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Thread: What was your First Baby Step?

  1. #1
    Silver Member Becky Blue's Avatar
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    What was your First Baby Step?

    Reading an earlier thread about someones first baby step got me thinking, we all started somewhere and we all did something at the start of our journeys that was huge at the time. I am not talking about the first item of clothing we put on as we all did that at some stage. But the thing you did that made you stop and think OMG I just did....

    After years of CDing and always simply being a guy putting on some items of clothing, everything changed overnight. One of the first things i did was to open a yahoo email account where I selected an gender neutral email address. I can still so clearly remember hovering over gender and selecting female and then thinking wow what did I just do. Such a small step on the long road ahead that has had so many huge leaps, but at the time it felt so significant.
    A.K.A Rebecca & Bec

  2. #2
    Banned Spammer
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    About a week ago I bought a dress (its actually a disgusting dress/shorts combo) from a shop, in guy mode.
    That was a huge deal for me.
    I know I could've been buying it for my girlfriend but then most guys don't do that.

    I'm a LONG way from buying openly but it was a huge deal for me

  3. #3
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    Hi Becky
    My first big step was buying a bra and some forms online and putting them on. The rush was amazing and I stood there thinking "I have dreamt of doing this for years." Still get the same feeling.
    Vikky
    ------------------------------------------------------------------------------------------------------------

    Adventure before dementia

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    My 1st time in the womans department was traumatic! I was certain every eye was upon me!.. No matter how much I tried to convince myself I was here for my wife/girlfriend/sister, I was certain I wasn't believable. I was sure I'd be found out...or what if somebody I knew might see me in here looking at Female goods? Or some old/young Mother/Grandmother would be thinking I am some kinda pervert!
    So I started as small as possible. Scarves.They seem easy enough, right? I'd pick a time of day when the store was empty, and at least shopping wasn't a big issue. then the next hurdle...THE CHECKOUT!! EEEK!
    I'll get to that chapter on another installment! point is, I did survive, and lived to tell me tale! many many stories of this same nature to be found here...it's all ok in the end don't worry too much

  5. #5
    Aspiring Member Fiona123's Avatar
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    Buying a three pack of microfiber panties as Sam's club.

  6. #6
    Junior Member AlissaMurray's Avatar
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    I still get a rush out of shopping and I have been purchasing things from Walmart and Goodwill for years. I walked into a little 2nd hand store the other day and no one was in there except for me. I found this cute little top nylon tank top t-shirt sort of thing that I just had to have. I went through all the lady's clothes in the place and that was all I found. I will say I am a picky shopper and only like certain styles. Anyway I took the top up to the counter and handed it to the lady and she said "Oh this is cute", to which I replied "I think so too." I paid the lady and out the door I went. She could have cared less who I was buying for as long as I bought something. It was still a rush after all these years. I actually work at Walmart third shift stocking dairy so I am pretty well known in the place now. There are days I have real issues because something will catch my eye as I am walking through the store but I don't want to get busted by my co-workers checking it out. LOL Ahh the trials of being a closet crossdresser.

  7. #7
    Stand-up Comedian En Fem❤ Alice_2014_B's Avatar
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    For me it was going to a department store all dolled up in heels.
    I would say that actually interacting with people en femme (I never disguise my voice) was one, but that was a major step for me.
    Melissa: "... and why are you dressed as a woman?"
    Coach McGuirk: "Because it's freeing."

    -Home Movies
    (cartoon series)

    Shoe size: 9 US women's.
    Dress size: M to L; 8-10.
    Height: 5' 6".

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    Great experience

    I too was man dressed yesterday but went to do some shopping and bought a a bikini and tank top and tights and dress. I was not the slightest bit nervous. Good job too as the shop assistant looked at her colleague with eyes rolling as much as to say "shameless!!" I acted perfectly normal as if I was buying a sandwich. Then guess what!! The checkout till got stuck half way through the transaction and she had to call the manager drawing everyone's attention to my purchase.But I was unphased.lol.and I just weathered the storm.
    Enjoy your shopping sweetheart.

  9. #9
    Aspiring Member Lacey New's Avatar
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    My first purchase was by mail. I had a Macy' charge card and in the bill was a little flier for panties. I filled it out and sent it in with the bill. About two weeks later, six pairs of panties came in the mail. I was in heaven. My first "live" purchase came a few years later. i was starting a lengthy road trip and I stopped at a mall on the way and hit the JC Penneys store. I purchased a pair of nylon hipster panties, a pair of pantyhose and my first bra. When I paid, my mouth was so dry, i could barely talk and i am sure my hands were shaking when I handed over the cash. I missed the size of the bra and it was a little tight for extended wear but I chalked that up to a learning experience. But, I did not get arrested as I left the store and guessed that a man buying lingerie was not illegal. And, since the woman at the checkout counter did not seem to care, I knew that I could probably buy more lingerie and "get away with it". I've been "getting away with it" for years since. And I still love buying lingerie.

  10. #10
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    For me it is buying shoes. I scope them out with one or two fly buys and then when I want them so bad I get up the nerve to buy them. But what a rush leaving the store.

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    Buying and wearing Madewell socks.

  12. #12
    Gold Member alwayshave's Avatar
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    Mine was in my late teens or early twenties walking into a long gone local department store and buying a matching bra, panties and slip. Baby blue. Guessed at the size but got it right. I loved that outfit. I'm not sure what happened to it at this point, so long ago. But then I knew.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  13. #13
    Senior Member NancySue's Avatar
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    Nervously buying my first pair of pantyhose. The SA was very helpful. Looking back, I'm now convinced she suspected or knew they weren't for my wife. She'd run her hand in the samples to show me how they'd look against skin. She told me she also wore Hanes and showed me her calf encased in Barely There pantyhose. I know my face was red and probably confirmed her thoughts. Guess what is my favorite color hose? I've come a long way. While I buy a lot on line, it's still fun to go out and buy in person. 99% of the SA's don't care.

  14. #14
    Senior Member Jennifer in CO's Avatar
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    my "I knew" time was Halloween when I was 11. I had spent 3 weeks of that past summer with my Aunt who "created" Jennifer. I had fun wearing girls clothes and wanted more (driving my Mom crazy for a couple of months). So when I asked to "be a girl" for Trick or Treat she relented (she did have ulterior motives). I wore a short maroon velvet dress of my Sisters' that was short enough it has a matching panty cover. She bought me my own panties and hose because of size but she found an old padded bra of my Sisters to add in. I had hair that touched my shoulders at the time and it was wet set, light makeup and finger and toes painted a similar maroon. Shoes were a pair of Sis's go-go boots. T-or-T was fun but I had a party to go to after (not real late - it as something like 7-10 or something like that) and got home quickly so I could change and go there. Well, Mom said she couldn't find her makeup remover OR the fingernail polish remover so I'd have to go as a boy in makeup or dressed as I was. So I went dressed as I was.
    It was a big party with grownups as well as kids at an old neighbors house. I had played with the boy for years before we moved so it had been a while since I had seen him or his family. He almost didn't recognize me. His sister didn't. His Mom thought I was cute. Mark spread the word as he introduced me to his other friends that I was a boy and nothing more was said. I played with the others (most of the time the girls if we split up) the rest of the evening and no one said or cared. With the exception of his parents, not a grownup one indicated I was anything other than a girl at the party. One of the other girls parents lived not too far from our new house and even took me home saying that "we girls" should get together and have a sleep over sometime (didn't happen). When I got home Mom had "found" her makeup remover but no fingernail polish remover. So I wore maroon nails (and shaped eyebrows) to school the next day, the day after then that night she "found" her polish remover. I also didn't wash my hair till that Sunday morning to wash out the curls.
    At school as I remember no one said anything about my hair, nails or eyebrows. Well, they may have, but I don't remember. After that, "I knew" this was what I wanted. It wasn't till I was 14/15 that I had a solid taste of what I could have.

  15. #15
    Stop that, it's silly.... DIANEF's Avatar
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    My first step was getting my first wig. There was a shop selling stuff for CDers not far from where I lived. I longed to go there as a wig was the final piece of the jigsaw for my 'look'. I went several times, always chickening out at the final moment, even got as far as getting my hand on the door handle. Always went away feeling disappointed, for not getting what I wanted but mainly in myself for being such a wuss. Anyhoo, one day I steeled myself and walked through the door, and the staff there were amazing. They took plenty of time helping me choose what I needed, gave me coffee, asked about by clothing style, I was on such a high as I left. And when I got home and got to try the wig, wow, a life changing moment.
    Here today, gone tomorrow....

  16. #16
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    Sounds ridiculous but working out that filling a normal balloon so it's just over taught felt so much more natural in the bra than stuffing in socks

    In a satin push up bra it really felt right next to the small cleavage it helped create and the tie up of the balloon made a lovely looking/feeling nipple

  17. #17
    Platinum Member Teresa's Avatar
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    Becky,
    It's a difficult question, I think my answer would be putting on a baby doll nightie set at my GFs home and taking the chance on her reaction when she pulled the covers back ! All I will say is it went WELL !!

    More recently was probably when I joined the forum, the whole sequence of events. Joining meant accepting I was a CDer, then accepting a female name and finally my first avatar . Maybe showing the World what I looked like as Teresa was the big one !! We mustn't forget the whole World can see us, initially that thought is scary !

  18. #18
    Gold Member Lana Mae's Avatar
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    Seeing Lana Mae for the first time at my transformation pulled it all together for me! My avatar picture was that first look! I was almost in shock and happiness that I can't describe! Hugs Lana Mae
    Life is worth living!
    "Foxy lady! You look so good!!" Jimi Hendrix

  19. #19
    Member Gabby6790's Avatar
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    I think joining this forum is an easy one. It helped understand and accept myself for being CD and not just a guy with a fetish for women's clothes.

    After that, I think it was probably when I went out fully dressed. Heels, bewbs, wig, etc. I don't think I had makeup on and I only drove around and walked around some abandonded parking lots but it is difficult to describe the feeling of happiness, peace, exhiliration.

  20. #20
    Gold Member Alice B's Avatar
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    Like many my first step was dressing for Halloween and the hook was instantly set. Joined this site right after on reccomendation of a friend and it was a very big help. First items were panties and quickly folloed by a bra, forms, wig and dress. A never ending process.

  21. #21
    Silver Member Sometimes Steffi's Avatar
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    I had lots of "baby steps". Getting my very own Sears catalog. Mail order from the Sears catalog. Drive by shopping for lingerie, you know, when you just grab the first thing that you touch and take it to the register. Like the Flash, so fast no one saw you doing it.

    But what was much more memorable was my first "giant step". I went to the Maryland Renaissance Festival and rented a "wench costume" consisting of a long linen skirt, a white chemise and a tapestry waist cincher

    http://www.rennfest.com/general-info...ostume-rentals

    and spending the rest of the day en femme.

    My makeup was awful, I used home-made foam breast forms, I had no wig and used a scarf over my head instead, and it was so wonderful to be a girl for a day. I'll never forget that day.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

    Gender fluid (adj.) - Describes a person whose gender identity is not fixed. A person who is gender fluid may always feel like a mix of the two traditional genders, but may feel [more] like one gender some days, and [more like] another gender other days.

    Ref: https://www.lgbthealtheducation.org/wp-content/uploads/LGBT-Glossary_March2016.pdf

  22. #22
    Member Randee's Avatar
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    Actual first step was buying first long sleeve black leotard and tights at Sears. After getting through the nerves of doing that a couple of times, the next baby step was coming up with a reason to go into dance wear store and buy a turtleneck leotard and tights for a costume for myself, and trying them on in the store in front of sales lady and other customers. The sales lady very pleasantly helped me with the back zipper bothe putting them on and taking them off at my request. This led to the the major step of wearing leotards and tights as part of Halloween costume to party among friends. Following through with that gave me a reason to keep such garments in my clothes drawers with the other things.
    Last edited by Randee; 04-20-2017 at 01:19 AM.

  23. #23
    Silver Member Sometimes Steffi's Avatar
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    I was embarrassed to mention it, but my first retail purchase was a couple of leotards and tights from Sears also. Burgundy and navy blue.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

    Gender fluid (adj.) - Describes a person whose gender identity is not fixed. A person who is gender fluid may always feel like a mix of the two traditional genders, but may feel [more] like one gender some days, and [more like] another gender other days.

    Ref: https://www.lgbthealtheducation.org/wp-content/uploads/LGBT-Glossary_March2016.pdf

  24. #24
    AKA Lexi sometimes_miss's Avatar
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    I didn't understand it at the time; I was, what, 11, 12 years old? For several years, someone else was providing the girl clothes for me to wear. But I was starting to grow too tall to wear those any longer; his sisters weren't tall girls. So I guess it was the first time I put together an outfit of my older sister's old clothes and created a cute female outfit for myself, with the intentions of it helping me to self identify myself as a female. It was a major step of admitting to myself that I saw myself as a girl, not a boy, and that from that moment on, it was when I was dressed as a boy that I felt I was crossdressed. Poor sis would grow to be six feet tall, and would unwittingly be providing me with plenty of 'last years styles' of hand-me-downs for me to wear all the way through high school.
    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.

  25. #25
    Aspiring Member JeanetteX's Avatar
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    Hi Becky, for me it must have been the first time I ordered a pair of stockings and a babydoll through a shopping catalogue (the internet wasn't there yet at the time). I had just moved out from my parents house and I can remember that after placing the order I was almost shaking LOL and thinking 'OMG this is it, I have really done it...but what the hell have I really done?'. I was so nervous until the postman delivered the stuff at my home. I tried it on and that was it....the journey had really begun! No more 'borrowing' from mum LOL
    Love and hugs Jeanette

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