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I Enjoy Crossdressing

Personal Stories, Advice, and Support 1,140 People

    I love wearing high heel leather boots,

    shoes, long leather gloves, corsets and leggings!
    LondonGuy1 LondonGuy1
    31-35, M
    1 Response Dec 3, 2013

    Im starting crossdressing any old dress skirt

    wigs shoes will b a big help i can pay for post if u wish
    crossdresskatie crossdresskatie
    26-30, M
    Dec 8, 2013

    I'm going to be posting

    and sending nude pics or will be on Skype so add me kik: missjazzmin Skype: misscrossdresser
    missjazzmin missjazzmin
    1 Response Aug 11, 2014

    Why I Enjoy Dressing In Lingerie

    I want to do it because I enjoy it so much. I can’t express the feelings and sensations I get while dressed in words. Dressing in silky lingerie just seems natural for me and it fullfills a large part of my sexual desires. I also find it sexually stimulating because I...
    jamiesissycd jamiesissycd
    61-65, M
    1 Response Dec 20, 2011

    My Story

    I started fully cross dressing at the age of 23 after wearing pantyhose off & on since the age of about 14/15 but at first I could only do it in the confines of my bedroom as I lived with my father or when I had a week day off from my job Then one friday night  my father told...
    xdpaul xdpaul
    56-60, M
    Jun 8, 2011

    Where To Begin...

    I am not sure when I first became aware of my desire to wear feminine clothing...but I know now that the beginning is not the focus...It is where do I want to end up. I simply love the feel of nylons and garters...thong panties and the smooth silk feeling that shaving my legs...
    jyd1 jyd1
    51-55, M
    2 Responses Aug 19, 2010

    The I Wear Panties Hat

    I once hatched the idea of having a custom hat made at an embroidery shop "Embroider_me". My thought was to work on the design with a lady from the shop. Well luckily the lady that owned the store was more then happy to help. I told her I wanted: "I Wear Panties" on the front...
    mattr4u2 mattr4u2
    61-65, M
    Jul 28, 2013

    Just went Walmart at my lunch break

    and bought thigh highs and panties. Both black. the panties are lacy and feel so good. Now I'm at work with them under my work pants lol.
    denCD denCD
    41-45, M
    3 Responses Oct 28, 2015

    I Enjoy Crossdressing

    i started crossdressing back in 1998 it started when i accidently bought a womans tank top from a thrift store i wasn't sure at first why it felt the way it did, i just knew there was something different about the way it felt, until i relized it was a womans tank top by then i...
    kaitlinrenee24 kaitlinrenee24
    41-45, T
    8 Responses Jul 28, 2012

    i finally got the chance to spend an entire day

    dressed. it was so much fun! but now i want to do it again and i have no time to! i wish i lived alone
    quirkysquirt9 quirkysquirt9
    22-25, M
    2 Responses Jul 30, 2015

    Neighbor Caught Me Crossdressing! Had Foursome With Her And Her Husband!

    had a little mishap, that may turn into something fun. :)so, when at home, i am 95% of the time dressed up. usually, its nothing more than a little negligee, panties, stockings... or a silk robe and some pantyhose... just basic around the house stuff (but always with nylons of...
    jenrip jenrip
    26-30, T
    4 Responses Apr 4, 2013

    I Love Crossdressing

    Crossdressing is everything to me! Because I feel I was supposed to be born a girl and not a guy so I wear girls clothes, right now I'm wearing a khaki colored skirt with a black shirt and nude shade pantyhose :)
    PantyQueen95 PantyQueen95
    22-25, T
    1 Response Nov 16, 2013


    Francine what can i say ok WOW you are a sweety hugs  Nadia
    deleted deleted
    1 Response Jun 20, 2008

    I Enjoy Crossdressing

    I so enjoy cross dressing. I enjoy it  so much that i look forward to everyday.  I like to decide what to wear each day and then decide what I can change into on some days I have meetings or other obligations .  It's fun to go shopping to  find a new outfit to wear or...
    jml2000 jml2000
    61-65, M
    Oct 29, 2012

    First Time I Wore Womans Clothes

    I have been fascinated with feminine clothing from my earliest memory. They were so mysteriously constructed. Their but the buttons were on the left, zippers were in the back and on the side, they had buckles but not just on belts but on shoes. And as if this were not enough and...
    deleted deleted
    2 Responses Jan 15, 2013

    Finding Myself....

    when I was alot younger, like in early middle school years I started changing inside. Like most boys I was hitting puberty, curiosity and all that jazz. Now I was and have always been attracted to women. Just as much as any horny teenage boy I was extremely shy to talk to girls...
    LuCyFuRs LuCyFuRs
    31-35, M
    Oct 14, 2013

    i had a wonderful weekend.

    It started friday. got to paint my fingernails.(toes always done) and off my mistress and I went. I was able to go through her closet and pick out three dress (will be post pic) full make up. I haven't dressed up in full make-up nails hose and dresses in 8 yrs now, with a clean...
    jamie123T jamie123T
    46-50, M
    1 Response Jan 13, 2014
    24chris24 24chris24
    26-30, T
    Apr 26, 2014

    My Wife Finally Knows

    I've been crossdressing since I was about 10 years old. At the time I loved to put on some of my mother's stockings and sometimes my younger sister's panties. But it never went much beyond that and when I left home womens' clothing became a scare thing in my house and it all...
    BettyLouAnne BettyLouAnne
    1 Response Oct 31, 2012

    And Now I'm A Mature Cd Servant , And I Have Never Been Happier!

    i grew up in the south with a military dad, and a mom who worked for the govt. i can remember touching my moms legs in hose when i was very little and loving the feeling. when i hit puberty it seemed so natural to me to try on her clothes,particilarly her undies and hose. i was...
    zanderb zanderb
    41-45, T
    2 Responses May 28, 2012

    Shopping Cross Dressed!

    What a great experience! I have been playing around with dressing for a while, but I've only gone out in public once before- and I was not confident then at all. This time was different, but ended far too quickly. I brought all my girl things with me today and left them in the...
    stevekone stevekone
    2 Responses May 6, 2013

    Total Fail

    So today I thought I was being really cute and sweet not to mention sexy when I went shopping for my boyfriend. I found these really cute thigh high red stiletto pumps for an amazingly awesome price .... Bought them and sent him a pic of the web pic.... Not uncommon since we have...
    Ladysound Ladysound
    22-25, F
    2 Responses Jan 2, 2013

    The Experience

    I have been cross dressing for over 40 years now. That is to say , I have been wearing what is usually designated women's clothing for that time. I started with my mothers dresses and underwear when I was a teenager, and progressed through to my first wife's clothes , and her...
    miranda69 miranda69
    May 24, 2013

    I especially like wearing second hand lingerie,

    dresses, ect... The outfit that I am wearing now, (Black blouse, gray skirt, underwire bra, and pantyhose), I just got today at a garage sale. The full nylon slip and pumps are also second hand
    OhioSissy OhioSissy
    56-60, M
    5 Responses May 22, 2014

    Love Crossdressing

    nothing better dressing up in 6inch heels thigh high silk stockings miniskirt, with a thong **** tucked away looking for ****. they bend me over while in heels lift skirt get banged love it. but can or is there anyone could teach me better or men that want to use me as there...
    goforit514 goforit514
    46-50, M
    1 Response Jun 25, 2012

    hello, my last story was over a yr ago.

    Now i'm living in charlotte with my girlfriend/mistress. She is all about dressing and exploring everything. We even have talked about go to adult bookstores and swinging. I have accepted that i love all sex. I love being used by all. i beg for to leave whip marks and make me...
    jamie123T jamie123T
    46-50, M
    2 Responses Jan 3, 2014

    I Find Panties, Pantyhose, And Stockings Orgasmic

    i first started wearing panties at 13, and i havent stopped. just the sight of a hard **** in panties or hose is enough to make me ***.the feeling of that soft nylon or satin against my **** is exquisite.
    jenrip jenrip
    26-30, T
    2 Responses Apr 4, 2013

    We Enjoy Crossdressing

    I've been into crossdressing since I was younger. I love wearing stockings and suspenders and satin panties. I've been bi since I was young, but I love dressing and having sex with others like me. My wife surprised me by saying she would love to see me in lingerie because of my...
    pantiescouple pantiescouple
    1 Response Jul 19, 2010

    Buying Lingere As A Man

    I actually went to a local sex shop yesterday and bought two pair of sexy stockings. Also had mentioned to the girl behind the counter that I am into crossdressing. She was cool and showed me their wig selection.
    swallowbig swallowbig
    36-40, T
    1 Response Mar 10, 2013

    The Beginning And Scared

    Hello i am a 20 year old guy and I love to Crossdress. It started when my mom past away and I was 9 years old that was when I started I was home alone and bored I quess. So walked to my parents room and tryed her clothes on and it felt great. Sinds than I now I was a Crossdresser...
    crossdressboy10 crossdressboy10
    22-25, T
    Mar 19, 2013

    Letting That Femme Side Out!

    Crossdressing is such a wonderful way to let out your emotions in a positive and healthy way. I live in a society where men are taught to be macho, which is okay, some of the time. I think being tied to one trait such as macho-ism, is really unhealthy. I enjoy sports, but...
    Camifemme Camifemme
    31-35, T
    4 Responses Jul 22, 2012

    so im 23 I've been crossdressing

    for a few years now started with my mums stuff now got my own little collection and always looking to expand my collection. although living in a house with 5 other guys it is a bit tough. Ive never told anyone that i do it. however i have been dressed up for fancy dress. Id love...
    cdbecki cdbecki
    26-30, M
    Jan 26, 2015

    She Let Her Friends **** Me

    While I was in her lingerie she brought her friends in the room, and one by one they used their strap ons on my little sissy *** as I could only lay there and take it, mortified I had just been outed as a **** craving sissy
    curiouslycurious17 curiouslycurious17
    26-30, M
    2 Responses Oct 24, 2013

    Crossdressing With Husband

    sanjeetaklk sanjeetaklk
    26-30, F
    1 Response Sep 27, 2012

    CD And Sex Drive

    I am a closet CD. Over the last year, my CDing has been increasing in intensity. I started off underdressing, trying my best to hide every trace of CDing. Now, I'm wearing women's jeans and push up bras. Still closeted but definitely showing enough that a curious person can tell...
    ClosetTrans ClosetTrans
    31-35, T
    Oct 2, 2013

    Creature Comforts

    I just enjoy being in anything that a woman wears. The clothing is nice and soft and fits nicely. I have never shared my secret with anyone in my physical life. I am sure some of my girlfriends now because I would try on their things when I had the erge. I like getting all...
    deleted deleted
    Aug 24, 2013

    My Dream Outfit

    my dream outfit would be a nice pink bra and a matching thong, id then have some black high heels on with some knee high socks! then over my beautiful thong id wear a short denim skirt with a gorgeous white blouse(so you could see my pink bra)! then i would love to go to town...
    stranger123456 stranger123456
    3 Responses Aug 11, 2013

    Of Course

    I just love to wear my lingerie. I wear panties 24/7 (except for Dr. appointments). On weekends I will sometimes wear my thigh high stockings under my jeans.I don't know what is about wearing silky lingerie but it just relaxes me so much and makes a lot of my stress disappear. I...
    happilymarriedguy happilymarriedguy
    51-55, M
    1 Response Apr 4, 2013

    I Feel Much Better When I Have Lingerie To Wear.

    Throughout my high school days I dressed whenever I got the chance, in a house of 10 people and 1 bathroom not much. But i did find myself alone with bras drying on the shower rod every now and then. So a bra, the Sunday lingerie ads and a free hand...ecstasy without agony...
    deleted deleted
    1 Response Mar 28, 2013

    How It Started

    i enjoy crossdressing as it makes me feel sexy all over.. as i have a strong love for lingerie.. and then it started when i was younger and would go over to friends houses and see their sisters panties or bras in the hamper i would take them home and dress up and jerk off.. and...
    CathyCD CathyCD
    2 Responses Jun 28, 2008


    Crossdressing i have crossdressed off and on since 1998 it all started when i got rid of some clothes after a garage sale for my mom also that same summer i bought a womans tank top by accident at first i knew there was something different about the way if felt but then i liked...
    deleted deleted
    Jul 22, 2013

    Dressing For A Wedding

    So this past weekend we had to attend a wedding, I jumped in the shower and shaved what I am allowed to share. ( I feel like a child, shave what I'm allowed too!!!!!) Anyway after I was finished I go into the bedroom, on go the bright red panties, nice and romantic. White dress...
    mpenner mpenner
    1 Response Sep 9, 2012

    The Advantages Of Having A Crossdressing Boyfriend Or Husband!

    YOU have a live in cosmetologist. If he wears a skirt it's easy access. He always envies you because he would rather be wearing what you are wearing. You can have a girlfriend as well as a boyfriend who doesn't mind waiting while you take your time shopping. You can double your...
    jamiesissycd jamiesissycd
    61-65, M
    1 Response Feb 27, 2012

    Often Misunderstood...

    EP has given me the opportnity the last few months to find out more about myself. In particular why I am how I am, why I like what I like, and if I am truly happy. There are many misconceptions associated with some terms/labels used for people like me. I have done a lot of...
    garterbeltgirl19 garterbeltgirl19
    36-40, M
    Sep 22, 2011

    My beautiful wife and Mistress have decided to

    start our pages on here looking for friends and networking. I am 40 bi m who loves to be humiliated and made to dress up by my wife and suck **** and want to get ******. I would love to see my wifes sweet ***** ****** by a fat **** since I have such a small sissy **** ****. She...
    hersissycuck hersissycuck
    41-45, M
    Dec 9, 2013
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