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

[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

[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

[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.

[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.
:)

[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.

[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.

[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.

[DIANEF]

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.

[Tamsin Secret]

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:heehee:

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 :o

[Teresa]

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 !

[Lana Mae]

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

[Gabby6790]

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.

[Alice B]

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.

[Sometimes Steffi]

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-information/costume-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.

[Randee]

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.

[Sometimes Steffi]

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.

[sometimes_miss]

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.

[JeanetteX]

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

[BrendaPDX]

The first time I put on a dress that fit. I bought it from the Goodwill, it had a side zipper. I just stood in front of the mirror thinking, is that me? I liked what I saw.

[Ressie]

My first attempt at applying eyeliner in 1974. I liked it!

[daenna]

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

[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!:daydreaming:
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.

[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.

[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

[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

[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.

[TrishaLake]

The wig, it made the dressing complete...

[OCCarly]

First real baby step? Wearing women's skinny jeans (a skintight pair from American Eagle) in public. I went with my wife to a "gourmet fast food" place for a sit down meal. I got one dirty look from an old lady in the parking lot, but everything was fine other than that.

[Bronydash]

for me it was wearing my big sisters leotard from when she was a cheerleader

[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.

[kayegirl]

I had been playing dress up for some time, usually at a friends house, 4 girls wow what a dress up box they had. But the first real step, and I still remember the feeling, was one saturday, summers evening, parents out, siblings out. I went into my older sister's bedroom, we were a similar size, and dressed fully. That is panties, bra, underskirt, a brown dress and white cardigan, white knee high socks and sandal shoes with a small heel. No make up or wig and with an obviously boy "short back and sides" hair cut, I nervously walked out of the house, by the back door, out of the garden, along the back street, then back along the front street and into the house by the front door, total distance not much more than 200yards. It felt so good that I immediately went out again, this time venturing a little further. I honestly cannot remember if anybody saw me, but given that we lived close to the town centre, and on a street of terraced houses with no real front gardens, I suppose somebody must have done. But I was almost in a trance, and oblivious to my surroundings, oh the innocence of youth!. Saturday nights were never the same after that, although it was many years after that I could be really open about my dressing.

[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

- - - Updated - - -

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.

[Girlina]

Like how you think!

[Tina Post]

Wearing my Girl Friends lingerie and cloths that she would leave at my apartment, unfortunately, I never did try and tell her, but she was probably, the only significant other that I have ever had that would have understoo

It all started one night while sitting on the couch and she said, "why don't you try walking around in those heels for a while", well I did, just for fun in front of her, well, the Earth Moved.

[Morion]

A bra, briefs and nightie. Since I believed it was just an impulse that would go away once I finally did it, I bought items that were on special. REALLY ugly!

[njcddresser]

For me it was going to work for Halloween a few years ago. I knew inside I was a CD. It I was in the closet and didn't really know what it
All meant. After that event I came out to myself and my wife.

Since then I have come to understand that I am much more than a cd and a big part of me is
Very
Feminine. I've become
Very happy with who I am

[Sarah Doepner]

Like others who have already posted, I look back on multiple "baby steps". I define them as being that moment where the decision seemed extreme at the time and in the moment was considered as a step I'd never want to take again. Then I'd move beyond it.

So several of the firsts, including getting caught and dressing again weren't baby steps, I was committed to continuing my crossdressing. I think the events that fit this are those where I moved more into contact with others. I had photos and sent them to someone I'd been exchanging email with for an assessment. I still remember one comment, "get rid of the white purse." It was good advice. I vowed to never share another photo or see anyone in the future. Then I eventually posted a photo here. I left my motel room, arrived at a place where I would meet others and chickened out, returned to my room, changed back to guy mode and returned to the meeting, just in time for them to be leaving. One went with me back to my room where I dressed and went out. Fewer baby steps these days, but occasionally I do something a little challenging and say "Never again." Except now I'm usually confident that I'll not only do it again but I'll do it better. Because that's what baby steps are for, learning to walk.