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I shared my first time crossdressing here – it ended up being a lot more dramatic than I had planned. Complete with a police encounter…
What was your first experience out dressed?
Once, many years ago, I went for a stroll at night, fully dressed. It was very late and no one was around. I saw no one. I guess I just wanted to do it once to say that I did. I’ve never had the courage to do that again, and never at a time when there would be others about. I’m thinking of making an appointment for a femme makeover though. I’m scared. I’m still a closeted CD.
hey there!
Well, this was a few years ago with a friend of mine. Went to a local transgender club near where I live. It was a wonderful experience to be completely truthful. I was dressed in a long black sleeved top and a long black pencil skirt completely with dark-brown wig. Would love to do it again sometime. Hope that helps.
Today I took a small but big step. Got fully dressed, hair makeup etc and went out. Just a couple of little things. Gassed the car up at a packed filling station, and swung through a Wendy’s drive through. Not even a 2nd glance while filling the car with people walking by and filling up next to me. The folks at Wendy’s were very nice although I have to believe my voice was not passable lol. But who knows, the people at the windows were very friendly and smiling so just maybe….. All in all very exciting and nerve wracking at the same time, but oh so glad I did it!
Unfortunately, my first experience out was so many years ago, all the details are fuzzy.
I can recall getting dressed, wearing a brown romper….and having to pysch myself up to get out the door. I remember walking through our back field, into town, and going into Tesco. Then scurrying home….so scared that I had been “Outed”.
Looking back, as I type this, little did I know, but I was already outed.
Cookie 🙂
I know how scarey it is at first girls but once that is behind you it is so much better. Now I love taking my newbie friends from the clubs out in public for their first time and watching their reactions to everything. I feel like a mother escort but love doing it
Mine was with a friend, a girl when we were 12 or 13. Over 50 years ago. We were dressing up and I dressed up in my older sisters dress, it was yellow with some black design on it, and a pair of white cotton bloomers, part of her school uniform. I had a scarf around my hair and her shoes fitted me. It was a fun thing to do but I then wanted to stay that way. My parents noticed that I later collected a few bits and pieces of female clothing like socks and unisex things and they took those away and said nothing. But that started something that has never stopped. Dressing fully as a woman feels more natural than dress as a man now. That first time, when I think about it now, wasn’t hard to do. I saw the clothes there and just dived in. It was like suddenly finding part of me.
My first experience was 30 years ago, when I was 4. It was my mom the one who tried a petticoat on me, I still remember that day. I thought it was too soft, too beautiful, that I couldn’t stop wearing her clothes or my little sister’s anymore!
My first time I went out in public was terrifying and exciting at the same time. I was a teenager and had the weekend alone as all the family was gone. I wore a wig my sister had, a pair of shorts and a tank top with a bra and undies. I had little body hair a the time and had been using my sister’s and mom’s makeup when I dressed at home, and had it down pretty good. I wore a pair of heels that belonged to my sister and had been practicing walking in them for awhile and had that down pretty good too. That night I left out of the rear of our yard so the neighbors wouldn’t notice me and walked down the alley to the end of the street, then walked around the neighborhood to a local strip mall. As I walked past the mall, some guys at a 7-11 started whistling at me but I just ignored them and walked on. Several drivers who passed me honked their horns and stared but kept driving. When I got home my feet were killing me but my heart was pumping and I was so excited. After that night there was no going back. I later realized I was kind of dressed up like a hooker with the short shorts and heels and walking the streets at night so I started wearing flats or sneakers instead.
My first time was when my parents dressed me as a girl on Halloween of all times. I was 11 or 12 and I was in a dress and even had boobs, stockings or something stuffed in there. I was brought to all my parents friends and, no one knew but it was an experience I didn’t understand. I knew I was embarrassed but I knew it was something I couldn’t forget, nor did I ever.
My first real outing dressed (not counting the fetish boutique makeover 20 years ago – was too controlled and fake) was an afternoon tea at a friends. She invited me to attend as Sarah if I wanted. So I turned up under dressed and slipped into a blouse, skirt and heels there. Had about 2 hours of chatting like normal but with me dressed. Was great and seemed so natural. Was worried at first and almost didnt come out when I was dressed but I did and had a good time.
its been wonderful i talked to my wife about telling my 1 daughter out of 3 so far.we invited her over 3 days before christmas and my wife talked to her while i was dressed and hiding .when my wife called me and said its ok come on out i was so excited and also scared of what was going to happen even that i knew it was ok because she said come out as you are.i came out and my daughter gave me a smile from ear to ear and came and gave me a good hug and said i love you and very proud of you.that was a big relief, so she asked me if she could buy me some things and give to me in private and i said yes you can . she didnt like my wig so we sat down and picked out the one im in now and we try to have a girls night once a week.they have been helping me with my makeup and yesterday i was feeling so good that we went to taco bell drive through i ordered and paid for our food as my first time out the girl at the window looked at me and took the money and gave me my change then she went on working and never looked again till she gave me my food i knew then i passed and it was wonderful love you all and thats enough for now xoxoxo
Jennifer and Sarah: that’s awesome for both of you! Yay!
Jennifer, your daughter sounds amazing! And your wife, of course. I hope “coming out” to your other kids goes just as smoothly.
Margie: That reminds me. Huh. When I was around that age, I got dressed as a girl scout for Hallowe’en. We borrowed a friend’s uniform, and my mom did my hair and makeup. I don’t remember wearing a wig, though maybe I did. It would’ve been the early 80s or so, so I had shaggy hair that maybe could’ve been styled a little bit. I haven’t “forgotten” about this, but yet I never really think about it when thinking about when I got started dressing.
Not counting that, my first (and so far only) time was last fat a support group for transgender and CD people. I got dressed there, then changed before I left to come home. The only thing I did in advance (other than underdressing, of course) was I did my nails. And I was certain that everybody was staring at them while I was driving to the meeting. Of course, they weren’t. But paranoia is a weird thing…
I’d love to go out shopping or to dinner. But for now, I won’t be because I’m quite hesitant to leave my house dressed, with the chance of neighbors seeing me.
Oh, my… Ummm… I would have to… ummmm.. well, share the “G-rated version”… *blushing.. because, I don’t think it would be well received on this site. – Going to the Pepperz bar/club was Lexi’s first night out dressed full femme, in Gulfport, FL, ( right next to St. Petersburg) – Pinellas county.
It was one of the best times out to the club, if not the very best time out as Lexi dressed in full femme attire, out of what became many, many outings. I was hooked on going out, after that night.
On that night, it was my very first night out fully dressed as Lexi, heels, pantyhose, bra, the whole deal, in a very short stretchy, mini-skirt.
A very tall man, in good shape, older, and very good looking professional type man, sat next to me on the barstool. He started chatting me up, and bought me a drink right away, like a gentleman would, hitting on a female at any regular type bar or club. He was sitting very close to me and after just a few minutes, started to caress my shoulders, hair, I was sooooo… nervous, but he had a way of talking to me, making me comfortable. My heart was pounding, as he practically started “cuddling with me”. He seemed to be very experienced with “new gurls”. He then started to kiss my neck, and nibbled on my ear.. Oh, that makes me crazy, and he knew it. Then, he took me by the hand… and we… “danced” a little. (edited)He took me by the hand again, back to our barstools, where his friend was sitting also. He then ordered me a shot of tequila, and a beer, then bought me like 6 more shots through the night. We closed the bar, and I ended up leaving with both of them, back to their house, just a few blocks away.
It was amazing. My first night out, looking for exactly what I wanted, and got it beyond my wildest dreams…
I will never forget that night, as long as I live, I am sure.
Wow, that is one powerful first night out. I’m guessing it was a first time with a guy.
Actually, no, Brittany, but first as “Lexi”.. I had a couple of , well, I got drunk, and some guy wanted to “please me”.. with their mouth. I , growing up, here, seem to have had a lot of older men who “wanted me”, as a young man, not dressed femme, and I don’t know why. I did not engage, nor did I encourage them in any way. Just a couple of times, when really, really drunk did I let any of them touch me.
Actually, no, Robin, but first as “Lexi”.. I had a couple of , well, I got drunk, and some guy wanted to “please me”.. with their mouth. I , growing up, here, seem to have had a lot of older men who “wanted me”, as a young man, not dressed femme, and I don’t know why. I did not engage, nor did I encourage them in any way. Just a couple of times, when really, really drunk did I let any of them touch me.
My first time was exciting and thankfully uneventful. I was 14 and my Mother & sister were not going to be home until late in the evening. I dressed up in a wig and stripped dress. Applied some lipstick wore pantyhose slip and bra which I padded. Also wore shoes with heels about 2 inches high. I walked to the bus stop that was two blocks away and took the bus to a mall. I went into one department store and looked at some dresses. An associate asked if I needed any help. I replied I was just looking. After my short excursion I took the return bus trip home. I considered this to be a success but I was scared that I would be recognized or someone would figure out that I was a boy.
I remember one of my first experiences was when I was in grade school. I had a rare afternoon alone without parents or siblings around. I went digging through my mom’s makeup drawer, and found her nail polish. I put clear on my fingers and red on my toes. The next day in school, one of the girls noticed my finger nails. It was clear. I thought nobody would notice. She busted me in front of the whole class. I denied, denied, denied. It felt so good to be busted though!
My first and only time out fully dressed happened at 4am Memorial Day 2019. I had the house all to my self and planned a full fem weekend. For my last fem activity I went for a moonlight walk. I spent the previous hour putting on a black nylon panty, nylon half slip, and padded bra, black nylon and lace trimmed garter belt and lace topped black nylon stockings, and a knee length black dress I’d recently bought. I also wore my wig.
Since it was my first time out; I wore my male black tennis shoes, just in case I had to run back to my car for an escape. I live in the country near two very, very, very small towns. One of the towns has a church with a walking track. I drove to the church and did a 20min. walk. The nightly breeze was so calming on my nylon legs, it felt so natural.
My older sister use to like to play dress up and we lived out in the middle of know where with no kids around. My sister convinced me to play dress up with her. She gave me a matching training bra and panty. With a lovely flower print dress with tights and a low heel shoe. She painted my nails and put make up on me and an old wig my mom had. She then taught me how to walk and sit in a dress like a young lady. We then played tea party and talked about boys and it was a most wonderful afternoon. I haven’t stopped since. I remember that day with fondness.
Thanks
Rosie Beth.
The first time I went I was about 12 years old and I was home alone for the night. I had been dressing for about two years and being so young, I had no real body hair to speak of and young, even feminine facial features. I decided to dress up and wore a pair of white shorts, a black tank top and black platform heels. I wore my mom’s blond wig and I put on my sister’s makeup. I thought I looked really good and decided to go for a walk (NOT the smartest thing I have ever done). I snuck out the back gate to the alley and walked down the alley toward the convenience store. I walked through the strip mall and saw some guys on bikes to the front of the store. I was terrified but I just walked past. I got a few cat calls as I turned the corner and continued down the street back toward home. One of the guys came around the corner on his bike and was staring at me as I walked down the street. Now, it was late at night and I was presenting like a girl in short shorts and high heels (can anyone say hooker?). As I continued down the sidewalk, a guy in a pick up pulled to the curb and rolled down the window, waving me over. I just continued walking scared to death. He eventually pulled away and I made it back home, my heart pounding! One of the most terrifying and exciting moments of my life.
I was 18, just got my own place and was buying and wearing all the wonderful and sexy clothes I had wanted so much for so long. My many dreams and fantasies were about being dressed up as a pretty and sexy girl and going out.
After many failed attempts and chickening out it was time. I got my purse, shut the door and began walking to my car. My stiletto heels were clicking on the pavement. My silky pantyhose was caressing my legs. My breasts were gently bouncing. I could feel the cool air under my dress. My hair gently blowing in the breeze. I was in a total state of bliss and euphoria. This was better than my best fantasies.
Then I nearly walked into a guy walking his dog. Total panic. I wanted to run back to the house but the car was closer. I walked quickly to the car and opened the door. The interior lights cam on, spotlighting my legs in my shiny pantyhose, sexy stilettos and very short dress. I freaked and got in quickly. My heart was pounding, I was shaking, sweating and breathing heavy. I was in near total meltdown. I had to calm down before I could do anything.
After several minutes I figured I would go back to the house. I opened the car door to see if anyone was nearby. I,looked down at my legs. My very short dress was hiked up even higher and my panties were showing. WOW! I looked down at my legs. In my shiny pantyhose and stilettos they looked incredible. These are my legs? OMG! And I showed them to someone. Did he notice them? Did he see my sexy stilettos? Did he notice my shiny pantyhose? Did he see my panties? I began to get real excited. I can’t believe I did that. WOW!
I couldn’t go back inside. I had to drive around some. I waited so long to do this. I drove around a while and stopped in some places I felt were safe where I could get out. I walked close enough to people where I could be seen but not touched. I noticed some looks coming my way. WOW! I’m doing this. OMG! Finally. it was getting late and places were shutting down. I headed home. I was so thrilled and happy. It had been so scary and so exciting. One of the worse and best experiences ever.
My first time was when I was 11 or 12 and I tried on one of my mom’s bras I accidentally found in the clothes hamper. After that first time, I would regularly check the hamper to see if there were any of her bras I could wear. One day she caught me when I had one on, but didn’t make a big deal of it. I of course was hugely embarrassed, but not enough to stop.
Ladies,
My first public experience was wonderful. I went out in a lovely white high-necked flowery dress of my sister’s when I was 14. It was a dare from a school friend, can’t remember how it came up, nothing sexual or gay, just wondered how it would look and would I pass. He said no way you could pass, I said I bet I can. I took the dare, dressed up, socks in bra, a little make-up. I had long hair then and no beard, arm, chest or leg hair growth so that part was easy. I remember his astonishment “You really look like a girl!”.
We went out on the town, again nothing sexual from either side (I am very heterosexual!), just felt good and got nice looks from people. In some ways wish it never ended! We even went to a cafe where I used the Ladies, had a couple of cokes. I wanted to go shopping but there wasn’t really time.
S
Darling Vanessa…
My first outing as Polly was a stroll through our new built city centre with my truly supportive wife, hand in hand(!). Just strolling and taking in a summer sights. I became so embolden by this I risked entering our best known department store to ‘window’ shop. Afterwards we had lunch at a hotspot eatery sharing a table with half a dozen others! To say I revelled in the experience is an understatement… quite frankly my dear… I did give a damn and that has become the pivotal moment in the birth of Polly.
So, no dramatics…Love Polly
I started crossdressing when I was still in junior high school, using my sister’s clothes and lingerie whenever I got the chance to be home alone. I continued dressing en femme after high school and getting a apartment, where I lived by myself and could dress whenever I wanted to. I was what I call a closet dresser. Dressing in the privacy of my apartment and not going out in public. This satisfied me for quite awhile, but time made me feel like I was a prisoner in my apartment. I had learned how to apply makeup correctly and style my hair. I had a nice collection of feminine clothing and lingerie. I learned how to walk in high heels. I would look at myself in a mirror and see a very feminine looking young woman. I knew that I could pass as a girl. I just didn’t have the confidence to leave the safety of my apartment. One day I told myself that today was going to be the day I went out dressed en femme. It took me almost two hours to get ready for my first time out. I was so nervous and excited about what I was going to be doing. I looked at myself in the mirror and touched up my makeup then put my purse strap on my shoulder and my sunglasses on my face, then opened the door and stood there petrified. One of the hardest things I ever did was step outside and close the door to my apartment. I didn’t know what to expect. I had thoughts about being seen as a man dressed as a girl and being criticized. I learned quickly that nobody cared about me or how I was dressed. I was just another girl going out for the day. I was accepted by everyone who saw me and all the fears I had never materialized. I had some confidence that got to be more and more, the longer I was outside among other people. One of the things that I never thought about was the feeling of the light breeze blowing under my skirt and through my hair. These two things made me feel so feminine and girly. Another thing I didn’t expect was hearing my heels clicking on the sidewalk when I was walking. I had only walked in my apartment on the carpet and my heels were silent as I was learned how to walk in heels. Something else I hadn’t thought about was driving wearing heels. I found it awkward to try driving wearing heels. I found out rather quickly that I had to use the side of my foot on the pedals instead of the bottom of my foot. I also learned that my skirt was a bit shorter when I was sitting in my car and I was showing more leg then I thought that I would. The seat belt was a challenge as it crossed over my left breast when it was snapped across my chest. I wondered how woman deal with this uncomfortable situation?. Learning how to get in and out of my car without anyone seeing my panties was something that I had to think about. Keeping my knees together and swinging my legs out or in at the same time was the most ladylike way to do it. My first time out was a learning experience for me. There was many things that I learned that I had never thought about. Learning how to be a girl was one of the hardest things I ever did There’s a whole lot more to it than just wearing women’s clothes and looking feminine. It’s a life changing experience
First experience was when a french exchange student came to stay one time. She was about the same height and size and fortunately left her prom dress out on the bed with me home alone one day. I raided her draw found some stockings, bra and pants and tried them on. Along with the ball gown and her high heels its was a revelation. I probably had 3 or 4 experimetal times before she returned to france. I dont think she was any the wiser!
My first time out femme was during my wifes transformation of me, we lived in San Diego at the time. She picked out a dress, did my makeup and got me ready. It was evening and we went to a strip mall window shopping and some actual shopping. She ended up buying me another dress and a pair of shoes. I was so nervous but as the minutes went by I became more relaxed and really started enjoying the experience. By the time we returned home I was already looking forward to our next outing.
Wow, Bobbi!
If you’re gonna do it, you may as well do it big. And it worked out so well for you, too. Good, girl.
Bettylou
Bobbi… please excuse the colloquialism but… that took balls! Wow… I couldn’t imagine the courage you had/have, sister! I was a whole lot older than you and so gives me the right to say… “don’t confuse me with someone who cares about looking odd!”
I hope you will have a wonderful life even if you may support the Blackhawks!From a Habs fan, hugs Polly
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