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I Fantersise About Sex With a Shemale

Personal Stories, Advice, and Support 1,639 People

    Weight Lifter Want Hot She-male ****

    Hi,im basically straight,but when i was younger im 52yrs.i would go to bars looking to meet woman and i the interm,id get pleasantly drunk.if i was unsucessful in ***** hunting,i would go to the gay-baths to get my fill of T>L>C> thick long ****,also i would sniff poppers a lie...
    jwkelly1959 jwkelly1959
    36-40
    Jul 17, 2011

    Dreams

    IT SEEMS THAT EVERY DAY WHEN I HAVE A FREE MOMET AND THE THOUGHH OF HAVING SEX ENTERS MY MIND I SEEN TO ALWAYS PICTHRE MYSELF IN THE FEMININE ROLE SINCE I ALREADY WARE WOMANS CLOTHS I WOULD LOVE TO HAVE A MAN TREAT ME ASĀ  HIS FEMALE SEX PARTNER AND FOFILL MY FANTICY AND MAKE ME...
    deleted deleted
    26-30
    1 Response Feb 2, 2012

    Only Time With A Shemale

    I have been with a shemale one time. At the time, I was still new to anal play, and my *** was very tight. We kept trying to get her **** in my *******, but it was just to painful. We finally ended just sucking each other off and ******* in each others faces. I have been playing...
    jimdavis33 jimdavis33
    31-35, M
    3 Responses Jul 23, 2011

    Not Sure Just A Fantasy

    I have posted ads on CL, and tried to answer other ads, but most people on there seem to be gay men or hookers. But I would love to be with a t-girl!
    spearot32 spearot32
    36-40, T
    1 Response Aug 8, 2013

    Want A Shemale To Dominate Me

    I'd love to be dominated by a shemale. Tied up really tight and kneeling before her. I am dressed as a slutty french maid. I am forced to suck her **** all night and foced to take it up the *** too.
    XBFUL1973 XBFUL1973
    36-40, M
    1 Response Oct 10, 2012

    Fantasize Of Being With A Shemale

    I am a happily married man that has a secret i never told anyone.  It was prolly about 10 years ago when i first found out about a shemale. and ever since then i have been fantasizing about being with one. having her **** pressed up against mine, while kissing on her breasts...
    bobbysim32 bobbysim32
    26-30, M
    3 Responses Jan 25, 2010

    Shemale Maid

    When I was younger(about 16) my parents had a maid that would always spend extra time in my room. I came home early and wanted to get to my room to watch some **** and jerk off since my parents were out of town. I got inside and walked into my room to find something that made my...
    destroyerbrad destroyerbrad
    18-21, M
    2 Responses Dec 31, 2012

    Panties64

    I would love to have a shemale throw me down on the bed on my back fold my legs over my head as she looks at my face and **** me long , hard and repeditly.
    panties64 panties64
    41-45, M
    2 Responses Apr 22, 2009

    Baby Soft ****

    I have fulfilled this fantasy and having sex with a Shemale is ****** amazing. What could be better than a beautiful girl with large succulant breasts and a nice **** - smooth and hairless and ready to be sucked. A beautiful women with a **** - sounds much better than a man. The...
    CaraJ CaraJ
    41-45
    13 Responses Sep 6, 2008

    How It All Started..

    One evening I entered a sex shop to buy a new vibrator to play with the wife. As I was looking at some vibrators one of the sexiest hookers I have seen came up to me and asked me what I am thinking on buying, I mentioned that I am looking for a vibrator and she asked if I wanted...
    nightlooker nightlooker
    31-35, M
    3 Responses Dec 13, 2011

    New Experience

    Hello All, I'm a 34 Year Old experienced Dom. While I consider myself a lesbian I am very intersted in being with a shemale. By that I mean someone who is actually a T-girl, not a guy dressed in womans clothing. I would love to take an actual T-girl as my slave. Your Queen...
    MistressTiffany12 MistressTiffany12
    36-40, F
    Oct 17, 2013

    Nothing To It

    I'm sorry to say that I have no story, that is no experience. When I first began checking out shemales on line it is because I am a genderqueer and would love to become a shemale. Sadly, there are problems that makemy being out on H.R.T. impossible at least for the moment.However...
    deleted deleted
    26-30
    1 Response May 22, 2013

    My T-girl Lover In Orlando

    I grew very tired and restless in my marriage of over 20 years. For many years I had always dreamed of finding an Asian Transexual, and meet up with her and have great sex. I had always thought the experience would round out my sexual experiences and I craved the day that I would...
    klandestine313 klandestine313
    41-45
    3 Responses Sep 12, 2011

    My First Time Fantasy With A Shemale.

    We would meet by what ever random chance of nature, mutualy attracted. Her sexy girlish curves and silky hair. Once we get alone we take are time to explore one anothers bodies with our hands and mouth, we kiss a lot. We peal off the clothes one peice at a time but I leave her...
    Karn01 Karn01
    41-45
    1 Response Jun 4, 2011

    Just Curious...

    I often find myself with my phone in hand looking at shemale ****. You should also know that i can almost suck my own ****, which is another thing google is pegged on my browser. Im always wondering why more shemales in the **** industry dont try to suck themselves off. I mean, i...
    rollingrock8990 rollingrock8990
    22-25, M
    Jan 5, 2013

    Both parts

    If you had a ***** and other female parts in side along side your penis would you like to have sex both ways , penetrate and be penetrated?
    wilt575 wilt575
    41-45
    1 Response Aug 27, 2011

    Corruption...hehe (fantasy)

    This is my ultimate fantasy; My husband and I have always spoken about having a ********....he always said we could have a ******** with a MAN, provided he didn't **** my ***. here's my take on the situation...one i would never tell him.... We are at home, its mid evening...
    deleted deleted
    26-30
    Aug 17, 2011

    Me Too

    i am straight and i watch shemale **** and sometimes fantasize about what it would be like to be with a shemale but having had a couple of opportunities to be with a shemale i have always changed my mind in the end and for me it will always remain a fantasy as i would not be able...
    Jan 31, 2013

    I Fantasize About Being ****** By A Shemale

    i want to have sex with a shemale because just the thought of a woman with a **** turns me on but she would have to have big **** and a big ****. i want her to put my legs above my head and pound my *** while i rub on her **** and then i want her to *** on my face then i want...
    gmurphy69 gmurphy69
    18-21, M
    Mar 12, 2010

    Best Of Both Worlds

    I've slept with two. It was a lot of fun. They both were Asian, gorgeous and a *********. Because of the mones and impending surgery, it took a long time for them to ***. There is nothing like two girls blowing you at once. But, this was two pre-op transsexuals. Shemale isn't a...
    lalliek lalliek
    36-40, M
    Jan 2, 2013

    My Wife And I Are Wanting The Experience

    this is what we really wish for. we have had long talks. talk is over now we want experience it with you, game night?lets become friends and get to know each other
    daywane daywane
    46-50, M
    Aug 29, 2011

    A Couple Times

    I've only been with two of these amazing human beings. The first one was a brief encounter, but the second was incredible. She was about 6' tall, had brown hair, and a full figure. Carrying on conversations with her was always a pleasure, but when it moved to the bedroom, I...
    roberto1588 roberto1588
    22-25, M
    3 Responses Jul 5, 2010

    It'S About Need

    I think one of the reasons I fantasize about sex with a shemale is because whenever I am with a woman, kissing, licking, touching and everything that comes with good, delicious lesbian sex, my body is always more or less screaming for a **** after I have had an ******. And a...
    MonaDekadent MonaDekadent
    46-50, F
    3 Responses Jun 5, 2013

    Panties Filled With C**k

    I just love the sight of c**k and Ba**s filling a pair of panties. I get really turned on by pic's of shemales and then fantasise about holding that stiff c**k in my hands, and ********** the person. This has become a goal in my life and really would love to experiance it one day...
    Bateleur11 Bateleur11
    46-50, M
    1 Response Nov 17, 2009

    It Would Be A Dream Come True..

    I was sexually abused as a boy and an still homophobic as hell so why I dream about sleeping with a transsexual is something I will never understand. My story is when I was younger I drove a taxi at night and went to school during the day and the dispatcher would send me to pick...
    LTR1948 LTR1948
    61-65, M
    1 Response May 27, 2012

    Labels?

    i never really knew what to classify or label myself has except a girly guy. I have dressed femme on and off since i was around 6 years old. It started off with clothing mostly...but the older i got the more i wanted to be more a woman than a guy. That being said i married a...
    rachealfoxxe rachealfoxxe
    41-45, T
    24 Responses Mar 28, 2011

    I Want To Marry A Shemale

    I'm a Bi man I always Fantersise about Shemale's and as I love Boobies & **** and my family don't know about this side of me I could still hide it from them if I was to marry a Shemale that sounds & looks like a female.
    woopisingle woopisingle
    46-50, M
    May 21, 2013

    Been a Childhood Fantasy For a Long Time

    I have been having random fantasies from the time I was 11 when I saw a nude magazine shoot featuring an incredibly sexy transgendered woman. Never actually had the chance to engage in this but I would if I could...
    samantha72t samantha72t
    36-40
    16 Responses Sep 26, 2008

    Lactating Shemale Make Your Fantasy Come True!

    Hi, Rachel Here, I am a lactating shemalel,I get so horny when I do manual nipple and breast stimulation ( 4 or 5 times a day) or use my breast pump. I got into lactation because as a Shemale I wanted real breasts, I took a course of natural hormones which worked superbly to...
    femi9 femi9
    46-50, T
    2 Responses Mar 7, 2010

    Sex With Shemales

    just love sex with a shemale the so sexy fem body but a hard **** too so very good! love the fem body and **** combination so very hot!1 being a sissybitch love to be with a shemale so very hot and sexy!!!!!!
    mandiejune mandiejune
    51-55, M
    1 Response Feb 23, 2010

    I Didnt Thik ,It Be So Huge

    it was so big and huge.she came in my room and showed it to me.
    shirazi1970 shirazi1970
    46-50
    May 28, 2013

    My Wife And I Are Wanting The Experience

    this is what we really wish for. we have had long talks. talk is over now we want experience it with you, game night?lets become friends and get to know each other
    daywane daywane
    46-50, M
    Aug 29, 2011

    Lovely Ladies With Somethin Else

    I'm not sure what it is, but there is something strangely sexy about the thought of getting ****** by some gorgeous shemale. I've always gotten horny watching the ****** with shemales going at it with women, since, interestingly enough, shemales getting it on with guys doesn't do...
    deleted deleted
    26-30
    3 Responses Nov 17, 2009

    ********* - Real Story

    Yesterday I called shemale I saw last year, met her through back page. She was home and I went over to spend some time with her. She is very passable. Filipino with a beautiful body and nice 6" ****. When I arrived she greeted me at the door and I enter her apartment. She was...
    stefanobk stefanobk
    31-35, M
    1 Response Jul 18, 2012

    I Want To **** A Shemale

    I dream of the day that I meet a tall pretty woman with legs and big boobs wearing a short dress or skirt. We are kissing and I start sucking her breast and my hands rome down under her skirt and to my surprise I fid the biggest d*** I ever seen. I start sucking it until I can't...
    blacklovelyone blacklovelyone
    51-55, F
    2 Responses Jun 1, 2011

    Wanna Try Shemale **** Soo Bad!!

    Wanna experiment my bisexual side with a shemale who has a nice **** and breats ;) I wanna taste sucking a ****, making it big on my mouth and taste it as it **** into my mouth.. Makes me horny and hard as i dream of it.. My *** craves for that **** now..
    Ladyboyy30 Ladyboyy30
    31-35, M
    Jun 6, 2012

    Phone Lust And Desire For Her... A Tgirl!

    Knowing you... knowing you know me so intimately... you know even my secret thrills, my anal play desires... hearing you play me, arouse me as I do you... caress, thrill, and wet each other... the sexy sounds of it all...new toys, new ways...oh baby take me! ....as I take you...
    Maxxx5772 Maxxx5772
    41-45, M
    Jun 8, 2012

    Shemales Are Hot

    I fantasise about shemales daily I love that you get the best of both worlds. I would love to get to know some sexy shemales. I want to know what it feels like to have a **** deep in my mouth
    eflo4811 eflo4811
    26-30, M
    Nov 17, 2012

    Hot Video

    Juat a little bit ago I watched a video of Ana Mancini a shemale. This video was an ******* series and wow was she hott. watching her made me want to suck her **** and lick her gorgeous ***, I have been sitting here since stroking my **** keeping it hard and making sure not to...
    deleted deleted
    26-30
    4 Responses Jul 28, 2012

    Just Thoughts

    I have always enjoyed this fantasy...simply being with and seduced by a preop transexual who precedes to rock my world. I am hoping to make my fantasy of having a transexual lover reality in the future. I think it would be a very interesting experience, and very erotic. I am...
    winterrosa winterrosa
    18-21, F
    3 Responses Jul 20, 2011

    Virginia Beach

    I'm a straight male looking for a relationship with a t-girl or otherwise serios tranny. Message me. :)
    todietotruth todietotruth
    26-30, M
    2 Responses Dec 21, 2011

    ****** By -t-girl In Front Of My Girlfriend

    I fantasize about being ****** by a hot t-girl with a bigger **** than mine while my girlfriend watches. Then the TG can **** her as well.
    litlebigman2 litlebigman2
    51-55, M
    1 Response Jun 17, 2012

    I Debated Not Joining This Group

    Partially because I don't think about it a whole lot, and I don't like to admit it.  But mostly because I know how to spell 'fantasize'!  Is it too late to edit the name of the group?
    SomeguyinUT SomeguyinUT
    31-35
    2 Responses Nov 4, 2008

    Unchartered Territory

    I am sure my story is not unique in the fact that I have never been with a shemale.  I fantasize all the time about their beautiful breast..long lean legs...and their hard special candy.  How I wish I could wrap my hands around the sweet flesh and totally enjoy that...
    jyd1 jyd1
    51-55, M
    4 Responses Jul 5, 2010

    Actually I Had Sex With Shemale

    and it was fun, all of them.
    jashdaren jashdaren
    31-35
    Apr 29, 2012
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