When did you first crossdress?

[cindi cinnamon]

Vixenvicki... I'm sorry, I should have been a little clearer with my statement... I meant Elance bikini's for men.

They served their purpose for a number of years, but I don't wear them anymore... Only the real thing for me nowadays.

[CastleCD907]

I started cross dressing when I was about 10 years old, I used to do laundry after school while my mom and dad was at work and I started to get curious about my moms underwear. When I started getting even more curious I decided to dig into my moms closet and found her lingerie and starting prancing around the house in it while no one was home. Once I started working and making my own money I began shopping at Ross or Marshall's for lingerie, panties, bras and started getting more serious and grew my collection. Now that I'm in my mid twenties I have had a lot of fun dressing especially now that I know how to do my makeup very well.

[teenagecd]

I remember that I used to dress up in the girl's costumes in kindergarten and play with them as if I was a girl. I was always a fairly girly boy and all my friends were girls. I was more likely to play with Barbies or princesses than superheroes or trucks.

It wasn't until I was about 12 though that I started dressing regularly. My mom had clothes that she stored in my bedroom which was formerly the spare room. I happened upon a bin of her old clothes as well as some cute heels I fit into back then. i put on the heels, an old dress and conveniently a wig from Halloween and felt soooooo pretty. After that experience I was hooked.

[Cynthia T]

Spring. I was 13 or thereabouts -- Only reason I know is that I didn't notice what my 7th and 8th grade teachers were wearing, but I still remember the heels my freshman Algebra teacher wore. Anyway, I was home alone, supposidly doing homework while actually reading a paperback, when one of the characters mentioned high heels. Suddenly whelmed, I got a pair of my sister's heels and tried them on. I've been borrowing/finding/buying girl things ever since.

[Katiekins]

My first time was when I was about 10 or 11, possibly earlier because I'm sure it was before I started high school (UK not American). I was in the bathroom and looked over to the laundry basket and had an overwhelming urge to try on my sisters clothes. Since then I doubt there been a day where I've not thought about dressing in some form.
Katie x

[Kandi Robbins]

Age 5, a dress behind the garage with the 2 neighbor girls. I still remember it 48 years later!

[Ellen2d]

I was probably 11 or 12 when I would sneak my sisters underthings. When I was 13 I went out for Halloween en Femme. I really liked it but really didn't do any more until I was in my 20's. It was in my mid 40's when I discovered a local crossdressers community. After going to my first meeting I went full throttle getting a wig, buying clothes and attending more meetings which were held in the party room of a local gay bar. The first time I went out on my own was after a makeup session with a pro. I went to the Mall Of America in broad daylight. There were a few shops there that catered to the CD community and I was treated very graciously. Today I'm older (20 years) and I don't venture out. IN fact I haven't done much other than wearing panties and occasionally nylons. Yesterday I had an urge to do more but when I opened the suitcase with my stuff I found it filled with mold. (We'd had a flood last year after a power outage, I thought I'd taken care of everything but apparently not) So I think I can salvage the wig as being synthetic it wasn't destroyed, just smells musty.

[claire_hollinger]

I would have to ask my mother lol. I have tried to dress since can remember. Ended up in counseling for it, and they even made it a rule of my juvenile probation (unruly child for dressing against my parent's wishes). I later had the rule removed as it violated my civil rights, but It was a very bad time. It wasn't until 2 of my brothers came out as gay that i was able to even speak to my mother about it without being judged.

[Mink]

2 gay brothers AND a crossdresser?

she must have felt like something was in the water!

[claire_hollinger]

She had my two older brothers, then me, then 9 years later she decided she wanted a girls and tried again. She had a boy, but thats because she ALREADY had a girl, she just didn't know it

[Joan.Meredith]

I was house sitting for some neighbors while they where on vacation and their girls were my age, and I tried on one of there swimsuits plus a few other pieces of clothing. That was about 10-11 years old, I already knew something was different about the way I was. It just helped me confirm that, "yeah I'm not like most boys".

Joan

[CorsetsnPetticoats]

For me it was probably around 6-7 years old and it snowed outside. My mother was worried about me getting cold, and made me wear my older sisters pink dance tights under my outer clothes to keep warm. I remember being embarrassed then, but it must have been the trigger that started on my path for a love of frilly things.

[Diane Douglas]

The first time I remember actually wearing girls clothes I was 15 and put on my sister's bikini for a minute or so. The first time I fully dressed was when I went to see Rocky Horror on Halloween with my GF and other friends. I had wanted to dress in girl's clothes several times before, but couldn't because it wasn't right.

[Pat]

I don't know when I started but I know that when I got caught I was 6 or 7. My Mom had a really nice bathing suit made of some kind of stretchy / slippery fabric. I found it in storage one day and put it on and felt so awesome that I hid the bathing suit under my mattress and every night after my brother fell asleep, I'd wriggle out of my pajamas and into that bathing suit and sleep in it. Early in the morning I'd wriggle out of the suit and get back into my pajamas. This went on for over a week. Then Mom changed the sheets and found the bathing suit. She told my Dad and he flipped out. He was shouting and carrying on and I learned a very valuable lesson -- don't get caught.

And I didn't get caught again until I was 11 and my grandmother found me where I had tied myself up to try to look like one of the girls on the covers of my Dad's "Men's magazines" from back in the day when they all had women bound up in skimpy clothing and threatened by Nazis or what-have-you. She wasn't at all cool with it, but she didn't tell my folks.

So many of us started in the single-digit age range -- long before puberty. The need to dress has to be baked-in, I can't believe it's learned behavior or choice. I'm on the right track, baby, I was born this way....

[tammie]

I first was dressed at age 4 by my mother who was put out with me for annoying my older sister and her friends , she stripped me naked and put ruffled panties on me and then lacy socks and maryjanes , then she put a blue gingham party dress of my sisters on me , that buttoned up the back (I knew I couldn't take it off by myself) .

This was so humiliating for me in front of my sister and her friends , I was both stimulated and shamed . I don't know if that helped influence me to put on my older sisters black underwire bra one afternoon when I was home alone .
But soon after I was caught by my mother wearing it and she got an eyeful of how much I liked it when she made me strip and took my sisters bra and LLPG away .

Wearing that bra that fit me like a glove , changed my life in that instant I got all adjusted into those lace cups. I still love it when I wear a brassiere just as much as the first time !

[amberporteraro]

My mother caught me at her makeup counter putting on mascara when I was 6. Haven't stopped since.

[Justice327]

I used to wear my mom's clothes at like 8 when she was at work or out of town. Luckily I was never caught. But I didn't fully dress (make-up, hair, clothes everything was about 2 years ago when I came out to my wife. She did my make up the first time I dressed for her. She picked my clothes out some me and did my hair.

[ashleymcculloch90]

Age 3, sisters pink tutu, mom found me and when I started crying said "it's ok honey you can wear anything you want. Still took me 20 years to admit to myself that I wanted to be fem all the time.

[toriryan332]

My foster parents were leaving town for an extended weekend and didn’t exactly trust me ( who can blame them…) so they decided to have someone house site with me. Cindy, the daughter of a friend of a friend of my mothers’ had agreed to watch me and the house for 4 days. She had told my mother that she was 20 and home from college, actually she was 17 and just wanted the money and a cool house and car to use for the weekend. When she showed up, my jaw hit the floor. The doorbell rang, my mother opened the door, and there stood the hottest girl I had ever laid eyes on, tight jeans, lace up boots with fur at the top, and sexy white puffer coat with black fur around the hood! After spending most of the afternoon and evening at the mall, we returned home and decided to watch a movie, Cindy suggested we change into pajamas and just crash in front of the tv. About 30min into the movie, we are both lounging on the couch, and I mention that I was cold and could she hand me the blanket on her end of the couch. She reached over grabs her sexy puffer coat and says “here just use this” and proceeds to snuggle up to me and cover us both with her jacket! I sat motionless, not knowing what to do or say, just taking in the moment, not wanting it to end. A few minutes later she asks if Im warm enough, and then starts to gently rub my arm as if to warm it up. I slowly relaxed and the next thing I knew her hand moved lower to my hip where skin was exposed between my shirt and pajama pants. It tickled and I squirmed, now realizing I was ticklish she proceeded to laugh and try to tickle more, which turned into a wrestling match. The next thing I know she is sitting on top of me, her coat between her and my pelvis and she starts to grind. After a few minutes she leans down and kisses me, and I started to have the weirdest feeling between my legs. She reached down, grasping my **** through her coat proceeds to stroke me, finishing with the first orgasm of my life. She rolls off of me and I go and change. I come back and curl up next to her on the couch and she covers me again with her coat. As we are leaving the house, I can’t find my jacket. Cindy tells me to just wear her coat and that she has another one she can wear. I look at her strangely, and she says…”just put it on!” I oblige her and look in the mirror as we are leaving. I love the look, although it is a little femme.
Once at the mall, we proceed from store to store looking at clothes and I was getting quite bored. Cindy and a couple of her friends start whispering and giggling. Next thing I know they have picked out some clothes and hand them to me and tell me to go try them on and model for them!

And Ive been dressing ever since! and I have an insatiable coat fetish!!

[tammie]

HI All: I swear some guys have all theluck.

[talonX]

I remember getting into high heels when I was around 12, then dressing as much as I could when i was home alone in high school - usually when everyone else was at church, oddly enough...

[fiseldon5]

My mom bought some panties for a neighbours daughter and I found them and tried them on. OMG. Hooked from there on.

[RobynT]

My earliest memory was very young,1st or 2nd grade and obsessing about a classmates yellow dress. I wanted one just like it. Didn't know why at the time, it was just pretty... Growing up in a house with my Mother and Grandmother, I remember them getting ready to go somewhere, putting on make up, in a slip and panties (age disclaimer, grew up in the 60's/70's..great vintage lingerie). It then moved to the clothes hamper, and quickly progressed to raiding moms panty drawer(one of the benefits of being a latch-key child). I dabbled for many years, including through a 15 year marrage, living in silence. Since the divorce, there's been no looking back

[DonnaP]

for ne grammar school sometime with my sisters sweaters and Bras and a few times with my Moms even tried best friends sister clothes once. Very scary when you enter another house when no one is home also very exciting and stimulating but never went back to much fear of getting caught.

[pinkDOT]

As a young kid, 6 or seven i used to play around with purses and stuff my toys in there at such a young age i did not understand why boys weren't allowed to carry such a cool gadget. I have also played a witch in a school play and wore a skirt (because I was the only one who could remember so many lines of text). Years went by and the first time i put some clothes on, innocently, was at the age of sixteen. I have asked my good friend who was opsn minded if i can try on her bra, panties, put on a tshirt and try on her jeans. She was ok with it and i was just being "curious". Well now I know that it was not just curiosity, it was something tht made me smile. It felt good