It Can Be Hard

I am married, and gradually came out to my wife (then girlfriend) that I liked to wear women's clothes. It can be a difficult thing for both, so I wanted to offer some of my expereinces as advice and my mistakes as warnings.

First of all, early on in any relationship you should get a sense of your partner's attitudes. If your other is homophobic or incredibly uptight, you need to know. My other was not, and said she didn't judge what other people liked to do, but at the same time was somewhat turned off by men dressing as women. She didn't care for dresses herself, and rarely dressed feminine except for special occasions.

Pity, because I adore women's clothing.

I would buy feminine attire for every holiday (panties on V-Day, Skirts on B-Day) along with things she would like. She rarely would wear them, but since we are similarly sized, I would borrow them when she wasn't around. Once in a while I would leave them out on purpose, planting questions in her head. If she asked I would say I was admiring it and wished she wore it more.

She would say things like pantyhose are so uncomfortable, and I would respond they feel sexy, especially when worn with silk. She would smirk and say "Like you would know". I'd shrug it off.

She knew early on that I would borrow her undies when I ***********, as tactile stimulation (that is, to feel as I got excited). She didn't like it, but grew understanding that I was more sexually charged than she was.

So seeds were planted. One time I bought her a really frilly, pink silk nightie with lace on the butt and everything, which she looked at and said, "Oh, come on. Do you think I would actually wear this?" 

"No." I admitted. "It just turned me on. And I can't think of anything I wouldn't wear for you if you wanted me to."

Right there I set her up. She fell for it. Perplexed, she asked, "If I gave you something this ridiculous and wanted you to wear it you would?"

"I'll prove it." I took it from her and ignored her protests as I put it on. She was NOT excited by it, but I didn't expect her to be.

"I know I look ridiculous. But if it's just you and me, and it turns you on, I'll do it." I offered.

She asked me to take the nightie off, and I did, but left the panties on. "Actually, they're quite comfortable." I said.

She asked that I take them off, and I turned the conversation on her. "Does this bother you? Why is that? Do you not like feminine attire because you hate women, or are you afraid I might be gay if I wear this pink silk clothing? What is your problem exactly?"

After coming to nothing more definite than "It's weird", I told her that if she was that judgemental about sex and sexuality that she couldn't enjoy a little fun, maybe she should loosen up. I changed into more manly pajamas, and left it alone.

Sometime later I bought her some men's tight boxer shorts as part of her gift, and when she questioned me I said I thought you hated women's clothes, and that you'd like these. Of course, more weirdness. I said, look, I just want to make you happy, and if you want to dress in tighty whities, plaid shirts and man pants, that was fine with me, but I was turned on by skirts, bras and panties, and if she wasn't going to wear them I would. She didn't like my authoritative tone, and "called my bluff".

That night I wore full female attire in bed, and after sex she told me she wanted a strap on so she could really make me feel like a girl.

We don't do these things often - we have kids, which makes any and all alone time rare - but when we get the chance it is hot as hell. I use the internet to vent my sexual feelings, as adult time is far too little these days.



bunchopanties bunchopanties
36-40, M
3 Responses Feb 23, 2009

what if i took you as a girl laura?

wonder what it would be like for her to take me as her girl - I think I would like that. To be completely accepted and treated as a feminine girl, even in bed.

I love taking my sissy boy lover with a strap on when he's fully dressed in bra, panties and stockings. He loves it too! Keep working on your wife. She'll get even more into it.