First Time Going Out

[Crystal120]

I know this thread has been posted before on here but I love reading everyones first time going out dressed. The good and bad maybe it will give me enough nerve to try it someday. I know you girls have some great stories. Please respond.

[Vikky]

Three of four years ago, with my wife being away for a couple of weeks I had plenty of time to dress (at home). However, this had to be the chance to try going out so dressed in a loose skirt, blouse. jumper and the usual undergarments went out in the car.

Left about 9.00pm, avoided putting in forms and wig until I had done a couple of miles and then drove around for about 90mins through a couple of local towns feeling very conspicuous but OK. It was a great ?rush?, but not yet repeated.

Go for it Crystal!

Vikky

[Julia B]

I don?t remember my first time out but I can tell you it is wonderful to go out and be who you are in public. I so enjoy being my femme side when out and my partner enjoys it too.
I used to worry about having mens clothes in the car just in case but I no longer do that, I am who I am and am proud of that. I will admit that it is exciting to know that whatever happens while out my femme side is in for the total adventure.
I now take weekend excursions with only girly clothes which gives me no chance to back out once I leave for the trip.
Girl do yourself a favor and go out that door tonight.

[kimdl93]

My desire to go out had been pent up for a long time and for the usual reason…fear of the unknown. Then, one summer day I remember I stepping briefly out my front door to move a sprinkler. I had finally reached the point where I unwilling to change back into male clothes for such a small, quick task. The world didn’t end. No mob assembled at my door.

That small step seemed to break the ice. Within days I had made my first shopping trip en femme, gotten a make over and a wig.

[TAG]

My first time was to a trans meeting and all went well.
We all went out together for dinner at a steakhouse down the street.
I had a great time but actually going out on my own was even better.
Went shopping and bought some make up and assorted make up brushes.

[cdinmd206]

I had done the dressing as a french maid for Halloween, but the first time to actually get fully dressed and go out in public was when my then wife and her best friend took me out for my 50th birthday. Her fiend bought me a button down the front dress and the wife bought me a new garter belt, stockings, panties, bra and heels. OMG what a rush as they helped me dress and apply my makeup. We had a nice dinner with drinks in downtown DC and then went bar hopping. By midnight they had unbuttoned enough buttons on my dress to show off my stocking tops and garter straps and lacey bra. What a rush that was.

[Helen_Highwater]

Crystal,

I guess it started for me with evening drives, changing in the car. Initially just a drive, then stopping somewhere quiet and briefly getting out. That morphed into walking further away from the car to say a post box. Getting braver it became a walk alone quiet streets and my progress stalled there for a good while.

My first time at a support group was a big step forward. I can remember walking into the small hotel's lobby where they met and the sound of my heels on the marble floor. Meeting others was a major step up.

It was from one of those meeting I got the drive to finally go out fully, into the shops. Butterflies like eagles, nervous as hell, parked up outside, deep breath, moments pause to pull up big girl knickers, step out the car, coat on, bag over shoulder, remember to lock car, and head for the nearest shop. Within ten minutes nerves had calmed 90%, an hour later I was in my umpteenth shop and queuing to pay for a piece of jewellery.

The rest as they say is history

[JocelynJames]

Hi Crystal,
This was from. The only time I?ve been out;
Well, my wife and I finally went out with me en femme. The first place I went to was a local hotel that also has a restaurant and bar. We got to the main hall and after one look in the bar I chickened out. So we drove to Pizzaria Uno a few towns over and I couldn't bring myself to go in as their bar looked jammed and I know it's small. Right next door was a Outback. Their parking lot looked near empty so we went in, got a table for two, and had a drink. My wife did all the talking and I did a lot of nodding with some small 'yes and no thank you' . I'm sure someone knew but no one made a fuss. Worst part of the night was I wore heels that were a tad large and made walking tough. Next time , I will know. I wore a multi color Daisy Fuentes with black patterned tights and black heels, and a butterfly necklace borrowed from the wife.

[Patience]

I planned to have my first outing during a Pride weekend three years ago. I picked the outfit in advance.

On the day of the outing, I left home in drab early in the morning and drove to my local University. There, I went into the disabled stall and changed into my outfit: A long stretchy skirt and a very nice top to match. This was before I had a lot of stuff, so I wore regular tennis shoes and since I did not yet have a wig, I settled for sunglasses and a baseball cap. It was early enough that no one else came in the bathroom when I was there.

I exited the bathroom and the University building quickly, got into my car and drove to the local gayborhood and went to sit in the park, which is fairly large and is a venue for public events. I found an empty bench, sat down and basically hung out en femme for a few hours watching other folks, soaking in the good vibes and feeling giddy with excitement.

Did everything work out perfectly? Not really - while I was sitting, a bunch of 20-somethings were meeting there for the weekend and were a little drunk. One of the kids ( the most drunk of the bunch) told me a couple of times to show what he called my "fat tits" and very nearly spilled a beer on me as a joke, I guess. Fortunately, his buddies reined him in.

My second issue during the outing is that I had folks take pictures on me using my Android phone and I later learned in horror that the pics were uploaded to a Google Plus account. Fortunately, the images were in a pending approval status and were never published, but that was enough for me to invest in a small point and shoot camera with no internet connectivity.

The last and worst outcome of the outing is that I was out in the sun for hours without sunblock, and at the end of the outing, I ended up with a massive sunburn shaped like my obviously feminine top. Besides the pain, the telltale tanline didn't go away for at least a week.

On that day, I left the park around noon, drove to a music store where I've shopped at least 10 years and enjoyed shopping enfemme for the fist time. Then I went to Goodwill and ended up buying a dress. These are places where I still shop, but now I can go 100% fem, from my wig to my cute shoes.

I went out dressed the following day, but it was obviously not as memorable.

[KristyPa]

I suggest a tg/cd friendly bar typically a gay type bar.

Go first in drab you will get the feel for the place which will make you more comfortable when you go as Crystal. Do not over dress I made that mistake the first time I went out I wore a dress like you would wear to a wedding reception, way over dressed, I never made that mistake again. I suggest jeans very few people wear a dress or a skirt to a bar.

You will more than likely be scared, very normal I still feel a little fear when I first walk in. Remember this, no one cares only you. Each time you go out the easier it gets you'll love it once you do it a few times. Its so much better and exciting being out of the house.

[Lana Mae]

Very first was a car ride with clothes, no wig, nor make up! Then the question, Am I actually going in this direction? So, I decided on a transformation and make up lessons! First time out was in a large western NC city for a wig purchase! Jennifer, who gave me the transformation and lessons was along!
OK, first time fully dressed with wig and some make up, to a MAC counter in the mall and alone! Changed from flats to heels! Walked thru parking lot to entrance! So far so good! Resisted temptation to go in Victoria Secrets! Checked with MAC counter and no, it is the one down in Macys! Took the escalator down! Passed a few people! I reached the MAC counter! I told the MUA I wanted a color match! She did a great job! I bought a few things! I walked to the stairs and climbed them! A man on the bench reading his paper, glanced up, did a double take and went back to his paper! I retuned to my car! I did it! I actually did it and alone!
Take your choice as to which was a first!
I am now a pre-op transwoman and out 24/7/365!
Hugs Lana Mae

[SarahBJackson]

My first time out was at a Pride event when I lived in Kentucky. Lexington Pride in 2012! I was a hot mess!

[Geena75]

I had stepped out on the deck behind the house and taken drives before, but the first time out of the vehicle is what counts for me. Last summer I planned out an excursion to see a monument a couple towns away. Admitted, I overdressed in a short black dress and patterned tights, but I wanted to feel feminine. Got lost once, but felt so free just letting it out and not being afraid of anyone seeing me (admitted from a distance), but was so emboldened I stopped and checked out another site on the way back. Kept saying "I did it!" all the way home. It took a few more outings before I felt confident enough to be seen closer, and was rewarded with an SA stopping me to tell me I look absolutely adorable. Still riding high from that.

[NjJamie]

There are probably so many firsts in all of our adventures, but the one I'll remember and treasure most was the first time I went out the front door, with keys in my hand, and drove away from home. It was when I was about 20 and though I had been dressing since 13 or so it was the first time I was going to leave the house while pretty.

I was wearing a warm pink two piece knit dress, blonde wig and heeled sandals, my best effort at makeup and had painted my toe and finger nails. I managed to back out of the driveway without accident, drove a few miles away and finally parked in a quiet neighborhood, got out and walked around. That was about 40 years ago and there is still a thrill to walking out the front door with keys, you really should give yourself the chance and enjoy it! I will say my last outing was to a local mall on a Sat afternoon, it was packed and I guarantee I do not pass but I was "mild" enough that no one seemed to notice or care, except for the SA I almost knocked over in the lingerie section when we met at a corner!

Picking through the racks of dresses or bras only 2-3 feet from the other shoppers and just being considered another shopper can be surreal but has has been stated here and elsewhere, no one really cares enough to even notice. If you dress to blend and make a good effort, almost everyone will see you as who you seem to be!

[docrobbysherry]

I can't recall my first or last outing, Crystal. I'm too old and have had so many.:battingeyelashes:

However, I DO recall the ones that blew my mind or scared the crap out of me!:devil::eek:

[Jean 103]

Well I may not be able to remember the first time but I certainly can remember the last time as I just got back a few minutes ago.

Going out dressed for me is normal. Which then poses a question why was it ever such a big deal?

Although I have learned a lot along the way.

[JuliannaS]

The first time i went out dressed (aside from Halloween parties) i went to Home Depot. I kept it simple, not wanting to draw any attention to myself. I wore skinny jeans, black tank top, padded bra with a flannel shirt, unbuttoned, my red curly wig, slide sandals, toenails painted red. I did not do any makeup. I wore a face mask, and purple sunglasses. I don't know if anyone noticed, and of they did, they didn't care.

[Jenn A116]

The first time Jenn went out was just to the curb to get the day's mail. I waited until after dark, turned off all my outside lights, took a deep breath and...
walked out there and back. How was it? Scary and exhilarating! Have now done that a couple of more times. But that's the extend of Jennifer's time outside the house. So far...

[Heather76]

My first 2 times out were just onto the back patio late at night while letting my dog take care of business. I was seen by nobody. The closest I've come to being dressed while out was getting out of the car to fill up with gas at a somewhat busy gas station on a busy corner. While dressed in my male outer wear, I did have a bralette on with my DD cup teardrop forms. IF anyone looked at me, there would have been no question that I was underdressed. If I ever go out fully dressed, it will wait until I am comfortable with my makeup and wig. It will also not be in my neighborhood.

[April Rose]

My first time out was with my girlfriend(eventually to become my wife.) I had just come out to her because we were moving in together. In one of our conversations I had mentioned being curious about what it would be like to be outside dressed. She loaned me a skirt and top and took me out for a walk around the block that very evening. I already had shoulder length hair at the time.

Years after we had moved out of that apartment I found out that one of the early crossdressing clubs, the Cherrystone Club was right across the street from us the whole time we were living there. This was Looong before the internet.

[Karren H]

My first time outside was when I was 16. In the 60s. I wore my moms clothes and shoes. Makeup and since I had no hair I stuck curlers in my hair and put a hair net over it. I felt amazing but I must have looked horrific! But I snuck out the basement stairway one night and took a walk around town. Was pretty scary living in a farming village of less than 1000. Getting caught would have been the end.

The next time I ventured out into the public was 30 years later. On a business trip. I loved going out enfemme on business trips, did it for almost 20 years. Really miss that a lot.

[Elizabeth G]

My first time out was equal parts of terror and exhilaration.

In a once in 20 year occurrence my then wife was going to be away for three days and the pink fog, which ebbed and flowed with me back then was absolutely raging. I had managed to put together one complete outfit and I could think of nothing but dressing leading up to that day.

I rushed home from work and began my transformation. My outfit was a plaid midi length skirt, a dark turquoise cowl neck sweater, boots and a camel colored corduroy jacket, perfect for a New England fall night. I wish I still had those pieces but they are long gone after a purge.

I lived in a tiny town across the street from a little general store and I remember nervously waiting for it to get dark enough outside and quiet enough at the store for me to dash from the house to the car unnoticed.

I drove to a nearby town and kind of looped around for a bit and eventually pulled into a gas station where I sat for a minute j until I got up the nerve to step out of the car and fill up. I felt like everyone was watching me even if they weren't. I then went through the same process at a nearby grocery store. Later I drove to a town further out and summoned up the nerve to go into a K Mart and browse the clothing tracks but didn't buy anything. My last big adventure of the evening was to stop in at another gas station to use the ladies room. I distinctly remember a rather tough looking young man politely holding the for for me and smiling at me on my way in.

As I said, equal parts terror and exhilaration but it was a wonderful experience for me overall.

[kellyanne]

First time was a car drive - had to walk down 10 flights to my car, had grapefruit in a bra for boobs, I left at @;30 am and felt like breaking out of jail. Soon after taking to the road, I noticed men eyeing me i - not that I was a doll - but that I was a woman alone driving late that was exciting and eerie. I now understand how a woman feels alone to some degree.
My make up was good from far but far from good in the light , so when I went into a 711 for smokes he looked at me unflatteringly but I still felt proud.

One thing that accentuated the experience was wearing high heels for driving.

I would be out all the time if it was safe.

[Krisi]

I never had a "first time going out". I remember going out for a drive while wearing a bra and then inserting water balloons once I was away from the neighborhood. The next step was to buy a cheap "Halloween" wig and put it on (along with the water balloons) once I was away from the neighborhood. I also wore my wife's blouse. Eventually, I got out of the car (at night) and took a few photos.

I progressed to actual breast forms, hip and butt padding, a decent wig and my own clothes and shoes. And purse, got to have the purse.

So no real "first time".

[Natalie5004]

I remember my first time out dressed up. I did not look good at all. But I felt I was just released from jail. It was fantastic.

[Raychel]

I have been out a few times.
Much easier when I lived in Tennessee. My house was in a very private place.
I could park the truck close to the door and could get out easier.
I would go for a drive occasionally, never getting out of the vehicle.

Now living in Maine, my house is in an Mobile Home Park, Houses very close together
Definitely more of a challenge to get out.
Although I have been out a couple of times, Leaving and changing after I left home.

Having been laughed at and ridiculed so much as a child. I really have no desire to even get close to that again.
Therefor I am very careful to avoid those situations.

Plenty of deep rooted issues here.
I will never be able to just go out how prefer to dress.
But my hats off to all that can.
I bow to my idols. :) :) :)

[Just Dana]

During COVID (the worst part of it), I got up the nerve to go for a drive while on an overnight in another city, then a month or so later, my wife and I went for a wander in downtown Chicago on a weeknight in winter. I didn't have to interact with anyone on either outing. So, what I consider my proper first time out was...

Last month, I was supposed to have my very first date as Dana. I bought a new dress, a black, long-sleeved, midi length sweater dress, since I didn't really have anything for going out on a frigid February evening. My wife loaned me a beautiful, red scarf that really set it off and matched my red glasses. I scheduled my first professional makeover at Transformations by Rori. Then, he cancelled. Thanks COVID! But, everything was set and Rori had even scheduled my makeover at her posted closing time, so I decided I'd put on my big girl boy shorts and go anyway. As it turns out, I wasn't alone; Mr. Murphy accompanied me all evening. ;)

When I got to Rori's, there were three 60ish women trying on wigs. They had no idea it wasn't your everyday wig shop. Rori showed me to the dressing room and I got changed - from the neck down. I'm not sure what the women thought when I came out and started browsing while they were finishing up with their shopping, but I'm sure I gave them a good story for later. Then, Rori did my makeup, helped me get my wig just right, and I was off.

Not two blocks from the shop, a younger guy pulled up next to me at a stoplight, a bit ahead of me, since he'd slammed on his brakes when he saw me. He craned around, looked right at me, and nodded. I nodded back, since that's the polite thing to do. He then proceeded to pace me for the next block or two. I looked straight ahead, but out of the corner of my eye I could see that he kept looking at me and gesturing, trying to get my attention. It was definitely a bit scary. I made a quick turn off the main road and lost him. I have no idea. Did he immediately clock me and think, of course a transwoman out for the evening would want to go home with him? Did he think I was a woman, who'd be impressed by his road seduction and want to go home with him? Was it something negative? Beats me. But, I didn't let it bother me and continued on with my evening.

I went to a LGBTQ bar (regular Chicago neighborhood kind of bar, not a dance club) for dinner. I got there and dug my vax card and ID out of my purse, completely forgetting to put on my mask. (Doh!) I walked in and the bartender said something like, "Hey glamorous." Short pause. "Do you have a mask to go with that? You need to wear a mask in here, honey." I was so flustered about the mask that I didn't mind that everyone turned to look at me. :) I fumbled around in my purse again, found my mask, and all was right with the world. The waitstaff was great. The rest of the customers seemed to completely ignore me. Nirvana.

After dinner, I'd hoped to stop at a Target and do some shopping. Unfortunately, it was already closed. So, I walked around the block and found a little shop where I could buy a six pack before heading home. The store was run by two elderly men and you're supposed to scan your ID when you enter. (This was near Wrigley Field, so there are always lots of under 21s trying to buy alcohol.) I had to hand over my ID, so one could go back to the front door and scan it. I'm well past getting carded, so I was not expecting that at all! They were perfect gentlemen, though.

Before I got home, I found a spot to pull over and put on a pair of jeans, hat, boy coat, and a mask, so I wouldn't have to walk down my block all dolled up.

It was the weirdest evening. It seemed that everything that could go wrong, or at least not quite right, did. But, I had an absolutely incredible time!!! Once I put on that dress, I was in the zone or something. It's kind of like when I have to get a shot or a blood draw. I'm always very nervous beforehand, but perfectly fine once I sit down in the chair.

So, that's my story. I hope to do it again, but without the hiccups!

Dana

[TamT]

My first time going out was about twenty years ago. It was near midnight and I was with makeup, a party wig, water filled baloons and a not very blending outfit: mustard synthetic leader pants, a red&mustard blouse, a dark red synthetic leader jacket and red sandals. I always wanted to go out, and I was so excited that I put some Ids and cards in a purse, covered my outfit with a windbreak, a jeans and a sports cap, changed my shoes and walked to my car in the parking lot of the building. There, I removed the jeans and put the sandals again. After I left, I stopped some streets later to remove the windbreak and the cap. I drove for about half an hour without a destination, but at some point, I parked and took a deep breath before opening the car's door. Once out, I walked for about 5 to 10 minutes in the neightborhood, returning to my car from the opposite side. I drove back to my home, covering my outfit again with the windbreak and the cap.

I repeated that few times in the following months with different outfits, but those were other times. Today, I'd not recommend going out late at night, as it has gotten dangerous, at least in my city.

Being in a DADT relationship, as I cannot dress at home and I cannot pay for an hotel room, I found it much more easy and fun to underdress in the morning, then dress and apply makeup in the car during lunchtime and drive to a mall. I don't care if I blend (I know I don't pass), but I own it. I can check for sales and buy more clothes and accessories as Tam without any bad experience at all. I return to the office after an hour, remove the makeup and clothes still in the car, then back to work for the rest of the day.

[Jenni6521]

I have been out in various stages of being dressed many different times. Recently, it has been jeans, blouse, shoes, no makeup, forms or wig, don't own them. Last Friday I went for my first complete makeover. That was the first time in my crossdressing career that I put it all together. I planned for my trip to Washington DC for the makeover by stopping to get my nails done first. I had them painted in a soft pink. That was the negative experience. I walked in and was asked to take a seat near the back of the salon. There were no other seats available. After sitting down there was a women getting a pedicure, she gave me terrible leers for most of the time I sat there, along with lady who was giving her the pedicure. To build my courage I just continued to say you deserve to be here and you are okay. I also avoided eye contact. I was sat between two young ladies during my manicure and both of them smiled kindly at me. I know that I opened myself up there because of not wearing a wig or makeup. My makeover was amazing, and I was stunned to tears when I first saw myself in the mirror. I left there with my makeup still in place, the same blouse and bra, jeans and shoes that I wore. I went to check into my hotel room and that was the one of the best parts. There were to female clerks at the desk, one young and one closer to my age. The younger one checked me in and asked for my CC and ID. I got them out of my purse. She stared at my ID for longer than I expected her to. Then she asked "is he here." Only my sisters here can understand the smile that came to my face. I removed my mask and said he is right in front of you. She had this wonderful smile, and then said you look beautiful, which lead to another tearful moment. The other clerk walked over and was also very supportive and mentioned that she wants to get a full makeover. She commented on how pretty I looked. I went up to the room. I had planned on maybe going out, but was pretty pooped. I went to the target to get some makeup wipes and a couple of other things. I grabbed some takeout and went back to the room. The next morning as I returned the key, they were also working. Which started a new conversation with both of them.

[Wendy-Lyn]

I've been dressing on-and-off for decades, but mostly only partially and for limited times. And always at home. I NEVER dreamed I'd ever have the guts to go out in public dressed, although I'd often wondered what it would be like. My first time out in public was not long before last Christmas. I went out underdressed and changed in the car into a skirt and shoes, put on my wig and some jewellery, and went to a park and ate lunch while I watched some kids playing cricket. Then I went to a place I know and got out of the car and went for a walk. I was terrified, but exhilarated at the same time.
It seemed to unlock something, because I've been out fully en-femme a few times since, and I often go out in 'stealth' mode even when presenting as Jimmy. I've even been shopping en-femme a couple of times, but nothing too exciting - just makeup and odds-and-ends.
Onwards and upwards.