Behind Closed Doors: How Sex Works After You Start Crossdressing

How Sex Works After You Start Crossdressing

There's more to all this than just a pair of stockings, a good push-up bra and high heels in your size, for both you and your partner. With that, let's get personal. Whether cross-dressing is primarily a sexual kink or you're finding yourself moving toward a physical transition, this will impact your sexuality and your sex life with your partner. An honest discussion of the nitty-gritty is something that doesn't happen often enough. I'm working on an assumption that you want to maintain your relationship and the two of you are committed to one another. While I'm using female pronouns for the partner here, I think that most of this will apply regardless of gender.

If it's really all about the sex for you, at least for now, working dressing up into bedroom play may not be so hard. Talk it through and define both of your boundaries, just as you would for any other sexual fantasy. This is a good time to talk about what each of you needs and wants from this experience and about your fears and discomfort. Take baby steps and start small. Treat this as role play, making it something fun. Written erotica, a visit to an adult toy store or an appropriately themed video may help to provide the two of you with a bit of inspiration, if you're floundering.

Women's magazines are full of advice about getting yourself in the mood. Take advantage of these tips when the night comes. While it may be a bit sappy, it works if you're feeling nervous, regardless of chromosomes. Send the kids to Grandma's house, relax and have a glass of wine. Laugh together. While no one mentions this, put your lingerie on early in the night, before you have a chance to chicken out! There's nothing worse than breaking the mood when you excuse yourself to put on a garter belt and stockings. We've covered the easy part of this question. Integrating dressing up into your sex life isn't necessarily difficult, especially when it's about sex for you, not gender. Managing life in the bedroom when you're feeling confused or struggling with your own gender identity is hard on both of you. Even if you're not taking physical steps toward transition, you may find your libido is low or you're just not feeling quite right about sex or about certain sex acts. You might even find that acceptance increases your libido. If you are transitioning, hormone treatments and androgen-blockers will change your sexual function in significant ways.

You have a few key responsibilities here. First, you owe it to your partner to communicate openly about what you're feeling about your body and sex, and if necessary, about changes in your feelings. Some T-girls are fine with maintaining a traditional sexual relationship with a female partner, while others may be more comfortable looking for sexual activities that feel more feminine and less traditionally masculine. If you're not okay with using the appendage-that-shall-not-be-named or having it touched, say so. You might be okay with some sex acts and not others or with pleasing her even if you're not comfortable without your panties. Keep in mind that her libido may be just fine, even when yours isn't. Making an effort to find sexual activities that work for both of you can help to preserve your relationship. Women manage to have perfectly satisfying sex with other women all the time, but it can take a bit of extra creativity to get there, if it's new to the two of you. Regardless of whether you're okay with sex or not right now, you do need to prioritize maintaining physical closeness. If sex is a no-go, cuddle, hold hands, give each other back rubs.

All of this implies that there's still a mutual attraction, desire and willingness to work through the challenges that can come with crossdressing or gender identity issues. That leaves several big what-ifs. You may find that you're attracted to men or other T-girls. She may not be attracted to you when you're presenting as a woman. In either case, a trans-friendly counselor can help the two of you stay together or split up as good friends, even if you're no longer functioning well as partners.


  • christina

    Hi its Christina again. I posted an article recently about an upcoming date I had with a man. I met him once before at a party and we had been in email contact for over one year. I was ready for my date, all dressed up, excited, nervous and waiting in my nice hotel room. He never showed up, unbelievable! and he had said so many times how excited he was about it too and couldn't wait etc. right up to that day. and he has not responded to my emails or calls since…..looser. I think all he wanted was the pics of me that I occasionally sent him.
    I was bitterly disappointed and upset, however I a over that now and going forward. I still want to meet a nice man, but how? where? All the dating sites of CD's just seem to be for sex….I want to have sex with a nice man eventually but I would have to really like him first and be romanced. How do I go about meeting someone like this…does anyone know/have any suggestions? I live in the New York area. THANKS!


  • christina

    I am a mature crosdresser, 50 yrs old. Due to family circumstances I haven't been able to go out for a long time, but that has changed now. I have been out by myself and to a tg party. I met another tg there and we got along great, However I want to have sex with a man, its what I have fantasized about for ever! My friend is meeting me as a man and we are going to another tg party after which I hope to have sex with him as a straight woman I am nervous and excited. Never had sex as a woman before I am hoping that it will be wonderful but am afraid that I may have a problem 'fitting him in'. never done it before and can't wait but a bit nervous….any advice from experienced girls?

  • Elena

    To sart with, I'm delighted as I'm and so I needn't hormone treatments. The only thing I must confess you, when I`m dressed up I feel a diferent person. Honesty, when I see my image in the mirror or in the pictures, something in burning inside of me. Fortunately it doesn't mean a sexual obsession but I do it ocasionally to break the rutine in my boring life.
    My best wishes from Spain.

  • Patricia Kay

    I’ve been crossdressing and wanting to be a woman since well before puberty. A few years ago I was diagnosed with Gender Dysphoria. This helped to explain a lot about my feelings and the desires I have when crossdressing. My therapists, yes plural, have indicated my sexual desires and preferences are not that unusual for someone like me.

    This article started about being honest, so here it goes. I am Patricia. Patricia likes the sexual company of both men and women. My girlfriend and I have spent hours with her telling and showing me how to be a woman and how to be more feminine. We have spent hours discussing the most intimate details of our lives, including discussions of sex. These have included discussions of what it is like to have sex as a woman. Though I know that it is unlikely at this point in my life to fully transition and enjoy sex as a complete woman I must say that the sex, with both men and women that I have had the pleasure of experiencing while being Patricia have been immensely satisfying. Before each experience, I made sure we both know each other’s boundaries so we could both enjoy the moment.

    Oh, BTW, when I am not crossdressing, I have absolutely no interest in men. To repeat, my therapists say this is not unusual.

    In closing, let me repeat with how this article started, be honest about yourself and what each of you want from any sexual encounter. Sex can be very pleasurable but only if you are honest with yourself and the person you are with.

  • Casey

    I dress up for my wife all the time when we have sex it has become like second nature. Weather if its just a pair of panties or full lingerie, maybe a short skirt or dress our sex life has never been better and she really likes it when I do dress up. I had to tell her that dress up in womans clothes when she found my panty stash. I thougt I had them hid good and she thought I was cheating on her so she had to know. So far she is the only one that knows I am not sure how my family or hers would take it or if they would even except it. It hard not to want to tell someone though. I have lived with dressing up for about 33 years, I was like five when I put on my first pair of panties. I hope that other people have that special someone who let's them be themselves weahter in the bedroom or in life dealing with being a closet crossdresser has been rough for me at times but has turned out to be more rewarding now. Good luck to everybody out there and don't give up hope.

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