Were you nervous the first time you crossdressed?
I’ll never forget my first time going out crossdressed, even though it’s almost eight years ago now. I had been dressing at home for many, many years and underdressing as often as I could, but I had never been out ‘en-femme’ before. A few weeks earlier I had joined a local crossdressing group and had finally plucked up the courage to attend a Tri-Ess meeting.
In my infinite wisdom I thought it would be a good idea to go out crossdressed for the first time. I was conservative in my femininity – I wore a blue blouse over some slightly feminine jeans with a bra for my breastforms and just a dash of makeup. With trepidation I exited my apartment, eager to quickly make the trip down two flights of stairs to my car without being seen. Then as I step foot into the parking lot I’m confronted by
Cops, everywhere – and they’re after crossdressers!
And I’m dressed. They’ll notice my boobs and my feminine blouse. Oh God! Now I’ve gone and done it I knew I shouldn’t have dared to venture out crossdressed. I almost died of embarrassment right there. I knew I was going to get into trouble, or at least a stern rebuke.
As it turns out, the police officer wasn’t outside my apartment waiting for crossdressers and he didn’t pay me much mind. I got into my car without any problems, and was off to my first Tri-Ess meeting.
Over exaggerated fear of what will likely never happen. That’s what I experienced the first time I went out crossdressed, and I have a hunch that I’m not alone. Our worst fears rarely come to pass yet we spend so long dwelling on them. It’s only when we’re out in the moment that the fear can be replaced with the joy of expressing one’s feminine self.
Going Out Crossdressed For the First Time
A few weeks ago I was blessed to take my good friend Vicki on her first crossdressing expedition into the cisgender world. She had visited the Emerald City (a local transgender club in Seattle) before, but leaving the safety of an understanding transgender group was new for her. We started out the afternoon with lunch at Chinese restaurant that we had all to ourselves, and despite some interesting smiles from our hosts it was a great way to ease into crossdressing in public.
Vicki truly showed mastery of her nerves when she suggested a quick trip to the mall together. Dining in a deserted restaurant is one thing, walking through a crowded mall is quite another. It was wonderful to see the sense of joy and accomplishment in her face as she took a proud step forward into the world as her feminine persona.
What was you first time going out crossdressed like? Was it nerve wracking, exciting, joyous, liberating or something else entirely? I’d love to hear, comment and let me know.
This is the site I’ve been desperate for! You seem to have many answers that I’ve been asking for; only I’ve been asking empty space, not knowing where to look. Thank you for being here. Leah
At this time I went to meet a friend crossdresser. I had to travel on the toll roads and yes the blood was running . I became more at ease when I went through a few booths . It was a diffrent way of life. would I go out again. Yes but I would like people to see there are people out there that are not trying to do anything wrong we just want to blend in too. Help us if you wish. Or leave us alone let us live are lifes are way as long as it isent getting into your life.
Wow, the first time out, I do remember it well. I was 14 and how thrilling it was. Like most of us I started playing around with girls clothes and shoes at 11. I would try on my mom’s high heels and walk around the house. That sound that they make is so exciting. At 12 I was invited to a costume party by my cousin, She asked me to come as a girl. I told my mom and she went out to get me what I needed. It was a simple outfit, a blue party dress, white stockings and black maryjane flats. A little makeup and I was set. It was fun and it started to sink in that I really liked looking like a girl. My mom who always wanted a little girl was more then pleased. A little time went by and I would continue to wear her high heels at home, but the feelings were getting stronger. I told my mom that I wanted to do this more and she said she would help me.
For my 14th. birthday to my surprise my mom bought me my first total all girl outfit. What a thrill it was. A red and green pleated skirt, a red wool vee neck sweater, a pair of 2 inch black pumps, light tan hose and a beige bra and panty set, a pair of gold earrings and a pearl necklace. My hair was pretty long so she added a false ponytail. now comes the best part, becoming a young girl. We planned on going out Saturday night as mother and daughter. She did my nails in red, made forms for me using beanbags so it looked like I had real breasts.I got into the panties and bra put on the stockings and heels then the skirt and sweater. She did my hair and put on just the little makeup I needed with some red lipstick. We added the jewelry and got set to go out. I looked in the mirror and thought, wow, this is really me.
We got into the car a drove to a local diner for dinner, I was a little scared, but, my mom was with me and she said no one will know that your not a girl. Nobody at the diner knew and we had a great time. We drove to the movie, and by this time I was feeling very confident about myself. As we waited in line to get our seats two older boys came by and whistled at me, wow, what a thrill, if they had only known. it was a great night that I will always remember. By the time I was 16 I was buying all my own outfits and dressing everyday after school and almost every weekend. I am now 95% girl and 5% boy. I really hope and pray that they never stop making high heels, what would I ever do if that happened.
Miriam
The first time I ventured out as Pippa was while on holiday just outside the coastal town of Ilfracombe.
My wife is well aware that I dress and in fact it is when we’re on holiday that we are most relaxed about it, as there is no fear of being disturbed by any family members. I had already mentioned to her that I wanted to try and capture a nice sunset and as a keen photographer it raised no suspicions of wanting to be on my own for an hour or so.
I showered and put on my undies and a short dress before covering them with my jeans and shirt. I was worried that it looked too bulky but she didn’t notice. After packing a few other things into my camera bag I set off down the road to a discreet pull-in that I had noticed earlier that day. It was on a steep hill leading down into the town. A couple were walking up the hill towards the pull-in but it was a fairly steep climb so I knew it would take them some time to get near me.
Swiftly removing my jeans and shirt I smoothed down my dress and put on a pair of heels I checked my wig making sure it was straight and added a bit of light makeup and my necklace and earrings, the couple were less than 20 metres from where I was parked when I drove away, although they would have still been able to see me as I drove past,
I carried on down the road and took the first turning into the town and was went along feeling really happy to be out driving as Pippa. What I should have realised is that like most towns there are road narrowing places and humps to slow down speeding motorists which meant that I was constantly stopping or going at a crawl giving other drivers and pedestrians time to look in and see me, and I couldn’t believe how busy that sleepy little town had become when the sun began to set. As it was a one-way system I had no option other than go with the flow and I have to say that my excitement did give way to being a bit scared but I have no idea why I was so scared. I eventually emerged at the other end of town and drove back towards our holiday home. By now it was very dark, there were no street lights around and I managed to find somewhere to pull in and change back into my drab clothes and remove me makeup.
I didn’t get any sunsets pictures and made some pathetic excuse about the light being all wrong. I have probably been out driving en-femme thirty times or more since that day and its always a mix of excitement and trepidation. Not quite certain as to why I have this need to expose myself in this way and of course the more we do things the greater the risk of being caught. Pippa
First Time out.
I resolved a long time ago that I was a crossdresser. I had tried, and failed many times to quit. I had accumulated and purged complete wardrobes. I had prayed many many rimes that God take this need away, and each time He answered that His Grace was sufficient. So I finally accepted that I am, and always will be, a crossdresser, and that God loves me just as I am. I have forgiven myself, and now even love myself. So I shopped. As a guy, I would shop the smaller boutiques and clothing stores. Always as a guy. I would always ask if they had a problem with a guy looking, buying, and perhaps even trying on dresses, maybe bras, lingerie. After a while, after I had established a rapport, I would bring breast forms and heels in a bag, and wear panties, bra, garter belt and stockings under my boy clothes. I would arrive just before closing, and they would lock up and let me shop and model what I tried on. I did this at Lane Bryant, Dress Barn, Fashion Bug and some other independent shops. Then I started to frequent the makeup counters at Nordstrom. Still as a guy. I learned my colors and had mini makeovers. Finally it was time. I was invited to a New Years Eve party at a community church which accepts gay and trans people with open arms. I made an appointment at the MAC counter at Nordstrom for a full makeover and an appointment at a nail salon for a manicure and pedicure. I wore a white satin blouse and a black print skirt, long brown wig, light makeup to Nordstroms for my makeover. I arrived at about 3pm. Middle of the day. BRIGHT sunshine. I actually had to step out of the car dressed as a woman! I was terrified. I managed to get into the store and had my makeover. I felt so much better with evening makeup on. I then went to the nail salon where I had been many times before as a guy. When I walked in, the owner asked if she could help me from her station across the room. Then she paused, recognized me, and shouted my boy name across the salon excitedly. I was seated next to a woman I had seen before. She was very impressed and complementary. I finished, went home and changed into my gown. I had to drive 40 miles en femme, wearing 3 inch heels to get to the party. It was fabulous!! There was only one other CD there.
I have other adventures to share.
Danielle True
[...] don’t mean just crossdressing within the safe confines of your own home. I mean going out crossdressed for the first time. I mean gathering up all your self confidence and strutting out the door looking the best you ever [...]
I am new to crossdressing need help
my first time out was on halloween. I drove an hour to our state capitol city. I parked in a downtown parking ramp with a suit case filled with my favorite outfit, makeup, wig and heels.I wore a grey sweater with flare leg jeans and matte black 5 inch heels. A blonde wig with a black beanie hat, and a black purse. my makeup turned out great and I knew I was very passable.I left my vehicle, walked down the stairs and onto the sidewalk. My heart was pounding a million miles an hour.I walked around the capitol buiding where the farmers market was going on. no one suspected a thing. I was so excited and nervous at the same time.It was like being in a hazy dream. The only feeling I can compare it to. is the first time I had sex. The capitol building was open to vistiors so decided to get away from the large crowd of people. I walked down the marble floor hallways of the capitol and my heels sounded AWESOME. I spent about an hour in the building admiring its beauty. I was on the second floor balcony looking up at the massive dome about eight stories above me, when two men in their 30s passed me. They were givng me a good look up and down. I really got nervous. After they passed, I heard one of them say ” WOW,SHE’S HOT”. I knew then, that I had nailed it. I left and went to a lgbt bar I had heard about and enjoyed a few stiff drinks. The rest of the day, I just enjoyed being kaylee. The only bad part of the day was that I got a huge blister on my big toe from my stilettoes.
My first time was in my teens. I had moved and was living with my Father and step-mother. I was given the chores that normally she would do but because they used to get home late almost every day, I became the housewife and Mother to my three step-brothers. While doing the laundry, I discovered that she was my size and I started wearing her clothes (mostly her jeans and blouses). I already had my own undies but I did wear the sexy lace bras and panties I knew she never did.
It was a girl at my school that became my best friend and confidaunt. The first time I met her, she informed me that my bra showed through my tee shirt. After school that day, we sat down and I opened up for the first time in my life to someone else. I was like the flood gates were opened and I was never going to allow them to close. We used to go shopping together, would talk about all the things that a normal teeaged girl would talk about. Yes that also meant talking about dating boys and guys.
It was my friend that convinced me to go out with a guy that we knew from school. I went over to her house, the night of my date and she helped me get ready. I borrowed a cute dress and she helped me with my makeup and hair. It was so wonderful to finally be the true me. It was magical on my date. He treated my like a true woman. All the way up to the good night kiss at the door. I was in heaven.
for some time i have been getting dressed up in my shop after hours and i will jump in the car fast because im still scared, love riding around in the car with a skirt or dress, i have teenagers @ home so i’m not sure yet about going home but the time riding around in public helps, its very exciting ! one of these days i’ll run into a friend to go out with and make it easier>