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

Personal Stories, Advice, and Support 376 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...
    deleted deleted 26-30 7 Responses Apr 1, 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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    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 18-21, M 3 Responses Jul 15, 2013

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    puppydoglover puppydoglover 13-15, M 4 Responses Jan 21

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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 18 Responses Aug 3, 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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    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 advancing upon her new smocked Viyella dress with a large pair of scissors. By four, she was standing at the gate of our country cottage...
    janecool janecool 16-17, M 2 Responses Jan 25

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    Related Experiences

    my mom is ******* crazy. she is saying that because the neighbors next door park on the certian part of street they are stalking her and want to rape her. keep I'm mind she is a...
    abe15 abe15 18-21, M 15 mins ago

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    Trying to kiss my ex's mom yeah
    Johnnycashh Johnnycashh 22-25, M 1 day ago

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    Yesterday was a good day for me and a bad one too. Good day: I invited my daughters over for a taco dinner night. Just a time to be with them and converse. Had a great meal and...
    shadowplt shadowplt 51-55, T 5 Responses 2 days ago

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M 3 days ago

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M 1 Response 3 days ago

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M 3 days ago

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M 3 days ago

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M 3 days ago

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    My stranger for a Mother has refused to pay my bills once again. I have a $2000 bill to pay. The only reason that I ran it up was because I was working, but my stranger for a...
    ONESTARRYSTARRYNIGHT ONESTARRYSTARRYNIGHT 26-30, F 3 days ago

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    Hi everyone!! So. It's been a good couple of years since I've been on here.... I haven't even thought about this site for a while until I had an experience to share! Now. The last...
    theJagermeister theJagermeister 18-21, F 6 days ago

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    I was looking forward to eating just one chocolate dipped strawberry and my mom bought me my own little kit!! The chocolate was $3 and the strawberries were $5... I was so grateful...
    Maricopa Maricopa 18-21 1 Response Jan 27

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    I love to look up women's dresses and skirts. Yes ladies I am that guy that purposely sits across from you so I can see all your sweet delicious goodies between your legs. I...
    snoop81 snoop81 31-35, M 1 Response Jan 27

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    I feel incredibly lost today in my own mind. Which is a horrible feeling. My own thoughts contradict eachother from one moment to the next. Maybe I can sleep it off?
    Rosamarie1897 Rosamarie1897 18-21, F 3 Responses Jan 26

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    I am so bad that my kids text me please don't pull up playing Rakim or Biggie!! They know their mom loves her music turned up to the max! When I drive its TURN Up time!! Especially...
    MzMecka1969 MzMecka1969 46-50, F 1 Response Jan 26

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    THA AGRAWAL - 5:46 AM CROSSDRESSING STORY Hey! As this is my first story, I would like to narrate my own story as best as possible. Any sort of feedback/suggestions related to...
    janecool janecool 16-17, M 1 Response Jan 26

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    idk it seems like I have two different personalities. There's the confident, cool, outgoing me with the dramatic, sarcastic flair and the sassy eyebrows then there's the lonely...
    bigMamaY bigMamaY 13-15 1 Response Jan 25

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    It were some of the best days of my life. My older sister Lily, would always complain to my parents that she wanted a baby sister. She wanted someone to share her girl toys with...
    TimMatthews TimMatthews 18-21, M 3 Responses Jan 25

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    so i really don't like being a room alone with older men. it scares me. when i was little I'd dress in layers all the time no matter what weather I'm in, it'll be extremely hot and...
    funkittyful funkittyful 18-21, F 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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    I'm snowed in where I live, so I only got dressed long enough to give my children (two boys, ages 6 and 4) a chance to play in the snow. Tomorrow, I'll be digging out from all of...
    BLACKTIGER75 BLACKTIGER75 36-40, M 6 Responses Jan 23

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    If I'm on my own, who cares what I put on?
    FurryElephant FurryElephant 36-40, F 4 Responses Jan 23

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    So...I was looking through some family and friend photos just now... And wow...I'm terrible! I have no idea what to do with myself in order to look like a girl. I mean, I don't...
    WritingDesk11 WritingDesk11 22-25, F 2 Responses Jan 23

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    But then, who is? It's very rare to find anyone who actually gets to where they wanted to go by this point. No reason to moan about it, though. When I was a little kid I'd imagine...
    HuntressX23 HuntressX23 16-17, F 1 Response Jan 22

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    An imaginary parallel world i guess thats the only solace ......haha its not even real yet makes reality bit .... A bit bearable or may be not every new moment i shatter and then...
    anasteel2 anasteel2 41-45, F Jan 22

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    I've been 5'0" since I was in sixth grade. I have a small body and I'm thin (I get picked on for being thin a lit in school). My two best friends are 5'4 and 6ft. I wish I was...
    StephAndrea StephAndrea 13-15, F 1 Response Jan 21

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    Shhhh don't tells Mommy or Daddy :3 I'm not posed to be ups right nows
    Daddydomless Daddydomless 22-25, F 2 Responses Jan 21

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    I'm a 15 year old sissyboy I secretly wear my 17 year old sisters cloths tank tops bra panties lingerie dresses gowns bikini tights leggings yoga pants skirts and definitely make...
    deleted deleted 26-30 Jan 20

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    I feel that my first impression on people is always someone who's generally nice, pretty cool and easy to talk to.. which all in all, it's pretty dead on. However, I have to say, I...
    Dereth Dereth 26-30, M Jan 19

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    I have always been a girly girl and I've always enjoyed being a girl. I prefer to wear dresses or skirts instead of t shirts and jeans and I like putting on makeup and lipstick. I...
    youngandenergetic youngandenergetic 13-15, F 2 Responses Jan 18

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    Nothing but underwear, Netflix/Hulu and chill.
    BellyBoySL BellyBoySL 22-25, M Jan 18

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    I've not been leaving my usual daily messages on friends whiteboards.. Time has not been my friend the last few days.... I've got my wife's mother in hospital at the moment...
    expressomarkie expressomarkie 46-50, M 3 Responses Jan 18

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    I M CROSS DRESSER GUY AND I M LOOKING FOR A NICE TOP GUY..
    deleted deleted 26-30 1 Response Jan 17

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    just like today.....football and pj's.....that is all :)
    PrettyAsaFlower1972 PrettyAsaFlower1972 41-45, F 9 Responses Jan 17

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    but I have been going all day
    itsBob itsBob 51-55, M 1 Response Jan 17