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Thread: Teenage Crossdressing memories

  1. #51
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    I think tennis dresses are very sexy and cute!

  2. #52
    AKA Lexi sometimes_miss's Avatar
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    I spent most afternoons after school at home wearing my sister's clothes, trying her make up, styling my hair like hers, using various hair accessories too. She always also had quite a few current girl magazines (Cosmo, Glamour, Madamoiselle, Vogue, etc), and I loved reading those, too. She was at college or working, both mom and dad worked until dinnertime, so I knew I was pretty safe. A few times my sister came home early and I had to scoot back to my own room to change back, but that was rare. We also had a dog, so even when sis did come home, the dog would come running to her and she would immediately take it for a walk, so I still had time to get out of her clothes. I pretty much never borrowed anything that she was in her current collection of clothes, and as far as I know she never had a clue. When I finally came out to her almost 30 years later, she acted horrified, and never said anything to give me the feeling that she knew I had ever been 'borrowing' her clothes back then. After she moved out, she left one particular minidress made out of some cool feeling polyester or nylon material called qiana; after I found it stuck in the attic stored away with a lot of other stuff she didn't want anymore (mom was a pack rat), I took it for my own. I loved wearing that dress, and kept it for years.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  3. #53
    Aspiring Member Desiree2bababe's Avatar
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    The teens years were the best although also the most worrisome. I got caught regularly by my mother and eventually ended up in counseling, which did help me understand transvestism better. Must say ages 18 and 19 were the funnest though as I learned how passable I was and desired by men. Those nights on the dance floor were the best.

  4. #54
    Senior Member Jennifer in CO's Avatar
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    Threads like this is why I wrote down how my childhood/teen years went. May post it someday somewhere. Suffice it to say while my Mom and I were DADT she was well past just supportive in late teen years

  5. #55
    W.Y.S.I.W.Y.G. Jason+'s Avatar
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    Like many I discovered panties in my early teens. During this time one of my younger brothers helped my parents "find" my collection of panties. This led to a very red faced conversation from my side and my parents asking me to promise never to bring another pair home. They told me it was a road I didn't want to go down. With one short lived and guilty exception I kept my promise. They have since softened their stance and are happy to have me any way they can get me.
    "You are not an accident, nor are you malfunctioning. You are performing EXACTLY as coded." For many "Man in a Dress" is the worst atrocity commit-able; for me it's just reality. Click to Learn About Me. Click to Complain About Me! There is a fine line between brutal honesty and honest brutality. It is rarely in the same place for the sender and the receiver.

  6. #56
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    I am the youngest of 3 with 2 older sisters that were 6 and 7 years older than me. Well into my early teens I had plenty of afterschool 'home alone' time (this would be anywhere from 3-6 hours depending on when I got home and when my sisters did as they were very involved in aftershool activities). And for a young CDr our home was a paradise! My mother was a total pack rat (probably from growing up dirt poor herself) and kept almost all of my sisters old clothes from when they were younger. So I was home alone in a house filled with tons of perfectly fitting girls clothes. My father even had built a huge walk-in closet in our basement for my mother and sisters to keep there clothes in! My sisters had so much stuff - dresses, skirts, blouses, jumpers, even their old shoes! I wore their panties, tights, vests and training bras, and pantyhose. I wore almost everything of theirs that I could and I was one of the best dressed little CDrs you could ever meet. And this was the 1960s and early 1970s and girls clothes were GIRLY. One of my sisters even had some wigs (she obviously was experimenting with her own looks) and they were just the icing on the cake for this little CDr. There were even ballet outfits and a skating dress (even though to my knowledge neither of my sisters skated). I dressed almost daily until about age 15 in perfectly fitting and age correct little girls, pre-teen, and teen girls clothes! Complete outfits head-to-toe, shoes-to-wig, inside-out! ! Eventually my sisters grew older and moved out and eventually most of the clothes were gotton rid of before my parents moved to a smaller house.
    Luv and hugs
    Patti

  7. #57
    Stop that, it's silly.... DIANEF's Avatar
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    I was a teen when I first put on a dress (15) though I had worn underwear, tights, swimming costumes and such for a long time before that. It was a sexual thrill but the dress changed everything. Looking at myself in the mirror made me realise that this was what I wanted, to look as much like a girl as I could. It has been ever since. The funny part of the story is that my mum came within a hairsbreadth of finding me in my sisters room (her dress), only a creaky front door hinge gave me enough warning to race to my own room and dive under the bed covers, dress still on. First time I ever wore a dress and I almost got caught!
    Here today, gone tomorrow....

  8. #58
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    Such wonderful stories! As for moi, clothes hampers, but I was 'selective' in what I wore.... grin.

  9. #59
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    I have an early memory about wearing mum's clothes.

    I was about eight and keen to wear a bra. I got one from her bra drawer and put it on. I stuffed it with socks and waltzed round in my boobs and her lipstick. But the window cleaner suddenly arrived and in panic I pulled it off, detaching one of the straps.

    I re-sew the strap in a very amatuer manner, leaving marks on the bra from my dirty fingers.

    Nothing was ever said....

  10. #60
    Member Read only April T's Avatar
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    Didn't have sisters so not too many chances as a teen. That changed when I was 17 and had a girlfriend for awhile. Told her about wanting to wear panties. Over next few months, she would dress me etc. I was hooked. She also introduced me to my first man.

  11. #61
    Gold Member Maria in heels's Avatar
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    My dressing started "pre-teen" and of course, with my stepmother's heels. I started wearing them at an early age...she was a size 5.5 so I was able to wear them and walk around the house, along with one of my sisters, but I always have first choice and loved this pair of black "Bakers" patent leather platform pumps with a thicker heel from the 70's i'm guessing. From there, it progressed to underwear and pantyhose from the dresser drawers, and no dresses, as they were too big. I do remember as a teenager, getting a dress from the tenant upstairs..it was a beautiful strapless dress that flared out into a full skirt. I finally got enough nerve to go to the local "Rainbow Shops" and buy a white cloth peplum dress that zipped up in the front. I loved that dress and still have it in my storage cabinet. My first pair of shoes were these black patent leather stiletto pointy shoes from Fredericks of Hollywood - back in the days when you had to go to the post office and buy a money order and send it in with the order form. I also bought a pair of white leather pumps, and dyed them purple because I wanted that color...

  12. #62
    New Member Erin.Sometimes's Avatar
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    I started out around 12 or 13 years old, so about 11 years ago. I don't really have much in the way of stories, honestly it was pretty mundane. I was just fascinated by my mom's and sister's clothes and shoes (back when I could still fit in their shoes). Everything was just so different, there was so much variety compared to my array of jeans and t-shirts. I got super paranoid after I started experimenting with makeup that someone would find out. I was worried I wouldn't wash it off well enough and some days I swore I could still smell it on me when I walked in to school the next day, but no one ever really caught on about the makeup. The only time I really got caught was when my mom was going through one of my drawers for some reason and found a couple old Halloween costumes I had stashed away. Took a break for a few years after that and got started back up a couple years ago.

  13. #63
    mini kilted chick t-girlxsophie's Avatar
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    I stayed at my grans at weekends and on school holidays and that's where my dressing started around 10yo.There was a lot of my aunties outfits stored there Inc bridesmaid dresses,and even her school uniform,This was in the mid 70s.Can remember the first time I dressed,,although not why.I first wore playtex bra and girdle,black tights Yellow maxi dress and pink button thru cardigan,thankfully my colour co-ordination has improved.This led to me dressing up in my mum's clothes any chance I could get,although I was the worst at hiding my activities and got caught a few times.My mother has never got her head around it ever since

    Sophie
    Last edited by t-girlxsophie; 12-08-2018 at 10:22 PM.
    We look to Scotland,for all our Ideas of Civilisation-Voltaire

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    A woman who loves to wear beautiful clothes is like a flower.
    A man who loves to emulate these women is a special flower-a rose
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  14. #64
    Member AllieBellema's Avatar
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    The interest began with me around when I was 12-13 when I got the internet and around that time I first saw my grandmother watching movies like The King and I and Gone With The Wind. I started looking stuff up online from there and fell in love with what I saw. I had to be careful at first because my computer was right in the living room so I had to wait until night when my grandparents were asleep and I had the living room to myself. I'd even print a few photos to keep in a magazine in my bed so I can look at them as I prepared to fall asleep. When I got into my High School years, I got a new computer and it was moved into my room where I had more privacy.

    Also, my grandparents would let me stay home if I want to instead of going for a ride with them. I'd use it to explore my interests. My grandma was a K-Martaholic. She had tons of clothes to look through and I'd take the time to pick some things out to try on. Halloween 2000, I had my eye on a southern belle dress I loved. I managed to convince my grandpa to let me "buy an expensive halloween costume", not sure how that got past him but probably had alot to do with the fact that my grandpa didn't really care much aslong as I was happy with what I was doing. I nearly willingly showed my grandpa after I got it, on Halloween night. He was talking with his brother on the phone and, during that I chickened out and opted to not show him after all. I also bought other stuff at stores to wear, mostly out of halloween costumes.

    The oddest experience was when I ordered myself a large hoop skirt. I paid for it out of money I made and placed the order via mail. My grandpa got the package and held onto it when he thought it was a Christmas present. He came to me with the open package, asking what it was. All I told him was that it was "something I ordered for myself". He gave it to me and walked away without asking anything else. That moment still blows my mind to this day on how he didn't really care much. Anytime I had the house to myself at that point, I would use it to dress up. Of course, as I explored other interests, I sealed up the boxes and kept them tucked in my closet. Eventually, when I went to move away, I marked them as "halloween costumes" and threw them into another storage closet trying to hide the fact. Wasn't until another several years later I would get back into this with full force.

  15. #65
    Aspiring Member josie_S's Avatar
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    I told this story in another thread a while back but I love it--I had such a great time even if I was absolutely terrified!

    My cousin moved in with us when I was like 16 and she was about 18 and we were roughly the same size since I was little bit of a late bloomer. One night my parents took everyone, including my cousin, away for the weekend and I stayed behind; I can't remember if I made up some excuse--I hope I did just to have this time to myself and try on her stuff! Anyway, as soon as I could I raided her clothes. Then I found her make up OMG. I remember she had blue eyeliner and red lipstick and red nail polish...I'm sure I slathered it all on like a cartoon character but I loved it so much. For the first time, I dressed head to toe minus a wig (but my hair was long then) and I spent that whole day dressing up and trying things on and wow, I was in heaven. Then I found her one piece bathing suit!We had a hot tub and I climbed in and just giggled and soaked and loved the sight of my painted toes above the bubbles of the hot tub. And I knew they wouldn't be home until late the next day so I was free to indulge.

    I washed everything I borrowed and folded it and put it all back where and how I found it (crossdressers get good at this, I think) and I would never do anything like that now. I was 16 and of course would never do anything like this with anyone elses clothes today, but what a time. I just wish I had pictures :P

    I HAD A BLAST!

  16. #66
    Sarah Adams Vintage4sarah's Avatar
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    I think that I have mentioned this before, but there is a vivid memory that stands out the most. I had dabbled in my mother's sister's and aunties nylons for most of my preteen years. I was limited due to my tall height and my female relatives being short. Then in my teen years a golden opportunity lands in my lap and I took advantage of it.

    I was a responsible kid that had plenty of jobs around the neighborhood, especially taking care of their pets when they traveled. For three years, I 'dog sat' for one of our more affluent families while they returned several times a year back to Europe. They had an older daughter who was tall. After my first exploration of their wardrobes, I finally got the courage to sample cloths that fit me and I was amazed at what I could create in the mirror. There was even a hair piece and some shoes that fit. For the first time I was 100% dress as a woman and I had the time to enjoy it as their dogs got their exercise outdoors. The realization that I could transform myself and the excitement it brought to me was exhilarating. The seed was planted !
    Sarah Adams, mature girl from NH. My photos are on Flickr under vintage4sarah !

  17. #67
    Platinum Member Crissy 107's Avatar
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    Sarah, You’re lucky the dog didn’t escape, I can picture you running down the block in heels.
    Crissy

  18. #68
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    I guess your story didn't end like all those fantasy stories of house sitters being caught and encouraged to dress.

  19. #69
    Aspiring Member TiffanyTgirl's Avatar
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    Sometime around 5th grade I discovered panties, red satin bikinis to be precise. After that, I was hooked. Often spent time looking at the Sears catalogue and JC Penny's. Remember those? Not only did I like the lingerie section for the nearly naked women, I loved looking at all the lingerie and wished it was me wearing it. I also thought that I should have been a girl. Seemed right at the time. I can now buy whatever I want, but still have to fight for the private time to dress up

  20. #70
    New Member emmarinn's Avatar
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    I remember one piece swimsuits being my favorite thing to wear when I was 13 or 14. They are so feminine and I would just lounge around the house in one of them whenever I could. Corsets were amazing, just feeling them tight around my waist was soothing in a way. I remember hanging out too much with some neighbors that were friends with my family. Their children were all girls and I was friends with them. They would let me just be there or use their computer in one of their rooms and that was my chance to wear clothes of a girl in her teens and early twenties which was a bit more provocative but still close enough to my size and shape. I wish I could go back to that time I didn't have wide shoulders or a belly

  21. #71
    Sarah Adams Vintage4sarah's Avatar
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    Thankfully Chrissy, the dogs were free to roam in a fenced-in yard. The longer they played, the longer I got to savor the thrill of being enfemme !

    Quote Originally Posted by Crissy 107 View Post
    Sarah, You’re lucky the dog didn’t escape, I can picture you running down the block in heels.
    Sarah Adams, mature girl from NH. My photos are on Flickr under vintage4sarah !

  22. #72
    New Member JennaDcd's Avatar
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    I remember from about 13 to 16, every time we'd visit someone's house as a family I'd sneak off when the moment was right and sift through the lady-of-the-house's panty drawer or laundry basket. Two of my aunts wore my favorite style, satin string bikini panties. I'd stuff a pair down my pants, go into the bathroom, quickly masturbate, then return them to the drawer (I never leaked on the panties, so they were returned clean!). Over time I'd eventually get up the nerve to steal a pair and take them home, put them on in bed, straddle my pillow, rub my behind, grind the pillow until I came, then throw them away right away so I wouldn't get caught (wish I would have kept them for more than just ONE use, LOL!). I remember taking a red pair, black pair, and white pair.

    Other than that, I remember trying on my older sister's bras, panties, skirts, etc.

  23. #73
    Senior Member SaraLin's Avatar
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    Funny - about the only time I DIDN'T crossdress, or at least think about such things, was my teen years.
    I guess there was just too much going on at the time (school, work, getting my license and car, trying to find someone to like me enough to date me, etc.)

    Military life right after High school made it near impossible, but by then the feelings were back.

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