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I My Mom Knows I Am A Sissy Boy

Personal Stories, Advice, and Support 345 People

    Mammy Jodie

    my friend Jodie called round the guest house on Tuesday about noon and left at half past midnight. she changed my wet nappy three times that day, once she had me lay on the dining room floor and she changed my nappy, while she was changing me any of the guests could have walked...
    Cyclopes66 Cyclopes66 51-55, M Feb 28, 2013

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    bigwickin22 bigwickin22 18-21, M Dec 30, 2013

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    Mother Aways Knew

    My Mother dressed me in my older sister hand me downs . First 5 years all i wore were tights and a top sometimes shorts when school started .My Mother cut the lace off of tops and moved the buttons to the boy side . My dad would say I 'll have Your Mom leave the Lace on if I...
    RayofSunShine55 RayofSunShine55 56-60, T 3 Responses Jan 11, 2013

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    My Mom Found My Hidden Dresses....

    I was off at school. My mom was putting a way some washed jeans. And in the bottom drawer I had stashed some of my sisters dresses,(A white one short with red and Pink flowers on it). She confronted me when I got home. She made me take them out and show her. I was so embarrassed...
    Tammy59 Tammy59 51-55, T 5 Responses Oct 21, 2012

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    Mine Knew Too

    As did my grandmother who is the one who let me know it was okay. The ironic part is I am from a fundementalist family, but they even encourage me, by buying me dresses nighties Girly dress up things and toys. I loved playing with my paper dolls. Thank you to all my family who...
    deleted deleted 26-30 3 Responses May 23, 2012

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    My Mom Know

    she knows it all she knows im a sissy she knows im in chastity im owner im in the lifestyal she sees me in panties like pink too ! she has seen my chastity cage on me ! she thinks its a goood thing she with the rest the women
    intrestinchastity1985 intrestinchastity1985 26-30, M 7 Responses Nov 28, 2012

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    Yes It's True Alright!

    Well my Mommy saw some of my female garments once although like many of you my history of cross gender dressing goes back into childhood and has even seen me dolled up in school girl uniform which for some of her other issues doesn't phaze her. It came to a head when some...
    Joanne0chan Joanne0chan 31-35 4 Responses Oct 13, 2012

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    I think my mom knew I was a sissy.

    She at least suspected it. While I was living at home, several times she found her p^nties in my room. She even saw the lines from a pair under my shorts one day. She asked to please stop wearing hers because I was thing them. She even told me that she would take me panty...
    Weakhubby Weakhubby 36-40, T 12 Responses Feb 9

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    From The Start

    from the age of five i would wear my sisters underwear even when going to school and by the age of six i stopped wearing boys underwear completely. i thought no one knew until one day my mam sat me down and told me i had to stop wearing my sisters knickers. when i said that i did...
    Cyclopes66 Cyclopes66 51-55, M 3 Responses Jan 11, 2013

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    Know ?? She Helped

    yes my mother knew she helped sis turn me sissy as a child sister didnt want yunger brother so around 4 she started dressing me mom thought it was cute and then realized it was also cheaper cuz i got sheryls 2nd hand stuff went shopping school just about anywhere sissy dressed...
    sissykrisb sissykrisb 51-55, T Mar 6, 2013

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    Yes My Mom Knows

    My Mom knew I was a sissy boy from early on ... at least by the time I was 6.  At that time my best two friends were girls and we were almost enseperable.  To make a long story short (I have already posted it before) we started dressing alike and our mothers throught it was...
    tghubby tghubby 51-55, T 15 Responses Jan 29, 2012

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    Hopefully

    my mom doesnt know that i am a sissy boy, and i know what you all are going to say, that i should get off because my mom doesnt know, but if you give me the chance i will explain through my story. i wasnt potty trained until the age of five, and after that i think that i have...
    diapeelover23 diapeelover23 18-21, M 1 Response Jun 17, 2012

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    From The Start

    from the age of five i would wear my sisters underwear even when going to school and by the age of six i stopped wearing boys underwear completely. i thought no one knew until one day my mam sat me down and told me i had to stop wearing my sisters knickers. when i said that i did...
    Cyclopes66 Cyclopes66 51-55, M Jan 6, 2013

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    Along with her lingerie,

    I would sometimes wore her shorts during warm weather. I especially liked her nylon shorts. She saw me wearing them one day and looked puzzled. Mom said "do you realize you're wearing my shorts?" I acted surprised and said I must've grabbed them by mistake. She said "ok. They...
    Weakhubby Weakhubby 36-40, T 10 Responses Apr 12

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    Ofcourse She Knows-she Made It Happen..

    I'm not going into a big story right now. If you read some my other stories you'll understand. [especially first **** sucked]. She must have planned it out very early. I can't remember a time as a little boy when she didn't like to dress my sister and myself alike. Most of the...
    2647Cindy 2647Cindy 56-60, M 25 Responses Dec 17, 2011

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    Mom Made Me

    My mom used to be a dancer and now she is a beautician and part time make-up artists. I have always been very androgynous and more femme and loved to play dress up with her things. I knew it was something naughty and so i tried to hide it but it was only a question of time until...
    angelictom angelictom 18-21, M 2 Responses Apr 18, 2012

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    i was 16.it was about 10 O' clock.

    Mother and evry sister was a sleep. There was some of my sisters panties and bras i took on cotton lace blue panty and matching blue color bra i put on them it was so comfortable i felt so free like a bird i wear underwears but there not that much satisfying like this so i want...
    binurakink binurakink 22-25, M 8 Responses Jan 8

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    Everyone Knew

    My mother worked to keep my sissy side within the house away from public view. It was a secret we shared.I felt safe with her knowing full well she was protecting me from my father & older brothers. A classmate in school, however, had an entirely different experience growing up...
    janusatv janusatv 61-65, T 2 Responses Oct 24, 2012

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    I love my mom, she has always been very

    supportive of me, even though it has cost her a lot through the years... We sort of made the decision to embrace my feelings together, I think she preferred a daughter to a son anyway... Once we decided to be honest about my reality we formed a tighter bond I think... Thanks...
    deleted deleted 26-30 2 Responses Feb 3

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    Mother'S Always Know

    Mothers seem to always know about these things. Bobby's mother and sister always wanted all girls, so they dressed him in dresses from age 8 till he graduated. He didn't know any other way to dress. Even as he got older and knew other boys dressed different, he then still wanted...
    jennylee911 jennylee911 36-40, F 2 Responses Feb 24, 2013

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    Mom And Granny Knew

    My mom and grandmother knew I was a sissy and they honored and embraced it with me, by buying me Girly dresses panties nighties dolls. Granny had tea parties with me. We always wore gloves. I had little play high heels but never had maryjanes.
    Phxpaulena Phxpaulena 61-65, M 5 Responses Apr 12, 2013

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