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I Crossdressing Transvestite

Personal Stories, Advice, and Support 929 People

    First Time Trying Women's Clothes

    I'm 30 years old and only recently since I moved in with my female friend when I'm alone I've tried her clothes on and it makes me feel so horny I'm shaking,trembling,I fantasise and watch gay tv ts ****,I've had sex with a ts girl in Amsterdam before n it was exactly how I...
    Kennytoyou Kennytoyou
    31-35, M
    Dec 8, 2012

    I Am Two Different People To One Person I Know.

    I often walk my dog within my apartment complex while dressed as a girl and, at other times in guy drab mode. There is an older woman who has taken a liking to my dog, a male pomeranian that she likes to call "Foxy" because, he does resemble a small red fox, even though he is...
    deenadahl deenadahl
    56-60, T
    5 Responses Sep 18, 2010

    You Lucky Girl,you !

    You Lucky Girl, You ! I think one of the most important things that I need to do here, and in general, is to talk to others like me, crossdressers, transvestites, sissies, etc. Alright, so you already know you are not alone. Far from it. But, you still feel guilt, shame...
    CherrySissy CherrySissy
    46-50, T
    2 Responses Apr 3, 2009


    I posted this to several groups. But it's really worth sharing. Just came back from a great shopping trip. I bought a couple shirts, a couple pairs of pants, and of course, some lingerie. If I can give one piece of advice, and maybe this is really dependent on where you live...
    BlushGreen BlushGreen
    26-30, M
    5 Responses Nov 24, 2011

    *** With Me

    Hi, I just love wearing leather skirts, nylon stockings, and garter belts together with my C-cup **** and stunning top. I often go out in the red light district, my high heels klicking as I walk by potential customers. I can't get enough of blow jobs, and love the taste of the...
    jeanette4u2 jeanette4u2
    46-50, F
    1 Response Nov 14, 2009

    How It All Started For Me

    So here goes..... 22/11/68 what a day that was.... not that I remember much about it. I was a home birth and to all intensive purposes a "normal" child and that's the way it would stay for a good few years to come. My mum Anne and dad Geoff no doubt were quite pleased that...
    Babyclaireuk Babyclaireuk
    46-50, M
    May 17, 2010

    Master Seeks Sissy

    I am a 28 year old, baby-faced, 5' 8", 70 kg City professional living and working in London. I am looking for a reasonably local sissy aged 18-23, smaller than me in every way, who wants to be completely feminised by me. Inexperience is a must - I want a shy submissive type who...
    masterguy78 masterguy78
    26-30, M
    Dec 15, 2012

    Lusty Tv

    Started wearing my mothers underwear when i was 9. I wanted to wear my little sisters stuff when i was five.
    Lustytv Lustytv
    46-50, M
    1 Response Jul 12, 2012

    Just Need To Talk

    I have been cross dressing for about 4/5 years now, I have a wife and children. my wife has helped me massively and she is the only one I can talk to, but as much as she tries it gets to her at times. I need to communicate with others like me because at the moment I feel things...
    jade80 jade80
    36-40, M
    1 Response Nov 17, 2013

    The Way It All Began For Me

    Sherman, set the way back machine to 1954, when it all began. I was four and, I found my grandmother's high heels (not very high by current standards) and her half girdle with garters (the metal kind, not today's cheep plastic ones) and her seemed stockings (still attached to the...
    deenadahl deenadahl
    56-60, T
    1 Response Oct 8, 2010

    How It All Started

    I was eight years old when I got the conpulsion for wear female clothing. My mother used to clean for a theatre company and I had to accompany whilst on the summer holidays, whilst there one I saw a victorian style dress,it felt natural and good, put it on and loved it, I was...
    wildcamper wildcamper
    51-55, T
    1 Response Jan 18, 2013

    The Truth About Me

    I have been a crossdresser for many years now, and I only let 1 friend know about it. She was a great friend who accepted me for me. When I was with her I was able to expess my feminine side without being ridiculed. Unfortunatly my friend, my best friend died in May, and I have...
    deleted deleted
    2 Responses Oct 10, 2010

    Secret Crossdresser

    I started to crossdress since my childhood.I started at age 10.Unfortunatley at that time in my country was a brutal war.My city was in a war zone.During the enemy attacks on innocent civilians among whom i lived with my family i felt an indescribable fear for my own life.I was...
    lardverder lardverder
    36-40, M
    Oct 3, 2013

    Married But Want To Try Being A Shemale

    Always dreamed about being a shemales boyfriend now at my young age of 50s I'd like to try being a tv sexy shaved legs body garter belt stocking wow make up than be someone's ***** totally submissive to his desires one day one night have my bottom speared deep as Iam tied up...
    mature9 mature9
    51-55, M
    1 Response Nov 24, 2012


    I just adore dressing in full undies stockings girdles basques etc but most of all heavy makeup if there is any one else how likes same please
    Sxyzue Sxyzue
    2 Responses Aug 14, 2012

    Mom Satisfied My Curiosity About Cross Dressing

    From an early age I loved to be dressed in girl's clothes and pretend I was a girl. The first time it happened, it was a babysitter who fixed me up in her little sister's clothes.  I was always sneaking into my mom's room and playing with her things. There came a time when I...
    Sissylips Sissylips
    9 Responses Dec 21, 2010

    Every Day

    My wife gave me a choice to have implants, and dress full time. I accept this offer knowing that I would never have to dress in those horrible clothes again. Soon I had a C cup chest nipples that were always hard, then after 2 years it went to DD and am told when it's been two...
    RunAroundSusan RunAroundSusan
    1 Response Jul 16, 2013

    Difficulty In Coming Out...

    I've been cross-dressing since I was 14. Me and a friend used to always steal his sister's clothes and "play" in them. Nothing sexual happened, but we were caught one day. Our parents were surprised, but they just accepted it as "experimentation." Nothing major happened, we...
    nightshade5511 nightshade5511
    6 Responses Dec 13, 2010


    Why is it went a guy wants to wear sexy lingerie he's labled as something?I love to dress in sexy lingerie and go shopping for more sexy thing to wear sometimes i go shopping fully dressed and nothing reall happens its the times when i'm dressed as a guy when clecks always say...
    maninagarterbelt maninagarterbelt
    41-45, M
    2 Responses Jul 31, 2009

    It Nearly Happened

    18 years ago when my wife was expecting our daughter I was sitting in our living room dressed in a sexy basque stockings and black thong watching tell with my wife when she told me she had a craving for some crisps so being in a hurry I pulled a shirt and trousers on and went to...
    Ttest Ttest
    46-50, M
    Jul 15, 2013

    Love To Crossdress In Women's Tight Latex...

    it started just by seeing pictures of women in latex and they turned me on. Then I thought - if it turns me on seeing someone dressed like that, i wonder what it will feel like if it is me. So i bought a feww things - latex leggings, panties, gloves, skirt, corset - and put them...
    deleted deleted
    1 Response Nov 20, 2011

    I Am A Crossdresser

    I am a bi crossdresser and have been crossdressing since my teens. I love the feel of soft silky fabrics against my bare skin and when I was younger the dressing was such a arousing experiance. I still dress and still get aroused but I dress now because it feels so natural and...
    krystals krystals
    46-50, T
    2 Responses Mar 25, 2010

    Love to Dress Up

    I am a straight male that loves the feel of ladies clothing. I love the feel of nylon on my body. I am not the best writer in the world, so please bear with me. It all started when I was around 10 years old when I would sneak into my moms bedroom and wear here gloves. That is...
    deleted deleted
    11 Responses May 30, 2008

    Wife Of Cross Dresser

    I have known of my husband's 'feminine' side before we married. We have experienced his cross dressing together. He really enjoys when I participate with him. However, for me, it is very awkward. It is strange to see my husband dressed as a woman with make up and wig and...
    wifeofcrossdresser wifeofcrossdresser
    5 Responses Sep 11, 2011

    Endless Longing

    I've spent all my life as a married heterosexual endlessly wanting to enjoy the pleasures of being feminine. Lately I've allowed myself to experiment with wearing female clothing when I'm alone and love the feelings of satin and silk on my skin. My wife with whom I attempted to...
    michelle56 michelle56
    61-65, M
    2 Responses May 29, 2011

    Crossdressing Couple

    When I met my wife she liked the idea of me dressing up in her clothes. I decided to surprise her and dressed up in some of her clothes one night before she came home from work. When she walked in the door, I had on one of her dresses, some pantyhose a bra with water filled...
    pantiescouple pantiescouple
    3 Responses Jul 19, 2010

    Wearing My First Bra

    Mom was was always at work.stole into her room.pulled out a blue lacey bra.boy did i tremble.took me ages to work it out. But did i thrust my chest out.where are my boobs ?
    jessicaslinky jessicaslinky
    46-50, M
    Mar 30, 2013

    Business Trip

    It started as a bet with a colleaugue at work when discussing an article on a drag act coming to town. My friend said no way aguy could get away with dressing up and passing in the street. I said yes they could and whats more I could. Fifty dollars to Cancer research...
    Carolaus Carolaus
    51-55, T
    1 Response Mar 29, 2009

    Why I Love To Crossdress

    Hi Please note that i have posted this in another group as well as this one!ps Its all True! I had the opportunity to get away for 4 days and decided Carrie needed a long weekend away. Kissing my wife good bye I set off on my journey. Making a quick phone call i prepared my...
    carriexd carriexd
    36-40, M
    Jun 16, 2010


      I am hoping that perhaps one of you older ones might be able to help me. I am a cross-dresser. I love Jimmy Choo, and I love my stockings. I started cross dressing when I was about 13. This would be about 1972. My first experience was with a pair of my (older) sister's...
    thejuggaboo thejuggaboo
    1 Response Aug 18, 2010

    Hotel Room Thief At Thirteen Looking Bra Panties And Underskirts

    On holiday with my parents. Hormones raging.socialising with couples downstairs.she early next to mine.go to bed early.i have that urge.i need my undies. Im confused. Open window drainpipe.climb up open next rooms windows.find panties in suitcase.there is no going...
    jessicaslinky jessicaslinky
    46-50, M
    Mar 30, 2013

    Matching Panties

    Playing next door with my friend.he gets called for his tea.i stay upstairs and silently creep into his parents room.trembling i find his moms drawers and steal a white bra short tennis skirt red baby doll nightie with matching panties.and then put my booty in the rippef lining...
    jessicaslinky jessicaslinky
    46-50, M
    Mar 30, 2013

    Beyond The Dressing

    I may have posted here before but, I don't know if I had shared this until now. I totally do enjoy crossdressing, and always have, and always will however, I reached a point where it was just not satisfying by itself. Wearing the clothing, from sexy to everyday jeans and tees or...
    deenadahl deenadahl
    56-60, T
    6 Responses Sep 6, 2010

    Becoming A Gurl...

    I remember when I was about 10, I became attracted to women's clothing. I didn't understand at the time, much less realize how this would impact the rest of my life. In a way it was horrible because I had no direction and no one to share this with. I could not ask questions and...
    ivanatgurl ivanatgurl
    46-50, M
    2 Responses Apr 8, 2011

    Early Experiences In Wearing Pretty Things

    I’ve worn my Mommie’s clothes since I was a little boy. I remember once when I was 5 walking hand in hand with Mommie to the grocery store when we ran into one of her dear friends. She was a lovely woman and she leaned down close to me at one point and “He’s so pretty. He...
    Candiegurl Candiegurl
    2 Responses Aug 8, 2010

    My Secret Life

    Since I was young I have worn lady's lingerie this all started when I used to see my mum walk around in her stockings and basques waiting for my dad to come home it looked nice so when I was home on my own one day I went in to there bedroom and tried it on and from that day I was...
    Ttest Ttest
    46-50, M
    2 Responses Oct 25, 2012

    I 2 a Crossdressing Transvestite

    When your born and raised in small rural towns in Sask. you have no idea of what was out there in terms of anything but homosexuals[BAD,BAD,BAD].It wasnt until years later that Ive seen what I considered to be what I always felt.It was a pictorial of a girl dressed with a penis...
    diadarling diadarling
    3 Responses Jul 15, 2008

    The Same?

    Until I got on to the internet and started researching my crossdressing I thought that a crossdresser and a transvestite were the same.From my research it seems that most feel that a crossdresser wears women's clothing for a way to relax and feel more comfortable. And a...
    happilymarriedguy happilymarriedguy
    51-55, M
    6 Responses Mar 17, 2013

    I was in my 50's before I got seriously into

    female dressing. To do that I want to a professional domatrix and using maid uniforms I had bought she trained me to be a real general maid. I am too old for that now and my wife needs me all the time so I don't do it very often but I really enjoy it when I do
    maidangela7349 maidangela7349
    70+, M
    Apr 19, 2016

    In the Moonlight

    I love to be dressed in high heels, stockings, suspender belt, sexy gstring, bra and lovely short dress, walking in the park, in the moonlight with the cool breeze blowing up my dress and so cool on my bare thighs and bottom...I imagine a lover meeting me and taking me, causing...
    yogamaster yogamaster
    36-40, T
    3 Responses Feb 6, 2008

    Cross Dressing Transvestite

    Oh My God, spelled the long way .I've just reviewed my shared experiences.OMG.How time has flown.Yes,by now I'm on hormones,and loving it. Finally starting to see real results ,physically and emotionally. My enviroment as also led to favored results. Ying/Yang, for now that I...
    diadarling diadarling
    1 Response Mar 24, 2011

    I Love It

    i love dressing like a woman. i've never been able to say that before. i live in arkansas and its not "acceptable" where i live. i love to put on a nice silky pair of panties and a bra and maybe some pantyhose then i get to decide if im gonna wear a dress or a blouse and a skirt...
    LacyJane LacyJane
    26-30, F
    2 Responses Dec 16, 2009
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