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Men, have you ever crossdressed?

I wear panties regularly. I have quite a few skirts but don't get to wear them as often as I'd like to as a lot of people I know would have issues with it. When I go in hotel pools now it's usually In women's bikini bottoms. I have also tried stockings, bras, dresses and sleepwear
 
Not really a crossdresser. But my ex-wife got me hooked on wearing her pantyhose and panties, years ago. I already had somewhat of a fetish with this. I use to watch my mom walking around the house in her pantyhose, panties, and blouse. While she was getting ready for work. It was such a turn on in my adolescent years. And she knew it!!!!!!!!!
 
Like many here, dabbled in my childhood/teens but mum's were far too big. Couple of sis-in-laws' had sexy lingerie when I babysat which I sniffed, felt and tried from the hamper only! Later at college (18) I met an older woman (31). Had dinner and wine one night and made sure she 'caught' me in her panties - testing the water so to speak. Luckily she loved it and soon bought me a bra & panty set. It became a thing for us and she added stockings & suspenders and would have me parade for her then wank and eat my cum off wherever she had me spray it - her tits were a favourite. 🥰 We were together 10 yrs but it was only ever lingerie under street clothes. She was adventurous in lots of ways I am grateful for long after we split. I was buying my own lingerie by then and loved to visit lingerie stores and be assisted with fitting a bra and getting matching panties. I added a camisole and nighty to the mix.

Then met my wife who disapproved totally so back in the closet (actually hid my stash under the bottom drawer of the big chest of drawers in our bedroom!). Together 17 yrs but drifted apart, so single again and back in sensual lingerie regularly. Hung the washing yesterday in my bra & panties. 😊 Never would pass as femme - the full beard is a bit of a giveaway - but added 4" heels to the mix. When on holiday, I find the local CD friendly stores, though Target/K Mart are good options for cheaper items. Loved a shopping trip in a country town Target, where I chose the bras and matching panties and took them to the changerooms to try on. The young lady who counts how many items you take in and gives you the hanger smiled when she saw what I was carrying. I came out and hung up what I didn't want and went to the checkout only to find the same young lady (20s) serving. She was lovely and smiled as she asked, "Did they fit well?" and then reminded me that panties were non-returnable due to health rules. I said yes they fit perfectly, and it was fine as I knew my panty size and bought them and left. That has been my experience with the majority of ladies in stores - friendly and helpful. So now it's panties most days and other lingerie occasionally - I love the sensual feel of wearing. Still love going shopping knowing that, having been fitted, my bra fits better than most women I see. 🤣 So tempting to say, "Just buy a cup size bigger so you don't have pillow tops!" but I do value my life. 😁

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I wouldn't say I'm a cross dresser, but I am a true panty sniffer and have been guilty of stealing a ladies undies from her clothes hamper, then wearing them the next time I/we go to their place. It's such a turn-on for me to be wearing some ladies panties at the next house party we go to or wearing the panties of a tenant, when I go to her place to do some repairs or maintenance. That is the thrill. Wearing another ladies undies while talking to them or being in their presence.
 
I am built like a linebacker so there is no way I would ever pass as a women. That said, I once had a lover who was very open to many things. I purchased a teddy set with garter and stockings, changed into it so it was on under my clothes when I got to her house. As she undressed me she realized and completely took control of the situation. She put me in the bed and began putting lipstick on me and started caressing me. It was a very erotic event and she used her hands, mouth and tongue in the most expert way. We did have intercourse, but before I could come, she stopped and used her mouth to finish me off. It was an amazing experience.
 
Flyingsgt said:
I am built like a linebacker so there is no way I would ever pass as a women. That said, I once had a lover who was very open to many things. I purchased a teddy set with garter and stockings, changed into it so it was on under my clothes when I got to her house. As she undressed me she realized and completely took control of the situation. She put me in the bed and began putting lipstick on me and started caressing me. It was a very erotic event and she used her hands, mouth and tongue in the most expert way. We did have intercourse, but before I could come, she stopped and used her mouth to finish me off. It was an amazing experience.
Click to expand...
She just had to finish by licking your clit…
 
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