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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. 562 People

    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 4 Responses Nov 20, 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 1 Response Aug 23, 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 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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    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 18-21, M Dec 22, 2013

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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 2 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 6 Responses Feb 25, 2013

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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 18-21, M 1 Response Dec 23, 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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    Revealed The Tip Of The Iceberg

    I have started down the road of revealing myself. So far it's been hard work but well worth it. I would recomend it to anyone.
    Heellover Heellover 36-40, M Nov 25, 2012

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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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    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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    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...
    Brandie1960 Brandie1960 41-45, M 5 Responses Mar 30, 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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    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 16 Responses Oct 2, 2012

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    diaperedsammy diaperedsammy 16-17, M 1 Response Dec 9, 2013

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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 6 Responses Sep 14, 2012

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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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    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 2 Responses Apr 18, 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'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 2 Responses Dec 29, 2013

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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...
    Brandie1960 Brandie1960 41-45, M 3 Responses Jun 10, 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 Jan 15

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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 4 Responses Feb 8

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    Related Experiences

    Me and my girlfriend have been home naturists for about 5 years and have started going to holiday places where we can be naked outdoors. Before I told anyone, I really thought that...
    BarefootNorthWest BarefootNorthWest 31-35, M 3 Responses Apr 3

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    Recently I talked to a suicidal girl who needed help. She told me all that was wrong with her life and I told her all that was wrong with mine. She had plans, she knew what she...
    girl3255 girl3255 16-17, F 2 Responses Mar 24

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    This is hard because I never really was able to talk about it til now. In 2011 I received a phone call on the 4th of July. A mom who was outraged with me had thought her son ran...
    deleted deleted 26-30 1 Response Apr 6

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    I saw my best friend take suicide in front of me. He was 16 and handsome. Suicide doesn't kill someone, its sadness. Being judged Feeling like you have no one Suicide is being...
    ILYBlackVeilBrides ILYBlackVeilBrides 13-15, F 5 days ago

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    I saw the marks on her arms. I passed her a note saying she can talk to me and trust me. She texted me days later things I can't keep a secret. I valued her life over my trust. Her...
    Qwerkyqwerty Qwerkyqwerty 16-17, F Apr 9

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    Last night I told a good friend of mine how I truly feel. She proceeded to tell me that I was none of those horrible things and I deserve happiness. I deserve someone to treat me...
    EmptyAgain EmptyAgain 16-17, F Apr 6

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    I was in 6th grade at the time and me and this other girl were in lunch detention. As we sat there I saw she was covering her wrist with tape so I asked her not know what it...
    XFallinAngelX XFallinAngelX 13-15, F 1 Response Mar 24

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    I had a friend once. Her name was Denise. She was so beautiful. She got kicked out of our school last year because of an issue. She transfered to a good school, and she was happy...
    defi4nce defi4nce 16-17, F 1 Response Apr 2

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    To ache for them but knowing you can't ever mention how you feel. Suspecting they feel the same but being stuck to someone you don't love anymore. Looking for them every...
    Valtielislord Valtielislord 18-21, M Apr 3

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    I am good at keeping secrets.Thanks for sharing ;)
    4biandu 4biandu 26-30, F 1 Response Apr 9

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    I lost my best friend who I was like in love with back in 2010 to a drunk driver. To lose someone you love is to alter your life forever. You don’t get over it because ‘it...
    krorenae krorenae 18-21, F 1 Response Mar 25

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    He told me he loved me. And I love him too.
    ithzelhernandez ithzelhernandez 16-17, F 1 Response Apr 9

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    FOR MEN WHO LIKE TROPHY WOMEN: The prettier they are the more psycho they are... only in the most rare cases will you find the one who isn't.. even then she still requires a lot...
    destinyisfate destinyisfate 22-25, F 6 Responses 6 days ago

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    I was standing in the kitchen. Someone found something I REALLY dont like today. One of dads friends. Some girl is here to make dinner and take Jake to lacrosse. She's making...
    deleted deleted 26-30 Apr 10

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    I don't know why I do it to myself, but it's a vicious circle. I feel bad about myself, I have sex with someone who couldn't give a **** about me, I'm left feeling empty and sick...
    Destrxctive Destrxctive 16-17, F 2 Responses Mar 24

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    Im about to get diverse but I don't want to stay alone. I have no family here and even though there's barely any love left i hate this feeling. I told her to move out, but every...
    Andre77 Andre77 22-25, M Mar 26

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    Ya I've killed....with my good looks!!! Ooo seriously why do they have this category if someone really did kill someone wouldn't they be in jail or if it was they line of duty like...
    kendralyn kendralyn 18-21, F 1 Response Mar 30

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    First I thought I was bi,but now I'm not so shure .i find myself really attracted to girls but never to boys.Im afraid to come out,every time my friends talk about lesbians there...
    crazcat97 crazcat97 13-15, F 2 Responses a week ago

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    Well i don't know about that. But i saved two little boys who were tangled in a large wild shrub (like 2X3m) of thorns. They were stuck for 2 hoers and i heard them. I went there...
    LunaOanaAris LunaOanaAris 16-17, F 1 Response Mar 23

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    I've gotten called names many times before but this one time a girl at school just came up to me and called me a sl*t and I have her that look saying 'look who's calling who a sl*t...
    bulimicbixtch49 bulimicbixtch49 13-15, F Apr 11

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    I have not posted on here in two weeks. Because of the last two weeks I've lost someone else that I love. I cannot believe how bad 2014 is. Every month brings a new death. I've...
    Shmily68 Shmily68 41-45, M 2 Responses Apr 14

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    I've been thinking of committing suicide lately, in the next few days to be honest. If someone could message me that'd be great..
    beth1999 beth1999 16-17, F 2 Responses Apr 14

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    Hm... Well a couple nights ago, someone called me a c.u. Next. Tuesday. And I became an emotional wreck. I was called word but that was my braking point. So when I got home that...
    LucyGirlAkita2 LucyGirlAkita2 16-17, F 1 Response Apr 14

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    If my own dad told me to I should.
    Wishingtobegone Wishingtobegone 13-15, F 2 Responses 3 days ago

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    Every year my church does a 30 hour famine. I have done 5 30HFs in my life and I look forward to more. I save lives from hunger and that's a big deal. Every 7 ppl die from hunger...
    XFallinAngelX XFallinAngelX 13-15, F 1 Response Mar 24

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    But I have ruined countless others.
    weskeralbert weskeralbert 22-25, M Mar 25

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    This is something that I have done and will do again many a time. I am not proud of doing this, but every time I've done it, it fills me with pleasure, releasing all my anger in a...
    tatersgonnatate tatersgonnatate 18-21, M 1 Response Apr 10

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    (My daughter is a 20 year old college student living at home, her boyfriend is 22 or 23 living with his parents.) I don't know what it is about this guy, he is nice and even seems...
    sillyme89 sillyme89 41-45, F 2 Responses Mar 26

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    I have made a lot of mistakes towards the one I love and now we are over .. For good. I gave up everything and now it's all thrown away too nothing. Just last night I wanted to...
    Stranglyokay Stranglyokay 16-17, F 1 Response Apr 14

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