I was about 4 or 5...I tried on slips and panties first....I thought it would go away. Boy was I wrong!!
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I was about 4 or 5...I tried on slips and panties first....I thought it would go away. Boy was I wrong!!
I was in my early twenties when in a relationship at college with my then to be first wife. I found i liked the feel of her clothes against me when i was with her and then that progressed to experimenting with trying on when she was out. She never knew of my urges and after two years of marriage she moved on with some bstd she worked with. So naturally i built up my own modest little stash which i purged later when i got nervous of being found out by family.
Aged 2 or 3,pulled on a pair of my gran's panties, bounced around on the bed experiencing pleasure, and was discovered! Aged 7 or 8, found a way to turn my pyjama jacket into a skirt!
I guess I can put the blame on my mom. When I was born she had wanted a girl real bad. Apparently she dressed me up as a girl in some of the little girls dresses she had already sewn together. My dad I'm told didn't like what she was dong and put a stop to it. I found out later that she didn't stop doing it behind his back till I was about three. Mom has an old picture of me in front of her old dresser and me playing in her makeup with the red lipstick all over my lips and face. I guess I wasn't coordinated enough do put it on right then and or now...lol Later in my childhood I started getting her old panty hose out of the trash that had all the runners in them and stored them in the top of the barn. I later secured an old girdle she discarded and I also had a good stash of Sears and Roebuck, and Montgomery Wards ( we called it Monkey Wards) catalogues stored there as well. I would set in the hose and girdle and stare at the girls in those catalogues and all the bras girdles and hosiery wanting to be like them. I then progressed to when my parents were gone I would get her slips out and play with all the gear on. Even advanced to some play lipstick that was chalk so it could wash off easily. I also did all the guy things in school football, Ag (FFA) and Track. I loved a course in Homemaking that explained how babies are made and taught us how to wash dishes and cook, and then how to dress up for an evening with our dates...I listened when the teacher taught the girls how to dress...deep down I wanted to participate with them but had to keep the macho thing going. I hid all my feelings and suppressed them till after college and I met a girl and married her. She said she knew that I had played with her clothes and she was right, as its hard having someone near and wearing hose and heels and you have to wear jeans and boots...We are still married but now she is helping me with the dressing part and she is learning my feminine side with me as I don't know where it will lead me. I just know I want it to be with my wife...
I am in love with this site and the many good gals here...
Jaylyn,
Lipstick all over your face-YUMMY. Sears & Ward catalogues....the lingerie section, that brings back so many fond memories. HUGZ !
Well, my earliest memory of doing it on my own was when I was 13. I would put on my sisters nightie and other stuff while brushing my teeth in the morning and getting ready for the day. No one knew. Before that though, I have faint memories of my older sisters dressing me up and painting my nails and stuff. I may have been 3? When I was 5, my sister and I wore my moms skirts up to our shoulders secured with a belt and trampled around the house with sand buckets on our heads handles for chinstraps. I think I even still have the picture! So I guess from the very getgo!
I started dreaming about crossdressing at 5. Sometime between then and 13 I began wearing my mom's pantyhose (lol - such old-school pantyhose they were, too).
In my teens
My cousin' s panties and Gym Outfit
Then was dormant for some years
Again in my 20's and ever since
When I was about 4 I used to play with my grandmother's lipsticks and mum's jewellery. But I remember when I was only about six begging a girl day after day to let me wear her clothes. To my delight, she finally said yes, but of course I soon got found out. After that, I wore my mum's bras and stockings and played with her make-up and when I was in my teens I took every single opportunity that came my way to try on girls' clothes and experiment with their make-up.
Reading some of the posts, I often wonder how my mum might have reacted has she ever caught me wearing her clothes!
My wife made me buy a pair of high heels for myself to experiment - 4 years ago - very exciting again
About 3 years ago - discovered Heather in Las Vegas
Aged 4 or 5. Wore my sisters underwear and dresses. Knew it was wrong as I locked myself in the bathroom to do so. Now I do it almost 24 /7 and it feels right. The confused little boy is growing up into a confident woman.
Hmmmm I have vague memories from when I was quite young, perhaps 4 or 5, of playing with my moms nice church heels and her purse collection. The first time I vividly recall dressing up was in either grade 7 or 8 when I was looking through some old clothes and such to put together a Hercules costume for school. I came across two gymnastics leotards from my sisters and curiosity got the best of me. I loved how they stretched and hugged my body, can't forget the colours too! It was so different from what I was used to wearing and yet felt good, it felt right. I had always been intrigued by girl clothes and girls in general but never had the chance to experiment till then.
So I confirmed my feminine side while looking for a Hercules costume. Ironic?
Oh my! I guess I started in my early teen years. School was a great place to see the occasional up skirt live and seeing a pair of panties live was such a thrill. Then when I got home, sometimes Mom or Sis would leave a pair in the bathroom. Well, one thing led to another and as soon as I put a pair of nylon briefs it was wonderful. Then I started seeing ads in the back of Playboy or Penthouse for a place called Michael Salem's and I knew I was hooked. It took a long time to come to the realization that I am a cross dresser and even now, it is limited pretty much to underdressing but I have enjoyed it for many hidden years
Hard to remember the exact time but I'm guessing around 13-14yrs old slipping into some kind of lingerie that mum owned. What sparked that off is the real question! That feeling was so intense it never really went away through all these years. Oh and I was caught by her a few years later as well. I thought I would have a heart attack at the time but got through it ok. Said I was just experimenting at the time and genuinely believed it for a little while. 20yrs later or so here I am.Quote:
Originally Posted by Alexandra Santora
I was twelve, or so. No sisters in the family, so it was Mom's slips and petticoats; the feeling was magical. At the time, I thought: how can this feel so good and yet feel wrong. Looking back on it, I wish I had told my mother.
Norah
At about age eight though it may have been as early as age six. THAT was long time ago.
The first thing I wore... I always helped my mom wash and fold clothes. Some of her clothes were really soft and smooth. I like the way they felt in my hands when I folded them. So I sneaked a pair of panties and bra to try on. She caught me trying to figure out how to clasp the bra behind my back. We had a long talk about what clothes boys wear and what clothes girls wear. Unless I had wanted to wear girl clothes all the time I had better leave her clothes alone. I don't remember how old I was, pre teen perhaps?
So I did it in private for a few years till my girl friend caught me. She thought it was cute and helped me dress up more often but we never left the house except to go to a Holloween Party a couple of times.
as a young boy about 5 people would think I was a twin girl to my sister, (when I had a hood on over my hair) I think I felt weird at the thought of it, but sorta good about it too. when I was about 8 or 9, staying at my grandmothers over night she made me sleep in a nightie at the request of my aunt.
also made me wear a something over my hair like a girl. (it was very stimulating)
around the same time I would put on my mothers or sisters clothes, when I had the chance.
I used to put my hair in curlers every chance I got, I like the feel of it. and looking at a full head of curlers in the mirror.
my mother used to make my sister clothes, she would have me put them on, to check her work etc. if my sister was at cheer leading practice or as a surprise for her.
from there the pulling that way only got worse.
My earliest recollection is trying on one of my mom's girdles, it was a white panty girdle with a satin tummy panel. I was probably 6 years old. I had to hold it up, because it was too big to fit. I grew into them! Could not wait for the Sears and Eatons catalogs to arrive in the spring and the fall. I would go leaf through them and pick out my favorite girdle, bra or corselette on every page. That thrill & excitement has stayed with me all my life. Just now able to CD with my wife's knowledge and approval nearly 50 years later. Ina
I was really really little and tried on some of my mom's clothes. My mom freaked out because she didn't want my dad to see me like that. He was really homophobic and gender-normative, also prone to fits of rage and verbally, emotionally, and sometimes physically abusive. Actually dressing like a girl had to wait for college when some female friends made me up for Hallowe'en a few years running.
I have replied to threads like this in the past but always enjoying reliving the memories. Started pretty early not sure of age. It was out of curiosity with my older sister's bathing suit in the bathroom. Loved the feel and soon tried her pantyhose, then her ballet outfit. Soon I was trying her panties, bras, dresses, skirts and tops. She had one pair of kitten heel that fit perfect and felt so right! I snuck some of her nighties and would sleep in those. I liked that I could wear my sisters stuff. That way I was wearing what the girls in school were wearing. She had several outfits that were my favorite. Makeup came from my aunt. She sold avon and there was always a box of samples in the linen closet. No one ever missed what I took. Wish I had the forum back then!
Love to all,
LoriAnn
I'm so enjoying reading all these memories...
Alexandra - that you for posting a question that each one of us can respond to. We can identify with and enjoy each other's responses.
Hi Alexandra, It was some where around age 4 or 5 .