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

Personal Stories, Advice, and Support 470 People

    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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    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 1 Response May 23

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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 3 Responses May 23

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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 8 Responses Mar 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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    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 6 Responses Jun 2, 2013

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    Related Experiences

    I started dressing in my mothers clothes when I was 10 with her leotards and tights. By the time I was fourteen I was wearing all of her clothes and dressing anytime I was home...
    MichelleTiedup MichelleTiedup 22-25, M 1 Response 4 hrs ago

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    It's still a subject that brings me much shame but it's nice to find a place where I can open up. When I was 18, I got into a relationship with someone that I grew to love deeply...
    Normienorman Normienorman 22-25, F 12 hrs ago

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    I really really want to find a young teenage boy who is very submissive, slightly masochistic, can play a boy who is easily shy, easily embarrassed and willing to becoming a young...
    TheCuddlySuccubi TheCuddlySuccubi 22-25, F 4 Responses 1 day ago

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    Preferably a submissive/switch, Any age under 22! Slightly feminine, easily embarrassed, innocent, very shy, clumsy, confused, forgetful, child-like, cry-baby, cute, clingy...
    TheCuddlySuccubi TheCuddlySuccubi 22-25, F 7 Responses 2 days ago

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    Because of the fact that I was molested I thought that touching private parts was a type of game so I did it with other kids. I never forced anyone. I just asked because I just...
    Lookin4answers123 Lookin4answers123 13-15, F 1 Response 2 days ago

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    When I was younger I would sneak into my sisters room and put on her clothes. I loved being a woman. The feeling of the soft tight clothes around my body. Every time I made a new...
    clevername11 clevername11 18-21, M 3 Responses 2 days ago

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    My name is Vicky. I have cerebral palsy. I went to a boarding school near Brighton. I was a pretty girl then. I had long blond hair. I am slim as well as being quite small. I...
    vickybiggs vickybiggs 18-21 1 Response 3 days ago

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    i have no idea why i was very nice.....................
    hopelove24 hopelove24 22-25, M 3 Responses 4 days ago

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    The first time I got bullied by boys I was in grade five. I was listening to my Walkman at recess and a boy in my class whipped some kind of wet shoelace in my face. There were...
    katariffik katariffik 31-35, F 2 Responses 4 days ago

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    I'm a young boy who still is in diapers 24/7.
    tylerlovesdisposablediapers tylerlovesdisposablediapers 16-17, M 4 days ago

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    Looking for someone age 13-17 to trade foot pics with me :)
    deleted deleted 26-30 5 days ago

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    I didn’t get to do it very often, and I’m sure I’m over-romanticizing a bit, but I do distinctly remember enjoying 1) playing with the girls instead of the boys, and 2...
    mickitg mickitg 41-45, T 6 days ago

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    I love my scout leader, he is funny, kind, always helps me and I think I love him.
    tortchy tortchy 13-15, M 1 Response 6 days ago

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    Hello! I am Alex but now Alexa.I was a boy earlier but now I am a girl for almost 4 years.I want to share my embarrassing transformation with you. This is how it all started. I...
    Alexa910120702 Alexa910120702 13-15, T 2 Responses 6 days ago

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    Big decision to make and I need some advice. So allow me first to give you some background. I first met my wife not too long after a really bad heartbreaking relationship where I...
    TiredDaddy TiredDaddy 41-45, M 1 Response 6 days ago

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    Big decision to make and I need some advice. So allow me first to give you some background. I first met my wife not too long after a really bad heartbreaking relationship where I...
    TiredDaddy TiredDaddy 41-45, M 2 Responses 6 days ago

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    I really want to see some more great boy feet
    saltofthesea20 saltofthesea20 26-30, M 1 Response 6 days ago

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    I am writing this to shed light on domestic violence and what happened to me. At first it was only on my Facebook and set to "Friends Only", but I am now making it public and...
    Taylor62298 Taylor62298 41-45, F 1 Response 6 days ago

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    I would like opinions on what you guys think. It may be a little long but please listen. It starts when I was maybe five. Please keep in mind I am diagnosed GAD and sleepwalk/talk...
    LynnT94 LynnT94 18-21, F 3 Responses a week ago

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    Ever since the first time I was penetrated when I was 11 by a younger boy, I have been a bottom to other younger boys. I am now 17 (18 in September) and am a total bottom for...
    BCdiaperBoy BCdiaperBoy 18-21, M 1 Response Aug 22

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    Talking about stuff with people online is great, but I need more than that. I need what I have never had, someone to hold me and comfort me when I am sad. No one has ever done that...
    stewartgreen stewartgreen 18-21, M 3 Responses Aug 22

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    I don't like flirting or waiting around to find out if a boy likes me. I straight up ask, that way I don't have to waste my time worrying about it. It's okay if he says no because...
    hiddenkitty hiddenkitty 18-21, F Aug 18

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    Ever since I was in middle school, I have wanted to be a boy. What I mean is that I want the freedom to dress in men's clothing and not get horribly judged for it. I want to be...
    immaturity immaturity 16-17 Aug 18

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    when i was young i use to take a lot of s*** from my parents but i'm sick of it now from the hell they caused me i wont and and have nothing to do with them!! they are in my past...
    Lrose12 Lrose12 36-40, F 3 Responses Aug 18

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    I chased an idea down to deeper, darker waters and never quite made it back to shore. Everything was more than it seemed. What was it I'd been pursuing again....something to swim...
    s0undgarden s0undgarden 16-17, M 1 Response Aug 17

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    I think I brought it on myself a lot, I was weird, when everyone was talking this one time I asked the teacher to ask my fellow pupils to keep it down, mainly because I couldn't do...
    VerticalCirrus VerticalCirrus 22-25, M 5 Responses Aug 16

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    It took me a moment to realize I qualify for this one. You see, I began dressing as a girl the day I was born because my mom had been sure I'd be a girl so that's all that was...
    AlbertSAT AlbertSAT 66-70, M 2 Responses Aug 15

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    I can't be in public anymore because I feel so hurt and ashamed and worthless and hopeless when I see a beautiful girl with her bf or even a single girl. It makes me feel small and...
    Thefightingangel Thefightingangel 22-25, M 2 Responses Aug 14

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    Here are some notes on putting boys in dresses. The crucial variable is the child's age. The younger he is the easier it will be. Very young boys often enjoy dressing up in girls...
    TeachingRespect TeachingRespect 51-55, F 2 Responses Aug 14

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    Here are some notes on putting boys in dresses. The crucial variable is the child's age. The younger he is the easier it will be. Very young boys often enjoy dressing up in girls...
    TeachingRespect TeachingRespect 51-55, F Aug 14

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    It was back in 1980, my wife came home from work & told me we were going to a costume party at one of the girls she works with house. my wife told me I was going as a girl since...
    lovebeingJoann lovebeingJoann 56-60, F 2 Responses Aug 14

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    Why Girls are Yucky: Boys begin to develop their contempt for the opposite sex at an early age. Certain aspects of this process have been documented in Boys and Girls: Superheroes...
    TeachingRespect TeachingRespect 51-55, F 3 Responses Aug 13

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    when i was smaller and more alive inside. i sung songs about God and His son to my neighbor. i laughed and cried as needed. now, let this soul and mind and heart be a vessel of...
    cosmosdrift cosmosdrift 31-35, F 2 Responses Aug 13

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    My mom aunt and sister were planning on a going on a girls trip to Florida for two week and I want to go. I asked if I could go they said that the only way I could go was to dress...
    Flash123456 Flash123456 22-25, M 1 Response Aug 12

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    my friend and i were roommate in our dormitory. i always in love for his feet.one day we start to play football. David was a good player also he has a beautiful face and nice big...
    goal9880 goal9880 18-21, M 1 Response Aug 12

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