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I Have Told Someone About My Crossdressing Secret

this is a group for people who have found a way to tell people they know about their crossdressing secret. 639 People

    If you haven't figured it out by

    now from looking at my experiences, I'm a young male who is into crossdressing. To clarify that, I don't want to live my life as a transvestite, I simply want to find a girl who I can play dress-up with for fun. And just maybe if I get comfortable enough with it then we can have...
    SissyBoy9292 SissyBoy9292 22-25, M Dec 22, 2013

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    Taking A Chance

    I told my wife after three years of marriage that I was a cross-dresser. I tried to explain that after many many years since very young I had always had an urge to dress like a girl. At first she didn't take it well, I was afraid that I might lose my marriage over my secret. I...
    Rick5881 Rick5881 51-55, M 1 Response Nov 2, 2013

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    2013 Crossdressing Review I first told my wife

    that I loved to crossdress about a week after Halloween in 2006. That was our first Halloween together and I went as a dominatrix. She seemed really cool about it, so I told her the whole story. I expected the usual rejection, but she was very accepting. Since then we have spent...
    1SarahAnn 1SarahAnn 46-50, M 5 Responses Feb 8

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    I'm telling more and more people.

    The first person was my best friend, a woman whom I've known from a recovery program. We discovered that we often have the same issues but come at them from entirely different angles. For example, where I was a boy in a family that really wanted/needed a girl, she was a girl in...
    PennySterling PennySterling 51-55, T 3 Responses May 27

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    Best Day Ever

    In an earlier story, I mentioned that I told a co-worker that I was a crossdresser. I was talking to her today, and she said that she would like me to come to her house and hang out with her and her girlfriend so that I can dress and feel comfortable being me. Needless to say...
    deleted deleted 26-30 17 Responses Mar 30, 2013

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    When i got with my 2nd wife i had told her all

    about my dressing and all fetish i have. At first she played along then as yrs went by she changed and then she told my best friends wife about me dressing in my maids outfit and cleaning the house.
    sissyjamiegurl123 sissyjamiegurl123 46-50, M 3 Responses Jan 2

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    Coming Out.

    I told my brother about my crossdressing back in the mid-70's because I found some other woman's clothes around the house that weren't mine. I figured he enjoyed it as well. I was living with him since I had loaned him the money for the down payment. One evening I put on a...
    PinksWoman PinksWoman 61-65, T 1 Response Sep 20, 2012

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    Only A Couple

    Only a few people have known about me crossdressing.My ex-wife was the first to know.My parents found out one day when the ex and I were fighting and she threw all my lingerie out in their front yard. They asked if they were mine and I said yes, and we never talked about it again...
    happilymarriedguy happilymarriedguy 51-55, M 1 Response Nov 25, 2012

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    Telling The Rest with pic

    Well the desire to dress it just too much to hold back it seems. So I told my best friends wife about 2 weeks ago that I am a cross dresser and would love to wear a skirt when I wanted. She just sat there looking at me and I carried on and explained that I think guys should be...
    0hBrandie 0hBrandie 41-45, M 3 Responses Jun 10, 2013

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    My Wife Now Knows

    Saturday while the wife was gone, I decided to wash a few skirts and blouses. When they finished, I put them in the dryer.  Monday, I found them lying on the bed in a pile.  I had forgotten to get them out of the dryer before she did laundry on Monday.  She didn't say a word...
    helpmerhondas helpmerhondas 61-65, M 19 Responses Oct 2, 2012

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    I'm married and my wife does not like my

    crossdressing, so I must sneak out and do it. So one day last year shortly after my sister lost her husband I called her and asked if she wanted some company for a drink and some chatting. She said sure so next I asked if she could keep a secret. She said sure what is it? I said...
    Lara659 Lara659 51-55, M 4 Responses Dec 29, 2013

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    I told my girlfriend

    and she supports me all the way sum times when we haves sex we swap roles and she strap on does me whilst i crossdress and god it is soo fun
    sissyslave18 sissyslave18 18-21, M 1 Response Jan 15

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    Hi everyone......i am a good looking male

    who likes to wear female clothes especially lehengas and sarees....i am completely straight and like to have female friends who would help me dressing and can donate me their used clothes......
    bhavna223 bhavna223 31-35, M Dec 8, 2013

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    Volunteer Day This past Saturday was probably

    the most feminine day of my life. I was wearing my favorite brown plaid jumper with a black turtle neck, black patterned tights and black wedges. This particular jumper is a bit shorter than usual and ties in back . It feels so pretty. My hair and makeup came out very nice, and...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Feb 17

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    I Have Shared My Crossdressing With A Few Women

    There are a few women that know about my crossdressing. My wife knows, of course, but there are a few others. Mostly ex-girlfriends. From the time I entered college, the girls I dated with whom I had somewhat serious relationships all learned of my crossdressing. It's...
    BizSuitStacy BizSuitStacy 46-50, T 9 Responses Sep 14, 2012

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    What To Do Next

    Since i was about 5 i started crossdressing, at the time it was just curiosity but as the years continued i became alot more passionate towards it. Im 20 now and dont know what to do, i feel im about to burst if i dont come to terms with it but no matter how hard i try i cannot...
    baz1501 baz1501 18-21, M 2 Responses Aug 23, 2013

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    I Told My Second Person Today

    about a month and a half ago I decided that I would tell my cousin my secret. Just straight out of the blue decision but it made perfect sense because I was really lonely and I had this secret I've been keeping from literally everyone for over half my life and so not only did it...
    STLCD STLCD 22-25, M 7 Responses Jul 23, 2012

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    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 46-50, M Feb 10

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    The Shrink

    I have an appointment in ten days with the psychiatrist who has been treating my for depression. I intend to reveal my feminine personna at that time. First, because it could be helpful information in my treatment, I am much happier now living as a woman full time. Secondly...
    PinksWoman PinksWoman 61-65, T 3 Responses Sep 30, 2012

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    Not Struggling...

    you may have read my previous story called "struggling..." and probably weren't expecting an update so soon but I worked up the courage to tell my sister and not only did she take it well, we're now closer than we've ever been and I feel like it's only ever going to get better...
    STLCD STLCD 22-25, M 5 Responses Feb 25, 2013

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    I Told Someone, Finally

    I told my best friend about my crossdressing, after weeks of thinking about telling someone. I never thought that he would've been the one I told, but I'm glad I did. This had been weighing on me heavily for months and I didn't know what to do. When I did decide that I was going...
    MLPL224 MLPL224 16-17, M 1 Response Apr 18, 2013

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    I Told A Female Friend

    I'm actually not even sure how I came to tell this woman, it all seems a bit vague now. This is a lady friend who I occassionally had sex with, she's a great girl and she was the first person to ***** me in my ***, I need to tell that story too some time cus god she was good...
    deleted deleted 26-30 2 Responses Aug 26, 2013

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    I Have Not Told Anyone Yet I Was Caught

    Is it me ? It seems to be more acceptable to come out Gay than to confess to crossdressing. I know my wife likes and supports gay individuals. But is repulsed by my crossdressing. She found out last year when she discovered some pics on my computer and it was shortly there...
    angiecan angiecan 51-55, T 7 Responses Dec 2, 2012

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    Had To Admit It! ;-)

    Please read our 'Featured' Story? Caught By A Really Good Friend...! Would really Love and Appreciate your comments!!! Liss (Melissa) XX
    deleted deleted 26-30 Apr 24, 2013

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    Told My Girlfriend & Two Of My Bros A.K.A My Guy Friends

    It Was about 3 to 4 weeks ago. When I told her about it. I never dressed as a girl full time. Just at times when with my ex grilfriend. Then A few days later I told my long time guy friend a.k.a my bor he was ok with it. then a week later i told my other bor he was shocked, but...
    mrd1977 mrd1977 36-40, M 1 Response Feb 17, 2013

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    Trying To Come Out To Everyone

    I decided a while back that I want to come out to everyone I know. I have a loose game plan with an open time line to achieve this. Over the past year and a half I have prepped everyone. It started with getting my ears pierced. Everyone noticed and most questioned why and I told...
    0hBrandie 0hBrandie 41-45, M 4 Responses Mar 30, 2013

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    I Took The Chance

    I finally told my wife that I liked wearing skirts and dresses. When I her I was wearing a cream colored top and a tan and brown print skirt with a bra and pantyhose on. At first she didn't like it and then it grew on her so now she likes it. Or should I say expects my to dress...
    Adam59 Adam59 56-60, M 2 Responses Mar 5, 2013

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    Only My Female Friends.

    i've told them mainly because i trust them but also because i want them to know the real me. i only got the 4 girls that really know me.
    robotredneck robotredneck 18-21, T 1 Response Mar 25, 2013

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    Struggling...

    I'm internally struggling with wanting to come out to more people, particularly my family that I live with so that I can perhaps be more free to dress while I'm at home. So I got this new app on my iPhone called Whisper where you can tell your secrets and feelings to all other...
    STLCD STLCD 22-25, M 1 Response Feb 25, 2013

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    I Told Someone At Work That I Crossdress

    Before being laid off from woek I became fast friends with Marie, She was married, had three children and was a terrific lady.  I generally complemented her on the dresses she wore to work and we spoke a lot about many different topics.One afternoon I started a conversation...
    jml2000 jml2000 56-60, M 5 Responses Nov 20, 2012

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    I Told My Sister

    When I was back in my home-country for holliday, I offcourse visited my family. One of those visits was to one of my three elder sisters. We were sitting there with my sister, her husband and son, talking about all things and we also had some photo's to show, which I had on a...
    laikagirl laikagirl 51-55, M 1 Response Aug 20, 2012

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    If you haven't figured it out by

    now from looking at my "experiences", I'm a young male who is into crossdressing. To clarify that, I don't want to live my life as a transvestite, I simply want to find a girl who I can play dress-up with for fun. And just maybe if I get comfortable enough with it then we can...
    MysteriousLilMe MysteriousLilMe 22-25, M 2 Responses Dec 23, 2013

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    diaperedsammy diaperedsammy 18-21, M 1 Response Dec 9, 2013

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    I've been meaning to put this on I've hopefully found someone now hope it goes good for me if I get regular replies I will consider things going well if not I will wait a bout 3...
    Aireagoir94 Aireagoir94 18-21, M 2 Responses Dec 8

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    Not sure if it was a good idea or bad. Also not sure what prompted that action either. I don't think it matters even if you remove anyone from your circle coz each time you...
    uselessguy uselessguy 36-40, M 5 days ago

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    I lost an amazing guy... I really wanted to give love another try and when I met him I really felt like love would be kind... But now I have to live with another regret. I thought...
    ecoglitcher ecoglitcher 16-17, M Nov 22

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    Sorry just deleting some people on my circle. I'd rather have few on my circle than have a long list but you never actually spoken to them.
    Lakee112812 Lakee112812 36-40, F 2 Responses Nov 21

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    Lost my mom. I've seen here such beautiful pictures of a mother with her daughter. And these beautiful pics made me so infinitely sad again. Because there will be no more such...
    prettysybill prettysybill 22-25, F 3 Responses Nov 22

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