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My first experience with cross dressing occurred when I was very young and with an unusual garment. I have a vivid memory of it. I think I was about five and my mother had probably had enough of me and was lying on her bed. I jumped up on it and when I did my hand contacted a strange material underneath her dress. I asked what it was and she hiked up her dress just a little bit to show me and said it was a girdle. I was fascinated with such a strange garment and how it felt to my hands. Probably sensing my fascination and looking for something to distract me so she could relax, she opened up a drawer and got out another one for me before she lay back down. I spent some time handling it and the eventually managed to put it on over my clothing. It did keep me occupied for awhile although my father was not to happy when he arrived back from work. That was the beginning---years later, when I was older, I would sneak in her room and try on various items
@maureen76 I remember touching a bra my mother left on the floor when I was about 10. It was magical to feel the texture of the material!
That was 40+ years ago, I remember it like it was yesterday.
Caroline💋
@carolinecd306 Hi Caroline----yes, girdles and bras have kind of a magical quality---since they are garments that are unique to women---mysterious things made out of materials that men don't wear----these images stay with us
@carolinecd306 I just got finished writing a story about “First time“ dressing (Hope to post it soon) and I literally said the same thing you did in your comment. The memory is a sharp today as it was when it happened almost 40 years ago in the mid 80s. Funny how those memorable events stick with you so close.
@juststevie Yes Stephanie---those early memories of touching/wearing your first bra or girdle are magical and have a very powerful influence on girls like us---Hugs Maureen
@juststevie Absolutely, as a matter of fact I still buy bras of a similar style and material.
@carolinecd306 Yeah, I definitely get that. I vividly remember the first time I ever put Jersey knit material in my hands. It was slate gray with a floral pattern on it similar to the dress I was wearing in the public pictures I posted. It was material from the fabric store. She used to do a lot of sewing when I was little and it was all leftover stuff from then.
I asked my mom what this pretty, soft and stretchy material was, and she explained to me that it was a jersey knit. It was a rather large piece, and I used to wrap it around myself, imagining that it was a pretty cape or some kind of dress.
To this day, it is absolutely my favorite type of material. I have a huge thing for wrap dresses and I would say easily 90% of them are a poly spandex jersey knit.
It’s all her fault lol🤣
@juststevie Sounds like mom had good taste and set you on a course for excitement.
@carolinecd306 That she definitely did! I’m going to write a short story about an experience I had with her letting me dress up and some of her clothes. That way I would “get out of system” and stop doing it lol.
We can see how well that worked out lol
She’s quite supportive of me, but she doesn’t want to see me dressed. It’s still too hard. I’m her only child. I totally understand. I wish I could spend time with her dressed up, but that’s just probably not ever going to be possible. I’m grateful for her support though.
Hi Maureen,
For me it was one of my sister's dresses when I was eleven. These days, in the U.K. some schools allow the students to decide on which uniform to wear for the school term. Oh, to have been able to wear the girls' uniform for school.
Lynne
@denimwear so you started with outer wear while I started with underwear ---- there are many paths to a similar situation and that is we enjoy wearing feminine clothes
@maureen76 That’s a really cool experience. I bet your mother never imagined what would come of it lol. I can’t say I exactly remember my first time. I always have a tinge of jealousy for people like you who can vividly remember it. There are certain cross-dressing events, however, that I have very vivid memories of. As a matter of fact, I just wrote about one and plan to post it soon.
It’s funny how the most unsuspecting things led to our love for women’s clothing.
@juststevie Hi Stephanie---Thanks, I am not sure why it is such a powerful memory---It felt like I was sharing something special with her, like a daughter would---it made me feel close to her perhaps---not sure---but it is a powerful memory
@maureen76 Yeah, I completely understand the connection. With my mom‘s clothes, as well as both of my ex-wives, there was always a connection To them wearing their clothes. At the same time, it was something forbidden, so there was always an enticing element to it that made it all the more poignant
It really is interesting how these memories stick with us.
@juststevie I think the "forbidden" aspect of it is a very big part of that early experience---it made it more exciting --Hugs Maureen
@maureen76 Yes that is a big part of the thrill. Now that I can dress whenever I want, that element is completely gone. I know it sounds bad to say, but at times I miss it.
I was trying on a bunch of my partners dresses last night while she was working on her computer and although it was fun, I didn’t have to sneak around, so that aspect of it wasn’t quite as enticing as when I would sneak my ex-wife’s clothes knowing how pissed she would be if she found out I had worn them
I would still rather have things the way they are now, though. The way things were brought a lot of stress into the marriage. I’m glad it’s behind me, but I do miss that “forbidden” feel of something I know I wasn’t supposed to wear against my skin.
@juststevie what you say is true---when sneaking out dressing when young it is forbidden and exciting----now with knowing/accepting wives---that element is gone---except perhaps when going outside the home dressed where there is the "danger" of being read or ridiculed for a still mostly "forbidden activity"
@maureen76 Yeah, the element of running into someone I know dressed up kills any amount of “excitement“ I may have lol
It would be an absolute nightmare, if people I worked with found out about this. I would never, ever hear the end of it.
@maureen76 My first item of femmewear was my mother's rubber girdle back in the 50's. She was sorting through some clothes to go to storage, held up this rubber girdle and I had no idea what it was. She was petite and I was husky so she said "here, try it on!"
And that was the start!
@<deleted> your first experience was similar to mine---where my mother also encouraged me to try on a girdle---although not a rubber one---after the initial encouragement my mother didn't do it again---how about yours?--Hugs Maureen
Hi Maureen,
I love your story. I think many are/were intrigued by what our moms wore and also snuck into her dresser drawer drawers to try her finery. Thanks for sharing your story.
Alice
Thanks, yes it seems a common way that we are introduced into the world of women's clothing --- although the idea of a girdle starting it all is a bit unusual
Maureen -
Thank you for sharing your story. I spent quite a bit of tie in my mothers lingerie drawer when home alone. I remember trying on her girdle, it was a lovely feeling (this reminds me that I need to find one for myself - with garter tabs of course).
XOXO
Suzanne
I remember trying on her girdle, it was a lovely feeling (this reminds me that I need to find one for myself - with garter tabs of course)
So do I, and I still love girdles to this day. Oh yes, Suzanne, with 6 straps of course, cos 4 just don't hold stockings in place the same 😊.
Allie x
@cdsue hi Suzanne----a mother's lingerie drawer was an incredible place---filled with strange and mysterious objects made of materials foreign to boys and teenager---so stretchy and soft and yet firm --- so silky ---and to me, a panty girdle was the most enticing object of all and still is
I had been dressing as girl since about age five, coached by female relatives and other females.
In the 50s & 60s, it was not unusual for a girl to start wearing a training bra, a girdle, and her first stockings around the age of eight to ten, depending. (No pantyhose at that time).
I can still recall my first girdle and stockings and how they felt under my dress. The Playtex Living girdle, I recall, was very hot to wear in the summer months, along with stockings. I think one of the best memories though was the fun of just being a girl and doing things that girls do at that age.
@catgurl Hi Peggy--- it seems you lived my dream--to actually be encouraged and coached in to becoming a little woman by mother, sisters, and aunts---it must have been wonderful---I had to sneak in to drawers and try things on in secret---but I still understood how incredible and magical these items were because they were so different than what boys and men were supposed to wear and they truly represented what womanhood was, or at least what I imagined it was
@catgurl I remember the Playtex 18 hour bra advertisements.
I can imagine in those days wearing a bra for 18 hours was probably hell lol
I always enjoy "firt time" tales. They bring back such fond memories.
@jjandme It really does!! I think back with joy when I first started wearing my sisters and mothers clothes
these early memories are so magical for us because they represent when our love of women's clothing was first imprinted on us---I remember touching, and smelling, and wearing these magical items that were so foreign to my experience and that I couldn't resist---it was also the allure of the forbidden---but the memories stay with me afte so many years and it seems to be a common thread for all of us girls on this site
I remember trying on my Mothers Girdle when I was about 14. It also had garters which I put nylons on. It was so enjoyable
Yes, those were the days--- the first girdle experience sets up a lifetime of memories and enjoyment
It is those childhood moments that make us realise who we really are.
So true, but not necessarily at the time. I do not know what possed me at the time, but I was home alone and just decide to dress in all my mother's things. I hadn't been pini g away to do it, I just spontaneously did it head to toe, wig stocking girdle, etc. As I very vaguely recall I may have dressed a second time, but I have no clear memory of it unlike the first time. I then never gave dressing a second thought for many years until one day I decided to.wear my soon to be wife's panties. Even then it was not a true start to.anything and I did not wear, nor even think, to wear anything for quite some time. I then would very occasionally ask to wear her bra or panties in bed. She was fine with it, and we enjoyed a good romp. It qas just a slow process and I found mysle wearing panties more and more, and occasionally a bra until one day I realized I just really liked feminie lingerie both on my wife but also on myself. That slowly.grew until where I am today of dressing fully en femme when the desire hits me. Fortunately my wife is still content with me dressing and we still enjoy a good romp when dressed.
Experimenting with mother's underwear seems to be a common starting point, especially, for people of my age, when that underwear was so different from what boys wore. Today, in reality, the only truly distinctively feminine item worn by many women is the bra. (Yes, I know that women's panties are different from men's but only in detail).
What made all the difference for me, as a boy with no sisters and going to a boys-only school, was when I got to know girlfriends really well and became aware of the detail of what they were wearing - and why. Until then I admit I had given no thought to bras but soon learned how important they were to girls. I knew about girdles, stockings and suspenders but getting to know girls properly taught me all about the complexity of those garments and how they were chosen and worn. Feeling the material of a girdle on a female body, with its seams, panels, different elastics and even stiff bones was a revolutionary experience. I'm not sure that I would experience anything equivalent if I were a teenage boy in 2024.
@lionel The thrill of these undergarments is not only wearing them ourselves but also in experiencing them on the female body. The feel of girdle, nylons, and bra on a woman while you are kissing her is so very erotic---perhaps even more so than wearing those garments yourself.
I remember finding a pair of burgundy tights in the wash that belonged to my sister. I was probably around 12. I put them on and I was hooked for life! They didn’t fit particularly well, but at that point I didn’t care. I have crossdressed off and on (more on than off) ever since (I’m 68 now). First wife never found out, although my first experience out in public was wearing her clothes. Who knows, maybe she knew and didn’t care?
Yes indeed. So true. I handled my aunts bra at my grandmother's house and it wasn't long before I was trying it on.
