Crossdressing orgins

[Travis55]

https://postimg.cc/w7dDz8PJ

The vintage lingerie really pumps my balls!

 

[Happyandgay]

A pair of jeans that my twin sister didn’t like the way her hips looked in them. She raided my closet, I raided hers. Downhill from there. Men’s pants still don’t fit or feel right years later.

 

[Crios]

A pair of jeans that my twin sister didn’t like the way her hips looked in them. She raided my closet, I raided hers. Downhill from there. Men’s pants still don’t fit or feel right years later.

I could’ve gotten away with that before I turned 30. Weighed 130lbs until then. Tight butt, not much in the way of hips.

 

[Crios]

My crossdressing story is less vibrant. I was trolling Reddit and Twitter and came across femboy/ CD fun and decided I wanted to try. I was still a sexual bottom at the time, and wanted to try being smooth and feminine. So I bought a lot of clothes, cages, and wigs and started dressing up.

I got lots of validation from being online. They all thought I was super cute, and eventually I started meeting people while dressed. At one point I even went out on a date with someone while fully dressed up in broad daylight. I got a compliment from a girl saying she liked my skirt as we were walking by

That kind and affectionate gentleman would later on have me bent over in a parking lot while I wore heels and moaned like a slut for him.

I would have a lot of sex while dressing, but eventually I stopped due to lack of time, losing interest, and the maintenance being too much for me to manage. Now I just live as my masculine self, but the ladies in my life do wish I would go back to being cute and feminine at least sometimes.

Do you still wear feminine clothes when just hanging out (pun intended) at home?

 

[LindsayGurl]

My crossdressing story is less vibrant. I was trolling Reddit and Twitter and came across femboy/ CD fun and decided I wanted to try. I was still a sexual bottom at the time, and wanted to try being smooth and feminine. So I bought a lot of clothes, cages, and wigs and started dressing up.

I got lots of validation from being online. They all thought I was super cute, and eventually I started meeting people while dressed. At one point I even went out on a date with someone while fully dressed up in broad daylight. I got a compliment from a girl saying she liked my skirt as we were walking by

That kind and affectionate gentleman would later on have me bent over in a parking lot while I wore heels and moaned like a slut for him.

I would have a lot of sex while dressing, but eventually I stopped due to lack of time, losing interest, and the maintenance being too much for me to manage. Now I just live as my masculine self, but the ladies in my life do wish I would go back to being cute and feminine at least sometimes.

Omg the compliment from a woman must have been exquisite.

It does suck doing the maintenance to be feminine. But it makes me appreciate my wife and the efforts they go through to be sexy. If I was single I would still do the shaving, makeup, and such. But it does take a while and then also the cleaning off the makeup.

I appreciate womens efforts for sure from cross dressing experiences.

 

[LindsayGurl]

Omg the compliment from a woman must have been exquisite.

It does suck doing the maintenance to be feminine. But it makes me appreciate my wife and the efforts they go through to be sexy. If I was single I would still do the shaving, makeup, and such. But it does take a while and then also the cleaning off the makeup.

I appreciate womens efforts for sure from cross dressing experiences.

Well the outfit completes our look sweet heart. She was complimenting you and the skirt.

 

[drobert44]

Well the outfit completes our look sweet heart. She was complimenting you and the skirt.

CD's work hard to look passable; and I always walk them out.

 

[AllenJames]

A pair of jeans that my twin sister didn’t like the way her hips looked in them. She raided my closet, I raided hers. Downhill from there. Men’s pants still don’t fit or feel right years later.

I still have several pairs of women's jeans in my closet that I wear - though I've actually lost weight and they don't fit as well as they did.

 

[AllenJames]

It started with my sister's panties. I also liked how her nighties with their panties felt to sleep in. I moved on to wearing her panties, skirts, blouses, dresses and nylons when I got the chance. Eventually, I was on my own, then married. I now dress up and go shopping as a woman to buy my own feminine things. I only buy my female clothes and shoes when I am dressed. It is all part of the fun.

I still enjoy going up an escalator in a mid thigh pleated skirt and wondering if people behind me could see my panties.

Envy you those opportunities, I would have loved to try a sister's pjs or nighties!