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

[Marla]

I loved wearing my moms red lipstick when I was 7 or 8. Now I have my own.

[Charlene Ogden]

With me it really started with my fetish for nylon hoisery at the age of 5. I guess you could say that from the age of 5 til 25 I had a nylon/foot fetish. I still do. So that played a huge part. I also have a large 8X10 black and white picture that my sister took of me in drag at age 7. My sister recalls me wanting to dress in her clothes. I used to love wearing all kinds of costumes. I didn't think of it as crossdressing back then. I never dressed after that photo shoot til much later.
In my early teens, whenever I'd be at a friend's house, I would relish smelling their mom's or sister's nylons. In my mid 20's I could no longer suppress the urge to indulge my nylon/foot fetish so I went to a dominatrix. She encouraged me to wear pantyhose. That's how it started for me.
So you could say that I really started at about age 25 wearing hose. By age 29 I was going out in full drag.
kisses :-)

[Charlene Ogden]

I love this question. You can never ask it too many times. I love reading all the stories from all the girls. It's fascinating and ties us together through very common threads. Nylon threads. :-)

[DonnaT]

I had the desire when I was 6 or 7 when I saw a girl classmate had dressed her brother up once. I didn't start until I was around 10 or 12, when I came across some of my mom's old clothes while cleaning the basement, which I just had to try on.

[Sheri 4242]

Linda,

I first started at age 3 or 4. I am not certain which event came first, but I think it was when I would play with a gg (same age) that lived in our neighborhood. I was drawn to her denim skirts -- I knew I was supposed to be in a skirt, too. Don't know why, but it was overpowering!!!!

Anyway, we'd play "house" and I'd put on her skirt and she'd put on my pants. The other events that happened at about the same age (which is why I am not 100% on which hppened first) was I'd go stay with an aunt and she'd let me play by walking around in her high heeled shoes. I am positive that the two things mentioned were already going on when I spent the night with my aunt (probably age 5) and wet the bed. My aunt, a very small woman, put me in one of her nighties and WOW!!!!!!! It felt so GREAT!!!!!!! It confirmed what wearing the skirts had stared: this was me -- it was how I was meant to dress!!!!!!!

As to your next question, nope, never even came close to signing off with my male name.

George, er, Tom, er Jack, er . . .


~Sheri~


Oh, a BIG DITTO to what Charlene Ogden said above -- I love it when this question gets brought up from time-to-time -- love the replies and hearing the differing (and sometimes the same) stories about when people started and why!

[Linda C]

Thanx for the posts - I guess it all started for me at about eight years old. I was forced to sleep in my sisters room because we had guests - the next thing I knew I had put on her bikini and just felt awesome! From there - I started sewing my own garters by cutting a bra on the straps and wearing it upside down and sewing a pair nylons too it - and that was at age 11 -wow - what a long strange trip!

[RobertaFermina]

Age 20. My roomate the beautician and her beauty school mates did me up proper for Halloween.

From the start I could not stand to have a cheap or campy "drag" costume. I wanted it to be as realistic (passable) as possible. Once I got the clothes on, and recokened with the high heels, it was all about the feeling of gentle restraint (bra, pantyhose, silk undies) and relaxing myself into it....kinda flowing through the night. I wanted to explore "being" the woman in these clothes.

I repeated it about 6 times between 20 and 47.

As a kid, I had foster parents, and no sisters of any kind. I really did not like, and feared my foster mother and (remember kids are cruel!) she was mean and fat, so, if I had any idea about her 'things' it was followed by the urge to vomit.

Maybe under different circumstances I might have started earlier.....but I'll never know.

Roberta

[Jennilouise]

if i remember correctly i was around the age of 11 when i first wore my sisters bra. i suppose it was curiocity why i tired the bra on. the first time i was fully dressed was back 1999 when i had the money, time and the space. which i enjoy sooooo much.

[veronicagurl85]

For me it was very young I remember always going to the mall with my mom it was heaven she loved clothes and of course me being so small she didn't want to leave me outside to wait while she tried on clothes so I would go in. I had always wished I could be the one trying on clothes. Instead it was boring boys clothes boooo. But anyways my mom wore nylons all the time so that sparked my curiosity and I went for it and tried on my moms pantyhose and slip. I was in heaven I loved it. I was about 10 when I tried it finally. So that's how it happend

Vero

[Karen Francis]

At about age five or so, trying on my sisters ballet slippers and tights. All through elementary school secretly wished I could go to ballet class as a girl. Later as an adult starting branching into all sorts of female clothing, not just dance related.
Why? A large part is the feel of the material. I have a theory that TG persons have an elevated sense of touch and they derive emotional satisfaction by the types of materials and fit usually used in female garments.

[goofus]

Why? A large part is the feel of the material. I have a theory that TG persons have an elevated sense of touch and they derive emotional satisfaction by the types of materials and fit usually used in female garments.

Interesting theory...I know that the feel of the garments has always been part of the attraction for me as well..

[Linda C]

Karen - I think that you may be on to something!

[angelfire]

First time crossdressing, probably about 8. My 'girlfriend' and I would play dress-up. Never wore anything really feminine, but it was fun. Eventually, I took more enjoyment in it than her, and she ended up disliking it.

first time I wore something on my own was probably around when I was 15, a pair of pantyhose I rescued from the trash. I still don't know why I put them on that day, other than curiosity.

First item I bought for myself I think I was 16, and bought a pair of green pantyhose and white fishnets from a place that had halloween costumes on.

[Ashley Lynn Swift]

as i have said before i was about 5 or 6, it was at daycare, for whatever reason i never really related to the boys and never wanted to play the typical boy games with the boys like playing with cars, instead i found myself being befriended by a group of older girls, who always wanted to play dress up, (the Daycare had an excellent selection of donated little girl clothes), they always picked out the cutest pink dresses for me to wear and did my hair up in pig tails tied up with pink ribbons, and i would pick out these cute pink jellies to wear, the daycare usually was pretty cool about letting us stay dressed up all day long even when play time was over and its was time for classes and group activities, they would even let us go to the little girls room and change into the pretty little dress, of course they got p***** off when it was time to change back into our regular clothes b/4 our parents came and picked us up and they would find my boy cloths in the toilet. b/c i wanted to wear that pretty pink dress home.

[Alex-is]

Freshman year of HS was the first time i actually did it, but looking back there were little things i did thourgh out my childhood that wernt cross-dressing on their own, but were not things little boys traditionally do.

[Just Jess]

I had to be...13, 14 years old? I would babysit my aunts children and for some reason, I had an intense desire to wear her panties around. It sounds really creepy now that I think about it, a lot weirderd now than then. But, that's how it started. At least I don't do that anymore...

[lalaine_ty69]

i remember opening my moms closet and pulling out a pair of panties when i was 3. i spent most of the afternoons alone at home which gave me the chance to experiment with her undies and make up. i loved the feeling of wearing her pantyhose. i would be completely dressed in her clothes specially yhe sexy ones, high slit skirts, tennis outfit, bathing suit, sundresses, nighties. then i would go out and parade hoping that nobody i know would see me. only until i was earning money did i start buying my own clothes and a wig. it just fels so wonderful walking around in high heels. the sound it makes when you walk and how it makes your but move like a real woman.

[ErikaLadyoftheDesert]

I started trying on my sisters panties around 10 or 11 years old. It opened up a door that I never wanted to close.

One of my most exciting memories was one Halloween that I dressed up as Wonder Woman and went Trick or Treating as the sexy superhero. The interesting thing about it was that my Mother suggested it, and got real excited working on the costume with me. Maybe a mother always knows.

[Hermione Simpson]

i started cross-dressing when i was 7, as that's when i realised i should of been born a girl instead of male and i haven't stopped since

[Sharon]

I started at age twelve, or thereabouts, and it was the same time that I recognized myself as being a female, although it wasn't a peaceful recognition. It was just right.

[Daintre]

I was eleven when I started, as I recall there was a lot going on family wise at that time.

[Rashell StClaire]

I started at about 7. As to why, it just feels right.

same for me I just had to do it

[Jill]

For some reason when I was around three or four years old, I would pull my sisters pantyhose on over my pajamas at night and sleep that way. We were poor and lived in a tiny apartment where I shared a room with her. She would wake up and find me in them and get mad.

I don't really count that as crossdressing though, I don't really have any idea why I did that as a kid, I just liked to for some unknown reason. Fast forward to several years later, I think I was 10 or 11, I was just hanging out with my sister downstairs in her room, she was going through some of her old stuff and pulled out an old dress that she hadn't worn for a couple of years. She dared me to try it on and for some reason I took her up on it. I took off everything by my own underwear and put it on, I pranced around in it until she told me take it off, she could tell I was having to much fun.

I would say about a year or so later, I was home alone and wanted to do something "mischievous" and was soon standing in front of my sisters closet. First the bra then a dress. I was putting on dresses and skirts for fun but I won't forget the day that I first tried on a pair of pantyhose. That did it for me, I was truly hooked after that. I had three older sisters growing up so my clothing selection was very large. Those were some of the best years of dressing for me.

[chrissietoo]

One landmark would be at age ten, when I asked to be a girl for Halloween. Everyone asks what you want to be (cowboy, ghost, spaceman, whatever) and, having an innocent and true heart, I said I wanted to be a girl.

Full time hadn't occurred to me yet, and after the school parade, I went back to cowboys and baseball and eventually being a guy dating girls.

All the while, I admired girls' things, imitated their pretty handwriting, and brushed my hair back from my face like a girl would. I was pretending to be a boy, though, even as I would daydream about being a girl.

I would slip on girls' things for the thrill, in secret, and just for a little while, and my energy went into showing I was a good high school and college stud.

I was half way through college before it dawned on me who I was inside, and that slipping on my girlfriends' bras was not just a kinky habit, but a deep expression of who I am. Ahd that's the second landmark, though it's really just the return of the first...

In my sophomore year abroad, I had met a Norwegian girl and after a passionate summer I had to return to the US. Her best friend was an airline attendant who flew to my city, and when she was in town we'd have dinner and she brought gifts and gossip from my gf.

Inger shared an apartment with other Scandanavian flight attendants, and on Winter Solstice, Inger invited me to join them for a traditional celebration. The most stunningly beautiful girl dressed in white with a crown of candles, and we went around the neighborhood (a very hip artists area) visiting friends, singing and bringing food treats.

My roll was to carry a tray of food, and they dressed me in pantyhose and a tunic. I was in bliss, in pantyhose surrounded by pretty girls! When we got back to the apartment, I stayed in the pantyhose all day, and I remember so distinctly feeling like one of the girls.

Oh, and the girls were coming and going, crossing in front of me to go to the bathroom to dress, or change clothes, or tinkle. I felt so comfy and warm in my pantyhose, and so soft and feminine to be in that house! I became a frequent visitor, and, as I look back, although I told myself that I was there to dig on the sexy women, but really I was there because I felt like one of them!

I would mark those months as when it really began to dawn on me that I identified with the girl inside more than the guy in jeans and boots.

I began to collect some feminine things to wear, starting with pantyhose! My g/f and I grew apart, and I didn't date for a while, but I was very busy in the closet, and continued to visit the girls, now dressed in panties and some of my unisex clothes.--I'm sure many of you understand.

The next girl I met and dated was pretty and frilly and her look sent shivers through me. When she took me home to her place, she flipped me on my back, kissed my nipples, and set things right. When I told her that night that I'd been dressing, she laughted and said she'd pegged me for a girl from the moment she saw me! Like it or not, Chrissie had reappeared~

[naomi2009]

When i was about 4 i think i very briefly had one of my mums old skirts to play in but i dont count that as my first time. At age 11 i had my first real oppertunity to try dressing, i had been waiting for the moment for many years and it did not dissapoint!
I wore my mums dresses, underwear, shoes, the whole lot really, i loved every second. it went on for many years. now i buy and wear my own clothes whenever i can.

Love to you all

Naomi xx