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I have been dating Lisa for over a month now. And she does not know that I like to wear skirts, dresses, panties, hose, heels etc. In other words I am a straight crossdresser. Should I tell her my secret or keep it to myself? And ladies would you ever date a guy who sometimes dresses in womens clothes from head to toe?

2006-07-20 11:27:42 · 23 answers · asked by ? 2 in Society & Culture Other - Society & Culture

23 answers

I am a straight female cross dresser. Just kidding. I don't wear skirts or dresses though. In fact I'd be happy to give you some of mine!

Seriously though, unless you want to share this part of your life with her, I do not see an immediate need for you to "volunteer" the information.

If you feel uncomfortable keeping secrets from her, then approach the subject carefully. Make sure you can trust her with this secret if you wish for it to remain a secret. All people have difficulty keeping secrets. Be careful.

I don't think I would mind if I found out a guy I was dating liked to play dress up, as long as it was behind closed doors. I see no harm in it. I don't understand why anyone would want to wear women's clothes, especially hose. They're so uncomfortable. I don't like wearing most of those things, and I am a woman.

2006-07-20 11:39:07 · answer #1 · answered by askme 4 · 10 1

Sure. If she doesn't want to be with u 4 that, u know sh's not right 4 u. There's someone out there 4 everyone. You just have to look 4 her. If u bottle it u and somehow get married, you'll have a guility conscience. Usually mates never keep secrets from each other. That's whats so great about it. Look what happened in the Drew Carey Show.Drew's brother was a crossdresser. Drew's Brother ended up MARRING Mimi!Oppisites Attract!(But I'm not sure about the last part you said)

2006-07-20 11:40:15 · answer #2 · answered by Onyinenycukwu 1 · 0 0

You know what? If you think she can handle it and she'll be okay with it, then tell her. But if you're not clear how she'll react, or she breaks up with you because of it, please don't be one of those people that then comes back and post another question asking why she dumped you after you gave her the news!
No, I wouldn't date a guy that dressed up in women's clothing. It's not because I'm judging you or anyone else that does....To each his own is the way I see it, but it is simply not something Iook for in a guy! I also wouldn't date a guy with long hair....Doesn't mean I think men with long hair are bad, I'm just not attracted to them!
I wish you all the luck in the world with your girlfriend!

2006-07-20 11:41:15 · answer #3 · answered by Naples_6 5 · 0 0

You definitely should tell her, there shouldn't be secrets in a relationship. If my boyfriend was a crossdresser, I wouldn't mind. It would be kinda fun dressing up with him! But it depends on the girl I guess. Anyway, you should get that out in the open.

2006-07-20 11:32:13 · answer #4 · answered by i luv teh fishes 7 · 0 0

You should show up at her door wearing a nice blouse, mini skirt, heels, pantyhose, panties and matching bra. Make sure you have on wig and do your makeup. If she really cares, she will invite you in. If she does not, she will slam door in your face. Good luck! By the way, my husband is a crossdresser and we have so much fun together! By the way, I love your french maids outfit!

2006-07-20 12:30:00 · answer #5 · answered by Anonymous · 1 0

Depends on how serious your relationship is. If you see it not really going anywhere, I would keep it to myself. However if it a serious relationship, and I am not saying leading to marrage, but a serious one, you owe it to her to tell her. Trust me it is easier to tell her early on rather than wait down the road. Also don't tell her by showing up at her house all dressed to the nines. Tell her let her digest it, give her what information you have. There is a wealth of infomation on the web. When she is ready, you can dress for her. And if she really loves you she will accept you for who you are, accept the person that you are. My wife is awesome about my dressing, but I am expected to respect certain boundries. I am sure that if she loves you she will accept you.

2006-07-20 11:56:29 · answer #6 · answered by JML 3 · 0 0

Well I dont really know that answer cuz if you heard a woman was wearing your clothes while you were gone sometimes men seem to think that is sexy.....but if a man tells me he was wearing my clothes while I was away, Id be really freaked out and I wouldnt think that was sexy at all. I would be concerned that hed ask to go out in them and that would be too much. If she finds you sexy looking like a man, just think she likes me this way. Why do you like to dress up like that? Is it your inner sexuality that is in question? I would never date a man I didnt find to be manley.

2006-07-20 11:36:15 · answer #7 · answered by c g 3 · 0 0

Honestly, if she has a problem with it, maybe she isn't the girl for you.
I personally wouldn't have a problem with it, it takes a real man to wear heels. And if that's what you're comfortable in, what's the problem? Girls wear guys' clothes all the time.

2006-07-20 11:39:05 · answer #8 · answered by me41987 4 · 0 0

Yeah you should tell her- It's a part of who u are. But don't fret: Tyler Perry makes millions dressing as Madea. (In Madea's family reunion, Madea goes to jail, diary of a mad black woman...) It's seems to be a lucrative business. I'm not sure if i would date a guy like that, it depends on what kind of personality he has- that's what matters.

2006-07-20 11:32:29 · answer #9 · answered by S D 2 · 0 0

yes ~ you should let her know. keeping this kind of secret could make you very withdrawn from the relationship. plus its better she hear it from you, than find out from someone else. there have been people who accept this kind of thing, she might be alright with it. as for me personally, i don't feel i could be with someone who wants to wear my cloths, i like men in mens clothing. but that's just me. best of luck

2006-07-20 11:36:37 · answer #10 · answered by Anonymous · 0 0

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