I'll always remember the first time that I........

[CarlaWestin]

In the genre of crossdressing, what's your fondest memory of a milestone or, a turning point or, when you started something that you were a little leery of but now enjoy frequently.
I guess this could also include the unfortunate unpleasantries that accompany this lifestyle.

After I see a few, I'll add my own experiences.

[Fiona123]

There are more than one. Wearing a lace cup underwire bra. Painting my fingernails. 🌺

[ClaudineD]

Out and about at 17 and first shopping trip with my Aunt.........

[BLUE ORCHID]

Hi Carla :hugs:, I think that getting my first set of foam breast forms from the
Montgomery Wards Catalog store about 45yrs. ago...:daydreaming:...

[CarlaWestin]

Hi Blue, how's Balt-y-more, Hon? Bought my first bra at Montgomery Ward in the 60's.

[Teresa]

Carla,
I'll miss out the starting point which is too mixed up to go into now.

Turning points , there have been a few, I think borrowing my GFs negligee set and falling asleep only to be woken by a totally turned on GF when she found me wearing it !

Getting my first full set of matching underwear ( Charnos ) with stockings and putting them on for the first time, which lead onto buying my first pair of heels !

Different sort of turning point, finally getting answers to my CDing, through counselling.

Final and most recent, putting it all together and walking out the door dressed and madeup to meet other CDers socially .

Carla,
I can't wait for your answer !

[MarciManseau]

Wearing my sister's pink panties for the first time, at about age 8

The first time I pleased a boy as a teen.

First time going out fully dressed in a cute skirt and top with sheer stockings, heels, and.... no panties. The thrill of doing dangerous things, I guess

[Lori Kurtz]

I was about 12 years old, alone in my bedroom, wearing my ordinary male bluejeans, a bra of my mother's stuffed with socks, and a stretchy top of my mother's. I was on my bed, rubbing my "breasts" against a pillow, and moving my body rhythmically on the mattress. The more I did it, the better it felt, until it suddenly felt way way way better, and there was a pulsing sensation down there. It was a pleasure I had never felt before, but so intense, and leaving me with such an uncomfortable feeling, that it made me afraid that I had somehow damaged my body. And, I discovered, there was a smelly mess to clean up. I had no idea that was going to happen. I was scared enough to say to myself, "I need to make sure that never happens again." Of course, I got over that feeling, and it did happen again. But the first time was unforgettable.

[NicoleScott]

It was the first time I achieved the look I had been seeking. Looking into the mirror, it was an "oh my!" moment I'll always remember.

[Kate Simmons]

The first time I went to a TG Org meeting. It was quite the adventure. :battingeyelashes::)

[CynthiaD]

First time fully en femme: 7th grade, using clothes borrowed from my mother, and rolled up socks for forms. That was 55 years ago.

[Ressie]

getting into a dress

[Yoshisaur]

Putting on my first wig and seeing what a huge difference it made.

[Amy Fakley]

oh there's more than a few, but maybe the single most memorable moment for me was trying on my first lace front wig.
I think that was the point at which I finally looked in the mirror and said "well hello there, girl!"

there's just something about realistic hair that flips a light on in my brain I guess. It's not that I don't feel girly without good hair, but I can't really see it, otherwise.

[Sarah Doepner]

I'll always remember the first time I took a walk that wasn't limited to the back yard or to the motel ice machine, but exposed me to a wide range of people. I was frightened, several parts of my outfit were failing and I realized my fashion sense was terrible. As I returned to my room I vowed to never go out again, but once I got there and fixed all the things that had me worried I went out again that night and enjoyed the rest of the evening.

[OCCarly]

The first time I ordered bikinis from Victoria's Secret. And the first time I went swimming in my pool in a two piece bikini.

[Jennifer in CO]

what I remember most was when I was early in transition and the first time I ran down a flite of stairs and my lil breasts were bouncing...AND IT HURT! Bras became mandatory after that.

[carhill2mn]

There are more than a few such moments. One in particular was when I was leaving a support group meeting on a winter night and I could hear my heels clicking on the sidewalk and feel the breeze blowing my skirt!

[BrendaPDX]

I remember the first time I put on makeup and a wig and looked at myself in the mirror. I couldn't believe it was me, I couldn't recognize myself. I wish I took a picture.

[Jenniferathome]

Easy. Hands down it was putting on my first dress at 12 or 13 years old. I actually questioned if putting on a dress would MAKE me gay! :doh: It didn't.

[Petra1]

Ordering my first piece of female clothing, a tank dress, over the phone. Talk about nervous.

[Rachael Leigh]

I think mine was that first public outing when at a party I went as a French Maid, it was the first time I did my own makeup.
I had fun with it and then I knew this can be fun it doesn't have to be hidden

[Pat]

So many firsts. First dress, first boobs, first wig. But the one that knocks them all down is the first time I saw her in the mirror. Up to that point I could tell myself anything to convince myself this was just a harmless kink that I could take or leave, but after that day I knew she had been in there the whole time and I needed to go free her. ;)

[Piora]

"I'll always remember the first time that I........"

......dressed fully for the first time. Up until I first joined this site, I strictly was a "underwear" CD. That is, ONLY corsets/garter belts, panties, stockings etc. After some encouragement from some members here, I bought skirts and some tops. I was quite surprised at what I looked like in the mirror. Since then, I dress pretty much that way all the time now. It was a turning point for me.

[iGenny]

My biggest milestone was buying and then wearing my first wig. To me, doing that meant I was committed to dressing up.

[Robin414]

I have few that happened within a few months of each other:

the first time I bought a wig when the SA asked if it was 'for me' and I said...'Yes!' 😓

Scheduling a private makeup consultation at MAC (at the advice the the wig shop SA) 🙂

First thing I bought from Long Tall Sally when I realized the SA entered my name on the receipt as 'Miss Robin...' 😊

Having the SA at Long Tall Sally ask 'if I'd like to try it on' 😀

[Diane Smith]

The first time I got acrylic nails. It was the summer of 1997, and I was mainly just curious about what it felt like to wear them and how the process was done in the salon. I was also challenging myself to step out of my comfort zone and boldly make an appointment for a clearly feminine service where I would be seen by others. I figured I would take them off after a couple of days. It's 19 years later now and I'm still wearing them 24/7.

- Diane

[lingerieLiz]

"I'll always remember the first time that I........" Well first time my mother put me in my sisters panties. Other firsts, dress, bra, panties, ... garter belt with nylons. Going out as a girl and shopping (all back in the late 50s and early 60s.

Probably the biggest event of all was my first date with a guy. It wasn't really a date but I went as a date with a friend on a dare. We had a lot of fun and played the roles several times. We were never romantic and had no sexual attraction to each other.

[Liz57]

"I remember the first time that I ever"...stole my teachers panties!

He was so mad. Sorry, only kidding. I just couldn't resist. I guess I have strange sense of humor.

Seriously, I think it would have to be the first time I tried on heels in a shoe store. I've bought other items of women's clothing but that was the first time I ever tried something on and left no doubt as to who it was for.

[Rosemary+]

Thanks Carla,
What's a great thread.
My turning point was joining this site and communicating online.
Now to get out and meet my new girlfriends enfemme

[NewBrendaLee]

Mine was putting on a bra for the first time and wishing that I had real breasts

[Lacey New]

Buying my first panties. I had a Macy's charge card and they sent the bill through the mail and enclosed an advertisement for Pam panties - nice lace trimmed nylon briefs and hipsters. The advertisement gave the option to fill out the back of the advertisement selecting size and colors and returning it in the payment envelope. I said "what the heck" and filled it out. About 2 weeks later, two small boxes appeared in my mailbox. My hands were shaking as I took those boxes up to my apartment and immediately changed into my new panties. I wore them under my jeans that evening while I went out grocery shopping and I was certain that everyone had x-ray vision and could tell I was wearing panties. I was equally sure that the Panty Police would be pounding on my door at midnight demanding to see my concealed panty permit.

[SamanthaLouiseScott]

Too many landmarks to mention and too many to list but probably the biggest for me was my first wig. It was a good quality one that I had fitted in shop. ( took a lot of bottle, we are talking early 80's )

When i went home and got fully dressed Sam wearing a faceful of make up disappeared and Samantha appeared properly.

[Helen 2]

Mom taking me out for the first time to buy my first heels.......
1965, completely en femme from head to toe, Mom's stern warnings in the car to 'keep my knees very close together because the attendant was sure to try to peek up my skirt to catch a glimpse of stocking tops and my girdle'...seeing my legs in the mirror for the first time in MY OWN HEELS....

As with all of us, there were many 'firsts' but for some reason, this I can play back in slow motion as vividly as it happened
Sigh.....

[CarlaWestin]

Carla,
I can't wait for your answer !

Well, here it is, Honey.


There are more than a few such moments.

Carole, a wonderful first for me was when the internet opened up and I saw there were people just like me that had accepted their true selves. That was way back on Filterpost where I met you and others that were just like me. Thank you.


So many firsts. First dress, first boobs, first wig. But the one that knocks them all down is the first time I saw her in the mirror.

Yes.


Thanks Carla,
What a great thread.


Thank you.


Mom taking me out for the first time to buy my first heels.......
1965, completely en femme from head to toe, Mom's stern warnings in the car to 'keep my knees very close together because the attendant was sure to try to peek up my skirt to catch a glimpse of stocking tops and my girdle.......

My goodness! What a dream way of growing up. I've so fantasized about a domineering mother forcing femininity. I just got the domineering mother part. :straightface:

Yes. Yes. There were many firsts. But, I'm so damn old I can barely remember them.
But, last November when my loving Wife was away, I made an appointment with Amy for my first professional makeup application. She did all of her fabulous procedures with tape to pull the old skin tight and a waxy substance to flatten the brows into a more desireable palette and amazing eyelashes. She even told me to keep my knees together and my hands in my lap as I was slouching like a man. All done, she fluffed out my wig and turned me around to look in the mirror.

Nearly brought to tears at what I saw, all I could say was, "Hello Carla. Nice to finally meet you. Where've you been?"

262490

[Teresa]

Carla,
That's really great I'm glad you enjoyed it , she did a fantastic job !

Now where's the stuff you're still hiding , Carla has some wonderful outfits you must have some stories to go with them !

[Gretchen_To_Be]

The first time I shaved my legs, donned a pair of pantyhose, zipped up my dress, and stepped into a pair of heels--all of which I had purchased for myself. Such an amazing feeling.

[Ressie]

I remember buying pantyhose from a hotel vending machine 35 years ago. Never repeated that experience!

[LeotardMan]

I think for me it was trying on one of my Mom's leotards for the first time. It was ALWAYS appealing seeing her or other ladies on exercise videos have them on. One day after school, I took the plunge and never looked back.

[paintmepink]

Kissed a girl. Now I think she's gross

[Joyce Swindell]

Nice Thread!!! I've enjoyed reading most of them! I have to go right now but will return and complete reading them. One quick memory to share...I was probably about 8 years old and I had the house to myself. Mom had a light green baby doll nightie that had several layers of sheer material. I remember putting it on (panties also) and going down in the garage and riding my bike in circles ...worrying the doors may open any time.

[Traci H]

One experience that sticks in my mind was the first wig I bought. I was traveling on business and had researched a shop that was in the area and cd friendly. I mustered up the courage and went and bought a wig. This still is the only time I have told an SA that the purchase was for me....obviously.

I remember how I looked and thinking how much I looked like my mother! The experience was quite a rush.

[Amy Lynn3]

Like many here I am old enough to have more than one first, however, the last one of the first was a professional makeover. When it was completed I looked into the mirror and I saw my sister looking back at me. It was very emotional for me, because I had lost my older sister, prior to that. The results of that makeover can be seen in my Avatar.

[CarlaWestin]

Traci H. Do you realize that your first post here is in a thread about firsts?
Nice start. And, welcome!

[Erin Lafleur]

Tried on one of my mother's satin slips, and panties and stockings. I was five or six years old and little did I know how much pleasure that one event would bring to my life!

[MonctonGirl]

For sure my first trip out with a GG & pro makeup - so nervous.

[Samantha_Marie]

The first time I got dressed and went for a drive. (driving in heels is way different, but fun!)

[Jenny22]

>>> 1965, completely en femme from head to toe, Mom's stern warnings in the car to 'keep my knees very close together because the attendant was sure to try to peek up my skirt to catch a glimpse of stocking tops and my girdle'...seeing my legs in the mirror for the first time in MY OWN HEELS....


Hi. Helen. Can you share with us how and why your mom was so helpful at an apparent early age? Sounds really interesting!

[Dana44]

Here in Texas we always have a good wind. I was on the ranch and had skirt on and walking out to the front gate. The wind was blowing my skirt around pretty heavy and it felt awesome. Goodness that was the first time I knew what a girl feels like wearing a skirt.

[jacques]

my milestone - when I first went shopping to buy my own clothes
luv J

[Megan b]

Two first come to mind for me. One is right after I bought my first wig. I began to transform myself as far as I could go. Then my wife did my makeup and applied my wig. It was the first time that could see a woman looking back from the mirror at me. I almost started the cry but I didn't want too mess anything up. It was awesome. The second thing that stands out too me is the first time I ever went out as Megan by myself. I went out on a Sunday night after church. Nice top, skirt, hose and heels. All it was, was just a trip to wal-mart. Scariest thing and funnest thing I had ever done. I thought everyone could/would look at me and just know but I did it anyway and just loved it. I was hooked after that although it would be about three years before I would do it again. Now it's no big deal I do all the time but I still remember with fondness that first time out.

[Judy-Somthing]

I've been cross-dressing for 50 years and when the internet came around I like most looked at nude and non-nude photos of women.

Even know I love dressing up as a women I stayed far away from anything related to cross-dressing, I'm not sure why!

But last December I felt I needed to improve my makeup skills so I felt I needed to see what other cross-dressers were doing.

That's when I found this site and I'm glad I joined!

[sara66]

the first time I put one pantyhose. The best thing ever. One of my favorite things about dressing to this day.
Also the first time I bought a bra, thought my heart beat could be heard by any one within 50 feet of me.
Sara

[Lee Andrews]

Two milestones for me. First was being a young fella, looking at all my moms bra's, slips, panties and hose and having an unreal desire to try them on. Fought it for weeks but finally caved and here I am today.
Second was the Internet, with which I found out I wasn't alone. As a kid I thought only gay people did this but I wasn't , so why did I? Still don't understand why but I have come to grips with it. I was pretty messed up trying to cope. Thank god for Al Gore or I'd still be messed up. ;)

[Lori Kurtz]

Thank god for Al Gore or I'd still be messed up.)

Huh? Do you know something about Al Gore that I don't? You've got me curious ... Am I the only one not to understand this reference? Please pardon my dense-ness, if that's what it is ... but can you help me get what I'm missing? Thanks!

[stlmichelle]

Probably the first time I slid a pair of pantyhose up my legs. I had found myself drawn to them at a very young age, but the feeling that a pair of pantyhose give for the very first time is more intoxicating and addictive than any drug.

[Pat]

... but can you help me get what I'm missing? Thanks!

The meme is that Al Gore invented the Internet. ;)

[Jane G]

Without doubt the first time I walked out of a department store with a bag full of girlie stuff, just for me. Such a guilty pleasure and never to be forgotten.

[Kathy Smith]

Oh, which one?

Probably my first wig, bought on a market stall (nervously - and wondering if all wig sales are recorded...).
I'd hung a cheap mirror on the back of a bedroom door and the face that looked back at me was Kathy's. That was amazing. :)

My other choice would be my first pair of silicone forms. Not exactly the highest quality, but the difference they made to me was astounding (although I suspect some of that might have been in my imagination. lol

[Lori Kurtz]

... Al Gore invented the Internet. ;)

Ah ... cute ... :) ... Thank you, Jennie.

[Angela010]

The first time trying on dresses in a store. I browsed for ages before I finally admitted to the SA that I was looking for items for me. She was wonderful.

Then, just last week going out to the theatre with a GG fully dressed for the first time. It was such a good night.

[ClosetED]

Like others, the first time I looked in the mirror with wig and makeup and saw the woman I only dreamed of magically turning into.
I also recall the one time, during college, of going out in public, to a movie. I passed as far as I know, but so scary I did not try again.
Hugs, Ellen

[Elizabeth G]

These have been a lot of firsts for me but the feeling I got the very first time I walked out the door fully en femme was probably the most terrifying and simultaneously exhilarating feeling I have ever had in my life.

Beth

[rachael.davis]

The meme is that Al Gore invented the Internet. ;)

If you look close at those brows he may have had ulterior motives :)

[ChristaB]

I had dabbled in trying to put on make-up a few times, never with success, because I never really knew the basics. So I finally hired a professional make-up person who specialized in crossdressers. During the whole process she explained to me what she was doing and why she was doing it. I could see the transformation as she went through all the steps. When she was finished, she helped me put my wig on, and I was amazed at the look I (or she) had accomplished. Not only did I look like a woman, but I felt like a woman, I felt complete. And yes, there are still a number of firsts for me to undertake ...

[CarlaWestin]

I also remember the first time one of my threads got over 100 replies.

:straightface:

Oh, wait. That hasn't happened, yet.

[marlacd]

Oh Well! Let me help you along!

I had several firsts. When I lost the leg fur and put on panty hose for first time.

When I got my first pair of heels that fit me correctly. (Mail order, I have BIG feet)

The day I got on the 'net and found out there were dozens of ladies just like me.

The day my upper lip had seen daylight in 18 years. (And found out I looked years younger without a mustache)

[sometimes_miss]

Firsts....hmmmm. At 15, the first time I put on a cute minidress outfit that my 19 year old sister wore when going out clubbing, doing my hair like hers, make up as best as I could, looking in a mirror and seeing a very hot teen age girl looking back at me. It pushed me into may more years of wondering what I was supposed to be. It was during the regular school year, I was playng hooky, both parents were working, my sister wouldn't be home until after six that night. I had the whole day to be a hot girl. And loved every minute of it. Even went outside to get the mail, figuring if anyone saw me, they'd mistake me for my sister, as by that time we were almost the same height, and we were both very slim. As I had on one of her bras, who could tell from a distance?

The first time I ordered my own girl clothes. I was....18? I had gotten a Sterns dept store credit card, and with each bill, came an advertisement for something. One month, it was a cute camisole and tap pants. I spend a while before ordering, but did it. Of course, everything went well, and I had my first official girl underwear of my very own. More clothes were to follow. I was always paranoid that someone I knew might have a job with the shipping dept at Sterns and wonder why I was ordering so many woman's things.

But the biggest first that I remember the best? Nope. Wasn't sex. And it had nothing to do with crossdressing.

It was buying my first car, and driving it home. By myself. Dad followed in his car, of course. But I had worked all winter to save enough money for it, and it was the exact one I wanted. And it was exactly as wonderful as I had always dreamed it being. Over the next year, I spent every spare minute behind the wheel. Over 40,000 miles that year, which means nearly all my spare money went to paying for gasoline. But it was worth it.

Three years later, I re-lived that type of experience when I bought my first motorcycle, and drove that one all over the place, too.

[Lily Catherine]

Getting fully outed by my parents almost a year ago. Sure, they weren't too happy about it, but there was a sense of relief I've accepted and am more than grateful for.

On that note, phoning a counselor trained in LGBT matters. They (singular) were among the more understanding individuals I've poured myself out to. Even though it was sadly a one-off affair, it was a considerable leap forward for me to at least come to terms with this side? part? of me.

Earlier than that, wearing a minidress for the first time. I was still too young to club, I simply thought the dress was cute (if a tad too revealing at the legs) and fluffy. I still like that dress, but I don't really have many venues for it. As you can imagine, it's a bit hard to go anywhere with a skirt that blatantly exposes the top of my stockings.

[PattiMichaels]

...first time I gave myself a meticulous pedicure.

...first time I shaved my legs, chest, and underarms.

...first time I saw myself in the mirror after a professional makeover.

...first time I attracted the look of a cute guy even though he knew who I was underneath the veneer.

[Martha G]

It was the first time that I was fully dressed with complete makeup.

I looked so much younger and felt great dressed as a woman.

[CarlaWestin]

Now I'm remembering a lot of firsts. This one just came to mind.
The first time I got clocked. I was walking around an urban area in the restaurant district.
A couple passed by on the sidewalk and I distinctly heard the woman say,
"I've heard of that! A man trapped in a woman's body."

(Insert straight face smiley, here)

[BrendaPDX]

The first time I bought womans underwear and paid for it. I was so nervous I didn't want to wait for my change. The first time I used a changing room, the attendant asked how many articles of clothing I had, she counted them out and didn't say a thing.

[Desiree2bababe]

First time I pleased a man and the first time a man treated me all evening as a woman, asking for a second date!

[ClosetED]

Typical first - first time I put on my mother's pantyhose from the hamper and got sexually aroused for first time.

Finding real silk stockings in trunk in basement (possibly from a grandmother)

First time I obtained my own hosiery - sent for free sample of Silkies.

Hugs, Ellen
(Closing in on 100 posts Carla!)

[Usulsjourney]

I think the most memorable first would be the point I accepted this was here to stay so I may as well enjoy it. I shaved neck down and ordered my first lingerie specifically for me instead of odds and ends I aquired from all over. Putting on those stockings for the first time on hairless legs was more than I ever imagined it would be. Followed up with a good pair of properly sized heels and I knew I made the right decision to buy my own things that I desired instead of poaching my wife's castoffs.

[Sarasometimes]

Great Thread Carla,
The first time I walked into a beauty salon for my appointment to have an enfemme makeover including hair. makeup and nails!
My first shopping trip enfemme to the mall with a GG image consultant who made it totally stress free. I have more of course.

[CarlaWestin]

Thanks, Sara.

[NancySue]

My cding was "progressive" beginning in my youth with nylons. So with each "new" item, a new breath taking experience. First and forever, stockings, especially Hanes thigh highs...ahhhhh, then nylon panties, Vanity Fair...next a bra..Bali flower underwire, heels, flats & sandals, a full and half slip, waist cinchers, garter belts and OBG. wigs, makeup, nail polish, jewelry, breast forms, and an all seasons wardrobe. And the beat goes on and on. (big smile)

[LisaJ1]

The first pair of heels I bought when I was 16 years old.I saved money up for them putting money off the side for them.I remember walking in and tried them on which they fit me.Purchased them and walked out with them.Still have them to this day.I was working at a service station at the time when I did save the money up for them.

[Joanne108]

A mile stone for me was when I went out on Halloween a few years back. I pre-gamed. I took the day off and took my time with my dressing. I thought I looked great. I went and did some errands in 'full costume'. Several cashiers told me that I looked beautiful when they figured out that I was a guy in costume. My line was that I had to get used to the shoes and forms prior to going to my Halloween party latter that night. i don't think any of them bought that line but they didn't laugh!

[CarlaWestin]

I just remembered another first. The first time I was pulled over by the cops while enfemme.
It was quite a long time ago. Pre-internet. It was a male officer and a female officer.
Back then, you could be arrested for perceived lewd behaviour so you had to really have your wits.
I remember the male cop suggesting that it was inappropriate to wear clothing of the opposite sex.
That's when I looked at his female partner in identical uniform and commented, "I'm not the only one crossdressing here!"
We had a good laugh and I was on my way.

[CONSUELO]

While there have been many unforgettable "firsts", the big one for me has to be when my older sisters dressed me in a corset just for the fun of it. That moment and the sensations it aroused are still with me. I learned several things at one time. I found the feel of the material very sensuous and wanted to have that next to my skin again. I looked at the sheen of the satin material and that desire has stayed with me ever since and of course I wanted to dress like a girl more and more.

[steph_2015]

Panties in my pre teens and from there it grew into dresses forms wigs heels and now I have more girly girl stuff then male

[Samantha_Smile]

My first pair of heels.
I tried on all of my clothes to see what looked best.
Now I'm obsessed with shoes LOL

[LydiaL]

My fondest memory & milestone: first (& second) time going out dressed to public places. Accompanied by another crossdresser, I was introduced to other friendly Las Vegas, NV CDers.

[Lorileah]

That's when I looked at his female partner in identical uniform and commented, "I'm not the only one crossdressing here!"
We had a good laugh and I was on my way.
I expected the last line to be "that's when the lights went out" How lucky that way back then you found police with a sense of humor

[irene9999]

There are a few but about 8 yrs ago I ordered a bunch of clothes online from a website catering to CDs. It was my first time fully dressing up with heels, skirt and panties! Felt amazing but looking in the mirror I didn't look much different (although my legs looked great!) so I immediately ordered a wig and makeup. I loved the way the wig made me look, it made a big difference IMO

More recently I would say it is a couple of outings during weekend nights on pride month. I went out to CD friendly bars and it was so much more fun actually interacting with others while dressed!

[fun_girl]

I put on heels

[GBJoker]

I'll always remember the first time I was dressed in front of another person. They didn't say anything about it. Now I refuse to dress around others.

[JaytoJillian]

I will always remember going out fully en femme to "Chaos," which at the time, was THE hottest LGBT club in the city. Been a club junkie ever since.

[Samantha54]

Shaving my body fully, and putting on stockings, garter belt, lace bra, and a short lycra dress. It was awesome! No turning back!

[franlee]

After the obvious 1st of completely dressing as I have shared before. The next most memorable 1st was one afternoon in 1973 on a rain out day(couldn't work) my wife and I switched roles but this time she did my hair and makeup to be just like she wore hers. She dressed and did her hair like I wore mine, she dressed in my best suit and I dressed in her nicest dress and matching heels with her jewelry just like she would. Then before we left the bedroom to leave we stood side by side looking into the big mirror and I was astonished, I actually looked so much like her it was scary and I could see the realization on her face too. We had been mistaken for siblings many times but I recognized the reason people said it so often right then.

[Joan58]

Purchasing my first heels, walking in them the first time was a big thrill and first for me. Even better was my first time with my own makeup. My wife helped me choose the right colors.

[Rain Kensing]

Wearing mom's LEATHER pants with a pair of her highest heel boots. Ever since then I've had a thing for boots and fetish clothing. Recently got my first pair of leather pants.

[realdesired]

My First time was at age of 9. I weared panties then bra.... And so on... Today i feels i am a girl so i can wear anything

[Charlessa]

wore ladies outerwear in public. I went to dollar tree wearing Victoria's Secret yoga pants. it was extremely crowded. I was nervous but nothing bad happened. I soon progressed to skirts.

[ClosetED]

First time I help Carla reach her goal

Hugs, Ellen
(Very close to 100 posts Carla!)

[Alexa CD]

I have so many firsts! How can I name just one. The first time I put on eye makeup, seeing my eyes like that for the first time was really nice, lipstick as well. What else, a full outfit of clothes, not just a few items, and when I was finally able to pull my hair back into proper ponytail. I remember all those little moments, those first times were pretty big for me.

[SusanCACD]

I remember the first time I was "Mamed"? I went out to lunch with the people I worked with and the waiter asked " and what would you like mame? I have to admit I had just had my brows do and the lady doing it really went overboard. No one said a thing.
Susan

[Rachel Morley]

Definitely one of my highlights was going out clubbing (dancing) at a nightclub with my wife as two girlfriends having fun. All my life when I was younger I was so jealous of being at a club and seeing young attractive GGs who would be there in super cute dresses, high heels, full makeup, awesome hair, looking pretty and having a lot girly fun with their friends. When I first when out and did the same with my wife (about 10 years ago) we listened to music and drank wine as we got ready together, then we took a taxi to the club and danced and had fun all night! It felt so liberating and i will never forget it.

[Lacy PJs]

A couple of "firsts" stick out in my mind. The first one would be sleeping all night in some baby doll pajamas. While I had worn them many times previously, until we were "empty nesters," they didn't stay on all night long.

The second one would be wearing a leotard & tights for most of a day while I did some work in the upstairs of our house.

One of the firsts that I'm looking forward to will be ordering my first wig and strappy sandals! :)

Lacy PJs

[larissa-laurie]

My first anything, my sister dressed me up totally female when I was about 13. She dressed me in her school uniform with all the lingerie possible and a nice fall type wig. Her putting makeup on me was very well done. She told me I made a good looking girl and she wanted to take me to school with her. This whole thing was exciting and when I changed clothes I kept on her panties, nylons, girdle, and slip and slept in them that night. Many thoughts and actions crossed my mind. It started a life long fling with dressing partially and totally feminine.

[Ina Girdle]

A couple of firsts after 50 years of stealth & very sporadic CD'ing. Getting, trying on and modeling my first lingerie purchase, (a Rago Long Leg Panty Girdle) after coming out to my wife, what a feeling of excitement & accomplishment.

And just recently, on a trip to see my Dr., while wearing one of the few pairs I have left of (Gender Appropriate Underwear) as I call my old BVD's, a feeling of "I just don't feel properly dressed without some form of shape-wear on. It has been 3 years of almost daily wear of girdles or moderate control panties".

Thanks also to this group, I don't post all that often, but I read posts everyday. Like many here, the feeling of not being alone in the world after YEARS of feeling that I was a solitary oddity in the world.

Cheers! Ina G.

[Matterhorn]

The first time I went to a shopping mall with the goal of buying some girly things for me, confident in who I was and ready to speak to any employee who might offer help

[Jenn A116]

First time I bought breast forms! Many, many years ago. Had been using rice-filled knee-highs for several years and finally made the decision to go for the forms. Went to a CD store (Vernon's, now defunct) in Waltham, MA and have been enjoying the boobs ever since. Well, not the original ones. Those are long gone. But since then its been real forms. Actually considering a new set now. Thinking of the self-adhesive ones.

[Meg East]

When I came out to my wife. Now the only thing in the closet are my dresses.

[lovetobedani]

The first time I dressed in my mothers clothes when I was about 12.

[brenda girl]

i was about 13 when i first put on my mother's clothes, now i have about 15 dresses of my own to do my thins

[BethanyCross]

The first time I got party nails at a salon. I used the "lost a bet" scenario and went to a nice beauty salon. I was so nervous I was shaking. I left the salon with long wine colored nails and the nail tech and receptionist thought it was hilarious. I even got the "Now you know what a woman has to do to be pretty!" line. Awesome experience.

[valerie anne]

Ordered a bra online, waited for the mailman to knock and demand a signature, rip open the package, and then to discover it didn't fit at all!

[kymberly]

for me it was the first time i went bra shopping and told sa the bra and panties were for me,I still remember going into the fitting room and trying the bra on and have her making it fit properly.

[Sometimes Steffi]

For me, it was the first time I saw a crossdresser IRL who was pretty and passable. Until then, my only vision of crossdressers were comedians like Bob Hope, Milton Berle of Flip Wilson or drag queens.

[jacques]

the most important first time for me is on its way slowly - not really worrying what others think of my choice of clothing
luv J

[Katie01]

This thread brought back many sweet memories!
Old: 15 or 16 (1980's) going into a lingerie store and the sales lady helping me select and try on panties and a bra.
New: a few months ago walking my dog late at night wearing a dress for the first time.

[Samantha Clark]

Lots of firsts. Too many to mention. But only one milestone: telling my wife. Now I don't have to hide or purge.

As for firsts, nothing tops [sic] the first wig. That transformed this guy with makeup and a dress into Samantha. Indelible memory of that first time when I said "well hello, you!"

[Vicky Peters]

After reading the threads and thinking that each thought was great, the one that still remains the first is looking in the mirror and seeing myself with a wig, makeup and a blouse.
The image that I never saw before is still vivid in my mind. Now working on my makeup skills.

[Sephone]

Seeing myself fully dressed for the first time in the mirror.

[BrittanyB]

Oh easy...buying my first wig in person. I almost vomited before going into the shop. Actually seeing different wigs on me and how they framed my face was such an important thing to becoming more passable. Halloweed wigs are NOT the same! LOL

[Flirty_Fantasies]

The thrill of slipping into stockings for the first time was immense.....and this thrill has grown ever more intense--then to sit wearing them while transforming with make-up, lipstick, and arranging ones hair with the feminine feel of my stockings around my legs always giving the sensation of being a woman.....Mmmmmm!

Janelle XOXOX

[evadan]

Telling my wife, after years of dabbling with lingerie in the bedroom, I wanted to dress completely as a woman - and she agreed. Then a month later, after 35 years of collecting lingerie, odd pieces of clothing and purging - going shopping with my wife for a complete outfit (thank you Dressbarn and Payless) and dressing for her that evening. She's so good to me!

Good Thread!

Thanks -

Eva D.

[TakaraYu]

I guess I'll always remember the day I drowned all of my nerves and bought some women clothing.

it's still a work in progress thing however

[baldy1]

Wearing a Mini-Skirt at the sea front with my wife present

Julie

[phili]

When I wore a black and white dress out for the day- it fit perfectly, and I felt happy to be me - so I didn't mind the very few stares or chuckles.

I really loved it when the friendly young women at the museum wanted to talk- I felt I had established a public niche for any man who wants to wear a dress.

[julielivingmylife]

My first time outside was just amazing - it was dark and I just walked down the main road near my house (with only the occasional car driving past). I wasn't very passable if I'd been seen close up but that 5 minutes was such a rush and I felt so free. I didn't want it to end but I heard voices of people coming towards me so I turned back.

[Being_Me]

...shaved my legs.

...wore hose. I actually remember my first time buying them, too!

...wore a cute outfit while shopping for cute outfits at a department store.

[Alice_2014_B]

The very first time I dressed up and walked out in public in high heels (six inch heels with a front platform); at this point I had YEARS of experience walking comfortably in such heels.

It was exhilarating and scary at the same time.
:)

[Nora_H]

The first time i wore a skirt and crossed my legs. Yep, that was a life changing experience. I was 15 at the time, my legs looked very feminine and smooth.

[Julie Denier]

... dressed completely, including wig, makeup and shoes that fit. It was just six years ago, after decades of piecemeal experimenting, figuring that with my size, I'd never pull off a total look. But when it all came together, I liked what I saw. I've refined my look a LOT since then.

... went out in public dressed, still the only time to date. While traveling for work, went to a TG-friendly venue, "chaperoned" by a sister from here on the forum. Thinking back, it seems almost surreal -- way outside my comfort zone, yet I dove in with both heeled feet. It was a great experience, yet I don't feel a great urge to venture out again, like everyone said I would. But would I do it again under similar circumstances? Probably ;)