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I Want to Have Sex With a Sissy

Personal Stories, Advice, and Support 890 People

    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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    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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    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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    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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    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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    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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    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 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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    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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    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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    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 10 Responses Nov 27, 2013

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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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    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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    "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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    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 have a gigantic crush on my teacher! He's so hot! Everything he does is hot! And he favorites me over a lot of people. He often jokes around with me, and he is not the joking...
    ihatemytown ihatemytown 13-15, F 1 Response 5 days ago

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    I dont know why but sex with teenagers, 14-18 is awesome. Something about teaching & showing them your naughty ways in a turn on.
    WhiteGirl702 WhiteGirl702 22-25, F 12 Responses Sep 28

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    I love giving oral sex to men women too
    ncline2 ncline2 46-50 6 Responses Sep 28

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    It happened, and I want to go into detail about it, but how can I do that without getting flagged? Can I type it up on another document and put the link up?
    teentwink teentwink 18-21, M 7 Responses Sep 21

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    Experience is something I want. 40+
    lexaaah lexaaah 22-25, F 11 Responses Sep 22

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    Talk to me and turn me on, I want to talk to all the older men out there;) so horny!!!
    maddieXxx maddieXxx 16-17, F 9 Responses Sep 26

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    I want it now. The big black co__
    Beachfam Beachfam 51-55, F 1 Response 2 days ago

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    Me too. I Want the bbc now
    Beachfam Beachfam 51-55, F 2 Responses 2 days ago

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    So I've had this crush on a guy for a little while and we have talked about doing it but whenever we are together I get super nervous and decide I don't want to but then after he...
    ascorby54 ascorby54 16-17, T 1 Response 2 days ago

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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 2 Responses Sep 20

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    Any guys want to do group with my girlfriend? Let me know!!
    BigBone90 BigBone90 22-25, M 6 Responses Sep 23

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    Or become friends with maybe swap pics with any on here
    Steinjoshu Steinjoshu 22-25, M Sep 28

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    I have thought about what it would be life to have a women embrace me go down and all of it. I have only been with men and I cant get the thought out of my head
    curiousegirl curiousegirl 22-25, F 1 Response Oct 6

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    Might do it with a guy for the first time this weekend. Obviously I'm kind of nervous. Any advice?
    zacktr zacktr 41-45, M 6 Responses a week ago

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    I really like big boobs, I also have big boobs, who wants to trade boob photos, mine are 38k
    Cleavage5997 Cleavage5997 16-17, F 4 Responses 3 days ago

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    My girl needed a ride into vegas one time and she ended up getting picked up by a car with three guys in it and she went down on all three of them on the way to the city
    BigBone90 BigBone90 22-25, M 1 Response 3 days ago

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    If love to have a bf that was cool with me ******* other guys.
    Ladyay11 Ladyay11 31-35, F 2 Responses 2 days ago

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    Any fun ladies in uk wanna chat pm me bk?
    TeddyboyUK72 TeddyboyUK72 41-45, M 15 hrs ago

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    I'm 30 so if you enjoy this age then message me ladies ;)
    heartgun heartgun 26-30, M 1 Response Sep 26

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    I love my cockk sucked tell I cuxxm
    Masterlicks Masterlicks 31-35, M 1 Response Oct 2

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    send link of any **** movie
    cramasamy1965 cramasamy1965 18-21, M 3 days ago

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    I'm ready to explore this...
    Ladyay11 Ladyay11 31-35, F 1 Response 1 day ago

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    She so good in bed mmmmmmm
    gator2213 gator2213 41-45, M 4 Responses 4 days ago

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    I love ******* random men. The generous ones are the best.
    Ladyay11 Ladyay11 31-35, F 1 Response 1 day ago

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    She is such a pretty little thing. Inbox for details.
    fuckmylilprincess fuckmylilprincess 56-60, M 3 Responses 1 day ago

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    So I’ve been in this weird friends with benefits relationship with a guy. Over time I secretly developed feelings for him and we’ve been texting each other excessively...
    Maude01 Maude01 22-25, F 4 Responses 6 days ago

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    I want to have sex with my school's mascot. I've never seen him without his outfit on, but I would want to do it while he was still wearing it. The way he's so fun and flirty at...
    Beccalei12 Beccalei12 22-25, F 5 Responses Sep 27

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    I tried to have sex with my young cousin
    secretboy12 secretboy12 16-17, M 1 Response Oct 5

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    I've noticed that i have the temptation to always have sex with out a condom. To the women out there, do you mind the "pull out" method?
    Smokingskater Smokingskater 18-21, M 3 Responses Sep 25

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    I love sex nights. My husband is ex marine and use to a very detailed schedule . Everything about our life is scheduled. On Sunday evenings he issues the weekly schedule. It has...
    Rosebud123987 Rosebud123987 36-40 1 Response Oct 2

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    Everybody wants a sexy car ;)
    YuriXWolfram86 YuriXWolfram86 18-21, F 1 Response Oct 11

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