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I Love Being A Gay Sissy

Personal Stories, Advice, and Support 504 People

    Finding My Gay Sissy Self

    Only recently I have finally found my calling: a sissy femme guy that craves ****. I have had a long evolution from regular girls with vanilla sex to a top for femmine tgirls to versatile with tgirls to fem boys to becoming a sissy for men. The biggest catalyst was meeting on...
    xcheeta xcheeta 46-50, M 3 Responses Feb 17, 2012

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    How I Became A Sissy

    It started over Craigslist. I've never had much luck finding guys, so I decided to give the interwebs a try. I replied to a few posts, but I had no luck. I could hold an email conversation for a while, but as soon as I sent my picture, guys would just ignore me. the thing is, I...
    SandyAego SandyAego 22-25, T 2 Responses Mar 4, 2013

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    Gay Sissy Housewife In Lingerie

    I'd love to keep house for a cute boyfriend. I'd have to wear a dress or skirt when I go out, but at home I'd only wear pretty lingerie. I'd keep the house clean and the meals cooked wearing only panties, a bra, stockings, garter belt and heels. For formal occasions, I'd add a...
    NathanielPantied NathanielPantied 46-50, M 7 Responses Oct 17, 2011

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    It'S Taken Years

    I started out like most men, in a certain role, being with women. As I got out on my own I had started to experience different things with men. At first I thought I should take the role as a top but started to really know that wasnt me. While I was stationed at Ft Bragg, a very...
    toromova toromova 36-40 1 Response Mar 1, 2013

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    Playing With Another Sissy And Being Watched

    I just love being with another sissy, dressed in our lingerie, and rubbing our pantied crotches together. Feeling our ***** get hard as we rub each other through the soft fabric of our panties makes me feel so decadent. It's so hot when we are both wearing pantyhose too, and...
    sissynikkicd sissynikkicd 41-45, M 4 Responses Oct 20, 2013

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    My Boyfriend Takes Me For A Possible Life Changing Appointment

    For what seems like a long time Randy and I have been living quite happily together. He is an incredible man, he works hard and takes good care of me. In turn I work to be a good lady (how he addresses me) for him. He makes a strong salary, and I have been able to cut back on...
    mechanicman mechanicman 36-40, M 1 Response Oct 28, 2012

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    What Gender Is Your Brain?

    i took the "What Gender is your brain?" Testhttp://www.blogthings.com/whatgenderisyourbrainquiz/My brain is "87% Female and 13% Male"You have the brain of a girly girlWhich isn't a bad thing at allYou're empathetic, caring, and in tune with emotions.You're a good friend and give...
    spjennifer spjennifer 46-50 2 Responses Feb 6, 2013

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    Three is a crowd ~ my second experience with

    another guy came a few months after the first. I had several failed attempts at meeting other guys who misled me about what they wanted... And had just about given up on the thought of ever trying the s*x thing again, when I got an email late one Saturday night on my online...
    WillingStudent WillingStudent 36-40, M May 2

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    I Love This Group's Avatar ...

    ... but would really like to find a much larger version of that picture.I've tried enlarging it with various editors, but that only ruins it due to lack of resolution. There's probably a larger original somewhere, but I've had no luck in finding it.Can anyone here help?Thanks.
    TiedUpSissy69 TiedUpSissy69 66-70, M 1 Response Nov 23, 2012

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    Finding My Way As A Gay Sissy

    I'm addicted to being passive and feminine. I feel so complete and know my place when a strong man takes me and makes me his. I have never known what it's like to be the alpha male that all women and sissies want. All my relationships failed because I simply am not an alpha...
    sissynikkicd sissynikkicd 41-45, M 2 Responses Sep 18, 2013

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    Another Encounter With My Lit Professor

    So like I said on my last post, my lit professor (for the sake of not using real names, I'll call him Mr. Jones here) discovered my secret that I am a closet sissy. After that humiliating experience in his office, things have been pretty calm, although I've seen him glancing over...
    SandyAego SandyAego 22-25, T 6 Responses Apr 3, 2013

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    Bi Sissy

    i love being sissy i only wish i had a sissy friend to be sissy with i put up the logo hope you like wish i had a sissy Friend like them steph
    deleted deleted 26-30 10 Responses Apr 22, 2011

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    Picture Says It All

    Just luv the avatar for this group. It speaks volumes to us sissy fagg0ts. I, too, like to dress up in feminine finery and strut my stuff...makes me feel so queer.
    janusatv janusatv 61-65, T 1 Response Sep 15, 2013

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    Let Yourself Become A ****** Fucktoy

    Go on craigslist and find a man that needs to be sucked. Meet him in a park or public bathroom. Dont say a word to him just get on your knees unzip his pants and suck the *** out of his hot ****. Swallow his load lick his **** till its clean then thank him and go home so you can...
    iwantitbad2322 iwantitbad2322 22-25, M 12 Responses Aug 19, 2013

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    *** **** sissy:)

    It's true. I now know my place in life. It's too bee on my needs sucking **** like a good sissy slutty boy. I enjoy having **** up my *** and in my mouth. My **** is soo little an that is what makes me the slutty ***** I am today. In slim very cute and would make a great **** toy...
    girlydimpale girlydimpale 18-21, M Oct 23, 2012

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    Sissy Confidence

    To really be a sissy seen by others, you really, well, have to have guts. Self-assurance. Sounds funny, doesn't it? But think about it. To prance around in panties and lingerie, to go out with some others in girly colors and with some panty lace showing, takes guts. The women...
    NathanielPantied NathanielPantied 46-50, M 5 Responses Nov 7, 2011

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    Knowing My Place

    My place as a gay sissy is on my knees, ready to suck or be ****** by any **** that needs a release. I love it when a real man can see me in my lingerie, so he'll know I'm not a real man. I love to fill my mouth with his **** while I get hard in my panties, so he'll know how...
    sissynikkicd sissynikkicd 41-45, M 1 Response Sep 17, 2013

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    Transvestite Date

    I'm sort of in the afterglow of some sissy sex I had yesterday. I actually got so worked up reading posts here I just had to do something about it. I perused the classifieds of a local adult publication seeking a transvestite. I have been with numerous MtF transsexuals. However I...
    sissykristin sissykristin 56-60, M 53 Responses Dec 30, 2012

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    An All Female Wardrobe And A Mouthful Every Morning

    A quick post to update some happens in my life and relationship with Randy. Since my last post I have gotten rid of all my male clothing. I know work from home and from morning to evening I dress like a woman. I have been working hard on my figure, and from my diet, exercise...
    mechanicman mechanicman 36-40, M 1 Response Dec 12, 2012

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    My Life Is A Sham!

    I'm 50 years old and a totally gay, ****-loving, submissive, pink sissy pantyboy in private. I work for a military contractor and am surrounded by military or ex-military men. I can't "come out" at work as I'd more than likely lose a 6 figure job that I love doing as none of the...
    spjennifer spjennifer 46-50 12 Responses Jul 9, 2012

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    The Plain Truth For Gay Sissies

    Here's an anonymous post I read on another site but it is so true for most of us gay sissies, read it and understand what you truly are, i know i found revelation in it. There is truth here for some of us. Thanks to anonymous! Good ‘sheboiz’ shouldn’t be allowed to...
    spjennifer spjennifer 46-50 10 Responses Jun 9, 2013

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    I Love Being A Sissy

    Who likes nothing better than being dressed up for a night out. You know what I mean. You spend the day pampering, making sure every where is waxed to perfection. Then preparation getting hair dried, nails polished hands and feet). Then make up. got to be right. The right...
    ris9358 ris9358 51-55, M 6 Responses Mar 19, 2013

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    Am I Really A Sissy Or Just A Flaming ******?

    I put on my first pair of panties (Mom's) when i was 8 years old and fell in love with lingerie right then and there. I was raised by a single Mom and was i guess what we'd now call a "latchkey kid" so i had a lot of time to play in Mom's lingerie and she had quite a bit of it...
    spjennifer spjennifer 46-50 16 Responses Mar 25, 2012

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    No Inhibitions

    I went through a period in my early 20's when I was able to experience and fulfill my fondest fantasies. I began wearing women's clothing in places other than my apartment and began meeting other guys interested in male-male sex. In no time at all, I realized the combination was...
    janusatv janusatv 61-65, T 6 Responses Sep 28, 2011

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    Going To The Cleaners

    One night I got all dressed quite slutty and went to our special park and got on the stroll. I had not gotten very far before I was taken behind some bushes for the start of a very busy night. When I got home I found I not only had grass stains on my knees but all over my mini...
    csgwen csgwen 41-45, T 11 Responses Aug 9, 2013

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    I Need A Boyfriend!

    Ever since I moved away for college, I have been abstinent. I left my boyfriend back home because I didn't want him to feel like I didn't want him to have sex anymore. The worst part is that I have a roommate so now i have to keep my sissy life on the DL (ugh!) and pretend to be...
    SandyAego SandyAego 22-25, T 1 Response Mar 18, 2013

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    Kissing The Football Teams Jocks

    Back in high school, my mom always bought me the tightest little briefs. And even worse, they were all in pastel colors! All the guys in the locker room called them my 'spankin shorts'. One day, a guy on the football team made me kiss his jock for good luck, in front of everyone...
    tinydickpantyboy tinydickpantyboy 26-30 3 Responses Sep 24, 2011

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    Gay Sissy

    It is so nice being a gay sissy. I get to be the feminine one in the relationship. being the receiver and the submissive one wearing pretty panties, nighty's and such. being the girly role and I just love having my bf take care of me physically and emotionaly. playing the...
    sissiegirl sissiegirl 51-55, T 17 Responses Mar 16, 2011

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    Toilet-time For Sissy!

    This is only a sick and twisted fantasy.This contains a spanking and ****/watersports fetish.You have been warned.Have Fun.I knelt before Daddy in just my pink panties, my whipping with my own belt finally over. Now it was time to thank my Daddy for my 'correction.' Daddy was...
    tinydickpantyboy tinydickpantyboy 26-30 Apr 6, 2013

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    My Boyfriend (finally) Takes Me In Front Of Someone

    If you have read some of my previous stories, you know that I started my recent life changes as a cuckholded husband. I watched my wife get taken by her masculine boyfriend multiple times, and it was incredible. With her help and with a lot of love from the total love of my...
    mechanicman mechanicman 36-40, M Nov 12, 2012

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    Cumslut

    just love being a sissy cumslut and love having my holes filled by hard ****!often look at guys thinking about undoing their pants and leeting their **** free so i can suck it and swallow the ***!often go out dressed as a sissyslut to attract a gay guy to **** me!!still remember...
    mandiejune mandiejune 51-55, M 6 Responses Jul 8, 2011

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    A Filthy ****

    Simon is a perfect ***** ever his with me for a month now the perfect sissy you could find I’m proud of my creation a cute French ***** it's weird when you see him a tall muscled hunk with an incredible six pack you will never know his filthy secret any way I invited 12 guys to...
    sarabx sarabx 26-30, F 3 Responses Sep 14, 2013

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    I Was Asked Do You Want To Blow Me.

    I was on Silverdaddies site and a guy asked me if I wamted to blow him.I said yes and went to his house and sucked him off. A nice thick 6 1/2' cut **** . MMMMMMMMMMMMMMMMMMMm it was so good.He just laid there and I put my mouth to work.He was in heaven as he moaned . i sucked...
    specialgurl specialgurl 61-65, M 6 Responses Aug 29, 2011

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    Sissies Are Toys For Real Men

    I'm addicted to giving up my body to any real man who wants to use it and remind me that I'm not a real man. Never was, never will be. I love being a girly submissive little *** who is helpless when a guy wants to take me. I'm the one who daydreams about lingerie and being...
    sissynikkicd sissynikkicd 41-45, M 1 Response Sep 18, 2013

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    Having A Beautiful Loving Relationship With Daddy'S ***

    This is only a fantasy.It's about *******.You have been warned.Have fun.When I arrived at His house, I was to ***** down to just my pink panties, ring the doorbell, and then kneel down, nose to floor and wait for Daddy to come get me.He opened the door but I was to remain with my...
    tinydickpantyboy tinydickpantyboy 26-30 Apr 6, 2013

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    My Professor Had A Surprise For Me.

    So it's been a while since my second encounter with my Lit Professor, Mr. Jones. ever since then, I have been wearing lacy panties and push up bras on a daily basis, and also a heavy sweater to hide my femininity even though we are currently having some incredibly hot weather in...
    SandyAego SandyAego 22-25, T 1 Response Apr 24, 2013

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    Sissy ****?

    Last weekend i went to meet up with a Man I met online, the evening progressed as expected and we ended up in His bed together, He was very well hung at 9.5" and almost as thick as my wrist, what a magnificent ****! One of the things He kept telling me as He was ******* me deep...
    spjennifer spjennifer 46-50 4 Responses Oct 15, 2013

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    Lil Ab Me

    Ello all one very cute ab sissy here single 40 and very subby too i love a Mommy or Daddy or Dom tv or sissy to baby me very much so i love all pretty pink baby wear and love and adore terry nappys and yummy pink baby pins and pink baby reins ooh how i love to be in a baby life...
    sissymelissa69 sissymelissa69 36-40, T Feb 18, 2013

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    My Professor Saw My Panties!

    So like I said in my last story, I live a double life. By day, I am your average college boy, but by night I am a slutty sissy girl who craves the dominance of a strong man. But that doesn't mean that I don't like to mix it up a bit ;) I really like to wear my frilly pink...
    SandyAego SandyAego 22-25, T 2 Responses Mar 23, 2013

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    Pink Panty Humiliation Part 2

    My previous post, "Pink Panty Humiliation" was true.You should read that first.This is pure fantasy. Just what I dream of happening to my pink pantied sissy ***...Once he and my mom broke up, she asked me to go over to his place and pick up the rest of her things. I was taking...
    tinydickpantyboy tinydickpantyboy 26-30 1 Response Oct 24, 2012

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    Lovely Surprise

    Went to Grand Canarie before seperating with wife, and went to watch the drag show. I loved this and was quite horny. No toilets at drag show so off I went to a bar. (Gay Area) when I came out of the toilets I saw a dark room and my curiosity took me there. A naked white man...
    spaceman100 spaceman100 46-50, M 4 Responses Aug 31, 2011

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    Life Altering Road Trip?

    As some of you who may have read my other stories know, i have been a lifelong gay sissy and have never had sex with a woman, well almost...The other day i was remembering a cross-country road trip i made with my Mother and a friend of hers when i was 14 going on 15, Mom's friend...
    spjennifer spjennifer 46-50 2 Responses Oct 27, 2013

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    Related Experiences

    Schizophrenia is linked to homosexuality, now there's nothing wrong with being gay but I think it's obvious something is wrong when your body is attracted to the same sex, you won...
    alphadecay alphadecay 26-30, F 1 Response Sep 4

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    I hate who I am, I hate not having a choice. I hate that it feels like my life dreams of a family and getting married have been stolen from me. My attempts at trying to change this...
    pyroguy80 pyroguy80 31-35, M 1 Response 7 hrs ago

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    Being gay is not fun to me. I'm Muslim and I'm proud thank god but being gay has caused me nothing but troubles and misery. I wish I had a boyfriend but at the same time I hate the...
    Abdulaziz94 Abdulaziz94 18-21, M 4 Responses Aug 18

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    Schizophrenia is linked to homosexuality, now there's nothing wrong with being gay but I think it's obvious something is wrong when your body is attracted to the same sex, you won...
    alphadecay alphadecay 26-30, F Sep 4

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    Hi my names scummy girl I'm 14teen and a dirty lesbian girl, and I love being bullied by other girl's. I get bullied at school by older girls which I like a lot. They gave me...
    Bellathegorrilla Bellathegorrilla 13-15, F 7 Responses Aug 26

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    I just love being by myself. I have time to think. My friends keep trying to hook me up with thier friends. I hate it though. I love being able to have peace and quiet in my life...
    sfdrboy sfdrboy 22-25, M Aug 26

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    I love being completely naked on the beach, or at home and being totally shaved or waxed bald from head to toe, including eyebrows and eyelashes, makes it even better - as shown in...
    lifeuniverseeverything lifeuniverseeverything 36-40, M 3 Responses Aug 21

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    So it's me again. The guy that people seem to love to hate but I accepted the hate. I admit that a part of me miss having to think about someone else then me all the time. What I...
    ilikenetflix ilikenetflix 26-30, M Aug 30

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    I am his.I don't wear a collar but I wear pieces to signify my commitment to him.I do as he asks, willingly, affectionately and with great attention.I talk with him each and every...
    desirabledreams desirabledreams 46-50, F Aug 25

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    Literally on our doorstep is a vast once Royal domain called the New Forest. I love to go wandering alone in the forest to find images to draw, yes, but also just to enjoy the...
    DearbhalC95 DearbhalC95 18-21, F 2 Responses Aug 27

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