Page 44 of 44 FirstFirst ... 34424344
Results 1,076 to 1,088 of 1088

Thread: When did you first crossdress?

  1. #1076
    Member CatchQueen's Avatar
    Join Date
    Jun 2016
    Posts
    184
    Must've been 5-6...I know I was in kindergarten...I started with panties, pantyhose and gymnastics leotards.
    http://www.youtube.com/c/CatchQueen - My YouTube - I post there regularly

  2. #1077
    Banned Read only
    Join Date
    Oct 2011
    Posts
    462
    Aged 10-11. I'd get home from middle school an hour before any one else in the family. "Borrowed" my sister's clothes. I was saddened when she tossed them all at Goodwill a few years after that.

  3. #1078
    New Member
    Join Date
    Jun 2016
    Location
    So Cal
    Posts
    2

    Thumbs up Very similar to my beginnings

    I
    Quote Originally Posted by CCDTanya42 View Post
    Was 10 or 11 and had began masturbating by rubbing on my soft satin blanket on bed. Made me curious about wearing my mom's silky clothes so i went and tried pantyhose, panties, slips, girdles, and teddies.

    Was instantly hooked, and would rub and orgasm while wearing her clothes. Firing blanks at that age, so i could orgasm without making a mess.

    Was dabbler in CDing from then until early 20s when i started buying my own stuff (stripper heels, bikinis, etc) and as closet CD have gotten more into it in the past 5 years or so.

    My dressing has always been sexual and will always be sexual. Not trans, but enjoy being feminine and bisexual fantasies.
    I'd do the same, come home from school being alone for a couple hours meant making a beeline to the panty drawer.

    [SIZE=1]- - - Updated - - -[/SIZE]

    My first lingerie item in my collection was a black babydoll that mom had hidden away, probably destined for the Goodwill but luckily I rescued it. Perfect condition. I was probably 10 or 11.

    [SIZE=1]- - - Updated - - -[/SIZE]

    House sitting was a thrill for me too. Neighbors would go on vacation for two weeks every summer (1960s) and I'd be asked to clean the swimming pool. Of course they also gave me a house key. I'd finish the pool and it was off to the bedrooms (daughter and mom). Great fun playing in the lingerie.

    [SIZE=1]- - - Updated - - -[/SIZE]

    Quote Originally Posted by Li'l Miss View Post
    I don't know what age I was, but it was definitely pre-school. I put on a pair of my mother's panties and walked around the house in them. When she saw me, she laughed hysterically and said her panties were way too big for me. My desire to dress in women's underwear lay dormant for quite a while after that, then came back full throttle about the time of puberty. I raided my mother's lingerie drawer every chance I got until she caught me one day posing in front of the mirror in her bra and panties. She scolded me for what crossdressing might lead to, but bought me a package of white nylon briefs for my own. I've been addicted ever since.
    Yes I was already hooked on panties at 4 and was often seen walking around in aunts bedroom with her big panties. Can you imagine the sight? Mom told me these stories when I was older thinking it was just a passing thing. It wasn't.

  4. #1079
    New Member mickynylons's Avatar
    Join Date
    Jul 2016
    Posts
    18
    I would say it was when I young, probably around 8 or 9, when I would find a pair of my mom's nylons and play with them in the bath room. It wasn't until I was in my early teens that I started to occasionally wear a pair of panty hose under my jeans. Later on, during my first marriage, I would start experimenting with wearing my ex-wife's dresses and skirts...even tried her makeup and lipstick in private.

  5. #1080
    Member
    Join Date
    Jul 2015
    Location
    Osaka, Japan
    Posts
    221
    To some extent the question is what is mean by dressing as a CD. If it means just putting on a few female articles of clothing at home, I did this when I was very young, perhaps 10 or 12. If it means going out dressed androgenously, I did this in my mid 20's. If it means going out in a complete female outfit, I would answer my late 20's.
    In any case this was much too late and I wish I could have gone out dressed fully as a CD when I was much younger. So much time lost.

    The bottom line here is that I have wanted to CD ever since I could remember. It has always been a part of me.
    Last edited by PattyT; 07-08-2016 at 12:35 AM.

  6. #1081
    Stephanie58
    Join Date
    May 2016
    Location
    Southern Highlands, NSW, Australia
    Posts
    22
    My first memories of cross dressing are in my mid teens (I had no opportunity earlier as i was away at a boys school for the previous 10 years) when I tried on my mother's clothes. Perhaps a little earlier i do remember being fascinated by my mother's big heavy corset and suspenders.

  7. #1082
    New Member fun_girl's Avatar
    Join Date
    Jul 2016
    Location
    Canada
    Posts
    20
    The first time I crossdressed, I was 13. I put my mom's panties, dress and heels. I was in heaven.

  8. #1083
    New Member Lori_Lyn's Avatar
    Join Date
    Jul 2016
    Location
    Rigby, Idaho
    Posts
    24
    It was Halloween when my older sister thought it would be fun to have a little sister to go trick or treating with.
    I was around six y.o. I have heard. when She put a old red dress of hers on me and a mask of course and she took me around
    the neighbor hood introducing me as her little sister if anyone asked. I was hooked and wore her dresses of and on
    until the day she moved out

  9. #1084
    New Member
    Join Date
    Jul 2016
    Location
    Uk
    Posts
    18
    I was always fascinated by women's boots as far back as I can remember, my mom had a pair of leather 70's black knee high boots with platform heels that I'd be allowed to wear during playtime, that would have been when I was 6 I guess, I loved the feel of my legs and feet encased in those boots and the feeling of a heel under the foot too, i got to the age when I was told off for wanting to wear them, guess mom thought I should have started to grow out of them by that time!

  10. #1085
    Junior Member
    Join Date
    Jun 2016
    Posts
    63
    I was 10. Folding laundry one night I found some curious items that made me feel squidgy inside. Mom and dad took square dance lessons on Fridays nights for some reason and sometimes my brother and sister were out too. I tried on the bra one such Friday night. Nice. Then the girdle and the slip. Oh my god! I remember hooking stockings one night but probably not then.

    It only took a couple of dress-ups before I was caught. Mom and dad were surprisingly cool about, considering it was about 1967. I recall them, or at least Mom, allowing that it was OK if I wanted to try those things out. I was way too embarrassed to pursue anything though.

    A few days later the kid across the street claimed to have seen me through the window 'in a dress and everything.' I don't think anyone believed him and he never mentioned it again that I remember. That's kind of odd now that I think about it. Anyway, all that failure was enough for me for a long time.

  11. #1086
    Junior Member BayBeeBlue's Avatar
    Join Date
    Jul 2016
    Posts
    43
    My first memory, would have to be , as vague as it may be, something to do with me having to wear green tights for a school play (aged approx 5-8) ....I could have been the tree....not sure.
    Next I remember, I'm trying on my mother's tights when my parents go to town....and getting caught once or twice puts me off for years with guilt, shame, abnormality,etc,etc.

  12. #1087
    Member wanda66's Avatar
    Join Date
    Apr 2014
    Location
    va.
    Posts
    313
    My gosh, the firt time like most everyone was with mom's panties etc, the last time was 5 minutes ago !

  13. #1088
    Member
    Join Date
    Oct 2014
    Posts
    129
    I was between 3 and 5 years old...hard to remember back that far.

Posting Permissions

  • You may not post new threads
  • You may not post replies
  • You may not post attachments
  • You may not edit your posts
  •  


Check out these other hot web properties:
Catholic Personals | Jewish Personals | Millionaire Personals | Unsigned Artists | Crossdressing Relationship
BBW Personals | Latino Personals | Black Personals | Crossdresser Chat | Crossdressing QA
Biker Personals | CD Relationship | Crossdressing Dating | FTM Relationship | Dating | TG Relationship


The crossdressing community is one that needs to stick together and continue to be there for each other for whatever one needs.
We are always trying to improve the forum to better serve the crossdresser in all of us.

Browse Crossdressers By State