Post
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Am a Sissy Boy

Personal Stories, Advice, and Support 2,293 People

    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...
    BillieWill4U BillieWill4U 18-21, M 5 Responses Oct 29, 2011

    Your Response

    Cancel
    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...
    smiteenyb smiteenyb 56-60, M 3 Responses May 21, 2012

    Your Response

    Cancel
    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...
    deleted deleted 26-30 2 Responses Aug 22, 2010

    Your Response

    Cancel
    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...
    joann4urplsur joann4urplsur 56-60, T 2 Responses Apr 2, 2013

    Your Response

    Cancel
    Forgive Me. - I have to admit it, I've been off this site for about a month. I don't know, it might have been job stress,moodiness or voodoo. Anyway,when I got home tonight I knew...
    Lilly292 Lilly292 41-45 Mar 18, 2013

    Your Response

    Cancel
    Listen Carefully... -
    sammi11 sammi11 41-45, T 6 Responses Dec 19, 2012

    Your Response

    Cancel
    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...
    artycampbell artycampbell 51-55, M 11 Responses Dec 9, 2012

    Your Response

    Cancel
    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...
    jenncd41 jenncd41 41-45, M 1 Response Oct 3, 2013

    Your Response

    Cancel
    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...
    vanit vanit 26-30, F 9 Responses Jan 28, 2013

    Your Response

    Cancel
    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...
    throb42 throb42 41-45, M 10 Responses Mar 28, 2012

    Your Response

    Cancel
    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...
    pinkbabysnowboi pinkbabysnowboi 18-21 21 Responses Jan 10, 2011

    Your Response

    Cancel
    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...
    Simkalr Simkalr 22-25, T 2 Responses Jan 12, 2013

    Your Response

    Cancel
    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...
    jesslovecock jesslovecock 18-21, T 1 Response May 8, 2013

    Your Response

    Cancel
    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...
    Ebonysissy Ebonysissy 51-55, F 1 Response Apr 3, 2013

    Your Response

    Cancel
    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...
    imyourguy imyourguy 18-21, M Nov 5, 2013

    Your Response

    Cancel
    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...
    karenjensencd karenjensencd 41-45, T 3 Responses Oct 27, 2013

    Your Response

    Cancel
    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...
    rogume01 rogume01 46-50 3 Responses Jul 18, 2013

    Your Response

    Cancel
    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...
    SarahCD707 SarahCD707 51-55, M 2 Responses Aug 21, 2012

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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...
    louise37 louise37 36-40 28 Responses Nov 13, 2011

    Your Response

    Cancel
    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...
    girlydimpale girlydimpale 18-21, M 4 Responses Aug 5, 2012

    Your Response

    Cancel
    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...
    jackson38 jackson38 70+, M Apr 9, 2013

    Your Response

    Cancel
    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...
    SarahCD707 SarahCD707 51-55, M Aug 16, 2012

    Your Response

    Cancel
    "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...
    kent1973 kent1973 56-60, M Mar 11

    Your Response

    Cancel
    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...
    danseuretoile danseuretoile 31-35, M 4 Responses Oct 24, 2012

    Your Response

    Cancel
    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...
    lapsode lapsode 22-25, M 2 Responses Apr 10, 2013

    Your Response

    Cancel
    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...
    samantha222 samantha222 31-35 13 Responses Nov 17, 2011

    Your Response

    Cancel
    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...
    lazyzach2010 lazyzach2010 22-25, M 1 Response Apr 17, 2013

    Your Response

    Cancel
    This Site Is Awesome - http://www.dolldivine.com/
    AnonymityDarkstone AnonymityDarkstone 31-35, T May 19, 2013

    Your Response

    Cancel
    Bisexual Master - Hi there you sissys boys I am a Dom and a man but on occasion I find myself wanting to own a little sissy boy of my own and to train him along side a female slave...
    Kinkyalex Kinkyalex 22-25, M 3 Responses Mar 25, 2013

    Your Response

    Cancel
    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...
    emilies emilies 36-40 20 Responses Apr 3, 2011

    Your Response

    Cancel
    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...
    danseuretoile danseuretoile 31-35, M 6 Responses Aug 18, 2012

    Your Response

    Cancel
    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...
    Vicky333 Vicky333 41-45, M 10 Responses Jul 23, 2009

    Your Response

    Cancel
    I Want To Be Sissy Boy Frind For Girle - i will do any thing u want
    truesissyman truesissyman 26-30, M 1 Response Mar 13, 2013

    Your Response

    Cancel
    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...
    overthekneeplease overthekneeplease 41-45 6 Responses Jun 15, 2009

    Your Response

    Cancel
    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...
    SarahCD707 SarahCD707 51-55, M 7 Responses Aug 19, 2012

    Your Response

    Cancel
    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...
    JesseWenchester JesseWenchester 22-25 3 Responses Apr 8, 2011

    Your Response

    Cancel
    my sister dress me like her baby sister with a yellow dress and red nail polish
    jskem jskem 61-65, T 3 Responses Feb 27

    Your Response

    Cancel
    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...
    Mikereedhd Mikereedhd 18-21, M 1 Response Apr 16, 2013

    Your Response

    Cancel
    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...
    mrmike554 mrmike554 18-21, M 1 Response Sep 26, 2013

    Your Response

    Cancel
    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...
    legsylynne66 legsylynne66 46-50, T 18 Responses Nov 29, 2010

    Your Response

    Cancel
    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...
    HayleySissy HayleySissy 22-25 Mar 20, 2013

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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...
    throb42 throb42 41-45, M 5 Responses Apr 21, 2012

    Your Response

    Cancel
    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...
    SarahCD707 SarahCD707 51-55, M 2 Responses Aug 15, 2012

    Your Response

    Cancel
    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...
    imyourguy imyourguy 18-21, M Nov 5, 2013

    Your Response

    Cancel
    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...
    yoursissyboy yoursissyboy 22-25, T Jun 14, 2013

    Your Response

    Cancel
    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...
    cameltoepanties cameltoepanties 36-40, M 10 Responses May 26, 2012

    Your Response

    Cancel
    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...
    lacieann43 lacieann43 41-45, F 3 Responses Mar 16, 2011

    Your Response

    Cancel
    My New Sissy Friend Paula - I met teh most wonderful sissy friend here on EP about 3 weeks ago. Her EP id is feeknoxgirlpaula. She is so greatful to have me in her life. I am...
    andreaneejustinfield andreaneejustinfield 41-45, T 7 Responses Jul 12, 2012

    Your Response

    Cancel
    Pantie Boy - I love wearing panties. I am absolutely dying to be treated like a dirty little girl by an older man. It has been knawing at me for a long time and I am ready to...
    SissyCurious39 SissyCurious39 36-40, M 3 Responses Mar 6, 2013