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I My Mom Knows I Am A Sissy Boy

Personal Stories, Advice, and Support 360 People

    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 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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    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 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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    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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    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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    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 56-60, M 3 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 3 Responses Jan 11, 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 16 Responses Jan 29, 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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    Related Experiences

    I believe my mom is trying to bring me down to build herself up. Im 22 years old I have a daughter who is 2 and I am 18 weeks pregnant. I have lived on my own but recently sought...
    donadeath donadeath 22-25, F 1 Response Aug 2

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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 2 days ago

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    Ok so I got pregnant at 13 by my 15 year old boyfriend .i was too scared to tell my mom (my father died) . I had unprotected sex but now I'm happy to have my daughter and she's no...
    Samantha289 Samantha289 13-15, F 59 mins ago

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    Ok so I got pregnant at 13 by my 15 year old boyfriend .i was too scared to tell my mom (my father died) . I had unprotected sex but now I'm happy to have my daughter and she's no...
    Samantha289 Samantha289 13-15, F 59 mins ago

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    He came home from working away for a short while and he always makes me so happy the moment he's back. We usually make love straight away and it's always so nice to feel that he's...
    OpenMindedGirl1 OpenMindedGirl1 31-35, F 1 Response 3 hrs ago

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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 day ago

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    I met my boyfriend at his sentencing believe it or not. I was working in the court system. Nobody should know this but we both have accepted it. He was given a two-year sentence...
    lobitalince lobitalince 31-35, F 2 Responses Aug 5

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    AN APOLOGY by Jay Hi again. It's Jay from "The Jay and Corey Show." In case you haven't noticed, I've taken down my last set of stories. I've had a realization. It takes a very...
    cumminatcha cumminatcha 13-15, M 1 Response a week ago

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    So I have been dating my boyfriend for 6months now. Before we dated I had a few conversations with him and he was so funny and polite and attractive and he played guitar which I...
    sirenaaaaaaa sirenaaaaaaa 13-15, F Aug 3

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    Alright! I have a boyfriend and we got engaged unofficially last week. But.. the problem I've faced is.. I have a friend who falls in love with me. He knows I have a boyfriend. I...
    BenzitaMckinley BenzitaMckinley 22-25, F 1 Response Aug 2

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    I got 100% Sissy on The Sissy Test, Found it on Google, now I am going to take the Inner Gender Exam or something, will goggle it and let you know my results and the name of the...
    PrettySissyBoiTG PrettySissyBoiTG 26-30, T 5 Responses Jul 21

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    DAKOTA my name is Jeremy. I'm 14 gay and I was Dakotas bf. Many don't know me because I was afraid to come out of hiding. I was raped by my mom bf and have only know pain. Dakota...
    deleted deleted 26-30 Jul 21

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    DAKOTA my name is Jeremy. I'm 14 gay and I was Dakotas bf. Many don't know me because I was afraid to come out of hiding. I was raped by my mom bf and have only know pain. Dakota...
    deleted deleted 26-30 3 Responses Jul 21

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    I am a sissy that wants to be taken and used by alpha males and turned into a sissy bimbo ****
    Sissyboitaylor Sissyboitaylor 18-21, T 7 Responses Aug 3

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    So it's been a month since my daughter's boyfriend was kicked out of his house and moved in with us. I did get the power of attorney from his mom. The kids are doing great...
    Ginger1956 Ginger1956 56-60, F 3 Responses Aug 3

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    I adore my boyfriend.... We've been together about two and ahalf weeks and although I know it's not long at all he's treated me the same as the first time we got together. We're...
    Catmando05 Catmando05 22-25, F Aug 9

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    Okay, so this pretty much is a 3 part story so ill post it 3 seperate times, but it all intertwines and stuff so yeah. And noone really knows all this except my mom and bf so im...
    Jessiesgirl98 Jessiesgirl98 16-17, F Aug 11

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    I love wearing all kinds of lingerie, and I especially like the kind that makes me feel like a sissy. I made this video when I was feeling a little sissyish. I hope you like it...
    VictoriaFredericks VictoriaFredericks 36-40, M 3 Responses Aug 12

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    LOL ex-boyfriend quote hahaha *mimics in a Mickey mouse voice* "I'm turning straight. So, you NEVER have a chance with me!" GAWD. No, I don't want to see your man-gina. Thank...
    chrisisyourfriend chrisisyourfriend 16-17, M 1 Response 1 hr ago

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    Oh my word. I can't even describe how stupid I feel posting this. My boyfriend and I have been together for 3 year and we get on so well! Like any usual relationship we have the...
    Binkyboo12 Binkyboo12 22-25 Aug 6

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    I'm a proud sissy, and I want to play. Message me. Please. You won't regret it :p
    raelynnCD raelynnCD 18-21, T 5 Responses Jul 24

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    Gosh some of those online tests are absolutely worthless! LOL But, on the few that were actually worth the time to take... I passed the Sissy Test, with flying colors!
    curiositykillz805 curiositykillz805 46-50, M Aug 12

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    how can i become some ones sissy
    gerommino gerommino 66-70, M 3 Responses Aug 13

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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 10 hrs ago

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    I'm Colin and I'm in love with Trevor. We're both 14 and going into 9th grade this fall. We have been best friends since we were 10 years old, when Trevor moved from New York to my...
    anotherkid anotherkid 13-15, M 3 days ago

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    First of all, sorry for my English, it´s not my mother language. They don´t even know how I look and hate me already I´ve been dating my boyfriend for almost two years. We meet...
    chocolola chocolola 22-25, F Jul 29

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    My mom's anger has gotten out of control, and because of it being out of control I feel I cannot trust her with her words and action when she is in this state. This of course...
    pnleg pnleg 22-25, M 2 Responses Jul 31

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    I find it extremely difficult to move on from my boyfriends past. We met while he was in the process of a divorce, and instead of doing what was right and waiting until it was...
    haileyelizabethxo haileyelizabethxo 18-21, F 1 Response Aug 8

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    My mom means the world to me but when she gets in her moods she GETS in her moods I have three brothers and I am not playing victim when I say they don't get it as bad as I do, I...
    miraguey miraguey 16-17, F 6 days ago

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    I Need Opinions: I love D to absolute death. He has become the greatest thing that has ever happened to me. D has saved me in more ways than I could ever explained. However, with...
    SgtsLittleGirl SgtsLittleGirl 22-25, F 3 Responses 5 days ago

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    any nudist breastfeeding moms wish to communicate? i am raising my 7 boys nude and free in the tropics...we home-school,co-sleep,organic gardens,sports, yoga,plays ,tree-houses...
    norma999 norma999 26-30, F 3 Responses Jul 25

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    It's AUGUST!!!!!! FINALLLLLLLLYYYYY!!! 20 days until graduation! I wasn't originally allowed to go because my mom didn't want me to travel halfway through the country by myself but...
    armygirlfriend14 armygirlfriend14 18-21, F 1 Response Aug 1

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    REAL PLEASURE WHEN MY CLASSMATE BOY WHO IS OUR NEIGHBOUR IS DISCIPLINED BY BEING CANED NAKED IN FRONT OF OUR COMMAN VARAND BY HER MOM. THIS ISWEEKEND ROUTINE AS PER...
    aashina aashina 22-25 1 day ago

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    My mother never loved me. To most outsiders, they would think she was perfect. I mean, she had four children, my youngest sister being adopted, my older brother going to Oxford...
    FullyReloaded FullyReloaded 13-15, F 1 day ago

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    I am making / decorating a box to keep all my letters and things my boyfriend sends me and I am trying to find blue camo duck tape and all I have found is green camo if anyone...
    navygirlfriend1997 navygirlfriend1997 16-17, F Jul 24

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    Honestly I don't a have a girlfriend. I just wanted to know if there's anyone I could talk to about this. You see, I'm a girl. An average girl. I have a boyfriend.. but I am not...
    RedPandaBear RedPandaBear 16-17, F 1 Response Jul 27

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    I know it sounds douchey, but whenever we leave somewhere, like a party, event, game, whatever, the first thing my boyfriend says to me is, "you were definitely the hottest one...
    RMDk RMDk 26-30, F 3 Responses Jul 29

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