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I My Mom Knows I Am A Sissy Boy

Personal Stories, Advice, and Support 354 People

    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 2 Responses Jan 11, 2013

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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 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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    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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    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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    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 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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    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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    Related Experiences

    I believe you are who you see you're self as and if that's a women even tho you're a man who the **** saids ? Religion ? Pfffft **** that be who ya want even if it does mean you...
    kerw94 kerw94 18-21, M 4 Responses Jul 7

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    Would love to meet a cool guy who was Dom and into a Sub Sissy Boi!
    PrettySissyBoiTG PrettySissyBoiTG 26-30, T 1 Response Jul 15

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    Yeah I won't lie I'm down so where's this room at ??
    kerw94 kerw94 18-21, M 1 Response Jul 7

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    Would love too! Anyone in ontario? Feel free to add and message me!
    jack4770 jack4770 18-21, T 2 Responses Jul 9

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    This is what I would truly love to find at some point!!!!!
    PrettySissyBoiTG PrettySissyBoiTG 26-30, T 2 Responses Jul 12

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    I hate it when my mom has a boyfriend. She's always loving on him and putting him first. She acts like me and my sister don't even exist sometimes. When he's around she ignores us...
    KylieWise19 KylieWise19 22-25, F 1 Response Jul 13

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    I really really dislike my step mom.... she's ALWAYS getting mad and starting fights with me and my older sister for the stupidest things. For example: forgetting to pick up a...
    hellobriannaskye hellobriannaskye 13-15, F Jul 20

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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 7 hrs ago

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    There are moments in life when you just know. When you know you've made the right decision, when you know you've done something to benefit yourself. I've been holding back for...
    PrincessKayleigh PrincessKayleigh 16-17, F 6 hrs ago

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    When I was nine years old, my mom needed time to "get back on her feet." She dropped me off at her friend's family in a small town, and fled to the city. She promised she would be...
    Levi1 Levi1 13-15, M 9 Responses Jul 14

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    i think it will be fun to have a online mom and dad.... i can share things and talk to them about which i cant talk to my real mom n dad If anyone interested to become a mom or...
    kinkprime kinkprime 22-25, M 1 Response 14 hrs ago

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    My mom was a terrible person. I've already covered that she was an alcoholic and she has bipolar borderline disorder. But there is so much more to it. She blamed me for the sexual...
    Xander8905 Xander8905 18-21, M 1 Response Jul 19

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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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    Let my start off by saying that I'm a Christian and I am gay. I live with both my parents and my younger brother and I have a dog. I've been dating a guy for the past 2 months. We...
    jowaymedina jowaymedina 13-15, M 3 Responses Jul 3

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    I love being a sissy, even more than that I love playing with others. There's nothing better than licking down someone and ripping a hole in some nylon stockings thirsty for her...
    raelynnCD raelynnCD 18-21, T Jul 19

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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 2 Responses Jul 21

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    So, I already posted this story before but in another Teen Mom comunity, but I decided to post it here too. Just saying because maybe you've read it before? haha idk When I was 15...
    VioletandCaleb VioletandCaleb 16-17, F Jul 11

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    I'm 16 with a 4 months old daughter So, I already posted this story before but in another Teen Mom comunity, but I decided to post it here too. Just saying because maybe you've...
    VioletandCaleb VioletandCaleb 16-17, F Jul 11

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    When I grew up I did at least in private and sometimes not so private wear short pleated skirts and the occasional pinafore style dress. This was not a punishment and indeed I am...
    littlegreyshorts littlegreyshorts 51-55, M 2 Responses 14 hrs ago

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    It is said that we should love our parents. Mother is uniqe. Only one of her kind. But my mother is a person who hurt me the most in life. Because of her i've been crying the most...
    viktorija99 viktorija99 16-17, F Jul 1

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    I was 16 when i found out i was pregnant, & gave birth to my son when i was 17. We were friends for 7 years & one night it jusd happened, no sign of me been pregnant until one day...
    taawhakismummy taawhakismummy 18-21, F Jul 13

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    He hates all the "hallmark" crap but I honestly don't know where I'd be with out him. He knows what I'm thinking all the time and as much as I act like it annoys me it actually...
    YimYam YimYam 18-21, F Jul 14

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    My mom cheated on my dad😥now I hate her so much ill do anything to try and disagree or **** her off! Just so she can get a taste of her own medicine. Sometime I REALLY consider...
    kat99rebal kat99rebal 13-15, F 1 Response 17 hrs ago

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    I have been a stay at home Mom for most of my children's lives. Their lives are my focus. Now that they are almost all out of the home, I wonder what my new path will be...
    bunnigirl bunnigirl 46-50, F 2 Responses 10 hrs ago

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    This was the closest "experience" I could find that I could relate to in a way. Now, I'm not pointing any fingers or accusing him of cheating...I just feel like something has...
    supernovaChic supernovaChic 22-25, F 2 Responses Jul 9

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    First, I hate that term "step-mom", no matter how you say it, it always sounds negative. I have known my fiancé and his son for almost 7 years, and we have been "together" for the...
    annewiora annewiora 26-30 Jul 11

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    COMING OUT - A Story by Jay. Hello, everyone. It's Jay from the "Jay and Corey Show." For those of you who have been around EP for a while, you probably know us. For those of you...
    cumminatcha cumminatcha 13-15, M 2 Responses Jul 20

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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 2 Responses a week ago

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    I raise my 7 boys,NUDE IN NATURE 34-7...am a lactation consultant,womens advocate,nutritionist,herbalist we homeschool,co-sleep I BREASTFEED all 7 of my boys,as breasts are for...
    norma999 norma999 26-30, F 4 Responses Jul 3

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    Hello 😊 Not sure if I really count as a teen mom since I had my son at 19 but I feel like I fit in more here. Ok so my name is Hailey and last year I got pregnant straight out...
    haileyara23 haileyara23 18-21, F 4 Responses Jul 7

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    Hi. I could really use conversation from people who are going through possibly a similar situation as me. I broke up with my amazing, beautiful person of a boyfriend 2 days ago and...
    ChelseyBrownfield ChelseyBrownfield 22-25, F Jul 14

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    15 and never had a boyfriend but what ever 😁👌
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    In august of 2012 I started dating my boyfriend, and in October of the same year (just 3 months into our relationship) he was arrested and served 3 months in jail, it was one of...
    ambv ambv 18-21, F 4 Responses 14 hrs ago

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    Finny5 Finny5 26-30, F 5 Responses Jul 7

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