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I Loved Dressing As A Girl When I Was Just A Young Boy

Personal Stories, Advice, and Support 557 People

    My Hidden Shame

    It all started when I was around 11 me and a girl from school lived next store to each other so we would hang out sometimes one day when we were bored we went up to her room and had a game of (girls)as she called it so we dressed up in dresses and heels and messed around...
    callmebabygirl callmebabygirl 26-30, M 5 Responses Jun 2, 2013

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    Nieces Clothes

    One day, my aunt brought several bags with clothes of her girls not fitting any more or what they were not wearing any more. Her daughters were 1 year older and 1 year younger then me. One day, in my curiosity, I went through the bags to see what clothes they worn and at one...
    Kadya Kadya 41-45 3 Responses Apr 13, 2013

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    Didn't know why - just seemed natural.

    It started when my mom was so sure I'd be a baby girl that she insisted all her baby shower gifts and other preparations be for a baby girl. So I can honestly say that cross-dressing for me began before I was born. She kept me in diapers and dresses until my little sister was...
    AlbertSAT AlbertSAT 66-70, M 4 Responses May 23, 2015

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    for me it was done out of love I still knew who

    and what I was but for this one person it was done out of love for them it was fun playing as a girl no matter what age we played or playing with dolls or even role playing with me as the young innocent girl and her dressed as the James dean look and trying to be the first to...
    rickibrat2 rickibrat2 61-65, M 3 Responses May 23, 2015

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    The Shopping Trip

    Hi Folks: I still owe you the second part of the true story about my GF. I had a hard drive crash and I'm still trying to recover my files. Like a dummy, I did not back anything up. I hope to recover the files rather than have to start from scratch. In the mean time I'd like to...
    francenemarch francenemarch 66-70, F 1 Response Jun 19, 2013

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    Discovering Silky Panties For The First Time

    I wanted to revisit my childhood and give a little detail of how I started. I really don’t remember any of it but a short time after I was born my mom went back to work. Consequently I was sent to a family friend who babysat me. This went on until I was almost 4 years old. (The...
    francenemarch francenemarch 66-70, F 7 Responses Mar 2, 2013

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    Related Experiences

    I've never really told anyone but most of my fantasies involve men older than me by at least 10 years. I guess I just like the idea of being used by men that have authority, I've...
    meeknick meeknick 22-25, M 1 Response 7 hrs ago

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    In 7th grade, when puberty was in full regalia, I was an awkward, very shy girl who was desperate for a little bit of attention from my peers. I devised my plan for acceptance in...
    PoizonApple PoizonApple 31-35, F 2 Responses 10 hrs ago

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    I was kinda disappointed with the movie "What If/F Word" coz I wanted them to stay as friends. I went to an exclusive school for girls, but most of my friends outside school are...
    aremcee aremcee 31-35, F 18 hrs ago

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    When I was little I'd always loved going to my cousins house. No matter how much begging it took from both my brother and I we'd fight onwards with our dad until we won the battle...
    Peanut18 Peanut18 13-15, F 1 Response 1 day ago

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    When you finally meet the right guy, it's amazing, life becomes more beautiful. I've been dating my boyfriend Doug for 7 months now. He is the love of my life, the perfect guy, I...
    Sparklediva Sparklediva 18-21, F 1 Response 2 days ago

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    I didn't... Well yeah I did but this experience is about a friend of mine. :) I play the saxophone and being in the church's band, I had the chance to teach it to a girl four...
    EarlPhantomhive EarlPhantomhive 18-21, F 2 Responses 2 days ago

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    Hi everyone. I'm kinda shy and love to play piano.
    SethBanterson SethBanterson 13-15, M 1 Response 4 days ago

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    There is a user on here who's age category is 18-21. This user liked some of my stories and sent me private messages. Didn't take long before our conversation went sexual. She was...
    1luckytraveler 1luckytraveler 36-40, M 1 Response 4 days ago

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    Forbidden Fruit I loved someone. For the first time in my life i could actually say i loved someone. He....he was what i was looking for. Someone honest, someone who had felt the...
    PanPagan PanPagan 16-17, F 1 Response 4 days ago

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    I have a really difficult time trusting boys because when I was younger I was beaten up by them at school. I never did anything to deserve that kind of treatment but the boys at my...
    wendiemyers46 wendiemyers46 13-15, F 2 Responses 6 days ago

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    Any older men want to have some fun ill do almost anything :)
    Shadrinz01 Shadrinz01 13-15, M a week ago

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    He lead me on. I was so weak at the time and he knew that. He told me he loved me and that he would never leave me. We talked every night until we went to sleep. After hanging out...
    MadisonDaWarrior MadisonDaWarrior 13-15, F 5 Responses Feb 2

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    I am not a girl, but I have always loved feeling girly. Crossdressing has always been an escape for me. The chance to spend a few hours as someone else/your female self is...
    Michelleinside Michelleinside 31-35, M Jan 31

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    I'm an older "daddy" type guy looking for a younger boyfriend in BC , Canada
    NanaimoDaddy NanaimoDaddy 46-50, M Jan 30

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    Today, my family and I mourn the list of a very special lady, my most amazing aunt, she and my Uncle had 17 children lost count how many grand kids, and great grand youngons, they...
    AngeleyesUponU AngeleyesUponU 41-45, F 6 Responses Jan 29

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    being made fun of,teased,ignored,insulted and pushed to the ground can make your heart hurt...this has gone on ever since 1st grade and I really need support....I don't know why...
    spiritfox1374 spiritfox1374 13-15, F 2 Responses Jan 29

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    I think back to when I was younger and how I felt then. I really admired the older teen girls and so wanted them to notice me. I wonder if girls that age now feel the same.
    pklees pklees 18-21, F Jan 29

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    I'm a 19 year old guy, I like having my own boobs but I need to get back in shape. I do wear panties more than I do boxer briefs (besides, panties don't chaff my legs). I tend to...
    Soontobegirl Soontobegirl 18-21 3 Responses Jan 28

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    back in middle school, I was friends with religious people and I didn't realize it at the time. so I openly said, subconsciously, that I wanted to learn Wicca and mysticism and all...
    animefan22 animefan22 18-21, F 1 Response Jan 27

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    Well, I guess it started when we lost my mom. Part of me blamed myself even though I was younger. And my dad blamed me too. Ever since then he's lashed out at me a lot, and hurt me...
    JadeCrystalLake JadeCrystalLake 13-15, F Jan 27

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    I can't take this anymore...NO! NO! I refuse to be a normal teenage girl and freak out. But I can't take it. I really don't know what to do...or how to do it. I can't even...
    deleted deleted 26-30 3 Responses Jan 27

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    I've been mistaken as a girl on the phone when i was younger they thought i was my mom and talked to me for 4 minutes before saying hi (my mom's name) how's it going and I'm like...
    PurpleMonkey34 PurpleMonkey34 22-25, M Jan 27

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    I remember being petrified of becoming a bully target. Like God, if you ever let someone make you cry or lose your composure there's no escape, ever. I think there's a...
    JohnInKansas JohnInKansas 70+, M 1 Response Jan 27

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    I was the shy quiet kid, when someone began bullying me I got angry pretty easily and never reacted well or handled it well...so that made more people come and mess with me. It was...
    Jason947 Jason947 18-21, M 2 Responses Jan 27

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    i was bullied so much as a kid in school they bullied me because i have special needs i was bullied from age 6 too age 11
    autism1011 autism1011 22-25, M 5 Responses Jan 26

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    During grades 5-8, I experienced a lot of racist remarks by my classmates and other kids (before I start I'm going to add that I'm half black, half asian). At first glance they saw...
    illegalciv illegalciv 16-17, F 4 Responses Jan 26

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    If anyone asked me about getting myself into a rebound relationship a couple of years back, I would have laughed at them. I had never envisioned myself getting together with some...
    myeyesareanocean myeyesareanocean 22-25, F Jan 25

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    I am a quiet and easy to be bullied-girl type. Thats why its rare for people to care abt me. Then one day, i found a boy who really care about me, he know when i feel sad even if i...
    osh0412 osh0412 18-21, F 2 Responses Jan 25

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    simply cannot remember a time when my younger sister (the baby of five siblings) did not express a distinct and vehement desire to dress like a boy. Aged two, she was found...
    janecool janecool 16-17, M 2 Responses Jan 25

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    I'm tired of not experiencing a relationship. Whats its like to have a girl around and doing everything together. I don't know what its like to have a girlfriend. I was in a...
    Thefightingangel Thefightingangel 22-25, M 1 Response Jan 24

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    What's worse is when it's my boyfriends daughters birthday and her mother doesn't bother calling back or texting. Probably lying to the little girl on her eighth birthday and...
    prettyprude prettyprude 31-35, F 1 Response Jan 24

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    Most of my few friends embraced their teenage life. But for me it was one of the most darkest phase of my life. I was 12-13 when I entered secondary school. I wasn't quite sure...
    taeayumu taeayumu 26-30, F 1 Response Jan 24

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    I am unloved, but I choose to love deeply. (hopefully a positive tone for those that feel hopeless; and no, this is not a story of a girl who felt like she could never have love...
    notreallyici notreallyici 26-30, F 1 Response Jan 23

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    When I was young my sister use to dress me as a little girl, NW that I'm older the feeling to dress on my own is coming back & the thought is exciting . anyone else feel...
    myloveislace myloveislace 16-17 Jan 23

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    Actually every woman/girl I've dated, including my ex, was younger than me. :-)
    tiger3cub8