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I Started Crossdressing

Personal Stories, Advice, and Support 118 People

    Last night i confessed to my mom

    that i want to try crossdressing and painting my nails and this morning she bought $100 dollars worth of womens cloths online. Im so glad I confessed to my mom, im going to own my first pair of heels and dress in a week :D Thank you people who replied to my last post.
    Poopoohead17 Poopoohead17 18-21, M 1 Response May 17

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    Started?

    Not 100% sure what got me started crossdressing and when it was.I remember as a kid I would look through the Christmas catalogs that would be laying around just before Christmas. When people were around I would be looking through the toy section, and if no one was around I would...
    happilymarriedguy happilymarriedguy 51-55, M Nov 25, 2012

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    Related Experiences

    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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    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 4 days ago

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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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    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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    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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    I have been crossdressing since I was in my teens .over the years the compulsion to dress as a woman has intensified dramatically .i now dress completely with full make up and am...
    francescalewis1956 francescalewis1956 56-60, M 1 Response 1 day ago

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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 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'm on day 3. I'm improving a little bit. I'm really happy I decided to do this. I know I can keep it up because I've already started and I have motivation. I like the way I'm...
    fairytalesandspiderwebs fairytalesandspiderwebs 18-21, F 1 Response Jul 3

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    An Update. On February 1, 2014; I finally started my HRT. Within 3 weeks I was seeing changes.
    lizagirl69 lizagirl69 41-45, F 3 Responses Jun 26

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    I started smoking and love it. How can I become a heavy dependent smoker
    lancebuddyfranklin lancebuddyfranklin 22-25, M 2 Responses Jul 1

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    I got my gym membership yesterday and I also began working out yesterday. I've always been on the smaller side. At the most I've weighed 140 but right now I'm 125. Even though I'm...
    fairytalesandspiderwebs fairytalesandspiderwebs 18-21, F Jul 3

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    I started working out since,I don't remember, but I ain't stop my routine of an exercise...
    wt00r wt00r 26-30, M Jul 6

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    I just recently started a new job at Taco Bell and I'm a cashier. This is my first job and I continue training tomorrow. I'm nervous because I messed up a few peoples orders. What...
    xxlibradollxx xxlibradollxx 16-17, F 3 Responses Jul 6

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    Started at 12 and now I'm 14
    RacerXX2 RacerXX2 13-15, M Jul 9

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    I just started smoking cigarettes. They calm me down but I feel so guilty smoking them. I know they are unattractive and disgusting to most people. I only smoke in private.
    GabbyCot GabbyCot 18-21, F 1 Response Jul 15

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    I just started writing my first erotica and I just sent the third chapter to my beta readers, which contains the first sex scene. This should be rather interesting ;)
    explicitwriter explicitwriter 22-25, F 4 days ago

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    I started today on the treadmill. I've read that jogging is good for burning fat and speeding up one's metabolism. This is exactly what I want. I know I'm terribly out of shape. I...
    fairytalesandspiderwebs fairytalesandspiderwebs 18-21, F 1 Response 2 days ago

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    Just started Jillian Michael's 30 Day shread.
    fpdee11 fpdee11 26-30, F 2 days ago

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    I started with my friend when I was 6-7 and ate her and then when I was 7-8 my step brother at that time took me every weekend he had a really big one and he was 17 after that I...
    dirtyperv35 dirtyperv35 31-35, M 1 Response 1 day ago

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    Right, although no one has said anything, I've started to think that my EP speak could be getting annoying. They are pretty obvious, but I'll explain a few of my speech features...
    InternationalDarkness InternationalDarkness 13-15, F 1 day ago

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    Hi i am a female still in middle school and i want to crossdress.But how can i hide it? i mean from my elders and maybe classmates...but anyways it would not be hard for me to fit...
    crosdreser123 crosdreser123 18-21, F 14 hrs ago

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    jmallon764 jmallon764 18-21, M 11 hrs ago

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    jmallon764 jmallon764 18-21, M 1 Response 11 hrs ago

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    jmallon764 jmallon764 18-21, M 1 Response 7 hrs ago

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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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    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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    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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    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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    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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    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...
    conankoller conankoller 22-25, M 4 Responses Jul 13

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    So tired of so called trading pics I step up and send the first one and don't get **** back it's getting old I just want to play no harm done
    ddavis21 ddavis21 18-21, M 1 Response Jul 14

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    Looking for lady friend who will accept and support me as a cross dresser and guys who are into dresses, heels and pantyhose
    annieinhose annieinhose 46-50, T 2 Responses Jul 15

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