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I Want to Have Sex With a Sissy

Personal Stories, Advice, and Support 895 People

    Me Too Sounds Like Fun.

    i am for all intents and pourposes a female.oh sure i still have all that male equipment hanging down there but i would love to have  a sissy friend to play with some time.I am into all kinds of sexual play so it        would be exciting to...
    aniowagirl aniowagirl 66-70, F 3 Responses Jan 28, 2010

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    It's Going To Happen One Day Soon

    I have often fantasised about having sex with a sissy, well, it looks like it may now happen sooner rather than later. I've been in contact for a while now with a CD, who is submissive, and loves to be a sissy. I have photos of my sissy, dressed in gorgeous, frilly pink outfits...
    kiwicd kiwicd 56-60, M 1 Response Apr 1, 2011

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    Sex With A Sissy

    just love having sex with a sissy!!1 being a sissy myself just love having sex with another sissy!!! starting dressed and kisses each other and slowly stripping down to free our sissyclitties!!1 starting then with 69 each other and french kissig our ***.later ******* each other...
    mandiejune mandiejune 51-55, M Jan 30, 2010

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    The Hole Filled And The Hole Left Behind

    This is a long story, mainly just getting it out there, if you're wondering what I'm about and what I'm into then feel free but this is mainly just to formalize and express what I'm feeling. It wasn't a new feeling. I'd been addicted to sex since I first learned to get myself...
    weapon33 weapon33 26-30, M 9 Responses Nov 27, 2013

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    Wanting

    I would absolutely love to meet up with a sissy and have lovely, messy sex. *** or mouth I don't mind but I would love feel a lovely sissy **** up my willing *** but only after I'd given it a good sucking. It must be great to feel a **** spurting deep inside. Then I'd turn her...
    deleted deleted 26-30 1 Response Oct 15, 2013

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    Gay Like A Girl

    that's would be fun two of us gay like a girl!  That would make us t-lesbians or something like that!   How much more gay could it get than two sissies going at it!
    haileeTV haileeTV 41-45, T 1 Response Jan 14, 2010

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    Do Masculine Guys Like Real Sissies?

    I know there are lots of guys who love cds, tvs, tgs... but I find it rare to come across a guy who really loves sissies who love to dress in pink little girl dresses with lace and ruffles, hair in ringlets. This is how I really love to dress but have yet to meet a...
    berlinsissy berlinsissy 46-50, M 6 Responses Jun 19, 2009

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    Submissive, Sissy, Sex

    Submissive, Sissy, Sex I am really into fantasy fulfillment not just my fantasy but also others. It takes too or more people to have a fantasy. It is one people fantasy so he is in charge and it is up to the other person to play the part to make the fantasy come true. I have...
    cindyusa58 cindyusa58 56-60, M Feb 15, 2012

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    I Think True Pretty Sissies Are Just Wonderful

    I would just love to take a lovely sissy to bed and treat her like the princess she truly is. I just love pretty, feminine sissies, I think there wonderful Kisses Dennis / Denise
    deleted deleted 26-30 4 Responses Feb 8, 2010

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    My Dream

    It is what I want both dressed to the nines while I slip her panties down and begin to kiss her beautiful **** taking it hungerly in while two women watch siting on the sofa commenting how cute a couple we make.
    deleted deleted 26-30 1 Response Mar 17, 2010

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    Girls Who Want To Have Fun

    I want to meet a cute sissy who wants to hang out and play. We could spend the afternoon playing dress ups, then do our hair and make up, and make ourselves look super cute and sexy. We could put on hot lingerie under our cute little skirts and tops, and slip into some sexy high...
    deleted deleted 26-30 1 Response May 12, 2013

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    I Dream Of Pretty Sissy In The Lonely Night

    There are some stunning sissies on YouTube, really lovely sweeties whom I dream of fulfilling - LUSCIOUS !
    Faggtattue Faggtattue 36-40 2 Responses Aug 25, 2012

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    Pretty, Obedient Sissies

    The times I have ****** a sissy were forays into the Domme side of BDSM. I'm normally sexually submissive to men, but a few men have revealed not only their desire to be dominated, but that they were closet sissies, with a desire to wear pretty lingerie and be dressed as women...
    auroramaru auroramaru 46-50, F 10 Responses Jan 17, 2011

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    New To This

    I've always known I was small -- just under five inches hard. It never really bothered me, since I only have one and can't do much about it, but I've always secretly found it very exciting. At the gym, I'll often see guys who are larger soft than I am hard, and think to myself...
    Chastesub Chastesub 41-45, M 1 Response Apr 4, 2011

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    "i Had Sex With A Sissy"

    I found out one night that a friend on mine was a crossdresser and liked to suck dicks. We arranged to meet one night and get dressed up together. I got dressed and waited for him to show up. He finally got there and went into the bedroom to change. He came back out wearing a...
    davis36a davis36a 61-65 5 Responses Dec 19, 2011

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    Two Sissies Meet For The First Time

     I love being a sissy!   I met another sissy in my area through the Internet. Last Monday we met for the first time in person. He does live about 140 miles away, so it took some time for us to be able to meet up. It was simply amazing! We talked for a...
    mikesissy mikesissy 41-45, M 2 Responses Apr 3, 2010

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    Curiousity

    I think I am curious about this, but not sure I would go through with it. I like the idea of being with a softer guy and being "the man" but I am not sure I would be comfortable... 
    dougbi dougbi 41-45, M 4 Responses Sep 27, 2009

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    Related Experiences

    hi i am from new delhi india i want to have sex with a sexy girl i will pay her gd bt i dnt hv ma prsnal place to **** plz help me out wht to do
    sexyboy034 sexyboy034 18-21, M 1 Response Sep 2

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    I want to have sex with a female teacher in my school teaches maths,she's not attached and is only a mere 22 years old she has an a body like an hourglass,all the curves in the...
    TheGamechanger TheGamechanger 18-21, M 1 day ago

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    Even though we don't have a label on our relationship, I still want to have sex with him and kiss him and hug him and cuddle . I like the way he feels inside of me . I don't know...
    neuroticgal neuroticgal 22-25, F 3 Responses 6 days ago

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    I love my dad more than anything and wish I could have sex with him.
    JeremyCooper JeremyCooper 16-17, M 3 Responses 2 days ago

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    My girlfriend has been having sex with other guys, about 2 of them she had sex with multiple times
    jma13f jma13f 18-21, M 2 Responses Sep 7

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    I'm going home today from college to spend time with my dad. Hopefully something will happen. Will update.
    teentwink teentwink 18-21, M 1 Response 4 hrs ago

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    My ex and I broke up a couple of months ago, and while I don't want him back, there is still something there that makes it hard for me to stay away from him completely. The thing...
    PepperF PepperF 22-25, F 3 Responses Sep 9

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    Godd its a big big want of mine , i just cant tell you how often i think about it and want it ...
    Yungbug Yungbug 18-21, F 2 Responses 5 days ago

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    I want a hermaphrodite to **** me xxx
    sassss52 sassss52 22-25, F 1 Response Aug 20

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    Or cyber with :) the older the Better come and get me
    Happiness412 Happiness412 18-21, F 5 Responses Aug 27

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    I have. It was awesome she was blonde
    lotsoflove12 lotsoflove12 31-35, M Aug 31

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    I want to suck a guy. I love the thought of having a guy in my mouth. Would also like to bottom for the correct guy.
    MITUK MITUK 36-40, M 3 Responses Sep 9

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    I have a deal for yu if yu willing to listen go read my experiences plz and inbox me serious ppl onli!!!
    ih8beingyung ih8beingyung 18-21, F 1 Response 5 days ago

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    Mmmm with a fat **** yummy
    lostgirlbree lostgirlbree 22-25, F 1 Response 5 days ago

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    I am so horny and want to have s e x with older man like 40's-60's. ;)
    Elizabeth214444 Elizabeth214444 22-25, F 1 Response 3 days ago

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    A older guy.. Better or worse??
    BeauteFloue BeauteFloue 22-25, F 3 Responses Aug 28

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    I live in Michigan and looking for some fun if there is any out there let me know
    Gunnera87 Gunnera87 26-30, M Aug 28

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    I mean I'm black Too So why not 😩🙌you know black guyssss got that big ____
    MisMisMis321 MisMisMis321 16-17, F Aug 30

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    My dad is hot. I like it when he touches me.
    gayandproud13 gayandproud13 13-15, M 7 Responses Aug 31

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    It was a sleepover, he crawled into my bed. He got on top
    lotsoflove12 lotsoflove12 31-35, M Aug 31

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    Someone message me so horny
    maddieXxx maddieXxx 16-17, F 5 Responses Sep 6

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    I'm 16 and I love older men and women 😋
    jhopegirl jhopegirl 22-25, F 1 Response a week ago

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    I hate how ppl who don't know me look at me and think I'm not a virgin...like wtf? And I hate how some people I know always tell me "just do it" "you're too pure" "gotta do it...
    Midnightangelx Midnightangelx 16-17, F 1 Response 6 days ago

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    I want to have sex with one so bad, like 14-15. (Im 16 btw, it wont let me change it)
    Gaywhore9 Gaywhore9 18-21, M 2 Responses 3 days ago

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    I have sex with my cousin all the time do you want to hear the stories ? ;)
    Vannnessaaaaa Vannnessaaaaa 18-21, F 26 Responses Sep 7

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    Any girls in Birmingham ..I want to have sex with a girl! Btw I love older women
    Babyk31 Babyk31 16-17, F Sep 6

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    I was a virgin on my 18th birthday, graduation day, and on my wedding day too. On my wedding we tied the knot, had a great wedding reception, went to our honeymoon destination...
    heatherinarizona heatherinarizona 31-35, F 3 Responses Aug 25

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    I love having sex!! I love trying new positions and every kind of stuff when i'm having sex. I'll really have sex on top of a tv lol
    Nathaly22 Nathaly22 18-21, F 17 Responses Sep 10

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    I love having sex with my boyfriend. We have the best sex ever!! I belief sex is very important in a relationship.
    Nathaly22 Nathaly22 18-21, F 4 Responses 6 days ago

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    I love sex without protection! Love to feel every ridge and vein. Ask me more in the comments and I'll answer... Gotta avoid those that watch since they are blocking my stuff now...
    catiemae87 catiemae87 26-30, F 26 Responses Aug 25

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    I want to talk with anyone about... I dunno, stuff. The new boots I just bought, or the guy at work I like or whatever, I dunno. I DON'T want to talk about your penis, sex...
    CaseyGirl97 CaseyGirl97 16-17, F Aug 28

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    I love sex without protection, love being inside a women, and feeling every sensation....
    red1235 red1235 41-45, M Aug 31

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