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I Am a Sissy Boy

Personal Stories, Advice, and Support 2,441 People

    Swing both ways...luv to dig in

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

    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

    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

    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

    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

    I Am A Budding **** Sucker

    Miss Zanmi has told me to write about my **** sucking desires she knows that deep down I am a *********** ****** even though I have never acted on these desires and maybe never will. No one knows about these desires accept Miss Zanmi. So as I sit here in my black stockings...
    seanmcaa seanmcaa
    26-30, M
    5 Responses Jan 20, 2013

    My First Real Fun With Somebody

    We had a neighbour friend George who was in his 60's and for some reason as a very young teen I was attracted to him. With my curly hair, very slight frame and being short I was quite femme and very tactile and would always play around jumping on laps etc., I hated going into...
    legsylynne66 legsylynne66
    46-50, T
    16 Responses Nov 29, 2010

    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
    1 Response Jun 17, 2013

    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

    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

    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

    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

    Hey :)

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

    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
    2 Responses May 21, 2012

    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

    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

    Hey guys, New to this.

    Im a 28 year old sissy from Canada. My name is Jessica Lynn. I've recently just discovered this side of myself and love it. Anyone want to help me out with questions can you message me or lead me in the right direction :P
    JessicaLynn6969 JessicaLynn6969
    26-30, T
    1 Response Feb 28

    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
    22-25, T
    1 Response May 8, 2013
    locked125 locked125
    26-30, M
    1 Response Dec 31, 2015

    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
    22-25, M
    Nov 5, 2013

    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

    It took me a long time to realize

    that I am a sissy but I accept it. I love to dress up sexy like a girl and please men. Whether I am on my knees or bent over with my panties around my ankles taking in my bottom. I am always looking for a man to please. If any guys are looking for a sissy or if any other sissies...
    SissySubAlyssa SissySubAlyssa
    36-40, T
    Mar 21

    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

    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

    Unexpected Visitor

    I was relaxing at home wearing only Baby blue panties and Bra, black fishnet stockings and suspender when a heard a knock on my Ranch slider door. I, without thinking, turned around to see a woman of around 30 years old standing there smiling. It was too late to try and hide or...
    Fondleme Fondleme
    61-65, M
    3 Responses Feb 21, 2013

    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

    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
    Dreamer99099 Dreamer99099
    36-40, M
    1 Response Jan 24

    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
    9 Responses Dec 9, 2012

    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

    Anyone out there willing to make me their own

    little sissy slave? Message me...
    LJTE LJTE
    26-30, M
    Feb 7

    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

    "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, 2014

    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

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

    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
    18 Responses Jan 10, 2011

    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

    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
    Sep 26, 2013

    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
    3 Responses Oct 24, 2012

    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

    This Site Is Awesome

    http://www.dolldivine.com/
    Aeslyn Aeslyn
    36-40, T
    May 19, 2013

    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

    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

    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

    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
    27 Responses Nov 13, 2011

    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

    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
    3 Responses Aug 18, 2015

    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
    10 Responses Jan 28, 2013

    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

    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

    my mother was a single parent

    and had to work so she had a friend with a daughter my age that would babysit. her daughter and i would play with dolls and have tea parties.i used to pee my pants on purpose so she would give me a pair of her daughters panties to wear . i think she knew i did it on purpose...
    rhondacdma69 rhondacdma69
    61-65, T
    Mar 16

    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

    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

    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
    5 Responses Oct 19, 2012

    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

    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

    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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