Page 23 of 44 FirstFirst ... 13212223242533 ... LastLast
Results 551 to 575 of 1088

Thread: When did you first crossdress?

  1. #551
    Discovering the Gurl Xandra's Avatar
    Join Date
    Dec 2005
    Location
    Minneapolis
    Posts
    176
    Sounds wonderful, Lucy xxx
    Quote Originally Posted by Lucy Lou View Post
    For me it was when I was about 16. Just one dress in the bathroom. it wasn't until I left home and got my own place that I really started putting on more things and it has just got more and more as the years have gone by. The first time I actually did the whole thing with full make up, shaved body, wig, painted nails, jewelry, stockings, basque, panties, high heels and not forgetting perfume was about 5 years ago.

    Lucy Lou xx

    Nadina, totally agree with that. Panties and stocking and suspenders and a short skirt. Wonderful. Lucy Lou.

  2. #552
    New Member
    Join Date
    Mar 2014
    Posts
    28
    11 years old. I was home alone and next thing I know I have on my sisters mini skirt, panty hose, bra, tank, and make up.

  3. #553
    Junior Member Tami's Avatar
    Join Date
    Mar 2014
    Location
    Uk
    Posts
    84
    First time around 18 but only occasionally. Have worn my wife's clothes when at home on my own throughout our marriage but never said anything. We have since split up for non related reasons but are good friends so I told her. I have now spent 2 evenings at her flat wearing dresses with her and am now building up to asking her to help me with make up etc, I'm sure she will be happy to help.

  4. #554
    Junior Member RachaelInLv's Avatar
    Join Date
    Mar 2012
    Location
    Las Vegas, NV
    Posts
    47
    from the age consensus I am seeing here I was definitely a late bloomer, I didn't start until I was 24 and already married to my wonderful wife.

  5. #555
    New Member
    Join Date
    Mar 2014
    Posts
    19
    I found a bag of clothes I think they could of been a crossdressers they were in some woods don't know what made me try them on bra nickes and suspender belt all in purple I put them on and loved it xx

  6. #556
    Junior Member Diana81's Avatar
    Join Date
    Mar 2014
    Location
    Canary Islands, Spain
    Posts
    64
    Fully, one month ago.

  7. #557
    New Member laceslip's Avatar
    Join Date
    Apr 2006
    Location
    sc
    Posts
    27
    Just wanted to share with you girls some thoughts I had written down on this obsession that I love!!

    Did it start with your older s****rs or mothers lingerie drawers?
    Sorting thru lace trimmed panties. Looking at hoisery drawers.
    Looking at those catalogs and the extensive lingerie sections.
    Sliding on that first pair of panties and being amazed at how they felt.
    Finding that drawer full of slips and being taken back by all that pretty lace.
    Letting a slip drop over your head and feeling it slid on your body.
    Taking some of that lingerie to your room and trying it on.
    Did you have the nerves to explore your Aunts or your neighbor ladies dresser drawers.
    Was it "borrowing" some piece of lingerie that you had to have.
    Did you end up with a collection of lingerie hidden away in your room.
    Was it when you were in a department store and walking thru the lingerie dept.
    Or when you got up the nerve to purchase your first piece of lingerie from that store.
    The first time you had the house to yourself and found yourself trying on everything.
    Piling all that pretty lingerie on the bed and writhing around on it.
    Finding an old dresser in the attic with a drawer full of vintage slips.
    The first time you wore a dress or a skirt.
    Finding yourself trying to catch a glimpse of a peek of lace under a skirt hem.
    Trying on that garter belt and a pair of stockings that was buried in your Aunt's dresser.
    When you got the nerve to get a hotel room solely for the purpose and privacy of being girlie.
    Choosing your girlfriends based on the assumption of there choice of lingerie.
    Seeing your first adult film and finding the lingerie you saw to be more provacative than the sex.
    Being in college and having a female room mate and rifiling thru there lingerie.
    Having independence as a young adult, enough to dress whenever you wanted to.
    Building a stash full of lingerie and keeping it hidden.
    Finding that niche market and buying VHS tapes of lingerie tease.
    Buying adult magazines and cutting out the best lingerie pictures and making a collage.
    Finding a pair of heels that fit and being amazed at how they made you feel.
    Hearing those heels "click" on the floor when you walked.
    Wearing a wig and perfume for the first time.
    Experimenting with make up and realizing how hard it is to make it look right.
    Having a new found appreciation of a pretty face with perfect make up.
    The first time you dressed all the way as a woman and how erotic it felt.
    How nervous you were the first time you ventured out of the house dolled up.
    Admitting to someone else that you had a "girlie" fetish.
    Putting on your prettiest lingerie, your favorite dress and heels. Perfecting your make up and getting in the car and riding all over town feeling so sexy.
    Spending an entire weekend as a woman.
    Experimenting sexually being dressed and finding out how erotic it can be.
    Spending way too much money on lingerie, clothes, make up, shoes and jewelry for yourself.
    Discovering how much the internet could be a factor in your crossdressing.
    The first time you were with another CD.
    Admitting to yourself that this was a very deep part of you and that you really loved it.

    Part two coming soon!

    I hope this brings back some fond memories for you.
    It certainly does for me!

    xxoo

    Mandy

  8. #558
    New Member cdyoung114's Avatar
    Join Date
    Mar 2014
    Posts
    12
    I remember trying on a bra around the age of 10... I didn't start buying clothes and lingerie until I was around 22

  9. #559
    Banned Read only
    Join Date
    Mar 2014
    Posts
    7
    About 9 or 10 years ago when we received an adult "toy" catalog in the mail, it came with a cute little mesh thong with some rhinestone word on the back. I tried to get my wife to try it on and model for me to no avail. After a while she told me, "if you like it so much, why don't you put it on?"
    So I did, and made a big show about it. I am pretty sure that she didn't expect that I would. She got pretty mad.

  10. #560
    Junior Member pajeantv's Avatar
    Join Date
    Feb 2014
    Posts
    42
    Wow, Crossdressing for me started early, at age 7 or 8, started when a cousin (girl) came to visit my mother for a week during the summer. she was a little older than me but was about the same size. She brought a swim suit, dresses, and shorts, tops, Mom and her went out on day and I was looking at the swim suit, started by trying that on, WOW, the went on from there, sadly Mom came home while i was still in one of the dresses, i couldnt get undressed fast enough, She flipped out on me and wooped my butt, that just reinforced that i should look like a girl as much as i could. was in my late teens till i bought any of my own stuff, just dresses, or things like that that i could get at a thrift store.

  11. #561
    Casey
    Join Date
    Dec 2009
    Location
    Dallas, TX
    Posts
    156
    Quote Originally Posted by laceslip View Post
    Just wanted to share with you girls some thoughts I had written down on this obsession that I love!!

    Did it start with your older s****rs or mothers lingerie drawers?
    Sorting thru lace trimmed panties. Looking at hoisery drawers.
    Looking at those catalogs and the extensive lingerie sections.
    Sliding on that first pair of panties and being amazed at how they felt.
    Finding that drawer full of slips and being taken back by all that pretty lace.
    Letting a slip drop over your head and feeling it slid on your body.
    Taking some of that lingerie to your room and trying it on.
    Did you have the nerves to explore your Aunts or your neighbor ladies dresser drawers.
    Was it "borrowing" some piece of lingerie that you had to have.
    Did you end up with a collection of lingerie hidden away in your room.
    Was it when you were in a department store and walking thru the lingerie dept.
    Or when you got up the nerve to purchase your first piece of lingerie from that store.
    The first time you had the house to yourself and found yourself trying on everything.
    Piling all that pretty lingerie on the bed and writhing around on it.
    Finding an old dresser in the attic with a drawer full of vintage slips.
    The first time you wore a dress or a skirt.
    Finding yourself trying to catch a glimpse of a peek of lace under a skirt hem.
    Trying on that garter belt and a pair of stockings that was buried in your Aunt's dresser.
    When you got the nerve to get a hotel room solely for the purpose and privacy of being girlie.
    Choosing your girlfriends based on the assumption of there choice of lingerie.
    Seeing your first adult film and finding the lingerie you saw to be more provacative than the sex.
    Being in college and having a female room mate and rifiling thru there lingerie.
    Having independence as a young adult, enough to dress whenever you wanted to.
    Building a stash full of lingerie and keeping it hidden.
    Finding that niche market and buying VHS tapes of lingerie tease.
    Buying adult magazines and cutting out the best lingerie pictures and making a collage.
    Finding a pair of heels that fit and being amazed at how they made you feel.
    Hearing those heels "click" on the floor when you walked.
    Wearing a wig and perfume for the first time.
    Experimenting with make up and realizing how hard it is to make it look right.
    Having a new found appreciation of a pretty face with perfect make up.
    The first time you dressed all the way as a woman and how erotic it felt.
    How nervous you were the first time you ventured out of the house dolled up.
    Admitting to someone else that you had a "girlie" fetish.
    Putting on your prettiest lingerie, your favorite dress and heels. Perfecting your make up and getting in the car and riding all over town feeling so sexy.
    Spending an entire weekend as a woman.
    Experimenting sexually being dressed and finding out how erotic it can be.
    Spending way too much money on lingerie, clothes, make up, shoes and jewelry for yourself.
    Discovering how much the internet could be a factor in your crossdressing.
    The first time you were with another CD.
    Admitting to yourself that this was a very deep part of you and that you really loved it.

    Part two coming soon!

    I hope this brings back some fond memories for you.
    It certainly does for me!

    xxoo

    Mandy
    So many of those hit home. Thanks for a few wonderful memories.

  12. #562
    Member
    Join Date
    Mar 2014
    Location
    Tasmania, Australia
    Posts
    112
    I don't know exactly how old i was, but i remember my mum demonstrating how to put socks on, by putting her pantyhose on, and generally being around her as she dressed..my dad was usually at work already.

    But my first time was when i was about 5 or 6 my friend wasn't home and the little girl next door invited me to play, she got me to put on a pretty lemon dress and buttoned me in, some adults called to her and were coming over..i left the dress on the grass and ran away cheeks burning; didn't really start wearing my mum's clothes until puberty; i knew what i liked pretty quickly. About the same age (5ish) my friend rolled me up in a carpet and i loved the feeling of restriction..tried to reproduce it. Xdressing was more a spice to being restrained since puberty.

  13. #563
    New Member
    Join Date
    Mar 2014
    Location
    The Netherlands
    Posts
    15
    My first time was when I was around 4 years old and I was wearing a pink princess gown and those fake plastic slippers from cinderella story

  14. #564
    New Member Emily43's Avatar
    Join Date
    Mar 2014
    Location
    U.K
    Posts
    25
    I used to stay at my aunties a lot when i was 7 or 8 and remember looking through her draw in the room i used to sleep in...was full of stockings and french knickers...i tried them on...the rest is history.

  15. #565
    Member Erica Grace's Avatar
    Join Date
    Mar 2014
    Location
    Southeast PA
    Posts
    125
    I think I was 12 or 13 and went through my stepmoms closet, she had so many dresses and I tried each one on. Happy to have my own now

  16. #566
    New Member Jaidyn's Avatar
    Join Date
    Aug 2012
    Location
    NC
    Posts
    20
    I remember trying on my sisters ballet suit when I barley knew how to dress myself in my own clothes.

  17. #567
    Member AprilMayy<3's Avatar
    Join Date
    Mar 2014
    Location
    Southern California
    Posts
    157
    Oh jeez, when I was about 10 or 11. Walked in the bathroom one morning during summer and my sister was drying her bras she had washed over the shower rod. She had all 4 just hanging there, and I couldn't resist :P I think that's when it started, but I only got serious with it about when I was 14 or so.

  18. #568
    Lingerie lover
    Join Date
    Oct 2013
    Location
    Waynesboro, VA
    Posts
    13
    Quote Originally Posted by laceslip View Post
    Just wanted to share with you girls some thoughts I had written down on this obsession that I love!!

    Did it start with your older s****rs or mothers lingerie drawers?
    Sorting thru lace trimmed panties. Looking at hoisery drawers.
    Looking at those catalogs and the extensive lingerie sections.
    Sliding on that first pair of panties and being amazed at how they felt.
    Finding that drawer full of slips and being taken back by all that pretty lace.
    Letting a slip drop over your head and feeling it slid on your body.
    Taking some of that lingerie to your room and trying it on.
    Did you have the nerves to explore your Aunts or your neighbor ladies dresser drawers.
    Was it "borrowing" some piece of lingerie that you had to have.
    Did you end up with a collection of lingerie hidden away in your room.
    Was it when you were in a department store and walking thru the lingerie dept.
    Or when you got up the nerve to purchase your first piece of lingerie from that store.
    The first time you had the house to yourself and found yourself trying on everything.
    Piling all that pretty lingerie on the bed and writhing around on it.
    Finding an old dresser in the attic with a drawer full of vintage slips.
    The first time you wore a dress or a skirt.
    Finding yourself trying to catch a glimpse of a peek of lace under a skirt hem.
    Trying on that garter belt and a pair of stockings that was buried in your Aunt's dresser.
    When you got the nerve to get a hotel room solely for the purpose and privacy of being girlie.
    Choosing your girlfriends based on the assumption of there choice of lingerie.
    Seeing your first adult film and finding the lingerie you saw to be more provacative than the sex.
    Being in college and having a female room mate and rifiling thru there lingerie.
    Having independence as a young adult, enough to dress whenever you wanted to.
    Building a stash full of lingerie and keeping it hidden.
    Finding that niche market and buying VHS tapes of lingerie tease.
    Buying adult magazines and cutting out the best lingerie pictures and making a collage.
    Finding a pair of heels that fit and being amazed at how they made you feel.
    Hearing those heels "click" on the floor when you walked.
    Wearing a wig and perfume for the first time.
    Experimenting with make up and realizing how hard it is to make it look right.
    Having a new found appreciation of a pretty face with perfect make up.
    The first time you dressed all the way as a woman and how erotic it felt.
    How nervous you were the first time you ventured out of the house dolled up.
    Admitting to someone else that you had a "girlie" fetish.
    Putting on your prettiest lingerie, your favorite dress and heels. Perfecting your make up and getting in the car and riding all over town feeling so sexy.
    Spending an entire weekend as a woman.
    Experimenting sexually being dressed and finding out how erotic it can be.
    Spending way too much money on lingerie, clothes, make up, shoes and jewelry for yourself.
    Discovering how much the internet could be a factor in your crossdressing.
    The first time you were with another CD.
    Admitting to yourself that this was a very deep part of you and that you really loved it.

    Part two coming soon!

    I hope this brings back some fond memories for you.
    It certainly does for me!

    xxoo

    Mandy
    A lot of this hits home for me. I was about 11 or so I guess and always looking at the lingerie section of JCPenney and Sears catalogs. I was doing household chores and gathering up the trash around the house to take out. On my Mom's side of my parents bed was a small trash can. When I went to empty it, all that was in there was a pair of pantyhose that she'd thrown away because of a run in them. I pocketed them so I could try them on later. When I was alone in my room later, I put them on an immediately became aroused. After that, when I was left home alone, I would go exploring Mom's lingerie drawers. I'd try on her bras, slips, and whatever else I could find. I'd stuff the bra cups with socks. Sometimes I'd even try on her dresses and swimsuits. I've been hooked ever since.

  19. #569
    New Member
    Join Date
    Mar 2014
    Posts
    28
    I guess somewhere when i was 8-9. I asked my cousin to paint mt nails, and put lipstick on me, it as fun

  20. #570
    New Member KayleeAnn's Avatar
    Join Date
    Mar 2014
    Location
    Michigan, USA
    Posts
    19
    I think I was 9-10, but it was just small stuff like wearing panties but as I grew up, I started getting more and more clothing and dressing more and more. I still haven't gone out in public dressed but I'm working my way there.

  21. #571
    Member
    Join Date
    Dec 2004
    Location
    Southern Arizona
    Posts
    311
    My first time crossdressed was by my mom when she was feeling playful and I wore my older sisters outgrown party dress with lace panties lacy socks and maryjanes . What I remember most was being stimulated and embarrassed both , mostly because my older sisters
    little friends saw me and laughed.

    I tried on my first bra at age 14 because a cute MILF told me I should be wearing a bra , since as she said ,my tits were bigger than hers. Again I was both embarrassed and stimulated . A week later I saw my older sisters lace underwire bra on the floor of her bedroom , being home alone I picked up the black lace underwire bra and as I was leaning forward walking my hands down the band to hook the brassirere behind my back like my mother, and felt my breasts in those lacve cups I almost feinted from the sensation.

    Then I knew I was a crossdresser , it fit me like I had been measured for it , I looked in the mirror and I had 36B breasts like a woman , and I was so excited , I decided to take it and wear it for awhile (my head was spinning) and as I was leaving her bedroom I saw the
    matching (Vassarette) LLPG with lace around the legs , so sexy and all sheer black lycra, and decided to take it too , ohh my I can still remember them .

  22. #572
    Lacy Lacyfem's Avatar
    Join Date
    Apr 2010
    Location
    Palm Springs
    Posts
    394
    I remember it like it was yesterday as it was so exciting. I was ten and parents had a cocktail party and then they all went out to dinner. There were all sorts of drinks and liquor left around and I decided to sample the booze. My Dad drank Jack Daniels so I helped myself to a nice pour of it and within a short period was feeling really good. Sexually I had already started to masturbate as an older friend had taught me and was sexually involved with my older brother. For whatever reason when I got myself drunk I dropped what I was wearing and went into my mothers hamper and put on her full cut nylon panties and her bra. She was a very full C cup so I stuffed the bras with the other panties from the hamper. I was hooked as it felt so good and being so young not sure I understood my feelings then but they were definitely sexual as well as feeling very fem. I had always loved to watch my mom dress and envious of her beautiful body and wonderful lingerie and cloths she had. There is a thread here on putting on our bras as I loved watching my mom as she would put the bra on with straps on shoulders and then lean over so her beautiful breast would hand down and she'd then pull the bra over her breasts, stand up and connect the hooks behind her back. She did it so easily and it was sexy. From this day on I was into her hamper a lot as well as other things she wore. As for that wonderful night, I got pretty drunk, did throw up and the following morning my Mom knew I had gotten sick and knew why I got sick. However, she never knew that I also started a lovely fem crossdressing career wearing her beautiful lingerie.

  23. #573
    girly girl
    Join Date
    Mar 2012
    Posts
    545
    I can't remember exactly how old I was, but I can remember that when I was young I used to feel guilty/shameful about trying on panties and other things I would find in the "dirty-clothes" hamper Mom kept in our bathroom. I can remember vowing that when I turned 10 years old I would finally quit doing it. I remember I had been doing it for years and felt it was about time I stopped. Turning an age in the double-digits seemed like a good target for quitting. Of course I never quit. If I had to guess I'd say I was 7 or 8. I don't feel guilty anymore.

  24. #574
    The best of both Worlds! Paula_Femme's Avatar
    Join Date
    Mar 2014
    Location
    La La Land, SoCal
    Posts
    305
    When I was a child - 4 or 5 maybe? - practically all the neighbor kids, and so all my friends, were girls, and I do distinctly remember wishing that I was a girl, so I'd be just like them!

    Then later - 10 to 12 is the best I can estimate - I remember trying on my Mothers shoes, and I've had a heel fetish ever since!

    The first time I seriously cross dressed was in my early 20's when my girlfriend suggested I "dress-up" while I was doing the ironing... the rest is history!!!
    Black is ALWAYS the, "New Black!"
    "I really hate it when people accuse me of wearing Womens clothes... these aren't Womens clothes... I f*****g bought them!!!" Eddie Izzard.

  25. #575
    Member wanda66's Avatar
    Join Date
    Apr 2014
    Location
    va.
    Posts
    313
    I was about 10 . I had no sisters so I got moms stuff first the panties , bra . Them I startd with the dresses, and such ..this when on untill my late teen. Mid 30's ....the wifes panties. Then I went on the road to work , away 5 days a week . I got bold and began buying my own panties and bras .getting older my pecks got a bit larger and filed my bra some. I enhance them now to a 38b... I have writen this down a 100 times on paper this will be the first time it will be read by someone.. Iam into my 60's now and if feels good to talk about how I got here. I know many of us have similar stories . I hope I'm not boring any one...thank you for the place to talk....

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