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I Want to Have Sex With a Sissy

Personal Stories, Advice, and Support 895 People

    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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    "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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    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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    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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    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 8 Responses Nov 27, 2013

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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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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 my name is Jan I am 21 and have sex with lots of guys. I work at a bar and always bring guys back to my place after work and have sex with them. I have a no condom rule. I want...
    jantheslut jantheslut 18-21, F 8 Responses Jul 17

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    This year, I had a extremely attractive chemistry teacher. He's sweet, and has vibrant blue eyes, short blonde hair and a perfect body. Every time that I would look at him, I...
    Jeanpocket Jeanpocket 13-15, F 3 days ago

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    I would love to have sex with a black women never done it I am so girly right now I will eat eat that p up
    dmedina513 dmedina513 36-40, M 2 Responses Jul 5

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    I have dreams about having sex with my father.
    Bulkver Bulkver 36-40, M 4 Responses Jul 12

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    My dog is the first living thing I've ever had sex with, she was tight, but then I let my friend borrow her and he ripped her a new *******. But moral of the story is, does anyone...
    Guuuu Guuuu 18-21, M 5 Responses Jul 17

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    I have been having sex with my daughters mum for years. I think it's time to stop.
    usernamesareashame usernamesareashame 46-50, M 1 Response Jun 28

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    Just want a little chocolate princess! Any takers message me!
    Hazza8989 Hazza8989 22-25, M 3 hrs ago

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    There's this guy on tinder, he's older, nearly double my age, he's not that hot but decently attractive I'm looking for more guys on tinder but don't know if it would be too bad to...
    hardcoregay hardcoregay 18-21, M Jul 5

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    One thing I want to try is getting ****** while I **** a guy. That sounds mind blowing...
    hardcoregay hardcoregay 18-21, M Jul 5

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    I want to suck a guy so badly.
    zacktr zacktr 41-45, M 1 Response Jul 6

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    Not sure if I'm bi or just bi-curious but I've known four guys in my life that if they wanted me to suck them off, I would. How do you bring that up with people that are definitely...
    zacktr zacktr 41-45, M 5 Responses Jul 8

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    I am in high school and this year i really fell in love with my gym teacher and just wanted to have a relationship with him. I just felt i needed someone there to talk to and he...
    soccer2117 soccer2117 16-17, F 1 Response Jul 10

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    Looking for transsexual to **** me I have look every where and I'm so horny for it I just want you now :)
    horny4younow horny4younow 22-25, M Jul 14

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    Want a black girl to talk sx with me I'm so h-rny
    dmedina513 dmedina513 36-40, M 1 Response 5 days ago

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    Want to sx chat with younger girl
    dmedina513 dmedina513 36-40, M 1 Response 5 days ago

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    I ran into a good friend that I haven't seen for several years. He went through a long drawn out divorce and dropped out of sight after that. He hasn't remarried and says he's...
    stillhavingfun123 stillhavingfun123 51-55, M 3 Responses Jul 2

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    My dad is a very straight acting man. VERY. He always walks around the house in his boxers and I can always see he has a bulge poking
    jdragon1704 jdragon1704 16-17, M 12 hrs ago

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    LOFL! I see I'm not the only one.... that guy is good!
    whatyathinkaboutthat whatyathinkaboutthat 36-40, F 17 hrs ago

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    Yeah this could work....hmu
    Sinjintiger Sinjintiger 41-45, M Jul 5

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    I'm 16 and love older men!
    primadonna1 primadonna1 16-17, F 7 Responses Jul 13

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    I wish to try it <3 <3 <3 <3
    confusedbi0 confusedbi0 22-25 1 Response Jul 14

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    My ex dumped me and then started seeing some guy just two weeks later. What she doesn't know is one of her best friends has already agreed to screw me, and the other is influenced...
    Warner216 Warner216 18-21, M 3 Responses Jul 1

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    Would love to have Sex with a pregnant woman would be a great turn on
    Hazza8989 Hazza8989 22-25, M 3 hrs ago

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    Okay I live in Michigan and the age to consent to sex is 16 I'm guessing that's with any age but below 16. Anyways this 42 year old police officer who lives in Canada came over the...
    cupcakes38 cupcakes38 18-21, F 3 Responses 6 days ago

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    Okay I live in Michigan I was 17 now 18 at the time and the age to consent to sex is 16 I'm guessing that's with any age but below 16. Anyways this 42 year old police officer who...
    cupcakes38 cupcakes38 18-21, F 2 Responses 6 days ago

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    I want to have sex with a big women so I could sexually pleasure her hit me up
    dmedina513 dmedina513 36-40, M Jul 4

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    I've only had sex with one girl. And it was amazing!!!! I like boys and I'm sure one day I'll find the right one
    Randi97 Randi97 18-21, F 2 Responses 6 hrs ago

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    i have sexual attraction towards my son////
    elinarose37 elinarose37 36-40, F 3 Responses 8 hrs ago

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    i keep trying to tell my mum that i don't know any more. when i was little i always wanted to be a nurse but after being rejected from university 3 times and 3 other ones not even...
    makeitsomeday makeitsomeday 18-21, F 4 hrs ago

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    I would really appreciate some input here, i know this is kind of long but I would be glad to hear from anyone who has any advice for me. I'm 18 years old, I just graduated from...
    sidkyd99 sidkyd99 18-21, F 5 Responses Jun 25

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    I am 16 and have wanted to have sex so badley since I was 13. I am now legal so I just want to do it. I need a girl of any build but a nice personality :) message me or heart this...
    goonteam goonteam 16-17, M 2 days ago

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    One of the prerogatives of being faithfully married for so long is to have sex unprotected. Condom ads can lie what they want.
    pacodad pacodad 70+, M 2 Responses Jun 25