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Thread: Biggest risk you took to dress that you got away with?

  1. #26
    There's that smile! CarlaWestin's Avatar
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    Jan 2011
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    As I worked with a uniformed crew in a large facility, many days under my loose fitting uniform I would be enjoying full lingerie.
    There was an employee health fair in one of the ballrooms and folks were lined up barefoot to get their BMI checked. Not only was I wearing sheer stockings but,
    my toenails were painted beautifully red. I just waited for the right moment, faked a phone call and then left to address the imaginary concerne.
    I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
    My new maid's outfit is cute. Sure fits tight.
    And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
    Smile, Honey! You look fabulous!

  2. #27
    Junior Member Melanie Therese's Avatar
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    Feb 2013
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    I underdress at work most times I?m in the office except when a colleague from another site is visiting as there would be hugs involved. I work in a national team where I have known people for several years so are quite close.
    One time I was helping a colleague and resolved a major computer issue she was having and she said I need to hug you and she did. Not sure if she felt it but nothing said and no awkwardness at all.

  3. #28
    Silver Member Maria 60's Avatar
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    Sep 2010
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    When I was younger I think back now on how smart I thought I was but really so naive and took bigger chances then I thought.
    For some reason my mother stored my sisters wedding dress underlining in my room, it didn't have lace on it but it was long and silky. One night I woke up at around 2am and for whatever reason I decided to put it on and a pair of pantyhose. I would leave my room and go to the living room window and I would just stand there and let the street light shine in and I would just enjoy looking down at my pantyhosed feet and the shiny slip.
    I never thought if someone would have heard me got up to see who was walking in the house, I would have been totally caught because I would have had no were to run back to my room.
    Another time I went bike riding with my wife and don't ask me why I wanted to wear a bra on that hot summer day. There were a lot of people riding along us and I was usally riding behind my wife and at one point I went ahead of her. She stopped me and told me when I reach down for the handle bars my shirt tightens up and the bra is in full view. I'm sure there were a lot of people who rode behind me to see it. My wife was very upset that day but I thought it was a little thrill.

  4. #29
    Happy 2 B Here Mercedes's Avatar
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    Jul 2007
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    Very early in my relationship with my now spouse of 30+ years we were meeting each other at a friend's house for a party. I do not know why, but I decided that I wanted to wear one of her, I know, bad me, tight and lacy white teddy with lower snaps (thank goodness) under my clothes to the party. I also did not expect that we would be leaving at the same time, but as we arrived separately we had our own cars. I was panicked that when we got home how was I going to explain wearing the teddy and not be in big trouble. So as I was driving back I was trying to remove the teddy, again thanks to the snaps, I was somehow able to do that while driving and not crashing, talk about distracted driving.

    I was able to get home and get it back in the lingerie drawer and she never knew. Certainly not the smartest thing I have ever done.

    Mercedes XOXOXO

  5. #30
    Senior Member jjjjohanne's Avatar
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    Probably the biggest informational risks are when I told persons who knew me that I was a crossdresser. I have no actual control over what they did afterward.
    Biggest physical risk would be when I have been dressed and in public. The anxiety/stress/distraction of it all blinded me to my surroundings and I ran a red light on a couple of occasions. One time, someone pulled out in front of me on a multi-lane highway, and I reacted in time, but the car to my left hit the other car. I was dressed pretty and I was almost in a wreck.
    Beyond that, I have worn "invisible" women's clothing as a man in front of people who knew me. I went to a conference in a skirt, but the day before, a guy I knew was at the conference (when I was dressed in menswear). He was not there on day 2. I have run into one person from that conference since.
    I am a man who presents male and wears feminine clothes.
    I blog about my outings: https://joeypress.wordpress.com/

  6. #31
    Member Christina89's Avatar
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    Apr 2009
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    South Shore, Massachusetts
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    I one time was home from and semi-dressed as Christina. It was around dinner time and I went to go get something to eat and realized I didn?t have anything I wanted. So I decided to go to the store quickly and get something to eat. I also made the decision to just stay semi-dressed and threw on a sweater to cover the shirt and bra I had on. I ended up driving to a drive-thru and getting food from a fast food restaurant.

  7. #32
    Member elliemoss's Avatar
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    Dec 2011
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    I was I my early 20's and had some time off before the new year started in Uni so my brother asked if I could house sit and look after the dog for 2 weeks. I was happy and excited too, 2 weeks in an empty house and access to his wife's closet. The day came when they were packed and driving to the airport. They said goodbye and drove off. I was so impatient and excited in those days I went straight up stairs into their bedroom. I remember my knees wobbling with excitement going through my brothers wife's clothes. I picked out of lovely black Jersey maxi dress and slipped it on. Her shoes were too small but I had a pair of cute heels in my backpack so I put those on and put one of her grey cardigans on. I went downstairs feeling pretty Euphoric and put the kettle on. I sat at the kitchen table and pet the dog then.... to my horror I noticed the shadow of a car coming into the driveway through the perspex glass beside the front door. I jumped up, pulled the dress up and ran as fast as I possibly could (in heels) up the stairs. Halfway up I could hear the keys in the door. Instinct led me into the bathroom where I locked the door and started taking my heels off. My heart felt like it was going to pop out of my chest. I heard my brought run up the stairs, open the door of his bedroom, shuffle around then close the door and run back down stairs, out the door and into the car. As I heard the faint sound of the car drive away I almost fainted! The dress was also off me now, Phew!

    Another time a few years later I was living with 2 other housemates. We all worked 9-5 jobs in the city. I had a couple of days off. One morning I was feeling quite fem so I put a dress on with some flat saddles. I went downstairs made some breakfast and had a coffee. I must have been 30mins downstairs. I went upstairs and into my room. After about 10mins I hear my housemates door open and hear her walk to the bathroom. Yikes! Ends up she was feeling unwell and didn't make it into work.

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