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I My Mom Knows I Am A Sissy Boy

Personal Stories, Advice, and Support 366 People

    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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    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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    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 4 Responses Apr 12, 2013

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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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    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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    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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    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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    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 5 Responses Jan 11, 2013

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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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    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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    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 16 Responses Jan 29, 2012

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    Hello my name is Jenny and my Ex boyfriend, his name is Bobby,......has wore all my clothes, well at least all my dresses and lingerie. I know it sounds so yucky, but as he grew up...
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    Result Yes!!!!!!!!!! Terribly sorry but you are in fact a sissy. Because you are a sissy you have the right to cry now. SISSY!!!
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    Well, I can't decide if he's an idiot, a scumbag, or both. He's probably both. Intentional or not, his six-month rampage of inexcusable douchebaggery is coming to an end after...
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    I think I'm becoming a sissy, well a sissy slave
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    ...but there are so many things that bother me about them. I'm currently 18, my boyfriend is 21. I moved in with my boyfriend and his family (his mom, two brothers, and two sisters...
    lostinparadisee lostinparadisee 18-21, F 4 days ago

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    so me and my boyfriend have been dating for almost a year now and his mom (and grandma) don't like me AT ALL. at first she was nice to me, she would always tell me how pretty I...
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    I just feel so sad because I want to have a good relationship with her but it is just so hard.. The other day my boyfriend asked me what memories I had of my childhood with my mom...
    roomii roomii 18-21, F 2 days ago

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    This is not the way it was supposed to go. I'm Rosalind (21 years old) and I have been with my boyfriend Benvolio (22 years old) for 6 months. Not incredibly long of a...
    ReservedRosalind ReservedRosalind 18-21, F 16 hrs ago

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    I have just started writing a new blog chronicling the slow feminization and sissification of my partner by myself. This blog is not a work of fiction, nor is it in any way the...
    deleted deleted 26-30 3 Responses Sep 5

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    I have just started writing a new blog chronicling the slow feminization and sissification of my partner by myself. This blog is not a work of fiction, nor is it in any way the...
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    deleted deleted 26-30 1 Response Sep 5

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    I wish I had the body of a girl. I am meant to be a girl. Even as a boy dressed in women's clothing I look like a girl from the neck down. I have a vagina envy and would do...
    sexysissy11 sexysissy11 18-21, M 1 Response Sep 11

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    Today I am dressed as a sissy maid. I will clean the house from top to bottom. Unfortunately, no one cares.
    letmespoo4u letmespoo4u 51-55, M 7 Responses Sep 2

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    My mom gets me, she says. But she never even listens to what I have to say. I'm always wrong and she always knows better, since she's been through a lot. A life where her mother...
    Sourminds Sourminds 18-21, F Sep 5

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    ... she hurts me all of the time, even if she doesn't realize she's doing it. My family isn't poor, but we know what it's like to have too much month left at the end of the money...
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