At What Age Did You Start To Crossdress? / What age did you start cross dressing? Why

[DerekInNYC]

I first put on panties ( sister's ) around 5 or 6. Dressed in other articles after I was married and had access to more clothes. Have yet to dress with others, though. ( HINT HINT )

[Hermione Simpson]

when i was 7, when i tried on my sisters school uniform, as i wanted to know what it felt like to be a girl, although if you read my post in the earliest influence thread, you'll find out something else

[Stormgirl]

Around age 8 or 9

[NZ_Dawn]

Hard for me to say when it started exactly. Putting on my mothers suspender girdle, stockings and heels at 3 or 4yrs is closer to dressing up rather than consciously CDing. Otherwise I tried on my mothers pantyhose at high school at about 14yrs. This may have been the start but who knows. When my wife discovered the CD me, she asked when it started and I said much the same thing. I wasn’t really sure when it started 3? 4? & when I was dressed as a girl for a fancy dress party by mum? 14? or when I purposely went out and bought my first lingerie?

[lee james]

Tried on my first pair of panties when I was about three years of age.My first bra was at about seventeen.There was no stopping me after that!!

[nicki]

i was 11, started with my moms hose, panties,bra's and heels. hooked ever sense

[Sheri 4242]

Started at about age 3 or 4. Let's say I wanted to (and knew I wanted to, and that I was a CDer) from my very earliest of memories. The first time was when a neighborhood gg playmate and I exchanged clothes. I put on her denim skirt and she put on my pants, then we played house or something.

[Raychel]

I guess I was somewhere between 10 and 12. Then there was some sexual reasoning behind it. Now I just do it because I like it.

[Mollyanne]

I started when I was 11, I put on my moms nylons(no such thing as pantyhose back then) and a garter belt. Felt wonderful!!!! Bra and panties next, lacy slip and heels. My mom came home early from work one day and I was "caught" we had a long talk and she helped me from then on. She NEVER told anyone and took that secret to her grave.

Mollyanne

[ronda]

i started wearing moms heels and dresses at about 3 or4 and have not stopped yet love dressing efem

[Sarah Rabbit]

Well, I do not know about dressing as a girl, but my earlist recollections of 'wanting to dress as a girl' was about 8-9 years old. Does that count

Sarah R.

[kathy333]

i started because i had no clean underware for school. 1st grade. i remember my mom FORCING me to ware my sisters tights to school after i had them on and nobody was in the room i remember thinking "hay these fell good" after that i was hooked. i had my own stash spot in the basement, ware i hid the slips and pantys that i took from my sister.

[silkycd]

i began wearing my moms pantyhose at age 3, i cant remember that far back , but she told me about it. she had taken me to buy new shoes, and when she removed my old pair she was suprised to see i had her stockings on under my clothes. and as long as i can remember i have loved the feeling of silky lingerie, and hose,and i progressed to wearing leotards/tights for a few years, like all the girls on the aerobic exercise shows, then in my teens began to expirement with moms make-up,dresses etc,so it has been a lifetime of dressing for me, which i will never sop

[Jere Oneil]

I guess the first time I wore a dress was around 6 or so. My cousin (GG) and I used to play with dolls together and she gave me one of her dresses to wear one day, because, to quote her as well as I can remember, "you can't be the dollies mommy unless you are a girl". Even at that age, I liked the feel of wearing a dress better than boy clothes.

[denise19433]

At age 7,after my mom punished me for being bad by making me wear some ruffled pink panties because i had soiled my briefs.From then on i would sneak into my moms room and out on her panties,bra ,girdle and nylon stockings.
Later as a teen i would wear a bra and panty under a house coat as i helped mom clean our hose.
When i told her i was going to get married she said if i did i probably could never wear my ladylike things.That is not true as my wife knows i am a transvestite and mtf cd.

[Sara Kat]

I started around 10 or 11 by borrowing my mother's clothes.

[willowgurl]

My beginning was one Halloween when my friend Jonny urged and talked me into dressing in his sister's cheerleading outfit. His sister "borrowed" a wig from the scools drama dept. and did my makeup. I felt soooo sexy, and have been dressing ever since. willow. PS I also became Jonny's "girlfriend" that night and for the rest of the way thru H.S.

[Glenda]

I remember trying on my mom's bra and slip when I was very young (probably 7 or 8). I was always fascinated with women's clothes. I don't remember ever doing it again until I was 45 when a girlfriend wanted me to go dressed on Halloween. Seeing myself in the mirror brought back the early memories and I realized this has always been a part of me. Now I spend about half of my time at home dressed enfemme.

[cd_keira]

i was 13 when i first started cding, was looking through some drawers found my mums old clothes, assorted lingerie, bikinis, dresses etc, so i was trying on all the bras panties and tights, i remember how much i loved the feeling of the lacey fabric. i then found an old leotard, that really got me hooked, and when i found a bridesmaid dress and wedding dress there was no way out lol.

xxx keira xxx

[ChanDelle]

At about 3 or 4 I remember seeing my mom's brown suede heels w/ rhinestones in the closet and thinking they were much prettier than my dad's shoes. I really think that was the turning point toward CD as for as long as I can remember, I've had a fascination for women's clothing and jewelry. I do remember getting caught at about 5 with my mom's earrings and a necklace on (couldn't get the necklace off fast enough). Didn't get into any trouble, but felt embarrassed. Have been crazy about earrings and high heels all my life. Later in life my dad told me he caught me putting on my mom's lipstick at about 3. He was a very kind man and never made a big deal out of stuff like this. Still love lipstick too!

[JuliaCD]

I first tried on my mother's panties and a few other things at about 13. I wore her things on and off when I was home alone through my teens. I first bought some of my own things in college, and gave my then sweetie lingerie, always trying it on first, of course. Through my 20's and 30's I kept mostly lingerie around and only wore it behind closed doors as an added thrill when I...um...er...gratified myself.:winking:

At about 35 or so I discovered through the internet just how many CD's there are in the world and quickly developed an interest in more than lingerie. I began to dress completely, wear make-up and shoes and adopted my femme name. I discovered a feminine side of myself that has grown rapidly since. I know myself better and more completely than ever and have never been happier. My only regret is not figuring this out when I was younger.

~Julia

[JessicaJ]

From the time I tried on mom's panties n hose...no sisters..but only seriously without the purge for about 2 years

[BarbaraTalbot]

I hope this story isn’t too long or boring but I think it illustrates many of the quirks of fate that can befall a crossdresser. Maybe it’s very familiar to the rest of you and I just think it’s unique to me.

When I was 8 years old I had my first encounter with dressing. I found a box of my aunts clothes stored in our shed. When I opened it there was a pair of white high-heeled sandals starring at me. I don’t know why but I just had to try them on. A year later my mom tried to get me to dress as a girl for a Halloween party but I adamantly refused due to all kinds of fears including the fear that I might like it. Over the next several years I didn’t try to dress and didn’t think about it either. At the age of 12 I began to be interested and intrigued again by women’s clothes. One day when my folks went shopping I explored my mom’s things and put on a bra, panties, skirt, sweater and her red high heels. A rush came over me and I felt delightfully lightheaded. As I lay on the bed looking at my “breasts” I suddenly and thoroughly wet my panties. This was the first time I had had that experience and it felt so wonderful. Needless to say I looked for every opportunity after that to pretend and get that special feeling again.

When I went off to college the dressing ceased because I lived with a roommate in a dorm. I got married in my junior year to a sweet, attractive woman who liked to wear dresses and high heels. After two years of dating we decided to marry. She had no clue about the other me. We moved her things into an apartment the week before the wedding and I couldn’t resist sampling. Imagine my surprise to find that many of her things fit perfectly. After the wedding, I didn’t dress again thinking it was the right thing to do, as I was finishing school while she worked to support us. One night we were talking and playing around and out of the blue she said, “I wonder what you would look like as a girl?” I played coy and slightly uncooperative while inside me my heart was racing a mile a minute. Finally I let her have her way and she went to work – panties, bra (filled with grapefruits), stockings, slip, skirt, sweater, makeup, jewelry, and of course high heels! I was so excited I thought I would pass out. After an hour or two we had to undo everything and return to “normal” whatever that was at this point. A few nights later as I was feverishly studying I commented how calming being dressed was and how I was much more able to concentrate on the school material. To my surprise she let me dress myself in her things again and this began a regular occurrence. As they say once the genie is out of the bottle how do you get him/her back in? As time went on she began to buy me things on her own, makeup, dresses, shoes and even a wig. One night as we were leaving for the show she asked if she could borrow a pair of MY heels. I wasn’t dressed but I was so flattered and proud to be her girlfriend. Even though I never went out of the apartment as a girl, I was having a ball and since she was shopping with me and alone for me I thought she was very supportive. Wrong!

After I graduated I got a very good job with a fortune 500 top ten company. The dressing time quickly came to virtual standstill due to my wife’s sudden change in attitude about dressing at home and I didn’t want to jeopardize my career by doing it somewhere else. I managed a few evenings alone in the spare bedroom but when my wife became pregnant with our first child she said the dressing had to stop, the stuff I owned had to be purged and she didn’t ever want my femme self in her life again. I was in a real bad way; caught between my love for her, my new responsibilities of provider/father to be and the other self I so much wanted to be. There really wasn’t a selfish choice to be made so I did as she said and bottled my desires/feelings deep inside. Forty years later, with only a few isolated ventures to the femme side, the kids have all left home and I am now retired. I have more alone time now and since I don’t have to get up early each day for work my time to be me is late at night when my wife is asleep. I have procured a small stash again– 1 set of undies, one skirt, one top, a little makeup, clip-on earrings and 2 pair of 4” heels. I don’t think she suspects and she is still dead set against crossdressing yet ironically she is openly supportive of gay and transgender rights.

Don’t get me wrong by the tone of this story. My situation is not my wife’s fault. She’s a wonderful woman in all regards and I’m very lucky to have found her. I made the choices along the way on my own. Although I have lived with those choices all these years, I can’t help but feel like I’ve missed out on something. I’m glad I discovered this forum and I appreciate the company the girls here afford each other. It means a lot to a “girl” like me to know I am not the only one who struggled and is struggling with these feelings.

Was this too much information?

I repressed 35 years. I am 42, just got found out by my wife as I was preparing to show her me dressed. She is very supportive as yours was, I hope that since we went into this after a lot of reading, that she understands what this means and that it may well not be some passing fancy, she says she does. She is so supportive and I feel so lucky.

I was so sad to read how you lost that support.

To picture you, having worked and earned to support a family, having put this aside for the greater good, now in your autumn it seemed that you deserve so much more than a few baubles to play with in a lonely room.

I do understand the secrecy, I understand (if it applies to you) any feelings of not being entitled. My wish for you would be to be able to rekindle what you had with your wife. I know that is unthinkable to you, and I hope you are not right that it is. If you cannot, I hope that you can be gentle and loving with yourself and your soft sweet side and indulge yourself in small ways that are satisfying to you.

with tears,

Barbara

[BarbaraTalbot]

I started around 7 or 8, maybe even earlier, in my mother's "overflow" closet in the guest room... my mother and I were on our own, the sperm donor having split when I was about 5. I think I looked up to my mother and wanted to be like her when I grew up, never mind that I was a boy... She had a lot of pretty clothes (okay, nice for the late '70s anyway) and always dressed femininely -- she worked as the office manager for a financial planner and thus had a lot of nice clothes. When I was about 9 or 10 and in fourth grade, I started being a "latchkey" kid, arriving home from school before my mother got home from work... so that gave me even more time to "explore" my mother's closets, as I checked out her bedroom closet and dresser drawers. By the time I was 11, I was not only trying on her clothes, but her lingerie, pantyhose and high heels. In those years, I also stayed at a familiy friend's house when my mother was working, watched by dear Mrs. Holmes. I even explored hers and her daughter Nancy's closets when I had the chance.

Mother discovered my interest when I was 12, coming home early one day and almost catching me red-handed in her pink ruffled blouse and light gray skirt suit and heels... I was fast enough to change, but she found her clothes on the floor of her closet, confronted me about them, and as I cried about it, she encouraged me to talk about my dressing interest... and I discovered that she was actually okay with it -- concerned, of course, but not angry and only upset that I was sneaking around behind her back. So that all led to my mother's wonderful acceptance and support of my dressing, and her buying me girls clothes, makeup and everything else. Hey, it was just the two of us, who the heck was I hurting? Turned out also that Mrs. Holmes knew about my "explorations" as well, and she was also one of my biggest supporters -- she absolutely doted on me as Karen, and I had not one but two places I could go and dress up and be a girl, my house and Mrs. Holmes'. I even inherited Nancy's hand-me-downs -- all those delicious ruffled blouses and Gunne Sax dresses from the early '80s!

So that's part of my life's story.

This one made my heart swell with joy at the love showed to Karen. That her beauty and sensitivity was treasured and protected. Your mother was everything a mother should be. I feel so very blessed that the GG I married is just such a woman, not just to me as she recently found out. (I think I always knew she would be supportive, I just wasn't ready to accept me) but with how she is with our youngest boys beautiful sensitive nature, his joy at clomping around in Mom's heels. His eye for design. repression is so very ugly, acceptance is God's Love.

[Brenda Locke]

For myself, I can remember dressing in my mothers things when I was 8 or 9.
I didn't really start dressing fully until my early 30's though. Also the thought of dressing for a full day let alone part of a day or evening was just scary.
These days though i find it relaxing/liberating to get fully dressed and do so on a regular basis.

Hugs: Brenda