How much have you crossdressed?

[CurtGiles46]

How much have you crossdressed?

It’s something I’ve done since age 18. I started out sleeping in my mother’s slips. Soon, I was wearing bras, panties, and pantyhose under my male clothing in public.

I think it was the taboo nature of it that aroused me the most. I also felt excited by the fear of getting caught.

 

[bi_cpl_with_crossdresser]

I am sure I have posted this before, but....

I started around 7 or 8, of course, the only clothes I had access to were my mother's. Later on, I would try playing with her makeup, which always went very wrong. I would also sometimes sneak into my grandmother's house when she was gone and try on her lipstick.

I had a big gap where I could not dress until I started dating my then-GF (now wife) and she was nice enough to lend me some clothes and help me buy makeup. I really did not start to amass any clothes and makeup until we had purchased our own house. At that point, I started to pay attention to how I was presenting and wanted to try and improve my makeup skills. But still, I could go years without wanting to dress or thinking about it at all.

Fast forward to about a decade ago and the thoughts of dressing just settled into a place where given the chance I will dress whenever although fall and winter are my preferred times because of the heat.

 

[Escierto]

I have never cross dressed nor have I ever wanted to. I say this as someone who is a pure bottom for my well hung top girlfriend. So I guess one thing has nothing to do with the other.

 

[Cardinal]

The furthest my fantasy was ordering and wearing my 7 days of the weeks panties from Manties.com they were beautiful and comfortable

 

[van_delay]

This much.

https://ibb.co/02nKSzG

 

[Kellieskirt]

Started early teens sister in law panties and got a skirt from thrift store, now a days when where I get the chance stockings panties skirts ect luv it so much

 

[LilyField]

How much have you crossdressed?

It’s something I’ve done since age 18. I started out sleeping in my mother’s slips. Soon, I was wearing bras, panties, and pantyhose under my male clothing in public.

I think it was the taboo nature of it that aroused me the most. I also felt excited by the fear of getting caught.

my WIFE donated all my boy clothes.
SHE now has complete control on what i can wear or not wear.

 

[JudyCD]

I did for one summer when I was much younger, then I started dressing again a few years ago when a married man visits me to get serviced.

 

[Cardinal]

This much.

https://ibb.co/02nKSzG

Cute, when was this, how often do you go this? Feel free to DM

 

[FeelingLikeMyself]

On and off since I was 21. I'm 43 now. I'm doing it more often now that I have a partner who understands and supports.

 

[Deleted member 1405174]

Bras, panties, teddies, babydolls, skirts

 

[jp8155]

my WIFE donated all my boy clothes.
SHE now has complete control on what i can wear or not wear.

You're so fortunate.

 

[bicuriouscd]

The first time I got caught by my Mom wearing my sisters bra and panties I was six years old , once I accepted and embraced my feminine side I wear a minimum of a bra and thong or bikini panties all day every day.
Even after all the years it's still thrilling slipping into my feminine things when I get dressed every morning !

 

[Ciceri]

I got dressed up completely for a Halloween party. My wife's friend's husband was so troubled by my appearance he kept looking at me and then away when I looked at him. I think I looked damn hot and he agreed I remember later that night my wife and I got undressed for bed and she said, "Why are you wearing panties? You didn't need to wear panties beneath the dress. Where did you get those anyway??" I got em at the thrift shop with the other stuff. I remember standing there erect beneath the nylon grannies. I should have come out that night

 

[aaa666]

I've been out for a day where I was wearing a skirt with panties under it. The top half was a t-shirt over a padded bralette, which felt a bit different but not in a bad way

 

[Deleted member 1405174]

Bras, panties, teddies, babydolls, skirts

Add bodysuits, and heels

 

[wifes_fag]

I couldn't find the right size clothes but loved it. I got some girls shorts one day at a local garage sale. Mom said they were and I kinda acted like I didn't know but since I had bought them she said I had to wear them. I done some research on my girls size and kept my eye out for more as time went on. Mom didn't seem to mind as long as I was buying them. I started shaving my legs at the first sign of hairs. I guess she realized it but didn't say anything just that my legs looked good. i got involved with an older 43 year old man just as I was getting out of school. I would even spend the night sometimes on weekends with him. He really pushed crossdressing on me. He wanted me for his girlfriend. That summer I began wearing dresses quite a bit with him. I done makeup and he had my ears pierced. I was really apprehensive at first but loved it too. After a few times I was a lot more at ease except when he introduced me to acouple of his friends unexpectedly. But by that time I didn't mind it much. I got to doing it on my own while going to college. My wife knew right from the start and I done it a lot with her.

 

[smoothwiener]

Tried it once didn't really do much for me past the panties. That part I liked.

 

[Lingerie_Dreams]

How much have you crossdressed?

It’s something I’ve done since age 18. I started out sleeping in my mother’s slips. Soon, I was wearing bras, panties, and pantyhose under my male clothing in public.

I think it was the taboo nature of it that aroused me the most. I also felt excited by the fear of getting caught.

I started at around seven or eight with my mum and older sisters lingerie and heels ....Ive never stopped since. Only underneath my male clothes when I go out, but at home I will wear it all openly, especially when masturbating, I wear panties all the time, my wife knows. I love vintage Lingerie, fully fashioned nylons, slips, girdles etc, but all lingerie excites me and feels good, I have a very fem side that only a few people know about, no one else would guess. But women are my main interest Guess I'm a lesbian trapped in a male body

 

[eroticbum]

Once in a while I would wear my sisters undies as a child. Then just a few years ago I tried wife's panties one day, and it felt good. Her bra also fit me. Then I started to buy my own panties, after she discovered my stash we had an embarrassing discussion. Once she was assured I am not gay or the panties were that from another woman she accepted my fetish, as long as she didn't see me wearing them. Her lack of sex drive had me seeking other relief options, and I found pleasure with a variety of lingerie items. Never dresses - just lingerie. Love the silky material on my skin

 

[Flyover3]

I started at around seven or eight with my mum and older sisters lingerie and heels ....Ive never stopped since. Only underneath my male clothes when I go out, but at home I will wear it all openly, especially when masturbating, I wear panties all the time, my wife knows. I love vintage Lingerie, fully fashioned nylons, slips, girdles etc, but all lingerie excites me and feels good, I have a very fem side that only a few people know about, no one else would guess. But women are my main interest Guess I'm a lesbian trapped in a male body

I wear thongs and thigh highs all the time. I love my cheeks feeling bare and the string pressed against my rosebud.
I don't get to wear a bra often enough.

 

[frosty3610]

I love wearing panties

 

[xdresssissytoes]

I dress daily to one extent or another.....always in pantyhose or tights this time of year......sexy sandals around the house....tight fitting women's active wear tops....

 

[Bisnjguy]

I most always am wearing sexy lace panties most of the day. Have a large collection along with lace bras and bralettes. Love the feel of lace.

 

[herpanties75]

I got dressed up completely for a Halloween party. My wife's friend's husband was so troubled by my appearance he kept looking at me and then away when I looked at him. I think I looked damn hot and he agreed I remember later that night my wife and I got undressed for bed and she said, "Why are you wearing panties? You didn't need to wear panties beneath the dress. Where did you get those anyway??" I got em at the thrift shop with the other stuff. I remember standing there erect beneath the nylon grannies. I should have come out that night

Yes you should have