I Got Caught Cross-dressing

Personal Stories, Advice, and Support 273 People

    This has been an interesting week.

    My wife has been out of the city since monday, and I haven't been able to stop since then. I have worn 6 different outfits during this week and I wish I didn't have to stop. In the past few days I've been slowly venturing out to the street in front of my house wearing women's...
    deleted deleted
    3 Responses Sep 26, 2014

    I was caught in tx while driving

    when I was pulled over by the state police he made me get out of my truck to talk to him then made me stand on the side of the road so he could look through my truck. at the time I was in a skirt and blouse with hose and heels it was kind of exciting and scary at the same time
    deleted deleted
    5 Responses Jun 13, 2014

    There are times when the urge to cross-dress is

    overwhelming. I feel like I will explode if I don't get the opportunity. The opportunity arose a couple of weeks ago, and I was able to dress up from head to toe. As usual, my wife was accommodating, but didn't want to go out with me. Shopping for new outfits was on the list...
    SweetRhonda SweetRhonda
    51-55, T
    4 Responses Apr 18, 2014

    I was four or five years old

    and I don't remember why but I would sneak my Mom's panties out of the dirty clothes and wear them. They were way to big to fit right but I liked them and would wear them under my clothes. Since they were so big they would peak over the top of my shorts and that how my Mom...
    Jena1976 Jena1976
    41-45, T
    1 Response Jan 1, 2016

    I was caught fully dressed in bra panties

    garterbelt and stockings. I fell asleep on the couch dressed up and my roommate walks in the front door with 5 of his friends, 2guys and 3 women and when I woke up everyone saw me I was so embarrassed because I know all of them. So to this day I lush when I see them.
    brapantie brapantie
    46-50, M
    1 Response Oct 12, 2014

    I was in 14 when I was caught .

    See I lived with six sisters and my mum (only boy I'm house) not precisely when my oldest sister chanade was looking after me she would dress in feminine clothes and this one time I asked to wear her red dress and she put it on and did my make up I had big red lips to match my...
    Channybearxoxox Channybearxoxox
    22-25, F
    Mar 15, 2014

    I love crossdessing. I do it

    when my wife is at work. So one day I decided to see how feminine I could look if I went the whole way with a wig, makeup, earrings, fake nails and an outfit and heels. I put on a bra and boobs, a nice black top, red miniskirt, black tights and red pumps, did my makeup as best...
    kirbiegirl47 kirbiegirl47
    46-50, T
    Dec 31, 2015

    Yesterday, my niece called me to let me know

    she was going to the bar she first saw me dressed up as a woman. It is ladies' night on Wednesdays at this bar. She invited me, as she always does. As I was off early, I graciously accepted and hurried home to change. It took me a couple of hours to get ready, and I...
    SweetRhonda SweetRhonda
    51-55, T
    4 Responses Sep 11, 2014

    I was 19 and found a job in a small office (5

    people with me and 2 worked outside). I'd been practising my female voice by going on an adult chat line and posing as a female for sex chats with males. I really enjoyed it and most of those I chatted with told me it was the best they'd ever experienced. I was able to forward...
    amandatrane1 amandatrane1
    51-55, T
    1 Response Oct 3, 2015

    I got caught by an ex girlfriend once,

    she was at work and I didnt hear her come back. She walked in and I was dressed in a turquoise top with a flowery skirt and a pair of her heels. She was so angry and she yanked the skirt off so I was stood in just the top and a pair of her knickers. I will be honest it was a...
    deleted deleted
    4 Responses Mar 16, 2015

    This isn't so much about getting caught dressed,

    (I was but that story is in " I got caught Crossdressing"), so much as it's about the consequences. My ex mother in law was returning the key my ex had left with her and let herself in after I didn't answer her knock on the door to find me fully dressed and done up shortly after...
    amandatrane1 amandatrane1
    51-55, T
    1 Response Aug 1, 2015

    Happened about a year ago with my then

    girlfriend. We had a good thing going and she definitely had the looks that'll make you envious. But after a bit we both started working more and more and seeing less of each other. I would try and initiate something but it seemed to always end rather quickly. I'm sure it was...
    Emilyher1187 Emilyher1187
    26-30, T
    3 Responses Feb 27, 2015

    when I was 15 and had the house to myself I

    went into my sisters room and got my favorite bra and panty set with heels then got the hose I had bought got dressed in them. I had hidden one of my favorite dresses that she was giving away and laid it on my bed. went in to the wash room and put on some make up then the dress...
    deleted deleted
    4 Responses Jun 9, 2014
More Stories