Most Daring Thing You Have Done Crossdressed?

[Guest gailgirl9]

Although I am a bit overweight (If you can stand it, a corset from Fredericks can do wonders though!) , I pass really well. As a result, I have gotten pretty comfortable shopping in malls, and trying on outfits. I try to choose the stores where they don't have salespeople "guarding" the dressing rooms. A few weeks ago, I was able to dress for 36 hours straight . I was feeling confident on Sunday, and I went into a smaller, more specialty store. I told the salesgirl that I had an important date with a guy who I was hoping would ask me out. She recommended a number of dresses, and evaluated me in each as I came out into the open triple mirror area, commenting on how each dress flattered me or not. One of the other customers even commented on a couple of the dresses. What a thrill!

I didn't actually buy a dress (didn't really have the date ), but I had so much fun. I have no idea whether I was "read"- if I was, they didn't show any sign of it.

[Guest Sarah Miller]

Well I have now done the most daring thing for me whilst cross dressed. I went out in public for the first time the other night. It was with a large group of Cders on a harbour cruise and dinner at night. I was terrified walking with my friend to the car in the hotel basement, leaving the car, and standing on the wharf waiting for the boat being stared at by guys fishing.

Wouldn't have traded any of it away though. I can not wait until I can go out as a beautiful women again.

xxo Sarah

[Guest Annalee]

My sister took me shopping, geheesh what a rush!! and yes, I used the dressing room trying on all sorts of outfits, one piece bikini's and you know what? the ladies didn't seem to mind at all, I walked around wearing panties, matching bra and two inch heels, I was so nervous!! but got kinda relaxed when I noticed that's what most of the women were wearing...

[Guest Amanda Whyte]

I dont consider myself a crossdresser, but the most daring thing I have done is:

I was living with a friend and his wife, they had no kids or anything and needed the help with expenses. One time they went out of town and I snuck in and dressed entirely in her clothes. I am kind of ashamed in doing it now since I didnt have her permission. Well I was just sitting around the house, when I got the urge to go out. My bravery only went so far though because I put on a rain coat over the clothes. It was the most excilerating and free thing I have ever done.

[Guest *Charlotte P*]

Walked to the mailbox.. sadly enough

[Guest Madison_Always]

The first time i went in front of my therapist. I was literally so nervous I was about to cry. It went fine though, but oh my goodness was that scary lol.

[Guest StephanyR]

Well two weeks ago my wife and I went to Zellers. Canadian store. I always wear nylons and panties when we go out and even a bra. So there we were in the shoe isle and I was looking at some shoes. Of course my toe nails are painted pinkish and the nylons were beige. well I was trying on these high heels and showing them to my wife and she said turn around... I did and just then two girls walked right around the corner and saw me. They just smiled and walked on and smirked.

[Guest StephanyR]

The next thing I know the two girls stopped and said very nice goes well with the jeans!!!! I was scared and excited at the same time. My wife looks at me and said he even did an great job on his toe nails!!! The girls wanted to see so I showed them. They were impressed and said I should try some of the womens clothes that would match the shoes. Gawd the scaredness went away and the shock of walking thru the ladies clothes with the heels on!! I said I would look at the clothes and carry the heels to the change room. I couldn't believe how accepting they were.

[MaryEllen]

Way too cool! I'm glad it was such a pleasant experience for you. I'm sure there will be many more.

MaryEllen

[Guest StephanyR]

I hope not it was nerve racking!!! I was almost caught one other time and that really put a scare into me. I like the idea of almost being caught or even let people wonder but when you either get caught or seconds away from being caught it really gets your heart going!!!!

[Guest kimberly c]

Hi Girls, I went out to my favorite lingerie store today fully dressed, when I got out of the car there were about six guys

standing around. Picture me with girls jeans, feminine top multi color pinks, breast forms, feminine sweater. necklace

and high heeled boots. Not even really a stare, just walked to the lingerie store. In the store the sales lady helped

me with new breast forms and I also tried on about six different nightgowns. I tried on a purple full length gown in the

changing room, the sales lady says come out and look in the full length mirror as I did two more ladies had entered

the store, they weren`t even shocked, both said how pretty! Caught but okay!

Love Kim

[Guest rikkicd64]

I go out almost every where dressed, my experiences have been great so far, at the grocery store the last two times ,the young men sacking have even addressed me as "maam",it is wonderful. The ladies in the lingerie shop were extremely helpful and they both knew I was a man dressed as a woman, I hope everyone is able to have as good of experiences that I have had.

Rikki.....

[Guest praxis]

Thinking about StephanyR 's comment on moments that get your heart going. Most daring thing I've done is wear a bra under my sweatshirt a few years ago in the Marines. Problem is I didn't give enough thought to how subtle it would show. Marines are a tough bunch and we tended to give each other cold stares in the hallways. There were a few folks I passed though, I wonder. After a couple hours I had to change...pretty scary for me... Might be a little less dangerous now with 'don't ask don't tell' abolished.

[Guest Hollie W]

I love reading how well people treat us when in shops and on the street. This is going to help me when I am divorced and will be exploring my darker side further. Thank you all for sharing.

[Guest Just_Amy]

im not sure/...just go outside O_o

[Guest Kristi Lyn]

My only stories include a night that was extremely cold and I had to work. My under armour leggings were torn up from a fight the night before. So my ex offered up a pair of her black tights to help keep me warm through the night. So after getting into my Deputies uniform I went to work in tights for the night. Arrested 5 men that night and my every thought was if they only knew I was wearing tights. The other story was just a few years ago when I started my RLE I was dressing daily but had to go to a job interview. Wore a bra, panties, and pantyhose underneath. Went through the interview and noticed the guy was staring at my crotch. Didn't think anything of until getting in the car and noticing my pant had a huge hole in them at the crotch. Least to say I didn't get the job but he got an eyefull. LOL!!!

[Guest deglerious]

Sadly, I've never been out in public, so to speak, where anyone was likely to see me, although I've walked in the deep woods before while wearing a skirt with a turtleneck and jacket as well as four inch high heeled boots. Underneath was a 38J bra (with my own form,) hipster panties, a garter belt and stockings. I've probably gone as far as a mile away from where I changed.

[Guest noah100121]

well im 13 so its not that good but i wore bright red panties under my gym clothes in PE and tennis class.

[Guest Jamie Lynn Star]

Hey! I live in a small town -main street closes at 1 am - i usally go out dressed in jeans and top boots or tennis shoes-comfy- at times its a dress and heels. One night I was really pretty wearing a dress white sttrappy heels and black hose. As I was heading home bout 3blocks to go I saw a car light behind me. as it got close I saw it was a police car I got a lil scared but walked normally when it got closer it slowed down I heard this woman say" Hey were you going?" As she pulled up and stoped I said "on my way home few blocks " She said "justt checking" and went on her way. I was so relieved that I wasnt taken to jail.. Ive been out more since . I thinik she knew me and not really worried about me being out. cause I havent been stopped since. JLS

[Guest baily]

I remeber when I was still in high school and my mom said I could take the care down to the gas station the night before we were going to go out of town. So we wouldn't have to worry about it in the morning. So I put on some drk brwn pantyhose and put them on a pair of sweats and a white hooded sweat shirt. Put a pair of heels in my back pack and a pair of high cut jean shorts. I went out to the car and got in and as I was driving I was so excited to be out in pantyhose. So I pulled into a parking lot that was vacant and pulled out my daisy dukes and black high heels. And took off my sweats. and put on my daisy dukes and black heels. I couldn't believe how sexy I felt and how good the wind felt on my nyloned covered legs. I got back into the car and drove to the gas station feeling a nervous but exciting feeling as cars passing by thinking what if they could see me wearing pantyhose and heels. As I got to the gas station there was nobody there. So I pulled my hood up so you couldn't see my face and got out. I felt so nervous but so excited and went and started to fill the car up with gas. A old couple pulled up and an elderly man got out and was looking at my legs as he was going to get some gas. As I was done. So was the elderly man who went in before me. I went in and grabbed a soda and went to the counter. The clerk didn't even notice me as he was to busy checking out the tv behind the counter. I payed for my gas. As I was leaving I said thanks and was walking out the front. I loved the way my heels sounded on the pavement and the swooshing sound of my pantyhose legs as they would rub together. As I got to the car I opened up the back door on the driver side and looked back and noticed that the clerk was looking at me. I smiled and closed the back door and climbed in the driver seat and drove back home. As I pulled in I changed before I went into the house and went up into my room and was just so excited about my out and about experience. That was one of my daring moments. Tho not as daring as wearing panties and bra in a combat zone. Which is a who new level of daring if you ask me. Very hard if at all topable.

[gennee]

I didn't do anything daring. I just wanted to dress and go out, so I did.

[Guest amanda_s]

WOW Donnajean what colour were they, i don't think anyone can beat you. grade 12 last coulpe of weeks of school wore a bra and panties to school it was 1986 toronto. still don't know why i did it.

amanda

[Guest Marlane]

I used to be in a band and one night I decided to dress en femme. I went to the local thrift store and bought everything I needed and some things just for my own enjoyment.

I found a black leather skirt that fit and multicolored sleeveless turtleneck. I stuffed my bra with tissues and bought a pair of fishnet pantyhose at a local store. I got my makeup done at a local department store and had my longish hair styled. I went to venue by myself and had a little bit of trouble getting in the stage door even with my stage pass. Any way, That night I performed before 1500 people dressed pretty much how I always wanted to. My bandmates thought it was great. But it was the 80"s, What can i say......Girls Just Wanna Have Fun!

[Guest shaver]

That was a hoot and no I can't top it.

[Guest Melissa~]

I went on a back country elk hunt, 12 miles of horse riding from the road, partially CD'ed with painted nails. This was a paid wilderness expedition, week long, no one said a thing even about my painted nails. The hunt was a success.

That was last fall, moving further forward this year.

By the time I return there I am likely to have transitioned. I doubt that's a barrier.