Yikes! My Boyfriend is a Crossdresser

Posted: October 10, 2011 in boyfriend crossdresser
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“Honey, I’m a crossdresser” can be some of the most shocking and devastating words you’ll ever hear your hunk say. A thousand questions and concerns are now racing through your head. Is this normal? Is he a freak? What do I do? If you’re serious you may even begin worrying about how your parents will take this, and whether you’ll tell them.

This is a stressful time, and rest assured that he must love you deeply to share such an intimate secret with you. This articles provides some words of encouragement and advice to soothe the emotional wounds from hearing that your boyfriend is a crossdresser

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Comments
  1. Alannah says:

    Hi Vanessa, I’m wondering if you can help me out.

    I think I’m probably in the minority, based on reading thecomments in your “my husband is a crossdresser – now what” post, but the thing is – my partner is a crossdresser, and I like it.

    He’s the first person I’ve ever been with who blurs gender boundaries. He was totally honest and up-front about it; he told me about it when we decided we liked each other enough for a second date. We’ve been seeing each other for almost a year, and I’ve dressed him up several times. I buy clothes for him on occassion (not that he’s shy about buying them for himself), we paint each other’s nails, I’ve been teaching him how to put on eye makeup, etc. etc. He’s eating this up with a spoon, because he says his ex-wife hated and despised his feminine self, whereas I embrace her fully. I don’t see my partner as 2 people, or dual-sided, but rather a remarkably balanced person who can express his masculinity or her femininity equally and without shame.

    Now, I could probably go into a detailed self-psychoanalysis about why it is that I have so much fun with his crossdressing, and that would be fine – and I don’t particularly have any qualms about the fact that I find her enormously, incredibly sexy in a short skirt and tight little top (complete with bra and forms) – but what I’m wondering is, does it make me kind of weird that I’m pretty sure I’ll never be attracted to anybody who is unilaterally one-gendered ever again? Like I said, I seem to be in the minority – I LOVE that he’s a crossdresser. He’s a guy’s guy – loves tinkering with his vehicles, doing little maintenance stuff on the house, working out, etc. etc. – but he’ll do all of that with a silk cami and matching panties under his shop coveralls. And that gets me going in ways I’d never experienced before.

    But more than that, we can converse on a level I’ve also never experienced. I’m one of those women who is typically more comfortable in the company of men – I find that women (at a risk of being stereotypical) tend to engage in a great deal of competition that results in backbiting, gossip, etc. etc. and I just don’t have the patience for that type of drama. Men compete with each other too, but from this side of the fence it seems like a much more open and honest type of competition (insert diatribe about the anthropological and sociological implications of gender-specific competition, etc. etc.)

    Anyways, I’ve always found that men are easier for me to talk to in general – but I’ve never found myself really able to connect with a man the way that I can with my very few, but very close, women friends. And with my partner, I have both sides of the coin – the ease of straightforward, honest communication AND the deeper fundamental connection women usually only find with one another. My partner and I can move from a conversation about how our respective workdays went to our attitudes about child rearing (we both have kids) to a frank discussion about our feelings/emotions/insecurities/hopes for the future, to chatting about clothes, to planning our next date, and then back to work in a single telephone call.

    Well, I really didn’t mean for this to be a novel when I started; I guess what I’m looking for is any kind of information or resources you might have for somebody who, despite being relatively new to the whole CD/TG scene, really rather likes it.

    Thanks for listening. <3

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