Most Daring Thing You Have Done Crossdressed?

[Guest virginiaJ]

The scariest thing I have ever done was went swimming in the apartment swimming pool after closing. It was around 2 AM and I had already been out in full dress (wig, breast forms, high heels, everything) driving to the lake and hanging out there, and just wasnt done enjoying my time. So when I got back home I got my 1-piece nothing special about it black bathing suit and then threw on some capris and tank top to walk to the pool in. I was feeling quite vulnerable as I reached the deep-end of the pool and saw a guy standing outside his door smoking. Trying not to overreact and draw too much attention to myself I slowly made my way to the shallow end of the pool and got out like I never saw him. By the time I started getting my clothes back on he had already gone back in. So I decided to squash the butterflies and spend a few more minutes with the pool all to myself. By the time I got home I was completely exhausted. That has so far been the most exhilarating and freeing night of my life. I was working on my car a couple days later and that same guy saw me as he was taking trash out and started talking to me about whatever. Honestly I would be surprised if he could tell whether I was a guy or girl in the pool I mean I was deep enough that my wig was floating in the water just like any other girls hair would. I have done many other things and just get braver everytime things go well. Next on the agenda is for the wife and I to go to the local drive-in

theatre. wish me luck

Best Wishes,

Virginia

[Guest rachel38]

I kinda lied when I said I have never went out. I live in a rural area I can go out in the yard and miles of trails without seeing anyone. Well one day while doing some yard work I decided to take my mortocycle for spin around the yard. Its a real big yard. It felt so good I put on my helmet its a fullface no one could see who I was. I had tight jeans & form fitting shirt on.Must have passed as woman bicker with big breasts cause I pased a few guys and got a thumbs up guys useally just give a quick wave when passing. It really felt good but have never had the nerve to do it again.

[Guest seattle-cd]

War stories in femme underclothing...what a drag...

I've had this strong urge to go to the beach with painted toenails but since this isn't Key West...

I think we need some Emergency Room stories here.....I know there out there...

The weirdest thing I can contribute is physicals with a smooth bod.... (((yawn)))

Yeah, going to the gym and having no body hair, I feel really self conscious. But that's just not on the same level as these stories.

And I haven't gone out totally solo, either. I call a taxi or a friend and wait in the doorway.

[Guest Willow35]

Nothing fancy here, but the first time I've gone outside and shopped. Nice padded bra with matching hipsters(underdressed), white t-shirt, jeans and a hoodie to hide a little the otherwise obivous B-cup bra. I also had a rather nice shade of grey/brown nail vanish.

One or two people seemed to notice, however no one wanted to say anything.

[Guest cdallison36]

One of my first times going out dressed was a trip to Wal-Mart. I went out in the middle of the night in my black mini, pantyhose, sweater, and six inch heels. As I was walking through the grocery section I ran into a worker and I was really nervous but he just turned to me and said good morning ma'am and if there were anything he could help me find. As I was getting ready to leave the worker stopped me and asked if I would like to have a cup of coffee with him when he got off of work.

I agreed and it turned out that he was a crossdresser too and we became good "girl-firends"

[Guest Allie Bye]

that's awesome Allison!

the most daring thing was telling my guy friend. I told him that I'm a CD and how would he feel if he saw me dressed up. unfortunately it was uneventful. he didn't care and said "people are people with their fetishes"

arrrgghhh, but it wasn't a fetish! damn you, at least pretend you are shocked! dammit.

[Guest MsGsptlsnz]

arrrgghhh, but it wasn't a fetish! damn you, at least pretend you are shocked! dammit.

Shocked isn't a good thing... My wife is still in shock a week after telling her.

[Guest Guest_]

The most daring thing Ive done while dressed was go threw the drive up window at McDonalds. I was wearing a white satin blouse and had a black lace bra on under it. I had the blouse unbuttoned just enough to were you could see some of the lace on the bra. I was also wearing a black mini skirt with white lace stockings. A pair of dangling earings along with other jewelery and my wig. From there I went to my first Victoria Secerets store. Changed the mini for a pair of pants, lost the danglies for a pair of diamond studs plus the wig. I had on a pair of 3 inch sling back heals. When I first went in the sales lady asked if I needed any Help. I asked about their policy on trying on bras and she said that she would help me anyway she could. Was there for almost two hours, and had the most wonderful time. Bought a complete matching set which consisted of a bra, panties, carter belt, and silk nylons. I wore it out of the store. The lady who helped me was so understanding, and she even complmented me on my clothes. What a wonderful feeling. Love Amber L.

[Guest crissy_oakley]

I went with a friend to visit her husband in a Texas State Penitentiary Work Farm, while dressed...

[Guest Roberta-Belinda]

Rang a ladieswear store and asked if their skirts sizes went up to a size 16 in a girly voice. I must have been convincing because I was given great advice didnt seem suspicious. Wouldnt have courage to do it now though.

[Guest FranLee]

Hi I'm new on here but this thread intriged me. The most daring for me could have been one of several adventures over the years. I have to say that the most daring though is back when I was a younger LEO and worked in a setting with perimeter guard towers. I would be in total isolation for hours during the work shift unless something happened and then I had to respond. Instead of using a state vehicle I would use my personal vehicle and that was good for the state because of a lack of cars and good for me and the others assigned these duties because we had access to our personal property during the shift. Thus you guessed it I would bring my fem attire up in the secured tower with me and change and do a little lite-makeover and work in this state for 4 to 6 hours at the time. Never came close to getting caught and could change and clean up in a time that rivaled the Bat-pole. It was somewhat risky but in such a boring position it helped to pass the time and keep me alert for every little sound or movement. And when saide change into fem attire I mean shoes and jewelry too. Smoked back then and with a little caution I would step out on the catwalk and smoke while maintaining survaliance.