Another Day at the Office

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An Escorts how to Handbook.
3.2k words
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Sean943
Sean943
118 Followers

It was hard to believe that my sailing holiday with Jim; on a 65ft charter yacht and him introducing me to paid Escort work; was three months ago. Although we had since done the odd twosome Escort together since then; five actually.

My daydreaming was interrupted by my desk phone ringing; it was the Admiral, as we had nicknamed him after he bought a yacht; similar to the one we were on in Plymouth. He was Jim's organiser for Escort work. His mannerisms and demeanor on the phone was not one of asking but a friendly assumption, this is what you wanted to do.

Jim was with a client for a week in Palma, Charles was down in Cornwall for a weekend with Stefan; polite greetings over, went straight to the point. He had an American client who wanted company when he was on a business layover in Glasgow next weekend. As I had always went with Jim on twosome Escorts; I was hesitant doing a solo. He then intervened, as though he had read my mind; said that the client had asked for me specifically.

Although deep down I was pleased being asked for; I didn't know if I wanted to be an Escort; he read my mind, again; stated how much. It was more than a month's salary where I was currently working; for a few days' work, and; added any additional service I may agree too, was on the usual 50:50 share basis. I said ok.

Good was his reply; Zoe, his personal secretary has already sent by TNT a brief on the client and some specific things I would need. Got to go I am off sailing this weekend. The phone went dead. Nice to be predictable.

As I arrived at my apartment; one of my neighbors' came out and said this parcel has arrived for you. I thanked her and took the parcel in; opened it. A brown envelope and light blue nightie and matching wrap. Without looking I knew who it was, one of the four guys I met on my first Escort job on the Hoe in Plymouth with Jim. Zoe had a hand written note lying on top; it was my size, she remembers from the last time. I never knew about that.

I just laughed at her comment, lifted it out and held it against me; looked the right size. Underneath were a short green hockey type skirt and a white tennis sweater, complete with green matching pants. I remember thinking this should be fun, last time they stripped the nightie and pants off me; not violent, just in a fun way.

I was to go to the Grand Central Hotel, adjacent to the Glasgow Central railway station. Although it was a grand old Victorian style hotel, it had been recently refurbished in its historical old Victorian style. I was to go to reception on Friday at three, request my pass key and go straight to his Executive Suite.

I arrived on time, dressed in my business attire, complete with requisite brief case and overnight case. Collected my pass key and went up to the room; I courteously knocked on the door and entered. To any onlookers this would not draw any undue attention. The room was large and opulent with anti-rooms off, all as in its hay day Victorian style; with red velour and leather upholstery.

As I walk in, Geoff; as he was to be known this time, rose up from the large couch he was sitting on; whiskey in hand. Came over to greet me; thanked me for coming at such short notice and said, only one this time. Instantly we were the best of buddies. He invited me to put my cases in the bedroom and throw off my jacket, kick off my shoes and relax; and asked what I wanted to drink.

After depositing my cases, jacket and shoes, I joined Geoff. He invited me to sit beside him on the big red leather couch, with a large whiskey waiting for me on the table. He told me he was over trying to close a big deal for his principal's, without going into details of what. It had been a hard week, his clients were going to discuss it over the weekend and give him their answer.

He was confident this was going to happened and said all he wanted to do was relax over the next few days. I said ok what do you want to do. We will have dinner at eight tonight but first I want to have some relaxing sex followed by a long warm bath. I said ok when do you want to start. He put his whiskey down on the table, took mine off me and said; now.

He then leaned over put his lips to mine and started to kiss; as our tongue's touched I could feel his hand start to rub up the inside of my leg; very seductively and controlled. As we relaxed and lay our backs against the soft warm leather, I crooked my leg to allow him to slide his hand up until he touched me. By this time I was fully aroused, Jim has shown me a few tricks on how to do this; as was he. As he caressed me; I had started to stroke the outside of his leg with the palm of my hand. As he reached my hardness I arrived at his, stroking it gently to bring his fully ready too.

I could hear and feel his breathing become deeper. He then slowly and seductively started to unbutton my shirt, one button at a time, as I did with his. He leaned down as my shirt opened and started to kiss and nibble my bare chest arriving at my nipples which he started to suck on. I could feel his teeth gently caressing them too. He was starting to get excited and aroused by this; as was I.

He reached down to undo my belt then I felt him unzipping my trousers; his hand went inside exploring me; as I also did to him. He had reached the point where he wanted more; invited me to stand up; slipped my shirt off my shoulders and let it drop; as I did his. We both stepped out of our trousers, carefully and with dignity. Both standing there; only in black bikini underwear; as we kissed and touched tongues, together we slid our hands, palms out, between our partner's skin and bikini underwear then slowly slid them off each other in unison.

As we stood there naked together touching, exchanging body warmth and sexual energy, with both our erections intertwined. Geoff moved us still embraced to our bedroom and to the big bed that had already been turned down for us; in anticipation of our impending use. Geoff as one of life's power brokers was the dominant partner.

I lay down on the bed to receive him, raising my knees and arching my back inviting him to enter; which he did ever so gently. Appling pressure to enhance entry, I could feel it ease after he had secured entry and slide further and further in; at full reach he touched my prostrate; I flinched. He withdrew slightly and retouched it gently; I could feel the rush of it as he did. Slowly he withdrew; I could feel it until it was almost withdrawn. Re-entered more smoothly this time, as I had already been eased, he kissed my prostrate inside again, I could feel the rush building. He built up a steady comfortable rhythm; we could feel each other's sexual energy rush; each time building in pressure inside both of us.

Time passed, slowly, I could feel that I couldn't contain it much longer; my breathing was becoming deeper and heaver. Geoff was getting more unsteady in his motion; he was building for the final stages of climax. I felt myself squirt pre-cum over my chest as Geoff unloaded inside me, once, twice and again. I enjoyed the feeling, Geoff withdrew and rolled over and alongside me; his breathing was one of exhaustion and satisfaction. We lay there for over an hour embracing each other in a spoon position.

Geoff got up walked naked into the adjoining bathroom; he had a nice tight butt; and started to fill the bath, he switched on the Jacuzzi feature added a bottle of something. I went into the lounge naked too, refilled both our whiskey glasses with very, large energy recovery measures of a 10 years old Arran whisky. We stepped into the foaming Jacuzzi, sat facing each other, our legs intertwined, lay back and enjoyed or whiskies.

We enjoyed the relaxation together, talking about everything and nothing as close friends do. Our drinks finished we got out and dried each other with care and attentiveness. As we finished Geoff gave me a present in an elegant box. On opening it contained some designer underwear; he said it's your size, I checked with Zoe. I looked in amazement at his comment; he said we have our sources too. Both of us re-dressed in smart casual attire to go for our evening meal; as relaxing businessmen after our meeting's or a day at the office; to any casual onlooker.

The meal, the attentive services were excellent as was the wine; as one would expect from an establishment of this caliber. Sitting there I could feel the elasticity of my gifted underwear band press on me; it gave an ongoing sexual rush. Which I think it was meant too.

Geoff's phone rang; he apologised for the interruption; said to the voice on the other end thank you, I am sure we will all work together on this project to make it a success. He looked at me and said, they agreed to our terms and we can proceed with our project based just outside Aberdeen. He then speed dialed a colleague and said; tell the boss they agreed and the signed contracts have been FedEx's; and closed off the call.

He looked over to me and said; I think we will be seeing more of each other, what do you think of Aberdeen as a place to visit. I said I have never been up there before; what's it like. You will like it trust me. He was on a high, leaned over and said quietly lets go upstairs and celebrate together. Geoff thanked the staff for an excellent meal and their service; he signed off the bill after he added a generous gratuity. We left together.

We arrived at the Suite and went inside; I could see Geoff was still on a high. He put his arm round my shoulders and said; I would like to do this tonight if you agree. I appreciate this is not what you expected; but I would be very appreciative if you agree.

What he wanted was for me to dress in the short nightie that he had had delivered to me. He said it was a fetish that his Boss liked and introduced him to it too. I went into the bedroom, changed into it, and must admit after our last meeting together in Plymouth I liked dressing up for a client. Jim and I did this on a few occasions when we did twosome assignments.

I lay on the bed as he came in with only a white towel on; sat on the bed beside me and started to fondle me; he was still on a high. His hands were everywhere fondling and stroking; they were so gentle, and it was nice and very arousing. I felt him remove the panties and the start of an oral massage, he was very good at it and I felt very aroused and excited by it. I could feel I was about to cum, as he moved aside; and did.

I could now feel oil being applied and he starts to enter me; very gently as before. After a while I could feel his rhythm get more unsteady in his motion; he was building for the final stages of climax; you get a feel for a person's way. I felt myself squirt pre-cum over my chest again just as Geoff unloaded inside me, once, twice and again. I enjoyed the feeling too, Geoff withdrew and rolled over and alongside me; again his breathing was one of exhaustion and satisfaction. We lay there embracing each other and fell asleep together.

We awoke together in the morning as the sun broke through the large Victorian windows; by this times we were both naked, I must have removed the nighty during the night as it lay on a bedside hanging chair next to me. We got up together; Geoff pulled on a white fluffy dressing gown with the hotel logo on it; and I had a chunky sweater and revealing tanga underwear in my case which I pulled on. More alluring in the morning Jim had said.

When our first coffee of the day was ready, we sat at the big coffee table in front of the couch that it all had started on. As I sat there my leg and underwear flashed invitingly at him; another one of the plays that Jim had shown me. I asked what he wanted to do today, he smiled and said, stay in our rooms and see how thing go. I told him of a fun sauna I knew if he was interested; not far. He said no; I would prefer to stay here where we can enjoy ourselves without interruptions. Geoff ordered a room served breakfast for two.

As the breakfast arrived, I discretely retired into the shower room, ran the shower loudly. Once the breakfast was served, I joined Geoff for breakfast. We sat there with bare legs touching each other under the table, talking about nothing and everything. Geoff suggested that we dress and have some girly type fun; I knew what that meant.

I retired to the bedroom and dressed in the green hockey skirt and a white tennis sweater. As the breakfast crockery was being cleared; Geoff retired into the shower room to get dressed. We both returned to the living room, me in my hockey gear and Geoff in a one piece white tennis dress. He looked good in it; not just a bought off the shelf on the spur of the moment thing.

We sat on the couch together facing each other, Geoff smiled came over, embraced me; I could feel his hand rub slowly up the back of my leg; his fingers slide under my knicker elastic, then slide round the side of my leg and touch me. Very alluring and sexually stimulation; it had the desired effect off arousal. I started to allow my hand to move up the inside of his tennis dress emulating his moves; he became very aroused too. I could feel him pull at my knickers as he slowly and gently removed them. He then moved to allow me to remove his too.

We both sat there embraced with only a one piece skirt and my skirt and top on, each exploring the other underneath them. We were both getting very aroused by this roll play; it does that. Geoff then reached up inside my top and slowly removed it over my head. He rolled his down without waiting on me assisting him. We both stood up with only short skirts on, which in the room mirror looked very alluring and sexually stimulating. We could see and feel each other's movement from our arousals. Geoff led me back to the bedroom where we repeated last night's activities. It was midday by the time we surfaced and had another shared Jacuzzi bath.

Geoff decided that some refreshing air and seeing the sites of Glasgow was called for. We didn't need any taxis or hire cars to do this. We used an open top tour bus; Geoff had never been on one before. The guide's commentary was based on the old Glasgow way of giving directions, from one pub to another; with commentary on the virtues of each establishment. This endeared Geoff wishing to visit a traditional Glasgow bar; we chose the Horseshoe bar, don't know its proper name, but that's what it is known as in Glasgow. We spent the rest of the afternoon there.

By the time we arrived back at our hotel suite, we were showing the signs of tourist fatigue, enhanced by Scottish beer. Geoff still could not get over the friendliness of those who shared our afternoon drinking with; including the traditional empty beer glass where we all added a ten pound note to; the kitty as it's called in Glasgow. When empty more money was added by each drinker; the staff getting any coins left as a gratuity, when the drinking is finished. Inevitably any drinks paid for by notes had copious amount of coins in the change.

We rested without otherwise indulging. Geoff had indicated that he liked fish meals, so I had booked a table at Roganos restaurant which was within walking distance. We had an excellent meal there, wine too; returning to our hotel suite late. Tonight was going to less adventurous; exhaustion had set in for both of us.

Sunday; we were awakened by a phone call, I recognized the voice from the hotel in Plymouth; it was Geoff's boss. He knew I would be there, greeted me by the name I used in Plymouth; reminisced about the night, ending, we will all have to do that again and asking me to put Geoff on the phone. I discreetly left the room at that point. When I heard the call was finished went back in. Geoff was standing there naked as I was; he said put that sexy underwear you have on. I started to think we were going to have fun. No; I was to drive him down to Ayrshire to check on one of his bosses investments; some 'politic' issues had developed.

We had a very pleasant drive down there; I toured a golf facility with a personal guide, had a light lunch in the club house and met up with Geoff late afternoon. His demeanor spoke volumes of what the rushed meeting was all about. All he said about it was politics, and that he needed to go to Edinburgh tomorrow and sort it. We drove back to the hotel, by the time we arrived back Geoff's demeanor had relaxed; he knew what he needed to do.

Although we had more fun that night and the next morning, he was still not as relaxed as he usually was. Never said anything about what was happening other than you will read about it in the papers and that their Lawyers were already on the case. I recognized Geoff's boss's picture in the papers. As we said our farewells Geoff handed me a thick envelope; adding see you in a few weeks.

As I drove back to my apartment I had decided, nice as it was, I would phone the Admiral letting him know this was my last Escort assignment; I felt comfortable and relaxed about this decision. As I went into my apartment, my neighbors came out and said this TNT parcel has just arrived for you. Again I thanked her and took the parcel in; opened it, a brown envelope and lingerie.

The phone rang.

Sean943
Sean943
118 Followers
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Sean943Sean943over 4 years agoAuthor
Descriptions

The story is set around the anonymity of those involved, hence the lack of descriptive detail of the individuals involved. Possibly I should have included some descriptions, trying to get a balance can be difficult.

I am glad you enjoyed the story even with these shortfalls.

Regards

wylderoswylderosover 4 years ago
Fun read!

You make this very pleasant to read about.

I would like it even more if there was a bit more physical description of both parties, including approximate ages.

I would enjoy this sort of work, at least as an experiment, although there is likely little interest in older men such as myself.

Fun to fantasize though. I do love to please, with the right person.

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