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I Fantasize While Im Crossdressing

Personal Stories, Advice, and Support 275 People

    That I am a hot Lesbian MILF

    who is seduced by the babysitter or my neighbor's daughter.
    Laviana Laviana 46-50, T 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 2 Responses Jan 22

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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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    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 2 Responses Jun 16

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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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    After stumbling across a cross-dresser in p**n,

    all I think about when I'm in public out of my feminine personality is that I wish I was wearing more than just my sisters tight underwear. I'm new to this site and love all the like-minded people, post an experience if u feel the same way.
    Jess967 Jess967 18-21, M 4 Responses Apr 7

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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 26-30 2 Responses Dec 14, 2013

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    Related Experiences

    Sometimes people think that crossdressing automatically would make someone seem gay, but that isn't it! Crossdressing is just a thing that some men (or women) like to do! It makes...
    naco26withcheese naco26withcheese 13-15, M 1 Response 2 days ago

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    The first time i was caught crossdressing i wad 16 and wearing high heals, fish net stockings, a short skirt, a small skimpy shirt and makeup on. The worst part is my mom caught me...
    bottomslut1 bottomslut1 18-21, M 2 Responses Jul 6

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    I fantasize about my wife being taken in front of me. Her watching me while being used by another man or women.
    Teschm18 Teschm18 31-35, M 4 Responses Jun 23

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    I fantasize about me being raped and I'm only 13 Help Yesterday I had a dream about my dream adoptive father (in my dreams I'm adopted by rich people) I dreamed about my adoptive...
    LittleLuna22 LittleLuna22 13-15 4 Responses 6 days ago

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    I fantasize about me being raped and I'm only 13 Help Yesterday I had a dream about my dream adoptive father (in my dreams I'm adopted by rich people) I dreamed about my adoptive...
    LittleLuna171 LittleLuna171 13-15, F 10 Responses 2 days ago

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    I started crossdressing when I was around ten years old. Womens clothes just feel right on me. I liked crossdressing since the first time I wore my sisters bathing suit. It was...
    Jessica1967 Jessica1967 41-45, T 6 Responses Jun 26

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    I was bisexual as a young man but what I learned I found to be my biggest turn on happend while with a bi friend. I went into my bedroom a looked into my bathroom and I was shocked...
    LexiMX81 LexiMX81 36-40, T 5 Responses 5 days ago

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    Why are females who accept a guys feminine side so hard to find? Looking to chat to females or males who accept crossdressing 💋
    susspender susspender 41-45, M 4 Responses Jul 12

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    Looking for some one to share story's about getting caught wearing girls panties or crossdressing
    ddavis21 ddavis21 18-21, M 1 Response Jul 13

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    When my lesbian bi sister is horny she uses a stapon on me while i wear girls clothes and a wig
    bottomslut1 bottomslut1 18-21, M 2 Responses Jul 6

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    My job was to vacuum so, as usual, when I got to my moms closet (which is pretty big) I put on one of her dresses while I vacuumed. Today was a rainy day so everyone was inside...
    kylexdress kylexdress 13-15, M 2 Responses Jul 7

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    I now have 6 dresses and 10 pairs of high heels, with more dresses coming I am sure. I just love the idea of wearing only dresses and high heels every day while I am with my...
    Plugslave Plugslave 31-35 4 Responses Jul 12

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    It was a while ago. I work evening and love driving in a dress and bra and matching panties. I just got home and most of the time my Wife is in bed sleeping so I thought the coast...
    wayne60 wayne60 51-55, M 1 Response 10 hrs ago

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    Hey any girl who fantasizes about being raped or having sex with an unknown guy message me! ( near or in Austria) ;)
    swag8 swag8 18-21, M 2 Responses Jul 10

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    i know people think im to young and stuff.. but seriously think about it how many teens have lost there virginity in your life time . its not like im planning to lose it or im...
    crazyvibe crazyvibe 13-15, F 6 days ago

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    I like for my room to be fairly cold while under big comforters and just playing around while cuddling. Best sleep ever!
    hgprice hgprice 26-30, F 4 Responses Jul 9

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    Sometimes words hurt. Sometimes they make people want to kill themselves. It hurts them so much that they would rather take their own life. I grabbed a knife and held it up to my...
    callmedemonchild callmedemonchild 13-15, F 3 Responses Jun 22

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    While you were sleeping..I ate all of your dark chocolate fudge cake ala mode....glad you had my favorite Haagen-Dazs Swiss Vanilla Almond Ice Cream on hand. Thanks...**BURP...
    Davido57 Davido57 56-60, M 1 Response Jun 22

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    Being very constipated as i am always, I don't really have any other option but to strain heavily in order to go. But straining and grunting while pooping is very common and...
    gio36 gio36 36-40, M 1 Response Jun 28

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    I also make music while I'm working. I improvise. I use al my resources at my disposal and make instruments out of them. Work doesn't always have to be dismal. You can have a live...
    AquariusLife AquariusLife 26-30, F Jun 30

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    Broke down and cried yesterday while my boyfriend was at my house. He is talking about deployment and I have no idea what to expect. This would be his first deployment. It's not...
    ngutman22 ngutman22 18-21, F Jun 30

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    There will be 3 playable faction alliances within the Elder Scrolls Online: The Aldmeri Dominion, the Daggerfall Covenant and also the Ebonheart accord. selecting one in every of...
    mmogoogle mmogoogle 22-25, M Jul 1

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    I love the feel of nylons on my skin, especially when I wear a thong or bikini panties. . one day while driving I was wearing pantyhose a a short skirt and felt soo horny. I...
    siskrista1 siskrista1 31-35, T 1 Response Jul 11

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    I finally told my sister about my cross dressing and she let me wear her things :-)
    Zlayer99 Zlayer99 26-30, M 8 Responses Jun 22

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    So I use to wrestle so I cut out an out fit from my old wrestling uniform how does it look ?
    Zlayer99 Zlayer99 26-30, M 1 Response Jun 23

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    I would love to hear from closet crossdressers
    jasmine176 jasmine176 56-60, M Jun 26

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    My greatest desire is to have a stable relationship with another gay crossdresser like me and so I'm still looking. I am in Miami FL.
    fercrox fercrox 46-50, M 2 Responses Jun 27

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    Can't sleep anyone fancy a chat ? :) x
    xdresses xdresses 18-21, M 4 Responses Jun 28

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    Would like to find a girlfriend that understands... Live in northeast PA
    capricorn79 capricorn79 31-35, T 1 Response Jun 29

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    So I may not be supportive right now but I really want to be! I've been going out with my boyfriend for about a little more than two weeks. Today he told me that he actually cross...
    IAmWhoIAmWhoAmI IAmWhoIAmWhoAmI 18-21, F 1 Response Jun 30

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    I tried out for my first time ever a dress, heels, and wig! I had no idea heels are so addicting, I only want more lol. Never had I thought dressing up all girly other than...
    VeryImportantPerson VeryImportantPerson 26-30, M 1 Response Jul 2

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    Loving my new floral tights.
    susspender susspender 41-45, M 11 Responses Jul 4

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    I started at 7 years old . I am now 53 and have now become obsessed with dressing even in front if my partner
    dab2230 dab2230 46-50, M 3 Responses Jul 8

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    I was caught by my Mom it was when I was about 8 we were having some friends over for a party. I snuck off and found my Mom's high heels and put them on and was admiring myself in...
    pmgurl pmgurl 51-55 3 Responses Jul 9

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    When I was about 16 I found my Mom's red lipstick and decided to put it on, thought I would only leave it on for a few min. I had it on and was doing some things in my room when a...
    pmgurl pmgurl 51-55 Jul 9

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    Mistress has been making me shorter and shorter dresses, and having me tan my legs too. She likes to set out my dress, heels, and hosiery every night for me to slip into the next...
    Plugslave Plugslave 31-35 3 Responses Jul 9

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    ok, so im straight and went to a gay bar in madison hoping to meet some crossdressers but nobody was there. Well no crossdressers. I was so looking forward to some good advise...
    josephine39dd josephine39dd 26-30, T 2 Responses Jul 12

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    When I was 12 i realised a loved the feel of female clothing being a guy myself it was strange I knew my mum would freak if she found my out so in the end i decided to make my own...
    Crossdresserman Crossdresserman 22-25, M 4 Responses Jul 13

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    I went out being the guy i am i was wearing my sexy black dress and heels when i was in a shop i saw my friend who noticed me i ran like hell and he followed i hid but he told my...
    conankoller conankoller 22-25, M 3 Responses Jul 13

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    I missed the mailman and needed a letter mailed. So I hopped into my car and drove to the post office. I was wearing a black bra with a oversized tank top and black shorts. It...
    meg1cdforyou meg1cdforyou 61-65, M 2 Responses Jul 13

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    Today my mum was at work and my brother and sister were asleep (for the whole day) so i decided to go through my mums cloths and i found the most beautiful see through silk dress...