Post
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Want to Have Sex With a Sissy

Personal Stories, Advice, and Support 901 People

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    "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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    Related Experiences

    I've always wanted to have sex with BBWs. I want to explore the whole body of a woman who is 200+ lbs, and tongue her holes before going in her and pounding her like there's no...
    MoaXing MoaXing 16-17, M 3 Responses Apr 6

    Your Response

    Cancel
    I want to have sex with her she's 15 and has a great body
    comeatmebruh623 comeatmebruh623 26-30, M 1 Response Apr 15

    Your Response

    Cancel
    Looking for anybody in the north uk who is looking for a male to have sex with his wife
    genukmale11 genukmale11 36-40, M 2 Responses 1 day ago

    Your Response

    Cancel
    I had sex with my husband yesterday! Sad thing we are in the middle of divorcing one another! I was just so desperate for sex... That I asked him for mercy sex... Gosh I hope I...
    just2lovelee just2lovelee 41-45, F 1 Response Apr 11

    Your Response

    Cancel
    I want to hear stories and see pictures of people having sex with animals!
    Cameltoelove Cameltoelove 22-25, M 3 Responses Apr 15

    Your Response

    Cancel
    I want to have se*with my sister. She's 19 and I'm 22. She's tall has a banging body. Nice a$$ and perky t:ts. I constantly think a About asking her to have se* when we are home...
    Libbey91 Libbey91 22-25, M 2 Responses Mar 26

    Your Response

    Cancel
    Looking for any females who live in the uk who are interested in meeting up for hot sexual encounters. I'm honest genuine and very horny. The idea of just meeting up with strangers...
    genukmale11 genukmale11 36-40, M 21 hrs ago

    Your Response

    Cancel
    Like, it's on my bucket list! I find it interesting and sexy.
    ReeseThompson0424 ReeseThompson0424 18-21, F 6 days ago

    Your Response

    Cancel
    I just really want to suck one, I don't know why.
    MakeMeKing MakeMeKing 22-25, M 4 Responses Mar 30

    Your Response

    Cancel
    Recently I discovered that I enjoy her relationship with other men. I even want to see her have intimate relationship with them. This I realized when I saw her sharing some adult...
    rimpi1972 rimpi1972 41-45, M 5 Responses Apr 8

    Your Response

    Cancel
    I have dated black woman before and it was great . Lately it been impossible to meet black woman
    mruiz252 mruiz252 41-45, M 1 Response Mar 29

    Your Response

    Cancel
    I love bbw, I have ever since 5th grade. My teacher was a very large black lady with rolls on her thighs. I remember touching myself through my shorts because of the way it made...
    bbwlover30265 bbwlover30265 26-30, M 2 Responses Apr 3

    Your Response

    Cancel
    My wife and I have only fantasized about her sucking another man off as I **** her
    bbking88 bbking88 36-40, M 12 Responses Apr 8

    Your Response

    Cancel
    Over the road, driver would love to hook up with horny bbw
    DriveHardDave DriveHardDave 51-55, M 1 Response Apr 14

    Your Response

    Cancel
    I find this very intriguing, seems kinda hot and fun...
    92youngforever 92youngforever 18-21, F 1 Response Apr 4

    Your Response

    Cancel
    Let's make it easy... I tell you about me you tell me about you. I choose the place I pick you up I feed you and then I **** you outside my car, inside my car, at a restaurant, at...
    youguyssuck69 youguyssuck69 18-21, M 1 Response a week ago

    Your Response

    Cancel

    Your Response

    Cancel
    That would be great specially if he about nine inches or so that feel great
    iluvlezgal2 iluvlezgal2 41-45, F 6 Responses Apr 3

    Your Response

    Cancel
    the reasons why i dont want to do anything sexual before marriage : reason number 1 : what if i had sex with my girl friend before marriage , and after few days i met with...
    lifetriangle lifetriangle 22-25, M 7 Responses Apr 15

    Your Response

    Cancel
    My parents struggled with their marriage when I was in high school, after that I realized I wanted a stable, happy relationship, and never wanted to cheat or be cheated on... I saw...
    chiquita55 chiquita55 18-21 Mar 27

    Your Response

    Cancel
    I am looking for girls to have sex with and it's terrible bc 1 I can't find a girl 2 I live in Cranston and 3 idk I'm at the right place lol
    DaveP13 DaveP13 18-21, M Mar 24

    Your Response

    Cancel
    I think one complete the other one,cause when you have sex with love it should be the most amazing feeling ever.
    miserableamy miserableamy 16-17, F Mar 25

    Your Response

    Cancel
    Like I've said before. We've been married 6 years and it gets better and better. It's really heated up when we bring other women into the bedroom. I never thought I would enjoy...
    redhot1221 redhot1221 36-40, F 5 Responses 1 day ago

    Your Response

    Cancel
    I want be a feminized sissy wife for a hot gentleman. I want to be his feminine partner and companion. I would make him dinner in sexy outfits, give him spontaneous, non...
    erintgirl erintgirl 26-30, T 1 Response Mar 30

    Your Response

    Cancel
    We have been married for 15 years and wanted to see how to have sex and watch sex via a web cam. You have to be sexy, we are! in good shape, and willing to show us how to do it...
    just4fun3 just4fun3 41-45, M 1 Response Mar 27

    Your Response

    Cancel
    Okay so it's actually a little different. For some reason I can not figure out how to add my own experience if I can, but anyway... I had sex with my friends dad... I am a little...
    speaksoftandcarrybigstick speaksoftandcarrybigstick 16-17, F 2 Responses 3 days ago

    Your Response

    Cancel
    I want a sex change more and more and more than I have ever wanted anything else. I would love to be a woman for the rest of my life and it pains me that I can not be a woman right...
    wtbwoman wtbwoman 41-45 4 Responses Mar 24

    Your Response

    Cancel
    it's been three weeks i have had no sex, i look for a good man, love me first, then we can have sex, that is what i want to. so hard that to get it??
    tanglelau tanglelau 31-35, F 1 Response Apr 11

    Your Response

    Cancel
    I have something called "Frenulum Breve" and "Phimosis". having those conditions make it impossible to have sex. Becoming 30 years old this year would make me sort of a 30 year old...
    MAGH2 MAGH2 26-30, M 1 Response 5 days ago

    Your Response

    Cancel
    As I prepare to go as Lucy full time, I find myself reflecting on the road ahead. I have wanted a sex change operation for many years now and I know it is the right decision...
    LucyTG LucyTG 26-30, T 3 Responses 1 day ago

    Your Response

    Cancel
    Never had sex with a black woman but I want to.
    andykenny andykenny 26-30, M 1 Response Apr 9

    Your Response

    Cancel
    am 18yrs old both my parents deceased have a older sister 40ish,i have 2babies 1and3,my sis takes care of my babies I support them being a exotic dancer my brother inlaw joe was...
    ralphbruno ralphbruno 56-60, F 2 Responses 2 days ago

    Your Response

    Cancel
    I like having sex with out pertection
    izac31 izac31 18-21, M Mar 31

    Your Response

    Cancel
    I love sex without protection message me and I will tell you why(;
    Hellogoodbye85 Hellogoodbye85 18-21, F 33 Responses Mar 31

    Your Response

    Cancel
    I went to one of her fashion shows and I got invited backstage to meet her. When I got there I saw her she was wearing a bikini, anyway I said hi and she said hi back, I kept...
    Ladiesman93 Ladiesman93 22-25, M 2 Responses a week ago

    Your Response

    Cancel
    Whenever I have sex, I can't stand to use protection. I love feeling skin on skin and I love to feel him release inside of me. I love feeling so full of him.