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i think i first actually dressed when i was 10 or 11, i would wear my moms red silk nightgown that looked sexy as hell to me at least, i wore it with black thigh highs and a pair of white heals, i felt so beautiful that i was for ever hooked. when i was much younger than that i would walk around in my moms heals but that was just me being silly but i think i subconsciously new something was so right with wearing those shoes.
played a game with my cousins around 10 or 11 called gender wars!
we each dressed up as each other and just had fun with it, but i had a little too much fun and got really into it!
Yesterday!
I never knew I was transgendered until December 2012. And my wife hasn't been ready for crossdressing, so we've been sticking to easy stuff like painting nails, shaving legs, and makeup (yeah, go figure). But last week I spotted a gorgeous blue tunic on sale I just couldn't pass up. It arrived yesterday morning before work. My wife came upstairs as I was trying it on.
"How do you like it?" she asked.
"I love it! I can't believe it fits!"
"Well, I guess that answers that question," she said.
"What's that?"
"You like women's clothes."
I thought that would have been assumed, given that I'm transgendered, and all the other stuff that's been going on (TMI), but I guess she still had held out hope that I'd hate it. No such luck. She needed a hug.
It was euphoric - *intensely* affirming of my femininity. Must - have - more!
I first wore female clothes when I was 14, a friend from over the road left a gym skirt at our house after a fancy dress party at school.
I had done the usual dressing up as a small child in family and friends outer clothes and thought nothing of it.
But this one time I was very aroused by the idea, and went for it as I was alone. WOW it blew my mind and as I was a lone for quite a few hours it ended as my first W&$k.
I have stolen a lot of underwear from friends mums and sisters in the past, I know this is very vain but it was only from the very pretty females. I have now just bought a full wardrobe of my own, and am bursting (literally) to try mine on as they arrive.
I had a girlfriend/ Fiancée from the past who used to taught me by saying she wanted me to wear her undies. She never knew my past.
One night we were both very drunk and she said put the underwear on! I thought she meant me, but I now think/ know for sure she meant I put it on her. When she saw me in her undies she was visibly shocked.
This was the end of our relationship.
I continued to steal underwear every now and a gain, and have not been caught thank god. I don't know how I would have explained it. People need to know this was early 80's to late 90's.
I enjoy the feel and texture against my flesh, it gives me a massive sexual boost when in the mood to wear it.
I'm currently wearing a lacy bodystocking under my pajamas, the pajamas are only because of the cold outside.
When the weather picks up I have Stockings and suspender belt, black lace corset and a very sexy cocktail dress (strapless). I'm just waiting for my sexy panties and high heels to arrive.
Even in the cold weather if they arrive soon I will have a great private party for me! LOL.
Alison.
My Mother's stockings, when I was about six, but my favourite item of hers was a one piece bikini that I used to wear in my teens. I would put it on under my jeans and T-shirt. It was tight at the crotch and had plastic breast cups so I lost my bulge and got boobs at the same time. I guess that is what I am still after today, boobs and no bulge.
I remember bout 6 I relized how women cloths felt and could stop after that...lol
Four years old. Loved it ever since.
Wow! You must have married quite young.Quote:
Originally Posted by socalcutie
Like many here...in mom's pantyhose from the drying rack at probably 12 or so. They felt incredible on me and aroused me instantly! I then recall venturing into her closet and dresser and wearing high heeled boots of hers with the hose and nothing else. I can remember looking at my slender bare body in the hallway mirror with the hose pulled up over my nipples and feeling so sexy!
I suppressed or let it go as I got into my later teens until about 21 or so, just after getting married. Jokingly, one afternoon my wife said to me, "You'd probably look ok dressed as a girl" or something to that effect. It immediately rekindled the flame!
She likes to wear sexy things and we were quite young at the time...she had lots of sexy outfits and lingerie (still does :)). Not long after her saying that to me, she was out of town for a weekend and I slipped on a pair of her thigh highs...soon I was in a bustier and trying my hand at make up and lip stick. It was thrilling and arousing!
I spent the weekend in our bedroom dressing and decided I would surprise her when she came home...playing off of what she had said. Now, part of me felt a little strange..."What the heck are you doing?!" This was early 1991 and we didn't even have the internet then! I thought I was the only "freak" who dressed! lol.
I got scared she might not like what she saw, freak out etc. I decided, no way! I'm not going through with this and got out of her things and told myself "Never again!"
Haaaaaaaaaaaaaaaa Haaaaaaaaaaaaaaa
I don't actually remember the 1st time, i think i was like 12 maybe, but wanted to do it since i was like 7
I was around 6 years old... can't recall if the babysitter started me off, or if I did, but either way, I was pretty young but knew I'd never stop from the first time I wore womens clothes.
I must have been 6-12. I stole my mom's (old school!) pantyhose and wore them under my PJs with heavy wool socks. Had to have aroused suspicions, but we did NOT talk about these things...
I suppose I was lucky in that here in Scotland boys were expected to wear kilts from a very young age. I had my first kilt made for me at age 6. I dont recall too much about it but I do remember liking the feeling of not being trussed up in short trousers and underpants, which for boys then were always white and had buttons on the front. The answer then was for boys to wear girls school knickers and as my kilt was green based tartan I was given a pair of dark green knickers. This continued for a number of years and my mum liked me to wear a kilt to parties and to church and also I often wore a kilt to school and on any other dressed ocassion. I had a green tartan kilt and also a red Royal Stewart tartan kilt so my mum would always ensure I had the correct colour of knickers under the kilts. I remember at the age of about 9 or 10 realising that I envied the girls so much when I used to see their skirts or their girl kilts swinging and sometimes being blown up by the wind. At that point a kilt was the ideal answer for me as it is to this day. I did however start to actually crossdress in my early 20's when I got very curious and had a desire to feel what womens clothes really felt like. With a very red face I forced myself to buy a grey skirt, some white ladies knickers and a white blouse. Stockings and suspenders were a problem but I managed to pickup some in a department store and take them to the till in the hope they would fit! I couldnt wait to get the house to myself and get dressed and it felt fantastic when I did. I didnt have shoes at that point and I remember feeling that I just wanted to have boobs as well. I wracked my brains and as the blouse was quite generous I got 2 balloons and blew them up to the same size, stuffed them into my blouse and felt absolutely great. All a bit haphazard but thats where it all started for me. If I want to dress nowadays obviously I have the correct items of clothing and still enjoy it.
First recollection I have of doing it "fully" would be at age 12. I'm now 55 and more into it than ever. I feel "freer" than I have in a long time.
At age 6 or 7 my mother made my sister a dress. I liked it so much I made a fuss until she made one for me.
BTW, she (my mother) took a picture of me in the dress and didn't mind showing to anyone for many, many years. Ouch!
I think I was like 4 or something, pretty young, I think my mum and sister dressed me up in stockings and makeup etc. I liked it, but not when I got laughed at so left it alone for quite a while. Started dressing when I was a teenager at some point, worried about getting caught, purged. Now coming to terms with this other side of me and trying to enjoy it and let the benefits seep into other areas of life.
I think I was about ten, I tried on my sisters dress while my family were out. I was way to big as my sisters are younger, when they got back my sister somehow choose the same dress to try on and accused me of trying it on which I denied absolutely (could she smell me??).
Around the age of 5, was always fascinated when watching my Mum do her make up and getting dressed. Tried one of her dresses and lipsticks.....have never looked back!!
Around 1947 when I was 8. Neighborhood women were making dresses for a wedding (my mother was not there) and one woman suggested I might look cute dressed as the flower girl--they did and as one said when I was dresses I "was too cute to be a boy." That was it!
I started to explore around age three or four that continued into my teens to various degrees. I then went through a period of time where it was all mental and actural dressing would release the stress. I was in my mid twenties when I had access to full wig and makeup and when I first really saw Deidra as a reality and it scared me but I liked it, then went into denial, purge the whole nine yards which did not work. This continues to this day but only now am I understanding it, I now embrace it and what I thought was a curse is really a blessing. Where it will lead I do not know but I plan to enjoy the trip.
I was 5 years old my sisters dressed me up big joke for evreone but I was hooked
I was crossdressed by my mom as a baby and off and on until my third birthday(no recollection) when my dad took me to get my first hair cut, a buzz cut at that. My sister used to play dress up with me because she had no other girls to play with in our neighborhood. She would put a scarf around my head because I was still sporting a buzz cut. When I became a Cub Scout they had skits at every pack meeting. One time a friend from another den was dressed completely like a woman, wig makeup, nylons and high heels for for a skit he was in. My mom being a competitor made me up as a girl all the way too the next skit I was in. And so it went all the time I was a Cub Scout. The time I remembered most was and the time I really felt girly was when the Scout District decided to have a skit contest between the Cub Packs. I think I was 10 Jery and I had girl parts and were dressed to the nines. In the morning there was a run through so everyone would know what to expect on the stage and the in the afternoon we would put on the skits with the top six skits competing in the evening. We weren't dressed in the morning but were dressed for the afternoon. As luck would have it we were to compete in the evening as well. Jery's mom didn't want to dress him a second time so we stayed dressed and our mom's took their "daughters" out to eat. I was feeling so girly at that time I could hardly stand it. Being treated like a girl by all those around me including my mom. We even used the ladies room. I think before that evening dressing was nothing but after that it was really something and I couldn't get enough of dressing. That is when I started to dress on my own, mostly in my sisters clothes and bras.
I first tried on my older sister's pantyhose at around age 12 -- loved it but ran from it.
When my folks ran a big rumage sale one summer, I found that little purple short dress with the white lace in the front. I put on the pantyhose, and used a wire to zip the dress up. Loved looking at my legs in a mirror. Terrified I would get caught.
First crossdressed, knowing I was actually doing it -- Monday.
Oooh...whisper it to me ;>PQuote:
Originally Posted by Nikki50/50
For me,the first time unknowingly I was about 6 years old. My family was visiting some of their friends and I was in my friends room playing some game with her. Before I knew it I was in one of her dresses. I remember feeling like "hope my parents don't see this because this feels great"!
As life went on I was in my ealry teens and had an older cousin I used to run around with. She would always let me try on her newest micro mini disco dress and heels. I always had super long natural hair growing up,and while she let me dress she always braided my hair into a really cute ponytail. When no one else was at home she would let me dress up and be about the house all day and night. She knew I was becoming more feminine and she totally stood by it and we had great fun with it. Eventually I got a gf and by my early 20's we were living together. I expressed to her that I wanted to try on her lingerie and she was very cool with it even after we broke up,till this day she has kept it a secret to our mutual friends.
I started dressing full time when I bought my own home and me and my gg start hanging out a lot more. used to love waking up en femme,laying out in bikini's (had 7 acres of private land),walking down the driveway in a spring dress n heels to get the mail. I miss that privacy so much.
I was 6 and about to go on stage to sing at the high school for a holiday show and this well endowed teacher with her cleavage showing leans down and says wait honey you haven't had your stage makeup put on yet then proceeds to apply red lipstick. I can still smell her perfume and see her lace camisole. She then tells me how pretty I look and sends out on stage. On ride home I can still taste the lipstick. I'm mesmerized. Next day I'm standing in front of Mom's dresser reach for her lipstick apply it and well I've never lost the desire for feminine finery 45 plus years later.
I was six when I dressed myself. At earlier age my sisters dressed me up.
What a lovely memory...Quote:
Originally Posted by cdtraveler
Sounds a similar story this as to me though unfortunatly I can't remember the particular item it was the lingerie body is what i remember and wore the most. She had a black and a white one she never wore the white one felt a little sticky on the skin the other when I first began seemed the perfect size silky and had kept it hid it wore other stuff looked online on teen clothes websites; those and back when the pair of high heels fitted me perfect are good memories. Washed the body in the bath or sink damn nostaliga good times.Quote:
Originally Posted by Ceri Anne
The first time for me I was maybe 12 - 13 and I found an old blouse presumably belonged to my sister. I remember it was pretty wih lacy edges and I liked how it felt on me although I had no concept of cross dressing, it was just a bit of fun. It wasn't until my late teens I was staying at a freinds house his girlfreind had just left him and I found in his garden shed a bag full of her clothing, knickers bras etc. I just had no hesitation in trying them on and I've been hooked ever since.
Nicky
xx
My first time was 2 years ago...I was in my 50's. It took a long time to have the nerve to bring it up to my wife...it started with asking to put on a pair of her panties
The first time I crossdressed I think I was four. My mom used me as a model to sew dresses for my cousins. She dressed me and then painted my nails and put lipstick on me. I then discovered my grandmother's closet. The next step was my mom's closet who had a wonder collection of evening gowns and my first wig. I was seventeen when my mom caught me in her panty drawer. She and a her gf dressed me in a prom dress with the works. They took me to dinner and dancing. I later had girlfriends who would beg me to cross dress and then I would give in. Little did they know! My wife supports me after my mom told her about my teenager dressing occasions.
^ Seriously?
................
Another late bloomer - VERY late. I'm in my mid-fifties, and it was about 1 1/2 years ago. I was getting dressed after a shower, wife was in the shower, we just had a fight, and I thought to myself I could be a better woman than she is. Put on her panties. Escalated from there over time.
Age 13. Removing washing from the line and I just had to feel that satin and lace against my skin. My sister always had friends around and there was no shortage of pretty things to choose from.
First time out fully presenting as a female I was 16.
My GF's down the street who made me up as a girl all the time coaxed me into going to the senior prom with them as a girl.I was a Junior at the time.
It was great fun and needless to say a giggle fest for us.
Boys asking us to dance all that stuff.I told them I went to a different school and my date didn't show up.
I got to dance with the captain of the football team and he got quite fresh with me too,kissed my neck and grabbed my butt a few times.
Word got out around school later the next year that I went as a girl and I had more than enough girls to hang out with.Guys didn't like me too much but I didn't care.
I was always with a pack of popular girls so the joke was on the guys LOL.
I am guessing around 7 years old, stealing my moms silk panties. As I got older that progressed to lingerie and my sisters dresses. By the time I was a teenager, I had bought a few of my own items. Now I have a reasonable collection, although limited by the space I have to hide them. I think the best day was when I purchased heels and breast forms.
I was constantly being dressed in girls clothes from around age 6. I am the only grand-son out of 23 grand-children, They always liked playing dress-up and since I was out numbered they would doll me up in thier clothes. As I got in my teens my cousins had girl friends in other towns that they could get me to so that I could dress-up and go out with all the girls with out bumping into to many family memebers. Is tough when you grow up in small town Illinois farming communities cause everyone is related. LOL!!
Michelle K
I started with my sisters clothes when i 12ish. I do not remember exactly.
I went out dressed in college a few times and passed as a homely CO-ED but stuffed the desire for a while
I started dressing full time after my 1st divorce. purged and got remarried. Got caught dresseing in wifes clothes and she wanted to have me forcabl commited and drugged. Needles to say she is Ex #2.
Current wife has recently encouraged me to dress and go out. Even suggested I find a boy friend. She is a keeper.
This REALLY needs to be a sticky! Once again, 4th grade - won the boy's beauty pageant - things were never the same again!
all started for me at 14, mostly my sisters clothes as we both were similar size,now as ive got more confident with it im glad i started when i did and not too much later :)
Ok, I saw this and had to reply, for me it started when I was thirteen. It was a rather confusing time, I felt the need a few of my mother's things on and it was an electrifying experience, and oddly enough I felt normal. Of course, this was mixed with heavy doses of confusion and of me wanting to desperately be a girl. That lasted for a few years until I got use to being what I didn't know at the time was bi gendered. But I still remember those early times like it was yesterday. It is just amazing which memories stick around. :-)
i've always been fascinated by women's clothing for as long as i can remember - especially hose and shoes. I think the first time i ventured dressed as a female character was when i was 11 or 12 - i dressed as a witch for halloween. A few months later, i was in our bathroom and found one of my sister's skirt and blouse set. Just had to try it on. I remember it was made of some synthetic fabric that was soft and had a shine to it. The sleeves were tight all the way down, the skirt short and fit me like a glove. I looked in the mirror and loved the way it made me look. The thought of that outfit on me stayed with me from that time forward. A few weeks later, i was alone in the house - armed with fond memory - i decided to raid her closet. I found a short pleated gray wool skirt, a satin blouse, pantyhose and boots. We were the same size so everything fit perfectly. Over the next few months, i tried on pretty much everything she had - in secret of course. There was no doubt in my mind thats what i was supposed to wear. I was absolutly heartbroken when we moved (the bane of military life) and she decided to stay behind. She'd just graduated from high school and i'd just started. We had been living in NY and moved to PA. She stayed away for one year and so my dressing pretty much stopped. For some reason, i couldnt bring myself to try on my mom's stuff. It was so boring it just didnt seem right??????????? I was overjoyed when she decided to move back home. Best of all she brought back a whole new wardrobe. I picked up where i left off.
When i went off to college, i didnt dress for 4 years ... wow. the longest ever.
Some of it is still a fog and my memory isn't that great. But it was probably 1958 when I was 5 that I put on my grandmother's dress while she was my daycare at the time. I didn't get a thrill from it but somehow it felt right. I was probably 6 when I tried on my mother's girdle which was too big for me! LOL! My sisters and mother even painted my finger nails! Meanwhile my family humiliated and discouraged me from any other dressing. Then when I was about 11 I had an "ah-ha!" moment and "decided" I would love being a girl and being dressed. Devious little me raided my sisters drawers trying on their things and loving it! I was very careful to fold everything properly and put it back to avoid detection. (They probably knew!) Thinking back, was I pre-disposed to being a girl in my mind anyway?
Cheryl Ann
Part Two! (With joy and jubilation that I'm understood here!!!!!)
My first grade teacher in 1959 told me I had pretty blue eyes! (Translation to me---I should be a girl!) Actually my hair stylist told me to not use blue eye shadow and go for a rose color. WOO HOO!
When my sister got married, another sister was a bridesmaid and wasn't available when Mom tailored her dress. We were about the same size and I happend to be home. Guess who was the model! I didn't want to take off that gown! But...I had to...sigh.....
Cheryl Ann
Best I Remember I Was 5 Or 6 And Was Caught By My Mom Wearing Her One Piece Swim Suit Playing With My Brothers. Got The usual Threats And Learned To Hide Better. Progressed To Dressing Only When Parents Were Out Of The House And Trying On Clothes Every Time I Had The Chance. Hugs Riki!
Before i was old enough for school, about 3 I believe, I crawled under our front porch and put on a dress. I knew it was "wrong" so that is why I hid from my family under the porch. It took me 55 years to realize that I am transgendered and not a cd. Leanne
it was around six or seven. My mom put me in ballet so i started wearing tights at a young age. When puberty hit, the thrill of looking like a girl came into full bloom for me.
My earliest memory was at 4 years old. I had a friend over, and for some reason I decided to go upstairs to try on pantyhose from my mom,s drawer. When I didn,t come back for awhile, my mom and friend came upstairs to find me. I still remember the look on my mother,s face when she saw me standing at the top of the stairs in pantyhose. For years after that, I was fasinated with pantyhose and would try them on any chance; I had. I eventually moved on to girdles, bras, lingerie... the whole nine yards. I really wish I knew what motivated me to start with this.
6-7 I guess, mom's dress....then alittle older 10ish a dress, bra and lipstick...fully at 13 with a female friend.