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I My Mom Knows I Am A Sissy Boy

Personal Stories, Advice, and Support 365 People

    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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    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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    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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    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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    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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    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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    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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    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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    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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    Related Experiences

    My boyfriends father and brother just left to go on a camping trip. It's 8am. I arrived here at 7 cause I spend Friday-Sunday at his house. I usually don't come over until the...
    sugarcakes143 sugarcakes143 18-21, F 2 Responses Aug 29

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    My boo is upset. I wish I could be with him right now to help him, but for now I can only text him. I can only try and make him happy and give him advice. He's having boy...
    CallMeChelsea CallMeChelsea 16-17, F 1 Response Aug 18

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    My boyfriend and I are very comfortable with each other. He watches ****, I watch ****... We are both totally okay with this... Sometimes we watch **** together... Lesbian ****. I...
    SecretlyBiRightNow SecretlyBiRightNow 16-17, F 4 hrs ago

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    Hi guys my last relationship of two years with my ex still follows me on Instagram, It's getting to the ridiculous point of him with a case of 'the green eyed monster' as I can...
    jaexo jaexo 18-21, F 1 Response 14 hrs ago

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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...
    jennylee911 jennylee911 46-50, F 1 Response 6 days ago

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    You Tell Me I can understand why some of my friends think I'm girly or even gay (which I am, but they don't need to know right? ^^; ). I’ll just compare myself to most of the...
    noahman97 noahman97 16-17, M 2 Responses Aug 25

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    Yesterday was the fist day i spent with by master. I loved being all dressed up in really cute sissy clothes (he even made me lock my boy **** in a cage) and he made me service...
    bottomslut1 bottomslut1 18-21, M 1 Response Aug 19

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    Bobby and the girl at a friends birthday party Britney and Kathleen took me to a friends birthday party Saturday. I wore a printed knee length dress with a short net petticoat...
    bobbylee111 bobbylee111 36-40, T Aug 23

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    You Tell Me I can understand why some of my friends think I'm girly or even gay (which I am, but they don't need to know right? ^^; ). I’ll just compare myself to most of the...
    noahman97 noahman97 16-17, M 2 Responses Aug 24

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    You Tell Me I can understand why some of my friends think I'm girly or even gay (which I am, but they don't need to know right? ^^; ). I’ll just compare myself to most of the...
    noahman97 noahman97 16-17, M 1 Response Aug 24

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    Sissy white boy. All I do is crave c*ck
    raelynnCD raelynnCD 22-25, T 2 Responses Aug 25

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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!!!
    CdKimmi CdKimmi 61-65, M 3 days ago

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    I'm not Sure I took a Sissy quiz on a site called ProProfs and when I submitted it my results said... ??? I'm sorry. But this test was for men only not girls. So...did I pass...
    noahman97 noahman97 16-17, M 1 Response Aug 26

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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...
    floyd228 floyd228 22-25 Sep 3

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    I think I'm becoming a sissy, well a sissy slave
    giantsword18 giantsword18 13-15, M 2 Responses a week 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...
    lundenxo lundenxo 18-21, F 1 Response Sep 5

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    Hey guys! Just figured I would give this a try. If anyone wants to message me on here, been looking for a boyfriend for about 8 months with no luck. If you want to chat I'm not...
    Rocker1188 Rocker1188 22-25, M 1 hr ago

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    My Friends Say I Do Pretty much all of my friends at school and my friends online say I'm kind of sissy-ish. I HATE touching gooey stuff, like ketchup when washing dishes and...
    noahman97 noahman97 16-17, M 8 Responses Aug 23

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    I am 16 years old. My mom, has been married and divorced 3 times. She went to prison for 3 years. She came back from prison, left my stepdad, and is now in an ongoing relationship...
    wootenbrittany7 wootenbrittany7 22-25, F Aug 25

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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...
    deleted deleted 26-30 2 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...
    deleted deleted 26-30 1 Response Sep 5

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    My boyfriend and I spend a healthy amount of time together, our families are close, we have a great bond and are very open. I am his first serious relationship, and there is one...
    classic00 classic00 18-21, F Sep 6

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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 a week ago

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    That moment when you tell a guy that youll ride him and take every inch before you even know how big he is. Then pull down his pants and realize that he's over 10 inches. But he...
    bottomslut1 bottomslut1 18-21, M Aug 22

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    I am trying to find a way to be noticed as a sissy by women, last night I went out back to a main road, and I wore just panties and shoes, and stood by the road, so many cars drove...
    sissyslut4training19 sissyslut4training19 18-21, M 2 Responses Aug 20

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    I'd never do this in real life, it's just a fantasy of mine. I'm a 100% straight guy but at night the thought of being blackmailed and turned into a sissy boi is one of my biggest...
    NightlockForever NightlockForever 13-15, M 3 Responses Aug 23

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    hi im a 18 yr old sissy that loves to crossdress and turn all girly and naughty, i love being demanded to do things and i am looking for a mistress who can take care off me i can...
    stranger123456 stranger123456 18-21 2 Responses Aug 26

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    One day my wife asked me to compare myself to this list of things and check {!} which ones apply to me. 1.Not afraid to show your emotions, like crying in public. ! 2.Embrace...
    CdKimmi CdKimmi 61-65, M Aug 27

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    I love wearing sissy lingerie and my wife buys my lingerie
    rimonty59 rimonty59 51-55, M 6 Responses Aug 30

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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 6 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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    Call me CJ. It's short for Christopher John. I'm 15 years old. I'm in 10th grade. I'm from the great state of Alabama, my sweet home. In public, I'm totally straight. I have a...
    cjfrombama cjfrombama 13-15, M 1 Response Sep 7

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    My wife and I were strolling the boardwalk in Wildwood, NJ and I had been pestering her for years to get both of her body parts, EP Nazi's says can't use the top of a baby bottle...
    CdKimmi CdKimmi 61-65, M 3 days ago

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    Okay, so I have no problem what so ever with my boyfriend having a child with another woman, as a matter of fact I love his daughter as much as I love my own baby to be! I just...
    danielleLaB0 danielleLaB0 18-21, F Aug 27

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    I guess ever since I could remember I've hated my mom, always day dreaming about a mom that cared and loved me. I am now 15, and I can't even remember the last time my mother said...
    Jaaye1 Jaaye1 70+ 1 Response Aug 31

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    I sometimes feel like she doesn't love me as much as I love her. She is basically having an affair and I support her in it seeing as her husband is a complete douche. Well he found...
    lookingtovent lookingtovent 16-17, F 1 Response Sep 5

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