erotic encounters

I would like to share my latest cross-dressing experience. Like many cross-dressers, I dress up part-time. I am married and my wife does not know of my fetish of warning woman clothing. My dressing need stems from my enjoyment to the attention I received from admires. I am new at this cross-dressing having only 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 make up as Cindy. I have only dressed in public two times and paid a make-up artist to makeup. 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 is CD friendly place having visited twice in the past few years. I did a search of business that offer 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 with all day and evening out costing over one thousand pounds. That cost dressing services costs were expensive for my budget. As an alternative, I posted a message to a TV web site asking if anyone know someone that does makeup lessons. I received several replies and after comparing the prices decided on services of AD. I sent AD an email asking if she could not only do my makeup but to teach me and to include some photographs in various outfits. 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 can 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 had 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 reserve to go to 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 could find a short red and black short skirt that would my long legs in stockings. Need 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 stuff 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 tree days in London would include walking and standing; I needed to have shoes that would not hurt my feet. In my suitcase were my makeup kit, stockings, wigs, and panties, red knee-high PVC boots and fake silicone breasts. The suitcase weighted 25 kilo.

I arrived at London Heathrow Airport at 10:45 on a Monday. I had two suitcases for my traveling but only need my Cindy suitcase with a change of guy clothing. I found a location to store my suitcase for eight pounds a day, 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. For items not fitting in the suitcases, I carried a small backpack. 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 one AM, I took a taxi to the Holiday Inn Express where I have paid for a room for my stay. It was not 1:30 in the afternoon with my make up lesson schedule to state 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 house was 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 my suitcase all the way to the second floor. AD had a room dedicated for makeup, and closets full of shores, clothing and wigs. After a few minutes of conservations and catching my breathe, AD asked me to remove my clothes. I did leaving 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. Off went the boxers, I was here for a make up lesson and for dressing as a woman. 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 makeup table, provided me the traveling makeup kit. She said that she would apply makeup to half of my face and I would do the other half. We started with the foundation; she had two in the make up 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. Blotching the foundation was followed by a dusting of power sets the foundation. My face was the same color, even and smooth. The eyes were slightly lighter because of the white foundation. I was looking for not the drag queen makeup but looking for a normal makeup that not draws 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 and there was Cindy looking back at me. I was most please with my appearance and the transformation. Next, I put on the dress I have bought just for this occasion, my ankle high booths, belt and cardigan and Cindy was 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 my shoulders and chest. I had shaved my chest so was 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 finished, I loved ever minute of the afternoon. Dressed in my long dress packed up all my belonging, ready to go in public. AD and I carried my suitcase down stairs 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 had arranged to meet someone from on line at seven pm, and now I am an hour late. I set up my laptop hoping to make contact and having him meet Cindy in my hotel room. The hotel did not have free wireless and you had to pay for the Internet service at the front desk. Dressed as Cindy and not sure if I was ready for this. Walking down the street as Cindy was easy but to talk to people would be Cindy’s first meet. 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 907. I got a funny response, where the desk clerk said they did not have a 907 and he asked for my last name. I give him my name and he said I was in 709, give me the Internet information and 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 and he had not waited. This postponement was disappointing, I could not meet anyone as Cindy my first night in London. I had a date for Thursday, contacted him, and asked if he could meet me tonight, he said he could. He was younger, in his early twenties, I was not sure what to expect. He met me in my hotel room bringing with him a bottle of whiskey. We shoot hands and I asked him how I looked. He responded with approval. Starting our get to know each other with a couple of drinks, we chatting about our work, we both were in construction. Within a few minutes of 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 define 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 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 I notice 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 he left. The photographer would arrive at ten AM. I had time for a quick breakfast.

My makeup was on since yesterday. Last night and morning rumpus smudged my make up. I was not ready to be Cindy for breakfast. Off came the makeup; on went my guy clothes and I rushed down to the dining room to have my breakfast. Back in my room, it was now my time to do my own makeup. I tried to remember all AD said the day before, but this time Cindy did not look fifteen years younger more like five or ten. Looking at a photograph of my face taken from yesterday, I used it as a template for applying my makeup. I tried 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 and he was please with my appearance. It did not take long to end in bed with a few naughty pictures being taking. The photographer’s compliments told me how beautiful I looked, how he liked my body and Cindy was such a turn on. Each compliments made me hornier.

We spent the entire time in my hotel room, it turns out the lack of sleep, and missing a few meals, and I hit a low and did not feel well enough to go outside for pictures. My next date was to arrive at seven. Removing 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 and I slept soundly.

The next day I had 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 dressing as 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 and went down stairs. This date admitted that he never met a CD, had never been to a bar can club like Sweet Wednesday but was curious. I told him he could escort me around, watch the fun and if he cared to, we could go to my room for some privately. I mention to one of the other gurls I meet, I had a room up stairs. Not long after I was approach by a guy that asked if we could go to my room. I said sure, told my escort that I will 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 shot time another man approached me and asked to go to my room. I think the word was out.

Not to go into details but Cindy was much in demand. I met my escort where he suggests 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 and 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 evening wear pullover top and my blond wig. I took some time and wondered around talking with some of the other CD; some dressed in sexy outfits, some dressed in casual wear.

I like about Sweet Wednesdays is as you walk around you will touched in a sensual way on the backside. I love the attention. I was standing in one of the rooms that had a platform bed in the middle, I felt hand pat then rub my behind. I moved my bottom in such a way to point out I did not mind the touching and fondling. My panties 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 ass 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. After he finished I turned around to see who gave a 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. I the last time I was at Sweet Wednesday was over a year ago and here was a guy attracted to slutty Cindy both times.

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 was over Chantal asked one other CD and a good-looking Spanish guy to share the taxi ride to Madam’s JoJos. Madam JoJo’s was a dance club where no sexual activities allowed. I was told that sometimes the rest room was used for naughty fun. Being cross dresser there was not a cover charge. We entered the club as I stood off to the side getting a once over of the club’s layout. There was a dance floor, chairs and benches to sit and a fully stocked bar. While I was looking around a drunk guy approached me and took my arm and motion to go to the rest room, I was surprise that I was quickly chosen. Feeling a little naughty and horny, I allow myself to be taken 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 had met other CD and TV. The music was loud so you could not talk only drink and 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.

So dressed as Cindy and alone I exited the club walking the streets of SOHO at two in the morning. 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 who 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.

September 2018
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