Viewing 34 reply threads
New Forums
  • Author
    • #731651

      I know we have all talked about that magic first item of clothing. The first item we put on that made something click inside us. Well many of us have anyway. LOL.

      For me it was a full slip. It was the late 60’s I think. My mother wore these every day for work. She had like a smock top and a black skirt. But it was the slip. With the light cups and straps. The silky feel. It was like nothing I had ever felt before, slipping it on and it sliding down my body. I don’t even remember how many times I tried that – but that memory is so vivid in my mind. I think having boobs as a boy was a part of that thrill and then what lead to bras. Bras are still my favorite item of clothing.

      I love to look at vintage lingerie, well somewhat vintage, and of course eBay is my fix. One day I happened to see slips. And it clicked. I could have one of those of my own now. I watched eBay for a month or so and picked out one and purchased it. Oh my. It feels so good, so femme. So reassuring. So calming. I had just never thought about “going back” and getting one of my own. But I am very glad I did.

      If you’re an old softy you might want to look and see if you can pick up “that first item” I can recommend it. Just wanted to share.

    • #731658

      Girls tights at the age of 4/5.

      Love Melissa Sue

    • #731667

      I can’t remember that first item of clothing that brings back so many memories, that is how long ago it has been.

      I think 2 items stand out, swimsuits and shapewear.   Odd combination indeed.

      I remember trying on my mom’s purple swimdress.  It wasn’t sexy or anything like that, but it was my first foray into wearing something that was lycra/spandex, and I remember loving the feeling of both materials against the skin.

      The 2nd item was shapewear.  My mom had this mid waist shaper.  Unlike shapers like today, this one was made of rubber, you can actually smell the rubber in the fabric.   I remember the tight feeling and how much I loved being squished into this shapewear.

      Not sure if I would like to own these 2 pieces of nostalgia, maybe the shapewear.   Unfortunately because it is vintage, it comes with vintage price tag.

    • #731672
      Angela Booth

      My first item was actually a few as it was my mother who dressed me up for a fancy dress competition when I was four. It was a sisters dress and shoes, a fur stole and a floppy hat with a bit of makeup! The first item I chose to wear after that was one of my sisters dresses then everything else followed as I grew.

      Back in the 60’s and 70’s  mother wore slips as well and I loved them. When I first came out to her she gave me a dress and a slip too with other items. I collected quite a few when they were available, glad I did as the prices for vintage slips are eye watering now.

    • #731683
      Liz K
      Managing Ambassador

      It was a bra when I was 4.  Got snatched away by my aunt.  I started actively dressing when I was 11.  Mom’s pantyhose caught my eye.


    • #731684

      My remembered #1 was those stay ups of my moms but I also remember my first slip fondly, it was heavenly.

      • #731685

        Same here Wanda, slips and gartered stockings 😉👍

        Nothing like the silky allure of them.

    • #731699

      A pair of orange Danskins tights when I was maybe 5. Mom caught me innocently trying to pull on my younger sister’s tights out of curiosity one day and yelled “STOP! You’ll ruin them!” Then she offered to get me a pair of my own. She did.

      I guess she figured I’d outgrow them and lose interest. Well…


    • #731712

      Hi girls,

      For me it was the bra top of one of my mom’s swim suits. I put it on, tucked my private parts between my legs, stood in front of the full length mirror, and realized that was what I was supposed to be, a girl!  Bras have always had the most special place in my feminine heart and now I get to wear them, as a woman, every day, heavenly bliss!


      Ms. Lauren M

    • #731724
      Caty Ryan

      A mixture….. Too long ago to remember the actual very first item.All my Mum’s, no sisters in the family

      1/. One piece blue swimsuit, for some reason she kept it in the outside laundry??Tennis balls for boobs, itched like nothing on this planet. Cold concrete floor, hard to think of “lolling on the warm sandy beach”

      2/. White bra and long legged panty girdle. Also strapless bra, including the one I cut the straps off to make it strapless. Mum was not impressed…..

      3/. Later on when left alone for the weekend, the full bit, with petticoats and dresses over number 2/.




    • #731727

      for me, I played with moms things, looked and more at the fredricks from hollywood cataloges and was all a twitter, but put all those thoughts aside for years (except fora few dalliances). But what got me going was my wifes discarded bra.  I slipped it on and memories and feelings from I dont know where came flooding back.  I try and wear that same bra daily (even though I have nicer ones now)  That happened at age 62 and I came out to my wife a month later.

      • #738904

        same here…  mid1970s, bored kid after school… reading Mom’s Cosmo.   those Fredericks of Hollywood ads.   tried on a few pieces of her lingerie.

    • #731738

      From the very first time I tried on a pair of pantyhose I was instantly hooked.  Still love them to this day.  Then l added a full slip to them and what a great combo.

    • #731742
      Trish White

      Hi Dani,  thanks for the post. My first article(s) of female clothing was a garter belt and stockings. I had never felt like I did the first time I put the garter belt on and the stockings over my legs. I was in Heaven.

      Trish 💖

    • #731743
      Evie Wonder

      I think I was in 3rd grade and discovered a pair of my sister’s panties -white nylon with ruffles around the leg opening, I was so bold that I wore them to school and remember getting teased by a couple girls who saw them peeking out of my pants. Totally sissy I think, but still give me a thrill.


      • #732045

        I’m pretty sure I was in 3rd grade when I found the slip(s). That was well before puberty for sure.

    • #731757

      For me, it started with my sister’s pantyhose when I was 12.  Pantyhose are still a staple in my wardrobe.

      Over the last 3-4 years, I have really focused on my whole look, hair, makeup, jewelry, perfume and nail polish.  To think, it all started with nylons!

    • #731887

      My first was actually a nightgown and panties. I think I was about 6 or 7 and had to stay at a friends house down the road when my parents went out of town for the weekend. I was friends with the girl that lived there and her Mom took care of us quite often. Anyways, we were out playing in the woods behind their house and both got super muddy because it poured as we were playing. We got to her house and her Mom got us towels to dry off and get all the mud off. Then a quick wash off and re-towel.   Then she cam back downstairs with her daughters nightgown some underwear and one for me as well. She said since I’m staying the night why don’t I just wear that. I didn’t complain or even think second thoughts about it. We got to stay up watching TV in our nightgowns and then went to bed. The next morning she hadn’t washed our muddy clothes yet so we just stayed in our nightgown for the day.

      After that she always offered me a nightgown and panties when I was staying over there. I loved it. This went on till I was about 12 and about 1 weekend a month or so. Even when I outgrew the original nightgown and panties she had bought me new ones in my own size a couple times as I grew.

    • #731913

      Even though my sisters dressed me as a girl when I was 3 to 6 years old, it was a bra, panties, corset with tabs to hold stockings and nylon stockings that was my first real feeling for feminine clothing.

      My sisters were discarding these old items of apparel as they had been replaced with newer items.  At 12 when I found these items I wanted to try them on.   I have never looked back since that day and now have a nice small wardrobe of female clothing all to myself.

    • #732047

      For me it was nylons followed by the bra.  Over time I learned of the sensation of a slip. The sensation and look gave me such a thrill.

    • #732143

      I shared a room with 2 younger brothers so although I had desires I never had opportunity. One time I had to wear my sister’s tights for a dress rehearsal and later a play at school. That was probably my first time even though it was known. My first skirt was a temporary thing. I took the cover off a broken umbrella and sewed it on to myself for a few minutes. The first time I wore actual clothes was age 12. I was home sick from school and my mom left me alone for the first time to do a quick shopping trip. There were some clothes a neighbor left for my sister to try on. I put on a plether jumper for a few minutes before my mom returned.

    • #732155

      My first item of women’s clothing was a pair of my sister’s baby blue nylon bikini panties. I saw them on the dresser in our shared bathroom and had an incredible urge to try them on. I was hooked and looked for more of her things to try on from that point forward including pantyhose, leotards, slips, and babydoll nighties. My first actual purchase of an article of women’s lingerie was a garter belt and stockings. I was always enamored with how the models looked in the Sears catalogs and my father’s girlie magazines, so I was determined to get one of my own as soon as possible. Finally, did it when I was about 17 years old. I was nervous as hell, but the young saleswoman was very kind and just smiled as she rung me up with no hurtful comments.



    • #732182

      My first item was my sister’s pretty beige half slip, I saw it and loved the feel of it and tried it on. From there I was hooked, Then it went to pantyhose. My Mother’s and sisters panties. I was about 12 when I started wearing Women’s clothes

    • #732197

      Looking past my first pair of heels, a pair of thigh highs and garter belt the ex had left behind which I wore with the first heels I bought for myself and that made me go “ahhh ha”  and revealed my crossdressing desires. Turns out that in what I am sure was a FU gesture, she left behind a bunch of lingerie I had bought her, mostly still with tags. Pays to be with a bigggg girl as it is all my size!
      Oops like I had the last laugh!

      • #732251

        Megan –

        Had the same thing happen to me.  My ex left a garter belt and stockings behind when she left.  I enjoyed wearing them in the evening after getting home from work. It wasn’t my first venture into dressing as that happened when I was younger wearing my mother’s clothes when I was home alone.  It did however rekindle the flame that was burning inside me.  Throughout the years I have ventured in and out of dressing, mostly lingerie.  A couple years ago though finally admitted to myself who I am and have been dressing since.  It may be when I am home alone but it is nice being able to be me.


    • #732248

      My first item of clothing was actually 3 items, but all were the same; they were nylon panties. I give a little detailed account on my Profile Page.

    • #736969

      I remember that the very first piece of women’s clothing I wore was my mother’s floral patterned bathing suit.  I had always seen her wearing it and it was so much more exciting than my swim trunks.  She had an intimate cabinet in her dresser with two pull out shelves in it.  The top shelf had bras and panties and the bottom had stockings and her bathing suits.  I went right for the bathing suit and that was the gateway drug that got me into her underwear drawer then into her closet… and years later here I am.

    • #737389

      [postquote quote=736959]
      I think your dilemma is the same dilemma we all have. The shame, the guilt all those feelings. And yet they won’t go away. At some point there has to be a balance. And for some of us it’s so hard to find that balance.

      If we let the “girl” win – we go to far. If we let the “boy” win – who knows where we end up.

      I’m tired of fighting that fight. They are just going to have to learn to play well together from now on. Two sides of the same coin.

      Don’t give up. I think if we give up the “girl” we end up losing the “boy”…

    • #737416

      I don’t remember wearing femme clothes when young. I wish now that I had had that experience. I do remember being curious enough, when less than ten, to rummage around my mom’s drawers once, but that didn’t lead anywhere.

      The first item that I bought for myself, last year, was a pair of gypsy style pants that I saw in front of a scrubbs type of store, for nurses. That started everything. My wife was not impressed. 🥳

    • #737431

      My mother always wore tights, and I was always fascinated with them. I must have been about 5 when I first tried a pair on. I was instantly hooked by the way they felt and it continued regularly from there. She had so many boxes of them that I could easily take a pair now and again without her noticing, so there was a constant supply. I got caught a couple of times but as I was only little it was no big deal. I did get caught when I was about 12 though. I had a big wardrobe and there was a coat in it that my aunts friend had given to my mum and she never wore it so I stashed all my tights in one of the pockets. She found these one day and assumed they belonged to my aunts friend but when she mentioned it to my aunt, she said the woman didn’t wear them. I denied all knowledge of them and nothing else was said, although my mum must have worked out that they were mine.

      • #737494

        my mothers bra nad panties and stocckings at around 10. later after i got married wifes and would wear a whole outfit with makeupand nail polish later on she bought me my own . a bra and pantie set a nighty and amakeup kit. after that i started with my own things. i ened up with more thanshe had from wigs on down even womens bikini bathing suits

        I had 60 bra and panti sets and 10 pairs of hels and shoes

    • #737437

      Technically, my first item of clothing was a pair of woolly tights when I was 7 in a school play. However, I distinctly remember having to wear a cardigan when I was about 5 when I visited my Grandma’s. She lived in an old house and, if I stayed the night, she insisted I wear it once I got changed into my pyjamas so I didn’t get cold before I went to bed.

      I know what people are thinking: cardigans are unisex and not really a specific feminine item. But, this was a homemade knitted thing in a banana yellow colour with fish eye style buttons all the way to the top. As a young boy it felt incredibly girly/babyish, and whilst I didn’t complain about wearing it, I knew it would be the sort of thing I would be teased about if I had to wear it outside.

      I felt a similar thing about t-bar sandals, a staple of my childhood, which I continued to wear much longer than other boys on my street.


    • #737438

      Like so many here, pantyhose were my gateway drug also. Having no CD experience as a child or teen my first encounter with them were a pair of my wife’s that she had discarded. It was quite pleasurable, but I put such notions aside thinking it was a kink and way over the top. Fast forward about 30 years, my wife is called out of town for a few days and what do you think I do now that I am on my own for the first time in a long time? You guessed it – right to Walgreen’s to pick up a pair of my OWN pantyhose, which I enhanced with  pair of inexpensive heels and a kimono robe. Euphoria!

      And now here I am – and the better, more well adjusted person for it.

    • #737444

      The first item was a discarded pair of panty hose when I child. It was a magic feeling with them on. As an adult, my first purchase was black garter belt and black stockings. I tossed those during a purge and regret it to this day.

    • #737448

      For me it was my friends moms bra. I used his bathroom one day and as soon as I walked in I was mesmerized! On a drying rack in the shower were bras, garters, stockings and pantyhose! I reached out and touched the stockings. It felt wonderful!! I proceeded to take off my shirt and try on her bra. It was a black,lace one. I stood there and admired myself in the mirror. I was hooked!! I became an undresser from that moment on and don’t regret one minute of it!!

    • #737473

      My first time was around 6 or 7 and put on a pair of my cousins tights little did I know that would be the start of a lifetime of having so much fun with clothes. A couple years later I was going through some bags of old clothes my mom had in the basement and found a pair of her panty’s in a bag and had to just try them on and wow they felt so good to have them on and after that I would go through any new bags of clothes she would be getting rid of to find some new jewel for myself and would put into my hiding place. My first time I would buy new things would be my first order from the J.C.Penny’s catalog,  I ordered some panty’s and my first pairs of pantyhose, was so scared going to pick up my order at the store..  The rest is history.  LOL

    • #737504
      Eva B

      My first real fem item was a pair of white go go boots (circa 1973) that was in the attic.  They were PVC and so cute. They just fit my size 9 male feet.  How they got ther I do not know. They were women’s size 10 and an awesome fit. Later the next item was a black Merry Widow corsolette that I found in the attic.  They were very influencial in my dressing.


    • #737509

      My first item was a pair of my sister’s panties, and I was hooked almost immediately.  The greatest – and probably most influential – thrill was, probably, the first time I got up the nerve to pull on a pair of tights; just how on earth would it ever be possible to feel that good?  There is never a time when I put on something pretty and it doesn’t feel fantastic; it’s always a real thrill and a massive boost to my confidence.  But there is no way you can ever beat the first time – so if anyone has a time machine for sale, I’m your girl…  Holly XXX

    • #737572

      my first item was my sisters pink satin panties,  I loved them.  From there it went to bikini bathing suits and pantyhose that were drying on the shower rod.  My first bra was also a pink 34c bra an took from a girls room. I was hooked

    • #737841

      The first item for me was my mother’s bra that I found in the clothes hamper when I was 11 or 12 years old.  After that first time, I would regularly check the hamper and wear her bras whenever I found them there. She caught me one time, which was very embarrassing at the time, but she didn’t make a big deal out to it. I suspect she knew what I had been doing all along.

Viewing 34 reply threads
  • The forum ‘General Chat “Life as it Goes On”’ is closed to new topics and replies.
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?