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I would like to share my latest cross-dressing experience. Like many cross-dressers, I dress up part-time. I am married. She does not know of my fetish of warning woman clothing. My dressing need stems from my enjoyment of the attention I received from admirers. I was new at this cross-dressing having started dressing five years ago. Many cross-dressers started their fetish when they were young, preteen or in their teens.
As a cross-dressing, I now pay more attention to woman’s clothing, shoes and makeup. I shop on-line and cannot wait for my new buys to arrive. My weakness was applying makeup as Cindy. I only dressed in public two times and paid a make-up artist to make up. Even with makeup, I did not think, I was passable. I decided a makeup lesson would allow me to ask all those questions I had about putting on my Cindy face.
Included with the makeup lesson were glamour photographs of me posing in several outfits. London was the CD friendly place having visited twice in the past few years. I did a search of business that offered glamour shoots in the London area. The dressing services had packages that varied from a couple of hours to all-day events. The cost averages one hundred pounds an hour during the day. An evening outing can cost over one thousand pounds. A full day and night CD outing were expensive for my budget. As an alternative, I posted a message to a Cross-dressing website asking if anyone knew someone that does make up lessons. I received several replies and after comparing the prices decided on services of AD. I sent AD an email asking if she could do my makeup and teach me. I asked her to include dressing me in some of here outfits in the price of the makeover. I receive an email back saying she would be happy to help me and provided the prices for here time. The cost for a four-hour makeup and photo shoot was two hundred pounds. I also asked if she could provide me a traveling makeup kit so I would have the right products, which were an extra fifty pounds.
I work overseas and go to the United States on vacations to visit my wife. When I am traveling, I could play dress up being Cindy. On my return from vacation, I scheduled a stop over of three days in London. I reserved the first day for my glamour shoot. The second day reserved to do my own makeup and a second photo shoot. I arranged a photographer to do another photo shoot with pictures of me out in public on the streets of London. The last day in London was reserved for the CD or TV friendly club called Sweet Wednesday.
I paid AD 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 clothing. I found a short red and black short skirt that would just cover my behind. I found a long gray skirt and white blouse that would be perfect for the secretary appearance. Continuing shopping I found a gold embroidered pullover top that would be good for an evening out. Cindy’s traveling suitcase was now stuffed with a long dress that had a red and yellow floral pattern. I selected this dress for my first day in public. As well as the dress, I found a knit cardigan, knit belt and a lovely straw hat. I ordered from the Internet a pair of brown ankle high boots. The boots looked comfortable. The next three days in London would include walking and standing; I needed to have shoes that would not hurt my feet. In my suitcase where my makeup kit, stockings, wigs, and panties, red knee-high PVC boots and fake silicone breasts. The suitcase weighted 25 kilos.
I arrived at London Heathrow Airport at 10:45 on a Monday. I had two suitcases for my traveling. I only needed my Cindy suitcase with a change of guy clothing. I found a location to store my suitcase for eight pounds a day; it was costly, but I would not be able to tote two rolling suitcases through the streets of London. With the two suitcases, I carried a backpack with my computers, cameras, phones and recharges. Clearing customs, I recover my two suitcases. I did not need both suitcases; baggage check for one suitcase would make my traveling on the Metro better. The ride on the Metro from Heathrow to Kings Cross Station took one hour. On arriving at Kings Cross Station 1 AM, I took a taxi to the Holiday Inn Express where I have paid for a room for my stay. It was now 1:30 in the afternoon with my makeup lesson schedule to start at 2:30. I called AD saying that I am running late, she said not to rush. I shaved twice once with a razor and shaving gel then with an electric razor. When finished, I was baby bottom smooth with no stubble.
The ride to AD’s house cost about twenty pounds and twenty minutes. AD met me at her door and what a good-looking woman. I did not realize that AD was a TV, but she was stunning. We struggled with my suitcase all the way to the second floor. AD had a room dedicated for makeup, with a closet full of shoes, clothing and wigs. After a few minutes to my breath, then some conservation, AD asked me to remove my clothes. I did leave on my boxers. She said to remove the boxers, and that she has seen many a Willie. I am comfortable naked with strangers, although I have gained a few extra pounds. On my chest, I have a large scar from my gallbladder surgery. This scar might appear unattractive for some people. I removed my boxers. I stood naked and ready for a makeup lesson to start. AD asked me to put on my stockings, panties and bar, which I did. I had to unpack the suitcase to find everything I needed. AD sat me in front of here make up table, provided me the traveling makeup kit. She said that she would apply makeup to half of my face. I then would do the other half. We started with the foundation; she had two in the makeup kit. One was skin color and matched my skin color and the second was white. I applied the white foundation around my eyes, and on my nose help to lighten up my eyes. The skin color foundation went on the rest of the face. The foundation was blotched with a sponge followed by a dusting of power to set the foundation. My face was the same color all over, even and smooth. The eyes were slightly lighter because of the white foundation. I was looking for not the drag queen makeup, something looking normal makeup that isn’t drawing attention to my face and made me look passable and fifteen years younger.
Next, we did the eyebrows, the eyes, and then added a blush to the cheekbones, false eyelashes, and a wig I had ordered and sent to AD home. AD directed me to look in the mirror. There was Cindy looking back at us. I was pleased with my transformation. Next, I put on the dress I have bought just for this occasion, my ankle high boots, belt and cardigan and Cindy were ready for a photo shoot. We walked down stairs entering AD backyard and a lovely garden. It was a perfect place to take some outdoor photographs. We went back to the dressing room where AD had me change into a splendid black evening gown with spaghetti straps reveling in my shoulders and chest. I had shaved my chest was so smooth. With a black lace shawl, I was ready for more photographs. The last change was into sexy black nighty lingerie with a plunging neckline showing off my cleavage.
My time was finished. I loved every minute of the afternoon. Wearing my long dress, I packed up all my Cindy things, ready to go in public. AD and I carried my suitcase downstairs where a taxi was waiting to take me back to the hotel. The taxi driver did not know the way to my hotel, arriving late at the hotel at eight pm. I arranged to meet someone from on-line at seven pm, and now I am an hour late. I set up my laptop hoping to contact my date. Cindy was ready to meet men in my hotel room. The hotel did not have free wireless. You had to pay for the Internet service at the front desk. I was dressed as Cindy. I had to go down to the lobby to buy the Internet. I had to go as Cindy. I dressed as Cindy, I had anxieties. I questioned myself if I was ready for this. Walking down the street as Cindy was easy but to talk to people would be would be a first for Cindy. I just had to talk to the desk clerk. Without Internet access, I could not contact my dates. I went to the lobby and asked for the 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 name, and he said I was in 709, give me the Internet information. I paid my ten pounds. 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 postponement 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. With him being so young, 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 were starting out to get to know each other with a couple of drinks. We chatted about our work and found out we both worked in construction. Within a few minutes before the whiskey taking effect, 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 go but was surprised 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 for breakfast. Last night passionate lovemaking and the morning rumpus smudged my makeup. Off came the makeup; on went to my guy clothes. I hurried down 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 AD 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 said he wanted Cindy dressed. The photographer arrived on time and immediately stated that I was beautiful that my outfit was perfect. He said he was leased with my appearance. It did not take long to end in bed with a few naughty pictures being taken. 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 schoolgirl. I spent another enjoyable night with an admirer. He left around midnight leaving me to sleep soundly.
The next day I reserved a room at the Central Station B&B found at the bar hosting Sweet Wednesday. Arriving around noon, I shaved smooth, and applied my makeup based on what I learned a few days before. It took me an hour to transform into Cindy. This time I dressed for the night before as Cindy the schoolgirl. I agreed to meet my next date, at the bar, at three PM. He arrived on time. We chatted a few minutes then went downstairs. This date admitted that he had never met a CD before. He said he had never been to a club-like Sweet Wednesday before, but was curious to attend. I told he could escort me around, watch the fun. If he cared to, we could go to my room for some privately. I mention to one of the other gurls I met, I had a room up stairs. A short time later, a man who asked if we could go to my room approached me. I said, “Yes.” I told my escort that I would be gone for a few minutes. My pickup and I went to my room, where Cindy was a little naughty. I went back to Sweet Wednesday where in a short time; another man approached me and asked to go to my room. I think the word was out. Cindy had a room upstairs.
Not to go into details but Cindy was much in demand. I returned to the crowd and found my escort. He said that he would like to go upstairs. My escort was a little nervous, but Cindy suggests a massage and after a few minutes, my escort did not mind if Cindy had something special. It was a happy conclusion for both of us. My escort left. I decided to change into my slutty outfit, stockings with suspenders, red panties, short red and black skirt that did not cover the top of the stockings, my eveningwear pullover top and my blond wig. I took some time and wandered around talking with some of the other CD; some dressed in sexy outfits, some dressed in casual wear.
What I like about Sweet Wednesdays is as you walk around you would be touched in a sensual way on the backside. I love the attention. I entered a room with a platform in the middle of the room. Standing at the door, I felt a hand pat my backside then rubbed between my crack. I moved my bottom in such a way to point out I did not mind the touching and fondling. My panties were removed from earlier actions, now my lily-white bottom exposed. It was natural for me to bend over for his need. My five-inch heels raised my arse as I moved from side to side showing my readiness. This position, bending over, exposing my backside was exciting. I especially enjoyed others watching my actions. When he was finished, I turned around to see who had given me the little workout. He said his name was Mike and then looked at me and said that he dressed as Michael and that a year ago we met at Sweet Wednesday. Where we made out like to Lesbos and then afterwards we spent some time in his room. The last time I was at Sweet Wednesday was over a year ago I was bending down sucking a cock and a man came up behind me. He pulled up my short skirt and pulled down my panty. I could feel him slide into me, he was thick and long. Lucky I had pre-lubed my hole so there was somewhat less painful. I was in this position for a few minutes when he came in me and when the guy I was sucking knew that, he shoots off in my mouth. I turned around to thank the man who fucked me and recognize him as Michael, the lovely man that I had met a year earlier. I told Michael I would meet him upstairs at 9 pm but he never showed.
I met a hot looking CD named Chantal, who was hot, sexy and passable. We struck up conservation where she invited me to attend her to SOHO to visit a club called Madam JoJo’s. After Sweet Wednesday closed, Chantal asked one other CD and a good-looking Spanish guy to share the taxi ride to Madam’s JoJo’s. Madam JoJo’s was a dance club where no sex allowed. Chantal told me that sometimes men would use the restroom for naughty fun with a CD. For cross-dresser, there was no cover charge. We entered the club. I stood to one side, getting a view of the club layout. There were a dance floor, chairs and benches to sit and a fully stocked bar. I was looking around the club when a drunken guy, approached me. He took my arm and motion to go to the toilet. I was surprised at how quickly someone approached me. Feeling a little naughty and horny, I allow a man to take me to one of the toilets. The drunken guy took out a condom and put it on his erection. When he did, he came. So much for being naughty. I returned meet my friends who met another CD and TV. The loud music prevented you from talking. You could only drink or dance. I danced with several guys and with two cute CD; I remained at the club until 2 AM where I was being to feel tired because of the jet lag, the late hour and the dancing. I decided to return to Central Station.
I dressed as Cindy; I exited the club walking the streets of SOHO at two in the morning alone. The street crowded with people of all types of dress, and ages. The young were mostly in bizarre outfits with flamboyant hairstyles and color. I found a taxi that returned me to the Central Station at three AM. Exhausted, I placed my head on the pillow, remembering all the attention, and I had this day and night.