What did you wear on the first time out?

I went to a Halloween party about 15 years ago which was a perfect test run especially since there were a few lesbian and gay couples as well.  I wore black pantyhose, a short black dress with a deep neck line. 3 inch heels black strap.  I was more concerned about the makeup job. Thankfully I had plenty of secret practice and had a dark purple and grey eye shadow with deep Crimson lipstick and a professionally fitted wig (auburn).

I was never comfortable the entire night but it was a Halloween costume party so no long term stigmas. In hindsight I do recall a few comments that I was passable which I didn't believe at the time, but I have since ventured out and although I'm 15 years older and my skin isn't quite as smooth I do think I look ok.

Remember it's better to regret things you've done that regret those things you haven't.

Heather

HI Heather,   First let me say that you look pretty darn good to me so you are better than ok.

I do not recall exactly what I wore my first time out walking at night.  My favorite outfit was a tight pair of white shorts, I forget the color blouse, bra padded with my softest socks rolled up, and a kerchief to disguise the fact that my hair wasn't girly.

My first time out as a woman I was a blonde, in a skirt and top - no I don't remember the colors, but I had full makeup, silicon breast forms, false lashes and my wig was from Paula Young, although my earlier wigs had been from walmart halloween selections.  I also had rings, necklace, earrings and other jewelry.  It was a great experience even though I was the only one in the bar for nearly 2 hours.

Must complement your wife, she's your angel and definitely in love with you.

Great post Julianne! The first outing is a big step(I couldn't tell where you said you had posted your story before) .  Congraulations!

Cynthia

Found your other post Julianne and replied there-read it and feel free to PM me anytime!

Cynthia(Cyn)

Well I have to travel in the  memory banks for this one. I think it was a brown skirt,  with matching top, I believe it was a pair of Candies heels, no wig or makeup.  Know that I walked down the street to the local park and back.

I shudder to think about it.  I was fourteen and the only clothes I had were liberated from the Goodwill bag, or purloined in some less honorable way.  The shoes were sparkly pair of flats the were too small, the dress was an ugly green shirtwaist that Carol Burnett's "Char Woman" character would have rejected as ugly. I did have some nice undies on bra, panties and slip.  I wore a scarf over my head with my hair (short) pulled over my forehead to simulate bangs.  I simple went for a walk in broad daylight.  Our neighborhood was a mix of industrial and homes.  The shortest circuit was about four blocks square and involve short distances on two main well traveled main roads.  I strolled around it trying to look average.  I ask you, what kind of fourteen year old girl would have been dressed like that?

Amazingly enough, no one notice, though I didn't come into direct contact with anyone.  Even more amazing was it wasn't my last time out in that outfit.  Emboldened by that experience I went out several more time, increasing my travels, still never coming in direct contact with anyone, only cars driving by.

Only once did I come into contact with anyone.  It was when I went to a closed service station to use the restroom and discovered a couple of younger neighborhood girl sitting on the counter talking.  They of course read me and one of them recognized me.  I lived in fear of repercussion for a long time after that but none ever came.

It was crazy…like an out of body experience.  i started the day putting on a matching set of Cacique blue satin bra and panties borrowed from my gf at the time.  everything was hers except a wig that i bought a few days prior.  A pair of thermal sox in each cup and a pair of opaque white tights and i was doing it. I had a wool tweed mini skit from the Gap that had 3 leather buckles on the right hip. I pulled the skirt up above my waist and tried to give the impression of hips.  At that time i had no idea about padding or anything like that. The top was a long sleeve cream cotton mock turtleneck sweater with a small cable knit pattern.  The shoes  were a pair of tan ballet flats.

Again totally out of my head i walked out of the house thinking i was invisible and could not be  seen.  With no makeup i drove to and walked into a Merle Norman.  being an early weekday it was empty.  i asked the clerk how to apply makeup to look more like a girl.  At first she was taken aback but the matronly clerk at the make up store somehow saw the sincerity of the request from this young college kid.  She literally said no she couldn’t but did a full makeover, probably because no one else came in.

i drove to a McDonald’s for lunch, was snickered at and then went to a local lingerie and bra shop that i had been to a couple times as a boy. It was not a sleazy shop but one catering to older women and mastectomy patients.  It had a few racks of shape wear for the ladies for formal or special occasions…strapless bras, body briefs, clinchers and slips.  like i said it catered to an older clientele.  It was there that i was also clocked!

A salesgirl, i think the daughter of the owner,  while helping a lady, peered her head over the rack and said “Hey you’re back! I will be with you in a minute.”

Somehow I must have mentioned to her that i was going to dress up. To this day I have details of previous memories of visits there blocked, but i know i had viaited.  When she came to talk to me she said i looked great. She said,” when you told me you had a skirt and sweater from the Gap. I thought ew! But this looks really cute on you.”  She said i should go to the drag show on Sundays, but i was under 21.  She made a sale because she sent me to the dressing room when her boss wasn’t looking.  Obviously i must have looked as straight as a board because she gave me a waist cinched to try on. Which i did.  She told me her boss did not like when men came in so she took my cash through the curtain and we parted. she was incredibly non-judgmental.

Luckily that did go well because on the way home i stopped at a gas station and dressed back to boy mode.  Something must have spooked someone because i got a 1/2 mile down the road before i was stopped by the police.  i am sure i came off as sweaty and nervous. who knows how much of the make up i was able to wash off and i had a grocery bag overflowing with women’s tights, clothes and underwear sitting on the floor of the passenger side.

I have dressed up since, probably more and more convincing but have never gone out again. the day started and i was invisible but every stop along the day i was not invisible. If i did chose to venture out again long ago, i am sure that i would be happier  for it.

My first time out was when I was four. Vague memories but I had a dress on, heels,fur stole, floppy hat and makeup. My mum dressed me up for a fancy dress competition - which I won! That was the start of a happy childhood of dressing up..

hi...............my first time out was by accident ................I was at home late night ......around 1 AM .................dressed in a short pleated skirt ..............nice long hair wig.........simple blouse ...........enjoying my girl time .........with a glass of wine .................I had let my dog out to ..........you  know.........take care of doggie business ...............well ................later I hear him yapping in the alley and could tell he was running around ....................I panicked and ran out into the alley before somebody could you know ......do  something mean ............I got ahold of him ..............while on the way back .............a car enters the alley .............crap! ................I turn away as it passes ....................the driver slows and says something about ............."nice dog........."  I nod and continue to walk away ...............he drives away .........................karley 

My first time out was when I truly realized I was meant to be a woman. It was Halloween and I wore a black knee length skirt, red blouse with low cut neckline, bra filled with toilet tissue, black 3” heels with sparkling straps, black wig, false fingernails, foundation, eyeliner, and lipstick. Iv was hit in that night by three men. Since that day forward, Sami has been slowly making her grand entrance 

I remember my big debut well because it was just a little over a year ago.  I traveled out of town enfemme, leggings and a cute top, but don't count that as aside from a Starbucks drive thru & hotel check in, I did not interact with anyone.

Early that night, I emerged from my room wearing a plaid wool over the knee A line skirt, a black rouched long sleeve top, black opaque stockings, with 4" black heels.  Only makeup was lipstick.

Upon entering the lobby, the front desk girl said.. oh, you look so cute!  And complimented me on my outfit.  Made me feel great.

Emily

My first time out was for Halloween. No one at work had ever ( for 10 years ) seen me without a beard. Home made breast forms filled a 36 c bra. Red ,black and white crocheted dress just above the knee with black leggings. Red and black wig. My wife did my makeup. I watched nail tutorial videos for 6 months prior to doing my own acrylic nails the night before. Took me 5 hours but they looked good. One of the drivers got excited. Goes into the logistics office. " Man have you guys seen the new hire?" "What?"  "The new Qualiy Tech. Man she's all curvy, got this tight dress on."  " You mean the Quality dude?"  "No"  "Yeah, it's the Quality dude." Another guy actually started hitting on me. Got so many compliments that night

I was only 14 but I still remember. Wore my sisters stripped dress, panty hose, heels, wig and used nerf balls for breasts. I took the bus to the mall. It was so exciting