What was your First Baby Step?

[Becky Blue]

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.

[SometimesKairi]

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

[Tama]

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

[Alisonforme]

A first baby step toward what?
First step realizing I had a female side: seeing me in the mirror the first time with wig and makeup. What an experience!
First step toward fully accepting it (which was pretty much immediate): telling my wife.
First step being sort of "out" about it: probably posting face pics on this site.

[Becky Blue]

A first baby step toward what?

Good question Alison, what I was asking was what was something perhaps that you did that now you look back and think wow such a small step seemed so huge at that time. My example was selecting gender as female when creating a yahoo email address. To think that 4 months later I was walking up Oxford Street in the heart of Sydney fully dressed makes the email setup seem like such a tiny step, but it was so significant at the time.

[Stephanie47]

When my wife and I were first married we dabbled in some "kinky bedroom play." I had a fondness for nylon which originated with trying on my mother's nylon slips. She use to hang them in the sole bathroom of our apartment to dry. I love the feel of nylon which was unlike any boy clothes I wore. My wife found me sipping water one night in the kitchen wearing one of her nylon floor length peignoirs. She asked why I was wearing it. I told her I like the feel of the nylon. We did some shopping together for nighties for me. We ended up with a pink knee length peignoir, a black floor length gown, and, she gave me a red knee length castoff she did not really like. She bought me some stockings and a garter belt too. That was before our first child was born.

When our child was four months old she took him across country to meet her family. I was left alone for a week. I decided to go shopping in mid town Manhattan on 34th Street where I bought my first dress. I guessed right as to the size..a 12. Back then I wore a 38 Tall suit and had a 32 inch waist. My old military physique. I wore that dress at home until the day before she got home from her trip. I threw it away because I did not want her to discover my desires were advancing.

It wasn't until more than a decade later and 3,000 miles away from NYC that I bought my first dress to keep. It was hit and miss, and, mostly miss as to guessing sizes and fit. Now? Well, I have a word document which lists all my dresses (157 and counting) with pictures downloaded from eBay or retailers such as JC Penny, Fred Meyer, Sears, Macy's, etc.

That first dress was a big deal considering it was 1975 and cross dressing was not at all main stream.

[Vikky]

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

[daenna]

First time out fully dressed was an evening car ride ... I was sure everyone was looking at me, but nobody seemed to notice.

[Fiona123]

Buying a three pack of microfiber panties as Sam's club.

[AlissaMurray]

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.

[Girlina]

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.

[JustJoni]

For me I guess it wasn't a baby step per se, but it was exactly as Becky stated: wow, what did I just do.

I had full disclosure to my fiance before we were married, and she was/is wonderfully supportive. By the time we were married I had dressed some around her but only at home. On our honeymoon she wanted us to go to a gay club on out second-to-last night with me dressed. I had never (and I mean never) shared Joni with anyone but her, and I was petrified to even step into the hotel hallway, much less take the elevator down. The club was just a couple of blocks away, and rather than drive, we were gong to walk so we could have a couple of drinks. Stepping outside for the first time...wow, what did I just do, LOL

[Dana44]

First baby steps was being born. LOL I knew I was different as a we kid. But it was hose for me. and then panties and well it became a runaway train.

[Amelie]

Only as I look back on my life can I see what was the first big deal in my life, I didn't think so much at the time.

My first step was going to a night club in NYC called GG Barnums. I bought a skirt from a guy selling clothes on the street, I think I should have washed the skirt first but didn't know how, I didn't want to risk shrinking it. I bought this powder style make up in wild colors. This was the first time I dressed up and it was the first time I went out dressed. I was kinda gay at the time so I didn't think I changed myself all that much, maybe I felt I was being a bit camp. But from that day on I became more and more a woman and less and less gay, if that makes any sense. But one thing, that night ended badly for me in a hotel room but it didn't deter me from becoming who I am today.

[Alice_2014_B]

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.

[Megan Nicole]

Made my first over the counter purchase when I was in college. Leggs Shear Energy panty hose from Walmart. That was way before self checkout. Hard to do, but got it done. Didn't stop buying after that. -Meg

[Lacey New]

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.

[Ellie Summer]

I was out shoe shopping in guy mode one day, and an employee asked me if I was buying a gift for someone. The old me would have sheepishly said yes and tried to get away from the conversation, but I sucked it up and just said "Nope" with a smile. Baby step for sure, but it was a leap for me because it was the first time I was owning it and not being ashamed that I was a man buying shoes from the fun side of the store.

[Victoriafoxxtv]

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.

[rockerreds]

Buying and wearing Madewell socks.

[alwayshave]

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.

[NancySue]

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.

[Jennifer in CO]

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.

[Girlina]

Yes buying online takes the embarrassment out of the purchase unless like me you live alone. Recently I ordered a pair of "crotchless," bikini panties with a pearl string under. And my regular post man came. Couldn't get the package through the letter box and have it to my neighbour who handed it to me. I looked at the customs declaration and the description of contents in bold print "Large/red crotchless panties" /Lingerie. On the package. He never said anything but next time he saw new he gave me a wry smile and wink. I would have given a penny for his thoughts. Lol

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Good for you😁 although self checkout has it's risks. Here in the uk they sometimes have articles that for some reason end up with the wrong bar code on and you scan the item and place it in the bagging area and the computer kicks in and announces almost in a shout"UNEXPECTED ITEM IN BAGGING AREA!!!" which then means an assistant (usually female) has to take the item and have a conference and return and manually process it. By this time the "blusher" that you bought is now surplus to requirements. Lol.

[Sometimes Steffi]

They say when you hear hoof beats think horses not zebras.

He thinks you have a totally hot girlfriend that's willing to wear crotchless panties for you.

He doesn't have to know that the "girlfriend" and you are one in the same.

And if he were to say anything to you, you can just say, "I don't think you can handle the truth", or "She looked so hot wearing it" or some other double entendre that is both true and misleading at the same time.