This is a recollection of one of my most memorable days of crossdressing, it was wonderful.
I started crossdressing when I saw ladies' legs in sheer pantyhose whenever they wore a skirt or dress. I remember being amazed at the softness and smoothness of the nylons and it drove me to try on a pair of pantyhose. I was completely hooked once they slid up my legs and up to my waist. After that, I started to try on other things dresses and heels mainly but also pretty slips and some stockings. It was all amazing and felt so nice. I was always looking at women and girls around me, whether in real life, in magazines, or on TV, and was enthralled when they were wearing nylons, tights, or hose.
I did not progress much with crossdressing as it was difficult to buy and find clothes as a guy without drawing attention, but I did always have a stash of clothes for when I could find private time. Once I finished college, I was twenty-one and had a job I got to grow my collection and I had many more opportunities to dress. I did have a girlfriend then who knew I loved the look of pantyhose and nylons, but she did not know that I wore them or that I dressed up like a girl often. She indulged me and wore pretty outfits with hose often, which I loved.
I had been traveling for work quite a bit and would go to different cities for several days to work and used that opportunity to fully dress. I had progressed to full dressing up which included makeup, wigs, jewelry, nails, and even shaving my legs which was such an amazing feeling. I had taken up cycling and jumped at the chance to shave my legs for the many event rides that I did. Sliding nylons up shaved legs is still a feeling that has no match for me.
My makeup and hair skills were not great but I just loved the whole process and it made my crossdressing sessions long, which I really enjoyed. Guys never really spend much time on themselves that way and it brought out the girl in me to shave my legs, moisturize, paint my toes, put on press on nails, do my makeup, style my hair, pick out outfits, and get fully dressed then take pictures. I really wanted to figure out how to do my makeup and hair better so started searching around on the internet and discovered several crossdressing makeover places in different cities.
I forget which site it was but an amazing crossdressing site had collected all of the places and had reviews, locations, and phone numbers of many different ones. I had a trip down to Houston for work and noticed there was a salon there near to where I would be spending several days. I called and asked if I could schedule a makeover session and talked to this nice lady who booked a two hours session with hair, makeup, and pictures with one outfit change. I was super nervous since I had never been dressed in front of anyone before but booked the appointment. The trip to Houston was three weeks away so I had plenty of time to prepare and get myself ready for what I was hoping to be a great experience.
I wanted to be as feminine as possible for this dressing session so decided to grow out my nails and get them painted at a salon while I was down there, I was going to do my toes as well of course. I was pretty thin already for a guy but wanted to be a bit thinner for this makeover so I started to cycle a bit more and watched what I was eating so as to be as thin as possible. I had lots of dresses and heels to choose from but shopped for some more anyways (such a girl) and made sure I bought some fresh nylons in various colors.
I drove down to Houston and took care of my work which lasted two days and I had the third day just for me. I wanted to get my nails done earlier in the day since my appointment was at three o'clock and I wanted them to be nice a dry. I had a bit of a dilemma in that I wanted a full French mani-pedi but was going to be in guy mode until the makeover. I had decided to just play the feminine guy role and go for it. I had some white capris jeans (previous purchase) and added a black tight t-shirt with some black flat flip flops. I styled my hair in a fem manner, added a bit of eyeliner and light lipstick, and went for my mani-pedi. The girl did my nails and they came out great. I loved being a little fem and chatting with the girl like the other girls in there. No one seemed to make a big deal about me in there so it worked out just fine. I had an hour to kill for my nails to dry and walked around the area near the salon, window shopping.
I went to my car and got my bag which contained the outfits, wigs, heels, etc. for my makeover, and went into the salon. It was a combo CD shop and salon and had clothes, shoes, and accessories up front with the salon in the back. Valarie the stylist came over and she introduced herself. She was a trans girl in her mid-thirties and was attractive. She looked me over and commented about how pretty my nails were and lead me to a room where I could change into Jaime (my girl name).
I picked out a couple of dresses to model for her, a brown tight longer dress, and a flirty black dress with a bit of a plunging neckline. I used a bit of shapewear to get my girly body going, added pretty panties that could conceal myself a bit, and then slipped on my favorite brand of sheer black pantyhose. I modeled both dresses and we decided the black was best, I then slipped into some pretty heeled sandals, added jewelry, and came out for makeup and hair.
Val was so wonderful and chatty the whole time, she even had some wine that we shared which really helped calm my excitement. She explained everything she was doing with the makeup and especially the false eyelashes, which I had never tried before but was amazed at what a difference they made. Once done with makeup she took my wig and did a bit of trimming, adjusting, and styling to make it look right for me. I was done and was so happy with the result, I looked better than I thought I would and more importantly felt very good.
She had me walk around the store and took lots of pictures of me in different poses, standing, sitting, from the back, flipping my skirt up, etc. It was so fun and I felt like such a doll. After all the pictures were taken, I paid Val and gave her a kiss on the cheek thanking her for the wonderful time and pictures. However, I had to face a bit of a problem that I did not really think through. I wanted to go back to my hotel which was about thirty minutes away and take more pictures while I was fully made up and looking my best, but in order to do that, I had to go out in public for the first time ever while fully dressed as a woman.
The first step out the door was the scariest. I heard my heels clicking on the pavement as I scanned around to see if anyone was looking at me and seeing a guy in a dress. I walked to my car, trying to be discreet but also wanted to walk like a feminine lady which turned out to be difficult, I had never had to analyze every step I took!
Well, I made it to the car and slipped in and noticed immediately how much your legs get exposed when getting into a car, I loved seeing it, especially from my legs. I started the car and realized that driving in heels is kind of hard as well, so much to learn! It was dusk and I was driving through some afternoon traffic and was again scared about people noticing me while I was driving. I was also very careful to follow all the traffic rules and speeds as I did not want to get pulled over and have to talk to a police officer dressed as a girl.
I made it to my hotel and then came to the most terrifying part, walking into the hotel and going to my room. I did not think it through that I would need to walk into my hotel and ride an elevator up while being all dressed up. I sat in my car for a while and decided it would be best to go in a side entrance and then quickly get to the elevator and pray no one else comes in. It was one of those smaller hotels with four floors so when I saw that the parking lot looked clear and made my way to the door. I scurried down the hallway as quickly as I could in heels, got to the elevator, and hit the button.
The door opened and as I was getting in, a guy walked around the corner and followed me in. I hit my floor number staring straight ahead while peeing my panties from fear. He asks me to push the fourth floor (I was on the third) and then asks me where I was going since I was so dressed up.
Trying to use my most feminine voice I say, "Just to my room."
He replied, "That is a shame since you look so nice, would you like to get a drink?"
I look over at him and he smiles at me, and I can tell he knows I am a crossdresser and that he is interested.
"Well, I do not really get out much but would love to have a drink if you can bring some to my room."
We reach the third floor and he says, "it’s a date, I will be back in an hour, do you like white wine?"
I replied I did and gave him my room number and practically ran to my room, both from fear and excitement.