Origins of a Whore
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The Origins of a Whore
I really became a prostitute by accident. Okay, well, not really, but sort of by accident. I had been going to a chat room online and found there were quite a number of admirers of t-girls, she males, cross dressers, chicks with dicks, sluts with nuts, whatever you want to call us. I hate the term drag queen because it is so demeaning and inaccurate. I much prefer to refer to it as dressing “en femme”, and call myself a “girl with something extra”. But I digress. There were a number of guys who wrote that they were interested in meeting and some were serious and others were just playing games. One who really was interested in meeting was from England and was going to be in the city on business. I’ll call him “Brian” which is not his real name of course. I was skeptical at first until he started discussing dates and when I was available to meet him. I thought that this might actually be fun. The fact that he stated that he was going to be staying at the Renaissance Hotel helped his credibility enormously. The Renaissance is a very fancy, and expensive hotel. Since I lived downtown, I began checking out the various hotels in minute detail while dressed “en drab” as a guy. I had been fortunate enough to be setting up a large party for the company who employed me so I had been able to research a number of hotels and actually get a tour through several of them as well. This made me feel a lot more comfortable as I considered meeting a nearly complete and total stranger in a hotel room. True to his word, Brian stayed in touch and asked me to join him on a weeknight around 8:00 p.m. the following week. Over time I came to find that most businessmen arrived on a Sunday night or Monday morning and stayed in town for the week, departing on Friday. I made arrangements and prepared accordingly. Brian was polite but very matter of fact as well. He had never “been with” a girl like me before and he wasn’t sure about things. I flirted with him and was very honest about the fact that I was not interested in a love affair or serious relationship, just sex. He seemed pleased and very eager to meet, and for now, he would be interested in just oral sex. He then dropped the hint that he didn’t expect me to spend time with him for nothing and I responded by asking him what he meant, and that it was okay to be frank, as I would not be offended. He in as much asked how much it would cost him. I was a little caught off guard as I had not even expected the subject to come up. I was instantly intrigued by the idea very much and responded with an “it depends”. Then I asked if he was a cop, and he wrote back saying no, he just had heard that girls like me usually charged for our time and he thought that I probably did too. The guy was either a great actor or very sincere. I explained that it was pretty much based on time and services. After a short bit of discussion, the price of $100 was agreed upon for an hour of my time and oral sex to be performed on him. I was smart enough to add that if he thought I was exceptional and really pleased him, a tip was always appreciated. We agreed that he would e-mail me ( I had an account as a TG/CD by now) his room number so I could come to his room directly at the appointed hour and if there were any hang ups or changes in schedules he would call my cell phone. I quickly went about getting myself another cell phone just for my “girl with something extra” activities. I was nervous about the whole thing for a little while and could not believe at what I had just done. I had just contracted to have sex for payment with someone I had never met. And yet I was incredibly aroused. I could not wait to pick out an outfit and start getting ready. I knew that for the hotel I would be going to I would need something sexy, but tasteful and elegant. I simply could not go into that hotel looking like a whore, even if I was about to become one. I immediately set to work selecting an outfit. My wardrobe had started growing a lot and it would explode very soon as I became a regular call girl with routine clients and even a few repeaters and one or two regulars. I contacted a t-girl friend of mine I knew who was an e****t and who had visited me several times. We had enjoyed our girl to girl time together very much. “Missy” was surprised when I told her but agreed to help me and even coached me a little on how to act and what to do and say should anything happen at the hotel. She also let me “practice” on her, and gave me a little professional advice on how to help a guy relax, and how to not waste time or let a guy waste your time either. She was impressed that I had gotten him to agree to $100 for just a BJ. Missy told me that with my looks and my equipment I could make a lot more. We agreed to work together because she often had more work then she had time for, and she sometimes needed another girl like us for a client. Missy also helped me with my outfits.
The day arrived and I left work early to ensure I was ready in time. I usually did this on weekends when I was going to attend a Fetish ball. I’d take Friday off and not shave with a blade on Thursday, so that by Saturday night I could get a really close shave. I laid out everything and then bathed, shaved and got partially dressed. Then, I did my make up, finished dressing and did my nails. I had selected a black dress that was above the knee in length but not really a mini either. It was a black sheath chemise with a black lace overdress. It fit snugly and accentuated my curves, even if they were false ones. It was high necked, and also buttoned at the back of the neck which helped to naturally hide my Adam’s apple and make it easier to pass. Even though I knew I probably wasn’t going to be getting undressed I wore undergarments that were appropriate, thigh high stockings, and prepared for the possibility that Brian might want to do more, on the “spur of the moment”. I wore a brownish red wig with long curly hair that looked very feminine. Black patent leather D’ Orsay pumps with 4 inch heels completed the ensemble. Missy surprised me by stopping by and helping me to get ready. A few last minute touch ups to my make up and a check of my purse to make sure I had everything I might possibly need. We agreed to meet at a bar we both knew to be friendly to our sort afterwards. It was cool out and getting cooler so I slipped on my lined raincoat and headed out with a kiss for good luck from Missy. The hotel was a short walk from the apartment so there was no need to hail a cab. I left via the side entrance to my apartment building which put me on a major street. I remembered to walk carefully but purposefully. After a few moments I relaxed, feeling the cool air draft underneath my skirt, cooling me through my open raincoat. I settled into a walk, feminine, businesslike, but not hurried, just easy, and effortless, without any stress. I covered the four or five blocks in no time and prepared myself. I smiled as the doorman helped me through the revolving door and stepped carefully to the stairs. I walked up as much like a real girl would and started to cross the lobby. I had read about the call girl who had the New York Governor as a client and how she was terrified of tripping and falling in a fancy hotel in her four inch heels and I remembered feeling the same way. I also expected one of the hotel staff to point at me and scream, “TG Whore!”, but that too, failed to happen. I relaxed and reminded myself that I had just as much right as anyone else to be here, and remembered the advice I had been given on how to walk seductively. I avoided eye contact and passed by the front desk and the bar as if I knew where I was going, and of course I did. I had been there many times. I paused at the elevators and one soon arrived. I stepped in, pressed the floor button, and stepped to the back of the elevator. I watched as an older couple in their fifties or sixties entered and turned around to face the doors. The woman glanced back at me for a moment and then looked back to the front of the elevator holding her husband’s arm. He had noticed me and was being very discreet looking back slightly trying to see if he could see me out of his peripheral vision. The doors closed and the elevator moved to their floor. They stepped off and the elevator resumed its journey. It stopped, and I stepped off and followed the arrows to Brian’s room. I checked my watch and saw that I was precisely on time. It was exactly eight o’clock. Gently I knocked on the door. There was a pause for a few moments and then I heard footsteps. I could feel his eyes on me through the peephole, and I wondered if he would be pleased, or disappointed. The door opened and I held my breath. Then I saw him and our eyes met.
“Are you Brian?” I asked in my best female voice. He nodded and started to smile.
“I’m Danielle,” I said brightly with a smile. He smiled and invited me in shutting the door behind me. He was the perfect gentlemen and offered to take my coat as he led me into his room. It was quite nice, and I thanked him. His room had a beautiful view of the city too.
“You’re really tall,” he said and then blushed in embarrassment. I laughed easily in my best female laugh which I had not practiced often. He apologized and I said it was okay, and he should relax, it was just the four inch heels I was wearing. Then I turned and asked him coyly if he was disappointed in my appearance and he quickly reassured me that he thought I was beautiful. I smiled and he thanked me and offered me a drink. I thought it might help me relax, so I accepted. Besides, why not take advantage of the hotel’s honor bar I thought? Brian, or his company could afford it. I asked what he had and he gave me some brand names. I selected a good Scotch on the rocks with just a little water. I think Brian was more nervous than I was. I explained that I needed to use the phone to make a local call. He looked at me rather curiously. I smiled and explained that I had to check in, and it was merely a regular thing that was done for my protection. He nodded with an audible “Ahh” that indicated he understood and went about fixing my drink as I called Missy and let her know that I was there. She asked a few questions that she carefully worded so I could answer with yes or no answers that would give nothing away. She reminded me to have fun and said she would see me in an hour or so. I hung up and smiled as Brian offered me a glass. He allowed as how he had never done this before. I replied with a very wide eyed but a very sexy, “Me either,” and then I laughed and he relaxed and laughed too. I sipped my drink, thanked him, and suggested we get the business part of things over with so we could get on to the fun. Brian went to his wallet and started to hand me the money and I discreetly pointed to the bar.
“Put it there I whispered,” and he smiled again nervously. I reassured him that it was okay and sat down in one of the chairs near the table. I asked him to tell me a bit about himself, like where he was from in England and his work. Brian sat down and quickly relaxed. I casually reached over and picked up the money and put it in my purse and listened, smiled and laughing at his jokes. After a few minutes I set my drink down and moved over to the bed where I sat down. I suggested he move over beside me. I grabbed a few pillows to prop his head up and pushed him gently into a lying down position. Telling him to relax and just enjoy himself I undressed him. He was only slightly aroused but my mouth quickly fixed that. I moaned as I fellated him and he echoed me. I was careful to follow some of Missy’s suggestions and in no time Brian was sporting a nice erection. He wasn’t huge at all, maybe five inches in length, and not thick either, so I was able to easily take all of him into my mouth. I used my tongue a lot remembering Missy’s words, “Do what you would do if it was your dick you were sucking.” That was too easy and as I proceeded, Brian became more passionate. I only used my hand near the end when I wanted to really intensify the sensations. I was careful not to rush and really make it last as long as possible before I sped up and finished him off with a lot of tongue and licking and then some serious sucking. He groaned and warned me that he was close, and was going to come. I urged him on as I stroked his slick cock and pumped him telling him to go ahead and shoot it for me. I asked him if he wanted to watch and he nodded, saying yes, and I resumed sucking him until he came a minute or two later. I ensured he saw me swallow his load which wasn’t large and then kissed and licked him clean. I excused myself briefly and went into the bathroom to get a warm wet washcloth. I then returned and sat down with him and cleaned him up. I had been a little turned off at first as he kind of smelled funny, almost like Limburger cheese, but I had put that image aside and persevered, and very well because he immediately complimented me on my talents. I took the washcloth into the bathroom, washed my hands and quickly returned. I swallowed the last of my drink, washing down the taste of him and smiling turned to see he had dressed. He smiled broadly and I discreetly noticed that it was almost nine. Brian asked if I was available again, say tomorrow morning and I frowned and smiled saying no, I had to work. He asked what I did in my regular job, and then immediately apologized and I told him it was okay, I wasn’t offended. I told him I was a brain surgeon by day and he laughed. I asked him to excuse me just a moment and if he would be kind enough to get me my raincoat. I went to the bar for my purse and called Missy again to let her know I would be on my way in a few minutes. Then I checked my lipstick in the mirror and quickly made a few touch ups. I returned and smiled as he held my coat for me and I slipped it on. Turning to him I saw him smiling again with some bills in his hand. He handed them to me and told me I was fantastic. I smiled and told that I had enjoyed myself very much and that he should contact me the next time he was in town. I slipped them into my purse without counting them, hugged him and then left whispering him a “good night” as he shut the door. I sighed and walked to the elevator. It took a few moments to arrive and then I rode down to the lobby alone. I exited the elevator and turned left and walked to a set of stairs near the bar that entered the hotel. Stepping onto the street, the doorman asked me if I wanted a cab, and I smiled shaking my head as I began walking a short distance to the bar where I knew Missy was waiting for me. As I crossed the street a group of businessmen approached from the other direction. One smiled and said “Hello” to me and I just replied with a breathy “Good evening,” as I passed. I glanced over my shoulder, winked, and smiled as he looked back at me. It only took me about ten minutes to walk to the bar where Missy had a large glass of red wine waiting for me. I slipped off my raincoat, hugged her close, and kissed her gently on the cheek. Then I sat down, crossed my legs and opened my purse. I counted my tip and it was thirty dollars. Missy asked me to tell her everything and for the next thirty minutes or so I detailed the previous hour. Missy and I stayed for about two hours talking over wine about the evening and the type of clients she knew that required two girls on occasion. Missy also suggested that in the future I should charge more. Missy had driven so she dropped me at the apartment and I entered with no one noticing me through the alternate entrance. It was hard to say good night, but I knew we would see each other again, and very soon.
Brian returned to London and e-mailed me soon after expressing how much he had enjoyed himself and asked if he could refer me to a few friends who would also be visiting the area. I agreed, especially if they were as nice as him. It was now official. I had become a whore.
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