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I Am a Sissy Boy

Personal Stories, Advice, and Support 2,535 People

    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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    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 5 Responses Oct 24, 2012

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    15yo Sissy, Looking To Chat With Older Cute Dudes

    title says it all, so how about it? ;)
    sissyboy56 sissyboy56 22-25, M 3 Responses May 29, 2013

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    Sarah was made into Her Sissy **** Slave

    It was Saturday morning and I decided to get my laundry done before going out for lunch. I took my stuff down stairs to the basement laundry room, loaded a washer and started the cycle. I was about to go back up to my place and wait for my things when I noticed a basket of...
    SarahCD707 SarahCD707 51-55, M 5 Responses Aug 19, 2012

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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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    hmmmm if wearing girly clothes

    and wanting to please men makes you a sissy then I guess I'm not a sissy boy. I pretty much only fantasize about wearing girly clothes and pleasing men. I am pretty sure that I will never really become a sissy boy in real life but on EP I can be whoever I want to be
    deleted deleted 26-30 1 Response May 18, 2015

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    Other names that I own

    and am very proud of are fairy, swish, poof, cummie buns, prissy boi, sissy queer, princess pink *****, limp wristed prissy boi, femme boi, flaming homo and many more. If you are one be delighted and when someone recognizes you as a swishy sissy fairy and calls you any of these...
    deleted deleted 26-30 4 Responses Aug 18, 2015

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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 2 Responses Jun 23, 2014

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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 4 Responses Feb 27, 2014

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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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    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 1 Response Aug 21, 2012

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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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    Humiliation

    The first time I realize i was a sissy was when i was 16 and went to the hospital, they had me pull down my pants to do something to my penis and i just love all the office girls giggling in the backround at my small little penis while walking back and forth with their high heels...
    girlydimpale girlydimpale 18-21, M 4 Responses Aug 5, 2012

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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 28 Responses Nov 13, 2011

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    So, I'm currently aged 18,

    and I'm just starting to become a sissy. I have dressed up in my sisters clothes a couple of times, when the house is empty. Recently, I found something in my parent's room that astounded me: a vibrator wand. When I had the house to myself, I dressed up in a school uniform: Mary...
    deleted deleted 26-30 3 Responses May 4, 2015

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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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    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 11 Responses Jul 23, 2009

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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 7 Responses Mar 28, 2012

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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 20 Responses Jan 10, 2011

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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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    Sissy Training Candidate

    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!
    tgirl60 tgirl60 26-30, M 6 Responses Oct 19, 2012

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    Nothing on but on white stocking

    and one black stocking...anybody wanna play...luv to show some girls of ANY age
    deleted deleted 26-30 1 Response Jul 7, 2015

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

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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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    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 22-25, M Nov 5, 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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    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 24 Responses Apr 3, 2011

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    locked125 locked125 26-30, M 1 Response Dec 31, 2015

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    I Shaved My Legs

    for the first time, and i must say i love how smooth they are ^_^! didnt shave my arms tho, couldnt get away with it. next step: dress, wig, and makeup. im gonna be so pritty
    yoursissyboy yoursissyboy 22-25, T 2 Responses Jun 17, 2013

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    I love the thought of being a sissy.

    I'm 17 and all my life I've had the thought that I was gay or bi, but I was always terrified of what others would think. At the beginning of the year I came out to everyone as being bi, and after experimenting I've found that I love anal. I play with myself everyday in the...
    Cumdumpster22 Cumdumpster22 51-55 2 Responses Jul 18, 2015

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    Swing both ways...luv to dig in

    or get dug into...message me; ) any age or gender
    deleted deleted 26-30 Jul 20, 2015

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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 22-25, M 1 Response Apr 16, 2013

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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 2 Responses Oct 6, 2014

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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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    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 22-25, M 1 Response Nov 23, 2013

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    Dreamer99099 Dreamer99099 31-35, M 1 Response Jan 24

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    i love being a crossdresser enjoying th elace

    and the sexy lingerie! ahh talk to me coz im a lonely girl and im on this good site too you should give it a go :) /www.cottaging.co.uk/ find me beardyxdresser xx
    MsRay MsRay 18-21 1 Response Oct 8, 2014

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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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    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 2 Responses Apr 17, 2013

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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 3 Responses Oct 27, 2013

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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 3 Responses Oct 29, 2011

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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, 2014

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    Hey :)

    Someone talk to meeeeeee!xx xoxo
    Sissygurlxx Sissygurlxx 18-21 6 Responses Oct 19, 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 5 Responses Aug 18, 2012

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