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I Started Crossdressing

Personal Stories, Advice, and Support 123 People

    Started Crossdressing A Long Time Ago

    I started crossdressing, wearing panties, pantyhose and lingerie a long time ago. First it started with panties, seeing my sisters panties on the bathroom floor after the showered I could not resist picking them up and feeling them and all of the sudden before I knew it I had...
    pantiescouple pantiescouple 26-30 Mar 5, 2013

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    My First Crossdressing Experience

    When I was about  5 years old, playing round at my aunties house, I accidently wet myself. When I told her what I had done she said don't worry and told me to get undressed.I was then bathed and dried.She the told me the only clothes she had that would fit were my...
    Claire1965 Claire1965 41-45 5 Responses Dec 2, 2010

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    Getting Started

    Just got started need advise
    nfordhaas nfordhaas 41-45 Oct 7, 2012

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    Started?

    Not 100% sure what got me started crossdressing and when it was.I remember as a kid I would look through the Christmas catalogs that would be laying around just before Christmas. When people were around I would be looking through the toy section, and if no one was around I would...
    happilymarriedguy happilymarriedguy 51-55, M Nov 25, 2012

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    Born in the 60s, the world around me was a

    wonderful place. I distinctly remember at a very early age sitting in the same room as my mother and her sisters would be carrying on in conversation and think nothing of lifting their skirts, adjusting their garters, and smoothing out their tucked in blouses. I found all the...
    AndiTV AndiTV 51-55 4 Responses Aug 10

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    Last night i confessed to my mom

    that i want to try crossdressing and painting my nails and this morning she bought $100 dollars worth of womens cloths online. Im so glad I confessed to my mom, im going to own my first pair of heels and dress in a week :D Thank you people who replied to my last post.
    Poopoohead17 Poopoohead17 18-21, M 1 Response May 17

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    Related Experiences

    When I was 14 I started crossdressing. My Mother and older Sister were gone quite a bit. One day after school I went home and started putting on my sisters clothes. Bra, panties...
    Stephaniegirl226 Stephaniegirl226 36-40, M 5 Responses 6 days ago

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    I was Caught Crossdressing by my next door nebor Guy and Im still doing it to day. I was in my Wifes We are the same size too. Well I was in her 34-C push up Bra, and Bikini...
    Kellyboy541 Kellyboy541 56-60, F 6 Responses Aug 21

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    Yesterday started out like most days. I get up in the morning and take a number of my nightgowns, negligee sets out of my closet and put each one on until I find the one I want to...
    silkydrawers silkydrawers 46-50 4 Responses Aug 20

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    I was alone that day got bored at home I was watching from window on road one girl was walking I saw her in salwar she was so feminine there was no one on road suddenly she makes...
    sronal sronal 22-25, F Sep 9

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    I love crossdressing the feel of a sexy bra and thong are the best and sexy mini skirt
    harley80cu harley80cu 41-45, M 2 Responses Sep 11

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    One of those fascinating but as yet unanswerable nature versus nurture conundrums. What is interesting is that for some the crossdressing impulse expresses itself very early...
    Barrbara Barrbara 56-60 2 Responses 3 days ago

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    anyone looking for friends to chat about crossdressing, etc. please feel free to add me.
    girlyAndrea1987 girlyAndrea1987 26-30, M 1 Response 3 days ago

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    The last time..? Maybe? So it's been a while since my last post (December) and I was thinking about coming out. Well, things took a hold of itself in it's own way and so much has...
    elliecarr elliecarr 18-21, T 8 Responses Aug 22

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    I have always wanted to get caught cross-dressing and be horribly humiliated. This story you are now reading is not true, but I am sharing it as if it was true: Last Friday night...
    Robertredlips Robertredlips 56-60, M 1 Response Aug 27

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    I started collage again yesterday and wore me pretty green panties and a lot of people saw and this guy was cute told me to follow him so i did and we dressed up toghter and i tide...
    LOVERPANTIES LOVERPANTIES 18-21, M 6 Responses Aug 29

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    Started with my 3rd cousin who lives in Germany. We would skype and talk. He asked if I was curious I said that I'm gay. So he then undid his pants and started stroking. He told me...
    GayJohn98 GayJohn98 18-21, M 1 Response Aug 28

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    I started around 7 or 8 years old. I heard my parents having sex, though I didn´t know what they were doing at the time and I felt a little tingling between my groins and started...
    deleted deleted 26-30 11 Responses Sep 3

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    Hey guys. I started smoking at 14 but then quit and just started again. And idk what the best kind for beginners are r the best Right I'm smoking Pall Mall Green Menthol and I love...
    jlittle38 jlittle38 16-17, M 2 Responses 4 days ago

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    I started down a spiritual path after reading Conversations with God a few years ago. Sometimes in reminded just how short of a way I've come since then and it bothers me. I try...
    ollierosser ollierosser 26-30 Aug 20

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    Started with a Victoria's Secret magazine, then sex scenes in movies, then hardcore ****. I escalated fast, damn. I remember before I even had my balls drop.
    CJCA CJCA 18-21, M Aug 28

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    I was about 4 when i first started! I couldn't manually get myself off until i was just 15 and bought a vibrator. Even though i couldn't figure out how to touch myself, i had...
    Coraltorch Coraltorch 26-30, F 4 Responses Aug 28

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    Mine started by accident, A friend needed someone to put things together for a road construction and maintenance tender so I hopped in...with a whole heap of papers and...
    kicks2014 kicks2014 36-40, M Aug 30

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    My job was to install alarms.. Which I did meticulously and very well by company standards. I was one if the best. But I got sick of it. I hit bottom. I started to hate it...
    Sezom Sezom 36-40, M Aug 31

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    My parents died in a car accident when I was 10 and I now live with my uncle, I started wetting the bed a few days later and he made me wear nappies to bed, but then after a week...
    Jaylieg Jaylieg 22-25, F 3 Responses Sep 1

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    My parents died in a car accident when I was 10 and I now live with my uncle, I started wetting the bed a few days later and he made me wear nappies to bed, but then after a week...
    Jaylieg Jaylieg 22-25, F 1 Response Sep 1

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    I started ************ at 7 years old
    MoeRouf MoeRouf 26-30, M 5 Responses Sep 3

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    I started my own business through National Wealth Center. Everyone should definitely check it out. It's simple and amazingly helpful. My goal is to help people become financially...
    BananaPancakes88 BananaPancakes88 26-30, F Sep 7

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    I started at around 6 or 7 by accident. By climbing the rope at school, I would ****** by the time I reached the top. I didn't know what that was, but I knew it felt good. When I...
    pressure69 pressure69 41-45, M 3 Responses 6 days ago

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    i have started running and its a something new. i've never been the running type but i feel like i can do it. plus it always feels great after a long run
    llswizzle llswizzle 13-15, F 1 day ago

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    I was buying a pink shortish skirt in the local Oxfam shop two weeks ago, and the (very attractive) lady behind the counter said jokingly "It's not your colour." She couldn't have...
    ChloeCarlisle ChloeCarlisle 51-55, F 9 Responses Aug 19

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    A long time ago now I lived on my own and would dress up all the time I got so used to it and it was perfectly normal for me. One day someone knocked at the door and I went to open...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 7 Responses Aug 20

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    So I wanting some company to talk and get advice and share...I have a lot of how to?'s and would like some freinds
    jessie121412 jessie121412 41-45, M 1 Response Aug 21

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    Holy crap I think its finally going to happen. My wife just said something that threw me for a loop. Holy crap. Holy crap. More to come.
    NaughtyBecky NaughtyBecky 41-45, T 4 Responses Aug 21

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    I want a bisexual experience
    quinn2254 quinn2254 13-15, M 2 Responses Aug 21

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    I went dress shopping and found a short little summer dress in black with a lace back, and a nice flared skirt. I love slipping into it and zipping the exposed zipper up my back...
    Plugslave Plugslave 31-35 6 Responses Aug 22

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    This is a famous joke. Not true, but fun to repeat. Sam walked into the locker room to change into his softball uniform. The guys spotted the bra he was wearing and shouted "What...
    Robertredlips Robertredlips 56-60, M Aug 22

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    My friend came over to my house and he went to my room I forgot to put my pink thong away and he asked if I wear it I told him yes and he asked if I fully dressed I once again said...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 5 Responses Aug 23

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    Me in my new panties kinda a bad shot tho hehehe
    samanthacd21 samanthacd21 18-21, T Aug 26

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    My *** in my new panties... Looking for a daddy :)
    samanthacd21 samanthacd21 18-21, T 2 Responses Aug 26

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    Tried painting my nails today ladies 😘
    JessicaCD20 JessicaCD20 18-21, M 3 Responses Aug 26

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    I was caught cross-dressing. I sometimes travel to different cities for work. In nice cities (San Francisco) I rent a motorcycle on my days off and ride to the nice places. In SF...
    Robertredlips Robertredlips 56-60, M 1 Response Aug 27

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    Any teens near Hobbs nm from 13-15
    coleirleee coleirleee 13-15, M Aug 28

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    I was caught by my mum a few months ago. I was wearing some of her lingerie black tights and black heels strutting around the house. I didnt hear her come in and i turned around...
    tomcd95 tomcd95 18-21 6 Responses Aug 29

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    Yesterday the sister in law came around 2 pick summit up she left so I went and put my leggings on and knew nothing more then she came bk in 2 get her glasses I just sat and...
    24chris24 24chris24 22-25, M 1 Response Aug 29

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    and i love it. there's nothing more relaxing than coming home after a hard day at work and slipping something girly and comfortable on to make your day so much better.
    AmberRosecd AmberRosecd 31-35, T 2 Responses Aug 29

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    I have just told my girlfriend that i like to crossdress and would like some advice from a girl
    JohnnyGpoint JohnnyGpoint 36-40, M Aug 29

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