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I Am a Sissy Boy

Personal Stories, Advice, and Support 2,328 People

    Total Submission

    He's big and intimidating as he lets me into his apartment.  Sitting down he just stares at me not saying anything, I begin to feel uncomfortable then realise I should be taking off my clothes.  Soon I am standing in front of him in my chemise and panties and my **** is so hard...
    smiteenyb smiteenyb 56-60, M 3 Responses May 21, 2012

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    Cali Sissy Available for training

    hey~ im a sissy looking to be dominated. i recently accepted that im a girl at heat, but would like to feel the part~. i want to dress up all skimpy for my master/ mistres and prance around for there enjoyment. i want to be your *****~ ok? ;) im 22 white with a young petite body...
    yoursissyboy yoursissyboy 22-25, T Jun 14, 2013

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    He Is Adorable As A Little Girl

    My 8 yr old son doesnt mind me sissying him and he makes an adorable little girl. When he is dressed up its as if he is a toddler, more like  a 3 yr old over again. He happily stands and allows me to take his shorts off him, holding my shoulders then he coyly covers himself...
    louise37 louise37 36-40 26 Responses Nov 13, 2011

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    My First Time

    my first time with a guy was when i was 17, and i was coming back from a club one night a little bit tipsy but i looked good i went all out that night stockings heels and a dress that was way to short and the way i was coming home that night i took this short cut through a park...
    jesslovecock jesslovecock 18-21, T 1 Response May 8, 2013

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    My Story Ahead..

    I had moved in with my butch cousin sister when I was 20. I am a sissy boy since I was 17.. I realised that my penis had no meaning as I dont have any use of it anymore.. It has been locked away in a chastity belt since 3 years now.. My sister is my husband and I am her housewife...
    Simkalr Simkalr 22-25, T 1 Response Jan 12, 2013

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    Dressed As A Ballerina

    I met a guy a couple of years ago through ballet. He wasn't in my school but we met through a summer intensive course. As we were the only guys in the course, we started becoming friend. He was very handsome and funny. I was not sure at first if he was gay as he seemed to be...
    danseuretoile danseuretoile 31-35, M 6 Responses Aug 18, 2012

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    One Time With A Guy Now I Want To Be A Sissy ****

    When i was 17 i was drinking with a guy who was gay as i got drunk he started stroking my inner thighs it made me hard ,i told him to stop he put his hand on my **** and started stroking it through my trousers ,he tried to kiss me i pulled away he was looking at the bulge in my...
    artycampbell artycampbell 51-55, M 10 Responses Dec 9, 2012

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    Moms Little Girl

    when i was born my mom gave me a name that is useally a girls, an while i was growing up she would dress me as a little girl when my dad was out of town, at 12 i made a good looking girl but the nxt yr i started to fill out an my voice got very low but even now i like to cross...
    jackson38 jackson38 70+, M Apr 9, 2013

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    Sarah was Humiliated in Front of Her Best Friend and her Boyfriend

    I got myself into trouble the other day. I live on the second floor in a little apartment building. I was just starting up the stairs when I looked up and saw that my neighbors were out on the landing. She had her back to the railing and was talking to her boyfriend. She was...
    SarahCD707 SarahCD707 51-55, M 2 Responses Aug 21, 2012

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    sammi11 sammi11 41-45, T 6 Responses Dec 19, 2012

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    Hubby's Sissy School Friend....

    Victor was Hubby's sissy school friend. Hubby had told me many stories about how the guys and gals had humiliated Victor in school and how he loved that. Victor happened to come to our place to stay for a few days. Hubby remembered the good old days and we decided to enjoy his...
    vanit vanit 26-30, F 9 Responses Jan 28, 2013

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    Sissy Boy In Need Of Help

    I am a sissy boy who needs training. I have all the skills. I love wearing cute little outfits,and catering to a dominate female's every desire. i have never sucked **** or been ****** up the *** but would love a girl to do it to me Please take me as your submissive sissy boy!
    mrmike554 mrmike554 18-21, M 1 Response Sep 26, 2013

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    Isn'T The Same Old Story?

    Around age 12, I discovered that seeing, feeling, even thinking about panties and bras made me feel.....different. My chest felt hollow and i experienced a strirring "down there" that I had never felt before. That, of course, led to late night forays into the laundry room to...
    JanM38 JanM38 51-55, T 3 Responses Feb 7, 2013

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    Sarah's Tennis Fantasy

    Normally I talk about real things that have happened to me but this is a pure fantasy. I wish I could play tennis ..... (fantasy number one). I am useless with any ball sport. .... wearing a short pleated white shirt and white frilly panties. Panties with lots of ruffle and a...
    SarahCD707 SarahCD707 51-55, M 4 Responses Aug 22, 2012

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    I am definitely becoming more fem every day.

    Over the past two weeks, I've purchased several women's tops. Last week, I went out wearing a women's top with jeans and makeup. When the women at starbucks handed me my iced coffee, she called me hun :)
    Lilly292 Lilly292 41-45 1 Response Oct 6

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    I Was

    I was abused, also by a uncle, at 9 yo, but I loved it. He shows me how to do a blow job. I was his girl until he died, I was 20.He wasn´t the first one, whem I was 6 yo, an older boy in his 13, ****** my *** to lend me his bike. He did it in front of many others boys, and of...
    deleted deleted 26-30 Apr 12, 2013

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    Sarah Being Naughty

    PART 3 We had agreed on some basic ground rules before I arrived, legal, safe, consensual etc but we had not created a detailed script and so as I opened the bedroom door I had no idea what to expect, what I saw took my breath away. Laid out on the bad were a pair of sheer black...
    SarahCD707 SarahCD707 51-55, M Aug 16, 2012

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    Sissy Needs A Mentor

    I have been a closet crossdresser sissy since I was a teenager. I am usually Dom but I have a lot of sub fantasies that I'd love to explore. I prefer playing with women but will entertain select men. Hoping to find someone to help me. I have many fantasies and fetishes but the...
    jenncd41 jenncd41 46-50, M 1 Response Oct 3, 2013

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    my sister dress me like her baby sister with a

    yellow dress and red nail polish
    jskem jskem 61-65, T 2 Responses Feb 27

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    Got Started With My Friend

    I got started being a sissy while playing boy friend girlfriend with my friend..at first i thought it was all a game but he kept pushign it further. an i found my self being kissed me all naked him in his pjs and his big **** in my hand ******* himwhlie he played with me down...
    pinkbabysnowboi pinkbabysnowboi 18-21 21 Responses Jan 10, 2011

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    He Loves Being A Mommys Boy

    My son is almost nine yrs old and I started dressing him as a little girl almost 3 months ago, mostly just after school and for bedtime. It started after he had stayed with my sister and she had dressed him as a girl to put him to bed. I asked him how he felt being dressed as...
    emilies emilies 36-40 19 Responses Apr 3, 2011

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    Releasing The Sissy Inside

    It started when I was a child. I was attracted to the things that girls wore. I eventually began to seek into my mom's room and take things from her closet to wear. I discovered that I loved wearing dresses and skirts and heels. I was confused aout it all because I was a boy and...
    Ebonysissy Ebonysissy 56-60, F 1 Response Apr 3, 2013

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    Chubby Sissy

    I was always alittle over weight and on the chubby side, When I was 11 years old my mother was at her wits end with my being heavy and told me that I should be ashamed of how I looked, how I had larger breasts then either her or my 16 year old sister. She told me that until i...
    rogume01 rogume01 46-50 3 Responses Jul 18, 2013

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    French Maid

    I used to be active in the AOL Crossdressing chat rooms. One day I was looking for something a little more than talk and so I asked for a "live" meeting. Someone contacted me and after some IMs and then a phone call, I agreed to go over to their place. It was a couple living...
    SarahCD707 SarahCD707 51-55, M 2 Responses Aug 15, 2012

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    "Sissies Who Love To Play With Other

    Sissies" This is excerpted (and edited a little) from the real exchange of messages between Sissy "S" (i am protecting her identity) and me. I bet that other sissies would like to play the same way or in similar ways. Note: spellings have had to be changed so as to not violate...
    kent1973 kent1973 56-60, M Mar 11

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    Sometimes Others Know Us Better Than We Know Ourselves.

    All my life, as far back as i could recall...everyone had always told me i was far too pretty to be a boy. When i was 6...my aunt became my legal guardian, as was the case for my older brother and two younger sisters. I remember the first time she ever dressed me as a girl. It...
    JesseWenchester JesseWenchester 22-25 2 Responses Apr 8, 2011

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    How I Became a Sissyboy

    My neighbor used to give me backrubs and his hands would occasionally move toward my crotch.  This made me uncomfortable at first, and then I longed for it.  Finally, I went over to his house and have sex with him.  It was my first time with a man and we did...
    Vicky333 Vicky333 41-45, M 10 Responses Jul 23, 2009

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    The Sissy Boy Underneath

    For all intents and purposes, to the outside world, I am a regular man. A real man. Some would even say I am a manly man. However, underneath the manly exterior, lurks a sissy. I even have a sissy name to which I answer: Cissy. I am fascinated by the idea of being kept in...
    lapsode lapsode 22-25, M 1 Response Apr 10, 2013

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    Best Day Ever!!!

    Hi, my names mike... I'm 18now, but at the time, I was 15. It started out when my neighbours moved next door. The husband, was a 50 year old hunky man that gave my a ***** every time I saw him... I was crazy!! I knew something had to be done... So one day, I put on some of my...
    Mikereedhd Mikereedhd 18-21, M 1 Response Apr 16, 2013

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    Always Love Sissy Boyss

    hey people i love sissy boys i wud wanna a sexy sissyboys here mucks
    blucarisma blucarisma 26-30 Nov 13, 2013

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    Cross Dressing.

    Hi everyone, I am a sissy boy, I love to wear the most feminine clothes I can get my hands on. I particularly love silky night dresses, one piece swim suites and stockings. I have been dressing up for as long as I can remember, but have never had the courage to share this with...
    throb42 throb42 41-45, M 8 Responses Mar 28, 2012

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    Hey :)

    Someone talk to meeeeeee!xx xoxo
    Sissygurlxx Sissygurlxx 18-21 3 Responses Oct 19, 2013

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    Wifes Sissy

    The last time my wife walked out wearing black panties and nightgown. She had this look and a hairbrush in her hand. Come here little boy I have some thing for you. Into the bedroom we went. On the bed were white panties and a schoolgirl dress. She made me undress, started...
    overthekneeplease overthekneeplease 41-45 6 Responses Jun 15, 2009

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    Page Boy Outfit

    I would like to share my experience of being a page boy for the wedding of my auntie when I was about 8. My mum suggested I was going to be a page boy and my sister one of the flowers girl. I was thrilled because I loved dressing up and going to parties. I was already a bit of a...
    danseuretoile danseuretoile 31-35, M 4 Responses Oct 24, 2012

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    Turned Out

    i snuck in to an adult arcade and theater when i was 15teen it was dark and the guy at the counter seem to not care. I got back to where the booths were. My eyes had not a jested to the darkness there was enough light for me to watch a black guy drop his shorts with no briefs on...
    BillieWill4U BillieWill4U 18-21, M 5 Responses Oct 29, 2011

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    Me Too

    I love wearing lingerie, dresses and make up. I finally got a boyfriend, and he is training me to be submissive buy keeping me in a Birdlock Chastity trainer. To show im obedient i keep a small glass butt plug in all the time, and he's had my nipples peirced and capped with...
    HayleySissy HayleySissy 22-25 Mar 20, 2013

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    I Am A Sissy Boy Who Needs Training

    I am a sissy boy who needs training. I have all the skills. I love wearing cute little outfits, sucking ****, being ****** in the ***, and catering to a dominate female's every desire. Please take me as your submissive sissy boy!
    lazyzach2010 lazyzach2010 22-25, M 1 Response Apr 17, 2013

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    My Little Sissy ****

    I kinda always new I was small dicked sissy boy. Even though small, my little pee pee has always been my best friend. She has always given me pleasure and now being middle aged and a little wiser I look back and realize how it has shaped my life. Growing up as a cross dresser...
    joann4urplsur joann4urplsur 56-60, T 2 Responses Apr 2, 2013

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    My Sissy Boy/girl Experience

    In my early teens my older sister caught me trying on her clothes. It wasn't the first time I wore her or my moms clothes. When I was dressed I felt so happy and content. My sister teased me at first and made me cry. I guess she realized then how important it was to me. We talked...
    deleted deleted 26-30 1 Response Aug 22, 2010

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    My Training

    My wife my Princess has been training me slowly for Years to be her sissy cuckold. I had no idea it was happening until it was to late, she took the **** that she wanted, there was nothing i could do. I was angry and hurt but at the same time it drove my sexual arousal to...
    cameltoepanties cameltoepanties 36-40, M 11 Responses May 26, 2012

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    I'm A Sissy Boy

    I'm a sissy boy who likes to be shaved smooth and dressed as a girl. While dressed as a girl, I love to be a sexual object to men. I like it when they reach their masculine hand up under my skirt and feel my smooth sexy panties. Of course I am always shaved smooth and ready to...
    karenjensencd karenjensencd 41-45, T 2 Responses Oct 27, 2013

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    Help Me?

    Can anyone give me the link or name of the story where the sissy boy bounds himself and has a pocket ***** but loses the key im not a sissy but by far that is 1 of my favorite stories and I can't find it anymore :C
    imyourguy imyourguy 18-21, M Nov 5, 2013

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    No

    Hi im not a sissy but I love them if any sissys would like to chat message my kik its _whos_in_charge
    imyourguy imyourguy 18-21, M Nov 23, 2013

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    Son Still In A Nappy At 7

    Im writing to support some of the other mums that dress up their boys as little girls. My son is almost 8 yrs old and after he gets a bath, gets into some little girls pjs then at bedtime he has a nappy on for the night. At first  he was reluctant to allow me to put him in it...
    samantha222 samantha222 31-35 9 Responses Nov 17, 2011

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    This Site Is Awesome

    http://www.dolldivine.com/
    AnonymityDarkstone AnonymityDarkstone 31-35, T May 19, 2013

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    Stockings

    I spent the whole day today wearing silky stockings under my chef's uniform. It really turned me on working with people while wearing them secretly. I want to sissy up in public now. x   I wore them again today, I would love someone to discover my secret, but I'm also terrified...
    throb42 throb42 41-45, M 5 Responses Apr 21, 2012

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    I know there are far more subs

    than dommes out there, and that puts us subs at a disadvantage. It's so hard to find a strong, intelligent domme that does not have completely unrealistic expectations. So some subs have become "money slaves" to online "dommes" who demand "tribute." To any subs or sissies, I...
    VictoriaFredericks VictoriaFredericks 36-40, M Aug 20

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    Kik Me

    Hi new to this and I dunno if you wanna "chat" wink wink (dom or sub doesnt matter) kik me _whos_in_charge or if you wanna talk and get to know each other thats fine just give me the heads up cause I never go on here
    imyourguy imyourguy 18-21, M Nov 5, 2013

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    Rough Night

    Last night was one of the roughest nights I have ever had. After I had showered and shaved my body I put on a pair of blue panties since I was feeling a little naughty. After the panties were on I decided to go a little farther and I put on a matching bra and some make up. Some...
    Nemo17 Nemo17 18-21, M 4 Responses May 20, 2013

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    yeah i been recently wanting two wear certain

    clothing (crossdressing) and all that since 2 year now only thing is i cant yet i got some girly stuff tho but since i live with my parent they don't know and i don't think i should let them know so i am gona wait till i get my own place
    DarkpawTheSissyFolf DarkpawTheSissyFolf 18-21, M 1 Response Jun 23

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    My Sissy Life

    as a little boy of 7 i would walk to school and home on the way home one day i would pass past the same house and there was a older gentalman there that asked me if i could cut his grass and i agreed well that saturday i went to cut it and it was very hot and he asked me if i...
    lacieann43 lacieann43 41-45, F 3 Responses Mar 16, 2011

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