Cindy's Makeover

Cindy's Makeover

CindyUSA

cindyusa58@yahoo.com

Five years ago I was a newbie cross-dresser. Like many cross-dressers I was married and could not dress full-time. My wife did not know of my fetish for wearing woman clothing nor would she ever understand. The pleasure I gained from cross-dressing was mainly from the attention I receive from CD admirers.

It is a known fact that some cross-dresser will pay more attention to woman's clothing, shoes and makeup than the woman tits or gluteus maximums. For me watching a generic women in shopping malls, or in magazines or on TV, was a good way to find out how to look like a woman.

I did my shopping on line buys and could dress and look like a woman: from the neck down. The trick of transformation for me to pass as a woman was in applying make-up to make me look like Cindy. To improve on my skills at applying make-up I decided that I needed make-up lessons. The lesson would allow me to ask all those questions about putting make-up.

I did some research on the Internet and found that London was CD friendly place. My search found several dressing services offered glamour shoots in the London area. Dressing Services provide professional help with your transformation into a woman, whether this is a make-over including clothing, shoes and wig or just added help with make-up. After your transformation you can pose for glamour photographs in several different outfits.

The dressing services had packages that varied from a couple of hours to all-day events. A full day and night CD outing was expensive for my budget. Instead of a professional dressing service, I posted a message on a Cross-dressing website asking if anyone knew someone that provided make up lessons. I received several replies and after comparing prices decided on services of Amanda. She agreed to provide make-up lesson and dressing me up for a glamour shoot for £200. I also asked if she could provide me a traveling makeup kit with make-up, brushes for an agreed cost of fifty pounds.

Now, I worked overseas and traveled every six months for vacation. When I traveled back to the US, I would spend a night in Dubai where I dress up as Cindy. It was 2010 and I decided for my next vacation I would travel to London for a couple days and have my glamour make-over.

I paid Amanda in advance, sending the funds by Western Union. While I was in the states, I went to Goodwill, a used clothing store and picked up a few additions to my Cindy clothing. I found a short red and black short skirt that would just cover my rear. I found several blouses that had three-quarter sleeves, button down the front that could wear with several skirts.

When I traveled I would pack my Cindy's clothing at the bottom of my suitcase, putting my guy drab clothing on top. I did find a long summer dress with a floral pattern, a short knit cardigan that I selected to wear on my first day out in public. I was ready for a makeover and planned to walk public for the first time.

I ordered from the Internet a pair of brown ankle high boots. I needed comfortable shoes for all the walking and standing I would do over the next three days. I would travel with my Cindy clothing packed on the bottom of the suitcase, on top was my guy clothing.

I arrived at London Heathrow Airport at 10:45 on a Monday. I carried a backpack with my computers, cameras, phones and recharges. Clearing customs, I took the Metro from Heathrow to Kings Cross Station, the trip took one hour. On arriving at Kings Cross Station at 1 PM, and took a taxi to the Holiday Inn Express. It was now 1:30 pm, my makeup lesson schedule to start in one hour. I called Amanda saying that I was running late, she said not to rush. I shaved twice once with a new triple edge razor with shaving gel then finished an electric razor. My face was as smooth as a baby bottom with no stubble.

The taxi to Amanda’s house cost about twenty pounds and took twenty minutes. Amanda met me at her door, and what a good-looking woman she was. When I shook her hand I not realize that Amanda was a TV and she was stunning. We walked up to the flat on the second floor. Amanda had a room dedicated for make-over business, with a closet full of shoes, clothing and wigs. Amanda asked me to sit and we had a pleasant conservation about my need to cross-dress.

Amanda asked if I were ready to start my lesson, I said yes. She told me to take my clothes off. I did as she directed, but left on my boxers. She said to remove the boxers too, stating that she has seen many a Willies. I am comfortable naked with strangers, although I have gained a few extra pounds. I have on my chest a large scar from my gallbladder surgery. This scar might appear unattractive for some people and I am self-conscience about how it looks. Despite how I looked I removed my boxes and stood naked in front Amanda. I was ready to start my makeup lesson.

Amanda asked me to put on my stockings, panties and corset, again I did as directed. Amanda sat me in front of her make up table, provided me the traveling makeup kit. She said that she would apply makeup to half of my face and I then would do the other half. We started with the foundation. Amanda had found a shade that matched my facial skin tone. She used white foundation around my eyes and nose to make the area lighter. Using light and dark foundation to highlight the face, contouring my face. She applied the skin color foundation with a brush on half of my face and I applied the foundation with a brush to the other half. Next she blotched the foundation with a wet sponge; followed by a dusting of power to set the foundation. I did the other half with the sponge and power. The makeup made my face look like a woman and fifteen years younger.

Looking into the mirror, I notice the light color around my eyes and the darker color on the rest of my face, I looked like a raccoon. I told Amanda that I wanted to look like a normal woman walking down the street and not the look of a drag queen. I wanted my makeup to make me blend in with the crowd and not draw attention.

Next, we did the eyebrows in brown to match my new wig. She asked if she could trim my eyebrows, saying they were busy and need a few hairs plucked. I agreed. Completed the eyebrows she started with the eyeliner, eye shadow on my eyes. She used a black gel and a small brush to create a black line on the top of the eyelid and the bottom. She then applied a second line above my eye and below the eyebrow created what looked as a second eyebrow. I followed her artwork on my other eye. At first, I did not know how this would look.

Amanda finished the left eye, I finished the right eye. She added some blush to one cheekbone, I did the same to the other cheekbone. Next she showed me how to apply glue to the false eyelash and how to glue the eyelash on. Gluing on fake eyelashes was one of the most difficult things I was taught. It took me several times to get the eyelash in the correct position.

Amanda directed me to look in the mirror. When I turned and looked there was glamorous woman looking back at us, Cindy. I felled in love at that moment with Cindy, Cindy would be my best friend, someone that I could share some wild, sexy, erotic time. My transformation brought Cindy to the surface. Next, Amanda dressed me in my long floral dress that I have brought just for this occasion, my ankle high boots, belt and cardigan and Cindy were ready for a photo shoot.

We walked down stairs entering Amanda backyard which she said was her joy in making it a lovely garden. It was a perfect place to take some outdoor photographs. After enjoying the sunshine and photo taking, we went back to the dressing room where Amanda had me change into a splendid black evening gown with spaghetti straps; reveling in my shoulders and chest. I had shaved my chest smooth. She gave me a black lace shawl, and posed me in several positions taking more photographs. The last change of clothing was into sexy black baby doll lingerie with a plunging neckline showing off my cleavage. I had put on my fake tits 42C and corset. She took more photos.

All this, the make-up, the dressing and photos took slightly more than four hours. Time went so quick but and I had to leave. I loved every minute of the afternoon. Wearing my long dress, I was ready to go out in public. Downstairs a taxi was waiting to take me back to the hotel. The taxi driver did not know the way to my hotel, lost for many minutes and I arrived at the hotel later then I had expected. The taxi driver carried on a conservation without comment about me being a guy in a dress. I might have looked like Cindy but I still had a guy voice.

After my makeover session I had made plans to meet a man from Craigslist. We were to meet at seven pm, I was running late. When I returned to my hotel, I was an hour late. Hurrying back to my room, I set up my laptop hoping to contact my date. Cindy was ready to meet a strange man in my hotel room. The hotel did not have free wireless. You had to pay for the Internet service at the front desk. I called the front desk to order the Internet service and who told me I had to go and pay cash at the front desk.

I had to go to the front desk dressed, no, no this was not what I had planned. I was dressed as Cindy but checked in the hotel under my real name. How could I explain the two different people, what if they asked for ID? After a few seconds of distress, I decided I had to go down to the lobby dressed as Cindy to buy the Internet service. Dressed as Cindy, I had apprehensions. I questioned if I were ready for this. Walking down the street dressed as Cindy was easy, but talking a stranger would be a challenge. I told myself to calm down, I just had to talk to the desk clerk.

Without Internet access, I could not contact my date. I left my hotel room, got in the elevator went to the main lobby. I approached the front desk and waited for the desk clerk to ask me what I needed. I told him I needed Internet access. The desk clerk asked for my room number which I replied to 907. I got a funny response, where the desk clerk said they did not have a 907. He asked for my last name. I give him my real name. Looking up my real name, he said I was in room 709. I was so nervous I gave him the wrong room number. Now he knew I was a guy in a dress. I expected the worst but instead he gave me the access information for the Internet and that he hoped I would have a good night. I did not get any other reaction positive or negative. This is one reason I like London nothing shocks them.

I got on the Internet contacted my date. He quickly responded that I was late. He did not wait for me to contact him. This cancellation was disappointing. My first night in London as Cindy looked like I might be alone. I had a date for Thursday, contacted him, and asked if he could meet me tonight, he said yes. He was younger, in his early twenties. He was younger than me, I was not sure what to expect. He met me in my hotel room bringing with him a bottle of whiskey. We shook hands, and I asked him how I looked. He responded with approval.

We starting chatting to get to know each other. We had a couple of drinks. We chatted about our work and found out we both worked in construction. Within a few minutes the whiskey taking affect, we were in bed, me in only my stockings, panties and bar, and he reviled a trim and fit body of a man in his twenties. Being young, he had a well-defined body, and strong arms. I can say we made passionate sex for about an hour. Afterwards, we relaxed in bed continued chatting just about everything.

I was thinking that he would want to leave but to my surprise that he remained. We made passionate sex again when after we fell asleep, I think it was now three AM. I woke up at seven AM, noticing him sleeping and always wanted to wake someone up by giving him oral. Therefore, I did. He was quick to respond, rewarding me for my effort. He apologized, but said he had to go to work; he dressed; we kissed, and then he left. The photographer would arrive at ten AM. I had time for a quick breakfast.

I was not ready to be Cindy at breakfast. Last night passionate lovemaking and the morning rumpus smudged my makeup. Off came the makeup; on went to my guy clothes. I hurried to the dining room to have my breakfast. Back in my room, Cindy would need to do her own makeup. I tried to remember all Amanda said the day before. Looking at a photograph of my face taken from yesterday, I used it as a template for applying my makeup. After I had applied my makeup, this time Cindy did not look fifteen years younger more like five or ten. I tried to match the photograph, but I just could not get the eye makeup right.

At ten, AM, I was Cindy again and this time dress in my red PVC knee-high 5" heel boots, red and black short skirt and a pull over top. I looked like a hooker, which was the look the photographer wanted. The photographer arrived on time and stated that I was beautiful in my outfit. It did not take long to end in bed where he took a few naughty pictures. The photographer's compliments told me how beautiful I looked, how he liked my body and Cindy was such a turn on. Each compliment he said made me hornier.

We spent the entire time in my hotel room. I had little sleep; with missing a few meals suddenly, I hit a low. I did not feel well enough to go outside for pictures. My next date was to arrive at seven. I removed my makeup, dressing as a guy, I ventured to a restaurant for some food. I was back in my room, refreshed, transforming as Cindy. I dressed in my below the knee gray skirt, white blouse, school tie. My date arrived vocalizing his approval of Cindy the student. I spent another enjoyable night with an admirer. He left around midnight leaving me to sleep soundly.

End Chapter One

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