How I Became an Escort Pt. 03

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Overnight Sensation...
5.5k words
4.61
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6

Part 3 of the 3 part series

Updated 09/22/2022
Created 05/25/2014
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This is part three, you can read it as a standalone story but why not read the other two parts first. This one will still be here when you are done. Plus you might enjoy yourself.

*

It had taken me almost a year to fully make the transition. I had been able to find a place where I could entertain clients I had also set up a mobile manicure business and I had left the office.

I had taken almost all the steps into my new life bar one. I hadn't yet had an overnight booking. The option had been on my website all along but it was expensive. There were also stipulations I would only consider an overnight from a client I had seen before, and there would be more sleeping than sex. I'm not a machine, I'm a woman and I need my sleep.

It was a man named Bill who contacted me and requesting an overnight outcall appointment. He was a man in his mid fifties who sometimes travelled to my area. He had visited me once and I had also done an outcall to his hotel once. So I knew him and I knew it would be safe. Even so I hesitated at first.

Overnight meant ten hours. Bill had said he wanted us to go to a restaurant first, and then go back to his hotel room, even with the sleeping it was a long time. Could I hold his attention all that time?

I spoke with Joy. Now if you have read the other two parts you'll know who Joy is, she is my friend and the woman who helped get started in escorting. Joy had done a few overnights so she was perfect to talk to. What she did was ask me a question. Was Bill easy to talk to? I thought back to the times I had seen him. He was easy to talk to and funny. I realised I could cope with being in a room alone with him for eight hours.

I made the appointment but I had three weeks till Bill would arrive and some of the details would have to firmed up later. Bill was one of the few married men who spoke openly about being married with me. It was a loveless marriage with separate bedrooms but his wife wouldn't take kindly to him sleeping with another woman. As far as she knew he was under her thumb and only got sex on her terms. Bill would have to make sure that she thought she knew he was somewhere harmless that night.

The one choice that I took out of Bill's hands was the choice of hotel. I took a recommendation from Joy and insisted on it. This was a high end privately run hotel that didn't seem to bother who its guests were. Perhaps because the chain hotels were taking the business so they couldn't be choosy. A year later it was bought out by a multinational.

There is a perception that Escorts are easy to spot in hotels. But actually it is easier to be discreet than people think. I was never asked to leave a hotel because the staff realised I was an Escort. Nor was I ever asked for money by the staff for them to look the other way. This was all thanks to the fact that I once read a book about using magic to get ahead in business. Well either that or I was just lucky but luck doesn't have a fun explanation.

Magicians trick you into thinking you see something that you didn't. It's the same with getting past receptionists. You trick them into thinking they see something they don't. If I were meeting a client in a hotel I would go to reception and ask for him. I would be wearing a smart suit, be carrying a briefcase and have a building ID around my neck. The receptionist saw a businesswoman coming from an office for a meeting with the businessman in room whatever.

What they didn't see was that my ID was out of date and for a building that no longer existed, my briefcase contained wet wipes, condoms and poppers and what they defiantly didn't see was that under my business suit I had on sexy lingerie.

By going to reception I didn't draw attention to myself, as that is what a legitimate person does when they have a meeting. Getting the room number via a phone call and then trying to sneak up to the room with out being noticed will get you noticed.

Ironically I was once refused entry to a hotel when going to give a manicure. The hotel had an in house spa and refused to let me take my large makeup case in. The client and I retired to a nearby café who were happy to let me work there as long as we bought coffee and I got half a dozen bookings from other women who came into the café. Not a way I could drum up trade for Escorting.

But for overnight I needed to know that the hotel was not going to be too nosey. So using one that Joy had used on a few occasions made sense. Bill was fine with it as well as it was cheaper than the hotel he normally stayed in, as he wasn't actually coming to town on business this time but making the trip just to see me he was paying for the hotel himself as well. In fact thinking of what it was costing him just to spend the night with me made me realise I had to exceed his expectations.

The arrangements all went smoothly. Bill was able to book the hotel and a restaurant as well as book his train. The money, being a large amount, was transferred to me three days before. For my part I made sure that both Joy and another friend Marika knew where I would be and were expecting text messages from me at certain times. Although I thought Bill was safe I never trusted anyone fully.

The plan was that he would get to town and check into the hotel. I would meet him there then we would go to dinner. That way I'd have the opportunity to drop off my small bag of things I'd need first. After the meal we would retire to the hotel for the rest of the night. I would leave at eight the following morning.

The night before I was a little unsure but I knew that I could cope with it all. I'd had two previous sessions with Bill that had gone fine. I had also been booked for restaurant and function dates by other men and I had been the perfect companion in fact the only difference between this and a four hour dinner date was that after the two hours in the restaurant and two hours playtime there would still be six hours to go, part of that would be sleeping but I wasn't sure I could be on my a game for ten hours straight.

To make sure that I wasn't fatigued I didn't see any escorting clients that day. I did however have one visit to make to a very expensive address to give a manicure to a Lady who was very wealthy so I couldn't put her off. I capitalized the Lady, as it was her title, she was well known in society circles but very sweet and lovely.

To give you an idea of how wealthy she was when I got to the apartment building, on time, her ladies maid was waiting in the lobby to take me up to the penthouse. The maid was uniformed, a simple skirt suit with the family crest on the jacket lapels and the blouse.

Once I got to the room I was greeted by the butler, dressed in a liveried mourning suit, and asked to wait. I sat in the reception room and without any words I was handed a fresh cup of camomile tea by the maid. The first time I had been engaged by The Lady when offered a drink I'd asked for camomile tea, a note had been made and now the tea was automatic.

The Lady normally made me wait around half an hour. As I waited I took a pair of chopsticks from my case and started to practice with them. I was still doing this when The Lady silently entered the room.

"What are you doing my dear?" She asked.

I stood and gave a small curtsey.

"I shall be dining in an exclusive Chinese restaurant tonight, ma'am, I was just making sure I could still get the chopsticks to work." I replied.

"There is no right way to use those things you know, just dig in with them." She replied.

I smiled and put the chopsticks away.

"What is it you would like done today ma'am?" I asked.

"That is what I like about you Bea, straight down to business." She said.

"I'm going to the ballet tonight." She continued as she did so she gave the maid a glace.

The maid went into the next room and returned with a beautiful dark red silk dress that she carefully placed over the chair.

"Thank you Mary, I'm going to be wearing this with matching shoes, bag and hat. I want the nails to be a bit of a contrast." She said.

I thought for a few moments. Then took out three colour cards and showed them to The Lady against the dress. She chose one and I then followed the maid into the dressing room to set up.

While I worked The Lady talked. I had obviously influenced her train of thought a little as she told me about summers she had spent in Hong Kong as a child. She wasn't all that happy about the handover of the colony and expressed this quite forcefully.

When I was done The Lady retired to the reception room and I quickly packed everything away into my large black trunk. I went through to the reception room and waited quietly for a couple of seconds.

"Pay Bea, Henry." The Lady said to the Butler as she gestured with her head, before getting up and leaving the room.

As she stood I curtsied again.

I walked over to the desk and the Butler handed me a cheque for the correct amount. He then reached into his jacket and gave me a small white monogrammed envelope.

"With my Lady's regards." He said as he handed it to me.

This was my tip I thanked him and put the envelope into my handbag along with the cheque.

"Mary will show you out." He said.

I nodded and walked to the door of the suite where the maid was waiting.

I followed the maid to the elevator and we silently rode it down to the lobby.

"My Lady will require your services again in two weeks. I will of course phone you when I have the exact details." She said.

"Thank you. I look forward to hearing from you." I said.

She smiled and returned to the elevator.

When I got home I checked my tip from The Lady. It was more than four times what I had charged her for the manicure. If it weren't for the personalised thank you note that came with the cash I would have assumed it was a mistake.

I didn't have long and I had to change before I went to the hotel. When I say I had to change I didn't just mean my clothes, hair and makeup. I had to switch personas from the mild mannered manicurist to dangerous femme fatal.

I quickly showered and then put on a set of black lingerie. To this I added sheer black stockings, suspenders and a garter belt. I also pinned my hair up and put on a short black bob style wig with an asymmetric fringe. I rarely wear wigs but that night it suited my plans. I also put on a very tight fitting evening dress and a pair of Christian Louboutin shoes. I wore some dark red lipstick and just a touch of eye shadow.

Right on time there was a knock at my door. I had ordered one of London's famous black cabs to take me to the hotel. I opened the door and greeted the driver. From the slack jawed reaction I got I guessed my outfit would be turning heads, even with the addition of my plain black top coat. I gave the driver my overnight bag and locked my door before following him to the cab.

He put the bag inside and held the door for me. He got into the drivers seat and I told him the name of the hotel and he pulled away.

It was about a twenty-minute drive to the hotel. As the cab went from the suburbs into the city I let my mind wonder onto the night ahead. I told myself that it would be just like a four-hour dinner date except I'd have to go just a little further. I started to realise that the only thing I wasn't sure of was the actual sleeping. Other than that I would be fine.

When we got to the hotel I paid the driver and got out. I walked into the hotel and straight up to the desk. I told the girl behind the desk that I had an appointment with Bill and asked her to tell him that I was here.

Of course in the early evening and dressed as I was my businesswoman coming for a meeting act wouldn't wash. I'm sure that the receptionist had an idea what was really going on. She didn't bat an eyelid however, just as Joy had told me, and phoned up to his room. Once she replaced the phone she told me the number and said that I could go right up to the fourth floor.

I took the elevator up to the fourth floor and then walked down the corridor to the room and knocked on the door. Bill opened the door and let me in.

"Wow you look amazing." He said as he shut the door behind me.

"Thank you." I said.

There is a reason that I have used the non-de plume Bill on here it is because he looked a lot like William Shatner. The William Shatner I used to watch in 'TJ Hooker' rather than Captain Kirk. Basically he was slightly shorter than me, and a good deal shorter than me in my towering stilettos; slightly overweight man with curly hair in his mid to late fifties. He was dressed in a smart suit and had on a neat tie.

We chatted a little while I unpacked my bag. Bill complemented me on the hairstyle and was surprised when I told him it was a wig. Once I was done with unpacking it was time to go.

When we got to the lobby of the hotel I stood near the door as Bill asked the reception desk to call a taxi. I took out a cigarette and placed it in a long holder and lit it. This was before the smoking ban so I was allowed to smoke that said I only ever smoked for effect, like Clinton I don't inhale.

Once the taxi arrived I gestured for Bill to remove the cigarette from the holder and stub it out for me. I then took his arm and we got into the taxi. Again I got a slack jawed look from the driver as I got into the taxi. The idea was that I wanted to look dangerous and alluring and I was succeeding.

I'd like to say that the restaurant was great, but it wasn't really. It was expensive and exclusive but it didn't have any soul. The food was good so no problems there. I turned heads as we walked in and I was able to use my chopsticks with no issues at all. I was the perfect companion.

There is a knack to dinner dates like this. You start off the evening being friendly and chatty but as the meal or function goes on you have to ramp up the tension. Be alluring and dangerous, be a femme fatal and make sure that by the time you are in the taxi on the way to the hotel that the tension can be cut with a knife.

I was certainly able to ramp up the tension with Bill. By the time that the deserts arrived he was starting to stammer a bit and had trouble holding my gaze. I slipped off my left shoe and run the inside of my foot against his leg under the table, as I did he almost dropped his spoon. After Bill had paid the cheque (which in spite of his and the waiters best effort I could see was three figures) he went to the men's room. This gave me a moment to check in with Joy and Marika.

Once we were back in the hotel room, having walked past a receptionist who didn't look up from his computer, it was time for me to let all of the tension out. The first thing I was able to do was make the lighting soft and seductive. This was actually easy; the first switch I hit had the desired effect. The second thing was to ask Bill to unzip me.

Once I was able to wriggle out of the dress I had a great feeling of power as I let Bill look at me in just my black lingerie and towering stilettos.

"Are you ready for some dirty love?" I said.

"Urm." Was all he could stammer.

I took that as a yes and stood in front of him and started to push his suit jacket from his shoulders. He got my meaning and took the jacket off. I took it from him and threw it over a chair that was in the corner of the room. I then undid his tie and started on his shirt.

I'm really not sure that Bill knew exactly what was happening to him. It was very different from our last meeting, but I was in the mood for playing a role and if I just went through the motions it wouldn't have been special.

With out much effort Bill was soon naked in front of me. I moved in close and kissed him deeply. As I did I put my right arm around his shoulders while my left hand gently teased his already hard cock. I moved my lips away from his and moved my arms. Gently pushing him away so that he was sitting on the bed.

I took off my shoes and then placed my left leg on the bed as I unclipped the suspenders and gently rolled the stocking down to my knee before I removed it. I repeated this more or less with the right leg. I unclipped the garter belt and threw it over the chair where most of Bill's clothes, my dress and stockings were. Well it wasn't as if we were planning on sitting and watching TV.

I took Bill's left hand and gently got him to rise to his feet and then I dropped to my knees in front of him. I again took his length in my hand and gently started to stroke him. Again I was building the tension. I looked up took his gaze with my eyes then I let go of his cock and gently slid him into my mouth.

It was a very long and very slow blowjob. I spent a lot of time gently teasing the tip of his cock with my tongue bringing him close to the edge but not quite over the top. My knees were not up to too much kneeling so we soon ended up on the bed, where I was able to continue to use my lips and tongue to keep him at the edge.

I started to feel that he was not going to be able to take much more teasing. I shifted position so that I was laying on my side next him. Propping myself up with my right arm while my left hand was wrapped around Bill's very hot and throbbing cock.

"I want you to cum for me honey." I said.

I started to stroke just using my thumb and forefinger. Gentle long strokes at first and then I tightened my grip and quickened my pace. Bill's breathing started to become heavy.

"Just let yourself go darling." I whispered.

I wrapped my hand completely around Bill's shaft and gripped tight. As I did Bill's hips bucked off the bed and he ejaculated. Not just a little but a lot. A whole pool of warm cum sprayed over his belly and reached his chest. I kept my grip on him until he started to soften a little and then I let go.

"That was wonderful, my whole body is tingling." Bill said.

I smiled to myself and got off the bed. Before we had gone to the restaurant I had made sure that all the supplies I needed would be close at hand. I picked up a box of wipes from the nightstand.

"Just relax for a while. I'll clean you up a little." I said.

Being an escort is not all glamour. I took a couple of wipes and mopped up most of the cum from Bill. I then went into the bathroom flushed the wipes and washed my hands. It was time for a change of image so I carefully removed my wig and tied my hair more loosely for the night. I stripped from my lingerie and put on my silk robe that I'd hung on the back of the door.

I took a few moments to remove my make up and brushed my teeth. I was ready for the night. I went back into the room and Bill was sitting on the edge of the bed. He looked around at me.

"I feel all tingly I've never had an orgasm like that before." He said.

"The nights still young, lets see if we can't keep you tingling till morning." I said.

Bill stood up and slowly walked to the bathroom. Once he shut the door I was able to sort out the various clothes. I hung my dress in the wardrobe and also hung up Bill's suit. The rest of my clothes and the wig I stowed in my bag. My Christian Louboutin shoes were wrapped in cloth and put into a special box. For the journey home I had a pair of sneakers. I was also able to text Joy and Marika. I then got myself under the covers of the bed. Although still wearing my robe.

Bill came out of the bathroom and I pulled the covers on my right back so he could get into bed as well. Once he was in I gave him a long passionate kiss. I could taste the toothpaste that he used, not something that I normally encountered. I sensed that Bill needed a bit of a rest before some more fun so I let him go and sat back.

We spent around an hour chatting, which was easy. I was always worried that I might run out of things to say when doing longer sessions. But with Bill it was easy to keep the conversation going.

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