Post
Experience Project iOS Android Apps | Download EP for your Mobile Device
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Want to Cross Dressing

Personal Stories, Advice, and Support 893 People

    I Was a 16yo Boy / Girl

      I’d like to take this opportunity to share my first sexual experience ever when I was a teenage boy right after my 16th birthday. It was with my best friend. (Gary) and I have kept this secret locked up for many years and have just recently shared it with my wife My...
    timjanjon timjanjon 22-25 20 Responses Apr 3, 2009

    Your Response

    Cancel

    Somebody Else's Panties!

    This is going back a few years, and i know a lot of you wont be inpressed with what i'm about to tell you! but i imagine there is a lot of it happening, or would happen if the chance occured.you see i live near the countryside and one particular evening i was taking my dog a...
    femaletrouble femaletrouble 41-45, M 1 Response Apr 5, 2011

    Your Response

    Cancel

    The Pleasure Of Lingerie

    Hi Everone My story Iam a senior guy married but a very secret lingerie dresser, my wife doesn't know. I have been dressing on and off for over twenty years every so often I think Iam nuts and discard all my gear and say thats it but after a few months I find myself slipping...
    jamie20322 jamie20322 66-70 2 Responses Jun 5, 2011

    Your Response

    Cancel

    Chapter 4 - Shopping

    Weeks after our, what my wife Bev called 'a wonderful ****,' she said to me with, I must add, a smile and a raised eyebrow one Friday night, 'Tomorrow Jessica and I are going shopping and we wondered if you girls would be interested in coming?' Well, since 'that night' when we...
    Strombolix Strombolix 56-60, M Apr 26, 2011

    Your Response

    Cancel

    Could'nt Come To The Door Mate, Because I Was Dressed As A Woman!!!

    this happend to me on saturday night. i was dressed in my black bra matching black knickers, a petticoat, suspender belt with slinky black stockings. wearing a loverly flowing dress to top it off, an some cheap perfume, i'd brought it in a rush. then i was pouring myself a glass...
    femaletrouble femaletrouble 41-45, M 3 Responses Apr 4, 2011

    Your Response

    Cancel

    I Love My Partner Crossdressing!

    I have been with my partner for 4 year and wev only started crossdressing the past few months! We both love it and is such a turn on. He started off by looking through my clothes but has got his own wardrobe now. No one els knows about this and we love locking the door and...
    thechunkoflove thechunkoflove 22-25, F 14 Responses Dec 30, 2009

    Your Response

    Cancel

    Shopping Trip for lingere

    I am so excited because today I am going shopping today for womens lingere! Have you ever gone to a discout store like TJ Max and gotten a really good buy on sexy lingere. When the lady rings you  up I want to say yes these things are for me. Don't you thinklI will look...
    glen glen 51-55, M 5 Responses Apr 22, 2008

    Your Response

    Cancel

    Chapter 1 - Caught Out!

    My wife was away for the weekend and I decided to indulge myself by going into town and buying a few pieces of lingerie. That evening, dressed in my new panties and bra under a tight sweater and with just a silky petticoat I was enjoying my third drink in front of the TV when...
    Strombolix Strombolix 56-60, M 2 Responses Apr 26, 2011

    Your Response

    Cancel

    My Panties

    My CDing started at behest of my wife, and I regret to mos out on the opportunity I got few years back. It was then, few years after our marriage that my wife offered me her bikini panties to wear. I was very aroused, and pounced on that opportunity, and have never seen back...
    elephantelephant elephantelephant 36-40, M Jan 5, 2012

    Your Response

    Cancel

    The Urge Is Fading?

    just recently ive noticed that i am not enjoyin as much dressin up in my sexy bra & knickers? i wonder if orther crossdresses go through periods of not getting the same thrill as usual!! but there is mabe another reason why i have not been getting the same sexual kick out  of...
    femaletrouble femaletrouble 41-45, M 5 Responses Mar 7, 2011

    Your Response

    Cancel

    The Adult Book Store Adventure

    I am what the psych. community would call "bi-sexual" is suppose. In drab I have no interest in men what-so-ever, however when I transform to Samantha, well it's a different story. One night while I was out "playing" I was looking for some company for the...
    SamanthaLVCD SamanthaLVCD 56-60, M 2 Responses Nov 21, 2009

    Your Response

    Cancel

    Want to and Have

    I am a heterosexual crossdresser. I started when I was 9 yrs old and haven't stopped yet. You are exactly right, Once you tried it you cannot stop. I love wearing bras, panties, stockings and garter belts. I get so aroused and have such a hard **** in my panties that when wearing...
    BarbieB BarbieB 56-60, M 7 Responses Aug 23, 2008

    Your Response

    Cancel

    Chapter 3 - *** For Tat

    Friday night. Just my wife Bev and I at home, excitedly waiting for our visitors. I was dressed as my fem alter ego, Sammy. Bev had helped me with my make up and I think she was excited too. After my visit to Tom's place the previous week, when Tom had morphed into Cindy before...
    Strombolix Strombolix 56-60, M Apr 26, 2011

    Your Response

    Cancel

    Long Term Crossdresser

    I have been crossdressing since I was a child, it started with friends sisters clothes and items I found at school but as I got older I built up my own collection of sissy dresses, maids dresses and other items. My wife doesnt like me dressing so I do most of it whilst away on...
    Silkyanon23 Silkyanon23 46-50, M 1 Response Apr 22, 2011

    Your Response

    Cancel

    First Time With A Man

    Hi everybody. I have crossdressed since I was about 6 years old. My second wife found our (a whole story on its own) but we worked through it. I still have to keep it in the closet though. I was 40 before I went out in public dressed and what a great time that was for me. I am...
    SamanthaLVCD SamanthaLVCD 56-60, M 7 Responses Nov 15, 2009

    Your Response

    Cancel

    First Time!

    Well I was at my friends house, sleeping over for the night. I dared him to put on one of his mom's thongs, white cotton with lace around the edges. He then dared me to wear it for the rest of the night, i put it on and fell in love with crossdressing then. I have been dreaming...
    XXXcdXXX XXXcdXXX 18-21, M 3 Responses Nov 27, 2010

    Your Response

    Cancel

    Crossdressing

    i have been wearing knickers panties and thongs for as long as i can remember, the feel and touch of the materials has an amazing effect on me! if a girlfriend supports this then it can be a great experience but alas most women do not understand and can be quite annoyed by there...
    fenjoe fenjoe 41-45, M May 17, 2011

    Your Response

    Cancel

    Xdresser *****

    I want to be a crossdresser *****. I am looking for a dominate male to force femminize me and make me start a new life as your slutty *****. Make a sex slave living only to get my hungry holes filled with any **** you tell me to. Maybe this is the wrong forum to find someone...
    bobbilovescox bobbilovescox 31-35, T 1 Response Apr 19, 2010

    Your Response

    Cancel

    What A Wonderful Way To Relax

    I don't get to crossdress often but when I do I just feel soooo relaxed. I've always been it touch with my feminine side so when I do have the time to slip in to a nice dress along with panties and the rest I just feel so wonderful. I love being a guy but I also love my feminine...
    deleted deleted 26-30 Nov 14, 2009

    Your Response

    Cancel

    I Want to Cross Dressing

    I'm a crossdresser and I mostly buy my female clothes dressed a male or I use the web. I have gone out dressed as a female shopping for clothes but that was a long time ago, but anyway when I buy female clothes as a male I have no problem telling the sales girl that...
    cdlou cdlou 46-50 3 Responses Nov 9, 2008

    Your Response

    Cancel

    Pretty,girly And Totally Feminine

    I have ALWAYS, not only wanted, but needed to CrossDress in pretty FEMININE Girly clothes. I started sneaking into my mothers dresser and taking out her Lingerie and Foundation Garments, I was only 5 at the time. I felt so pretty wear her gorgouis slips and colored pantygirdle...
    carolannP carolannP 61-65, M 1 Response Nov 23, 2010

    Your Response

    Cancel

    CD Outside In The Dark

    Recently I have been having this overwhelming urge to get dressed up and walk around the streets at night as a girl. I am slender enough and could pull it off I think (my body is certainly slim and feminine) but I am terrified of what might happen if someone saw me. Just thinking...
    deleted deleted 26-30 11 Responses Dec 4, 2009

    Your Response

    Cancel

    From Crossdresser To Tranny?

    i have been crossdressing most of my life and it started with my friends sisters panties when i was only 5 years old. it progressed into more as a preteen and from there it took off into wild sexual experiences, and a lot of lingerie and clothes. then as a young adult i joined...
    Mizsuzy Mizsuzy 46-50, T 1 Response Nov 29, 2011

    Your Response

    Cancel

    Chapter 2 - Tom's Jaunt

    I was quite nervous as I left home, wearing my new bra and panties under my male clothes. I wasn't trying to hide anything from my wife Bev who had no issues with my dressing habits, but I had to walk down the footpath to get to my neighbour Tom's place. I had bumped into him...
    Strombolix Strombolix 56-60, M Apr 26, 2011

    Your Response

    Cancel

    Dressing In Womens Lingere Relaxes Me

    I have secretely been dressing in lingere for over twenty years. I would love to find someone to share some quiet moments and dress up.
    glen glen 51-55, M 6 Responses Apr 21, 2008

    Your Response

    Cancel

    Buying Clothes For The First Time

    I was in a department store looking at skirts and tops when a female shop assitant asked me if i needed any help I already had picked out a top so I asked her if she could help me pick out a skirt to go with it. She said My GF Is so lucky that I had no problem buying clothes for...
    emmareid emmareid 36-40, F 1 Response Oct 30, 2012

    Your Response

    Cancel

    Lucky Crossdresser

    My wife caught me dressed in her clothes many years ago.She took me shopping and made me choose dresses and underwear I liked.Then made me go to checkout to buy them which was so exciting.She told me she knew something was not right beacause I was not performing in the bedroom...
    sissylucy sissylucy 51-55 2 Responses Aug 16, 2008

    Your Response

    Cancel

    Want To But

    I have wanted to crossdress for a long time have worn pantties and pantyhose off and on for years. Wife din't realy like it but was ok with it until I did it most of the time. I talked to her about takeing futher like a bra and dress and she said no way and to keep pease I threw...
    yoemen yoemen 51-55, M 5 Responses Feb 28, 2012

    Your Response

    Cancel

    Chapter 3 - *** For Tat

    Friday night. Just my wife Bev and I at home, excitedly waiting for our visitors. I was dressed as my fem alter ego, Sammy. Bev had helped me with my make up and I think she was excited too. After my visit to Tom's place the previous week, when Tom had morphed into Cindy before...
    Strombolix Strombolix 56-60, M 1 Response Apr 26, 2011

    Your Response

    Cancel

    I Love This Time Of Year

    I'm a closet dresser, and have never given any serious thought to going out. I don't have the figure for it. Shopping for my feminine side is difficult too. I do buy some things online during the rest of the year, but during the holidayseason, I put on a wedding band I found in a...
    CrossdressingKen CrossdressingKen 26-30, M Dec 15, 2009

    Your Response

    Cancel

    Love It

    I started wearing my sisters clothes when I was home alone. I would put on lipstick and makeup. I loved wearing the pretty summer dresses. When we played dress up I would always wear a skirt.
    deleted deleted 26-30 Jan 8, 2011

    Your Response

    Cancel

    Cross Dressiiing Fiction Continued

    John friend, dan, had two sisters. These sisterscwere twins: two stuningly-beautiful girls with streaming blonde hair. John, going over to dans, would always watch them in awe of their beautiful. They ignored him. This was the way of life of john and dan. John had...
    Moroman Moroman 13-15, M Sep 28, 2009

    Your Response

    Cancel

    My First Lover

    Hi this is Apurba a 23 yr boy. Ummm Boy!!! Really I don’t think so because I never feel any attraction to a girl. Basically I am a boy but really not. Ok let me explain. I am third son of my parents. I know how I completed my study. And joined a company only on 2000 salary and...
    12s4 12s4 18-21, M Dec 11, 2011

    Your Response

    Cancel

    Washing Dishes

    Last night while my wife was out with the girls I had the house all to myself and decided it was time to let Jessica out to play a little bit. I had a sink full of dishes to do and figured why not bring Jessica out to do them, it would make it more enjoyable. So I went upstairs...
    JESSICAKNIGHT JESSICAKNIGHT 51-55, T 4 Responses Jul 15, 2010

    Your Response

    Cancel

    Man Boobs

    i sopose this would be a good thing realy with bein a cross dresser but for me it has its draw backs i have bein invited to go swimming with a female friend but i feel to self conious to show my body in public so have told her my about my little green apples she was...
    femaletrouble femaletrouble 41-45, M Aug 18, 2011

    Your Response

    Cancel

    No Guts

    Ive wanted to crossdress for years but Ive been afraid too.  How did you find the guts to live your fantasy?
    atuff atuff 41-45, M 3 Responses Jul 7, 2010

    Your Response

    Cancel

    Male Vagina

    this came about by chance, has i was rubbing my penis to get aroused through my soft knickers i pulled them to one side i was still very limp at this stage and i thought i wonder if i could push my penis inside my groin an i did! i looked down between my legs an it looked like i...
    femaletrouble femaletrouble 41-45, M 1 Response Mar 9, 2011

    Your Response

    Cancel

    Born to Be Beautiful

    Most of my time was spent trying on every possible combination of anything sexy in my mom and sister's wardrobes... nothing was off limits. My lust knew no boundaries. It was unquenchable. Literally. I'm sure I climaxed copiously into every pair of panties in the place. I...
    KaraSyrup KaraSyrup 36-40 Oct 30, 2008

    Your Response

    Cancel

    Wow

    I tried a bit of cross dressing years ago when I was a teenagre and then apparently grew out of it. Recently I was on a sex cyber room pretending to bea cd er I have now realised I really want to cross dress and I have this fantasy about sex with she males.
    Ludd2 Ludd2 41-45 1 Response May 10, 2011

    Your Response

    Cancel

    Cross Dressing (teenager)

    i really like cross-dressing i dont know why but i do! iv been doing it alotmor recently told my girlfriend and she cheated on me then dumped me told my lesbian best mate and she was ok with it a first made an afternoon of it at her house she did my makeup i got dressed.... and...
    Andixluv Andixluv 18-21 4 Responses Jun 13, 2011

    Your Response

    Cancel

    Cross Dressing And More

    Where to begin, I have been dressing since I was 5, it started with knee hi's and from there it has never stoped. I have always loved the feel of pantyhose on my body, just makes me warm and sexy all over.As I got older I would venture out more, my step-mom was a larger woman so...
    phlover48 phlover48 26-30 1 Response Dec 11, 2010

    Your Response

    Cancel

    Wearing Clothes Only

    i am a cross dresser that doesn't want to look like a woman at. i just wear at home or sometimes on weekends. i dont want to wear a wig, makeup nor do i want to look like a woman in anyway shape or form. i am just looking for a woman who will accept my cross dressing. the...
    jhmorpheus jhmorpheus 26-30, M 2 Responses Oct 14, 2012

    Your Response

    Cancel

    I Want to Be a Crossdresser

    i have always been a crossdresser and i never knew what that was. all i knew is that i always liked to put on my mothers nylons and wear her girdle.later on in life i finallw found out what i was and after years of anguish and lots of purges i finally came out of the closet and...
    phylisanne phylisanne 66-70, F 4 Responses May 14, 2008

    Your Response

    Cancel

    Crossdressing Fun

    When I traveled a lot on business, I always took women's lingerie with me to dress up in the privacy of my room and sleep at night in. Finally one night, I got up the courage to put on some lace panties, a leisure bra, and a camisole to wear under my slacks and pullover shirt. I...
    pantiescouple pantiescouple 26-30 1 Response Jul 19, 2010

    Your Response

    Cancel

    Never Caught Again

    Hi im 23 years . my story began when i was 13 years . exactly when i started discovering my body . i was in bathroom and i was so excited and suddenly i saw a bra belongs to my eldest sister( i have two elder sisters ) . i was tinking in trying it on but i was really confused...
    noala noala 22-25, T 3 Responses Dec 30, 2010

    Your Response

    Cancel

    Chapter 3 - *** For Tat

    Friday night. Just my wife Bev and I at home, excitedly waiting for our visitors. I was dressed as my fem alter ego, Sammy. Bev had helped me with my make up and I think she was excited too. After my visit to Tom's place the previous week, when Tom had morphed into Cindy before...
    Strombolix Strombolix 56-60, M 1 Response Apr 26, 2011

    Your Response

    Cancel

    Just Plain Love All The Eroticism Of It.

    I have crossdressed at some level or another since I was about twelve years old and I am 60 years old now.  It started when I was really horny and ************ at home at my foster mom's and spied her high heel shoes on the floor of her closet.  I could not...
    andieo1 andieo1 61-65 Dec 18, 2009

    Your Response

    Cancel

    My New Nose Pin Gifted From My Girl Friend

    i got gift from my girl friend , i opened it was a nose pin , my girl friend ask to me this is nose pin for you , you have to wear it when u dressed up , you can't feel complete female without it so i gifted you this
    jalvinmehta jalvinmehta 26-30 4 Responses Nov 9, 2011

    Your Response

    Cancel

    Want To Shop For Woman'z Lingerie And Clothes?

    Hey im a 17yr old male nd yes ii have crossed dressed before but ii use to rob my aunty'z bra's and panties but eventually ii stopped wearing them! Now ii want to cross dress again but ii dont want to be a thief so where can ii go to buy them?? Im a little shy and will be easily...
    canalboy1 canalboy1 22-25, M Aug 2, 2013

    Your Response

    Cancel

    Chapter 5 - Summer!

    This time I sat in the front while Jessica drove away from the department store where we had perhaps been a bit naughty and had nearly been caught. But we chattered about the fun we had had and were giggling like four schoolgirls as we relived our brief but naughty adventure in...
    Strombolix Strombolix 56-60, M 1 Response Apr 26, 2011

    Your Response

    Cancel

    Related Experiences

    I'm so looking to find a good cross dressing chat room as I would love to exchange pictures with transexuals, transvestites, & other cross dressers, CAN ANYONE HELP ?
    mick69x mick69x 51-55, M 4 Responses Sep 26

    Your Response

    Cancel
    I'm admitting now I have cross dressed in the past and purged in fear of getting caught my last purge was when I had lost my job and pretty much lost every thing in my life house...
    jkkarl jkkarl 51-55 2 Responses 4 days ago

    Your Response

    Cancel
    Yes, I did write about this before, but I just can't get over it. It happened years ago, and perhaps because my wife is very ill, I'm compelled to write this in more detail. While...
    LittleMelissa LittleMelissa 61-65, M 2 Responses 3 days ago

    Your Response

    Cancel