i wanted to start a thread about first time outside world experiences... with just a tiny twist. i understand that walking outside in makeup, dresses, etc. for the first time can be difficult so i want everyone to post up their most embarassing time out so that everyone going out for the first time wont feel as nervous. ill start things off.

so ive only been in public while wearing womens clothing twice and this was the second time. it was 5a.m., a time when my parents are at work, and i decided to put on my moms clothing and makeup. i put on a flowery dress and flip flops (eck dresses and flip flops i know) and i felt great. so great i wanted to walk up to the gas station thats about a mile from my house just to see if i could pass.

3/4 of the way there a car pulls over next to me. its a cop. he gets out and because of the time, place (the country side), and my attire he thinks that i crashed my car. when he started talking and asking me questions i froze up and hardly said a word. when i did speak he seemed shocked that i was a guy (very little voice work). when he asked me what my address was i didnt respond and he threatened to arrest me. i spilled everything about myself with fear of my parents bailing me out while wearing my moms dress (she wouldve killed me for crossdressing).

finally he got whatever he wanted and drove away. i decided to go straight home and took a shortcut home. through the field. then it began to rain. when i got home i was soaked and muddy. i quickly scrubbed everything and attempted to dry it all but still had to hide some of it for later care because my mom would be home from work at any time. some how i got away with it all without my parents finding out.

OK try to beat that embarassment.

Um first of all when a cop stops you, that does of mean you have to respond, if he has no probable cause and you have not done anything illegal you just say I don't talk to cops, trust me, I hate cops and this is what I do, they can't do ->-bleeped-<-. Don't talk to the cops, do work on your voice though

Early on I went to lunch wearing a white tank that was a bit too see-through... braless.   I got some attention I really wasn't expecting, my friend who was with me through thick and thin said she was embarrassed for me.  That stung, I'm still embarrassed.

Fortunately haven't had any this time (partly because I learned from all my mistakes during my first attempt at transition). Possibly my most embarrassing attempt was when I went out horse riding with friends up in the local mountains where it was very cold. I didn't have any winter women's clothes and I could hardly go horse riding in a summer frock anyway, so I tried to make do with semi modified guy's clothes including men's jeans with rolled up cuffs and a bulky jumper/sweater over  a poorly stuffed bra (me bewbs were teeny and would have vanished under the sweater otherwise). The end result was probably pretty bizarre. My friends kept misgendering me and using my guy name, probably because they weren't sure how I was truing to present. What made it worse was that there was another group of people with our group and a horse riding instructor/trainer. I was getting lots of weird, freaked out looks. It was excruciating. I have a pic of me on horseback that was taken then, I look male andro at best... happened over 20 years ago, still embarrassed.

Let's see... I was at a rooftop bar in San Diego and an a*hole decided he'd point and laugh at me.  It's a miracle there was ever a second time.

It was the third or fourth time I was out. I was in a shopping mall and went to the gender neutral bathroom. It had no lock and a toilet that was literally six inches from the floor (clearly intended for parents to be able to wait outside while their toddler piddles without worrying about accidentally being locked out). While I was trying to figure out how to secure the door some guy walked in on me. Fortunately I hadn't started the act yet and all my clothes were on.

He apologized profusely.

My first time in public I went all out - I met some friends at a very popular gay bar bar in the Hillcrest section of San Diego. I had to overcome my fear of opening the door and walking out of the place I was staying, and I had to overcome my fear of people looking at me when I had to park two blocks away and walk past a sidewalk cafe full of people to get to the bar in my 4" heels. By the time I got inside the bar and no one had payed me any attention I was beginning to feel pretty good about things.

We were seated squarely in the middle of the restaurant, right where everyone could see us at a tiny table - not my first choice of places to sit that night but oh well. The table was too small for the food, and I  proceeded to accidentally knock a dish of salad dressing off of the table - LOUD SPLAT - and dish breaking sounds ensued. Well, every eye in the place was now on me and no one came to clean it up so I had to get off my chair and use some napkins to try to clean up the mess.

That was pretty dang embarrassing, and any hopes of maintaining stealth went right out the window.

When I was 15 I starting stealing my sisters clotjing and
Using her make up while she was at work.
And by 16 I thought it was a secret. But it wasn't and she
Locked the door when she left for work and didn't tell me she
Had plans for staying out all night. I was busted and she locked
Me out for the night and entire next day.
I wasnt to shy to be out as a girl ever after. Wow back them my make up
Was terribad and my clothing was like an alien attempt to
Blend in. And if course the usual creeps harrased me to no ends