Dirty Talk Advice ColumnThe smooth silky feeling of satin, the empowering confidence of a high heel, the satisfying embrace of stockings; there is a deep bliss in feeling sexy and desirable. When it comes to dressing up, women are offered vastly more variety than men. Is it any wonder some men try on lingerie, realize just how much they like it, and enter the world of cross-dressing?

Today’s column comes courtesy of a reader who is a lifelong cross-dresser and is wondering where they can find someone that likes heels as much as they do. Is an interest in satin a deal breaker or the start of something special?

“I have been interested in cross-dressing since about age 4. My interest is mainly in high heels, lingerie and satin dresses. I’ve never had a partner who was into dressing up the way that I like to dress up…yet. My thoughts are that if I am ever to get into a relationship with a woman who is as into heels and lingerie as I am, my need to dress up would go away. How do I find someone that is as into dressing up as I am?”–Cross-dressing Conundrum

For many of us, one of our biggest missions in life is to find that someone special that we spark with. We try on endless pairs of shoes looking for the one that is the right fit for us. However, most of the time the puzzle pieces just don’t click. The honest truth is that relationships are tricky, no matter what other circumstances are added to the equation. For an infinite number of possible reasons, people are not compatible with you and your wiring. Your love of cross-dressing is an added factor but certainly not a deal breaker.

No Partner Will Cure Your Interest In Cross-dressing

Sexy Cross-dressingThere are partners out there that are the right fit for you, I guarantee it. The tricky part is in finding them and not giving up or getting frustrated along the way. Based on your letter, it is obvious that you have complex feelings about cross-dressing. Theorizing that if you were to locate a partner that was as into dressing up as you are the need would “go away” is very telling.

There is no person out there with a love of heels strong enough that entering a relationship with them will make you want to stop wearing heels yourself. Even if you were able to find someone who spent all day in heels and lingerie, it wouldn’t somehow make you disinterested in satin. Rather than view potential partners as fixes for your love of lingerie, view them as partners that can cherish and accept every part of you, heels included. If they also enjoy dressing up along with you, all the better!

There Is Nothing Shameful About Your Interests

Embarrassed About Cross-dressingCross-dressing doesn’t have to be a shameful guilty thing, it is just a part of who you are. You’ve been interested in cross-dressing since you were four years old—the desire is highly unlikely to go away. The more that you accept yourself, the more likely you are to find a partner that accepts you as well. The first step is to accept that cross-dressing is part of your wiring.

Will your desire to dress up be an added factor in finding someone else to spend time with? Certainly! But everything is an added factor. If you are REALLY passionate about horror films and watching them and attending horror conventions is one of your favorite activities, someone who couldn’t watch horror films would not be a very good partner for you. Finding matching puzzle pieces is always the struggle.

Be Clear And Direct About Your Desires

Honest About Cross-dressingThose that don’t say what they want rarely get it. You find someone who is as into dressing up as you are by being clear and direct about your needs and desires. Yes, it’s probably going to feel uncomfortable and some people are going to judge or reject you. But would you want to be interacting with people that judge you in the first place? If you are honest about this important part of yourself and someone shames you, then they are clearly showing you that they are not a worthwhile investment of your time.

To increase your odds of finding accepting partners, look up cross-dressing communities and support groups. Do some research and invest your time in places that have like-minded people. Don’t hide your interest in cross-dressing or wait for months or even years to bring it up. Pretending like these interests don’t exist won’t make them go away. Yes, when you disclose it, some women are going to consider it a deal-breaker, but some people consider a love of horror films a deal-breaker as well. When one person isn’t the right fit all they are doing is freeing up space for someone that IS the right fit. Best of luck and may you find the perfect shoe sooner rather than later.

Keep it Kinky My Friends,

Want to add your own insight to the conversation? Leave a comment below.
Have a question that you want answered in the Dirty Talk Advice Column? Contact Rain here.

Keep these columns coming.
Patreon LogoSupport Rain on Patreon


Paypal donate button

Love this post? Share it with your friends!


Rain DeGrey

#Cured #CrossDressing #Rain #DeGrey