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Thread: How was your first time out as a woman?

  1. #26
    Member Charlotte Haynes's Avatar
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    I had a night out in drag over 20 years ago. I was staying with friends in another town, and one of them made me up and lent me her clothes. We hit a few pubs. There was no nervousness, it was just dressing up. I didn?t relate it to my regular crossdressing at all, really.
    The first time out as Charlotte was nearly two years ago. I?d had a few too many shots of Tequila and my partner dared me to go out. I took a walk around the block. I passed a couple of people, but on the whole felt pretty confident. When I got back she said she wanted to go to the local shop (we?d just moved into the area btw) to buy some more alcohol. I suggested we go together. I got my wig torn off and had it thrown to the ground by a fellow shopper. I was ridiculed, threatened with violence, had to take refuge in the shop, while trying to refit my wig, wolf-whistled, and had to endure her hysterical laughter. All in about five minutes. The man in the shop was very sympathetic to my plight the next time I visited in my normal guise.

  2. #27
    Exploring NEPA now Cheryl T's Avatar
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    My very first time in public for others to see was at Halloween as many others have done.
    That took the edge off my nervousness as I could write it off to the holiday without too many questions.

    My first "real" time out was with my wife. We went to a neighboring state to a shopping mall. I was casual, in jeans and a cute top, light jacket and flats. That time I was a nervous wreck. I was sure everyone would be pointing fingers, laughing and maybe I'd even get harassed or beaten up.
    Nothing happened. Sure I got a few stares, after all I'm 6' tall. Any man will stare at a woman who is that tall. After a short while I realized others weren't paying me any attention so I was able to relax and go about my business without fear. A few more times out and I realized the world doesn't revolve around me and that everyone else has their own business to attend to and I'm not a part of that.
    Be confident and present yourself in a manner that says "I belong here". Others pick up on that.
    I don't wear women's clothes, I wear MY clothes !

  3. #28
    Silver Member Stephanie Julianna's Avatar
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    Old story here. 1979, after a makeover by a famous leader in our community in NYC. I was 30 years old and after the session I left his store on West 10th and 42nd Street in a pretty blue chiffon Spring dress and heels. I left about 4 PM and entered the world for the first time as my complete self and have never looked back again. I was and still is wonderful when I get out even to this day.

  4. #29
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    Bit of a back story. My wife who has been living away in Wales looking after her very old parents for nearly 3 years,has given me some breathing space. She does not like me dressing, so with her being away has given me a bit of space. I had done the usual going out in the dark but needed a bit more. So, I decided that I would come out to a very good friend and female neighbour (who liked to do the charity shops and various other shops), that I would like to go with her but I would be dressed as a woman. That is not a problem she said. Well she has the car and also needs a bit of help walking as she has arthritis in her legs plus 2 cancers and a stroke. I was 77y/o when I first started going with her and it was great. I have not had any sort of a problem as I can always pass as a family member or a close friend. I dress for my age as I feel that is the best way to go. I did have a worry when we passed around 200 teenagers coming out of the local Secondary school. Mostly girls, but plenty of boys but not one of then noticed me so I must have done something right. She is my mentor and treats me like real woman which I really do appreciate.
    So last year was a wonderful year for me, but when we go out shopping this year it is just for food so no need to dress up, as we are not out much over an hour or so.
    If any of you girls want to go out in daylight then go for it as you will not regret it. All I would say is do not overdress then you will blend in which is the key to a great journey out.

  5. #30
    Life is more fun in heels Genifer Teal's Avatar
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    Don't put too much stock in the first few outings. They were met with mixed reviews. Once I found the right friends and places to go it got much better. Figure out why you are going out and what you hope to achieve. It can be an emotional time. Best of luck to you.

  6. #31
    Member rian's Avatar
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    In my case i can say that going out is not an option ,,due to the middle east region ,,,almost forbiden ,,,so my choice unfortunately in secret ,,,i love to go out yet impossible .
    Cross-dressing is a cross between woman's soul and man's heart.....

  7. #32
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    You did a wonderful job with your make up

  8. #33
    Heather loves heels Heather2die4's Avatar
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    Hello Gia,
    Metaphorically, the threshold of your front door is the threshold into a new, exciting, and fulfilling world. It can be scary. No, it WILL be scary, but once you get out, there is no turning back. The goal is to look confident and own your space, but you will likely be in your head worrying, so take advantage of summer and COVID and wear a mask and sunglasses to cover the fear. Don't go where thugs congregate. COnsider logistics and plan ahead. If you are not prepared to use the ladies restroom, pee first. Museums are a good bet. Sales staff in any store are always friendly and nonjudgmental. As you build confidence, try a used clothing store. Most have unisex changing rooms and are quite safe.

    My first time was at age 13, just before puberty hit. Such a freeing experience. Sad that I kept it as my big secret for so long. Now I'm out and accepting.

  9. #34
    New Member DanniBell's Avatar
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    I think it's cool how many of you started dressing so much later in life!

    - D

  10. #35
    Reality Check
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    It's hard for me to pinpoint my first time out dressed as a woman. I started by going for a drive underdressed in a bra. Once I got away from home, I inserted water balloons in my bra so I was basically a dude with boobs. Later I graduated to wearing one of my wife's blouses and a cheap party wig, again dressing after I left my neighborhood and just driving around.

    Eventually, I got up the nerve to step out of the car in the dark and walk around a bit.

    Fast forward to today and I've got my own clothes, my own wig, boobs and hips, purse, the works. I still have to dress in the car and I don't get out much but it feels almost normal to be out as a woman.
    Krisi

  11. #36
    Senior Member BrendaPDX's Avatar
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    Hi Gia, I was alone, I was terrified and excited at the same time, my adrenaline was so high my hands were shaking, my breathing was fast, I had to concentrate just to walk. I was wearing a wig (shoulder length), purse, makeup, bra with forms, hip and but pads, pantyhose, knit shirt 3/4 sleeves, skirt just past my knees, and strappy sandals 4" (LOL). Pretty much what I have on in my Avatar, just no sunglasses. It was probably one of the most memorable days of my life. I loved it! Sorry you have to wait so long, but it will be worth it! Take care, and have fun. Brenda
    Last edited by BrendaPDX; 08-20-2020 at 08:51 AM. Reason: Yet another typo

  12. #37
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    Summer of 1998. It was to some LGBT club. Since that is a cliche story, I will talk about my first daytime outing.

    Yeah it was nerve racking. I wore some black top and skirt with a gold waist belt. Heels, makeup, hair done.
    I went to the laundromat to do some clothes then to the grocery store.
    No one said anything or seemed to notice.
    It takes a true Erin to be a pain in the assatar.

  13. #38
    Ah-May-Lee
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    I don't think I had a first time out. The way I dressed as a teen male was not much different from a teen girl. There was not much gender difference being a teen punk. Maybe I wore more eyeliner and lip stick but all the rest was the same, the hair and clothes. People still recognized me. I didn't wear a bra or forms till years later, I thought they weren't the real me. Now I sort of have breasts.
    In solitude where we are least alone. Byron

  14. #39
    Junior Member Lori Anne's Avatar
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    Gosh; it was probably 20 or so years ago, and it was incredibly nerve racking. I wore neutral colored bra (with enhancers) and panties, white jeans, peach colored top, women's sandals, toenails polished, full "daytime" makeup, clip-on earrings, lady's watch, and carried an everyday purse. I drove to one of those mailbox rental places to check my mail, then went to a grocery store and did my grocery shopping. I didn't notice any weird looks from anyone, so I feel like my apprehension was unneeded. I've been out a few times since then, and have had no issues come up.
    Last edited by Lori Anne; 08-23-2020 at 11:32 AM.

  15. #40
    Isn't Life Grand? AllieSF's Avatar
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    I started crossdressing in 2006, and then in May 2007 I found this site. I already knew that I wanted to go out as me, and I didn't even have a favorite name for myself. I decided on a name that was basically a feminization of my true name. That name has now become my legal name, 11 years later. I was reading and learning, actually just vacuuming up all the basic and deeper information here about all of us under the transgender umbrella. Since I knew I wanted/needed a sidekick with more experience than I had, I always looked for members local to me, and even anyone traveling to the area. I finally connected with 2 from this site, RobertaFermina and Windy Cissy. We coordinated when Cissy would be in town and scheduled a "First Night Out" for me.

    That night I put on some thrift store clothes (black top and a pleated patterned green skirt that I still have), low strappy heels, a auburn mannequin bob wig and a short black jacket. We met at an informal computer oriented diner in San Francisco, had a quick simple self order dinner. I got there before anyone else, so I ordered a soda to have while waiting, my first interaction as Allie out in the Real World. After that we planned on going to Diva's, a well known trans bar on 3 floors, with bars on each floor and a different style on each floor. I think that we were out on a Wednesday night and Diva's was dead. So, Roberta suggested that we go across the street to Lush Bar to have a drink and talk.

    There were only a very few people there when we arrived, a little early for the night owl crowd, which was fine for me. There we just talked, drank, talked some more. Cissy showed me how to walk properly, my feet were killing me. I even went to the bar and ordered a round of drinks and ended up staying there a little while talking to the cute female bartender. Writing this right now I clearly see that by talking so long with a complete stranger and having so much fun doing it, was a clear sign of the future for me! I am an extrovert and as my close friends now joke, a stranger is just a friend that Allie has not yet met! We all enjoyed the evening and later said our goodbyes and left for home ot the hotel.

    I can say that I was never afraid of anything. I was anxious and a little nervous about how it would go. However, once there I fit right in and felt so comfortable and thankful for these two wonderful people who let a stranger arrange for all of to meet and go out. Roberta and Cissy were veterans leading the newbie to a new life, which none of us could have imagined at that time. I am now living full time and legally as Allie.

    This is a picture of what I wore out that first night. It was taken several years later on another time out with much more practical, stylish and comfortable shoes and a much better wig, though it does look a little too low on my forehead!
    Attached Images Attached Images

  16. #41
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    First time out was the typical get dressed and drive around in a car for a while. I wore a knee length pencil skirt and a matching patterned tee and a light jacket. It was September near Boston. For my first time interacting with people en femme, I rode public transit into Boston one Saturday in January. I did some shopping and saw some of the sights. Same outfit but with tights, boots, and a heavy coat. It was the coldest day that year. I changed back to drab in my car at the train station. I was so excited and nervous that I barely noticed the chill. Shortly after that, I told my wife about my dressing. That went poorly. I soon purged and got on with establishing my professional career. 17 years passed before I dressed again.

  17. #42
    Member rian's Avatar
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    I only ventured out around the house couple of times at very early in the morning sneaking without any person around ,,,it was a very lovely time ,,because I felt free even to myself ,,,hopefully one day I will have the courage to do public
    Cross-dressing is a cross between woman's soul and man's heart.....

  18. #43
    Aspiring Member dominique's Avatar
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    I started going out just around where I lived. But the first time in public I wore calf length coat,blouse, black skirt, tights and heels. Also some make up. Felt nervous at first but after a while I relaxed and enjoyed the experience.

  19. #44
    Member Dannigirl's Avatar
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    My first time fully dressed with makeup turned out to be a little stressful. We lived in the country, nearest neighbours were quite a distance, and I decided to get dressed up in some clothes I borrowed from my girlfriend at the time. I borrowed a white and pink dress and her white cowboy boots to match. She gave me a bunch of makeup as well. Got all dressed and thought I looked pretty good so went for a walk down our driveway. Got to the end of the drive and figured I would go for a walk across the road on some of the trails in the forest, because that's what all girls would do in a white and pink dress and cowboy boots on a warm summer day right !!!??? Doubt it. Anyhoo, as I was walking towards the gate a pickup truck came up over the hill behind me, turned out to be my friends and their dad heading into town, luckily they flew by me and I kind of turned my back to the road. Phew, dodged that bullet. Decided I better head back home and forget about the walk in the forest..... Half way up our drive and doesn't some guy pull in ! So I started to run up our driveway (it was about 800 feet long and had a bend in it) got around the bend and realized he wasn't coming any further and was probably just turning around. Scared the crap out of me anyway so I went inside and got changed and washed all the makeup off. Had to wash my girlfriend's dress because it was soaked from sweat from all the stress. That is the first time I can remember getting dressed and actually venturing out. Fun times !!

  20. #45
    Member Charlotte Haynes's Avatar
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    I went for a drive last Sunday evening. This was a first, and I would recommend it to others who are a little unsure of stepping out. I had to leave my flat and walk a couple of hundred metres to the car and that was the nerve-wracking part, but once behind the wheel my confidence soared. I felt great. I drove to the city centre and had a stroll around the nearly deserted streets and then back to run the gauntlet of the local neighbourhood. Anyway, go for a drive en femme.

  21. #46
    Junior Member Val_Blackbird's Avatar
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    I absolutely agree with going for a drive. That's what I've been doing lately, since, frankly, there's nothing else to do. It's unlikely you'll be assaulted while driving, and if you've got a deep tint on your windows (I do), it's a virtual certainty no one will even notice what you're doing. It's a nice way to get out of the house en femme with little to no risk.

    I'll tell two stories - one is my first first time out, and the other is my first time out in the general population. They were very different experiences.

    My actual first time out as a woman was, as is often the case, to a gay bar. This was, obviously, a matter of personal safety, even though technically there's still some issues even with that, but still . . . . Anyway, this was just under two years ago, and I hadn't been doing this long. Makeup was questionable, outfit was kinda meh, wig was nice, but not done exactly properly. So, typical, I guess, lol. Oddly, I went to see a drag KING show that night, and there were quite a few more crossdressers and trans girls in attendance than you might think. Nobody really paid me any mind, which was exactly what I wanted. My pink boots did get several compliments, which was nice. Overall, it was cool, which I think is why I started going back basically weekly (usually for drag QUEEN shows) since, up until they black-flagged Earth.

    My first time out in the general population was . . . . TERRIFYING, if you want the absolute truth. It was a Thursday night, and I went to a local tourist area. I knew a place I could park without having to pass through inside, as I worry about what security and surveillance might do if they're paying attention. So, I stayed outside and just shuttled back and forth between the extreme ends of a fairly open area where I could keep some eye on those around me. It was a semi-cool night, so I was wearing a jean jacket over a bodysuit - in part to hide my oddly large biceps - and a pleather skirt with platform high-heel boots. I think the outfit was okay, but the issue was the wig. I like really long hair, and it was kinda breezy that night. So, my hair was just everywhere. I guess the hair and me seeming nervous must've looked weird, because a guy and a girl walked up and asked me if I was okay. I doubt they could actually see my face in the dark and with all that hair whipping around. I didn't want to speak, for obvious reasons, so I just scooted the hell out as quickly as I could. Got back to the car and bounced. It was a long while before I even considered trying that again.

    Anyway, for better or worse, that's what my experience was like.

  22. #47
    New Member Natasha.k's Avatar
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    March 2003 I couldn't take only wearing in private. I said he'll with that. I started wearing blue thong bodysuit, suntan, black or off black pantyhose, short shorts and sandals. Then May of the same year I wore that outfit to my family reunion. Had some questions but nothing bad. Then the end of June 2003. I went to my best friends family reunion. It was huge. I got there and almost drove home to change. I said no. Just go. So I figure get there early. Nope. Everyone was already there. So. I just went over to everyone saying hello. Again some questions. But nothing bad. I had such a great time at the two reunions. I never looked back. My girlfriend doesn't mind as long as when she needs my male self she is fine with it. When I am Natasha I am her BFF. My girlfriend and myself, I was dressed as Natasha took my mother antique shopping. Then went for dinner. It outside under a huge tent. We had a great time.

  23. #48
    Connie Connie D50's Avatar
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    Gia

    If you can get a make over on that day. Unless your wife is great with make up and does it for you. It helps 100% with confidence. Also dress appropriately, for what ever the activity.

    Connie

  24. #49
    Southern Gurl
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    First time out was in June! Yep, thanks covid! Got all dressed up and my wife and I went to a casino. Face mask required of course, and it helped me tremendously. Now is the best time ever, no one looks at your face, just be lady like and enjoy.

  25. #50
    Stand-up Comedian En Fem❤ Alice_2014_B's Avatar
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    My first time out was to the post office at night.
    I wore a wig, shirt, boobs, skirt, and high heels.
    It was super scary, but not all that scary.

    Next thing I know I'm doing stand-up comedy completely dolled up in heels.
    Granted, I do not do stand-up as a woman, though I'm completely dressed up as one.
    I meant all of that when of course the comedy club was open.

    Melissa: "... and why are you dressed as a woman?"
    Coach McGuirk: "Because it's freeing."

    -Home Movies
    (cartoon series)

    Shoe size: 9 US women's.
    Dress size: M to L; 8-10.
    Height: 5' 6".

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