How I Became an Escort Pt. 01

The first thing to say is that this story is called 'How I...' not 'Why I...'. The why is not a long story, I did for the adventure. At the time I had just hit 30. I had a good job in an office but there wasn't much chance of promotion. I was single and loving it, I went on dates and did have sexual relationships but nothing long term. That isn't to say that I was promiscuous, in fact more of my dates were left disappointed than those who made it to my bed. Physically I'm tall and slender but I have curvy hips and a bust to match. I also have flawless dark skin and shoulder length hair, I'm a good-looking package all round, If I do say so myself.

I had started to get into Internet dating with the aim of meeting people for fun both in and out of the bedroom. It was fun but at the same time it could be a little frustrating. I wasn't really getting my sense of adventure satisfied. Then one day I stumbled onto a website that listed escorts. At that time I didn't know that more refined, high class, escorts existed. I only knew about street prostitution but this website piqued my curiosity. I found myself looking at the listings of the women, and at their websites, finding that most of them were women a lot like me. I found myself thinking that instead of the dating sites I could do this and be paid for it.

I didn't actually need the money, my job paid me well enough that after my rent and weekly outgoings I had enough left over for luxuries and holidays. I didn't have an overactive libido either; I didn't need daily sex and rarely masturbated. I wasn't starved for attention and nor did have anything unpleasant in my childhood. I had no overriding reason for selling myself other than something deep inside of me wanted to do it. I spent around a year on and off thinking about becoming an escort at times I was sure I could at other times I was sure I couldn't. I needed to know more to find out from someone who had actually done it, someone who would answer my questions or tell me to forget all about it.

Of course in those days communication wasn't as easy as it is now. Social Networks didn't exist or if they did they only served small groups. The chief way of communicating to people on the Internet was still the message board. After a lot of thought I went looking for message boards for escorts. I had a look at a few of them most of which were full of flame wars and trolls. In fact that might have been enough to put me off the whole idea if I hadn't found a message board that was both informative and troll free. I signed up and lurked for about a month, I looked at posts and read comments that the women made about things they had done or were asked to do. I also read the warnings that were put up about some people. I was still at this point in two minds. I decided that I still needed to talk one to one with someone.

One woman who posted regularly on the message board was named Joy. Well actually she wasn't but I'm not using real names here. Joy was a little older than me but was also black. Her posts were both funny and insightful plus she seemed to be the one that people turned to for advice. I had a look at her website which was classy and although it had nude images none of them were explicit, plus in all photos her face was either hidden or blurred. Everything about it seemed to speak to my idea of what an escort should be. So I wrote her a carefully worded private message. I think I waited a good quarter of an hour between finishing the message and pressing send. I felt that I was crossing a line that I was taking a step to make fantasy a reality. I didn't know at that point that would be the first line of many that I would cross.

I think part of me hoped that Joy would tell me to get lost. If she had I probably would have quit trying to become an escort. However Joy's reply was sweet and encouraging. We spent about a week sending messages back and fourth, Joy was able to answer a lot of my questions and also asked me a lot of very thought provoking questions. Then Joy asked me if I wanted to meet her so we could chat properly. I jumped at the chance and we arranged to meet at Joy's apartment in the City.

I sort of felt like I was going to see Joy professionally, I was meeting her in the apartment that she used for clients rather than where she lived, I had a time slot and was politely told not to be early, but I was only going to have a chat and I didn't have to pay for it.

I got to the apartment a couple of minutes early and decided to walk around the block. Joy's apartment was in a nice part of town just off of a busy street but with a very private entryway. As I walked I wondered how many of her nervous clients had paced these same streets. I looked at my watch again and decided that I was on time so I went back to the door and hit the buzzer marked 'ABC Website Design'. This is what the landlord and the neighbours thought that Joy's business was, and in part it was as she designed websites for other escorts.

After a short pause the intercom crackled into life and a voice said "Hello?"

"Hi it's Belle." I replied.

"Come right in top floor."

The door buzzed I pushed it open and went inside. The building was very clean and well serviced and there was even a small elevator. However I decided to take the stairs up to the third floor. I realised that although the building had been built to be apartments no one was using it as such. The first floor was the office for a small magazine about keeping urban chickens. The second floor had a sign next to the door reading Business Solutions. I have to admit I don't know what a Business Solutions company does, and I don't think I was alone as attached to the door was a to-let sign. I got to the third floor and the sign read 'ABC Website Design' I knocked on the door.

The door opened and Joy indicated that I should enter. Once she had shut the door behind me I turned and looked at her. It was strange that although I'd never seen her face she looked exactly as I had pictured her. She was wearing a Japanese style silk robe.

"It's nice to finally meet you Belle." She said and held out her arms and gave me a big hug. This made me feel a lot more comfortable; I'm a hugger as well and always hug my friends when we meet, I felt the warmth and friendship of Joy's hug straight away and instantly felt as at ease as if I was with someone I had known for years.

"It's great to finally meet you as well." I said.

"Well come and sit down and I'll make you a cup of coffee." Joy said.

The apartment was open plan for the most part there was a small area with a couch and a coffee table, a desk with a computer on it a small galley kitchen area and two doors along the back wall. One of the doors was marked WC the other which was closed had no markings on it. I guessed that this was the room described on Joy's website as The Boudoir. At a glance this all looked like an office of a one woman website design company. The only sign that it was something else as I sat on the couch was a condom packet on the coffee table.

"Would you like coffee or tea?" Joy asked.

"Tea please." I replied.

"Milk and Sugar?" Joy asked.

"Just milk please." I said.

Joy put the kettle on and started to make the drinks. Once she was done she came and sat next to me. We chatted for about half an hour it was great to be able to talk to Joy and I felt happy and in my mind I was making the decision to move forward into become an escort. I guess that Joy was seeing that in me as she suggested that she put me onto her website as a duo partner. That way I could meet a client for the first time with Joy and feel safer than being on my own. Joy told me to think about it and give her a call later in the evening.

I left Joy's with my head spinning a little. The idea of a duo session with her was appealing and I thought that would be an ideal toe in the water. But I also didn't want to make a snap decision. I spent the afternoon thinking it over and I also went onto Joy's website and looked at the links to a review site. In the past Joy had done duo sessions with a lady named Tina. Tina had decided to retire but there were still a couple of reviews. I read through them and thought that there was nothing that I couldn't handle, in fact some of what was described was a bit of a turn on. I made my mind up to take the next step. Later in the evening I called Joy and told her that I would love to do duos with her.

I arranged with Joy to go to her place again and have some photographs taken for her website. When the day came I packed a small holdall with a couple of sets of lingerie and a little make up kit. I wasn't exactly sure what sort of photographs they would be. Joy would be taking them so that made me feel at ease. I also mentally prepared myself for being nude in some of the shots. This didn't really bother me too much as I'm happy with my body, most of the time, well maybe not happy but comfortable with it. I knew that I didn't want my face shown on the website but that wouldn't be a problem as Joy's face isn't shown so I knew that she would be able to blur it or crop the images so my face wasn't shown.

Having the photos taken was a lot of fun I got to Joys at about ten in the morning and she had everything all set up. The Boudoir was the room where she entertained clients and was set up with satin sheets and soft lighting. One thing that I hadn't noticed on my first visit was that a second door from the bathroom led into this room. Joy herself was wearing just an old pair of jeans and a loose tee shirt. We had a bit of a chat about the sort of photos that would be good and the clothes that I had with me. Joy also asked me if I would be happy posing nude, I told her that I was.

The first set of photos that she took was of me in a little black dress. It was actually a dress I had bought from an online retailer a few months before that turned out to be a little too small. It finished just above my stocking tops and could barely contain my breasts; it was so tight that I couldn't wear a bra under it. Joy directed me a little in how to pose although made it slightly harder by making me laugh as well.

I slipped out of the dress and posed for some photos topless. I started to feel a little nervous for the first time. Then Joy suggested that I lay on my back and she would shoot some photos of me removing my panties. It was this that stopped me being nervous, not that I gained some confidence from being nude on camera, but that the first time I tried it I got caught up with the hold up stockings I was wearing and for some reason both Joy and I collapsed laughing. The second time I took the stockings off first and we got the shot.

I posed nude for a few photos but all very demure. My neatly trimmed bush was just tantalisingly out of sight. After that I changed into a second set of lingerie as Joy stripped out of her tee shirt and jeans to reveal that she was wearing a very sexy red bra and panties. Using the auto timer on the camera Joy was able to take some shots of us together on the bed and kissing. Once we were done we both dressed and Joy got to work downloading the images onto her computer.

I helped Joy pick out three pictures for the website, one was with the dress on, one nude and one of us kissing. The ones of me taking my panties off would have to wait before they went on display, Joy made me a disk with the photos she had taken on and said that when I got my own website she would be happy to build it for me. I also wrote a little bio and list of do's and don'ts, the things I was happy to do and what I wasn't, and the two days of the week when I wasn't at my regular job. Joy said she would make the page up and email me a version for approval later in the evening.

The email from Joy came through and I looked at the mock up of the page. It looked very professional and had all the details correct. The photos looked good, and the blurring effect that Joy used on my face didn't look too creepy. I sent a reply saying that I liked it. A few minutes later I got another email from Joy telling me to check out her website as I was live. I went to her website on the front page was a menu tab for 'Duos' I clicked on it and there I was. I felt the odd combination of nerves and excitement knowing that the page was live.

After the page went live I had two weeks of doubts. Joy had told me that it could take a while before someone asked for a duo. So I wasn't expecting anything right away but the waiting made me feel anxious. Then one day my phone rang when I was on the bus. I looked at the caller ID and it was Joy I answered.

"Hi Joy, I'm on the bus." I said.

"Oh okay, can you call me back later?" She said.

"Sure I should be home in about half an hour." I replied.

"I'll speak to you then, but just to let you know I've had a duo request. Speak soon. Bye." Joy said and hung up.

So there I am sat on a bus in a Friday afternoon traffic jam with the knowledge in my head that someone wants to pay me for sex. I think the absurdity of the situation helped. It was all I could do to stop laughing.

I got home and called Joy back she answered after a couple of rings.

"Hi Joy, It's Belle." I said.

"Hi Belle, so are you excited?" She asked.

"I'm excited and nervous but I'm ready." I said.

"Okay, well his name is Greg he is someone I have seen before so I know he is safe. He has asked for 2 hours on Monday from three. Is that good for you?"

That meant I would have the weekend to prepare myself.

"Yes that will be fine. What time should I get to you?" I asked.

"If you get to me at half two I can give you a little pep talk and we can be ready. Is that okay?"

"That will be fine." I replied.

"Just one thing, Greg doesn't know this will be your first time, I think it's better that he doesn't know." Joy said.

"Okay, that's good. Thank you again. I'm looking forward to Monday." I said.

"I am too sweetie see you then." Joy said and hung up.

I spent the weekend preparing myself for Monday. My head was in the right place. A man was going to pay me money for sex, not just sex but a fun sexy time with my friend and me. This was something that I had decided I wanted to do on my own and I had been given plenty of opportunities to back out. I was happy with the decision I had made and was looking forward to it. I also did some practical preparation. Joy had lent me a dildo and I practiced putting on and removing a condom. I didn't want to fluff the small stuff and with my snafu during the photo shoot in mind I also practiced stripping out of my lingerie. By Monday morning I was nervous but confident.

I had a nice long hot bath and slowly, carefully, got myself together. I put on a very lacy bra and matching panties plus a pair of hold up stockings. Over all this I put on a simple black dress, this was for wearing on the journey, I carefully placed a sexy little red dress in my holdall along with a kimono style gown and a vest and comfortable panties for the journey home. I checked that my little make up kit was in my handbag and then I headed out.

I got to Joy's apartment at half past two as arranged. I pressed the buzzer and she let me in. As I climbed the stairs I realised than when I went down them later on I would have crossed a personal threshold. Since the webpage had gone live I had felt a little Neil Armstrong must have as he stood on the bottom rung of the ladder. Now I was going to take that giant leap that I had been itching to make.

I knocked on the door and Joy opened it. As soon as I got through it she gave me a big hug.

"Well you're not shaking so that is a good sign." She said.

"No I'm feeling great, really great." I said.

"Good, sit down and we'll have a quick chat." Joy said.

I sat down on the couch and Joy sat opposite me the other side of the coffee table on a chair.

"As I said I've seen Greg before so I know that he will respect limits, but if you feel uncomfortable with something just stop, okay." Joy said.

I nodded.

"It's all going to be very vanilla, just a little oral and sex. We're not going to have to put on a lesbian show or anything." Joy continued.

I gave an exaggerated look of disappointment that made Joy smile.

"I'm glad to see your sense of humour hasn't deserted you. That's good because we want it to be fun." Joy said.

"But being serious for a moment. If you start to feel sore at all don't grin and bear it. Change positions and use some lube or if you really can't go on let me take over. I won't judge you; in fact I might need you to take over for me. Okay pep talk over. Do you have anything you want to ask?" Joy said.

"No I'm fine, I just need to change." I said.

Joy took me into the boudoir and found me a spare hanger in the wardrobe for the dress I was wearing. I took this off and then quickly used the loo when I returned to the boudoir Joy was changing into a little black dress with practically see through panels in the bust. She wasn't wearing a bra and her large nipples could be glimpsed when the light hit the dress just right. I helped her zip the dress up and then got into my own red dress. Joy complemented me on this and told me to hang my robe up on the back of the door with hers.

I put my holdall in the bottom of the wardrobe and closed the door. I picked up my handbag and went back into the bathroom and touched up my makeup. I then took a few seconds to look myself in the eye, a final moment of confirmation that I was ready. I put my make up back in my handbag and then walked out into the main part of the apartment.

Joy had dimmed the lights a little and it was a lot less like and website design office suddenly.

"Put you bag over here." Joy said.

I walked over to the computer table and put my bag in the bottom drawer of the filing cabinet. I noticed that Joy's bag was already in there, she closed the drawer locked the cabinet and put the key under a coaster on the desk. She then turned to look at me.

"You look fabulous. How do you feel, nervous, excited, terrified?" She said.

"A good mix of all three." I replied.

Joy gave me a hug and then we went over to the couch and sat down. I glanced up at the clock and saw that it was only ten to.

Those ten minutes seemed to pass very slowly. Then suddenly there was a high-pitched trilling sound. Like an electronic grasshopper, I jumped a little and Joy smiled. She stood up and walked over to the intercom box on the door. She pressed a button.

"Hello?" she said.

"It's Greg." The slightly distorted voice came from the speaker.

"Come right up." Joy said.

She pressed another button and there were five long bleeps. I felt my heart start to beat a little faster and I quietly took some deep breaths to calm myself down. There was a sharp knock on the door and Joy reached for the handle and opened it.

Greg was a man in his early fifties. He had neat grey hair and was clean-shaven. He perhaps carried a little extra weight but was not overweight. He was wearing a suit and tie. He looked just like any man of his age who worked in an office. Joy closed the door and turned to Greg.

"How have you been?" She asked.

"Not too bad and you?" He replied.

"I've been good. Let me introduce you to Belle." Joy said.

I stood up and walked across the room. It was only about five steps but it seemed to take me a lot of effort. I started to realise that I was a little more nervous than I first thought.

"Hi I'm Belle." I said and held out my hand, which Greg gently took.

"Greg pleased to meet you." He said.

I smiled and he let go of my hand.

"You look even more stunning than you do in the photos." Greg said.

"Thank you." I said.

"Shall we sit down?" Joy said.

I took Greg's right arm and led him to the couch and sat next to him. Joy sat in the chair. Greg then reached into the inside pocket of his suit jacket and took out two white envelopes. One was marked with a J and the second with a B. The former he handed to Joy and the latter he gave to me. This was the agreed on fee, I followed Joy's lead and checked that it was the correct amount then resealed the envelope.