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I Want to Have Sex With a Sissy

Personal Stories, Advice, and Support 896 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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    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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    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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    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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    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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    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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    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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    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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    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 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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    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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    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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    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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    "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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    Related Experiences

    When I was really young there was a teenage girl with dwarfism in my neighborhood that I saw regularly. I don't think I was even old enough to like girls yet but there was...
    thatguythereoverhere thatguythereoverhere 26-30, M 2 Responses Jul 27

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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 1 Response Jul 22

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    I think i would be great to have sex with a trans women. They are really gorgeous but also independent in a sense. I'm not gay but I definitely want to go for a transvestite woman...
    lolzmeplz lolzmeplz 16-17, M 4 Responses Aug 4

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    I want to have sex with woman while my boyfriend partipates however he wouldn't **** her or lick her. She would lick me while my boyfriend ***** me and I would return the favour to...
    Readingaddict Readingaddict 18-21, F Aug 9

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    I really want to have crazy sex with my sister
    hornyharry123 hornyharry123 22-25, M 5 Responses Jul 30

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    This is something I want to try I have never even dated a black man much less had sex with one but there is a first time of every thing right ??
    1Miserablemind 1Miserablemind 18-21, F 8 Responses Aug 5

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    I'm a sexy black girl from PA ;)
    Rayven1997 Rayven1997 16-17, F 2 Responses Aug 10

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    I just turned 19 & I think it would be so sexy to be with a guy like 30-40. Experience is such a turn on and I bet someone that age would have a lot. That's like my biggest fantasy...
    wayyfarer wayyfarer 18-21, F 17 Responses Jul 26

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    I just think that trans women are so hot. Girl up top but guy down below. I don't know why I just think it's incredibly sexy.
    LadyCNote LadyCNote 26-30, F 3 Responses Jul 31

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    I just need sex to sleep at the moment!
    deklan deklan 31-35, M Aug 10

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    I'm only 19 year old girl, but I would love to have a sexual relationship with a 40-55 year old women and do sexual things with her (or without her) with her teen-age kids (if she...
    Jamielr13 Jamielr13 18-21, F 5 Responses a week ago

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    Well I owe my father something because he took the blame for something I did once! I think he wants me to blow him but I am not sure! I am bi but he doesn't know! How can I get him...
    jackbx jackbx 13-15, M 1 Response 6 days ago

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    Just want a little chocolate princess! Any takers message me!
    Hazza8989 Hazza8989 22-25, M 1 Response Jul 25

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    I would love to, just need to find a guy who wants it!
    bd693 bd693 18-21, M 2 Responses Aug 8

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

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    I so badly crave my friends boyfriend he's hot and possessive and dominant and I love everything about him and my friend is a ***** to me anyways and they have only been dating for...
    cootyboo cootyboo 22-25, F 3 Responses Jul 30

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    he's not necessarily attractive or anything. it's just something about his old school, authoritative look that really turns me on. I can just imagine it going like this: me: is...
    fuckinglife fuckinglife 16-17, F 1 Response 6 days ago

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    Would you go have me boys?
    mommygotboobs mommygotboobs 36-40, F 12 Responses Aug 7

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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 3 Responses Jul 25

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    My father is fat and hairy!
    Bulkver Bulkver 36-40, M Aug 13

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    But when I'm a little older, 14 is too young
    bisexuwhale bisexuwhale 13-15, M 1 Response Jul 26

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    the one who came by and talked about where he grew up
    liberty2 liberty2 46-50, F Jul 29

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    Anybody 14 and younger in south fl ;)
    djdicirnndksoxjfdjejx djdicirnndksoxjfdjejx 13-15, M Aug 9

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    My Spanish teacher is sooooo hot and she has the biggest noobs and is so skinny and young! I wanna **** her so bad!
    aidanmcshane6 aidanmcshane6 13-15, M 1 Response 6 days ago

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    LOFL! I see I'm not the only one.... that guy is good!
    BeyondTheSunset BeyondTheSunset 36-40, F 2 Responses Jul 25

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    We were both youn, started kissing and it almost happened on the floor watching a movie
    avengedwolf88 avengedwolf88 26-30, M 3 Responses Aug 8

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

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    I get turned on by pregnant women so would live to have sex with one
    goonteam goonteam 16-17, M 2 days ago

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    I've always wondered what it would feel like to have sex with a man in his late 30's or 40s. Guys my age are too selfish in the sack and brag too much. Note to men: if you feel the...
    naughtybutnice22 naughtybutnice22 22-25, F 11 Responses Jul 29

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    I Havnt actually had an experience yet . My fwb and I have sext with couples and I find it Hott sexting with other females . It's fun when I'm at work and well my bf def gets the...
    Noismkr Noismkr 31-35, F 2 Responses Aug 13

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    All bookings should be produced inside of seven Performing times of invest in – no refunds thereafter. All travel need to be concluded by 15 February 2014. Reservation...
    Mary1062y Mary1062y 31-35, M 1 Response 18 hrs ago

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