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Men, have you ever crossdressed?

I have since I got in my 50s. I guess it started a few years back and i have added things till i have a couple of outfits. I also have some lingerie. I also bought two paris of shoes, one pair of thigh high boots and one pair of heals.
 
ped1958 said:
Have enjoyed crossdressing since my teens. Don’t get many chances to do it anymore since l’m retired and wife doesn’t know about this side of me. But enjoy wearing her panties and bras when I can. Still enjoy wearing 50 years later
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ped1958, I was doing the same when young. Now days like you retired wife stays home an doesnt know I like wearing her panties an playing with her bra's. still like the feeling of panties 60 yrs later mmmm
 
CurtGiles46 said:
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.
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Not fully, just panties.
 
Easyvirtue said:
I was sitting in my recliner once and my wife got up went to our room came out with my favorite bra and panties threw them in my lap and said “get dressed Bitch!”
She made such erotic love to me that day treating me like a woman as best she could.
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please tell us more that sounds so hot.....
 
storypost603 said:
please tell us more that sounds so hot.....
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Here’s one, on my birthday I asked for our first foray into “water sports.”
She asked for details. As we sipped on our wine I explained how I saw it going down.
1st I told her she couldn’t use the restroom for the rest of the night. (We were leaving soon anyway) Next I told her I was going to take her home and pick out her panties and bra and some thigh high stockings.
I would then pick out my favorite bra and panties and we would meet in the living room. Then I would lay down some towels and I’d be laying on the floor on the towels and she was to walk into the living room sultry and seductive. She would then walk over me till her pussy was right over my face, pull her panties to the side and pee all over me!
Everything played out as I had explained. I was laying there rubbing my bra and stiff cock in my panties as she walked in in her “fuck me heels!” and squatted over me and flooded my mouth with her stream of warm piss soaking my face, filling my mouth and moving down my body soaking my lingerie! She finished and moved to a 69 position and taking my cock in her mouth soaked with her piss and I devoured her piss soaked pussy! Moments later we were both cumming!
After she stopped shaking and swallowing all I gave her she moved to come and kiss me, and whispered “happy birthday bitch!”
It was amazing!
 
I tried wearing panties several years ago. The first time I tried it I realized I was hooked when they were only half way up my thighs. Have enjoyed wearing them ever since. Not long after I obtained a couple of camisoles, which I enjoy as well. Not long ago I was trying some shirts on in the dressing room of my local department store. When I came out of the room I noticed on the cart where you are supposed to leave clothes you are not going to buy a short tennis skirt. The light bulb when on in my head and I grabbed it and went back into the dressing and I tried it on. I loved it and the naughtiness of wearing the skirt with my panties was a turn on. I ended up jerking off in my panties in the dressing room. The skirt was a bit too tight so I put it back and ordered the same dress a size up along with a red lace tanga panty. I’ve bought a few other dresses and some lace socks and dress up when I have the chance.
 
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Some of my earliest memories are of me stealing clothes off of family’s clothes lines and trying them on. I’m sure I got caught, but never confronted…. So, just an opportunistic curiosity my whole life. I’m in my fifties now and have this attitude: OK, these underwear might be designed for women and marketed to women, but I paid for them and I’m wearing them, so they are no longer “women’s underwear”, they’re MY underwear. And they are so F’ing comfortable. I have no intention of going back to cotton. Ever.

As for the rest, my girlfriend bought a pair of Kitten Heels for a wedding and was trying them on. I just asked, “Hey, I don’t mean to freak you out, but I’ve always wanted to try heels, would you mind?” She didn’t, and they were soo cool!! She said they looked better on me than on her. ;) so then I started buying my own heels and skirts and even hose. It’s FUN! Such a different perspective being 4” taller than I usually am. I don’t identify as anything other than Mostly Male. I would NEVER pass as anything but a gloriously ugly girl, so I don’t go out “dressed”, other than one day in a nearby city, I wore a pair of platform boots with a chunky heel in the dead of winter. So much fun. We saw an opera, a hockey game, and had pizza.

So that’s where we’re at. Recently my girlfriend helped me buy some breast forms and a bra. Another amazing, and fun, perspective shift. Seriously girls, how do you ever get anything done with such fun appendages RIGHT THERE!! Of course, I get to take them off when I go to work, or sleep, so I can see where they might get cumbersome….

So, have I cross dressed? I suppose I have, but not in the scary, sometimes dangerous, brave way some people are compelled to so they can live an authentic life. I’m grateful to have the opportunity to do it for a fun, interesting, safe, boost to my sex life.
 
XXXploring said:
Some of my earliest memories are of me stealing clothes off of family’s clothes lines and trying them on. I’m sure I got caught, but never confronted…. So, just an opportunistic curiosity my whole life. I’m in my fifties now and have this attitude: OK, these underwear might be designed for women and marketed to women, but I paid for them and I’m wearing them, so they are no longer “women’s underwear”, they’re MY underwear. And they are so F’ing comfortable. I have no intention of going back to cotton. Ever.

As for the rest, my girlfriend bought a pair of Kitten Heels for a wedding and was trying them on. I just asked, “Hey, I don’t mean to freak you out, but I’ve always wanted to try heels, would you mind?” She didn’t, and they were soo cool!! She said they looked better on me than on her. ;) so then I started buying my own heels and skirts and even hose. It’s FUN! Such a different perspective being 4” taller than I usually am. I don’t identify as anything other than Mostly Male. I would NEVER pass as anything but a gloriously ugly girl, so I don’t go out “dressed”, other than one day in a nearby city, I wore a pair of platform boots with a chunky heel in the dead of winter. So much fun. We saw an opera, a hockey game, and had pizza.

So that’s where we’re at. Recently my girlfriend helped me buy some breast forms and a bra. Another amazing, and fun, perspective shift. Seriously girls, how do you ever get anything done with such fun appendages RIGHT THERE!! Of course, I get to take them off when I go to work, or sleep, so I can see where they might get cumbersome….

So, have I cross dressed? I suppose I have, but not in the scary, sometimes dangerous, brave way some people are compelled to so they can live an authentic life. I’m grateful to have the opportunity to do it for a fun, interesting, safe, boost to my sex life.
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Wow...13 YEARS on Lit, and THIS is your first post EVER? Where have you been all this time....i LOVE it.... :) I'd love to hear more about your amazing GF, who's supported you during this very exciting time!
 
CurtGiles46 said:
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.
Click to expand...
Yes, Just wish I could find a Woman that would like to watch and play with me dressed up or to dress me up Herself.
 
Yes. As a teenager i would baby-sit for a neighbor couple, she was a teacher and had some of the cutest dresses. After I'd get the kid down I would strip off my clothes and put on her panties, bra, stockings and garter belt and one of her dresses I'd wear them till it was about time for them to come home then change back to my clothes and put everything back in its proper place. I don't know if she ever knew what i was doing, if she did she never said. Now i just wear panties exclusively and have been for the last couple of years. Occasionally when the wife is out I'll dress in one of the few skirts that she has and one of her silk shirts. It's such a turn on.
 
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