I Crossdressing Punishment

Personal Stories, Advice, and Support 339 People

    After being introduced to her hairdresser,

    I was handed purple panties and told I had earned the right to wear them.
    donn2 donn2
    61-65, M
    8 Responses Dec 15, 2014

    The first time I had to crossdress in front of

    my wife it was punishment or a bet lost. We had just been married for less than a year and we got a little tipsy. We were goofing around playing a card game and I said to my wife loser has to do something that the winner wants. Well somehow I lost the bet and low and behold my...
    deleted deleted
    26-30
    3 Responses Oct 23, 2015

    My first time was forced on me

    when I was about 9 when we were living in Alaska. This is a vivid today as it was more than 40 years ago! I think I was in the second or third grade. The school had grades 1 through 8. The way the teachers kept the boys in line and behave was to threaten them with wearing a girl...
    patty1650 patty1650
    61-65, M
    9 Responses Feb 20, 2014

    Part 3 (Parts 1&2 posted earlier about

    experiences in Alaska.) My mom was an outstanding seamstress and rarely used patterns. She won many awards for her creations, including one for a dress made from the Sunday edition of the Houston Chronicle newspaper. She made most of my clothes - shirts, pants, suits, etc. and...
    patty1650 patty1650
    61-65, M
    1 Response May 27, 2014

    It's not a normal thing

    but one time I had to wear tights (pantyhose) and nothing else for a whole weekend at home
    SamSamson99 SamSamson99
    18-21, M
    1 Response Feb 24, 2016

    i want an indian women

    or girl who can forcefully dress me up as a bride. like make me wear saree, bangles, mehndi(henna), bindi, and all other accessories. i am ready to be their wife, gf or sissy. if any women or girl in dubai message me
    shifakhan shifakhan
    22-25, M
    1 Response Apr 12, 2014

    My Crossdressing-The Future

    In my opinion, crossdressing is similar to a drug addiction, in that it appears, (at least with me) that you need greater stimulation to keep yourself satisfied. I don’t know any other crossdressers personally, so I can’t say if this is universally true. My needs have changed...
    1SarahAnn 1SarahAnn
    51-55, M
    11 Responses Jun 13, 2013
    bendoverman75 bendoverman75
    41-45, M
    3 Responses Apr 2, 2014

    The next time was about a week later on a

    Friday. I got pushed by one of the school bullies into the water. I was totally soaked. Again, My teacher dressed me this time in a red and blue plaid dress with a white lace collar and white long sleeves and a little black belt, also a pair of red tights, the black Mary Janes...
    patty1650 patty1650
    61-65, M
    1 Response Feb 20, 2014

    as a CD----I've been Dreaming of men

    treating/talking to me like a ****---Date rapes & the like--Public humiliation like being out in public--them gropping& grabbing me lifting my dress ect ect--all the thing real women don't like/want---even so far as offering fem me(Jane) to their friends or even strangers& me...
    janedon1 janedon1
    61-65, T
    1 Response Dec 5, 2015
    nidhi9skirt nidhi9skirt
    31-35, M
    1 Response Oct 14, 2014

    Preface-My Crossdressing Story

    I am a crossdresser. I’m a guy that likes to wear women’s clothes. The very words are painful to say and hear. I’m embarrassed by this need, but I’m not going to hate myself because of it. It’s just the way it has always been since I was a young boy. I’m not 100...
    1SarahAnn 1SarahAnn
    51-55, M
    11 Responses Jun 14, 2013

    Find Crossdressing stories & Pictures www.

    TwistBox.inStory: NeerajaPart 1Part 2Part 3Part 4Story: Raj Turns RashmiPart 1Part2Story:Beauty ContestStory: Wife of ThomasStory: A walk in the ParkStory:My first Date Part1Story:My First Date part 2My StoryStory:Happy Being SisterStory:Birthday PartyLoved Being LathaStory...
    mounicacdcd mounicacdcd
    41-45, F
    May 5, 2015

    Yesterday I cried yesterday,

    not a hard satisfying cry, but small sobs, the kind that struggle to come out against your will. I didn’t think that I would cry, it caught me by surprise, but not as much as the violent shaking that shook my body as I talked. I even wrapped my feet around the chair legs, and...
    1SarahAnn 1SarahAnn
    51-55, M
    1 Response Feb 10, 2014

    I've been crossdressing

    for mabe 10yrs--Wife got me into it as part of our sexlife---we were swingers long before that--but her being a BIG woman it got so we ended up with few couples mainly just men who just want her--I found that I enjoyed that More than swinging with couples---I became her cuckhold...
    janedon1 janedon1
    61-65, T
    1 Response Dec 5, 2015

    My girlfriend made me to wear her panties

    as a part of punishment to college
    Suhanihotty Suhanihotty
    22-25, F
    3 Responses Jun 26, 2015

    My Crossdressing Life-The Present

    I met my wife seven years ago in late September on one of the large Internet dating sites. It was my last week on the site, as I had no real previous luck in meeting anyone that I thought would accept me into their lives. It was her first week on the site. So maybe it was fate...
    1SarahAnn 1SarahAnn
    51-55, M
    1 Response Jun 12, 2013
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