Question:

Wondering if a lady I'm dating already knows if I'm a crossdresser.?

by Guest33469  |  earlier

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I've been seeing this one lady for a while. We hit it off pretty well the first time we met. We hung out a couple weeks later, enjoyed each other's company, and have been dating ever since. I am smitten with her. She's very pretty, educated, amazing moral base, and has things going for her. Of course an underlying fear of mine is if things get more serious between us, I will have to tell her about me being a crossdresser. I say fear because she very much a Christian, which makes me unsure of how she'll react if we get serious to the point where I have to tell her (I typically don't tell girls that I'm merely dating). Despite her beliefs, she is very accepting of other people, but I know from experience that doesn't equate to being accepting of that in a romantic interest. I'm Christian too, but obviously no hyprocrite of the good old Deuteronomy 22:5 passage, or a lot of other restrictive OT passages for that matter.

I'm very suspicious that she already knows, and honestly wouldn't be surprised if she does. I say that first off because of my drunken birthday incident where I accidentally outed myself, which could have very easily gotten back to her given the small community I'm currently living in. I know that she has asked about me to a few other people, so it is a good possibility. Second, we had some pictures of us taken. I forgot that I had some pictures of me crossdressed in my camera still, but she started scrolling through my camera after the pics were taken and stumbled upon them. I was able to snatch up my camera before she got a good look. She wanted to see the pictures, and I told her no because they were pictures I didn't think were appropriate for her to see. Not a lie, but not revealing what I considered unnecessary information. She promised me she wouldn't be judgmental, and emphasized the judgmental part, but I didn't waver. She also did her nails later on and made a casual joke that she could do mine too. I played that one off well as I told her she could do my nails if she wanted, knowing that being hostile to the idea can be a giveaway. She has also made other comments that could imply she already knows, like when she borrowed some shorts and a shirt from me when we went on a road trip and thanked me for letting me wear my guy clothing and how I didn't feel uncomfortable with it. She also asked me if I thought one of my buddies was attractive to where I would hook up with him. Of course that answer is no. There have also been subtle questions she asked as a way of probing my sexual orientation.

So there is a good possibility she already knows, or I'm just being paranoid about the issue. If I was asked point blank, I wouldn't lie, but she hasn't asked me that, at least not yet. Whatever the case might be, she still wants to keep seeing me. I just don't know what to think of the issue. Does she know for certain? If she knows, what does she think about it? If things get more serious between us and I have to tell her, how will she react? I don't want to lose her over that potential issue, but what's a guy in my place to do?

All input is welcome, especially from other crossdressers or women who've dated a crossdresser. FYI, I like a lot of the clothes but I don't go for a full female look.

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4 ANSWERS


  1. Wow, very entertaining to read, I'd say that she probably doesn't "know" but may wonder quietly to herself.  If she really likes you like you like her I would just tell her. Make sure you do it at the right time. Don't go spilling it over a nice dinner or something.  You'll know when the time is right.

    This situation reminds me of a Oprah episode about transgendered people who transitioned after marraige and they have spouses and families.  It was really facinating. :D

    How old are you by the way?


  2. Of course you need to tell her, for no other reason than because it's really bothering you.  You won't feel comfortable until you get it off your chest.  On another note, when you do tell her, you need to be prepared for the fact that she'll be weirded out by it.  It doesn't mean she doesn't like you anymore, she just won't know what to think about it right away.  

    And I have to be brutally honest with you here: if a guy I was dating revealed something like that to me, it would be a total turn off.  That's not a matter of "tolerance" or "acceptance," it has to do with what you find sexually appealing.  You wouldn't say that a g*y guy is intolerant of women, just b/c he isn't attracted to them would you?  The same goes here: it may be too much of a turn off.  But who knows?  It also depends on how serious she is about you too.  

  3. do you think she reads minds?  TELL HER.

  4. tell her the truth, chances are she already has an idea. if she cares for you the possibilities are endless. besides you lost a huge oppurtunity when she offered to do your nails. my husband is a crossdresser, and it all started at a mary kay party at our place. my friends and i convinced him to get a makeover and now he dresses for me whenevr i ask him, he has spent a whole month on vacation all dolled up. so go for it and tell her the truth

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