What was your First Baby Step?

[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!
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.

[TrishaTX]

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

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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.

[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.