guernsey and I'm from Bath and he's a cross dresser and I knew that we have been together for nearly 2 years and recently he's decided he may want to become a woman fully but he's not sure but he's confused. I feel as if I can't get upset as it bothers him but I'm hurting as don't know wots gonna happen. He just pushes me way, I'm trying to move forward for us but he wont until he knows but he wants me to except him. How can I if he pushes me away all the time? please help

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A male reader, anonymous, writes (3 August 2007):

I'm not an expert in psychology, but having been a cross dresser since age 9, who's been in mostly (though not all) heterosexual relationships, I may be able to shed some light.

Your boyfriend's penchant to be female, or certainly more feminine, will never go away. It may go through some dormant periods which may lead you to believe he's over it, but it will always come back. A guy who’s in denial about this desire is like someone trying to run from something that he knows full well always runs better and faster than he does. Because of this, your relationship can never be a typical man-woman type. If you try to make it that, you'll be forever frustrated.

You are much better off going the other direction and encouraging him at every turn to dress up and to be more feminine, even helping him shop and maybe even buying him gifts of women's clothing, makeup, etc. Treat him as you would a close girlfriend and begin to think of him in that way. Discourage sex and remind him that as a woman, the sex he knows now would no longer be possible, and that he needs to begin to adjust. And yes, I would even help him explore the surgical options. While this is going on, I would also tell him that you're getting quite used to the idea of his being female, but because you are physically attracted to men, that you need to begin dating someone. And don't just talk about dating someone. Do it! And tell him about the dates afterward, whether they’re casual or more. All this should occur while you’re constantly complimenting him on his female traits and looks, and gradually phasing out sex with him save for mutual masturbation.

This may sound insane at first, but think about it. Your going about this way will either cause him to realize his manhood, if indeed there's enough of it to make a heterosexual relationship possible. If he really wants you as his woman, it’ll become very clear. On the other hand, if your actions cause him to make the decision to become a woman, that will seem devastating, but it will have been inevitable. And if it would have happened later, it would have been far more devastating in its taking years away from you both. If it should go that way, there would certainly be heartbreak and who knows what else, but the bright side is this newly formed woman will probably be the closest, most trusted and trusting and beautiful friend that you will ever know in your life. The old relationship will of course be gone, but a new and wonderful one will have taken its place.

Briget

Chicago USA

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A male reader, anonymous, writes (2 August 2007):

Crossdresser thats wants to be transgendered. You've got kids lady and, I expect, a reputation also. Keep asking him if he wants to go through with it. If he eventually decides he no longer wants his penis you have two choices: Become lesbian or find another man (maybe one who isn't confused?)

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A female reader, aphexinfinite United Kingdom +, writes (2 August 2007):

aphexinfinite agony aunthmm well a friend of mine wanted to become a women then me and him met up finally after 2 years of knowing one and another and he realised that he wanted to be a man, some men feel as though they want to be a women but at the end of the day their confusing reality with a dream or a fixation, i think youre man needs to see a doctor about this, some people think what they want is what they want but sometimes people say yes go and do it and they will but some need to hear no dont do that youre perfect the way you are or need something or someone to realise its not what they want or he maybe wants it not sure what else to say hope this helps a little xx A

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