Harry Herricks Dream Job Pt 01

This follows on from Harry Herrick's Naked Summer and Harry Herrick and the MILFs. You don't have to read them first, but it helps.

Annabel offers me a job -- and her body

Later that night, I went to the hotel to meet Annabel. I had taken her suggestion of a job at face value, although she hadn't said a word about it in the car. As I went into the lobby, I saw my friend Sylvie in reception. We'd gone to separate schools, but were near neighbours then. She was training in Hotel Management. Strangely, we had never fucked. We liked each other well enough, but the opportunity never seemed to arise.

She sent me upstairs to the resident's lounge. Annabel was there already with a pot of coffee and some sandwiches. She waved me to a seat.

"Do you remember when we first met here?"

"Yes, you were rather drunk and propositioned me."

"And you turned me down because I was drunk."

"Yes."

"Am I sober enough for you now?"

"Yes, but..."

She waved away my protestation.

"Don't worry, I'm not going to jump you. Not yet anyway. I just wanted to make sure you understand I'm absolutely serious about what I'm going to tell you. I told you, didn't I that I was divorced in the US and came home. The settlement was, to say the least, generous. George was into all sorts of activities, some I know were pretty dubious. I persuaded him I knew more about them than I really did, so he bought me off. I had to agree to come back to England as part of the deal, but I wanted to anyway. I moved here to lie low for a while, to make sure he kept to his part of the bargain."

"The settlement made me a multi-millionaire. I've bought a nice big house near Birmingham, nothing ostentatious, and still have millions left over. I could live off what's left, but that would be boring, so I'm going to go into business. I want you to be it's first employee. I'll pay you well. I know you want to go to university somewhere, so I'm not expecting you to make a long term commitment. If you are close enough when you start, there may still be opportunities afterwards."

"Are you interested so far?"

"Intrigued, certainly."

"Good. Now before we go any further, I want you to sign this non-disclosure agreement. It says you won't talk about this to anyone else, even if you turn down the job. No signature, no job."

I read it through. It was brief and crystal clear. If I said anything about the proposal to come, the business or any of its employees, I would be liable to financial penalties based on any loss the business might incur as a result of my releasing the information.

I still didn't know what the business would be, but if it was criminal, then the agreement would be void anyway. I took a chance and signed.

"Good. Now, about the business. I'm going to be opening an escort agency. It won't be large, but it will be niche, very expensive and I hope, very profitable. The employees, male and female, will be extremely good looking, very intelligent and," she paused "very good in bed."

"Oh come on, I'm not..."

"Stop. I'm not asking you to be an escort, although you would do well. You have other skills. These people will obviously do more than go to dinner with some elderly man (or woman), give them a peck on the cheek at the end of the night and go home. Sex will be very much involved. I need them to be very skilled to justify the eye-watering fees. Assessing their skills in that area will be one of your jobs."

I sat open mouthed.

"Yes Harry, I'm offering to pay you to take some very beautiful women to bed, see how good they are at sex and teach them how to do it even better. Don't worry, I won't ask you to deal with the men. I'm going to do that myself. They don't need any particular talents anyway, besides being a good fuck. Most women my age won't be looking for Einstein when they employ an escort."

"Does that sound like something you would be interested in?" she added sarcastically.

"Ummm."

"While you are thinking about it, I'll tell you the rest. This agency will be rather different. We won't be offering teenage bimbos whose tits have a higher IQ than they do. These will be mature, intelligent women, who are also very beautiful. More like Geisha than the average escort. They will live in their own apartments in a block I also own. One of the apartments will be yours. You will be expected to keep an eye on the building as part of your contract."

"Part of your job will also be to drive them to their rendezvous with the client and at an agreed time, you will collect them and take them back to their apartment."

She went on to tell me the money I would be earning. I did a quick calculation in my head. If all went well, I would be earning at least double what I'd been getting from my previous two jobs combined. Certainly enough to make getting through a four year degree a lot less financially demanding.

"Are you interested?"

I finally got enough air in my lungs to say yes.

"One last thing. I've been going on hearsay about your abilities. I will need to assess them for myself. Do you agree?"

Did I agree? I'd been sitting with a hard on for at least an hour while she went through everything.

She didn't wait but grabbed my arm and dragged me to the lift. On the next floor up, her room was immediately opposite and within seconds we were inside. Immediately I pulled her close and kissed her. I held the kiss, running my arms across her back and down to her bum. She softened in my arms, then returned it, grabbing at my face and looking directly into my eyes.

"Make this a good one. I'm no delicate flower that needs to be handled carefully."

"I'll do my best," I said as I unfastened the zip on her dress and ran it down her back. She let the dress fall to the floor, stepping out of her shoes, then it. Her underwear was well fitting but functional, apart from a suspender belt holding up stockings, rather than tights.

"Oh, wow," I said, dropping to my knees to kiss the small patch of bare flesh at the top of each leg. In my earlier days, being allowed to touch that part had always been a turn on for me.

"Don't bother with the foreplay," she said. "I like being taken quickly."

I stood up again, by which time she had already unfastened the bra and thrown it to one side. She started to unfasten her stockings but I stopped her.

"Can you get your panties off, but keep that on? It's a huge turn on for me."

She smiled wickedly.

"Why don't you unfasten my stockings first, so I can slide the panties down."

Back on my knees again, I slowly worked my way around each leg, until the panties were free to be taken down. I was breathing hard as I slowly slid them down her legs, then slowly refastened each suspender button. All she had on now was the suspender belt and stockings. I stood back and admired her body. Her waist had perhaps thickened, her thighs might be a bit chunkier, her bum a bit fuller and her breasts might be sagging a bit more than in her youth, but in truth her body could stand against against a number of the girls I had fucked since July.

I slowly backed her across the room to the bed. She fell back, her legs opening. I pulled them apart further and over my shoulders. Her pussy was wide open, and I plunged straight into her without preamble.

"Oh that's better than the useless prick of George's. God knows how he ever got me pregnant, the useless piece of shit. Go on, don't stop, I want to know I've been fucked."

As I pounded away, she didn't stop, mixing a stream of invective against her former husband with demands to go harder, faster, deeper. I'm always turned on by women who know what they want and make sure they get it, so I had no difficulty in keeping going, harder and harder. She didn't come though so I began to slow down, if only to make sure I didn't come before her. I was still making no progress with her, so warned her I was pulling out to try something different. I had no choice though. If I kept ploughing into her like this I would come before she was anywhere near.

"Don't stop, you bastard, don't stop. Keep fucking me, don't stop."

"Don't worry, I'm not going to stop, I just want to change the angle a bit."

I piled up all the pillows on the bed, adding some cushions too, then arranged her over them, backside elevated, exposing her reddened pussy. She misunderstood my intention though.

"No, not in my ass, that's what that cocksucker George preferred."

I didn't argue just put my face to her pussy, probing with my tongue as deep as I could get, dribbling some saliva in there for added lubrication. She moaned with delight as I did so.

"That bastard always wanted me to suck his tiny dick, but he never returned the favour. Keep on doing that. Oh yes."

She was finally getting going, I could tell. Her own fluids were beginning to appear, I could taste them, and her pussy lips were becoming puffier as she became more aroused. Finally as she responded to me more and more noisily, she seemed ready and I plunged back into her, bottoming out in one single stroke. She screamed out as I did it, a triumphant "Yesss" and almost immediately began to come. Once she started, I was able to keep them rolling over her, pinching her nipples, smacking her bubble cheeks, while still pounding into her. Now that she was coming too, I could build to my own climax. I held it as long as I could but in the end had no choice but to release everything into her, gasping and grunting as I did, while she rolled though another climax of her own.

Afterwards, I didn't move, just collapsed across her back, hanging on under her arms to keep my balance and stay inside her as long as I could. Eventually though I had let go and collapsed onto the bed, leaving her to struggle free of the mountain of pillows and cushions.

"Harry, I was married for 30 years, and wasn't a virgin when I married, but I have never been fucked like that. No one has ever made me come like that. Three years without being fucked at all meant a lot of build up, but even so, that was like going through an earthquake."

"Comments like that are good for my ego. You don't need to stop."

She laughed and cuddled up to me, throwing an arm and a leg over me.

"I think I'm prepared to say you passed the test."

I could feel the cum leaking onto my thigh, but I liked lying next to a thoroughly fucked woman. I could feel the heat from her orgasms radiating into me.

"Can you stay the night?" she said wistfully.

"Not all night, but I'm sure I can manage a couple more before I have to go."

"A couple, jeez, I was expecting to have to wait until morning just for seconds."

"That's what happens when you fuck a 20 year old."

We lay cuddled together for a while before we both had to visit the bathroom. That was fun, because she didn't have an en-suite room. This was an old building and the bathroom was down the corridor. She went first, taking the only robe. Once she was back I put it on and started down the hallway. As I came back out, the lift doors opened. I ducked back inside until they passed.

Back in her room Annabel looked concerned.

"You were ages. I wondered what had happened."

"Someone came out of the lift as I came out of the bathroom. I had to wait until they passed. I didn't want anyone seeing me coming into your room.

"None of their business if they did. Now, I want those two more you promised me."

"Well I'm on the way," I said, discarding the robe.

"Indeed you are," she said. "Come here and let me help you along."

True enough, after only a few minutes of excellent oral, I was at full mast again.

"I would very much like to take that to its conclusion some time," she said, "but tonight is about me."

Our second time was much gentler. Her aggression had gone. She lay back on the bed and opened her legs. Very quickly she became wet as I attended to her with mouth and fingers. Soon she was ready and I slid gently into her. I took it easy, long, smooth strokes in, then almost all the way back out so that she gasped, thinking I was pulling out, then smoothly back. I kept changing angles, sometimes pushing hard against her clitoris, sometimes aiming to touch bottom, but never really stopping. It didn't take long for her to come this time, but once she started they kept coming, small ones at first, then every so often with a change of stroke a big one would hit.

She was crying out with each one, then wrapping her legs around me, she locked me in place as she had another one. I still hadn't come myself, so I carried on, harder and harder, until my body almost locked rigid, I pumped out what little fluid I had left in me and collapsed again. Still holding me in place with her legs, she wrapped her arms around me too and held me tight, refusing to let me pull out.

"I don't know how you do it. Second time after only about an hour or so is miraculous to an old lady like me."

I didn't admit that this had been my fourth or even fifth time today, considering my energetic farewells with Ellen. I just lay there letting her hold me. Eventually though, she had to release me and we rolled to our sides, me spooning behind her and we pulled up the covers and dozed for a while. When I woke, it was pitch black but my erection was full on and already digging into her pussy. I slowly eased up, sliding into her gradually. I wanted her to wake up and find me fully inside her. Just as I got almost fully in, she woke, then as she realised what had happened pushed back against me and I was in. We stayed like that for ages, me just stroking her body while she arched and shifted under my touch. I could tell she wasn't coming but I was. Holding on to her hip, I rolled her forwards so that she was on her face. I was fully inside her now, wrapping myself around her wonderful backside.

"I'm going to come quite quickly this time," I warned her. My weight on her back was pushing her down, so that my cock was held tightly in place. Even the smallest movement of either of us, seemed likely to set me off. I held myself as still as I could, but couldn't control it and came hard, although it was almost dry, almost painful.

"Can you move please?" she gasped. "I can hardly breathe."

I rolled off her, leaving her still gasping for air.

"You promised two more, but I didn't really think you would manage it, let alone give me such a comprehensive work out. I'm going to be really sore tomorrow but I don't care."

She paused.

"Harry, I know there is a huge difference in our ages and you will no doubt have plenty to do with vetting the girls, but can we, just occasionally do this again? I don't want to beg, but I will if I have to."

"You don't need to beg Annabel. I loved being with you, and I would love to be with you again -- and again."

Reluctantly I got dressed and left. Downstairs in the lobby, the front doors were locked and I couldn't find a way out. There was a call button on the front desk and after I pressed it, a sleepy Sylvie emerged from a back room.

"I can't get out."

"I thought you were long gone. Where've you been?"

Suddenly it dawned on her.

"Really? Annabel from the bar? Good for her. She's ancient but obviously still got it. Harry, is there anyone in this town you haven't fucked?"

"Quite a few," I said, "including you."

She sniggered. "That can be remedied," pointing to the room she had emerged from.

"Sorry Sylvie, no can do -- the well has run dry."

"Damn, she really must have been good. I thought you were the marathon man."

"Normally perhaps, but she was my second of the day."

She shook her head.

"I don't know how you do it. They just fall at your feet don't they?"

Finally she relented and let me out, still muttering about the ease of my conquests.

Next morning I was really sore. The first time with Annabel had been brutal and I was feeling the effects with back ache and sore balls.

Working for the Lotus Agency

I told mum and dad I had a new job, but was vague, obviously, about the details, just that it was a temporary post at a new business with a contract until I started University. I hinted, without actually saying it, that it was something to do with marketing.

It was a week or so before Annabel completed the purchase of her house, but a couple of days later we drove over to look at the apartments. They had been converted out of a Victorian stately home. Mine was on the ground floor, with two bedrooms, although one was fitted out as an office, with access to the security system. There was also a guest suite, linked to my apartment by a connecting door, although with its own separate entrance from the main hallway. There were four more apartments on each of the two floors above, and two in the attic spaces. All these had just one bedroom. None of the apartments, including mine, had locks accessible by the occupants, although I could remotely lock any of them if needed.

"No clients will come anywhere near here, they won't even know it exists. No visitors either. If they want company they can fuck each other -- or you for that matter -- I don't care. This building has to be a secure location."

On the way back home, we talked further about how things would be managed.

"None of the girls are virgins, obviously, and they've all been checked over by a doctor so have a clean bill of health. They will have monthly checks, you'll need to keep on top of that too"

"The first girl is Poppy. That's her working name, which is all you need to know. She moves in next week, so I want you in place before then. I'll send you a package with her details a couple of days before she arrives. I want your first assessment after a couple of days. She knows the score and what your 'duties' will be. I don't suppose I need to say this, but I will anyway. No violence, no threats. I don't want unwilling employees. They measure up or they leave. Your right of access to them, stops once they have been vetted by you. After that it is up to them."

"You'll have a small car for your own purposes. There is a flashier limo to use when you are delivering the escorts to their clients. You'll have security with you when you do that, more for show than anything else."

Within the week I had moved into my new apartment. I set up the office and tested out the impressive camera system. The day before she was due, a courier delivered the package with Poppy's details. She was 32, had a degree in French and Spanish and had never been married. She was tall, almost 5' 9" with a slim, athletic looking body. Her name seemed appropriate, with dark eyes and a mass of curly red hair.

The photos showed her in a range of outfits from business suit to evening dress, from tracksuit to bikini. Her skin was smooth and unblemished. She had been a gymnast at school and university and was obviously still fit, as the naked shots showing her toned body demonstrated. In the photos she was shaved. I generally preferred women with a nice bush of hair, but she wasn't here for my benefit.