Post

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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    Related Experiences

    Cuffed and in custody during the holiday season. I wasn't really caught in the act of crossdressing but I was caught with the clothes for crossdressing. I actually had told this...
    banannasplitz09 banannasplitz09 22-25, M 1 Response 17 hrs ago

    Your Response

    Cancel
    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 Jul 19

    Your Response

    Cancel
    Hi my name is ben I, live in swansea in wales, and im 17. I have long had fantasies about crossdressing, I would love to meet people on here to explore this aspect of my...
    swansea21 swansea21 18-21, M 3 days ago

    Your Response

    Cancel
    My craze for dance and body building started from Salman Khan and still counts on...This was the first song in which my dancer came out of me and still singing the same out of me...
    adiscorpion41 adiscorpion41 22-25, M 6 hrs ago

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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 Jul 22

    Your Response

    Cancel
    I have been crossdressing for a while now but the first time I was caught was when i was 10. I have a older sister that washed cloths with mine one morning, and she had her pink...
    Fogle3 Fogle3 18-21 1 Response 1 day ago

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    It started off as just wearing my wife's tights. Now I don't know where I am?! I've wore stockings, suspenders & even bought my own heels & it feels so sexy! I've always thought I...
    susspender susspender 41-45, M 4 Responses 5 days ago

    Your Response

    Cancel
    It started when I was around 12 I had a friend that was a girl and we were playin truth or dare and she dared me to wear one of my sisters thongs for a few days and I did I love...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 1 Response 1 day ago

    Your Response

    Cancel
    I think it all started with moms pantyhose. Had them stashed in my room. I'm sure she knew. Nothing was ever said. To this day I wear them whenever I can.
    dazzlinglegs dazzlinglegs 36-40, M 23 hrs ago

    Your Response

    Cancel
    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

    Your Response

    Cancel
    My sister has started self harming again. She was clean for awhile but she started a week ago again.
    blahlahblah599 blahlahblah599 16-17, F a week ago

    Your Response

    Cancel
    In my fifties and possibly a bit late to the game. I had a pack lying around from my work and decided to give it a try. To give you some background to my story, I have always been...
    parry03 parry03 51-55, M 2 Responses 4 days ago

    Your Response

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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    Started at 12 and now I'm 14
    RacerXX2 RacerXX2 13-15, M 1 Response Jul 9

    Your Response

    Cancel
    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 2 Responses Jul 15

    Your Response

    Cancel
    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 2 Responses Jul 19

    Your Response

    Cancel
    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 Jul 21

    Your Response

    Cancel
    Just started Jillian Michael's 30 Day shread.
    fpdee11 fpdee11 26-30, F Jul 21

    Your Response

    Cancel
    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 2 Responses Jul 22

    Your Response

    Cancel
    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 Response Jul 22

    Your Response

    Cancel
    I was probably 12-13 when I started, but I was about 15-16 before I had my first ******.
    emileenicole31 emileenicole31 18-21, F 3 Responses 4 days ago

    Your Response

    Cancel
    There just comes a point in life when you're completely done, it just so happens that that point is now. I'm eighteen and I feel like I have nothing to live for. I had a...
    LeslieMarie247 LeslieMarie247 18-21, F 4 Responses 2 days ago

    Your Response

    Cancel
    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

    Your Response

    Cancel
    Loving my new floral tights.
    susspender susspender 41-45, M 12 Responses Jul 4

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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 4 Responses Jul 9

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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

    Your Response

    Cancel
    The best makeovers I get from a friend who works in a department store turns me into a sexy woman i always want to be . Pink is my favorite color ,shocking pink short mini .pale...
    LexiMX81 LexiMX81 36-40, T 10 Responses Jul 16

    Your Response

    Cancel