Men, have you ever crossdressed?

[CurtGiles46]

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.

 

[Indianabone]

I’ve worn panties and panty hose out in public several times but always under my clothes. I’ve worn lingerie many times at home.

 

[womaneater58]

I have not but I do think about being with a guy who does.

 

[surferjake]

Yes, but there tends to be a misnomer that men who cross dress also are gay or bi. I personally don't find men attractive at all, regardless.

And I don't think it's as much the fear of being caught, but the exploring of the role reversal - getting in touch with one's 'feminine' side as it were.

 

[Escierto]

Even though I am exclusively a bottom for my transgender girlfriend, I have never cross dressed nor had any desire to do so.

 

[CuttingEdge]

I am not sure if I cross-dress now or not...

With heavy equipment sometimes you just need the right machine for the job, and I needed a bulldozer to push several feet of snow out of a roadway a mile long. It was well below zero(F) with the wind howling, but trucks were coming to haul off the wood I had cut all winter, and so it needed to be done. The problem was, my bulldozer did not have a cab.

So I bulked up, layers and layers, but one layer the wife suggested was wearing a pair of her leggings. It would be an extra layer without being thick so I could get another layer on me. Years earlier a foreman had suggested wearing pantyhose under clothing for the same reason, and that guy would work in any weather, all night, and never complained, so I knew the wife's suggestion had merit. So I did, and while I did get cold, I realized leggings were far more comfortable than the sweatpants I typically wore as they were too thick. Long Johns always made me itchy, so from then on, in the cold, I wear leggings under my pants.

But I am not sure it is cross-dressing. While leggings were once considered female attire pretty much, now they are more unisex, kind of like how sweat pants morphed from their early years. Today, I wear leggings all the time. My daughters and girlfriend have just gotten used to it. At the end of the day when I'm in the house, I put on leggings to lounge around the house. As I type this, I am wearing leggings.

But is it cross-dressing?

I am not sure because I don't wear them to specifically feel feminine or give me a sexual rise, they are just tight-fitting, soft pants to lounge in because they are comfortable.

 

[millieteases]

Since I was a child. Began with panties and went from there. Have a full wardrobe now, frequently spend a quiet day at home dressed. Wear panties more often than boxers. Spent a week in Las Vegas with a large group of other crossdressers, only rarely going out in male attire. Figured out eventually that I am nonbinary since I enjoy and celebrate both my feminine and masculine identities.

 

[JudyCD]

I wore a dress a few times when I was younger and I dress now when I’m entertaining a married man who needs my services. It makes him (and me) more excited.

 

[AlwaysDancing]

I have. I put on some lady’s pajamas. And I went in thinking I was going to look kinda cute and I was curious. What I saw was NOT cute and that was the end of the experiment for me.

 

[bux_fan]

Underwear and lingerie only. Nothing outside.

 

[Goldenfinger]

I’ve never crossed dress but once I put on my wife’s frilly silk kimono robe to check on something. when I got back upstairs my wife took a bunch of pictures. But I’ll tell you it was soft and comfy.

 

[AllenJames]

After the usual introductions to lingerie and trying out things of my girlfriend's or wife's, I did finally get (with wife's knowledge) my own panties, bras, shirts, women's jeans, shoes and boots. I have actually gone out in women's flatsoled booties, jeans, panties under tights, a bra and tank under a shirt and sweater - but no makeup, wig, or forms, -

 

[Tardisblue]

I wear bra and panties occasionally.

 

[Kellieskirt]

Yes luv it panties are the best but stockings and a skirt oh so fun I have leggings, few skirts, bras, different type of panties heels boots ect have a wig and luv some make up

 

[Tayloroc]

Absolutely.slipping thigh highs on is so so electric

 

[BrokenQuill]

I dressed up as Magenta from Rocky Horror. I felt that I was totally unconvincing but still had my balls groped by a couple of girls anyway as they "wanted to be sure".

Apart from that I'm afraid it really doesnt apeal to me, but some guys can look amazing

 

[HoldYouDown]

For school drama and such. I grew up on Monty Python and Benny Hill, lol.

 

[OlderBtm4U]

Does dressing as a girl for Halloween once when I was a kid count?

 

[Womanluvr]

I find wearing her panties makes me so hot! Seeing myself in panties not so much.

 

[PleasePeesMe]

One of the highlights of my sex life was, at the suggestion of my wife, buying black stockings and a suspender belt (to match hers). She helped me put them on, donned her own and we settled down for a memorable fuck.

 

[Tayloroc]

Same with my gf

 

[davidsteele]

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

 

[Nadinet]

started with my older sisters bras and panties at a young age, loved the feeling, progressed onto tights, dresses etc.... love dressing en femme in anything from a posh frock to a swimsuit. I far prefer dressing in something previously occupied by a girl to something bought.

 

[Sigmund7]

For me, it's panties or commando all the time. In addition I will sometimes wear a bra and/or camisole (mostly in the cooler months). I am also a fan of kilts and skirts. For you guys who have never tried it, there is nothing as comfortable around the house in the evening as a skirt. In the winter I wear a nightgown or satin sleepshirt to bed but in the summer I prefer nude. In short, if crossdressing is defined as wearing clothing typically associated with women, I guess I have crossdressed.

 

[Tayloroc]

It feels so good. It makes me blush and smile!