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Thread: The most Dareing thing you have done!

  1. #1
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    The most Dareing thing you have done!

    What is the most daring thing you have done while crossdressed?
    `I had a trip onetime of 1000 miles and got dressed but without a wig or makup and got in the car and left. I made it over 700 miles before I had to change back. I got gas twice and went through the drive through ad McDonalds. And yes they looked out the window and laughed but I was 400 miles from home and even if they wanted to tell they didn't know who to tell

  2. #2
    Lovely in Lace (or Rope)
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    I thought I had a good one, but doesnt come close. Nice job you two LOL

    Amber

  3. #3
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    mine isnt too great, but it was my shopping trip

    i went to this supermarket, they were having this offer for bras, went to the section, picked three out, and paid up. my heart was thumping like crazy...

    i now learn to ask for assistance

  4. #4
    Senior Member Lawren's Avatar
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    I used to deliver oranges to processing plants and packing houses in Fla. A lot of the work is done at night and my truck had a sleeper so I would carry my girl clothes and make the night runs dressed up. I even took a nightie to sleep in.

  5. #5
    lycra lover crispy's Avatar
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    Drove 200 miles on a Sunday evening. Stopped to fill up with petrol and went to the toilet. Changed into a full length nighty under my boy clothes. Drove a mile down the road and took off my boy clothes. Drove in a dream for 3 hours wearing just the nighty, dreading but enjoying the thrill when I passed a truck or a bus and could be overlooked. Heart thumping at every set of stop lights. When I got to the other end it was after midnight, so I just walked from my car parked on the street to my front door dressed in the nighty. Loved the adrenaline thrill. Is that why we do it?
    [SIZE=3]crispy[/SIZE]
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  6. #6
    Kathy B
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    Smile To get dressed as a female for halloween

    The most daring thing I did was to have my ex girlfriend dress me as a female for halloween.I was dressed wearing a bra,panties,nylons, a wig, full make up, high heels, and a flowered dress. It was the most exiting time of my life!Actually thats how I picked my name cause Kathy was my ex girlfriend.

  7. #7
    cherry_cn
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    Wondering in crossdressing

    I went out one night with all crossdressing.
    I dressed pants,bra,wig and a beautiful skirt(more like a nighty),then went out from my house and went throught streets and streets.
    (Sorry about my poor English,But I really love crossdressing.The photo under my name is my real picture after crossdressing)

  8. #8
    Aspiring Member
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    well I do not have to much like that. But the few times I did dress was in a large hotel in chicago and I dressed for a masqurade show that was going on at a scifi con. When during one of the times i was dressed and went down stairs to go to the waiting room for the show this other guy in the elevator asked me why i was dressed like that in my costume which was a cheer leader coustume so I told him i was going to a masqurade and then he just kind of looked at me and i just kind of ignored him after that it was really none of his busniess that i was dressed as a girl. But it was kind of fun and exciting as i now recall just being able to be dressed female was kind of a real thrill. There were a few other times as well with other coutumes. Just being able to finally be a girl for awhile was really great You have to have gone there to really understand!. To me it was just more then the coustume!.

  9. #9
    joannablake
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    I have two things that I considered the most thrilling things I have done dressed.
    1) Was my very first time out I went to a Mall down in Portland Oregon fully dressed and walked into all the most feminine shops and asked them to assist me in finding some new outfits.

    2) I drove from Tacoma Washington all the way to Sacramento California in full dress I dont think the cop knew what to do when I was pulled over in Yreka California for a burnt out taillight.

    Love Always
    Joanna

  10. #10
    The Girl Next Door windycissy's Avatar
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    My most thrilling adventure was a few years back. I had a business trip to Washington with a one day side trip to New York in the middle of the week. I flew to NY with my girl stuff in one suitcase and my guy stuff in another, checked into a hotel, took care of business, and transformed myself into Windy. It was autumn in New York, and I found a great trenchcoat on sale which was perfect for traveling. Without quite believing I was doing it, I called Penn Station and reserved a seat on the Metroliner back to Washington - as a girl!

    I was a nervous wreck as I checked out of my hotel with both suitcases and caught a taxi to the station. This was pre-9/11, so I was able to pick up my ticket without showing an ID and next thing I knew I was sitting next to a businessman on the Metroliner. Fortunately, he kept his nose buried in his briefcase.

    I remember it like it was yesterday: I was wearing a knee length red foulard dress, a matching bow to pin back my hair, black heels, sheer hose, and of course my new trenchcoat. At one point the conductor referred to me as "Mrs" thinking I was the wife of the guy sitting next to me, and I smiled shyly as I shook my head. All too soon we were in Union Station in Washington, and I tugged my suitcases on the subway back to my hotel in Wardman Park. It's not easy carrying two suitcases in high heels!

    A moment of truth when I put my key in the door of my hotel room after being gone for almost two days: the door opened, and my adventure was over. Ask Windy

  11. #11
    Member Glenda's Avatar
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    I'm not sure which time I would include in this thread. For all of you who have posted thus far, I would say yes, yes, oh my, yes, wow, me too, OMG, etc. They are all brave moments and you should all feel so proud. What a rush! And walking by my boss might be more than just a little bit scary.

  12. #12
    Member NewShy21NJmtf's Avatar
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    Wink I've written about them b4

    Don't really feel like digging up the links to the threads about this, but my finest moments are getting a make-over in Victoria's Secret in boy clothes and trying on bras and getting measured in the same store on a different day, also in boy clothes. Loved reading the stories.

    Stephanie

  13. #13
    CD Lifer and a Visual Kei Shinya's Avatar
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    Post I couldn't say

    I couldn't say on the board, but it did have something to do with the ex-wife. Thats all the farther this story goes.

  14. #14
    Vallari (Goddess) ;)
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    I wore a bra and panties and womens deodorant under my guy duds to a new years eve party in downtown Austin for the year 2000. I walked around the streets and went in and out of stores/bars and was around (probably)thousands of people. I know it isn't much compared to the other stories, but it was a thrill. Thinking about driving around dressed one of these days!

  15. #15
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    Crispy, Cherry...like the pics i luv asian girls.
    im gonna try something a little daring more next wk

  16. #16
    michelle ca
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    Wink The Best I have done

    I got dressed in panties,bra,slacks & highheels
    Then I went to the hairdresser to have my hair & make/up done
    Oh what a great feeling

  17. #17
    michelle ca
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    not sure how to recieve messages or chat

  18. #18
    becky1
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    Wow!, some great stories.

    I went out once dressed in this awful outfit. It was really late and i was driving a landrover lol, so i had to put on some sensible shoes.
    I went to the petrol staion near me with the aim of getting out and looking all sexy whilst leaning over at the pump! and then clipping my way up to the counter in my heels (took them with me) and paying . For some reason i had the notion that the tired assistant might fancy me and compliment me on my prevocative looks.

    As it happens, i got as far as the petrol station when i saw a police car and bottled it to drive back home with my heart pounding and the hump!

  19. #19
    Vallari (Goddess) ;)
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    Talking My first time dressed out on the town!

    I took a drive recently on Saturday night (9-4-2004) to several places around Austin, TX while dressed! I wore a black bra top, short brown denim skirt, little black thong, earrings and necklace, black heels, and bracelet. I drove around my neighborhood, the freeways, and downtown. It was late at night, but people were still out for the most part - especially downtown! Its tricky learning to drive in heels - thank god most of the roads were vacant! My short skirt was a mistake! Even when I walked too quickly it felt like my bare butt hung out of that skirt! I pulled up next to a taxi cab at an intersection and noticed the passenger in the cabs front seat glancing at me, after looking away quickly (and smiling to myself!) and looking back, the cab driver was glancing at me too! This went on for a few more secs until the light changed; what a thrill to have others see u dressed for the first time in public! I then went by my old high school, which I graduated from only months ago, walked across the parking lot, threw out some trash, and returned to my car. Nobody was there, but cars drove by on the street - very exciting feeling! I then stopped near an old friends house - a girl that I used to be friends with but then we didnt like eachother anymore. I went to my trunk, and put my male duds in the back seat, and went home. Not sure why I added this stop to my itinnerary And that concluded the trip for tonight!

  20. #20
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    daring thing that i have done

    I had this lady friend and asked her if she would dress me up as I made out that i was going to a fancy dress party (obviously not), well she said yes so after gathering all my clothes i decided to go around and when I got there she told me to go up to the back bedroom and get undressed and put my dressing gown on.
    The only problem I had was I had forgotten my panties and cheekily asked if I could borrow an old pair of hers and she said yes.
    after doing all my suspenders and the zip on my dress i asked if i could walk around her house for a while, so after about 10 minutes i heard the front door opening and could see it was an elderly woman (her mum) and so my only exit was to go into the back garden when her dog started to bark at me but luckily there was a shed and her mum had asked what is the dog barking at.
    wow what a lucky escape but i had to wait about 35 minutes and was bursting to go to the loo. LOL

  21. #21
    Tristen Cox
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    As for my so-called 'most daring thing', the first choice would be dressing up at work and almost being caught.
    A few years ago I worked in a bodyshop with a bunch of rednecks and did side work after hours on site. Went in one afternoon and dressed from the neck down minus make-up.
    Well all was fine and I was cleaning and putting tools away when the fence jingled letting me know someone was approaching. Looking around the corner my heart stopped, the painter had shown up to do his side work giving me only a minute to switch back before he saw me! It was scary to think what would have happened if he had seen me and told the boss, however I am a very fast dresser when it's an emergency.
    I have gotten dressed up complete, with my own hair (beyond the shoulders) and taken many drives. One occasion lasted three hours, covering my whole county. My car is very easy to recognize by my friends so I tried to avoid some areas on my cruise. Stopping at busy intersections I felt as if they were all staring at me. Maybe they were, but I was so excited to be out that it didn't matter. Like many of you out there I love the rush!

  22. #22
    Junior Member
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    well I just wanted to share my story of what I did a while ago, I got home from work about 2 am and decided to dress up as always.. well I took a shower and when I got out i put on my purple n white ( girls rock ) string bikinis , with my 38b purple n pink Bra ( stuffed with socks )and a pair of baby blue ( joe boxer ) anklet socks , then my Mudd low rise jeans ( w/ pink plaid belt ) and a baby blue long sleeved top , and my light blue an white womens Nike running shoes . at first I was just gonna stay home and chat but I decided to go for a ride instead.. I started out I was gonna just stay in town but I decided to drive 50 miles to another Bigger town .

    well I left my apartment fully dressed ( wore a boys sweatshirt over top just in case ) till I got out of town and that came off for the rest of the night. well I drove the 50 miles and when i got there decided that I needed Gas in my blazer and was thirsty so i stopped at this 24 hr gas station , I pulled up to the pump and just sat there , I figured id chicken out and where the sweatshirt ( I didnt bring any boy clothes other than that ) but I didnt I looked around and got out and started to pump my gas .. I was going to pay right at the pump but I decided to go in.

    I was so scared someone would see me , it wouldnt have been so bad if I had thought ahead and shaved off all my facial hair ( i looked pretty freaky in all girls clothes with a beard ( owell ) but I was standing there pumping my gas and a few cars and a tractor trailer went by , the driver of the truck looked at my ass i think. it felt so good to be standing there dressed like a teenage girl I loved it soo much. well the time came to pay for my gas and get a soda , I almost put the shirt back on but didnt.. My heart was racing soo fast when I walked through the parking lot .. inside there was a boy and a older woman , the boy was mopping the floors when i walked in so he didnt notice.

    I went and got my soda and walked up to pay for my gas , no one else was in the store but us 3 , the boy stopped mopping and rang me up .. he didnt say anything really or look out of the ordinary at me . there i was in the middle of this store dressed in all girls clothes , my Butt looked really good in my mudd jeans and my boobs looked just as good , the only bad part is I looked like the beared lady ( LMAO ) o well .. when i walked out i realized that when I am dressed as a woman I tend to walk like one as well , i just wish I could dress this way daily I was soooo comfortable other than I was scared someone would see me that I knew but it was 4am and 50 miles away so I took the chance..

    after that I drove the 50 miles home and never put the boy shirt back on at all , drove right through main st of my town dressed as a female and I didnt care who seen me , I prob would have if I thought about it but I was in heaven, I finnally lived out my fantasy . next step is shaving all my body hair , painting my nails , getting a wig and then doing the same thing again

  23. #23
    New Member Christine1960's Avatar
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    Talking Hurricane winds on my pantyhose legs

    This past Sunday as hurricane Francis was approaching the west cost of Florida, I went and got a Sunday newspaper wearing short shorts and pantyhose. I wanted to really feel the wind blowing against my pantyhose legs. It felt great walking around our complex getting a morning paper as the storm had not yet approached.

    Hugs to all,
    Christine

  24. #24
    Member Jocee's Avatar
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    I drove from Boston to Atlanta and back..... for Southern Comfort.... 10 days of no boy clothing at all and I didn't bring any with me....

    It was initially thrilling -- checking into motels, eating, tolls, pit stops -- but the drive back it was sheer bordom...... hour after hour of driving....

    Joanna

  25. #25
    sharonlim
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    Last edited by sharonlim; 09-07-2004 at 04:24 PM.

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