MY FIRST MAKEOVER
This is a recollection of one of my most memorable days 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 stocking…..it was all amazing and felt so nice. I was always looking at women and girls around me, whether in real life, magazines or TV and was enthralled when they were wearing nylons, tights or hose. I did not progress in 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 21 and had a job I got to grow my collection and opportunities to dress. I did have a girlfriend then who knew I loved the look of pantyhose and nylons, but not 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 crossdress. 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 where 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, 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 2 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 3 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 to 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 2 days and I had the 3rd day just for me. I wanted to get my nails done earlier in the day since my appointment was for 3 o’clock and I wanted them to be nice a dry. I had a bit of 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 roll and go for it. I had some white girls 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 lip stick 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/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 30s and was attractive. She looked me over and commented about how pretty nails were and lead me to a room wear 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 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 30 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 women.
The first step out the door was the most scary, 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 4 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 am getting in a guy walks around the corner and follows me in.
I hit my floor number staring straight ahead while peeing my panties from fear. He asks me to push the 4th floor (I was on 3rd) 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” and 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 3rd floor and he say “its 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.
OMG I was so nervous and wanted to run away but also wanted to take a bunch of more pictures of myself while dressed up and looking the best I ever had. Since he was coming back in an hour, I quickly setup my camera and started to take a bunch of pictures of myself in different poses.
I felt like such a girl doing this and would take like 20 shots and then quickly look them over and see what I could change to look better. I finished up and was so happy with the pictures that I almost forgot that a guy was coming over! I put my stuff away and went to the bathroom and touched up only my lipstick since I did not want to mess up the makeup and made sure my wig still looked good. I walked out of the bathroom and heard a knock on the door which got my heart racing.
I opened the door and he walked in….we did not know each others name so I reached out my hand and said, “Hi I am Jaime,” and he replied, “Nice to meet you Jaime, I am Tim and I must say you look lovely, did you just get a makeover?”
“Yes I did, it was my first one ever and if you did not guess I am a crossdresser.”
“Well you look great and did think you were but I have to say you look great….. and I do have a bit of a thing for crossdressers but I have not ever explored it.”
I smiled at him and he came into the room and put the wine down on the table, he began opening the wine and I sat down on the bed and crossed my legs while feeling more nervous then I ever had in my life.
“I have never had anyone see me dressed until today and you are the first person to see me like this, except the girl that did my makeover.”
“Well thanks for inviting me over and I was excited that you agreed to have a drink with me.” He handed me a glass of wine and he sat down next to me on the bed. I had never felt like this before in my life, it was such a different feeling to have someone paying so much attention to what I did and said, and especially how he looked at me.
He was a nice looking guy in his early 30’s and in good shape, with brown wavy hair, and nice brown eyes. I would notice him glance at my legs everyone once in a while while we were talking and I made sure to touch my legs and cross and uncross them a few times for added attention.
We talked about how I started dressing, how often I dressed, and what I did when dressed; then I asked about him, why he liked crossdressers and was he gay or bi. It was fun playing the feminine role I was really enjoying it and I was starting to like Tim as he was easy to talk to and was very attentive. We drank more wine and were getting comfortable with each other, when he said I was such a girl after I spilled a little wine on him accidentally and I said “well I am really trying” and we laughed together.
As we were laughing he reached over and touched my thigh lightly, which felt amazing on my legs through the hose I was wearing. He leaned in, and I did the same, opening my mouth slightly and felt him kiss my painted lips softly. I was so excited and just loved being kissed like this as he continued rubbing my legs we kissed more deeply and passionately.
The kissing continued and then I reached over and felt him for the first time…..I always had dreams of doing this one day and could not believe is was happening or at least I hope would be happening. He was hard and it felt like a pretty good size, and I had a feminine feeling inside that his hardness was for me and how I looked, which really turned me on.
I rubbed him through his pants as we kissed and as he continued to feel my legs and reach under my dress. I stopped kissing him and looked at his eyes and asked him if he would do me a favor. He said yes what, and I replied I have always wanted to give a blowj*b when I was dressed and was hoping I could give him one.
I really do not know of any guy that would turn down a blowj*b from a girl, but from a crossdresser was a different story.
He said if I wanted to he would definitely take one from me and then he asked if I had done it before. I told him not with a real one. I went to my makeup bag and got some lipstick and applied it to my lips then sat on the bed, crossed my legs and asked him to stand up in front of me. I reached up and undid his pants and let them slide to the floor, then pulled down his shorts and touched a real co*ck that was not my own for the first time in my life.
I was watching my hands with my long painted nails touch and feel his hard and growing co*ck. It was such an erotic site and feel, I was amazed that it was me that was doing it. I held him in my hand and wrapped my fingers around it as I stroked it up and down. I pulled him close and leaned into him and was face to face with my first co*ck ever. It was a pretty co*ck, about 7 inches long and he kept himself neatly trimmed and had smooth balls. I looked at it closely as I stroked it and glanced up at Tim who was watching me with an eager look.
I bit of precum had formed on the tip as I leaned in and kissed the head, I had finally tasted my first co*ck, it was wonderful. He was very clean and had a nice manly scent and I started licking and kissing his co*ck with my tongue and lips. I got back to the head and opened my mouth and wrapped my lips around the head. I was keenly aware that I just became a co*cksucker, but I just felt more and more like a real girl, especially
knowing I was getting a guy hard with my lips. As I took him in my mouth I heard him moan and tell me how beautiful I looked and how nice my lips felt. I have watched girls giving blowj*bs on videos before and for me the most erotic were the slow methodical ones which I started to perform on Tim. I took him down slowly and tried to go deeper and deeper each time.
After several slow plunges I would let him come out of my mouth and would lovingly lick and kiss the big swollen head. Based on his comments I was doing a good job, as I heard him moan and gasp, and say that it was so amazing and you look so hot doing that. I continued sucking his co*ck and was getting such a strong feminine feeling inside of me, knowing that I could please a guy and make him hard and excited for me was such a turn on.
I wanted this to last so that I could fully enjoy the feminine experience of being a women and giving a blowj*b. I continued my long and slow plunges on his co*ck for several minutes but could tell that Tim was starting to peak. He started to pump himself into my mouth to match my head bobs which caused me to end up going even deeper on his co*ck. I got used to his head hitting the back of my throat and was able to take all of him in completely. I was holding his hips and guiding him into me and held him there when he was at his deepest.
It was then I felt the start of his org*sm, his co*ck seems to grow in size and felt more firm as he pulled out a bit from my throat he moaned deeply and the first spurt of cum hit the back of my throat. It was a bit of a shock but I was very focused on his co*ck and wanted to make sure I finished this blowj*b like a real girl.
Tim’s co*ck pumped stream after stream of cum into me and I kept my lips tightly around his co*ck. I do not remember how many spurts came out but I held it all and started to swallow it as his org*sm eased. It took a couple of swallows to get the mouthful of cum to go down, I continued bobbing on his co*ck making sure he was completely done and I swallowed the remaining cum that was in my mouth. As I let his co*ck slip from my mouth I leaned backed, looked up at him and said to him, “Oh my gosh I swallowed it all!!”
He looked down at me smiling. “That was amazing, was that really the first time you have done that?”
“Yes is was but it will not be the last…..it was the most erotic thing I have ever done.” He pulled me up from my sitting position on the bed and kissed me. “Well I would love to be the one getting more of them and maybe a whole lot more.”
I smiled at him and said, “Well I maybe I can be here for another night.” I gave him a big kiss and I walked him to the door and we exchanged phone numbers. He told me he would call me tomorrow and we would get together if I could stay in town.
After Tim left I went to my makeup and again added fresh lipstick and fixed myself after my activity. I looked at myself in a long mirror and was so happy with the feminine appearance. I lifted up my dress and took out my own co*ck, and got hard immediately just looking at my self and thinking about what I had just done. I sat down and started to touch my legs and I came, without even touching myself. It was a complete shock but was one of the most intense org*sms I have ever had. I cleaned up and drank some more wine…..and started to think about what I could wear tomorrow.
Also read:Sissy kink Stories
Pages: Page 1, Page 2
