Men, have you ever crossdressed?

[SuperSissy]

Yes, extensively. Never could pass, but I've gone out in public as a woman, such as where BF dressed me up and paraded me down the street on his arm. Also spent a weekend in Canada as a woman, that was loads of fun!

 

[pantylover1964]

My first matching set

 

[JoeBeans2751]

ONLY on Halloween

 

[sissyfluff]

Men, have you ever crossdressed?

When I was a senior in high school, I came home from school one afternoon and tried on one of my older sister’s pink nightgowns.

As an experience, crossdressing is quite fascinating. Maybe the hottest part is the emotional rush of fear worrying about getting caught. Also, the shocking thoughts of what your school classmates would say if they knew.

During my 20’s, I still lived at home with my parents and I sometimes slept wearing one of my mother’s slips. It was super relaxing, the feeling of sleeping like a girl.

When I was doing a lot of service work, and spending days at a time on the road, I had quite a collection of clothing. I went days sometimes, wearing feminine undergarments. I sometimes went to a gas station and filled up my vehicle wearing a full complement of underwear and a blouse and short skirts.
I had a nice conversation with a lady at the breakfast bar of a LaQuinta in Shreveport, while I had a black “wife beater” tank top over a nice black bra. I was worried about my straps showing, but she never said anything.
Lots of other things. I don’t kid myself that I could ever look like anything but a guy wearing women’s clothing.

 

[Patsysub]

for so many years!

a few other pics

 

[jgurl2383]

I had my first orgasm in my mom's panties and pantyhose. I lost my virginity (23) in pantyhose. I am wearing panties right now. When I married, I thought I was done, but soon started collecting again. Then my wife found my stash and was very upset. Turned out she was more upset about me hiding than my dressing. She embraced it and we began exploring all our fetishes. I was her cuckold husband for a few years. Unfortunately she lost interest in everything and demanded I stop. I am unable to, so I explore a fantasy life online. We no longer have any form of intimacy.

 

[vizio]

I absolutely adore crossdressing. I love the feeling of stocking on freshly shaven legs. In addition to the fantastic feeling of silky bras and panties I love wearing dresses and skirts paired with a nice pair of high heels.

 

[Replicant2018]

I absolutely adore crossdressing. I love the feeling of stocking on freshly shaven legs. In addition to the fantastic feeling of silky bras and panties I love wearing dresses and skirts paired with a nice pair of high heels.

Always so hot and sexy Vizio!

 

[luvslingerie200]

I absolutely adore crossdressing. I love the feeling of stocking on freshly shaven legs. In addition to the fantastic feeling of silky bras and panties I love wearing dresses and skirts paired with a nice pair of high heels.

smoke show

 

[sissycindy59]

Hello I am 61 mwm, I knew from a very young age I was different from the other boys. I Had a female cousin that lived right next door that was 7 years older then me that I admired and worshipped and so wanted to be just like her in every way. So at 6 years old I started out with playing with her used panties out of the hamper, sniffing them and then wearing them wishing I had a body like hers.
At about 8 or 9 I started wearing all her feminine items at loved it I felt like this is who I really was but knew no one would understand. So I have been in the closet my whole life. My wife of 30 years has no idea about the real me. I so wish I had a body like hers.. I wear panties 24/7 for the past 3 years and she has never caught me that I know of and also wear a bra alot.
Sorry this was so long, but love to dress and always will

Cindy

 

[funguy4u100]

I absolutely adore crossdressing. I love the feeling of stocking on freshly shaven legs. In addition to the fantastic feeling of silky bras and panties I love wearing dresses and skirts paired with a nice pair of high heels.

You look absolutely amazing!!

 

[Shaglus_Ziegler]

Men, have you ever crossdressed?

When I was a senior in high school, I came home from school one afternoon and tried on one of my older sister’s pink nightgowns.

As an experience, crossdressing is quite fascinating. Maybe the hottest part is the emotional rush of fear worrying about getting caught. Also, the shocking thoughts of what your school classmates would say if they knew.

During my 20’s, I still lived at home with my parents and I sometimes slept wearing one of my mother’s slips. It was super relaxing, the feeling of sleeping like a girl.

No. But I do like tight speedo type shorts, I wear em around the house and yard sometimes when I’m not nude.

 

[Shaglus_Ziegler]

I have a couple pairs of panties that I like to wear every omcve in a while, but nothing beyond that

Mask?

 

[Justhappytobealive]

I used to…. Loved it. Now I know why women strut their stuff. I’m getting stiff just remembering all the crap I used to do while dressed.

Walk the parts. Go to the bookstores

 

[stargame]

I absolutely adore crossdressing. I love the feeling of stocking on freshly shaven legs. In addition to the fantastic feeling of silky bras and panties I love wearing dresses and skirts paired with a nice pair of high heels.

You are my role model!

 

[Take1]

I crossdressed some in my 20's. Thinking about it makes me remember how damn excited I got.i still ware panties out occasionally now.

 

[BeatMan]

preparing for my shemale on female fun with my white latina FWB in 4 days


https://i.postimg.cc/xjRNbjnw/PXL-20230826-224649476-MP.jpg


i got an erection when i put these on school girl skirt and cropped tank top with styrofoam fake boobs

 

[AllAmericanMale]

Yup.
College.
Was asked to to join the fraternity.
I was kinda cute...

 

[smoothwiener]

Panties, I've tried other stuff but it's not my thing. Plus wife encourages the panties, but not into anything more either.

 

[van_delay]

Of course.

 

[AlexBailey]

Sure, I’ve been a CD since before I was interested in sex - a long time!

I like femme styles but I haven’t been trying to pass, so I don’t really consider it cross dressing anymore, more just dressing gender irreverently.

 

[ryan428]

I absolutely adore crossdressing. I love the feeling of stocking on freshly shaven legs. In addition to the fantastic feeling of silky bras and panties I love wearing dresses and skirts paired with a nice pair of high heels.

Nice body! Great shape and gorgeous legs.

 

[mrdiscreetshh]

Yes it feels AMAZING! particularly thongs for me!

 

[XXVIII]

As a kid I once tried on my cousin's pantyhose. Got me hard as a rock, which is the probably the reason why women in pantyhose are still a huge turn on.

 

[AllAmericanMale]

Just once, in college, when I pledged my fraternity.