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Hi to all my wonderful friends 🙂 . A nice easy topic to answer 🙂 . How old were you when you first crossdressed? Seeing other members answers to this in various posts, I came to the conclusion, its very varied. I guess most crossdress before age 30? go on girls, prove me wrong! this should be an interesting poll for you all 🙂 .
Fiona xxx
I was always interested in wearing the pretty things that only the girls could wear as far back as I can really remember. Now acting on that… I did have a pair of my mom’s heels I walked around in at a really young age more than a few times. I remember them vividly.
It was pre-school, and I started school around the age of 4 years 8 months, so before then.* I must scribble out my early tale sometime. School itself made me realise that the genders were separated by many artificial and needless rules (Why can’t I play in the Wendy House! Why can’t I be an angel in the nativity! etc.)
* Hey, that means I’m around my 50th anniversary right now! Yay! Go me!
Hi Fiona. Even though it doesn’t have any scientific value, I dare to say that young boys who started trying on and / or wearing girls/women’s items of clothing were far less interested about the sexual aspects of crossdressing than those who got started during their early teens. (At least I know that is how it was for me). True, in my teens there was a close relationship between dressing up and sexual excitement, but when you are a teenager there is a close relationship of anything with sexual excitement!! 🙂
My oldest memory of me wanting to wear any item of girls clothing is from when I was somewhere around 3 or 4 years old. Then a bit later, when I was maybe 5 I ended up having to wear at least a couple items of girls clothes after a family picnic since I had fallen into a ditch and my own clothes were covered with mud. My mom didn’t pack any spare clothes and we were just minutes away from my aunt’s home so they took me there to take a bath. Now she only had 3 girls, the youngest just a bit older than me, so I had to borrow some of her clothes.
Anyway, posting this before I get over the limit of characters…
Gaby
i was about 11 or so. in school. had a school play had to wear green tights for the play. the play was snow white and the 7 drofs , i was scared at the time but when i put the tights on i was hooked, the feeling of them was out of this world, message feeling and when walking it was heaven. i became a x dresser slowly. it went away for years. then came back in my 30s. now in my 50s i have more female cloths then wife and more make up then she does. wife knows of my x dressing but will not let me sit with her and talk like 2 woman. she has seen me getting dressed up but would not help with make up or style my wig or any help. so here i am on the net for friends to talk to that under stand. i love to dress up and be pretty for that is what i should of been a female. when i dress up its like normal for me to dress in female cloths. even tho i am male. woman dress in male cloths all the time so what is wrong with men wearing female cloths?
I started actively dressing at fifteen. Our family didn’t have the funds to spare to buy my sister and I nice clothes to wear, that all changed when my father came into an inheritance from his fathers estate. We moved from the city to the burbs and our lives changed, My sister got several nice outfits and went from drab cotton panties to pretty nylon underwear and nightgowns. We shared the same bathroom and laundry hamper, seeing those lovely panties and nighties got me wanting to try them on I could not resist myself any longer I was holding one of sis’s nightgowns when I was caught by my sister. She did not get angry in fact she was very understanding and let me wear some panties and A silky nightgown to bed. I found out later my dad and my uncle both cross-dressed so I never had the feelings of guilt and shame so many of us have had to endure, never had to purge my stash, after reading the stories on CDH I realize what A lucky life I have.
I was 4. I would wake up in night and put on mums knickers and tights and go and sit for a wee
later became more serious around age 13 and I would dress fully and go outside when parents not around
had my first sexual encounter at 15. Parents away for night and I went out around 11pm for a walk in mini dress tights and heels. Got picked up by old guy in car who thought I was a girl. I told him I was on my period but offered him a bj
still remember the smell the feel the moans and the taste xxx
It first occurred to me aged 5 or 6 when I saw a girl in a skirted one piece swimsuit and wanted to wear it – I mean really wanted to wear it. I daydreamed about it for a long, long time!
I liked dressing up from my sisters dressing up box – always wearing dresses and my mothers old heels which were in there. My mother put a stop to that.
So my first proper experience came aged 11, during the hot summer of 1976.
My grandmother presented my sister with a waist slip. I had never seen one before, and thought it the prettiest, lightest, coolest thing to wear, and simply had to wear it before my sister did – the very thought of wearing it after her seemed horrible to my 11 year-old mind.
So I waited until I thought she was asleep, stole in, grabbed the slip, removed my pyjamas and put it on. Ahhh! The sensation was even better than I imagined.
But in the half-gloom came my sister’s voice; “What are you wearing – is it my petticoat?
Hastily I slipped it off, put it back in the open drawer behind me, lied “No, nothing” and scampered back to bed.
That taught me to be a lot more careful, and to hide as well as possible.
Grrr! That we have to hide!
I still cannot think of a single reason we should hide except to appease others and thus confine our own lives to a second class status.
Oops – off topic!
Laura
I was about 8 or 9 years old when i first dressed up i used to wear my older sisters clothes when i was alone in the house, i didn’t know at the time what it was all about i just thought i was just dressing up like when you put on a cowboy outfit or a uniform to play at cowboys and Indians or at being in the army, it wasn’t until i was in my late teens early twenty’s that i suddenly found out that i actually liked wearing women’s clothing and would continue to wear them when ever i get the chance to, I’m always looking in the shops and magazines at the latest fashion’s for women especially at the lingerie and what the latest dresses are in fashion, sometimes i wish i could take it a bit further and come out of the closet we shall see what the new year brings, happy new year to everyone hope you all have a good one hugs Rozalyne x
i was 4…a neighbor girl aged 5 came over to play and she said lets hide on my mom so we hid behind this big chair…then she said lets switch under pants…so i took mine off and gave them to her and she gave me combed cotton with cherries panties…i put them on and felt so really good in them…so soft and comfortable…that started it all…i would check out my my moms lingerie drawer and would put on some of her things…the feelings were beyond words…i loved the feel of nylon antron 3 etc….as i got older around 11 oe 12 i would ride my bike down to the 5 and 10 visit the lingerie department …i would take pantaloons and panties and stuff them down my pants and walk out got home and immediately try them on…the pleasure was intense…i was so hooked….one time i slept over at a friends house and i would go through his sisters lingerie and closet..i tried on my first slip and slept in it….what an experience ….continued onto college and as an actor i would go into custume room 20 to 30 years of clothing…especially womens gowns nighties sheer blouses etc i was in paradise…i would bring them back to my dorm room and live in them over the weekend while my roomate was gone…for me as a adult i love the pleasure and sensuality of the female under things…im hetero i love women and what they wear and experience…however i would purge my lingerie from time to time….feeling quilty…ive been married twice my first wife never knew…my present second wife found me out and stopped sex completely and said i make her skin crawl…she found these underthings ….i told her im turned on by lingerie and the feel of it and use it for masturbation purposes…she didnt care and is a prude to say the least…very unforgiving , hateful, disrepectful…she is pretty much a tom boy and rarely ever wears sexy lingerie or a dress or stockings…plain cotton panties, plain white bra…pants always …thick cotton pajamas etc…so for 15 years no touch, kisses or hugs…ive begged her to get counseling many many times…she says counselors are phonies and scam artists…i dont know why ive loved lingerie so much…going into the store and seeing lingerie dept full of a sea of color and every fabric imaginable…the mens dept is one gondola of under pants…what choices women have and how lucky they are to have soft hair and even softer skin and then breasts so soft and nipples so hard…their curves so wonderful and their smiles melt me…beautiful and perfectly made…
It is amazing that you have stayed with your wife for so long.
I am in a similar situation. I am not completely cut off but may as well be.. I noticed when (in secret) I would wear my s o clothes she would never wear that piece again if she knew I had worn it. After 10 yrs with her I dont wear her things anymore they are way to big for me. . I always say I love women. However, if I want to have a sexual encounter involving lingerie, I have to wear it. I don’t mind doing that either.
My crossdressing started when I was about 3 or 4 years old. My (late) mother took me next door to the neighbours house. They both dressed me fully in girls clothes, and even ribbons in my shoulder length curly hair. When I was about twenty eight, I tried on my wife’s bras and panties. Then in the last two and half years, I cross-dress daily. I wear women’s panties every day, (since 2016), only wear men’s underwear for hospital appointments. When I get home from work I change to Marie, bra & breast forms, panties/shapewear briefs, pantyhose and shoes. Feels so calming and relaxed, and so womanly & feminine.
Probably about 8 or 9. There was an old trunk in our garage and it had some dresses in it. I was fascinated by these and just had to put one on. I think my love of period costumes stems from about the same time when I read a book about all the finery that was female period clothing. I was hooked and these days own 3 examples, one American Civil War Ball gown and two 17th Century French, (with panniers to match).
I also remember trying on one of my mothers swimsuits with rather itchy tennis balls for breasts!!!
Some of you ladies have commented on how you were caught dressed. My folks had a weekend place by the sea and in my teens I refused to go there in the winter, cos there was “nothing to do”.
So I was left alone for the weekend with the treasure trove of all my Mum’s things. Some “rellies” came to check on me one night and I was well and truly “sprung”.
My father , being the “product of his generation”, ie the typical 60’s Dad, told me that my disastrous fate if I did not stop dressing, was that “the boys in the pub will call you a queen”.
Quelle Horroeur!! (Cant spelt that, but you get my drift!!)
It brings a smile now, but it was not funny at the time….
Two more “parentals”.
My old man used to tease me about buying me a pair of pink panties…. I’ve often wondered if subconsciously, “it’s all his fault”…. (Lie down on the couch Caty and tell me all about it… But first,,, here’s my bill!!!) But if he was still around, I might buy him a case of beer and say “thanks Dad”!!!Dressed in my best Caty finery of course… He’d probably need the whole case to recover from it all!!!
I used to have a fascination with strapless bras. So at the tender age of about 12, I cut the straps off one of my Mum’s.
I dont think she was all that impressed.!!…
Happy dressing
Caty
Well I guess I’m only the one of a few who discovered these feelings much later in life. Before 60 ,well maybe over time I just bang my head too hard ,I don’t know but it’s been one of the happiest things that has happened in my life. Other than my marriage and family my journey has been most fulfilling and having many of you as friends well that’s priceless ..
Stephanie 🌹👭
I was around 12 or 13..My mom put satin sheets on my bed ,at the time i did not know what satin was..all i knew that it felt so nice against my body..At first I did not think of it as sexual.I just loved how they felt..I loved going to bed knowing how much I loved getting between the sheets…about the second week I woke up hard. That had never happened before .It was my first erections and it felt so good..I also had a climax every night and morning for the next week…which I had heard about…..Then one Sat. night I got in bed and OMG no satin sheets..I did not know what to think…I all most cried…I went looking for them everywhere…I could not find them so I looked into my moms room ..No one was home. I opened a draw and wow it was full of woman’s silky and satin things… I knew about panties and bras but that was about it ..There were long silky things that i did not know what they were called ..long nighties and negligee’s.I took a negligee and a nighty and panties . to our attic..I could see if anyone came home from there.I put on silk panties nice pink ones and a satin light blue negligee. I lied on the bed and was hard in a min…Omg it felt sooooo nice silk and satin wrapped all around me..I climaxed twice that morning..and lied there for over an hour with chill and feeling going through my body. I spent many days in that attic enjoying myself and have crossed dressed ever since..with out any one knowing..I found out when I was around 16 that it was called cross dressing and many men did it…I still love it i love feeling girly in girly cloths .I become Lisa Ann.Thanks for reading my secret .and it all happened because of “satin sheets ” I guess I can say my mom made me do it LOL Love, Lisa Ann
I was young, probably around 6 or 7. A neighbor girl and I played doctor a lot and I remember once “trading” unserwear for a day. Around that time, I started experimenting with my mother’s clothes, mostly girdles and stockings. Throughout childhood and adolescence, I would pretend to be sick so I could stay home from school an spend the day dressed. I developed a love of girdles and, eventually, pantyhose that I’ve never lost.
I first started dressing in my mother’s clothes when I was 5 or 6, mom and dad found out and I had to stop. It wasn’t until I was 13 or 14 that I started dressing again, mom and dad were not to happy. I was sent to a therapist, all that did was to reinforce my cross dressing. Back then they didn’t treat for being transgender, you were ether Gay or sick or both. I’m 72, I have been married for almost 50 years, and my wife has known for more then 50 years, she purchased my first nightgown before we got marred. About 8 years ago, my wife suggested I join a transgender support group, I did, I go out dressed more now, and I even have a California ID with my feminine picture on it. I enjoy being a girl.
Hugs
Ronda Francine
Interesting stories! Well, here is my first time. I was about 22 at the time bought my first boat. Took it to the beach and plopped down in my beach chair hiked up my shorts exposing as much skin as the law would allow. I got sun burned or should I say sun poisoned so bad. I went to work Monday in so much pain from my male underwear band. When I got home my wife gave me a pair of her panties that sat below the burn area in all areas . That was it the comfort of the panties was more then any pair of mens undies that I started wearing full time. I then began to check other things and loved it.
I guess I was around 6 my grandmother made me wear a swimsuit and I love it and remembering dreaming of being a girl,then I remember finding my sisters clothes panties knee highs pantyhose dresses oh my god I was in heaven I would dress up every chance I could get I just wish I didn’t have to hide the real women I am. I guess we’ll see what the New Year brings cause Lauren really wants to come out
Around 10 I will take a guess at. My sister and her friends who were around 5 years older than me would ‘mess’ around at sleep overs and I thought it was fun at the time and felt that it was not doing anyone any harm. Years later the fact that my sister was involved horrified me and has had an impact on my adult life. Im going to make it easier for me by saying that finding our birth certificates and realising she had the surname of my mums parents made her think that we wernt related so it was ok. My dad adopted her as mum was a few months pregnant when they got together. At the time I thought it was great fun and felt rather lucky that a couple of her friends who were rather sexy took it upon themselves to experiment with me. Looking back this would nowadays be classed as paedophilia Im guessing? But they were 14/15 and I was 9 or 10 and I took great pride in telling a few close friends who many years later I had the same discussion with as it was affecting me and I felt I needed to tell someone. My very close friend couldn’t decide whether I should tell my mum about this but after a few years it got too much so my wife and I arranged a meeting with my parents and I told them. There was a very long awkward silence and it was never mentioned again obviously it changed the relationship between my parents and her (dad by now was not keen on her anyway)
Interesting thread, I must read more of the stories.
For me, well before 10. I remember trying on my mum’s slips. Oh so soft and silky!
Then, in the mid 1960’s, the mini skirt arrived as ‘a thing’ from Britain. My mum was an amateur seamstress, so many of the neighbour girls wanted a minskirt – cheap!
I had about the same waist size at 9 or so that many of them did. Guess who she got to be the manequin?
(Mum I don’t think ever thought this would affect me – Is CDing nature or nurtured? I think it just awakened things myself).Fast forward to primary school (5th grade). All boys class and I got cast as a female in the end of year play.
…And many dot points I can join up after that – fancy dress parties etc.
It would have been when I was around 5 or 6 years old. I found that wearing them calmed me in the storm that was our household. Only did so very sporadically for about 30 years. I started back crossdressing frequently a few years after marrying my wife when we were, ummm, experimenting in the bedroom.
I was very young – 4 perhaps – at least before my dad married my step-mother, and I was 5 at that time. I recall being at the babysitters, with a few other kids, all of a similar age, and we were playing some kind of cops-n-robbers thing, or similar activity, and I was the ‘victim’. I was ‘tied’ with a jump-rope, and for some reason I had stuffed a teddy bear or something under my shirt so I could be a proper ‘damsel in distress’. I have no clue how or why I would have conceptualized this, but I spent maybe a good 15 minutes with stuffed breasts, tied to one of the basement floor-jack poles, and I loved every second of it enough to remember it some 40 years later. (I am deeply submissive to this day, and my kink-streak is a mile wide!) Around this same time, my father (pre second marriage) found me coloring red stripes on my legs with a marker. He asked what I was doing, and I told him I wanted to be Raggedy Ann – not Raggedy Andy, mind, but Ann. I had both dolls and the only one I ever played with was Raggedy Ann.
Around 12, when I slipped into my older sis in laws panties, then a skirt…. then a dress.
Technically could have answered two ways. Consciously I was 11 when I first crossdressed; BUT my oldest sis dressed me when I was 4-6 though I have no conscious memory of it-just family anecdotes about it. That is where I got the name Cynthia!
CynI was ten.Nearly every Saturday I used to go to my Aunt and Uncles house.When they went out for the evening my two female cousins used to babysit for me.I was particularly friendly with the younger cousin who was nearest in age to me five years my senior.As she had started to wear tights two years ago,I got more and more envious of her as I longed to wear them.One night I asked her to dress me up in a dress and tights.I don’t think she was keen on it but she relented, gave me one of her dresses to put on and she and her friend put makeup on me,alas no tights. it felt wonderful. Sadly,after about an hour or so my father came to take me home while I was still dressed up.In fairness he didn’t comment much about it.He probaly thought it was a childish prank.
My next crossdressing episode was two years later at my house when my parents were out.I finally plucked up the courage to pull out a pair of my mothers tights from her drawer.I didn’t think they would fit me because I was quite short.To my joy they did.I had no idea if her skirts would fit me so instead I wore a pair of my football shorts over the tights.They looked like hot pants.My legs looked great.Eventually,I progressed to wearing mum’s skirts she was a size 14 they fitted me well.From then on I dressed up everytime they went out at the weekend.I felt quite cute but guilt would set in after a while and took off all the stuff and reluctantly turned back into boy mode.I could answer this question a couple of different ways. I was around 11 or 12 the first time that I actually crossdressed. It was a Saturday and I was home alone when I tried on a pair of my mother’s panties, along with her long silky robe, one of her wigs, lipstick and mascara. However, I was much younger when I started thinking about it. This may sound really bad and I hope that I’m not condemned to hell for this, but I attended a Catholic school from Kindergarten thru 12th grade and was an alter boy, from the 2nd grade on. So around the age of 7, I can remember wearing the alter boy outfit for the first time. I noticed how it flowed down to my ankles like a long flowing gown. I would often stand in front of a mirror in my alter boy attire and picture myself wearing a formal gown, feeling like a beautiful princess as I twirled around and around in the mirror.
Ummmm….I was 45 when I first crossdressed(and I’m still 45 lol). I never really thought about it before…
I’ve seen some crossdressers in real life and I just kind of looked at them as I would any woman. I never really thought about being a crossdresser until recently.I think some crossdressers look really hot, and some not so hot. Some, I’ve looked at and not really thought about whether I thought they were sexy or not, but I’ve thought to myself, gee they are really nicely dressed and nicely made up. Right or wrong(probably wrong), I’ve always looked at women, crossdressers, and transgendered people the same way. At least I’m not prejudiced 😉I was about 5 when I used to run around in my mum’s old wedding dress. At first she didn’t mind but as it became more regular she put a stop to it.
T
One time my when I was about 5 my cousin came to stay with us for the night straight from school In the morning I tried on her school uniform. It felt great but less so when she caught me. She told my aunt and next time I was at hers she asked me mockingly if I wanted to play dress up. I was totally humiliated.
I was around 11 when I saw my mom in her underwear in the bathroom when the door was open slightly. I was fascinated by her under garments. I later snuck into her dresser and tried on her nylons and bra. I loved the feeling of my hands gliding over my nylon legs and when I looked in the mirror with the bra on, I found myself wishing I had real breasts to fill the bra cups and experience what being a woman was about.
I was 12 when I first started to crossdress. I was at the next door neighbors and went into the bathroom. Saw my friends moms lingerie hanging to dry. I was mesmerized by her stockings and panties. Once I touched them I was hooked!! I fondled them and finally gathered enough courage to try them on. She was small and thin so they fit me. Stockings, garter, panties and bra! I stood there looking at myself in the mirror and loved how I looked and felt. I ran my hands all over my body. I felt so good!! Needless to say I had an erection! What a great feeling!! I strayed spending more and more time there after that. I even worked up the courage to sneek into her room and take some of her lingerie for my own! I wore them every chance I got until my mom found them in my dresser. Dad laughed and asked who the lucky girl was!! That’s how it all started. So glad I used her bathroom that day😃
Hi Billie-Jo!
Funny, this is just what happened to me! Was at a friends house (a bunch of us) playing around and I had to run in and use the bathroom.
There hanging on the back of the door was a black silk and lace negligee. Don’t know what compelled me, but I stripped naked and put it on! It felt so good! I was 11 or 12, and I’ve been doing it ever since!
I was about nine. I remember accidentally brushing my hand against my teacher’s nylon leg. It was magical! That was a texture I had not experienced before. Even though my mom wore nylons when she went out, I had never touched them. As well, my mom was a plus size woman and I was not interested in her things. On the other hand, my slightly older sister wore some fashionable tights and pantyhose to school everyday, and she was also pretty. She got a lot of attention for her appearance. I wanted to be like her, but not the slob she was. Her bedroom floor was always cluttered with clothes and lingerie. As soon as she got home from school, she just peeled off what she had on and left it laying on the floor. You really could not see the floor except under her bed! I took a chance and ‘borrowed’ a pair of her navy blue tights without her knowledge and later, late at night, I put them on in bed. Oh how good they felt, even a real turn-on! I didn’t want it to end. Every day I would trade what I had with another pair from her floor, no doubt she wasn’t missing them. I couldn’t wait to put them on in bed later on. I was hooked. One time my mom found a pair of tights under my pillow while changing the linen. Instead of scolding me, she told me to put them back where I found them! Shortly after, my sister began complaining that she was missing a pair of tights. Right away my mom asked me if I had them! At the time, I didn’t!
Borrowing my sister’s tights went on for a couple years until she moved out temporarily to live with her boyfriend. But she hadn’t taken her entire wardrobe. My mom put me in her room with ‘strict’ instructions not to touch her things. That’s like putting a brick in the hand of someone in front of a large glass window! How could I resist having all her clothing to myself in a lockable bedroom? The first thing I tried was her red 2-pc bathing suit. Oh how I loved it and wanted to keep it. It fit perfectly, except I had no breasts! I used bunched up nylons in the cups to fill them. Later I wore most of her bras, her skirts, blouses and other lingerie she had, too. I was in CD bliss! I was even able to fit into a pair of her stack heel sandals! It all ended too soon, she got married and took all her clothes with her. She never knew I had worn most of it myself.
In fact before she got married, she bought herself a white satin bustier to wear under her wedding dress. I wore it about a dozen times before she got married in it! Now I love having identical bustiers in memory of that time when I wore hers. Once she had taken her things, I was at a loss, nothing to wear except used tights and pantyhose that my mom collected (for an unknown reason), that had either laddered or snagged. I had only those to enjoy until I got out on my own and to buy things for myself.
I was 5. I tried on my mothers one piece bathing suit and BAM
it was on
It started when I was 10 with my moms and aunts pantyhose and a nightie w/the help of my aunt..when i was in my early teens it progressed into trying on more things and then the make up and wig to finish it all off. I do so love them days and the memories & experiences that came along with the journey. Xoxo
I was four years old the first time I remember crossdressing.
I know this because the ‘pretend’ game I was playing involved me ‘being a good girl and taking my medicine’… Sadly the medicine was not ‘pretend’, it was a liver function suppressant to stop me wetting the bed. I ended up in Intensive care after drinking nearly a pint of it, and I know that was in 1974 as my mum has paperwork relating to it.
Imogen x
I was 12. But, I remember wanting to wear girl clothes a lot earlier than that. When I was around 5-6 I remember swimming with my female cousin. She wore this little cute bikini. I wanted to wear one like hers so bad. Also, My grandmother liked to sew and when I stayed with her as a kid I would go along to the store to buy material and patterns. I loved looking at those huge pattern books with all the pretty dresses. I would just dream and dream of wearing them. When I was around 7-8 I discovered my name was Jessica. My mom started working full time when I was 12, and it was then I was finally alone for a few hours and able to dress.
Jessica
I guess I was about 13, i tried on a pair of my older sisters white lacey panties ( they were incredibly sexy) and it all progressed from there. It really was a moment that I will never forget, and the start of many good times
View all I remember it like it was yesterday I was in the bathroom when I saw a pair of pantyhose sitting there and I put them on and it was electricity ran through my bodycouldn’t stop looking in the mirror and my legs and rubbing my hands up and down sheer nylon feeling after that I was hooked anytime I was alone in my youth I was in my mother’s ClothingI did not know what it meant I was a little embarrassed and ashamed but I couldn’t stop myself I would sit there all day home alone watching The Price is Right Time girls are so feminine and girly but I would try to imitate them and I became very good at mannerisms of a girl well I don’t want to ramble on but that was my early years of crossdressing and I did it all the time and enjoyed every minute of it I wouldn’t take it back for anything in the world I really loved my childhood and I love panties and pantyhose and nightgown anything silky and high heels I could really navigate to floor and some 4 inch pumps well thanks for reading Jasmine
I was about 7. I remember my aunt Sharon babysitting me and while she was napping, I tried on my sister’s dress. I was the only kid of four of us at home for some reason. Sharon caught me in the bathroom and I remember her saying, “Oh how cute! “
Hi Annie, Nice story your lucky to have had such an understanding aunt. My aunt most certainly would not have had that attitude unfortunatley
I was somewhere around 12, and I remember seeing my Mom’s undies in the laundry hamper, as I’d put my things in it too. Then one day I pulled a slip out, and put it on. The feel of the soft silky fabric was amazing, and quickly became quite a turn on. Then I put other things, but my favourite became is what I know now is a corset. I would do this anytime I knew I would be alone in the house for a while.
Don’t ever remember trying on her outer clothes though, only the underwear.
I was caught by my Mom, with her slip on, I think, only once, then again when I didn’t return her corset and she found it in my room. She just laughed it off, and it was no big deal. Don’t know what she’d say if she saw me in full Amy mode now!
Amy
I guess I was probably 8 or so when i took to dressing up myself. My father was a traveling accountant and would be gone from monday till thursday or sometimes friday my entire childhood so most of the time it was just me my mom and my sister. The thing they seemed to enjoy the most was dressing me up. to this day there remains many poloroids of me in pink costume dresses, floppy sun hats and such. I had big brown eyes, long eyelashes and a fairly gender ambiguous haircut (sort of a dorthy hammel/ debbie boone type cut popular in the 70’s) i was always being mistaken for a girl and took great delight in it till my dad finally had enough and made them stop dressing me up (and made me stop kissing my friends) but i always kept those costumes, i hid them at the bottom of my toy chest, under the bed and even in my pillowcase. Any chance i got i took them out and put them on. Later in my teens i started pilfering pantyhose and bras from my mom and sister and would stretch out my sisters dresses, later i would do this to my girlfrinds dresses, then later my wifes till i finally decided, “screw this” and started buying my own. I’m still amazed how long i denied myself the pleasure and relief i get from dressing, how long i denied to myself that it was something i needed and i feel so blessed that i’ve finally discovered and embraced the “Rene” that was in me from the start!
The first time was as an early teen where my cousin dressed me in one of her dresses. I loved it but didn’t let her know! Next it was my mom’s lingerie, bathing suits, dresses, hose, or whatever i got my hands on. Next it was lipstick and trying makeup! Then it turned into girlfriends panties or whatever i could find! No one knew of my desires until my mid twenties when a 45 year old woman seduced me. I had enough trust in her to tell her and she accepted immediately! Nothing beats her dressing me the first time!! It turned intobrole reversal and other fun things! I now do it in secret but would love to share it again!!
I was 24, when I agreed to a Halloween party when my wife said—“let’s dress you as a woman”—-
Two weeks later, I found pink bikini panties/matching bra, mini skirt/top, a legg’s egg, and a medium length brunette wig on the bed , white pumps, and shaving gel and pink razors on my side of the vanity with a note saying “need help-holler”……….never looked back from then on………….it only get’s better…
Mikki.
Don’t remember exactly when, but I know it was before I was seven. Had two older sisters and could not stay out of their clothes. Also wore mom’s and grandma’s clothes. I loved the silk panty’s and slips s they had and the garter belts and nylons. Great memories.
I tried on mom’s panties, bra etc when I was quite young but the first time that I was fully dressed was 17 with the help of a girlfriend.
It’s probably similar for many, experiment with items of clothing mainly knickers then as you get older you can buy your own stuff but more importantly the stuff actually begins to fit. The good old days.
Like many I was around 5 when I first dressed. The knickers and clothing seemed to have a magnetic pull and on they went. From that moment I was hooked and remain so to this day. Great times
I remember having to try on my cousins communion dress so my mom could finish it up properly. I had to stand on our dining room table while she pinned it up for sewing. Felt embarrassed and excited at the same time.
42 im 44 now
My wanted to seperate from me she actually recused me of crossdressing for over 2 years and I wasnt one of the last arguments we had I told her if I was that she was just jealous that I would better than she does and represent a women better I got no response
So I tell my sister and she gave me a pair of jeans and my Journey I’ve trying to prove it begin
Now it’s not even about that more of me growing and being better period although I still have it in my mind
I so want to show her that I can do what I told her
That is the male ego and competitiveness and me on that side of me
Melody side just tells me to move on that will show her more than anything and will eat at her in same process and no effort at all
Melody just wants to be as happy as possible and enjoy as much of life as she can
She is getting me to start thinking the sameway and more positive she has been the thing Ive needed for a good while so they watch over each other
I love having both sides its been a total blessing and glad I have her
I found a pair of my sister’s tights when I was around 11 or 12 and put them on. I remember it like it was yesterday. They’re were a burgundy, lacy style. They didn’t fit very well, but I was hooked! I am now nearing 63 years old and except for a few seasons of trying to quit, I am still dressing regularly. Albeit with a very extensive wardrobe of my own instead of borrowing clothes my SO.
I was about 16, my sister just got a ton of clothes from a girlfriend of mine and since seh wasn’t interested in them I decided to help myself before they were all donated. I mostly stuck to my sisters prom and homecoming dresses until I moved out and bought my own things (which I quickly purged). C’est la vie!
I find it interesting that the majority of us started at a pretty young age. For me, environment had a lot to do with it. With two sisters and a mom to live with, I was often dressed up the same as my sisters when we would play that game. It never seemed weird to me, but it also definitely led to my curiosity about stockings, bras, etc, and I found myself trying these on at a very young age. Later on, it became an urge that I had a hard time overcoming.
I was twelve. My mom was quite old and so some of her underwear was tucked in the back of the drawers as she did not use it anymore. I had felt her nighties and wanted that feeling again, so as I explored the drawers I came across these soft, silky delights. At first I would wear them and get them back as soon as possible. Then it dawned on me that the would not be missed as they were far too small for her. So I started a secret stash that included stockings, a corset and nightie. Hence my love of stockings garter belts etc. Once I out grow them my opportunity to dress disappeared, until later…..
DavinaIt was the dim and distant past of 1980 and I was 14.
When I was around 7, I would wrap an old bed sheet around my naked body like an East Indian sari. Then later I found a box of girls clothes. They were hand-downs from my Aunts girls, hoping mom got her wish that I would be a girl. One fit quite nicely and I pranced around looking at myself in the mirror. I did this secret play several times until I was dressed and fell asleep. When I awoke, there was a blanket over me. Mom had to have been the one because the brothers would have teased, and father would have gone insane. For the next several weeks, mom would smile and I would turn beet red. I would continue secretly raid that box for larger sizes as I grew. Mom never said a word.
Hi Rachel, just to clarify, some of us got into this by fully cross dressing first and others just simply trying on an item of clothing belonging to a sister, mother or whoever. Although the question does not mention both scenarios, you could answer whatever applies to yourself 🙂 .
Fiona xxx
Thanks! The long version… Is a story that I need to probably tell.
The short version. Is 10 (mother’s bra and panties) and 12 (mother’s full outfit) and 36 (full femme, make up and all my stuff).
I may get around to writing my journey, although it may be dull and weird!
X
Hi Rachel, dont think that! we all have our stories to tell however weird you may think they are. Its all part of our journeys, no matter what path you take, we are all different, many of us have our own different circumstances, but we all in the end want to achieve the same objective no matter how we try to do it 🙂
Fiona xxxx
From age 6, I grew up in a woman-free home, and my cousins are all male. The first chance came when I was 14, and visiting my mom for a summer. Tried on one of her dresses when she was out for the afternoon. Caught by my brother, I tried to hide under the bed. About a year later, I found a sun dress someone had abandoned in the school auditorium, and I wore it from time to time until we moved and I lost it. No more, until recently.
I was around 8 or 9 I would try my sisters clothes on. Then when I was 12 my aunt found me wearing her clothes. Took me to the mall and had me try on all kinds of girls clothes. She picked a few outfits out had me wear one out of the store and when went for an early dinner then to a movie. I had long curly hair and the put a little makeup on me everyone thought I was a girl I really enjoyed that day. We would do stuff like that every now and then till I was 16. I dressed a few times in my 20s. A lot in my 30s but it seems in my 40s that’s all I want.
I can’t remember the exact age I first crossdressed, but I was in jr. high. I’d say I was 14 or 15. The few times I was home alone, which wasn’t often, I’d try on my mother’s clothes and even attempted to put on makeup. I looked dreadful but enjoyed it. Then as I got older I tried to ignore the desire to crossdress. Within the past two years, I’ve realized I didn’t’ want to ignore these desires anymore and decided to crossdress again.
I would of been about 5 staying at my cousins house, we would always play dress ups and I loved being the girl, then ewe went overseas so that stopped for a while till I meet some new cousins in Finland, a we couldn’t speak the same language but we could play dress ups again. This was awesome till we set of again. come back to Australia and it all stopped for a few years till i was about 14 and started borrowing my mothers things till i was old enough to buy and purge my own things.
Easy for me to answer – 6 years old and I’ve never looked back. I think we can all identity with the pleasure of dressing en femme. Whether we wish to be regarded as totally feminine and loved as the woman we wished we could be or just live with that desire it’s all okay. Peace and love to all my sisters out there.
Some of my earliest memories were of my mom dressing me up as a little girl. When I started getting upset when she put me back into boy clothes she stopped doing it. She kept the clothes on the top shelf of her closet and I’d sneak in and dress up. She was always angry when she caught. I actually went to kindergarten in panties a few times as my mom was too busy with my newborn brother to see me put them on. I tried to kiss a boy in the 1st grade. My mom was called into school. She threw out the clothes and put me in a different school the following year. I think if I was born today in a more tolerant world I would have transitioned. At least now I get to dress how I want most of the time and kiss boys without anybody calling my mom. Lol
I started around the age of 8 when I tried on my mother’s high heels. Not exactly sure why I was so fascinated by high heels. I only remember that they triggered my feminine journey.
Omg really I started around 12 or 13 would watch mother as she was getting ready to go to work. So one day I said I would love to see how it feels to wear dresses bras panties. So after she left for work one day in summer I got anxious to do it .omg from day one i just knew i wanted to be just like mother and be able to dress like her everyday. I kept doing it for many years .till one day on my 18 birthday i said i have to come out. I did and she was not shocked at all. She said she ALWAYS knew I was going thru her things .so she asked if i was happy of course I said yes .she said good cause shes happy also.she also said I FINALLY have a DAUGHTER. And gave me big hug and said Welcome to womanhood.that was over 30 years ago and I’m still and always will be her DAUGHTER.
Lucky you. Next to dressing, there’s nothing better than having an understanding family.
Bettylou
I was about 5 years old, wearing my little sister’s Sunday School, dress when the babysitter walked in on me. Se didn’t say anything to me and just left the room. Of course, she told my parents and later on they let me know that boys do not wear dresses. In my teens my Mother found my girly undies that I had obtained from the apartment complex laundry room. Both parents took me on about the stash. I lied and said I’d bought the items myself and only put them on once in a while – another lie. Joined the Navy at 17 and didn’t dress again until a year later on a port call at Hong Kong. I spent a couple days holed up in my hotel room, wearing the nice lingerie and dress I bought in town. I slept in a very girly night gown. Room service took care of my other needs. I was in heaven. From that point on, I usually had a stash of ladies undies, clothing and makeup. Even after getting married, “Kathy” continued to visit and allow me to feel like I was in heaven, again.
Now, 45 years into my 2nd marriage, my bride knows about “Kathy”. Thanks to counseling, we have come to the point where she lets me put “Kathy’s” things in the laundry. She does not wish to see me dressed, but does accept underdressing, “below the waist, only”. I am, once again, in heaven.
I was 4 when I first wore pantyhose and pumps with a shirt that looked like a short dress. I was 17 when I first wore pantyhose out with shorts. I was still 17 when I ore pantyhose out with short girl’s shorts and platform wedges. I was 18 when I first dressed fully fem and went out dressed like that.
I was “out” my first time dressed! Looking back, it was kind of funny. I think I was 6 or 7 and had joined the Cub Scouts. For those who don’t know, that’s the starting point before being old enough to join the Boy Scouts. Anyway, there were eight boys in my pack, and the den mother had us working on some cultural stuff. She decided we should do a Mexican Hat Dance for the PTA. So of course some of had to be the girls for the dance. I had to groan and pretend that I didn’t want to do it, but seeing the white dress with the boat neckline and the multi-colored horizontal stripes had me so excited I could hardly pretend. We did end up wearing the dresses over our uniforms but that didn’t matter to me. Swirling my skirt, curtsying to my partner, all of that lit a fire in me that endures to this day. And I still remember how many moms came up to me afterward to say what a cute girl I made. I had no idea how to respond, but what a sweet memory to carry.
The very first time I can remember wearing a piece of female clothing was at age 6 or 7 when I had run out of umderwear and sis told me I would need to wear a pair of her knickers which I did for an hour or so and I hated them!!! I made a massive fuss about having to wear girls knickers – how things have changed.
The first time I wore an Item of female clothing and liked it was when I was 11 or 12. I was home alone and one of sisters skirts was freshly washed and waiting for her to put it away. I remember wondering what it would feel like to wear. Amazing was the answer to that and I’ve been hooked on dressing ’em femme’ ever since.
Take care girls.
Anne-Marie.
I started cross dressing around 12 or 13 I would watch mother as she was getting ready to go to work. So one day I said I would love to see how it feels to wear her dresses, bras, panties, slip, girdle and nylon stockings . So after she left I went to her dresser and found her lingerie and foundation wear.
OMG! An incredible feeling overcame me. It was thrilling. I thought to myself, boys don’t do this and had to carefully return everything. That didn’t last long as I just had to dress again.
So many CDH’ers remember the incredible feeling of lingerie that it makes me wonder whether a line of “men’s” wear modeled on lingerie would be marketable. I realize there are online outlets that sell bras and panties for men, but I’m thinking of underwear not made to appear “girly” so as to appeal to a broader customer base.
Hi Kimmie,
I’ve seen advertisements from several companies that sell lingerie for men that are designed and manufactured for the male physique. The lingerie has the styling and look of women’s lingerie. Soft fabrics and pastel colors with pattern designs are used. They’re still in business after a few years so seems there is a market with demand
Alice
I started 11 months ago at the age of 59. I had a fluke opportunity to try on a pair of black Stiletto ankle boots. Now I have a collection of footwear, a wardrobe of outer and under garments and a variety of jewelry. I’m of a mind set that as I come to become more aware and knowledgeable, it is my hope to begin to purchase quality items. Rather than spending top dollar on things That “ look cute but don’t wear well”
Wow. I’m not t trying to pry, but I am curious. Did you not have any inkling that you desired to try wear the boots? Do you have any idea what may have brought the desire after so many years?
Hi Doll; When I was younger my sights were set on having and knowing as many of the Ladies that would have me. Married over 20 years. Not enticed to wonder as I did enough of the sampling in my younger days. The fluke opportunity with the ankle boots was I was working late night doing repairs in a 2nd hand store when I took a brake … I happen to catch sight of those Stiletto heels and became intrigued by the shape of the and the arch the shoe. I was compelled to try it on. I actually didn’t think it would fit … but I took off my work boot and heavy sock and tried it anyway .. Oh My! When my foot slid into place .. I had to pause … the tried the other on Whew, it was as if someone with strong, soft and cool to the touch hands had taken hold of my feet. There is so much more to share about how this lead and built up to me becoming a Dresser.
In my late teens something “strange” came o er me and made me look in my mom’s drawer..where I found a longline bra and a long zipper girdle…ofcourse I tried it on and a strange feeling of heat and joy came over me…suppose it was initially a more sexual inspiration. Then advances with mom’s underwear and sisters tight trousers…all lasted for a couple of years. Then in my mid 30’s and being married we went to a fancy dress party where wifes were supposed to dress in husbands clothes and the men in their wifes…My wife even did my make-up and as I felt great that evening started to dress again for a couple of years corresponding to my ” mid life crisis as the dressing de-stressed me and made me feel good in my wife’s clothes. Then another long period without dressing until my early 50’s and have not stopped since. Enjoy dressing, but in a different way as about ten years ago asked the question if I could “pass” and ventured into make-up. After a few makeover of which was super took the courage to go out in public and have never regretted it since. Now doing all my shopping as “Helene” and try on in the ladies fitting room, wining and dining which is very relaxing and enjoyable .
Now past my 70’s have no intention to stop and my female wardrobe just increase each year!
I remember when I was young asking my father for a Barbie doll because I only had GI Joe’s and the like and figured they needed a damsel in distress. My dad told me in no uncertain terms that me playing with “girl” things wasn’t ok. My sister gave an explanation to him but he didn’t want to hear it; he’d rather my big muscly men rescue other muscly men, which is pretty gay if you ask me.
For years I was sensitive and insecure about my masculinity and would do anything to prove how manly I was. I would fail to make the sports teams and had few friends. When I entered college, I met my gf Leah who is in to theater and I would help her prepare the shows, arranging sets and wardrobe ect.
I was intrigued by the dresses at the theater, but didn’t realize it then. One night 2 months ago, while visiting Leah, I was up after she went to bed unable to sleep. I noticed her makeup bag and felt compelled to try it on; I have no idea why. I had never worn makeup or women’s clothes before except for a joke, but something changed as I put on the lipstick and blush.
I was 20 when I CD for the first time and i cannot describe the sensation I felt while i put it on, but it was heavenly and euphoric. I realized that I had found a way of expressing myself I thought only existed in the minds of perverts or the disturbed. I quickly changed my opinion, as I was crossdressing and I wasn’t a perv. Leah saw me at some point without me noticing before going back to bed. She cut me off without explanation for a week before telling me what she saw and that she was willing to make things work.
The first article of clothing i bought was a pair on pantyhose and the feel of them on my legs was divine! I got a pair of black heels and a red shirt to go with them as well as my own makeup. I am overwhelmed by this wonderful form of expression and while I am still figuring out my own gender identity and sexual orientation, CD certainly helps me cope with the trials of life and I couldn’t ask for anything better!
It never ceases to amazing me how gay “straight” men are most of the time. Any time I’m somewhere with a TV showing football talk I just wonder if that whole sport was created for guys to oogle each other. Yeah, I’ll pass!
AAAnd they have names for their positions like ‘tight end’ and ‘rear defense’…lol. Personally, I hate American football. The players are nothing more than overpaid entertainment chasing a piece of leather in my opinion. Is it a tough game? Yep, played it in high school but certainly don’t think it’s something to make a career out of. Doctors that create cures, scientists that propel humanity to a new level of excellence, engineers that create solutions to solve the world’s problems…these are the people that should be paid the big bucks. Morons that chase leather and then try to tell the rest of us ‘normal’ people what to believe can f*ck off.
Okay, a bit more of a rant than I had originally intended.
If I can attempt to add a “bit of levity” to this topic…
As a “true Blue Aussie” who grew up with Australian Rules, (aka”the footy”). I could never understand hide nor hair of the gridiron games rules.
Three years ago I visited family in the US and saw my grandson play a high school gridiron game.
The only thing I understood about the whole event was that seniors got into the game for nothing!!!
….Oh, there were also so many “stops and starts”. By contrast Aussie rules hardly ever stops.
But then equally, back in my business days I entertained US visitors to “our great game” and they were just as befuddled by the rules of our code….
So I think that at l;east for me, I’ll go back to thinking about lovely lingerie and not how the stars of either code “play or get paid”.
Caty
While I’m pretty sure I dressed at 5-ish as remember very vividly hiding at school in a wendy house having put on a dress and somehow had got hold of a lipstick. I sat in there for what felt like a long time giggling to myself. I don’t really count it as me actually dressing in the same sense as what I do now. That I think probably started when I was probably 10 or 11 as I remember mixing my mother’s clothes with my school clothes in an attempt to get a version of the girl’s school uniform.
Hi Girls. In another forum I explained that when I was 7 my sister convinced me to play dress up. She dressed me in a floral dress with makes up and taught me to be a lady.
Then after that I never ceased and did CD on a regular basis and still do.
One
if my fondness memories when I went all out for the first alone. I put on my mothers bra and panties and sat at her vanity and did my make up. Put on some panties hose and then earrings and rings. I slipped into my mothers wedding dress and veil and I danced and spun. Then I sat real pretty and admired myself in the mirror. I’ve never forgot how pretty I felt that day and I wore that gown many more times after that until I out grew it. Loved every minute of it.
Thanks for listening girls.
Hugs and kisses
Rosiebeth.
I was 8 or 9 years old. I was visiting my grand aunt and I found three pairs of nylon panties and a sheer short red skirt( I think it was a bikini cover-up) in a dresser drawer in her spare bedroom. I asked if I could try them on, I was hooked. Not long after that, I asked if I could see more of her clothes. She allowed me to pick through her panties, slips, and dresses and we put them in a box that we placed under her bed. Whenever I’d spend the night, we would play “dress-up”. This continued until she passed away in 1983, I was 10 and a half.
As I posted elsewhere, I was about 4 or 5. I remember one warm afternoon asking my mother to make me a dress. She did out of kraft paper (you know, that light brown heavier than typing paper on rolls), and I’m guessing scotch tape, and it was a full dress. I very vividly remember standing in the front room as she was making it, and again wearing it outside in our side yard until it tore. I have no memories of actual thoughts of that time (it would be amazing if I did), but two ideas come to mind as to why I asked, but only very slightly possibly co-equal. I would guess a ‘trained’ psychiatrist would say differently, but he/she really would never know the real me. Anyway, I truly suspect I had transgender thoughts before that and it just finally surfaced at that time, and being that young I was way to naïve to realize I should keep quiet about it. The psychiatrist version would be that because my father (I was one of 3 young children) had tragically died in an accident within the previous year , that I was ‘acting’ out, you know, not wanting to be a male. I suspect that’s how my mother viewed it, and was trying to ‘console’ me. However, for the past x number of years, I would say it’s a 99.99999% likelihood that I don’t buy that clinical explanation. (and Blanchard wouldn’t buy mine, either, so, eh)
IIRC, 10ish. I tried on a pair of my moms used pantyhose. It wasn’t a sexual feeling but I loved how they felt. I used to stash them in the back of a closet. My mom finally found them and confronted me about it. I admitted to wearing them and she was fine with it. I told her it made me feel close to women and she was fine with that.
As is usual with me, even simple questions have complex answers.
My desire to wear something silky goes back to my earliest memories probably around age 2. When my mom’s skirt would brush against my legs it would send a tingly feeling up my leg. I always wondered, if just a few seconds did that to me, how do girls wear it all the time and what would it feel like to be surrounded by such silky clothes. Even when the dresses weren’t silky on the outside, they would wear a silky slip underneath.
My sister had a yellow nylon dress that she would wear for birthday parties. My mom used to hand wash it and hang it to dry on the shower curtain rod. Whenever that would happen I would make sure to use that bathroom (the other was a half-bathroom with no shower or tub). After doing my business I would stand precariously on the edge of the tub and reach up into the dress as if I were putting it on (often slipping off my shirt to feel the dress on my skin). I never got it much past my waist, but the feeling gave me shivers (remember I’m standing on the edge of the tub).
Around age 9, there was a performance at school where the boys had to wear tights. My mom gave me a pair of tights from my sister. One day we had a dress rehearsal towards the end of the day at school. I wore the tights under my pants all day and loved the feeling, rubbing my hands on my legs discretely when I could. I remember it feeling a bit cold when we had to take off our pants and wear only the tights. I don’t really remember the day of the performance, but I suspect it was similar, except that we all took off the tights afterwards in the bathroom (it was a morning performance).
I was 12 when I was sick one day and had to stay home from school. Having an older sister and two younger brothers, I rarely had time on my own. In the early afternoon my mom needed to get a few items from the supermarket and left me alone at home for the first time. I was starting to feel better by this time. At the time a friend had given some clothes that no longer fit her daughter to my mom. The ones that didn’t fit my sister (or she didn’t want, I’m not sure which) were in a box in the living room. So while my mom was out I tried on a faux leather jumper. That was the first time I wore a dress.
Hiya, I was around 7 years old at Primary school and they had a dressing up box so you can guess where I am going. The first stirrings occurred then and have progressed over the years with constant purging and marriage restraining me. We are lucky times are changing now with online shopping a god’s end to us all. I hardly have any male clothes now and a lot of my female tops and jeans can be worn in male mode. That said you cannot beat a sexy short dress and stockings with heels lol.
Sandra,
It’s much the same for me. I’ve been cleaning out the closet, and all of my guy shirts are unisex and my guy trousers are really Gloria Vanderbilt or women’s Lee Riders. You can’t really see the difference between my side of the closet and my wife’s.
Hard to say an age. I was elementary school when I first began to sneak a pair of pantyhose or heels from the closet. Wouldn’t really consider that dressing. Then in the 5th grade we had a “mis-fit contest” as a fund raiser. All the boys that wanted to participate dressed up as a famous female. I was all in, super excited and I was Farrah Fawcete. I remember arguing with Mom because she had a skirt I could wear but no top. she was just gonna put a T shirt on me, I wouldnt have it. I had to go all out. She finally ending up getting a halter top and a pair of High Heels from my Aunt. it was amazing. I ended up in the halter, a mini skirt, tan pantyhose, brown high heels, and a blonde wig. But that was the end of serious cross dressing and it was back to sneaking a piece of clothing or a pair of shoes until my early 20s. After I was married the first time, my wife worked nights and I took that opportunity to raid her closet most nights. I would put on her dresses/skirts, pantyhose, heels. I would clean teh house in them, cook in them, then sit and watch TV until time for her to get off work, then I would go change. She never knew. I opened up to my current my wife as soon as we started dating. Not only was she supportive, but she is the biggest reason i have a very large wardrobe of my own now.
Chelly
18. I had a few intense sexy experiences (alone). I definitely looked up content when the Internet came into my home (late 20’s) and didn’t buy anything until I was 33. I am 51 today and very comfortable with it. Still closeted, but not afraid if the idea came out. My wife knows, but avoids it other than in counseling sessions. I now understand why it gets easier as you get older- money gets easier! (LOL) Recently, I have had a few experiences being dressed outside of the house.
its all true…i didnt care about the sex end of it…just the personal pleasure of it…,always thought girls were so lucky to be able to wear the softest clothing with a sea of color to choose from ….when i see a girl /woman wearing something alluring i wonder what it would feel like to wear the same gown, bra, makeup etc…
I AGREE….SEX WAS NOT AN ISSUE…SENSUALITY WAS….FINDING MY FEM INSIDE ME…I KNEW I LOOKED AT THINGS DIFFERENTLY THAN THE GUYS …ALWAYS ADMIRED GIRLS AND THEIR CLOTHES…NEVER FIGURING OUT EVERYTHING AS TO WHY ….I LOVE GOD AND I DONT HIDE FROM HIM…I HAVE TRIED TO STOP MANY TIMES…PURGING MY STASH MANY TIMES…ALWAYS COMING BACK TO THAT AMAZING FEELING OF SILK DRAPING MY BODY…LACE BRUSHING MY THIGHS…BRAS CONTROLLING MY MAN BOOBS…AND MOST OF MASTURBATION WITH THE SLIPS AND PANTIES…GREATEST ORGASMS I HAVE EVER HAD…NOT UNDERSTANDING WHY WOMEN WEAR WHITE COTTON PANTIES AND BRAS WHEN THERE IS A SEA OF COLOR AND DIVERSITY OF MATERIALS IN THE LINGERIE DEPTS …I HAVE EMPATHY FOR THOSE WOMEN WHO ARENT SENSUAL IN THEIR DRESSING….ROARING TWENTIES SAYS IT ALL…WOMEN WERE FANTASTIC IN SATINS AND SILKS…NIGHT GOWNS…WOW…I LOVE WATCHING THOSE MOVIES…RARE TO SEE A WOMAN IN PANTS SWEATS JEANS…WOMEN CAN WEAR WHAT THEY WANT…AND TODAY THEY DO…BUT I HAVE TROUBLE FIGURING OUT WHY WOMEN CANT FIND THE RIGHT BRA SIZE (70%) OR THE RIGHT PAD SIZE (70%) AS THE TV ADS TELL US…IF I WERE A WOMAN I WOULD BE AN INDIANA JONES OF APPAREL HUNTING LINGERIE DEPTS FOR THE RIGHT SIZES AND MOST COMFORTABLE MATERIELS..LET ALONE ALL THOSE COLORS…YOU HAVE THE ARK OF THE COVENANT ..GIVE ME THE ARK OF LINGERIE DEPTS….SO BE IT…ENJOY WHATEVER YOU WEAR I GUESS…JUST MAYBE YOURE MISSING OUT ON TRUE FEMININTY…YOU THINK
There was nothing sexual about it for me. I was jealous of the girls! The boys were all a bunch of clowns, and I related so much better to the girls in school! I wanted to curl my bangs. I wanted a perm in the worst way. If I was left alone, I was into my mom’s makeup and underwear drawers! I loved the feeling of nylons! My mom would bring me askin to go shopping for my cousin, because we were the same age and size. I would orp up a fuss, but Mom always had me try her clothes on before she’s buy anything. It was a dream! Mom had no idea!
The first time I got busted was actually at school! I was wearing clear fingernail polish. I thought nobody would notice. One of the girls spotted it right away, and made a scene. I just denied the whole thing. And then I hid my hands under the desk the rest of the day picking at my nails…
So true Fiona.
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