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I My Mom Buys Me Dress And Skirts, I'm A Boy

Personal Stories, Advice, and Support 353 People

    Connie & Mommie

    Hello again,Connie here, I wanted to talk about my relationship with my mom, I wrote how I told her of my desire to crossdress before in another story, The thing any of you guys wanting to tell a loved one should know is something I found out. If someone truly loves you then your...
    connie2much4me connie2much4me 56-60, T 7 Responses Apr 1, 2011

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    My Mom Lets Me Wera My Sister's Lingerie And Dresses

    When my sister left for school, mummy was lonely for her little girl, so she would encourage me to dress up as a girl and  wear my sister's clothes. I loved putting on her knickers and getting a hardon. I liked to wear her bras and slips then put on her dress and pretend I was a...
    279cr279 279cr279 56-60 13 Responses May 12, 2011

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    Not Really

    Well my mother didn't by me dresses, but my wife does and in this way I see her also as my Mom and that' why I'm saying my Mom buys me dresses and skirts
    laikagirl laikagirl 51-55, M 1 Response Jun 8, 2012

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    Am I Right Or Wrong?

    my 5 year old son has always prefered wearing dresses to trousers. he likes to be called by a girl's name rather than the boy's one that i gave him at birth. he is happy when other people mistake him for a girl and tell him he looks cute and pretty.. i allow him to wear whatever...
    sunstorm sunstorm 36-40, F 17 Responses Aug 3, 2011

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    My Store

    Ok it start when I was In grad 7 I'm Going to grad 10 I'm 15 I wii start from the begging When I whs a lone I when't to my mom room and toke some of her clothes and one day I cutout a jean skirt out of my jean one day she fond the cut jean and sed to my do u what a skirt and...
    coolman2013 coolman2013 16-17, M 4 Responses Jul 15, 2013

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    Related Experiences

    I love to wear silky satin skirts, blouses,, dresses, night dresses, bras and panties. So it's nice and feels so comfortable to wear. I just love love love to be a girl and i can't...
    Pinkygir Pinkygir 16-17, M 1 day ago

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    I'm 16 years and a guy. I want to be a complete girl like my sister. But my family will be against it. I want to have breast and vagina to be a girl. But i have no way and no money...
    Pinkygir Pinkygir 16-17, M 1 Response 2 days ago

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    Growing up, everyone knew I was different.. I loved to play with my sister's Barbie doll and I played with the girls back in school. It was so obvious I was different and I got...
    knightw10 knightw10 26-30, M Apr 29

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    She was my English teacher last year (junior year) and she was very kind. Absolutely beautiful, cute and smiley Asian woman, 23 years old. Soft black hair. Now it's senior year, I...
    keelay9947 keelay9947 18-21, M 3 days ago

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    I pretend I'm okay. What other choice is there? When you are surrounded by absurdity and then are greeted by people that have never experienced absurdity in their lives and give...
    QuestionMarks QuestionMarks 41-45, F 2 Responses 6 days ago

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    It’s been difficult couple of days in the world of Room101 and my continuing battle with all things digital. It all began, when disaster apparently struck, on Monday night. You...
    xxRoom101xx xxRoom101xx 41-45, M 3 Responses 19 hrs ago

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    I recently thought about talking about cd with people and specially with the wives shouldn't be such a problem cause what do we have to be shame about? It's not that we chose to be...
    Danairis Danairis 46-50, T 2 Responses May 7

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    So since the day I start middle school everybody ignored me and I got a teacher who taunting me, accusing me and hurt my feelings. It was a women who really don't like me, or...
    Chichikun10 Chichikun10 18-21, M 2 Responses 5 days ago

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    I love my job as a trauma nurse, and I love it when it's my turn to be on call for flight responses; however, it's extremely difficult when there's absolutely nothing we can do to...
    McCannT12 McCannT12 41-45, F 1 Response Apr 28

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    Okay so this is kind of a question, I'm a 20 something year old woman, the guy in question is also in his 20s. I met this guy over Xbox live. Well him and two other people he was...
    AriumBlack22 AriumBlack22 22-25, F 1 Response May 4

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    This has happened a few times and it's making me very curious as to why.. I'd be talking to someone and in the middle of our conversation they turn around and walk away as if...
    DarknessOnFire DarknessOnFire 18-21, M May 12

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    I'm leaving soon for a much needed trip and I cannot wait to make my playlist. I want songs that I can sing at the top of my lungs while driving down the open road.There is nothing...
    KuriosityKills KuriosityKills 31-35, F 1 Response May 17

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    Hello there, my name is Adam. I know that several of you are already aware of who I am. I also realize that many of you loathe me. Part of the reason for that is that I am not...
    SupernaturalScientist SupernaturalScientist 22-25, M 1 Response May 17

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    Hi everyone. I doubt anyone really gives a **** but I am 22 years old with nothing to show for and have hit rock-bottom in life. I have always been spoiled by my mom and my fathers...
    divinit3 divinit3 22-25, M 1 Response 6 days ago

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    Take a moment today between beers and burgers and thank t h e millions of military personnel that gave the ultimate so that we can Live In The Freest Country In The World Yes it...
    love2lickity love2lickity 51-55, M 6 hrs ago

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    I get the urge to kill sometimes and I thought it would be gone if I didint Se my mom's ex but it appears that I was wrong....
    BloodyINSaNITY BloodyINSaNITY 13-15, F 9 hrs ago

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    Just had the second dream about cross dressing 2 days ago, so I thought I had better get it written before I forget it. This one was shorter but again, I didn't want it to end...
    jamie50 jamie50 51-55 2 Responses May 16

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    there have been long term consequences but it happened so long ago. i was five when she punished and humiliated me, but i don't remember being humiliated as much as just hearing...
    trailsonrails trailsonrails 51-55, M May 13

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    i feel like a freak on a leash, i took my pills ( my anti depression pills) i just feel so lost. the reason why am i here bcoz i have 7yo son. my husband have my son and im alone...
    chevo chevo 31-35, F 2 Responses May 10

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    I would love to dress up and play with another crossdresser we can be *****
    twistedfrek twistedfrek 36-40, T May 17

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    Only moms know the real nightmares
    MyLady9 MyLady9 46-50, F 2 Responses May 4

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    Do you ever have those moments where you sit on the toilet seat with the lid closed down and just sob? You try to drown out the pain in ur life with the onpouring rush of tears...
    deleted deleted 26-30 1 Response May 9

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    The awkward moment when your school gives you "fun sacks" for lunch hahahaha
    fireworks1283 fireworks1283 13-15, F May 16

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    my fiance has mpd/did and we where headed out to meet some of my family she hates going out at all. but on the way this new alter popped up she said they call her brat idk but this...
    houseoutoforder houseoutoforder 36-40, M 1 Response May 10

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    Goo Goo Dolls - "Iris" And I don't want the world to see me 'Cause I don't think that they'd understand When everything's made to be broken I just want you to know who I am And...
    RoughDiamond17 RoughDiamond17 36-40, F 2 Responses May 12

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    I went home with a guy I have met a couple of times and we had fun together. There were some ahem intimate moments. based on my past experiences, men usually don't want anything to...
    Ljturn Ljturn 26-30, F 1 Response Apr 28

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    If I tell you what I hold inside would you believe, would you accept the way that I feel? Would you listen to my heart and allow me to share with you every little thing that I...
    winterfall winterfall 36-40 a week ago

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    Growing up I always wanted to have that mother-daughter relationship with my mom. I've never had that sadly. My mother has always looked out for me. She's always defended me from...
    zamxd22 zamxd22 18-21, F 5 days ago

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    I've been having these dreams lately about Keanu Reeves. I don't understand it because I usually would think of him the same as any other celebrity; just when I see their movies...
    lovenlounge lovenlounge 36-40, F 2 Responses Apr 28

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    If my mother's day card does not make my mom shed tears of joy, I'm not doing my daughterly duties! Thankfully I succeeded this year. I love my mom so much!
    Annaelaine Annaelaine 16-17, F 1 Response May 10

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    I'm a single mom with 4 kids ands I'm happy but I'm having a hard time finding a job to make ends meet. I'm analytical, driven, creative, and passionate. I was 1.5 semesters away...
    GibMore GibMore 31-35, F 4 Responses May 11

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    I wear wife's legging bra panty and top.. I ride a bike.. My wife also help me to wear those cloths..now i m wore it.
    rohitsomalkar rohitsomalkar 31-35, M 1 hr ago

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    In my early youth several older girls liked to play games and have fun at the expense of the younger kids. One day the girls asked me to play doctor with them, I knew nothing...
    ikarla ikarla 22-25 4 hrs ago

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    When I go out always use dresses or skirts (except for a few days every 28 days haha:c) I love wearing jeans and high heels,but what I love the most is feeling super girly and...
    HappyWife16 HappyWife16 18-21, F 2 Responses May 5

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    Hi. I'm a baby girl who regresses down normally to the age of about six but sometimes I'm 9-10. I'm interested in a Mommy or Daddy to message. Mommy is preferred but that doesn't...
    CottenCandyKitty CottenCandyKitty 16-17, F 1 Response May 9

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    I also wear dresses & skirts, I'm sat in hotel room, wearing red skirt, stockings and panties. Tomorrow I intend going into town and buying a LBD.
    simonsteane simonsteane 46-50, M 3 Responses a week ago