He is a wonderfully sweet man and finds me sexually attractive, but he likes to wear dresses.

I met this man before Thanksgiving. He is a man that likes doing guy things. He is a mechanice. He can build things. He loves guns, hunting, etc. He is also very sensitive. He gives wonderful massages, loves talking, shopping, etc. He is very active in his church and works with transgender people. He is very compassionate and helps anyone he can. We talk on the phone all the time. He will come out of his way to go to lunch with me. He even worked on my vehicle, wouldn't take payment for doing it, and then afterwards played catch with my sons. I could see myself with this man long term. The only problem -- he has a condition that is causing him to grow breasts and lowers his testosterone levels. Right now, he likes wearing dresses and heels when he is not around his family. He has been completely honest and open with me about this. In a few years, when the condition "worsens", he wants to become a woman full time. He's asked me if that would upset me. I honestly don't know what to respond to that.. I have never had to contemplate that in the past. I need some advice. He is such a wonderful person, and I know it's what's on the inside that counts. Should I overlook the fact that he will one day become a woman?I need some advice, please.

Updates:
Thank you for your responses so far. They are really helpful. And no, I'm not bi or lesbian. He is a very attractive man, but he's shown me some pictures of him in a dress. It doesn't freak me out, but it does concern me.

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Most Helpful Guy

  • You should not overlook the fact that he will become a woman. As a rule, don't overlook the long-term implications of your relationships.

    Your question seems to be: Do I want to sign up with this guy/girl long term? My answer seems to be: I dunno. I don't what you're built for, what you can handle.

    He seems like a really good guy, but one day he's going to be a really good girl. Will you be okay with that, long-term? Are you ready to ride this upheaval with him, and hang around for the aftermath?

    You need to have an open, forthright conversation with yourself. If it's too much for you, be okay with that. If you want to gamble on a happy future with this person, be okay with that.

    Then, either way, take a deep breath, and make the leap. Good luck.

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What Guys Said 1

  • When I first read the top of this post, I though, you're dating a tranny. There are very few women who are prepared to date tranvesites, but I was going to say, put up with it. It probably contributes to his senstivity, if he enjoys its, then its just some fun.

    BUT, you say he is transexual and wants the operation. So you would be dating a woman. I'm assuming your not bisexual or a lesbian, so "the rub" is do you want to date a woman? And the answers sounds like No.

    Should I overlook the fact that he will one day become a woman?

    I can't see how you can; its too large an issue to just over look it.

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What Girls Said 1

  • I honestly don't believe, but I could be wrong, that there is any condition that will suddenly change you from a man into a woman and make you grow breasts. He's obviously taking female hormone suppliments, and is probably in the transition process from a man into a woman. Doesn't mean that this man can't care for you, but he wants to be a woman, so ask yourself, are you a lesbian? can you be intimate with a woman? if yes, the go for it! if not then its pretty clear you will only ever be friends with this person, which is also fine too.

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