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I Fantasize While Im Crossdressing

Personal Stories, Advice, and Support 308 People

    I think we all do, but the other day I got to

    play it out. I showed my wife the slutty schoolgirl outfit I had put together and before you knew it she was the teacher that was going to fail me.Somehow I managed to pull my grade up to an A...Hoooray for oral exams
    babybearjean babybearjean 56-60, M 3 Responses Jun 16

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    Call me Mary when I wear girls underwear

    and my dress ;) I blow my belly up like a balloon while I'm wearing them so I look like I'm pregnant and growing But the toy I use gets boring I want a real person to inflate me and then do me ;) I'm bi so if ur a girl wanting to blow me up like a balloon message me Same u to...
    Brickwall96 Brickwall96 18-21, M 1 Response Jan 22

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    With A Bill Board

    saying honk if you want to **** me how many honks would i get? and how many *****?
    christinemelody christinemelody 56-60, T 3 Responses Sep 5, 2013

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    Pregnancy

    i fantasize that I am trying to get pregnant so i can give this man a little baby boy that looks just like him
    Barefootjamie Barefootjamie 18-21 2 Responses Sep 12, 2013

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    That I'm a slutty little cumm ****

    who would love to get gang banged or just straight up used as a cumm dumpster guys could line up and one by one they can all fill my holes with their thick loads shoot it all over my slutty face and once done I'm so dirty and don't care that I wouldn't even clean my face off or...
    nathaliajames4872 nathaliajames4872 31-35 4 Responses Dec 14, 2013

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    Related Experiences

    It is all I know in the last few years. I love crossdressing it is really so cool and great.
    bloubulsarel bloubulsarel 41-45, M 6 hrs ago

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    I think we've all been caught a lot more often than we realize. We just don't know about it because the other person never said anything. Anyway, something I saw earlier this...
    AlbertSAT AlbertSAT 66-70, M 7 Responses Nov 22

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    I know i haven't posted a picture of me in a while but tomorrow i will be able to crossdress for the whole night without anyone calling me or going into my room so i will post...
    Ruby1997 Ruby1997 18-21, T 1 Response 23 hrs ago

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    I do fantasize about being a woman. As far back as I can remember I have fantasized about being a girl. I wanted the long curly hair, the beauty of a girl, wearing girls clothes...
    Adam59 Adam59 56-60, M 4 Responses Dec 2

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    Forced to wear very high stiletto pumps! Probably my biggest of all my fantasies is having my girlfriend find out about my love of high heels (wearing them myself I mean) and...
    lockedheels lockedheels 31-35, M 2 Responses Nov 25

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    Ok so I really want to start posting more about my crossdressing as its important to me, ok so I only wear lingerie but its still something and I just cannot resist wearing it, it...
    Verix Verix 18-21, M 4 Responses Nov 24

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    New to ep been crossdressing since 13 now 56 love to crossdress wearing hose,skirts,sweaters,panties, heels, makeup,wigs,body shapers,and bras. Love sexy lingerie had sales ladies...
    lvrofhose lvrofhose 56-60, M Dec 2

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    Would anyone in the San Francisco Bay area be interested in meeting up sometime? I would love to have another crossdressing friend to go out with.
    Kylie2432 Kylie2432 16-17, T 1 Response Dec 4

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    I have this desire to crossdress, but don't have clothes. I used to have a lot, but I donated them all away one day to try and get myself to stop crossdressing. I love how women...
    cranblueberries cranblueberries 26-30, M Dec 9

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    Today one of my fantasies is starting to come true. I took my girlfriend out the other day and she had the sexiest dress on with these beige stiletto heels on, she turns me on in...
    Zoe24 Zoe24 22-25, M 4 days ago

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    Oh, I want you to walk in and grab me. I want you to spin me around, making me face you. I want you to kiss me soft at first, then get more passionate and rough. I want you to...
    SimbaLou SimbaLou 18-21, F 3 Responses Nov 26

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    I fantasize about being a girl for as long as I can remember. when I was a child I use try on my mother's close. I think a day ever went by I did think about being a girl
    okami2049 okami2049 26-30, T 5 Responses Dec 2

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    I fantasize about my best guy friend being the one pounding me really hard when it's actually my husband. It makes it so much more enjoyable for me and the thought is just...
    Neverbackaway Neverbackaway 16-17, F 1 Response Dec 5

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    I fantasize about my boss all the time. she is about 37 And I'm 32. she loves to wear sexy skirts with pantyhose and heels. she also has a nice perky, fake rack. she's like someone...
    ladylover1980 ladylover1980 31-35, M Dec 8

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    I'm 18 and have never been pregnant but I think about man holding down and impregnating me while I touch myself.
    lzgroupie96 lzgroupie96 18-21, F 10 Responses 6 days ago

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    I like to fantasize about me and my boyfriend having sex when we r married and giving him a ******* and tasting his *****
    sims3freak sims3freak 22-25, F 1 Response 3 days ago

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    Air conditioning has become an inseparable item on household luxuries these days. Most houses have air cooling facilities to help their inmates beat the summer heat. However, one...
    addhavc addhavc 18-21, F Dec 1

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    So I know I just joined and Im loving talking to everybody but I have to leave for a while but I promise I will be back in a few days! Please don't forget about me :)
    morganhale morganhale 18-21, F 5 Responses Nov 20

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    The major changes in gameplay are related to the movement, but are more visual than tactile. The control is still consistent, but now the screen movements reflect the intentions of...
    game3personal game3personal 22-25, M Nov 21

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    I do. Im a slow typer and have lots of things going on. Doesnt mean im not interested in talking, just means that It takes a lil while for me to: 1) think of what to say 2) grab...
    chocolatecurlz chocolatecurlz 18-21, F 1 Response Nov 22

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    I'm stuck at a bar. For hours.... While people see a show I couldn't get into. :/ trying not to be a complete drunkard.
    tarkovsky tarkovsky 26-30, M Nov 28

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    I want to learn how to handle my emotions while under attack. It is critical to be able to be my best self, or at least an acceptable version of myself, when I am under attack...
    tryingagainII tryingagainII 56-60, M Dec 3

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    I went to a doctor for help with insomnia. "How much caffeine do you drink?" Well I have a shot of espresso or two....while the coffee is brewing. "That's a little excessive." Well...
    justmeandmydreams justmeandmydreams 26-30, F 2 Responses Dec 6

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    ...
    plentyof plentyof 18-21, M Dec 9

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    I had a friend in high school, I knew she has a crush on me. She watched me change a little to closely, her eyes would linger her hugs lasted a little to long. Whenever she spent...
    LSix LSix 36-40, F 1 Response 1 day ago

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    I was jacking off in my jeep one afternoon down an old gravel road & I had been jacking for a while & got to noticing that there were men up in there deer stands about 6 of them...
    timtooltime timtooltime 46-50, M 1 Response 1 day ago

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    For the right girl! I love being feminine and sensually appreciating the same in another can be a real turn on!
    BisexElle BisexElle 26-30, T 4 hrs ago

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    Mmmm I do that ;) anal is good too
    Sextme6996 Sextme6996 41-45, F 3 Responses Nov 27

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    I'm far north side Houston Texas, and would like to meet TG or CD. Like to hear from you!
    PaulBeach4 PaulBeach4 56-60, M 1 Response Nov 20

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    I am new to all this but would like new friends some heple 2 would be nice
    pitsfield pitsfield 41-45, T 2 Responses Nov 20

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    i am a virgin from behind but would like that to change can anyone help me
    tyrabelmont tyrabelmont 51-55, T 1 Response Nov 20

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    New dress I look hawt as a teenage girl I wish I was one honestly I love the clothing
    Zlayer99 Zlayer99 26-30, M 3 Responses Nov 22

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    🎢And it looks like I'm the queen 🎢 πŸ˜˜πŸ‘— I always wanted to be Elsa I think I'll beg my mommy to be Elsa for halloween I'm so girly when I cross dress I want to do it 24/7...
    Zlayer99 Zlayer99 26-30, M 3 Responses Nov 22

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    I'm a gifted angel I look hawt in dresses and skirts not many boys do
    Zlayer99 Zlayer99 26-30, M 2 Responses Nov 22

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    i think on some level i used to set myself up to get caught. the first couple of times were truly candid without much thought going into it. after learning the extremes of...
    trailsonrails trailsonrails 51-55, M 2 Responses Nov 23

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    Anyone in uk kent to cross dress pleease with
    neopchef neopchef 26-30, M 1 Response Nov 23

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    In bed no sum thing on Lovit
    secretlife88 secretlife88 26-30, M Nov 23

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    Looking for other cross dressers. I want to learn from you and talk about everything related to being a cross dresser.
    SamanthaCD5 SamanthaCD5 22-25, T 1 Response Nov 24

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    some one in Georgetown.Ky want chat and play?
    pantiestrucker pantiestrucker 46-50, M 4 Responses Nov 24

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    I don't see a problem with cross dressing. I am a male and I wear dresses and skirts. I also wear other women's clothing. If your happy with what you wear then your more relaxed...
    Adam59 Adam59 56-60, M 4 Responses Nov 25

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    any cds wanna chat!? :P xoxo
    Crossdressheels Crossdressheels 18-21 2 Responses Nov 26