Should I date a (straight) guy who likes to cross dress?

We like guys to have feminine behavior . They should be sweet and understanding, etc... But what if he likes to cross dress? An advantage or disadvantage?
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Most Helpful Girls

  • I assume you mean cross-dressing in a sexual way, not an every day thing (i.e. he doesn't dress in women's clothing in public). If he did do it in public, there's a good chance he would be subject to a lot of ridicule and discrimination, and you would experience that by proxy. You would have to decide whether or not you're comfortable with that.

    But assuming it's "in the bedroom"/at home only.. well, how do you feel about it personally? I don't see anything wrong with it. It's my opinion that as long as the people involved are safe, sane, consenting adults, it doesn't matter what they decide to do.

    Personally, cross-dressing in itself is not a turn-on for me, but I could see it being a turn-on in specific situations. For example, I enjoy roleplaying and I think it would be hot if I was dominating him and subjected him to "forced" feminization (i.e. in the roleplay, I was forcing him to wear women's clothing, make-up, etc. and having him do things that are traditionally seen as a feminine role), or I would be up to trying some role-reversal. Also, I recognize that sometimes my partners have different fantasies and turn-ons than I do, and I'm willing to do those things on an occasional basis because I know my partner enjoys them (and hopefully he'd be willing to do things that I enjoy more than he does, as long as he isn't uncomfortable doing them).

    That said, if this was a regular thing (i.e. he wanted to do it all the time, or needed to do it in order to get off), I don't think I would date him, as it isn't something that I enjoy regularly.

    • He doesn't do it only for a sexual thrill. We went one time to a LGBT-club where he could crossdress in a safe place and he didn't looked like a transvestite. I think I would be turn off if he did look like a transvestite. He is just a part-time girl and I am okay with that since I consider myself as bi-curious. I'm just wondering if other people think I'm crazy being with a cross dressed guy.

  • I always say as long as it's legal and doesn't hurt anyone have fun. If you are comfortable with it that is what matters. If you have issues than it will always be an issue for you. My husband likes to watch tranny porn, and at first it freaked me out a bit. Now it is just something he does.

  • I personally wouldn't date a cross dresser, that's too weird. I'd be worried he'd come home one day and go, "I want a sex change," which is totally fine, if you want a sex change then get one, but then you won't be dating me. Several Jerry Springer episodes are coming to mind

    • What I learned is that there is a huge difference in brain chemistry between cross dressers and transgenders. Transgenders start to cross dress at a very early age (between 4 and 11), if guy starts to crossdress in or after puberty, he likely won't become a transgender.

Most Helpful Guys

  • Is this like a daily thing? Where he puts on makeup and goes to the mall. Or is this a "sexual" type thing? Where he dresses up for the "thrill" of being a "lady" for a while when he masturbates. Or does he do it just because he likes the feel of soft silk and lace instead of hard and plain tightey whiteys? If is the latter two, I wouldn't worry too much at all. It's most likely just a way for him to relax and be comfortable for while. See the web page I've put below for a little more insight into the crossdressing. She has many articles and occasional links to others with firsthand experience. As her hubby/boyfriend also wears panties and bras and such.

    web page : link

    You never know, you might be able to share clothes and lingerie in the future

    • Actually I'm not worry at all. I'm wondering what the general opinion about this subject is. If he likes to change his gender. I would support him. Thank you for the link.

    • Okay. Now that I know you're not worried and just want an opinion, here it is. Good for you for being so open minded, and good for him for being able to openly discuss this with you. I see no problem with it. As long as you're both happy. If more people were like you, we'd have a whole lot less strife and stress in the word.

  • Well, I don't know. How do you feel about it? To me it seems kinda werid, but hey - it sounds harmless. If that is his turn on and you like it too, I don't think there is a problem. Personaly I always think it is akward why would a guy like to dress as a woman?

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What Girls & Guys Said

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  • If you both like it and it can make for even more fun "play time" for the two of you, then of course it is an advantage.

  • You should absolutely do it! Men who like to cross dress probably like to serve women. You’d be set for life!!!

  • its a bit weird in my opinion

  • He might want more than just dress up, ie role reversals..etc

  • Well its would be fun and all but would you be happy with friends and family knowing or would you like to keep it private and avoid the obvious reaction.

  • If you get married who gets to wear the dress?

    • If he want's to wear a wedding gown at our wedding, we could arrange an after party... maybe.

    • That would be so fun to be a part of!!!

  • Not if it might come back and bite you in the ass in the future.

    • How would it bite me in the ass?

    • ...