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I Am a Sissy

Personal Stories, Advice, and Support 4,058 People

    .... Schoolgirl Who Likes To Have Her ***** Filled When Dressed. (Updated with new pics of me)

    Currently, my favorite is to get dressed up when my wife is out of the house running errands and I know she will be gone for awhile. I have aquired several very short tartan/plaid schoolgirl skirts from the local thrift store that I can barely get over my hips ($1.00 each from...
    deleted deleted
    18 Responses Dec 8, 2011

    From Lady Lovin Jock To A Sissy **** ****

    Hey there, I now go by the name Kristi! Im 24 years old and up until recently i was a 100%straight jock man that enjoyed the ladies probably more than i should of... Recently while in a horny haze i truly ACCIDENTALLY stumbled onto a video on fem/sissy blackmail of a husband, to...
    AFslut4u AFslut4u
    22-25, T
    4 Responses Jan 20, 2012
    sammi11 sammi11
    41-45, T
    7 Responses Dec 28, 2012

    Caught Lying To My Mistress. (Part One.)

    Enjoying the delights of this scorching heatwave in England last week, I was enticed to tell my gorgeous, understanding Mistress a total lie. She rang me whilst I was at work, stating that she required my services as soon as I had finished, then she would come and pick me up. I...
    chloesiobhan chloesiobhan
    56-60, T
    7 Responses Jul 19, 2013

    I don't think I'm a sissy yet,

    but maybe I'm in danger of entering sissy territory. I have 24 pairs of my own panties. That's not a lot for a man to own, is it? Of course I also own several skirts, some stockings, a corset and at least one garterbellt. I just love the feeling of satin and the way I look in...
    VictoriaFredericks VictoriaFredericks
    41-45, M
    5 Responses Aug 14, 2014

    small pee pee diaper sissy looking

    for humiliation and degradation ASAP please message
    diapeelover23 diapeelover23
    22-25, M
    1 Response Nov 28, 2014

    My Name Is Dana And I Am A Sissygurl

    The four us remained in the kneeling position, too shocked or too afraid to move, for the next hour or so. Rob, or Robin now, kept blaming me for getting them to agree with the kissing scenario. I could not argue that he was wrong. Besides, I was too scared to even think. Larry...
    danagurl danagurl
    26-30, T
    9 Responses Apr 6, 2011

    Conversion To Feminization

    I'm a35 year old separated married man who for many years has been attracted to experiencing sex as a sissy.My wife told me very early in our relationship that she was in no way receptive to being a part of these activities and as a result we went our separate ways.After about...
    Stefffi Stefffi
    36-40, M
    8 Responses Jul 28, 2010

    Loving Being a Sissy Maid

    i worked at fairplay in staten island ny for two years and every tuesday i came to my mistresses house and did all her chores.since she runs a shop for girls like us and she also does makeovers i became one of her maids.i always came to her as a girl and i was able to buy nic...
    phylisanne phylisanne
    70+, F
    5 Responses May 15, 2008

    Sissy , i really don't like

    that term. But i like to wear heels and mini skirts and hose and love long hair. i love to serve others. i played football as a wide receiver for 17 years on a semi pro team. hang around a lot of guys and get lots of hugs from them. they don't know about my dressing.
    slavesindee slavesindee
    56-60, M
    2 Responses Sep 24, 2014

    I like old style little girls clothes with

    puffed sleeves, ruffles, & bows. Love wearing them, looking at pictures of them & seeing others wear them. I see a few I like at their galleries here, but there's gotta be more out there.
    joannebarber joannebarber
    41-45, M
    1 Response Apr 17, 2015

    My Wife Returned

    Two weeks ago, I was sleeping to night, when my ex-wife arrives, wakes me with a slap on the *** and say - I'm back. At the time I froze. And she continued - you liked so much of live like my wife, who continues sleeping in her nightgown. I bet you felt my absence. Then now I'm...
    deleted deleted
    8 Responses Oct 28, 2012

    diaper sissy with small pee pee looking

    for degradation and humiliation in my messages ASAP. Please message as soon as possible.
    diapeelover23 diapeelover23
    22-25, M
    Oct 22, 2014

    The Sentence. (Part Four.

    ) On returning with my Mistress, she informed me that so far all I have done is pay the emotional fine, now I must carry out my sentence. She further explained that she will instruction me on what I must do once we arrive at her place. The rest of the conversation was...
    chloesiobhan chloesiobhan
    56-60, T
    6 Responses Mar 9, 2014
    Sissybitch21 Sissybitch21
    Sep 27, 2014
    mliza301 mliza301
    26-30, T
    3 Responses Apr 18, 2015

    i have found a chastity master ep im

    so excited hes going to put me in a pretty pink chastity device lol i cant wait to finally be the sissy slave i always wanted to be ill keep everyone posted lol text me if you want some pics and videos lol
    Samantha779 Samantha779
    26-30, M
    3 Responses Dec 31, 2014

    I'm a sissy I love dressing up in women's

    clothing and under wear love to have someone I could share this with and have some fun with them
    deleted deleted
    2 Responses Aug 1, 2015

    If you want stable and usable sissy forum I

    recommend to use
    fpzshka fpzshka
    22-25, T
    Apr 7, 2016

    I am a depraved diaper sissy,

    anything goes with me. There are no limits, I am looking for somebody to message with and humiliate me. Pls send me messages
    diapeelover23 diapeelover23
    22-25, M
    1 Response Oct 13, 2014

    Mistress reminds me each

    and every day that this is what i was always meant to be, that my only purpose in life is to serve Her, to work to please Her and to do everything She demands of me without questions. In order to pay for my own clothing, accessories and toiletries, i have to work, and it is the...
    SissySonja SissySonja
    46-50, T
    2 Responses Sep 26, 2014

    The special part of feeling sissy

    for me, is having a very small ...... for me I've really embraced this wonderful feeling, it gets emotions going knowing that real men are very special.
    deleted deleted
    Mar 18, 2016

    I love to talk about

    and look at girly clothes, be great to be able to go shopping with someone but is there anyone here who would like to chat about clothing and girly stuff?
    cdjanine cdjanine
    8 Responses Jul 21, 2014

    I'm a Sissy ~ Luckily

    My story … well … as my name suggest, I’m a sissy. I’m not complaining … just the opposite … it’s like a stroke of luck. I love it. Life would be so dull and boring if I weren’t. I’m really happy to be so special and...
    CherrySissy CherrySissy
    46-50, T
    21 Responses Aug 15, 2008

    I'm looking for guys in my area to play with.

    I'm in Georgia south of Atlanta.
    sexyalyssagurl sexyalyssagurl
    41-45, T
    Feb 26, 2016

    That's pretty much it.

    I've been curious about crossdressing and feminization for as long as I can remember, but I've always supressed and denied it. I've told myself a thousand ways why it's wrong for a male to dress in Women's clothing, but after 21 long years, I'm finally giving in and accepting...
    SissyslaveVanessa SissyslaveVanessa
    22-25, M
    7 Responses Aug 12, 2014

    I love to wear big pink gowns

    and just loose all my masculinity
    diapergearsolid diapergearsolid
    26-30, T
    2 Responses Dec 11, 2014

    More to follow!

    A while ago I had a girlfriend. We met through a friend. She knew I was interested in guys but didn't mind, actually - she told me that she loved gay boys, and loved making them have sex with each other. She told me that she was going to make me much, much more gay that what I am...
    girlydimpale girlydimpale
    18-21, M
    7 Responses Sep 2, 2012

    diaper sissy looking

    for a daddy. please message!
    diapeelover23 diapeelover23
    22-25, M
    1 Response Mar 10, 2016

    When My Wife Found Out That I Was A Sissy

    So about 3 yrs ago my girlfriend at the time was a work so I thought. Well she left for work. So I figured I would dress up and do some house work. Well as the time went by I was danceing singing like a sissy. When she walk in the door. The look on her face surpirsed that I was...
    Sissyjim3 Sissyjim3
    31-35, M
    2 Responses Aug 21, 2012

    Yes I am! I love pleasing men

    and dressing like a girl. Panties (which I wear exclusively) stockings lingerie bras dresses heels lipstick the works. If only I could find a man that needs a sissy to take care of his sexual needs. I will be there to do just that whenever he wants. If he needs some head all he...
    SissySubAlyssa SissySubAlyssa
    36-40, T
    Mar 20, 2016

    Getting smaller - I've noticed that

    since relations with my wife (continued below)
    Bellringer2c Bellringer2c
    56-60, T
    3 Responses Sep 28, 2014

    My Wife's Sissy

    Having been through two other failed marriages because of my feminine ways I choose to tell my future wife about who I was. Fortunately for me she has a "thing" for my soft feminine side and we have escalated from there. We buy ALL my clothes together and I have become quite good...
    marysgirl marysgirl
    61-65, T
    5 Responses Sep 7, 2011

    Visit To The Bath House

    Many years ago I read on a local gay newspaper, about a sauna for this community. Meaning the gay community. After giving it plenty of thought I finally built up the courage one Saturday to go and try out this place. I found the place easily and after driving around the block a...
    Sissydoll56 Sissydoll56
    61-65, M
    15 Responses Mar 15, 2012

    I'm a 71 year old crossdresser

    and I have strong feminine feelings and urges all of the time. To satisfy those urges, I need to wear a bra, panties and occasionally have a need to dress fully en femme. In addition to my being a crossdresser, though, I also am a sissy because I love to serve and to satisfy...
    DonnaSue10 DonnaSue10
    66-70, M
    4 Responses Sep 25, 2014

    A Couple Used Me

    I once answered an ad to play with a couple. I was a cross-dresser and so was the husband. It turned out that the wanted to just use me. yes the husband did cross-dress and his wife was cuckolding him with her boss which he husband enjoyed. The husband had a 9" thick tool I can...
    glorialamuse glorialamuse
    9 Responses Jan 23, 2011

    Mistress Guided My First *********** Experience

    This is my true tale of the first time I was 'encouraged' to suck a real man... I had seen a few pro dommes in person by the time I was in my late 30's. Also chatted with some phone dommes occationally. Well, I had been chatting with this phone domme for a few months. She...
    tvshannon tvshannon
    51-55, T
    23 Responses Jun 1, 2012

    Sissy Sex At The Drive In.

    I remember when I was a teenager many years ago we used to go to the drive-in theatre almost every weekend during the summer. It was the best thing to do if you didn´t have a party to crash or money to spend at clubs. It was also the best place to have sex if you couldn´t...
    Sissydoll56 Sissydoll56
    61-65, M
    20 Responses May 22, 2012

    I never thought of being a sissy.

    While in college, it was obvious that I was not to dominate any of the men, but rather was there to make sure they were very satisfied. The guys told other guys I was available, and easy. I always was the female in the sack.
    donn2 donn2
    61-65, M
    3 Responses Aug 11, 2014
    sammi11 sammi11
    41-45, T
    11 Responses Mar 29, 2013

    Went outside dressed in a very short baby doll

    to put the garbage in the can. when I tried to come back in the house, my cat got out! I tried to catch him, but my call to Mistress about the cat, made her turn the outside light on to see better! Well, there I was, outside in a really short nighty, trying to catch our cat...
    michelle4446 michelle4446
    51-55, T
    5 Responses Sep 10, 2014

    I am a sissy and I embrace by ability to

    please men like a sissy should.
    chrissyk48 chrissyk48
    46-50, M
    3 Responses Mar 19, 2016

    Sissy is derived from sister it is a pejorative

    term for a boy or man who violates or does not meet the traditional male gender role. Generally, sissy implies a lack of courage and stoicism, which are thought important to the male role. A man might also be considered a sissy for being interested in traditionally feminine...
    CdKimmi CdKimmi
    66-70, M
    3 Responses Sep 12, 2014

    I am a sissy because i like to wear womens

    clothes and act girly, i also like to have sex with men but i also like women too, so i guess i'm bisexual, when i have sex wih a guy, i have to be dressed up appropriately, normally in a sexy nghtie or some hot lingerie
    NicolaCD NicolaCD
    51-55, M
    4 Responses May 9, 2015

    I must be a sissy I love to dress in women's

    under wear and clothing and tuch my self all over and enjoy every second of it I inmagen it is someone else tuching me it make me so hornny and wet just thinking about it
    janetjan janetjan
    51-55, T
    Nov 3, 2015

    Hello,my name is jacob

    but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this. i am now seeking help from someone who lives near me. i live in Virginia and am looking for some one I can meet, i love EP...
    zoey764 zoey764
    18-21, T
    1 Response Jul 23, 2014

    My First Day At School

    (continued) After a sleepless night of being worried about how the school would take me in, it was time to get up and ready for school. My step-mom had woken up early and picked out an outfit for my first day of class as Layla. I was hoping that this morning it would've all been...
    Sexxxiinfem Sexxxiinfem
    22-25, M
    3 Responses Jul 7, 2013

    Being the Real Me

    I finally decided to quit fighting & allow my feminine side to come out to the world.  The "she" part of me was dominant & I was tired of living the macho charade  which brought little else but frustration & disappointment. I wanted to be ME, the...
    dvdfg9 dvdfg9
    41-45, T
    17 Responses Mar 1, 2008
    22-25, F
    2 Responses Sep 4, 2014

    I love wearing panties

    and sexy lingerie. I love wearing stocking and slutty heels. I love painting my toes it makes me feel so feminine. I want to dress up and be a mans play toy. being with a straight married man is a big fantasy of mine ive done it once lol. It was amazing. I want to give a man a...
    deleted deleted
    7 Responses Mar 13, 2014

    My First Time.

    My first time? Well, I can't remember the moment precisely for it happened a very long time ago. As a young boy I was apparently straight. I'd had a crush or two on girls although I was extremely shy to do anything about it. I'd ********** to fantasies with girls or movie stars...
    Sissydoll56 Sissydoll56
    61-65, M
    25 Responses Mar 10, 2012

    Why bother denying it anymore?

    I am an utter girly girl and one of my absolute favorite things is being with other girly girls or being subservient to one. It's part of who I am, there's no need to compartmentalize it anymore. What does it accomplish? Nothing. Do I blame or hold it against others that do? No...
    ViewtifulMe ViewtifulMe
    26-30, T
    4 Responses Jan 5, 2015

    I Guess Its Official.

    Last night my wife called our dog a pansy, and joking i said don't talk about me like that. Her reply was "if i was going to call you anything it would be a sissy".  and now a little more of an update yesterday afternoon i ordered my first wig, so i can be a little more passable...
    AmberRosecd AmberRosecd
    36-40, T
    10 Responses Apr 17, 2013
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