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I Enjoy Sissy Traing

Personal Stories, Advice, and Support 1,099 People

    Sissy Maid

     A dominant I knew asked me to dress as a maid and serve at a party he was throwing. I was thrilled at the idea of exposing myself as a cross dresser, in a maid uniform that proclaimed my submissive nature, under such controlled conditions. After all I wouldn't be dressed in...
    amandatrane amandatrane
    2 Responses Mar 21, 2012

    Gurls Just Wanna Have Fun

    Imagine! A man that wants to be a maid! I understand you might not find him attractive in some ways but he WANTS to do the dishes! This has got to be a male fantasy women can play into for their own benefit. You buy him a frilly dress with matching bra and panties and he is...
    JustSillyStuff JustSillyStuff
    46-50, T
    4 Responses Sep 11, 2008

    How Many Ways Are There To Train A Sissy?

    How many ways are there to train a sissy? How many Masters and Mistresses are there in the world, but lets look at tools and techniques of deep training and sissy conditioning that will help a sissy fully realize her deeply submissive and erotic nature. 1. Feminization: The use...
    SissyLivia SissyLivia
    36-40, T
    2 Responses Mar 25, 2013

    I agreed to be trained

    as my wife's sissy husband 4 years ago. It was difficult because I wasn't good at any of the house chores, and I would get so excited sexually that I couldn't take it seriously at first. She took it VERY seriously though and was able to help me get past my little sexual...
    herlittlebitch herlittlebitch
    46-50, M
    3 Responses Sep 8, 2014

    Sissy Maid

    love doing housework when dressed up in my satin french maid's uniform.the feel of my shaved legs in stocking walking in a femmie way due to the big butt pug up my sissy ***** and the 5" high heel shoes locked on to my feet.the way the petticoats push out my short dress and...
    mandiejune mandiejune
    51-55, M
    5 Responses Nov 14, 2008

    Top Daddy Looking

    Hi Gurls, I am a Top Daddy looking for a new plaything - if you think you are up to it, let me know and we can discuss. Please check my profile to see who I am and what I am about before contacting me. Adi
    addolan addolan
    36-40, M
    1 Response Apr 10, 2013

    I Have Wanted to Be Trained As a Sissy Since

    i have known that i am a submissive sissy from a young age at 13 i used to steal my aunt's bras and panties and pretend to be tied-up and forced to service the person who kidnapped me and soon after i started i was unable to successfully ********** or climax (even with my first...
    sissykris sissykris
    31-35, M
    1 Response Aug 11, 2009

    Enjoy But Need Help

    Hello there, I do enjoy sisyy training but i need the proper assistance to become the obedient little sissy girl that i want to be. What sort of training should I put myself through? What should I be wearing everyday? Do I need a mistress to train to be the sissy girl I want...
    littlegirlmadison littlegirlmadison
    18-21, M
    Mar 5, 2009

    Taught Like A Dog

    Freshmen yr. of high school my cousin caught me wearing a bra and wearing lingerie under my slothes. My cousin then asked if I would like to be a woman I replied yes since I've always wanted to be a woman. My cousin would always "punish" me whenever I did something unlady like...
    deleted deleted
    1 Response Jan 30, 2011

    My Training

    i haven't been to an official "sissy training' course, seminar, or whatever but i've been living in Female led relationships for years and since discovering i am a sissy girl my Mistress Wife has been training me as an on-going project. i enjoy learning how to be a more...
    sissyslavejamie sissyslavejamie
    51-55, T
    2 Responses Feb 2, 2009

    Found Out Just Lately

    Since an early age I have been dressing in feminine clothing, playing dress up with Mummy's clothing, with her knowledge, then at 7 she started buying me my own. At 12 puberty started setting in and I started my period, once again with her help, at 20 I opted to have implants. I...
    janetkotex janetkotex
    22-25, T
    4 Responses Apr 18, 2011

    My Sissy Husband.

    I make my husband read sissy stories out loud to me while he is naked and watch him get erections when the stories turn to sucking ***** or when getting their sissy hole screwed. I also have him naked when looking at transgender or sissies. It is so amusing to me because he tries...
    confinedhubby confinedhubby
    7 Responses Jan 6, 2013

    My First Experience With A Guy

    I was always very turned on by the whole idea of being submissive and doing what i was told, but never knew why. It took me a long time to really come out and do anything about it. Well finally when i moved out of the house at 19 i got my own place and went craigslist searching...
    mikejones138 mikejones138
    22-25, M
    2 Responses May 30, 2012


    I was in the 1st grade,& it wa 2 week's untill my little Sister's B-Day.I was with a friend at walmart looking for a present for her & we were in the Clothing area,I seen this really cute dress,so I walked over to it& was looking at it when my friend Said"Do u want that dress...
    Crossdresser87 Crossdresser87
    22-25, T
    10 Responses Oct 14, 2010

    Mommy Taught Me

    Being raised by a single mom is nothing unusal but in my case mom was a professional dominatrix.  From the age of 4 my mother began to train me as a submissive male.  I wore girls underwear under my boys clothing while at school.  From birth until age 12 my...
    PantyPrince PantyPrince
    51-55, M
    4 Responses Apr 9, 2010

    Helping Hand

    I just love helping my sissi become the best sissi she can be!!! Being a sissi is not for your average alpha male by no means. I would love to have a sissi 24/7, women just don't know how they would have it made by having a sissi boi around.I absolutely respect and appreciate a...
    sissiluvr sissiluvr
    31-35, F
    4 Responses Aug 27, 2010

    I Loved It

    Once my uncle died (see my experience of first time dressing), my aunt (by marriage) started my sissy feminization training in earnest.  She took me out of public school and told them that I would be home-schooled.  What she didn't tell them that in addition to my...
    SissyGena SissyGena
    31-35, T
    4 Responses Nov 19, 2009

    The Importance Of The Butt Plug

    As I had to explain it to a new potential slave (she started her trial period last week), I thought I might as well share why I think the butt plug should be part of every gurls training.In my book, a gurl should be plugged at all time! (and if you are married, and wifey doesn't...
    addolan addolan
    36-40, M
    4 Responses Dec 29, 2011

    A Day In The Life Of A Sissy Maid

    5.00 Rise, use lavatory, take off pink nylon shortie nightdress, scrub face, hands, bottom and genitals hard with cold water and carbolic soap. Dry with rough towel 5.10 Proceed very quietly down stairs to the kitchen. Iron and quickly get dressed in morning uniform...
    amybrowne amybrowne
    31-35, F
    2 Responses Dec 13, 2009

    My First Lesson In Humility

    As with this adventure, it was a while back....although not exciting I did truly learn a lesson The first few days after my first encounter(posted elsewhere on this site) with Miss M were the longest of my sissy life,it took a day or two for me to fully absorb what had happened...
    cdsusanri cdsusanri
    46-50, T
    3 Responses Nov 16, 2011

    Please Call Me Tinkerbell

    My wonderful, loving, and beautiful wife picked this experience for me to share today. I am her sissy and I love it!  Our love life is perfect because it is her way all the time for her pleasure. I am a submissive, oral, obedient, feminine lick doll sissy and my face...
    deleted deleted
    2 Responses Mar 14, 2010

    A Sissy Training Experience

    I had an experience with a younger woman where I worked I'll call Sue, she was tall, true blond, legs forever.  I don't know why but she got a crush on me, she would have some computer problem and call, I'd go down there, she seldom wore a bra, her nipples stood out, she'd...
    SissyDenise SissyDenise
    56-60, M
    19 Responses Mar 5, 2009

    You Mistress Maid Me Her Gurl

    I have my first bra now, bjut that's a different story. My ex was my mistress and she took ownersjip of my **** and then it was no longer mine - it belonged to her and she would **** me with it and even though is was attached to me she hypnotized me to feel a vagina where she...
    Gendurswitchz Gendurswitchz
    Jan 10, 2009

    Sissy Maid Experience

    I've been receiving sissy training for over half a year and now i love it. I have to meet my mistress on saturdays as i work these days. It's so hard. by day i'm just a normal little guy but by night i'm a sissy. My mistress made me serve a few men as a sissy maid as per my...
    sissyeman sissyeman
    26-30, M
    1 Response Mar 18, 2011

    Home Schooling

    Does Home schooling count
    babybearjean babybearjean
    61-65, M
    1 Response Aug 31, 2009
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