Men, have you ever crossdressed?

[Crios]

I used to use my sisters and mum's stuff in my teens (they didn't know) and once, later in life, I went to a place near Euston for a full makeover - prospect exciting, reality a flop - pardon the pun!

Oh, I'd to do that. The missus might object, though

 

[RideFl71]

Yes...
Yes I have and still do time to time.. Being 52 I don't have the body to feel as good in sexy things... But they still make me feel good and turn me on.

 

[Dave60ga]

I grew up in a house with three older sisters. Their clothes were always far more interesting than mine. Yeah, I liked to try them on and walk around. I did that until I outgrew them. Still think about it.

 

[Adventurouscdm]

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.

LOl the way you said that made me crack the hell up

 

[dobbins1]

Only time was trying on my wife's pantyhose while nude. Didn't do anything for me. She never could figure out why that particular pair were so stretched out!?!

 

[Adventurouscdm]

With 20 years of crossdressing experience under my belt (pun intended) I have put on makeup, jewelry, been through a few wigs and even bought a breast plate with what I though were going to be big tits but after trying it on I immediately wanted bigger ones lol. Most of my clothes I've stolen from my wife...something hot about it I guess. The weird thing is whenever I dress up I usually go right for the internet porn and as soon as I cum I immediately strip down and put my regular clothes back on and go chop firewood or something lol

 

[Ciceri]

My sister dressed me as a girl for Halloween when I was eight. She's nine years older. We went door to door and not one person thought I was anything more than a little girl. It felt right for me. Even though I wore my own underwear beneath the petticoat I felt totally normal. It wasn't my idea to dress as a girl but my sister must've sensed I'd be more than okay with the idea

 

[Escierto]

I really don't understand the appeal of cross dressing. Most men look like Gene Hackman did in "Birdcage". I have only ever seen one cross dresser who looked good as a woman, and he/she was a pre-op transsexual. I'm reminded of the hilarious segment in the movie "Everything you wanted to know about Sex but were afraid to ask"

I don't think she looks like Gene Hackman but who knows? Maybe she does lol.
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[Ciceri]

I don't think she looks like Gene Hackman but who knows? Maybe she does lol.
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Any guy who has a beautiful face like this is totally blessed.

 

[Escierto]

Any guy who has a beautiful face like this is totally blessed.

I once told her if she wanted to be a gay guy that was fine with me. She declined.

 

[Dave60ga]

My sister dressed me as a girl for Halloween when I was eight. She's nine years older. We went door to door and not one person thought I was anything more than a little girl. It felt right for me. Even though I wore my own underwear beneath the petticoat I felt totally normal. It wasn't my idea to dress as a girl but my sister must've sensed I'd be more than okay with the idea

I would have loved it if my sisters dressed me like a girl

 

[Ciceri]

I would have loved it if my sisters dressed me like a girl

After she eloped at 18 I had access to her room and wore pretty much everything in her closet and drawers

 

[Dave60ga]

After she eloped at 18 I had access to her room and wore pretty much everything in her closet and drawers

Mmmm like heaven

 

[Ciceri]

Mmmm like heaven

I spent many hours in her room trying on clothes. If my parents were gone for the day I'd put on makeup and fill her bra with water balloons. There was nowhere else I'd choose to be. Once I was fully dressed I'd leave the room. A few times I went outside if I felt bold. My first orgasm was during one of these dress up days

 

[lowcollar]

Once in a great while. Fake breasts in a pink bra, high heels, makeup, lipstick, pink assless panty hose. I hope she makes me shave my armpits and legs. She makes me walk around the house like a street hooker or model swinging my hips. Then, if I am lucky, she uses the squirting dildo and forces oral and anal.

 

[AlwaysDancing]

LOl the way you said that made me crack the hell up

RoFL. At the time I definitely wasn’t laughing. Felt really ridiculous. But looking back … definitely worth a chuckle.

Who knows. Next time I need a chuckle …?

 

[P0peye]

While I will always defend anyone's right to do whatever excites them as long as they're not hurting others, I still have a hard time understanding why a man would feel compelled to dress up in a woman's clothes when he clearly has no feminine characteristics. I've read that transvestism isn't the same as homosexuality, so where is the appeal? Although I love sucking cock, I've always considered the female form to be the epitome of sensuality. I'm sure that I would make an extremely ugly woman were I to wear clothes that are designed to accentuate feminine curves. Just my 2 cents. I'm reminded of the scene in "Birdcage" with Gene Hackman in drag, or the hilarious clip in "Everything you wanted to know about sex"

 

[stargame]

You need only to slip in a pair of soft satin panties to find out. The fabric, the feel, the sensual experience....I find it Liberating.

 

[squirrelmanCD]

Just got new pair of heels and pink gown yesterday. I felt great and still do.

 

[herpanties75]

While in high school, a friend's brother told her he wanted to go to a Halloween party dressed as a cheerleader. She asked me help her with his makeup and getting him sorted. Ultimately he looked a bit ridiculous and wouldn't have convinced anyone he was a woman but I remember him being nervous, or embarrassed at first as we worked on his face. By the time we finished he wanted his nails painted. At the time it didn't arouse me, but a few years later a guy I was seeing floated the idea of dressing as a woman for another Halloween party and that really turned me on. He eventually chickened out unfortunately. I've wondered if my old friend's brother enjoyed himself herself at that party.

similar to a party my now wife and I went too

Guys were dressed as women (prostitutes) and the women as their pimps.

I was in her skirt and a blouse with a wig, got change at the party but went home dressed in a taxi. Wish had asked her to let me wear her lingerie under clothes with stockings. Really get into the character, wish had another fancy dress party to try it again.

 

[Liquidmess1]

With 20 years of crossdressing experience under my belt (pun intended) I have put on makeup, jewelry, been through a few wigs and even bought a breast plate with what I though were going to be big tits but after trying it on I immediately wanted bigger ones lol. Most of my clothes I've stolen from my wife...something hot about it I guess. The weird thing is whenever I dress up I usually go right for the internet porn and as soon as I cum I immediately strip down and put my regular clothes back on and go chop firewood or something lol

Lol. Is chopping firewood a euphemism? Do you ever chop firewood as a crossdresser? I'm not being critical, it just tickled me. I love panties, stockings, garters, skirts. I don't look feminine but I get so aroused and love the feel of the silk and nylon on my legs and dick. Love dressing w/others and playing

 

[gor5619]

I have never fully crossdressed but I love wearing stockings and suspenders when I have a wank. I like the feeling of nylon on my legs.

 

[Britva415]

Men, have you ever crossdressed?

I experimented with it a very little bit when I was in high school. I guess it's not really my thing because I'm not motivated to do any more of it.

My dad caught me in a bra once a few months before I came out as bisexual. Luckily it didn't belong to any of the ladies in my household. He opened my door to tell me it was time to get up, and I sat up and the blanket fell off before I realized I still had it on.

I told him it was a dare. I'm imagining his thoughts: "On the plus side, took a girl's bra home. On the other hand... wearing it!?"

 

[gor5619]

I sometimes think about going online to find men like me for a meet, always bottle out of it.

 

[Nadinet]

love dressing en femme, feels so liberating