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!

 

[SammiStarr]

I started a little later. The panties and clothes that got me were my girlfriend at the times sisters. My girlfriend had an older sister who was absolutely drop dead delicious. She was away at university which meant we would stay in her room when I was over. Bigger bed. Anyway it meant I got left in the room on my own a lot playing playstation or whatever.

Eventually curiosity got me and I started going through the underwear draw. It didn't take long for me to start slipping into something every now and then. No idea how I never got caught!

Since then my curiosity and practical time to indulge has waxed and waned. Now here I am over 20 years later still working through the same fantasies.

 

[2tallpaul]

I was exposed to it by my older sister and my widowed mother was ok with it. I married at 21, took a trip to Mexico for a honeymoon. All my underwear were missing and my new wife had me wear hers. when we returned, all my underwear had been replaced with panties. New wife said I wouldn't cheat in panties. some days she would write with a sharpie on me if I was out of town to a meeting. Sex was great but she was bi and we had a ton of MFM but I couldn't last with the women. Divorced at 39 as she said she was gay, ladies only. Still good friends. My rabbit hole started early. I thought being bi was normal for all the women I dated.

 

[Chubnative73]

It started with my sister's friend panties, she had slept over on a weekend. Left behind a couple of panties and by chance I found them in the dryer. Tried them on .

 

[aaronwolf50]

For me it was my aunt. She wore the most delicious white lace panties and conservative, pointy bras. I used to wear her clean ones until rubbing myself against them made me cum, then return them. I was just thinking about visiting her come the holidays

did your aunt ever say anything?

 

[Want2drift]

I hope this is the right place to post this. Does anyone else have only a fantasy wardrobe? I have wishlists and links to the clothes I'd love to have but haven't bought because of my living situation. I've played in panties and thigh highs in the past but I could fill a closet with the stuff I want. I've been flirting with a guy online who I hope to visit one day. I'd love to meet him in public and discreetly flash him the edge of my lace panties; to whet his desires. Well, I have many fantasies. That's why I enjoy this site.

 

[stargame]

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.

Being complimented by a woman for wearing cute panties is just the ultimate, but when a naughty man compliments you, you know, he just wants to get in your panties.

 

[stargame]

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.

https://rule34.xxx/index.php?page=post&s=view&id=18864536&tags=sissy
Dressing right around the pool is essential.

 

[stargame]

https://rule34.xxx/index.php?page=post&s=view&id=18864536&tags=sissy
Dressing right around the pool is essential.

https://rule34.xxx/index.php?page=post&s=view&id=18843248&tags=sissy

 

[liqueur]

Being complimented by a woman for wearing cute panties is just the ultimate, but when a naughty man compliments you, you know, he just wants to get in your panties.

and you do let him, I hope?

 

[hiker283]

I hope this is the right place to post this. Does anyone else have only a fantasy wardrobe? I have wishlists and links to the clothes I'd love to have but haven't bought because of my living situation. I've played in panties and thigh highs in the past but I could fill a closet with the stuff I want. I've been flirting with a guy online who I hope to visit one day. I'd love to meet him in public and discreetly flash him the edge of my lace panties; to whet his desires. Well, I have many fantasies. That's why I enjoy this site.

I saw a Colorado news report today with the weather girl wearing the cutest black dress. It had a full skirt that came a few inches above her knees. I would love to be able to wear that dress. Preferably with bare legs, but with garter belt and stockings would be good too.

 

[Samantha47]

Just wanted to hear everyone's start to crossdressing.

For me I was very young. My sister's panties were on the bathroom floor. I made the choice to slip on her purple panties because of how soft they were.

It only ramped up from there. Any time a pair of dirty panties were in the hamper I would put them on. As I got older I would go to shower right after my mom or sister did, and I could put on their freshly moistened panties. I loved feeling their wet patch against me. I would often smell them, sometimes suck on them while I dug deeper in the hamper for a pair to wear while I did.n

Once I started being home alone, it was amazing. I would raid my mom and sister's panty drawers, found their stockings/hoes and wear them. I especially loved wearing their heels. My sister had some wigs she would wear. So I would of course put those on too.They also had so many skirts and tanks/sexy dresses plus night gowns. I would often sneak a few pairs of panties and clothes in my room so I could wear them at night.

I graduated to wearing their makeup and perfume. And would shower to wash it off before anyone got home. By the time I was 18 I had found some of their toys and would play with them. Even went as far as wearing their dirty pads sometimes. Or using a fresh tampon to wear inside of me with the string dangling out of their dirty worn thong. I would masturbate thinking of my sister's boy friends fucking me and calling me her name.

I can vividly remember my favorite panties, stocking, heels bras, bathing suits, skirts, tops, dresses, night gowns.

I still love to dress up (obviously) but I wish I could find the exact clothes and shoes of theirs that I would wear to recreate the experience.

Would be nice to have those panties of theirs

 

[Want2drift]

I saw a Colorado news report today with the weather girl wearing the cutest black dress. It had a full skirt that came a few inches above her knees. I would love to be able to wear that dress. Preferably with bare legs, but with garter belt and stockings would be good too.

My take is- with bare legs I'm going for comfort but with stockings or thigh highs I want my legs to be noticed. ;-)

 

[Redblack81]

I started with Moms stuff. I luv lingerie. I got married and didn’t do it for a long time. The wife lost the drive so I started using her things to get off. I still wear my wife’s panties and bras. I have to buy my own hose because the wife doesn’t wear them. I also buy my own panties and bras. Being in the store feeling the material and being seen is a whole other thrill for me. I wear my things under jeans at work a lot. Super hot feeling. I would love to be seen and found out by someone who would appreciate it instead of judging or flipping out. My wife would absolutely melt down if she caught me.

 

[hiker283]

TheSocalBreeder said:

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
...............................................................................................

One of my crossdressing experiences was a few years ago. I had to drive across country and decided to do it as a woman. 24 hours a day for four days and nights. Motels, restaurants, etc. Second day I was wearing a black full skirt that came about 4" above my knees and a white blouse, bare legs and sandals. I stopped at a truck stop for coffee and the girl at the cash register said, "That skirt looks stunning on you." It made me feel really good. I loved that skirt because it looked and felt great and looked professional. I just wished I could have stayed dressed for the meeting I had to go to on the 3rd day.

 

[Travis55]

TheSocalBreeder said:

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
...............................................................................................

One of my crossdressing experiences was a few years ago. I had to drive across country and decided to do it as a woman. 24 hours a day for four days and nights. Motels, restaurants, etc. Second day I was wearing a black full skirt that came about 4" above my knees and a white blouse, bare legs and sandals. I stopped at a truck stop for coffee and the girl at the cash register said, "That skirt looks amazing on you." It made me feel really good. I loved that skirt because it looked and felt great and looked professional. I just wished I could have stayed dressed for the meeting I had to go to on the 3rd day.

What an amazing experience! I'm jelly

 

[Redblack81]

TheSocalBreeder said:

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
...............................................................................................

One of my crossdressing experiences was a few years ago. I had to drive across country and decided to do it as a woman. 24 hours a day for four days and nights. Motels, restaurants, etc. Second day I was wearing a black full skirt that came about 4" above my knees and a white blouse, bare legs and sandals. I stopped at a truck stop for coffee and the girl at the cash register said, "That skirt looks stunning on you." It made me feel really good. I loved that skirt because it looked and felt great and looked professional. I just wished I could have stayed dressed for the meeting I had to go to on the 3rd day.

Oh how awesome