how old were you?

[BTWimRobin]

It started at a young age. Growing up, I had a lot of female influence in my house. By the time I was 11 or 12, I was always getting into their things, dressed, heels, lingerie, makeup. The curiosity, stayed with me through my teens. When I was 18 or so, I was dating a girl who enjoyed feminizing me. At that point I was hooked. Sadly, we broke up. Although the feelings never went away, life got the way and my feminine side went on the back burner. Around the age of 50, she started to boil over. She drove me crazy, almost to the point of a nervous breakdown. At 56, I finally accepted her and came out to my wife.

[Beverley Sims]

I played mothers and fathers when I was four, and was always the baby in the pram got pushed everywhere.

All sorts of dresses for me and this just carried over till about ten years old.

By this time I had been out dressed with the girls to family outings and parties.

[StacyG]

I discovered my sister's and mom's things when I was 11 or 12 and underdressed all through high school and college. Took a break from 24-32. After my first marriage failed, i got back into underdressing and sleepwear. I had custody of the kids so I didn't have any dresses or tops. Started exploring my bi side as well. Got married again at 50 and quit dressing. I'm 52 now and the movers are coming today to get all the wife's things even though we've been separated for about 6 months now. Not dressing related. Anyhow, I'm back and with it this time, I have dresses and blouses, leggings, hose, boots, bras and breast forms and much much more.

[Cheryl T]

I think my first realization came when I was about 16. It has always stayed with me and the last 5 years have solidified the fact that this is who I am.

[Jessica S]

I was 4-5 when I first put on some of my Mother's panties and hose. She would dry them over the shower curtain rod. As soon as I touched them I new I had to put them on. I'm in my fifties now. I have shopped at manys store in drab. But sometimes still feel funny about it other times not a care at all. But realized in my teenage years that I would always want to dress up but thought I was weird for wanting to. Till the internet came a long and I found all of us on here.

[Robbiegirl]

Remember Jamie and Harriet_.jpg

I have told this story many times, but I was about 6 when my mother and aunt made me trade clothes with one of my sisters to fool an old nanny that was coming to visit. The dress was similiar to what Lucy wears in Peanuts cartoon. I could not believe how much i looked like a girl and how fun the dress felt !
The whole episode lasted longer than expected as the nanny was over 30 mins late!
The episode reminds me of the tv show - Small Wonder- where Jamie has to pretend to be a girl - See Pic

[ShirleyN]

I was about 13 when my femme journey started and it was just out of pure curiosity and nothing more than that

[Lacey New]

I started in my early teens when I started noticing girls and was interested on those developing bumps on their chests and a mini skirt would offer a flash of pretty panties. I also started looking at the attractive pictures of women wearing lingerie in the Sears and Pennys catalogs. Eventually, finding either my sisters or mothers nylon panties in the hamper when no one was home was way too tempting and I put a pair on. I was hooked from that point on and would take any opportunity I could find to wear pantries for a few minutes and even on occasion, trying on a bra or a slip. However, I always felt guilty and feared that I was some kind of pervert or that I was gay even though I had no interest in other men. I had very little opportunity to satisfy my urges while I was in college but afterward, living in an apartment on my own, I eventually started to acquire my own collection of lingerie and other clothing. I guess that is when I finally came to grips with the fact that I was a cross dresser. It has only been in recent years since the availability of the internet that I have come to realize that there are many more men like me who are definitely not gat and who definitely do not want to live as a woman but simply enjoy getting dressed up from time to time. And that there is nothing illegal, immoral or fattening about it.

[Jenni6521]

I thought i might have posted in this yesterday. It does not look like I did. I was introduced to dressing at around 8 or 9 by my sister. She started dressing me in her bra and panties. She would occasionally put make up on me. I made no fuss about this attention frrom her and enjoyed the times when she would ask me "If I wanted to play dress up." She was six years older than I was. That got me started and I remember stealing this beautiful long gown off a neighbors clothes line. It had lace at the top with a pink flower in the center around the breasts. I loved that gown. My mother found it (never said a word to me) and took it away from me. She kept it in her stuff and I never found it, until I was cleaning out her house after we had to move her into a nursing home. It was like being reunited with an old friend. It is a little tight on me, but I can still wear it!

[candykowal]

My life as a feminine boy began very early as I was a undeveloped baby with a lot of issues with my lower torso and internal organs.
When I was born, the doctors told my mother, she had a daughter... and they realized my undeveloped nature, soon after.
I often slept with Mom in a satin babydoll's and diapers and plastic panties.
I was very coddled and pampered.
I was in and out of the hospital till I was ready for Kindergarten.
You can read about my whole story, in a condensed version (I could write a novel about growing up feminine!) by clicking on my Wordpress Blog link, HERE.
Use the PASSWORD: coddled ....to see the post, if needed.
I had so many people ask me about this subject, I had to write about it.

[laura.lapinski]

At a very young age there were thoughts. Around age 13 I tried on a bathing suit, but it wasn't until my twenties that I knew I liked to dress. As far as accepting that this was deeply embedded, it wasn't until late twenties.

[Lorna]

Although this question has come up on several previous occasions - and I responded - I think I have only just realised that it isn't just the age at which we started that influences our dressing but the period in which we started. I was in my early teens, but that was in the 1950s. If I had been a teenager in more recent years, especially from around the 1980s onwards, I doubt whether I would have seen much in female dress and fashion that would have started me off in the same way. The increasing and now almost universal adoption of trousers by women is a major factor. I understand that women's trousers/jeans are "different" from men's but, for me, not significantly different. I don't dislike tights (as opposed to stockings) but even they are now rejected by most women it seems. Slips, too, are not much in evidence. Of the clothes that intrigued me so much in the 1950s and 60s almost none are worn today. Even bras seem increasingly out of favour or regarded as an uncomfortable necessity.
Without repeating at length my previous contributions to similar questions, what started my interest in trying female clothing was observing girls my age and older and wondering what it could possibly be like to wear what they wore. As a teenager then, I was sufficiently grown up (but slim enough) to fit into those women's clothes and the experience was so enjoyable. The feeling of a dress or skirt over a slip was so good and the need for a bra, girdle and stockings beneath created such a totally different sensation that I just couldn't resist it. It also gave me an insight into girls' attitudes to their clothing: how they loved to look good even if some aspects of what they had to wear could be irksome - for example, the need to put up with a long bra and tight-waisted girdle to look their best in 1950s/60s dresses and skirts or the perils of going about daily activities while maintaining aspects of modesty such as not showing stocking tops and not getting ladders in stockings. None of those aspects, as I see it, would apply today and for those like me with no desire to become a woman but a strong desire to experience the clothing, I don't think I would have become a teenage crossdresser in the modern era.

[Jessica Secret]

13 and discovered my mom's sexy nighties and lingerie and was immediately fascinated and hooked, and today I have a bigger lingerie/nightie wardrobe than most teen girls or women probably have.

[Diedre]

I was 12-13. My mother did sewing and I got drafted as the dress dummy for things in my size. Once it became apparent I was enjoying wearing the clothes way too much, I got replaced by a dress form my mother got from a second hand store.

But by then the seed was planted and I loved wearing the panty girdles, longline bras, nylon stockings and slips.

[Kathi-Anne]

I was at JC Penney one Halloween. I was in the hosiery section. Beige tights in x-tall. When t got home, I slid the tights up my legs. It was heaven.
Christmas time,I bought a pair of danskin ultra shimmery tights in light toast, a must for any pantyhose lover.☺

[Leohose]

I was at JC Penney one Halloween. I was in the hosiery section. Beige tights in x-tall. When t got home, I slid the tights up my legs. It was heaven.
Christmas time,I bought a pair of danskin ultra shimmery tights in light toast, a must for any pantyhose lover.☺

Those danskin tights are soo comfortable

[SIZE=1]- - - Updated - - -[/SIZE]

Certainly. Leotards are super comfy

[SIZE=1]- - - Updated - - -[/SIZE]

I started in my early teens with wearing my mother's tights and swim suits. It was the 80's and the whole aerobicize craze was in full force. She would hang her items to dry on the door in my bathroom. I think I've finally gotten to that point where I don't question my dressing anymore. It's just something that I enjoy doing.

Leotards are super comfy so yes great first item

[josie_S]

I was 10 or 11 the first time I tried on my mom's bra. I was confused but excited. My older brothers would make me call their girlfriends bc they weren't allowed to get calls from boys and my voice hadn't broken yet so I guess I sounded like a girl. It was humiliating. I didn't feel like a girl and I didn't like that I was made to do act like one, so to speak. Still, cding and transgender stuff fascinated me, and every trashy talk show (Sally Jesse Raphael, Rikki Lake, etc) that had crossdressers on, I would watch and be fascinated. But it wasn't until I was in my 30s before I gave myself "permission" to enjoy crossdressing without feeling guilty. I still struggle with this part of me but I know it's not going away. I think I realized that the last time I purged. I felt so dumb after i threw out a lot of cute clothes and shoes. Once I decided to stop purging, I decided I wasn't going to throw out this part of me anymore either. I was 43 or 44.

[Rachelakld]

I often wore my sister PJ but my first outing I was 5, at home playing on the driveway and got busted by my mum, dad and sister.
I thought my sisters pink tutu looked nice on me

[Jane G]

Since I can remember. Though the firm confirmation was when I was about 7 or 8.

[Girly bride]

I was about 7 or 8 years old I used to play with my next door neighbour?s daughter and we used to play dress up especially after school. I used to love dressing up in her school uniform

[KimberlyJean]

This has been me my entire life, however it took until I was 37 to understand and accept who I am. Now it is a constant battle to maintain balance in my life.

[Rebecca60]

I was at JC Penney one Halloween. I was in the hosiery section. Beige tights in x-tall. When t got home, I slid the tights up my legs. It was heaven.
Christmas time,I bought a pair of danskin ultra shimmery tights in light toast, a must for any pantyhose lover.☺

I found a pair on Amazon.. Very nice.. I'm getting a pair for me..

[Candy]

I had "girlfriends" at a very young age, like 8-9 years old I think. I remember once my friend gave me her band uniform, a kind of red and white corduroy dress. I fell asleep wearing it one night... I think one of my parents checked on me and saw it, but never spoke of it. I didn't really think about it either or start dressing until many years later. I always wore men's underwear in bright colors and sexy styles.. maybe it was there all along? I always thought about the fact I have no visible Adams apple when guys comment that a crossdresser has large Adams apple, my neck is smooth.. maybe I was supposed to be a woman? I dunno, but happy with who I am

[Wendy-Lyn]

It started for me when I was 14, and found (yes, found) a pair of floral-patterned nylon bikini panties in our garden. No idea whose they were, I suspect the dog may have dragged them home from somewhere. Anyway, probably prompted by the intense interest in and curiosity about girls that puberty brings, I went into one of our sheds and tried them on (with the usual 'interesting' result). I kept those panties for a long time.

Never had a sister and never really got into my mother's things - a bra once, and maybe a slip.

I went through two SOs over the next 20-odd years, wore their panties and the odd dress occasionally but never when they were around. Told a third SO that I sometimes under-dressed - she was OK with it so long as I didn't 'push it in her face' (her words). She was good with me sleeping in a pair of panties. Her clothes were off-limits, but would not fit me anyway, so that was never a problem.

Been on my own for the last 15 or so years, and under-dressed sporadically, only wearing dresses infrequently. Had a big purge when I moved to my current unit 12 years ago but that, of course, didn't last and I began under-dressing again, with panties and a cami.

This May, I became very ill (not Covid), which wasn't at all fun as I could easily have died, and since then as I've recovered I've gone a bit crazy. I've bought bras and dresses, a pair of shoes, a couple of nighties, two cheap wigs etc. and made up some breast-forms out of some old panty-hose. I under-dress all the time, and dress almost every night to some degree. I found this forum, and have been reading with interest. I've even been out in public once, which I'd never have dreamed of doing before, and have started to experiment with some basic makeup. I think the health scare has somehow made me want to enjoy this part of me as much as I can before it IS too late. And so, here I am at 64... no shame, no guilt, just enjoying every minute of it.

[Christina89]

I was about 12 or 13 when I first started to try on my mother's clothes. For tines after that I thought it was wrong but also right at the same time. It wasn't until I was in my late teens early 20s that I realized crossdressing was apart of me and that wasn't gonna change.