Kinky Confessions

How to Enjoy Your Crossdressing Fetish

Man in Wig and Dress

We get a lot of kinky confessions that share fantasies or experiences of men who enjoy dressing up in women’s clothing. Here are two recent confessions, followed by tips to enjoy your cross-dressing kink.

“I’m in Kohl’s, in the women’s department, looking at panties when the sales clerk asks me if I’d like to try on my selections. She shows me to a dressing room where she tells me to have fun. I hear a knock on the door where the store clerk hands me a garter belt and stockings, and tells me to put them on. After I put the items on she comes into the room and runs out with my male clothes, returning with a slip, dress, heels, and a wig. She puts makeup on me and says I can pay for the clothing by working with her until the end of her shift at which time I go home with her.” – Sami

“I was a cheerleader for Halloween in grade school when my best friend’s two older sisters let me put on their stockings and slip—both sisters touched my erect manhood and that was my first sexual encounter. Later on that evening, I ejaculated. It turned me on to my softer side. I’m not gay, but I like to dress in women’s attire and then be told how to pleasure a lady blindfolded and then myself. I would like a woman to take her time and teach me how to dress like a lady, act like a lady, and then lick and suck and fuck like a man. My spouse is completely turned off by this, but I felt like I was lying if I didn’t show her that side of me.” – J.

Dressing up in another gender’s clothing is something that turns many men on, but not so many women. It’s also something that is more often kept a secret, although some men long to share their kink. Here’s a few ideas on how to enjoy crossdressing with or without a friend, lover, or partner.

5 Ways to Enjoy Your Crossdressing Kink

1. Let Your Lover Dress You Up

If you have a partner who is open to your kink, who you are comfortable sharing your kink with, why not let her dress you up. Like our second confession, that is sometimes part of the excitement—to be taught “how to dress like a lady” or even to be submissive. Unfortunately this doesn’t always turn women on.

2. Join a Crossdresser Dating Site

While some mainstream dating sites are free, finding others who share your crossdressing fetish can be like looking for a needle in a haystack. There are many dating sites that cater to kinky people. These sites may be broad like the top fetish dating sites, or specific like these sites for crossdressers. There is often monthly membership fee, but the time it saves looking for women who are into your kink is worth it. And if sharing your kink is important, then it’s worth joining to take a look.

3. Wear It Under, Out in Public

Part of the thrill of wearing women’s lingerie isn’t always about dancing in front of a mirror at home. If you haven’t already, find something that fits nicely under your day-to-day clothes and go out for a walk or meet a friend in the park. Sometimes NOT sharing a kink is part of the kink. This thrill is perfect for men who don’t want to, or are not ready to share.

4. Use a Cross-Dressing Service

Yes, a service exists to celebrate your joy of dressing up in women’s clothing, makeup, jewelry, and more.

5. Find a Munch or Community to Join

Because it’s not a way-out-there kink, you should be able to find a munch—a meetup for folks with similar kinks or BDSM interests in a nonsexual environment—especially if you live in a metropolitan area. A munch can expand your cross-dressing community and provide an opportunity to meet play partners if that’s what you’re looking for.

Kinky Confessions is a regular post on Kink Lovers. We want readers to share their tantalizing tales of kink, fetish, and fantasy. SUBMIT YOUR STORY HERE! These stories don’t have to be real—they can be fiction that you’d like turned into reality.

Tell us what you think!

guest
0 Comments
Inline Feedbacks
View all comments
To Top