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I Have Been A Crossdresser For 30 Years

Personal Stories, Advice, and Support 66 People

    I Have Been A Crossdresser For 30 Years

    It's been over 30 years I've been crossdressing. It's seems not very long.  I started when I was 11 or 12.  I wore mom's bra and panties.  and absolutely enjoyed them.  *** I looked through my mom's dresser drawer I found her girdle and nylon stockings.  I just had to try...
    jml2000 jml2000 61-65, M 2 Responses Feb 6, 2013

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    At Least 30 Years!

    Apart from when I was in the Royal Navy, even then I did it when I was on leave, I have crossdressed. Having two older sisters helped and I would wear their clothes whenever I could. Now I am married and my wife loves it when I crossdress to such an extent that we have days out...
    wetrev wetrev 46-50, M Mar 10, 2013

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    30 Yrs+

    I started cross-dressing when I was about 13/14 yrs of age by pinching a pair of tights/pantyhose from the sister of a school mate but it was not until a few years later that I decided to try fully dressing in female clothing, & when I did start I found out what I had been...
    xdpaul xdpaul 56-60, M 2 Responses Jul 27, 2013

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    Related Experiences

    So sad to think that all the other pages have hundreds of experience shared and only 32 on this page?
    Bilharzia Bilharzia 31-35, F 1 day ago

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    Yes, I guess it has been "way too long" now. I do not even know how it came to be so long. Time has just passed very promptly. At first it was all about healing, then becoming more...
    GhostPizza GhostPizza 31-35, M 1 Response 1 day ago

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    People always ask me why I'm single? I really don't have answer to them. Even after getting 4-5 proposal from girls I didn't accept them just because I was not sure, I could manage...
    Srey24 Srey24 16-17, M 2 Responses 2 days ago

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    I've been single way too long waiting for the right woman to come in to my life. 5 years seem to long
    Anthony2400 Anthony2400 22-25, M 3 Responses 3 days ago

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    just me wondering why i didn't even do anything like i only messaged by "hello there" just really curious about someone so i messaged for knowing how he is?!!!!!!! now i am blocked...
    GamesBOSS GamesBOSS 18-21, M 4 Responses 3 days ago

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    I've been single for waaaaaaay too long
    VirginGuy55 VirginGuy55 18-21, M 4 days ago

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    All my friends are in relationships and I'm on my own and have been for 3 years
    deleted deleted 26-30 3 Responses 4 days ago

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    Maturegurl where are you?....how strange
    mikemcneil mikemcneil 51-55, M 4 days ago

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    This is a true story of what happened to Greg Zaffuto. I have just experienced much the same and do not want this to happen to you, so I am sharing the following. I apologize for...
    Grace2U Grace2U 66-70, F 6 days ago

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    It was the spring of my freshman year in college, and I had recently broken up with the first guy I’d ever slept with. I was in a coed dorm, and M lived across the hall, a good...
    Multiversality Multiversality 46-50, F 3 Responses 6 days ago

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     THINKING ABOUT THE VERY FIRST TIME I MEET THAT IDEAL POZ FEMALE WHO UNDERSTANDS WHAT IM GOING THROUGH AS FAR AS TRYING TO DATE SOMEONE WHO IS NOT HIV POZ 
    suckherfeet suckherfeet 36-40 a week ago

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    and I still am! My boyfriend/Master is 13 years older than me. We have been together almost 3 years and we live together and are very happy
    ServingGirlUK ServingGirlUK 18-21, F 4 Responses a week ago

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    So at the end of 2014 I found out that my best friend of 9 years and her bf plotted to use me for my money and my helpfulness. We had always talked about our future and things we...
    aquamoongoddess aquamoongoddess 22-25, F 2 Responses a week ago

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    yes i've been blocked for no reason, just said hi and been blocked -_- i hate when people judge you before that they get to know you
    Heythame Heythame 22-25, M 3 Responses a week ago

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    BULLYING AS A DOMINO EFFECT ... My father group up as an orphan because his parents were killed in the second World War and he suffered at the hands of the German soldiers that...
    LozzyFromRome LozzyFromRome 46-50, M 3 Responses Feb 4

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    now I know this is nothing compared to some of the stories I just seen on here, but here it goes....I started dating my boyfriend almost 6 years ago...during the 6 years we have...
    teeq22 teeq22 18-21, F 3 Responses Feb 2

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    I don't really know where to start. I've been with my boyfriend for 2 and a half years. Everything was lovely and fine, we were both happy. We argued, but doesn't everyone? We got...
    Jennywirral Jennywirral 26-30, F 2 Responses Feb 2

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    When I was three years old my parents were killed in a car accident. And I was sent to live with my aunt and uncle. My aunt and uncle loved me very much although my aunt was very...
    meneme2013 meneme2013 18-21, M 1 Response Jan 31

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    Last week I told my mom I had done all my chores and I was going to my boyfriends house Well she came home and I didn't do anything she waited till I got home Then that's when she...
    deleted deleted 26-30 Jan 31

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    My wife is my soul mate and best friend
    Gag1948 Gag1948 66-70, M Jan 31

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    My ex friend would stalk my sister on social media and then lie about it to my face after my sister confronted me. I had been friends with him for years at that point and he never...
    awaywego4 awaywego4 26-30, F 1 Response Jan 31

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    Day 2.. Rejected 2.. Don't ever entertain who says "love you" with in one day.. Hehe.. **** happens..
    zmilenseor zmilenseor 31-35, M Jan 29

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    The guy I was with recently dumped me and I realized that all the significant, romantic relationships I have been in have been abusive in some form. They've either flat out abused...
    terrywill15 terrywill15 18-21, F 2 Responses Jan 29

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    I worked in construction for fifty years. Worked in wood houses and concrete and steel buildings. Have done things just to get it done now instead of waiting for all kinds of...
    boldtimer boldtimer 66-70, M Jan 28

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    I got rejected thrice today.. Let's see what happens tomorrow.. :)
    zmilenseor zmilenseor 31-35, M Jan 28

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    ive been married 29 years and my wife has cheated on me hundres of times with atleast15 diffrent people in the last 4 years shesysshell stop andiwant to belive her but how can i...
    mondokahuna mondokahuna 51-55, M 8 Responses Jan 27

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    Tonight he threw my dinner at the wall. I have been snowed in without access to my car as it is BURIED in snow. On my boyfriends way home I had asked him to pick up something...
    dcp1058 dcp1058 26-30, F 5 Responses Jan 27

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    I have been in an age-gap relationship for almost eight years. I'm 27 years old, my wife is 48. I love her very much, and I'm looking forward to many more years with her.
    deleted deleted 26-30 1 Response Jan 26

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    Don't lie yourself girl! you are lazy for real! you can't do it for real! Why you said it was not your fault? it's not because of the weather, your illness, situation, people...
    kimlys kimlys 18-21, F Jan 26

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    Today, I had another conversation with my mom. Yes, I love her. Yes, she was there and saw (all of the abuse of me and my siblings.) Hard for her. She spends her days trying to...
    frspch frspch 51-55, F 6 Responses Jan 25

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    I'm bored so I'm going to tell you a story. This started summer of 2015. I met this guy in an online game, I hate how I can still remember it like it was yesterday. He was offering...
    zoelalala zoelalala 18-21, F 20 Responses Jan 23

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    I feel like I have been cheated on by someone who I been with for the past almost 4 years. How could someone else just go behind my back and have sex with someone else without...
    agdnn agdnn 26-30, M Jan 22

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    But I don't regret this one :) I had a crush on this girl who everyone liked because she was really pretty, but loads of girls were really pretty, the difference was she was a...
    imlegallyblind imlegallyblind 13-15, M 1 Response Jan 22

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    I am so glad this is real and I am not alone. I have been waking up multiple times a night in a cold sweat due to my fears. someone or someTHING is controlling me to do, think and...
    Apathy420 Apathy420 18-21, M Jan 22

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    I totally agree with you something isn't right but I do not even know what it is ..I need someone with psychic abilities to tell me what is going on ..there is something quite...
    Inthedark16 Inthedark16 36-40, F 2 Responses Jan 22

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    hi have been single for 35 years hi am a very broken hearted A B trying to find love & friendship or relationship hi live in UK Kent area
    Kittymad1968 Kittymad1968 46-50, M 1 Response Jan 21

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    I have forgotten what it feels like to have a body pressed against mine, what skin to skin contact feels like. Intimacy has become a foreign concept to me
    Madison18 Madison18 18-21, F 7 Responses Jan 21

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