My First Time – As a Sex Worker

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My name is Philippa, I prefer to be known as Pippa and it is also my work name; I am a Sex Worker not a prostitute. How did I become a sex worker? My boss got me into it; this is my story.

It all started after I left college and managed to get my first proper job in back office sales; effectively on a minimum wage plus a small amount. I submitted the written proposals for commercial window replacements. The salesmen obtained the enquiries, I submitted their proposals which they went on to secure or not.

After two years with this company, due to lack of candidates, I was allowed to go out on sales assignments. As a newbie I started out on the no hope sales opportunities, with time I managed to secure a few sales. My salary was slightly better, but not a lot, but I was paid a large commission on each sale; it all helped.

I had a nice rented apartment that I shared with my mother, my father disappeared years ago, never really knew him. Money was always tight, my mother worked in a supermarket on the tills and filling shelves at night; but we got by. She recently met someone working in the store, first person she went out with since my father’s disappearance trick. They got on well together and eventually she moved in with them; I could now manage financially, just, on my own. So I took over the apartment.

One day I was called into my Sales Managers office; he said this is a sales opportunity you can look after. It will be a difficult one to capture but I think you can manage it, good experience if nothing else; and I now had use of a company pool car. Only passed my driving test a few weeks before; I was over the moon.

I was twenty two, five foot nine, long blond hair, toned slim figure; I did gymnastics as a hobby. I had a few boyfriends; none of them stood the test of time. They all only wanted one thing, closes they got was their cold hands down my knickers, and even then they messed it up. I could do better myself and often did; well we all do; don’t we?

I went to see my first major client, a consulting company who was acting on behalf of a City Building Works Department. I was given the formal enquiry after I had registered interest for my company to bid for this project.

Our QS department did their estimates and a new girl Jo, who only started two days ago, did the written proposal for me. She was disabled and in a wheel chair, the proposal was uninspiring; her first job after coming out of hospital three months ago; they had to break her legs so she could sit in a wheelchair. She was very enthusiastic, so we sat down together and brought it up to a presentable information standard; best I have ever seen from the company.

Jo said leave it with me; when I was in hospital and before that when all I could do lying in bed, I learnt how to use professional proposal presentation and publishing software packages. Next day Jo gave me an absolutely fantastically presented proposal to me. It included a picture of me and detailed my professional skills. My job was now to get the Sales Manager to sign it off.

The next day I took it into him to approve, he was over the moon about it. When he looked at the value on the proposal, just over one million; that was ten times bigger than our largest contract, he almost fell out of his chair. I talked him into reducing the price to just below one million to get us into the next stage of being short listed.

Although he was unsure of letting me run with this proposal, given that I was the newbie. He asked me could I bring this contract home and do you know what it will entail; I said yes I can. The next day I hand delivered the proposal to the consultants; my life was to change for ever from that point on.

The consultants reviewed it and prepared a never ending stream of questions for me to answer. Jo and I gave well prepared and presented answers. A month later we were told we were short listed; final stage.

My Sales Manager was ecstatic at me getting this far with the proposal. Some of the salesmen were critical and said all you need to do is sleep with the client and win the order; at that time I didn’t realise the implications of what they said.

Head office had now taken an interest in this proposal and challenged my Sales Manager on, could I bring this contract home or, should they get someone else to do it and did I understand what was required of me to do it. Being cornered he said yes; look at her profile in the proposal. Answer was ok I think she can do it; my approval to proceed.

I didn’t know it at this time but my boss had just given me my first assignment as a sex worker.

I was given my final brief on how much I could negotiate on without referral back to him and head office. I was told, if asked about reseller discount, to reply it will be applied in the usual way; no more. I was surprised by this; my boss said you don’t want to know.

Arrangements were made for me to stay overnight at the casino oyna Scotsman hotel, in Edinburgh and have a signing meal with the customer. I was to meet the head of the City Building Works Department, who had been giving presentations to the Hollyrood Parliament earlier in the day. His name was Angus and I would meet him in the restaurant lounge area at seven thirty, he would know me from my picture in the proposal.

I arrived at the hotel, checked in, and reviewed my notes and documents that needed to be signed that night. I then got dressed for my meeting; the company had advanced me three hundred, against commissions I still had to be paid; it paid for a slinky little black number and the accessories to go with it; makeup too.

I went down to the restaurant lounge with its quirky coffee table and ordered a G no ice; and waited. I watched the guests move about, trying to pick out who I was to meet; usually they will do a walk-by in the area first to gain an advantage. As I was observing a voice from behind me said, are you Pippa, I turned and said yes. He said I am Angus we are due to meet tonight. He was a bit taller than me, immaculately dressed with white hair, a smart beard and incredibly well spoken. He said bring your drink and we will go to our table. As we walked over he took my arm in a gentlemanly way. It was a rather nice experience.

The waiter came over and we ordered our meal, I had already worked out what I would have so that I wouldn’t get flustered doing it. He ordered a very nice French wine that I had never heard off before. The meal arrived and we chatted about our lives, what we did and what we would still like to do. I breached the question did he want any part of the contract clarified. He said no my staff has already gone through it with a fine toothcomb and they are happy with it. I always like to see in person who is at the other end of the proposal. And I will be happy to sign the contract for you; we can do it in your room later, better not do these signings in public.

It was at this point I realised what this meeting was all about, I don’t think I was surprised about it, not shocked as possibly I should have been. We continued to chat about our lives in a more open and intimate way. Angus had lost his wife a few years ago, I told him about my disasters of boyfriends and lack off sex life. Which he found quite funny; said it reminded him of when he was my age and did similar things; which were a total disaster. Then he met his wife and settled down. He then said do you want to go upstairs and took my hand and led me up to my room.

He could see that I was unsure of what I should do next; he said give me the contract papers and I will sign them; which he did. He then said, in a matter of fact way, can I help you off with that dress, I said yes, which he did ever so lovingly and tenderly.

I was standing there in my bra, fig leaf pants, suspender belt and stockings. He looked at me in awe; no one had ever done that to me before; I felt really good and aroused by it and could feel myself start to twinge.

He then kneeled down and undid my suspender belt, one clip at a time, gently ever so gently and then removed my stockings one at a time. My nipples were rock hard by now and I could feel wetness start to form from them and down below. I remove my bra as he slid down my pants and I stepped out of them.

I stood there naked in front of him as he looked on in silence. I undid his tie and slowly unbuttoned his shirt and slipped it off his shoulders. He had a lovely tanned body; he undid his trousers and slipped them off. We both stood there naked looking at each other, he took my hand and led me over to the bed, which had already been turned down for us by the night staff.

I lay down first and he joined me, we both lay there looking at each other. Gently he moved over and kissed me; it was so sensual, and I was getting even more aroused by it, if that was possible. He then placed his warm hand on my thigh and slowly massaged it and my inner leg. I started to feel wetness; he then caressed me with the back of his fingers. He could feel my wetness forming too, he said I think it’s time we engaged with each other; I said yes and opened my legs in invitation.

He moved over me, I could feel him touching as he tried to enter, he gently touched and retouched me; gradually entering my wetness was now making it easier. Then I could feel him slowly entering me until he had fully entered. This was my first time, I was excited and enjoying it, I let out a long breath when he was fully entered. He smiled, as did I, he slowly and tenderly withdrew and re-entered. He gently started to ungulate; I was enjoying this experience, my whole body was moving in harmony with his, I would hold and squeeze as he withdrew. I could feel he was enjoying it too. I don’t know how long we kept this up; it felt like ever and I never wanted it to stop. I was starting to climax, as was Angus; canlı casino I don’t know who came first but we both enjoyed the moment. He said thank you and I said back thank you; that was my first time. I could see he was excited about being with me on this occasion.

We lay alongside each other, pulled the sheets up over us to hide our nakedness; we held each other tenderly and fell asleep together. We awoke after a short time looking at each other, I was getting aroused again, as he was, I could feel him pressing on me; without saying anything; did it all over again. By morning we had engaged with each other four times, each time better than the time before.

We both left the bed together as we had gone into it. Angus went into the shower room, it was a large walk in shower, I joined him and we showered together; then dried each other off. Angus went out to get dressed, I wrapped myself in a towel and watched him getting dressed; he enjoyed that, as I did. He then left discreetly to preserve my dignity. I took my time getting ready, as one does, and left quietly. The account was paid on my company credit card.

I went into the office later on in the morning, on presenting the signed contract, was congratulated by my boss, in front of everyone in the office. The CEO phoned me later in the morning and congratulated me on a job well done.

Did I ever meet Angus again; yes I did and he signed three more contracts for me. After he retired to his house in the South of France, I was invited to spend the week with him, where we went to see the Monaco motor racing together. He had managed to get us seats overlooking the famous hairpin bend; the noise from the cars was incredible; we could feel the vibration in our seats. I had a fantastic week out there with him, including a visit to a billionaire’s yacht. I was invited to come out and see him again, I said yes and I am still looking forward to it.

Was I asked to prepare and undertake similar sales assignments; yes five in all over the next twelve months. Did they all involve in having sex; yes they did, including one with a woman.

Karen; she was in her late fifties, I think, very expensively dressed and had white distinguishing hair, she had a very tender and caring way about her, reminded me of my mother. I had never been with a woman before, when I said this she replied don’t worry I will show you. I enjoyed her showing me and she also enjoyed showing me what to do. That was my first time with another woman; and I really enjoyed it.

I also had several less interesting sales assignments. My salary and commissions were ten times what they had been the preceding year; I also had a new company sports car to replace my aging Honda Civic pool car.

One of the sales assignments where I was to entertain a client, cancelled at the last minute. A genuine family crisis caused it; but I did get the contract signed later and I did sleep with him. As I was already booked into the Balmoral Hotel in Edinburgh, the city’s finest hotel, that Friday night and had taken an additional night using my hotel points; I decided to stay on.

I went down to the bar, with one of my sexy tight fitting outfits on, which is very plush and expensive, why not it was on expenses. I had my usual G no ice, at the bar, as though I was waiting for someone. A voice from behind, with a soft American accent, said Hi, my name is Chuck, I couldn’t help seeing that you have been let down by someone tonight. Can I buy you a drink; I don’t know why but I said yes; he ordered against his room card and said let us get a table and asked the bartender to bring over our drinks.

We found a table and sat down, our drinks arrived. We chatted about each other and why we were there that night; he had something to do with the American Embassy and a sales mission. He gave me one of his business cards, it said he was a Senior Vice President, I innocently asked is your business vice or something. He thought that was funny and explained his family had a defence electronics company in Baltimore and he was a director in it. I said sorry; don’t be; your card; you promised. I gave him my card and explained that I was a sales consultant selling replacement windows; he said I believe you; I said but that’s what I do. Ok; what do you want to do tonight now that we know each other? I said I was going to have something to eat here as it was my first time in this hotel. Ok that’s what we will do then.

Before I could say anything we headed to the restaurant, he got us a table. Before I knew it we had ordered our meal. I ordered the same wine that Angus had ordered on my first night with him. The meal arrived, it was unbelievably superb, and we both enjoyed it.

He suddenly said out of the blue, how much for tonight, I didn’t know what to say, and said for what? Sleeping with me tonight and having superb sex. I didn’t know what to say or do; but, in sales if you are asked for something outrageous, be kaçak casino positive by pricing yourself out of the market.

I remembered his key card, which he gave to the bartender when ordering drinks, was for the Scone and Crombie Suite; the best and most expensive in the hotel. I said the same price as for your room for the night. He said; ok that’s a deal; before I could say anything, he said no let’s do it for the weekend. I didn’t know what to say, although I heard myself say it, I still don’t believe I actually said it; ok it’s a deal. I had just made my first sale as a sex worker; no, I had actually been doing that for the past year. He said, pulling me out of my dream, let’s go to my suite, the meter is running.

We went up to his room, I was actually excited about it, and did not get overly aroused by it; just yet. His suite was incredibly plush and bigger than my apartment. He poured us drinks from his bar, G&T, no ice, if I remember correctly. He handed it to me and we both walked towards the bedroom with its enormous plush bed that the sheets had already been turned down on, for us.

I then said, in a matter of fact way, can you help me off with my dress. He came towards me smiling and said yes; which he did ever so tenderly. I was soon standing there in my bra, suspender belt, stockings and fig leaf pants.

I slowly unbuttoned his shirt and slipped it off his shoulders. He had a lovely body, as he undid his trousers I helped him slip them off. He then kneeled down and undid my suspender belt; one clip at a time, then removed my stockings one at a time. I remove my bra as he slid down my pants and helped me stepped out of them. We both stood there naked looking at each other, he took my hand and led me over to the bed. I felt really aroused and in control, my nipples were rock hard and I could feel wetness start to form from them and down below.

I lay down and he joined me, we both lay there together, he moved over and kissed me; it was so sensual, as our tongues touched and rubbed together. We were getting more aroused by it; I put my hand on his thigh and slowly massaged it and his inner leg. I started to stroke his hardness and to feel his wetness form. He also caressed me with the back of his fingers and could feel my wetness forming too; I said I think it’s time we engaged with each other and opened my legs in invitation.

He moved over me, I could feel him as he entered me and I let out a quite moan of contentment; he gently touched my G-spot first time, as I flinched he slowly withdrew and re-entered and retouched my G-spot; my and his wetness were now making it easier and more comfortable. We were both enjoying it as he ungulate back and forth, my body was moving in harmony with his, and I would squeeze and hold him back as he withdrew. I could feel he was enjoying it too. I don’t know long we kept this up, I was starting to climax, he held back as I came for the first time. He started over with his unhurried undulating rhythm, I could feel myself starting to cum again, as I came for the third time so did he. We both enjoyed the moment.

By this time we were both wet with exhaustion, we lay there embracing each other. I pulled up the sheets, as I liked to do, to hide our nakedness; we held each other tenderly until we fell asleep together. We awoke still embraced looking at each other we could feel each other’s arousal, without saying anything; we did it all over again. By morning we had engaged with each other five times, each time better than the time before. I don’t know how many orgasms I had that night.

We both left the bed together and went into shower room together; we had sex again against the wall with the warm water spraying over us; a magical experience. We dried each other off. As I wrapped myself in a towel, Chuck went out and phoned down our breakfast order, I brought him out a towel and watched him put it on; he enjoyed it as I did. We had our breakfast served and ate it with only out towels on. Very sensual as Chuck kept rubbing my leg with his.

I asked him how he knew that I would be available and responsive to him last night. I asked Jack the bartender where’s all the action tonight; first having to cross his palms with lots and lots of money. He pointed you out to me and I am glad he did. I learnt something new that night, always be friends with the bartender. We both got changed; me into my one piece almost see through shorts and top with my black underwear shining through. Chuck in his white shorts and loose necked shirt.

We did the tourist route through Edinburgh seeing all the sights, as the festival was on it was buzzing with activity. We even went to see the Royal Yacht; it was on his list of things to do. He was over the moon when I told him that my uncles and older cousins actually built this ship.

Exhausted we went back to his suite, but not that exhausted. Afterwards we changed for our evening meal. Saturday night and most of Sunday we stayed in bed and had wonderful sex. I drove Chuck to the airport to catch his flight to London. As he left me he gave me a very fat envelope, with cash in it, and said I will give you a call, I have your card.

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