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Hi girls,
I have been on the site for a few days and had the opportunity to talk with some lovely girls and read a lot of stuff on the forums which was really enlightening and relaxing because we don’t get this opportunity anywhere else.
So I thought to ask a question myself and I would like to know how did you started crossdressing. I guess most of us had the interest in our minds and started with mum’s or sister’s stuff and never looked back since. I started with my mum’s stuff as a young child which I found really exciting back then ( I still do but not the same intensity i guess).
I have added a poll as well.
Mine was for Halloween with the full dress heels makeup wig and even shave legs have to have the smooth legs and haven’t looked back since
hugs kim🦄
It’s difficult to believe, but 51 years ago, something drew me to look and rummage through mom’s lingerie drawers. Home alone, possibly a bit bored, I wanted to see what I looked like if I were a girl. Got panties on with no problem, bra(which was way too big) awkwardly on, and finally, some lipstick. What I saw in the mirror was transformative. I was pretty. What was actually in the mirror may not have been that pretty. But, it was a magical experience, and I haven’t stopped since.
Kay👩🏻🦳👄
Hello Jenny, Yes like most of us girls it started with mums clothes [had no sisters] then when I started work I could buy my own clothes. It was better to be able to choose what clothes you wanted then borrowing you mums. I did wear some of my cousins clothes when I was a teen, but only for a little time. love Helenmarie
There is no poll answer for me here, I was a late starter. I was in my 50s and loved wearing thongs. My late wife actually liked me wearing thongs. Anyway, as they were wearing out, I needed to get more but the only ones available to me were so awful looking, mostly black with beer ads or football (soccer) teams on them that I got a bit disheartened over finding any nice looking ones. Of course, the womens racks were full of beautiful thongs & strings, so I asked wifey if she minded me trying a womens thong. That was the start of my dressing and, 20 years later, I rarely wear “mens” clothes.
Interesting…..
Older sister’s for me as well. Saw some baby blue nylon panties she had left in our shared bathroom and had an incredible urge to try them on. Sliding then up my legs and into place was indescribably exciting. I knew then that this was not just going to be a one-time experiment. From then on, I borrowed her panties, bras, nylons, and baby doll nighties when ever I had the house to myself. It felt so thrilling in those articles of clothing. Once old enough, I started purchasing my own as I know it was not right borrowing her things without her permission.
It is true Emily that it would be better to ask but a little awkward to ask your teen sister if you can borrow her panties. At first it was a bit of a thrill in addition to other feelings knowing you were wearing panties that had been on a gg.
Hi Jeannie – Yes, the thrill was what kept me coming back time and again. My sister and I were pretty close (at least as close as an eleven year old boy and a 13 year old girl can be). If I could have gotten passed the embarrassment of asking, I actually think she would have been accepting of it and given me a few pairs of her older panties to wear so I would not need to borrow the ones she was actively wearing.
Hi Jenni
Oh yes, definitely mums clothes….I was never caught, but did she know???.
I guard and look after my clothes so jealously, the more I think of it the more I am sure she must have guessed a clumsy urchin had been into her things…..but she never mentioned it!!!
Huggs, grace xx
Ahhh I guess I have to mention that growing up, I had a strong body odour, so it was pretty obvious when I dress up in borrowed cloth. I don’t know why my sister never directly confronted me, when I’ve got warned by my parents a few times. I tried hard to mask my smell afterwards, and I don’t get warned later on… but I do wonder if it’s because they kinda give up on telling me to stop, ahah.
I checked “someone introduced me to it”, but a more accurate response would be that I just had the urge. The family split when I was 6; I went with my dad, and grew up with no female relatives, not even a cousin. Most of my playmates were girls, and when I was 9 or 10, two of them, twin girls, put in one of their dresses a few times. It was just a game, and I don’t recall being impressed. When I was 14 or 15, I found this old dress in Drama class storage, took it home, and began wearing it after school. I stopped after graduating from high school, but I count that as the real beginning of my CD adventure.
Bettylou
When I was about 5 years old I was enamored of my younger sister’s Sunday school dresses. I snagged one out of the closet one day, put it on and had a nice time wearing it around my bedroom, that is, until the babysitter barged into the room and I was busted. She was very kind and did not freak out. She asked me to hang the dress up when I was finished with it. Of course she snitched me off to my parents.
That evening, when my parents came home they had a sit-down with the young me and explained that boys should not wear girls clothes, and that I should not wear my sisters things. I felt ashamed for what I had done and that I had disappointed my folks.
Fast forward to my early teens. I began feeling the desire to wear girls clothes, in a big way. I managed to acquire some panties and petti-pants and began wearing them under my pants and shorts. By the time I was 16, I had a nice stash of girls clothes and would try things on anytime I was left alone at home.
At 17 I joined the Navy (to avoid the Vietnam era draft) and put aside my crossdressing desires. That is, until a port call in Hong Kong where I stayed at the Hong Kong Hilton for a few days. I bought undies, a slip and dress and nightie and spent more time in my room, dressed, then out and about in town.
All of this left a huge impression on my later years, as I now underdress daily and fully dress with wig and make-up several times a week – at home only. I have embraced the need to feel and express my feminine side as well as my male side – husband, father, grandfather, retired LE. I guess I am blessed, twice times.
o
Isn’t it interesting that a lot of us ‘felt the need’ as it were. I often think back to the days when I would try on my sisters or mothers clothes. I would love to be dressed up by them for fun. Some of the time I would feign a protest and others just go with it. I never stopped there and dressed in secret.
My reasoning was that their clothes were so much nicer than what I wore and I wanted to wear them as much as possible. Was I girl trapped inside a boys body?
Then came that transition. It wasn’t just a dress but I needed to wear everything. At puberty it was a bra, padding and makeup when I could. I didn’t feel like a girl but sure as heck wanted to look like one! Was it a hobby where you wanted to be as good as you could? Of course it was an unusual hobby but, as in a lot of cases with hobbies, it becomes all consuming. A lot of partners accept hobbies but do not want any part of them. You do it fine but don’t ask me to get involved.
My hobby has become a big part of my life now.
Question is, does that make me Transgender as I need to present as female or a hobbiest taking it to the limit?
In my teens I was the same height and waist size as an older female cousin and my mom wanted to make a skirt for her . Naturally mom and her friend had me try it on for them while that checked for fit and made adjustments. The skirt was a birthday gift so they did not want my cousin to be the model. Looking back I wonder what they thought of my lack of protest. I wish they would have had me wear panties under it😊
Started wearing tights at young age. Just Started adding various items of clothing of my mother’s then playing about with makeup. Looking back now I realise she knew what was what but never openly mentioned it. Think she would have been OK if had told her.
Hi Jenni, None of the above box needed. I didn’t have a sister and no way I’d snoop around my Mom’s stuff. No internet 50 years ago so I didn’t read about it. No opportunistic events nor anyone introducing it to me. I think I saw a very passable crossdresser on TV which raised my interest in my teen years. Then my first wife mentioned it to me as an idea which with hindsight I now very much regret turning down. As my hair grew longer back in the late 60s & early 70s, I started being mistaken for female (while still dressed in drab). That also added to the mystique of crossdressing. Eventually the urge just grew too strong to ignore it. It was always meant to be, as my Mom would have said (she always wanted a daughter). Thanks for the topic. All the Best, Hugs, Krista.
Oh my, where do I even start ?? I can’t really nail it down to one event, but a culmination of multiple events :
– when I was small, my mom would wash and hang her panties on a rack in the bathroom. Everytime I had to go to the bathroom, I would look at it and one day I reached out and touched it. I was amazed at how soft and smooth the fabric felt, compared to the tighty whities I was wearing. I was a latch key kid, so I had like about an hour or so after school before one of my parents came home. One day after school, curiousity got the best of me and I decided to try it on. Oh wow ! It felt so nice, so I wound up sitting in front of the TV in my mom’s panties.
– in a school play, I played one of santa’s elves. The teacher said we had to wear leotards. Being small, I had no idea what leotards were. Then a girl classmate piped up and said she would lend us her leotards to wear. I remember wearing them, did the play, and then afterwards hurrying back to the classroom to change back.
– in kindergarten, our whole class went to the local swimming pool. I didn’t have a swimsuit, but at that time the pool had loaners. They ran out of boys’ suits, so they gave me a girl’s suit (it was a light blue one piece). I wore it, and didn’t even dawn onto me that I was wearing a girl’s swimsuit. No one said anything either. It would explain why I have a huge collection of women’s one piece swimsuits today.
This is my start, but I can’t say one event started my journey towards CDing.
I chose going through my moms things. I can remember desires though, even before that. Back at the age of wearing footie pajamas, I remember wishing that they didn’t have the rubber soles at the bottoms and instead were like stockings that formed to my feet. Where the heck did that even come from? And ballerinas…I always wanted to dress like a ballerina for some reason ☺️
I guess mine was opportunistic but not really as you described.
The trigger was the breakdown of my marriage. Nothing to do with cross dressing, never did it during the marriage.
But I now realise it was something I always subconsciously suppressed, was always who I was supposed to be, son, brother, husband, father, always dressing how I was supposed to dress to blend in, be one of the crowd, to conform.
Then suddenly I was on my own. My true self gradually surfaced, and how wonderful it felt. Not to feel I had to be this ‘stereotype’ 100% of the time.
My true self has blossomed, never been happier. In fact I don’t know if I could ever bury this part of me again for the sake of being accepted dating women.
❤️Bianca
Bianca i know it exactly what you mean in your comments. Ive had the same kinda pressure put on myself and its not good. I found your story very compelling and can relate to it totally as been thru similar hugs 🤗❤💖
My dressing started when I first found those Avon lipstick samples that mother used to get with her make up orders. She never used them, and one day when helping her clean some in my parents room, she handed me a bag of them and told me to throw them out. I had always admired how pretty a woman’s lips were when wearing lipstick, so I don’t know what came over me at that time, but I kept them and hid them in my room which was in the basement of our home and private from all the other rooms. I would try each color and see how it looked, making kissing faces at the mirror in my room to see how good it looked. I found that I preferred the pink shades or the deep dark reds.
From there it was raiding the clean laundry for my mother’s bras, panties, and pantyhose finally working my way up to dresses and shoes. Back then mom had beautiful brunette hair so there were no wigs to try, so I had to work with barrettes, hair clips, and headbands. It wasn’t unusual back then to be left home alone or just to spend a lot of time in my room alone, so I had plenty of time to dress and try different lipsticks. It wasn’t until much later on that I tried to wear other forms of make up, and I have never been able to get that good at applying it even to this day.
I didn’t vote as there were no options for why I started crossdressing. After suffering an couple of accidents and losing much of what made me male… on reflection I discovered a feminine anima that began to substitute for the various holes these accidents have left. The crossdressing was, at start, an expression of a change. It became more of a translation of my troubles before becoming a realisation that I had a feminine persona waiting in the wings all along!
I am now on the path to full feminisation and that makes for on very happy woman!Love Polly
I started as most of us girls have done wearing my mum’s ,sister’s ,girl’s next door ,landlady’s (when at college ) only trying on their panties , girdles and stockings .not interested in bras . got married when I was 27 started with my wife’s pantyhose and then took the plunge and started buying my own, at first no bras since then I have been buying and wearing female clothing all my life ,only as a secret closet dresser ,this last two years as an underdresser and guess what most important items are my bras ,all colours and styles with forms, mostly without ,can now nearly fill a B cup .looking back to my early dressing and thinking why didn’t are try on their bras as well ,never mind making up for it now .Heaven .
Michelle xx
My crossdressing is mainly down to black tights as when i was younger id kid myself that i was wearing them to keep warm as id wear them to work under my overalls in the winter as used to be cold🥶 but i was kidding myself as would wear them all the time
How i started? Umm well i was just so fascinated by tights and lingerie when i was around 7,8 years old so around that age id wear my grandmothers old corsets and Victorian style lingerie and it just really grew from there? When my grandma died i made a point of going thru her clothes and keeping what i liked and enjoyed wearing. Although my grandmother died she knew i was dressing as a woman as she would wash lingerie and tights and place them back where id hidden them, also i was in awe of lingerie departments in shops as it was kinda forbidden zone that blokes dont enter? I was fascinated by all the beautiful colours of tights stockings, dresses and anything else that took my fancy. This was the 1980s so a bloke wearing eye liner was very common, also i think id crossdress to rebel and say to myself im breaking the norms! And my crossdressing just stemed from there had a period in the 90s where i stopped as think everyone has a purge and god i regret those purges as the beautiful lingerie and heels and many other things i threw Away! But thesedays since 2015 ive come to terms with it and believe im getting somewhere as its becoming fun again and buying so many beautiful items and really hooked on heels pvc latex in fact anything thats beautiful 😍 i adore. I believe its a long road and it takes time but you have to truly be happy to do what we do and never been happier 💗 hugs 🤗
Being honest to yourself is the best thing as for many years i hid my femme side away and if you have done that you will know that it eats away at you everyday and in the end the urge to be more femme has to have a outlet! I purged but found it doesn’t work and if you have this feeling inside like we all do its gotta be allowed to come out as i kidded myself for many years that ‘ im not a crossdresser’ but in time you have to be true to yourself or it will consume you and thats a very dark place i wouldn’t wish on my worst enemies. So i found that by letting my femme side out everyweek or sometimes more im happy, unsure what all this means in context of my whole life? But im happy 😊
Lovely story Krissy….
Awww shucks thanks jenni, just glad i managed to get it all off my chest and remember all of the facts from what seems a lifetime away 1970,80s was a long time ago hugs 🤗❤
Thank jenni xxx
I had 3 older brothers but no sisters. I remembered spotting my moms one piece bathing suit hanging up to dry in our only bathroom. I was curious as to how it felt to the touch. Next thing i knew , i had it on. I remember how fantastic it felt to wear it. I was just amazed at how my boy parts disappeared and i seemed to have girl parts. I looked in the mirror and saw a girl looking back at me. Ive never been the same since.
Tried on my sister’s nylons and stockings as a very young teen. Not only did I love the feel and thrill of it, I would also read her Cosmo mags on how to be more like a girl, mainly to attract men. In my mind, wearing nylons would somehow make me more desirable to men and as a boy, I very much wanted men to notice me. Still do! 😉
When I was a boy, my mum stored her spare/old dresses and coats in my trunk. I was particularly fascinated by her fake fur coats. So I could not resist trying them on myself. To complete the look I tried one of her old skirts and without access to a bra filled my pullover with tennis balls to give me kind of female shape. And finally her boots with heels to walk in. Always a great experience.
Mel
I used to share a bedroom and bed with my sister from about 3 yrs old until age 6 or so. I found a pink satin pair of her panties and tried them on and was hooked. I would later try on their pantyhose or bath suits. I borrowed my first pink front hook bra at age 13. I now have fully stocked lingerie and clothes drawers that are over packed !
I really don’t know what drove me into wanting to do it, but my first time actually doing it was at a very young age while playing in the laundry room and jumping into the big pile of clothes that were waiting to be put into the washer machine…..my older sister’s swimsuit was in that pile and I saw that as an opportunity. It fit really well and I have been hooked ever since.
What a relief to hear how common this is! And what a great thread.
My story began before I can remember (pre-5). My aunt let me play with her makeup and clothing. I also was fortunate to have a sister (like a 2nd Mom to me) who was older enough and had a great wardrobe to ‘borrow’ from. Mom’s shoes, then my sisters shoes/clothing. That actively started me down this road – in single digits.
Many times have I tried to “detour” down another path to no avail…I ended up back on this two-lane highway of life with one foot in a man’s lane going backwards and one heel in a woman’s lane going forward. The “pull” is the key…
I would work to suppress it, hide it, deny it, etc. I bought and purged many times. I have gotten rid of some expensive hair pieces (what an idiot I was – I can’t find that one anymore). I could have fed a small nation on the amount to money I spent on 2nd self and proceeded to purge months later.
I wish I had accepted myself for who I am a lot sooner than I did. I could have avoided this needless cycle of spend and purge. I could well have avoided the inherit depression that comes with the internal conflict I (we) suffer for this gift (and I do consider it a gift). It’s a rare gift to be able to feel/be both sides.
The challenge now – keep feet in both lanes? The ‘pull’ to be a woman is so strong that it is difficult to describe in words – best word I can find in ‘alignment’…but that barely begins to describe it. I can very easily see myself only in that lane…I can envision taking that major, marriage-wrecking step and not looking back. It is a scary prospect.
Things to think about.
Dani
I remember taking my mom’s bra and stockings at and early age, maybe five years old and trying to dress up. I sure did not understand what was going on, but I remember the feelings, the endorphins running through my body. I was too young then, and probably still don’t understand it today, but I knew I liked it!
I remember the chorus line dancers on TV and wanted to mimic them.
For me it was the dress up trunk that all the costumes were stored in. We would often have friends over and they were almost always girls. So the dress up trunk was often quite well used. Never could figure out the men’s costumes but the ladies were easier to wear and I had a dark blue fancy dress I loved but haven’t been able to wear for a long time. I think if it there were more guys then girls I might ended up different.
I just had a fascination with women’s clothes. I loved dhow they looked and wanted to wear what they wore and look like them. at 4, I began wearing stockings, pantyhose, heels and bra with a shirt that looked like a short dress. I wanted all my own clothes but they were not available to me at the time.
I outgrew the shoes around 11. Then I outgrew the pantyhose and bras around 13. I began buying my own pantyhose and bras. I wanted shoes too, but they would be hard to hide. I finally got my first heels at 17. A pair of platform wedges. Then with some short shorts and a wig, I began trying to look like Daisy Duke and going out in that attire. Very silly, very crazy, very scary but I loved the excitement thrill and rush of it, especially when shopping for and buying pantyhose.
When I was 13 in 1961 watching my mum put on her corsellettes and girdles and fastening her nylons with the clasps on her suspenders, I would put them in when she was out, magical
You forgot to list the wife! I started the day after her funeral. I was sorting and boxing her clothes and when I got to one dress that she always looked stunning in, I walked to the mirror and held it up in front of me. Thinking that I would look good in it, I had to try it on. She would wear my clothes when she had a dirty job to do and if painting so I figured I could squeeze into her clothes. Plus her being tall helped too, she was just under 6’1 and I’m 6’3. After putting on the dress and seeing myself in the mirror with an erection straining against the fabric I dumped out All the boxes I spent hours sorting and this time I put on opaque tan pantyhose first then started again, shorts then pants, next rompers, overalls, coveralls & pantsuits and then dresses. I did blouses and jackets while in shorts or pants. Buying a wig was easy but found out you get what you pay for but finding shoes was (and still is) nearly impossible! I wear a men’s 13 meaning 15 wide women’s! The stores don’t carry anything that size and mail order is not always as described
At 14 I was home alone from school while parents worked and my sister was away on a trip. I was going through her closet for something and saw her old prom dress that I admired. I had seen her and her girlfriends playing around the house growing up playing with hair styles and makeup and was always drawn to it. I recalled how I played with her barbie dolls when younger and what fun it was to dress the dolls . I put on her dress and slipped into mothers room where she had a wig and put it on. Seeing myself in the mirror was enough to know I was hooked and loved my look and wanted this to be part of my life as well.
For me it seems I was always drawn to feminine things. In kindergarten there was a pretty pink princess dress that I was very fond of. For a Christmas skit I played the part of an elf and wore red tights which felt great. I often wore my sisters yellow satin and chiffon party dress. It tied in a big bow in back. I wore white tights and black patent leather shoes. I wore this around the house and in my room often. From around age seven to ten I was in cub scouts. I always volunteered to play the female parts in our skits and plays. My mother always made sure I had everything I needed for my costumes. It was during this period of my life I became aware of men dressing as women on TV sitcoms and variety shows. Milton Beryl, Flip Wilson as Geraldine come to mind. I began noticing how girls and women carried themselves and how they dressed. I loved going shopping in the women’s department with my mom and running my hands through the lacy silky slips and nightgowns. I loved to watch the women on the Lawrence Welk Show with their beautiful dresses. I watched Hee Haw to see the pretty women. It was around this time I looked forward to perusing the pages of the Sears Catalog noticing the dresses and skirts but mostly the lingerie and foundation wear. I noticed women’s makeup, hair styles, and jewelry. Bugs Bunny and Daffy Duck were crossdressing in cartoons. I loved to play with Barbie dolls with my sister and the neighbor girl that I always had a crush on. I think I was about ten when I told my mom I wanted to dress as a pretty girl for Halloween. I begged her and I cried until I convinced her I needed to dress as a girl. She bought me a beautiful red with white polka dots dress that came a few inches above my knee. She bought me my own bra, slip, panties, pantyhose, shoes and a very nice blond wig. I was so thrilled to go to a Halloween party as a girl. Mother did my make up painted my fingernails and helped me get dressed. When I looked in the mirror I saw the girls I always felt I was. I kept the clothes and wig in my room for several years and wore them when I was alone and feeling feminine. In Junior High my desire to crossdress became stronger. I started stealing girls clothes from wherever I could. My girlfriend’s mother’s bra, my friend’s mother’s matching bra and panty set, my aunt’s dresses, bikini, bras and panties she had in a bag to donate. I would dress up almost every night in my room and was soon pleasuring myself imagining I was a girl. In High School I dressed up as a cheerleader a few times and performed with some other boys in front of the whole school. I started going out dressed and began purchasing clothes at department stores. Whenever left alone I was getting dressed with complete wig and makeup. My parents knew I had an affinity for crossdressing. My mother cautioned me to be careful and this was T normal behavior but if it made me happy. I fell in love with my now wife. A week or so before our wedding she moved most of her things into the home we would live in. For several nights before I tried on every one of her dresses, skirts, blouses, and nightgowns. I had some wigs and makeup I had hid away. On the second night of our honeymoon in a hotel room I put on her bra, panties, slip, nylons, and dress and confessed to her I was a cross dresser. I wore her high ties to bed the remaining nights of our honeymoon. I know now that was not fair to her and I should have told her before we were married but I hoped she would enjoy my feminine side and embrace my crossdressing but that didn’t happen and she still has a hard time accepting it.
Always happy gen xx
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