#ASKMILAN

#ASKMILAN: Would you date a crossdresser? Husband Surprises Wife with Matching Panties

By  | 

Crossdressing couple

Lawd, I don’t think I am experienced enough to talk about guys who play “dress-up” in the bedroom, but one thing I do know, it’s far from drag.

Here’s what we found in our inbox:

“Hi PrinceMilan,

When [I] first started dating my wife, she didn’t have a large lingerie collection because she was still in college. But when she graduated a year later, I had bought her a few nighties and gowns shortly after we became intimate.

I hid my love of lingerie from her until she commented on how she wished she had prettier panties to wear for me, so I surprised her with a few pairs of nylon bikini panties I noticed she liked wearing and she loved them.

When she graduated college and was interviewing, we went shopping at Dillard’s to get her a few dresses, skirts and blouses and shoes with her graduation money and I told her she needed new lingerie. I am still surprised that she didn’t pick up on my “love” for female clothing. So, she picked out a few matching bra and panty sets, a few extra panties she liked, a full slip and half slip with a matching camisole that she wanted. I told her I wanted to pay for her lingerie which she said OK. The next day I went back to Dillard’s and bought a garter belt that matched the white bra and panty set she bought, sheer nude garter stockings and a pair of white satin panties that matched her panties in my size.

She was my date to my company awards banquet and wore her white bra, panty and garter set and full slip under her gown and I wore my white panties under my suit without her knowing. Afterwards back at our hotel, we started undressing each other and she found out that she liked me wearing matching panties with her as much as I did.

Afterwards we just laid there, both smiling, no words, no embarrassment, just love. I would say the best thing I have done is open up to my wife. The rest is history and 32 years later, we are still crazy in love with each other.

Welp, while I have no words and couldn’t possibly date a crossdresser, I can only agree with couples who want to try new things in the bedroom. The point of roleplaying is to take on this new role, to become someone else, act like them, and stop being you. When speaking to a few of my friends about role-playing, they all had the same answer: “It actually helps to spice up ones boring sex life.

So, my question to you is; would you date a crossdresser? Do you think it opens the door for a straight guy going left (wanting to experiment with another man)? Or would you end your relationship if your significant other decided to let you in on a freaky fetish they have bottled up that you can’t fantom doing in the near future? Let me kn0w in the comments below :)…

Prince Milan newsletter

SIGN UP TO OUR NEWSLETTER

* indicates required
Prince Milan newsletter