First Time Out Stories

[Adriana Moretti]

In another thread, we got sidetracked off the original topic and got on to First Time Out In Public Stories and how we overcame our fears, so I figured why not start its own thread on it . How was your experience your first time out ? How did you feel ? Were you nervous ? Terrified ? Did you chicken out ? Did you have fun? What did you learn ? Did you enjoy it ? Did you like it ? Would you do it again ? Or did you get it out of your system ? Where did you go ? What did you do ? What was YOUR first time out in public like ???

Mine was already mentioned but whats yours ?

Here is a pic from my first time out since my 7 year purge ...and if you look to the right its Paula !!! also from this site !! To the left is Samantha...who is still here in spirit xoxo....

[Tara Rushing]

You girls look great. Can't wait to see the stories here. And when I overcome the cowardly lion within me, I'll post my story, too!

[mykell]

hi adriana, i remember samantha, jersey girl, paula not so much....

my first time out terrified me....yep, i was scared at how natural i felt and comfortable i was, it was a transgender support event so that helped but i was in front of parents and friends of a mix of trans folks from throughout the spectrum, had to put my makeup on in the car just before i went , still half in the closet as i call it, my wife knows but were private about it and i cant leave the house dressed underdressed with a few items, i had fun drove home all dolled up that night.

did it again after i brought some forms which i had a fitting for, needed a less revealing bra so i went to a outlet store dressed and was fitted for a bra, drove around most of the day until my corset got too uncomfortable....the next time i went to the meeting and was all set to get dressed and realized i forgot the forms left them in the laundry room, stressed for a bit and went old school and stuffed my socks into the bra, figured i was already there and racing home and coming back wouldnt cut it, talked to some of the ladies after the meeting

hate that i have no photos....

wouldnt mind hearing your story, missed it....

edit: bumped into that thread and saw your story....

[kittie60]

My very first time out in public I drove to a near by town and went and sat in the park. I wore a nice blouse and a short skirt bought a coffee and hotdog sat at one of the tables and read the paper.everybody that went by said hi and I answered them. It was a great day.I was nervous as all get out but that quickly went away. This was probably 22,23 years ago. Ivy been out before for night time drives but this was the first daytime interacting with people. I really enjoyed it and I've been doing it ever since. One thing I learned that day was confidence. Be yourself and and own the time out. Be proud of who you are

[Teresa]

Adriana,
I was nervous about going out about a week before the event , because of thinking all the details through. On the afternoon I tried to keep a clear mind and do things calmly in the right order. Stepping into the car felt great but had to wait ten minutes sitting in my drive while the car warmed up, it took an age for the screen to clear it was so cold !
The venue was tricky to find and had visions of stopping at a pub to ask directions , that just made me smile. On arrival I changed into my heels and then spent another ten minutes trying the do the ankle straps up, something which only takes a few seconds normally. So by this time I was getting cold and was grateful to walk into the meeting not feeling nervous at all. Greeting people for the first time was an odd combination of soft hand shakes and girly hugs, something I'm not use to.

Did I enjoy the event ? Yes I did , I will admit I didn't expect to be out dancing as well ! Will I do it again ? Yes they meet once a month and it feels too long to wait for the next one ! The venue is a hotel and conference centre , I didn't notice hotel guests but there must have been some.

[AllieSF]

The first time I dressed completely with makeup, wig, forms and even false eyelashes I looked in a hand held mirror and could not believe the transformation that I saw. I knew then that I had to go out with the new me into the real world. After networking on this site and another one, I found two members here who agreed to take me out into San Francisco. Prior to leaving my house I was, of course, nervous and a bit anxious. But hey, I was going out in SF the perfect place to take those first steps. I got to the restaurant first still anxious about how everything would turn out and then had to wait for my friends to arrive. I knew that I should have got there later instead. Anyway, I talked to the owner because I had heard that a T support group would meet up there occasionally. He confirmed that and I immediately felt more at ease. My two friends eventually arrived, we had a so-so meal and then went to Divas, a well known T bar and club with 3 floors with different vibes on each one. The first floor was more for drag performers to lip sync songs on a small stage. There were also a few working girls, or working girl look alike's there. Since the it was a slow night, we were early and they had closed the upper floors, we decided to head across the street to the Lush Bar, now with a new name. We spent the night there talking, laughing and just having fun with few other patrons around. I also talked quite a bit with the female bar tender who was great. That night proved to me that I could do it and have fun. The rest is history. Here is a picture from a couple of years later wearing the same outfit I wore that first night out. The same except for the shoes since I wore low heels that first time out and wobbled all over the place until I finally got my "she" legs.

[Sandy Clifton]

My first time in public was in 1998, at a Halloween party.

My outfit was a French Quarter thrift shop purchase: a cheongsam-style
dress made of an unstretchy material. I loved the design, but it was
probably about two sizes too small for me.

I managed to squeeze into the dress and stiffly negotiate the stairs from
my 3rd floor apartment, but as I eased my way into the driver's seat for
the trip to the party, I blew out my side-zipper!

Between that fashion faux pas and my rookie makeup job, my confidence
wasn't soaring, but my unexpected girl-look was well received by
my friends, and it was a fun evening!

Sandy

[Jenniferathome]

My first time out, where I had to interact with the normals, was with Allie and Rachael from this forum. I kind of invited myself and we went out to dinner. Having them at my side made it really easy. I was super nervous in the hotel room getting ready and then on the elevator to the lobby. But once we were out and in the real world, it was nothing. I forgot I was dressed.

We've all changed a lot!

[Donnagirl]

My first time out was the Seahorse ball in Sydney. I was staying at the hotel hosting the ball for work purposes and was terrified. I needed physical assistance to step out of the hotel room door.

[kavyaruma]

My First outing with Wig and brave enough to show Sarika was in 2009 to McDonald visit . It is kind of after Halloween and office rush hours , on the way to Garden state plaza @ Nj which is my favorite Mall with friendly SAs . It was a nice experience with a GG commenting i was l a Girl and had hour length talk . I have posted in sissy school forums around that time without my face and now i lost original pic but you can see my face in my recent pic sarika1.jpg sarika2.jpg

[Helen_Highwater]

Over the years I'd been out to public places initially at night but then later in daylight but I wouldn't count these as what I'd class as my first real time out. That was to a support group meeting held in a small hotel. Leaving the car and crossing the car park I can remember the feeling of butterflies mixed with a determination to see this through. Opening the door into the hotel lobby was the first time I'd been into an indoor public place. It had a marble floor so yep, my heels clicked as I walked in. I can remember telling myself to act naturally, remember the advice and own it; and remember to breathe. It's surprising just how much tighter your corset suddenly feels!

The meeting room was downstairs so I navigated those as any GG in heels would, with great care. Reaching the bottom I was faced some 10-15m away by a member of the hotel staff, who smiled and directed me to the meeting room. The walk down that short corridor seemed like hundreds of yards before I turned the corner to face into the room. I paused for a second to to to take it in and recall that no-one gave me a second look, no stares, I was just another person attending the meeting.

I sought out the group secretary to say my hellos struggling to know what sort of voice I should be using. I don't think I've ever been as nervous when making an introduction. As it turned out all there just used their normal voice and that made interacting that much easier. It also made it easier that the secretary was way taller than me so I wasn't going to stand out height wise. Nerves soon calmed but again I remember it feeling a little surreal when I went to the bar to get a drink and interact with the waitress. Was I really doing this? I remember wondering what was going though her mind when she served us. Did she find it weird or really didn't care?

The evening passed too quickly, time to leave. Said some good nights as I walked down the hotel steps and across to my car. Once in the car I sat there for a few seconds, drew a deep breath and felt really pleased and I suppose a little proud of myself that I'd done what I set out to do.

[Janet161]

Wow! Great thread! This is right up my alley. Ha ha. So here goes. The first time I actually went through the whole process of head to toe dressing, wig, make up, etc. I absolutely knew that I had to go out and see and, more importantly, be seen. I had picked out a spot in Austin called 'Bout Time. It was 1995 and this place was super divey with a gravel parking lot. However, it was also a tranny paradise.
Now I came of age in the late 70's-early '80s so I wasn't going to be rolling out in some soccer mom outfit. I had a red leather skirt and matching jacket I had gotten on e-bay. It fit perfect, like destiny or something. Matching pumps with 5 inch heels completed this "screaming for attention" outfit.
I had found a fairly simple makeup routine that consisted of foundation, eye liner and mascara, blush and lipstick. It was great more my lack of skill and patience. Topped it off with my almost black bob with bangs and I was ready to walk out the door of the nearby Ramada Inn. Interior doors so I was going to have to walk down the hall. What if someone sees me? Yikes. I cannot explain the force that was pushing me out that door but I know that it was strong and irresistible. Oh, and one other thing, before I left I literally doused myself with Giorgio of Beverly Hills. My fav fragrance.
So I get there and find a parking spot as far away from any other car as possible. Then I start negotiating that stupid gravel parking lot in my silly high heels. As I am trying to maintain my balance an Austin PD car rolls through the parking lot. Seriously? I'm thinking, Oh my god, the tranny hooker is going down before she even sets foot in the bar! They kept on going and didn't bother me. Phew! So, into the bar. Super divey. Yes I got some stares but ok. I had to order a drink. So I ordered white wine (isn't that what girls drink? I now know that girls drink what I drink) well, they actually had a white zin, a little sweet for my taste but I wasn't there to drink. So the bartender called me sweetheart and lit my cigarette for me-yes, you could smoke in bars then, and I was smokin'-haha. I met one lady like me. She was totally sweet and I had fun talking to her. Met a few nice admirers and was amused by a group of guys looking at me from across the bar with that, is that a guy? look on their faces. I got out my compact to look at myself like every 5 minutes. I was totally digging this. As closing time approached I was sitting alone at the bar and when I stood up to leave I realized that I was surrounded by like 4 guys just standing there staring at me. Go figure. Anyway, off I went back to my room where I was absolutely delighted with the evening.
So now, 20 years later. I wish I could say I've grown up and can hang out in a coffee shop in a smart business suit making small talk with muggles, but alas, I'm not there yet. So if you are in a gay bar in San Antonio or Austin and you see a silly girl in a skimpy top and a bright colored mini skirt and you catch a whiff of Giorgio, that'll be me. Stop by and say hello.

[Paula_56]

I approached the cosmetics counter at Lord and Taylor trembling inside asking for a foundation to provide good coverage. The first woman I spoke with directed me to the NARS counter. At this point I thought “oh no they are freaking out”, but the young woman I met Kasey, was polite and helpful. Over the next few months I would come back to build my needed stock of make-up. Each time she would teach me how to use the cosmetics and also encourage me. We had some in depth conversations about transgendered people and the world. During this time she would extend the repeated offer of a make-over. Now back 10 months ago I never would have dreamed of going out in public and getting a make-over. But over the last year I started to get my proverbial TG wings and have stated going out regularly.

So yesterday was the day, I showed up at Kasey’s counter where she greeted me with a smile. It was surreal to be sitting there, in the make-up chair, having all my life walked by watching with envy as women were getting make over’s. The make-over took about an hour. Kasey gave me some fantastic tips, each step of the way. I have had make over’s before but they were always done by TG artists, the look was ultra glamorous. I have always wanted to find a professional look, suitable for a transgendered woman like my self. Kasey did it; I loved the sophisticated but subtle look she gave me. I took a walk around the mall and felt like a princess. You can see the picture on my Flickr page.

After the make-over I headed out to the Paula Young wig’s factory store.

The women there were friendly and helpful, after awhile I was trying on dozens of wigs off the showroom shelf and finally wound up buying three. We has some great conversations, the women were asking me all about, why, how long, and where about my dressing. They gave a complements on my outfit. It was great to talk openly about so many things I have held inside for so long. There was another woman there, a customer, who was helping me pick out wigs and helped me style them. We sat and had some deep conversations about her life, her gay brother and my transgenderism. She kind rattle me when she told me that I make a great women, and she hoped someday I would seek re-assignment, since it was obvious that I was really a women. I have always considered my self a cross-dresser and her saying this kind of messed with my mind. When I was leaving I told the SA’s, “I never thought I say this but I can’t wait to get out of these heel and pantyhose” They laughed hysterically and said “Now you sound like a woman!”



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[michelleddg]

Holy Moly! Think back to 1980, those of you who can. I had begun my corporate career 18 months earlier, just met my future bride, and was on a 3 week assignment in London. I brought my stash, of course, and fiddling through the magazine stands found a meeting for the London equivalent of Tri-Ess. I packed my stash and took the tube over to the meeting, wondering all the while whether I had lost my marbles. Dressed and made up at the meeting and emerged. A starlet is born! Don't recall much other than being pretty darn self conscious and uncomfortable. I decomposed and actually accepted a ride back to the hotel from a fellow attendee. Yikes, wouldn't do that in this day and age.

That was my last appearance for 23 years. Yes, I've stepped it up a bit since then :-) Here are photos from 1980 and 2015. Hugs, Michelle

[AllieSF]

Oh shit Jennifer, how we have changed! Thank God I was more concerned with getting out and enjoying myself than mastering the art and science of looking like a woman! Otherwise, I am not sure if I ever would have ventured out into the real big bad world. Naw, I would have done it anyway.

[CindyB]

1977 -- my senior year of high school. I was concurrently enrolled in high school and the local university. I had Monday and Wednesday afternoons free as I didn't have any classes. Would spend those afternoons dressing. One day I finally ventured out to local convenience store.

Didn't have a wig but my hair was long enough to curl. I shook the whole time. Had a man hold the door for me. Cashier never blinked an eye. Nervous wreck and I rushed home afterwards but it was thrill of my life at the time. Oh, and this was in a small Texas town where everyone knows your name. Still can't believe I did it.

[Jenniferathome]

Oh shit Jennifer, how we have changed! ...

Yeah, I'm guessing we just failed to notice the stares;-) Great time though! You have start somewhere...

and I am forever thankful to you

[Claire Cook]

Isn't it interesting how well we remember that first time? Here's mine -- maybe 40 years ago. Don't know why I did, just had to. The wife was on a business trip. I had this old ratty wig and a padded bra (my first purchase...) so I just decided to take a bike ride to the mall. I'm sure I got stares from the neighbors, and didn't have to nerve to get off my bike, but I did it. Back in the closet for years ... then it was maybe 25 years ago that I made contact with a sister in Melbourne Florida. Our first stop was a beauty parlor -- a first for me -- then lunch. Sadly I've lost touch with Michelle -- but Michelle, if you are lurking on this site, that day -- with all of your tips and encouragement -- you really made Claire see herself, and I've been ever after grateful. I've never looked back,

[sara.rafaela]

I think I have told my first time out story before. I would like to tell the story of the first time out under pressure. This was maybe my 20th time out. This was still early for me and I tended to dress while traveling only. My usual destinations were gay bars or transgender bars. I usually picked a hotel like the Hampton Inn, Holiday Inn Express, etc. I could get a room on the ground floor near the rear exit. I could then park near the exit. Leaving my room then became a short dash through the hallway to the stairwell, then out through the ground floor exit to my car, a few meters away. I could completely avoid the walk through the lobby. This was always stressful. I just did not want to be seen by the everyday public.

Open the door, check the hall. Step out, keys and hotel key in hand, in case I needed to dash either to the car or back in the room. Get to the stairwell. Look out the little window. Is anyone out there? Dash to the car.

On this occasion I was headed to a Latin night at a gay bar. There is always I high TG attendance there and I was looking forward to it. I was wearing a sequined mini skirt, black top, and 4 inch pumps. I was ready to go. Unfortunately, this time, there was a pickup truck, parked next to my car, and four rough-houser guys seated on the tailgate with a 12 pack of beer. I could see them from the window of my room. They were probably a construction crew, staying at the hotel, just back from a hard day on the job. I decided to turn on Law and Order, watch it for 20 or 30 minutes. They would be gone and I could make my exit in peace. 30 minutes later and they were still there. I was tired of waiting and I decided to to for it.

I found a simple maxi skirt and slipped it over my mini. I put on a big pea coat. I put my pumps into a tote and put on some plain flats. I put on my biggest sun glasses (it was night). Then I walk out, like I owned the place, past the dudes, got in my car and drove off. I must have passed within a foot of one of the dudes. As I drove off I looked in the rear view mirror and the guy was in the middle of the driveway of the hotel pointing at me. This made me laugh inside. I made their evening.

[silkycdresser]

The first time I went out fully en femme was a year ago, in a city in the north west of the UK. I got dressed and put makeup on at home, ran out to my car, drove to the city, parked up and sat there for 30 minutes or so, then plucked up the courage to walk around the city completely dressed as a woman, amongst the commuters walking to work. Ok, I wore a hood as it was lightly raining, but it was a huge step for me.

[Charlotte Williams]

Well my first time out cherry was popped last night! Thanks be to the wonderful people of Detroit's TG Invasion for throwing a wonderful get together and being so friendly

Long ago, I decided I wanted to go out and experience an atmosphere of acceptance; surrounded by fellow CDs. My job takes me around the country, so I was hopeful to be in the right place at the right time for an event. That never turned out (because I invented excuses) and I finally gave up on the idea. As luck would have it, I ended up talking to someone on Friday who decided to start CDing recently and was heading to Detroit on Saturday for the final day of the Invasion. I immediately was intrigued and thought that if ever there was a time to go, this was it. We agreed to go together, then planning mode set in, followed by panic..

How could I get away?
Where would I dress?
Holy $@%&!.. what am I going to wear!?

I looked online for inspiration, and checked out past photos from tgdetroit.com to see what the dress styles were. Into my closet I sprung, then through boxes of clothes and dresses. Nothing seemed to fit right or be what I wanted to wear. "I should give up, this is stupid, I don't have anything that will work..." Luckily my friend messaged me and was heading to Janet's closet to grab a dress. I told myself I needed to snap out of it, that I'm going one way or another. I found a back up outfit of a cute skirt/top hiding in a box, then headed out shopping to find plan A. I found quite a few dresses that would fit, but nothing screamed at me until I found this cute/sexy gray dress that covered my broad shoulders and made me feel great. Time to accessorize...

Back home, the magic of the moment was fading. It wasn't going to be easy to get away (I'm still closeted). "This is too difficult, give up!" - my brain kept shouting at me. I struggled finding any jewelry I liked rummaging through the minimal collection I had. Some would work, but if I was going out, I wanted to look good dammit. Back to the store...this is getting expensive $$. Found it, want it, bought it !

Back home, family friends stop by and I cant dodge them so I can't get ready or at least shave. Finally they leave, and I get ready as much as possible then head to my friends house to finish getting ready and go together. I get there and my friend is fairly intoxicated already and doesn't want to go. She also wants me to stay, which sounds nice at this point. Free booze, great company, and much easier than getting to Detroit. Time passes and I realize that my time in Detroit and my dream of being out dressed is fading quickly. By the time I get up there at this point I'll only have 3 hours until the bars close and the party is over. Cue internal struggle...

#$%& it, I'm going - no matter if I'm only there for 5 minutes, I'm going!

Now the drive... the long quiet drive, alone... with every thought in my head telling me this is stupid. My stomach is churning, I feel ill. My GPS takes me to the wrong place (maybe this is a sign), I have to pee

I made it, I'm at GiGi's. They are packed. A man asks me for some money to park and tells me the show is getting started so hurry inside. I forgot my makeup was on. I just talked to someone, face to face. Don't panic. Switch clothes. Put on your heels. Check makeup. Check makeup again. Grab purse. Check contents. Dump everything out of purse, put almost none of it back in. Get out of the car. Wait no, there's people. Of course there's people, what do you think public is..!?

I get out of the car, keep my head down and make my way to the door. The woman inside wants money and my ID. She looks at it and doesn't care what it says other than determining that I'm over 21. Great, I'm inside now...get out of my way people, I need a drink.

At the bar I'm able to stop and take everything in. I made it. I'm out in public, at a bar, ordering a drink. This bartender sucks, what's taking so long. Clearly it doesn't matter how I dress, I'll never get a drink fast at the bar, lol. The guy next to me wants to talk, and he's surprised to find out I'm not a woman. I'm flattered, but it's midnight and he's drunk - I'm sure he uses this line all the time on everyone in here. Maybe not, who knows. I finally get my drink and head over to the dance floor, but I stand off to the side. Turns out I'm a wall flower in both guy mode and apparently en femme as well. I take note that everyone in here is seemingly having a good time. There are plenty of CDs throughout the bar shooting pool, drinking, conversing, dancing, smiling, laughing. I made it, this is my happy place and obviously many others' too. I try to find out who's responsible for the meet up and am told her name is Samantha, but she's not around.

In the meantime, I check out the drag show downstairs. I get hit on until he is distracted by the queens when they come out after the show. They are gorgeous, of course. Heading back upstairs I get groped on my way in as some guy "accidentally" fell into me. I get it, you're not slick (boys are icky). But hey I understand, I'd be confused looking at me too. Another drink and back to my corner. Ultimately, I muster up the nerve to get on the dance floor for a few songs before the bar closes. It gets hot quickly out there, and dancing in heels is quite the workout. The night winds down, but I don't want to leave. I decide to rest for a bit and grab some water at the bar. Closing time nears and I'm joined by a few from the Invasion who introduce themselves and discover that this is my first time out in public. They congratulate me and invite me to contact them in the future. Samantha is there and I hug/thank her, it's time to head out.

The drive home is filled with the feeling of accomplishment. I finally made it out. I even went through McDonald's drive through trying to get some food, because I was super hungry and over the fear/care of anyone seeing me. It's a great feeling to have and very freeing. I think that's what I'm most thankful of.

Today I'm melancholy for reasons I cannot explain. Maybe I'm over it and wont ever go out again, maybe I'm sad it's over, maybe it wasn't what I expected, maybe I'm just tired from only getting 3 hours of sleep..

Regardless,
TL/DR: Went out last night to GiGi's in Detroit; had every emotion run through me. It was difficult to get there both mentally and physically. Had a blast...totally worth it!!

[Krisi]

I can't really define my "first time out". I suppose it was back in the days when all I had was an old bra and water balloon breasts. I put the bra under my shirt, took the balloons in a bag and got in my vehicle and went for a drive. I stopped and put the balloons in my bra.

Years later I bought a costume wig and did the same but with one of my wife's blouses (at night). I got out of the car in a deserted parking lot and took some photos.

Eventually, I got real forms and padded panties and a real wig and clothes of my own and went out in the daytime away from my part of town.

So, no "first time", I snuck up on it.