David Enjoys his Perfect Job

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It gets even better when he massages his sister.
10.7k words
4.63
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Part 1 of the 4 part series

Updated 06/09/2023
Created 04/24/2019
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chris99999
chris99999
3,985 Followers

"Lower"

When she gave a low moan I knew I had found the right spot. I let her enjoy my finger on her clit for a few seconds, then I pushed two fingers from my other hand deep into her cunt. When I rotated them inside her she purred with pleasure.

"Rub me harder, I am going to come."

I was now frantically working her swollen clit, and I was also finger fucking her. She has a nice cunt, but it's a big one. Time to add more fingers, four took her over the edge.

"Fuck, it's a big one."

It was. Her back was now arched and she was rolling her head from side to side. When she slumped back onto the massage table I slowly removed my fingers. She now had her eyes closed. While I waited for her to recover I looked at the clock on the wall, it made me smile, three minutes from start to finish. She always comes quickly, but was this a record for her? While I was thinking about that she opened her eyes.

"That was wonderful, you have amazing fingers."

"And you have an amazing..."

She giggled before I could finish. I then left her alone to shower and dress. While I waited I thought about her, how many times was it now? It must be ten or eleven. Despite all those times, and all the things I had done to her, she was still Mrs. Henderson. I didn't mind that, she was a nice lady and she always treated me well.

She first came to the massage parlour that I work at about a year ago, and is now a regular. I would guess that she is in her mid-sixties, possibly older. She dresses well and is obviously very rich. Over time she has told me a little about herself. She was widowed eighteen months ago, which explains why she needs my services.

"David I am ready now."

I knocked before entering. Mrs. Henderson gave me a big smile before handing over an envelope. I thanked her then I leant over and gave her a little kiss on her cheek.

As usual that made her blush, then I got another giggle.

"If only I was thirty years younger."

"Then you would be twenty."

She waved her hand at me before saying, "Don't be silly," but I could tell she liked my flattery, even though it was way over the top.

When she left I placed the envelope in my locker. I didn't need to open it to know how much it contained. She always tipped me the same, and it was a generous amount. On her second visit I had mentioned it, hinting that it was too much. That got a nice smile from her, then she said, "I give my hairdresser what I give you. Both of you provide a top class service," then she looked me in the eye before adding, "And that is the end of this topic."

The shower was nice and hot with a strong flow, just how I like it. My next client was in forty five minutes so I wasn't in a hurry. It was always a pleasure to see Mrs. Henderson, but why did she never want more? It was always simple with her. I would play with her small tits for thirty seconds at the most, then she would open her legs. A few minutes with my fingers on her cunt was enough for her. With what she was tipping me she deserved to be fucked, or at least licked. However I have been working at this place long enough to know that the best course of action is to let the woman dictate what happens.

Twenty minutes in the shower was enough for me. As I was drying myself I thought back on how I had ended up working here. Two years ago I would never have imagined that this was my future. Back then, when I was twenty, I was working in a bar. One day while I was talking with a customer she asked me if I had ever done any acting, that surprised me.

"No, why?"

She pointed to the mirror behind me, "Take a look at yourself. You have the face, and from what I can see you have the body as well."

I just smiled at her, not sure if she was being serious. Then she reached into her jacket pocket and produced a card, it stated she was a Theatrical Agent. She then talked about acting, eventually persuading me to attend a workshop that was run by a friend of hers.

"Try it. After a few sessions Roger will be able to tell if you have any potential. If that is the case then I will sign you up."

I did my best, but after the fifth session Roger took me to one side.

"There is no easy way to say this. On a scale of one to ten you are a one."

I shrugged my shoulders, "That bad?"

"I was being generous when I gave you a one."

That hurt.

"It's a shame, you have the looks to be a leading man. However you might make it as a model," then he spoiled it by adding, "Or a porn star, that is if you have the equipment."

We parted on good terms despite his scathing criticism of my acting. As I was making my way home I thought about his last suggestion, it was his idea of a joke but I was now seriously considering it. And yes I did have the equipment, eight inches. I might not be able to act but I definitely knew how to fuck.

It took me a couple of days to get a screen test. I was nervous but I still managed a good hard erection, they seemed impressed and I was offered a job straight away. I smiled all the way home, I had just got my dream job.

A month later I wasn't sure about it, and at the end of two months I knew it wasn't for me. You would think it was the ideal job for a horny young man, all the cunt you would ever want. However in reality it's hard work. You have to fuck when you are not in the mood, and you have to do it for long stretches. One day I had to come three times, that was twice more that I would have liked. At the end of that day my cock was sore, so I quit and went back to bar work.

It looked as if that was going to be my life, serving drinks and listening to all those sob stories. However just after I had turned twenty one, another opportunity came my way.

"If you don't mind me asking, are you happy with your job?"

I looked at him, he was a new guy, probably just trying to be friendly.

"I am for now, but I am not sure if I will always be doing this."

I then watched as he took out a card from his wallet. If it was something to do with acting I would have to force a smile and politely say no. However when I read the card I was surprised, it wasn't what I had expected.

Hilltop Mansion - Exclusive Spa, Sauna & Massage

Private Members Club

**Women Only**

That was all that was on it, except for the telephone number and address at the bottom.

"Would you be interested in working there?"

"I might be. What do they pay their bar staff?"

He found that funny, but I didn't understand why.

Eventually he stopped, "Sorry, I shouldn't have laughed. I mean working as a masseur."

He wouldn't give me any details but he did manage to persuade me to go and see the place, he would setup an interview for me. He stayed for another half hour, but we didn't talk anymore. However as he was leaving he said.

"A few pointers for Tuesday, don't be late, and wear your best clothes. And make sure your shoes are clean, they hate dirty shoes."

On Tuesday I was apprehensive, but I decided to give it my best shot. The place was easier to find than I had expected so I arrived too early. My appointment was in fifteen minutes so I waited outside for five minutes before ringing the bell. The door was quickly opened and I was ushered into a waiting room by a tall attractive young women.

"May I call you David?"

I just nodded.

"Thank you, I am Alison. We do prefer first names here," then she quickly added "But never for the clients."

I nodded again

"David, Amy will see you shortly."

She then left me alone, returning when my appointment was due. I checked my watch, it was almost to the second. I was then taken to a small office where a middle-aged woman was seated behind a desk.

"David, please take a seat. I am Amy, I run this establishment."

She then spent the next twenty minutes telling me all about Hilltop Mansion, and what the job would entail. At the end I asked a few questions.

"Thank you for your time. We will contact you in the next few days."

On my way home I thought about all that had been said. My job was to massage wealthy clients, they had to be wealthy in order to be able to afford the membership. The fact that I hadn't any experience didn't seem to be a problem, apparently a two day in-house intensive course was all that I would need to make me competent. Amy had said that my looks had got me the job, all I needed to do now was to apply myself so that I would make a success of it.

So here I was, a year later on, and I was loving every minute of it. I had thought being a porn star was the perfect job for me, that was until I had tried it, but this definitely was. I was now a skilled masseur, and I prided myself on that part of my work, but it was the extra services that I provided that I enjoyed the most. What was it Amy had said to me during my interview?

"Rich and famous women come her. Your job is to give them what they want, whatever that is, but remember you have to be very discrete. Afterwards they like to pretend that they have only been here for a massage. Do I make myself clear?"

She certainly had. I was now making nearly twice as much money as I had done before I joined, but from only working two evenings a week. There was no way I was going to do anything stupid that would lose me my job. Life was good at the moment, and I wanted it to stay that way. Finally, at the age of twenty two, I had got my act together. I was even enrolled on a computer course for three days a week.

Five minutes and my next client would be here. I didn't have a name but I had been told she was a new member. I always found that exciting, the anticipation of what was to come. How old would she be, what would she look like, and what service would she want from me? I smiled to myself. My guess would be that she was at least fifty. Her clothes would be very classy, making the most of whatever body shape she had, and the service she wanted from me was whatever she was not getting at home.

There was a knock on the door, she was bang on time.

"Please come in."

The woman entered with her hand outstretched, ready to shake mine, but it stopped in mid-air.

"David what are you doing here?"

It was my Sister Gemma. I didn't know what to say, I just stood there with a stupid grin on my face. She was now looking me up and down as if she had never seen me before.

I shrugged my shoulder, then as calmly as I could manage I said, "I work here."

She snapped back, "I can see that, what I mean is why?"

"It's my job, I like it," then I added, "But why are you here?"

Her expression changed from annoyance to surprise, she hadn't expected me to ask that.

"Peter is away on business, so I thought I would pamper myself with a nice massage."

There was an awkward silence for a few seconds. She knew what I really did here, and I knew that she hadn't just come for a massage. She was the first to break the silence.

"So what do we do now?"

"You can go to reception and tell them that you are not feeling well. They will then reschedule you for another day, and for another masseur."

I could tell she didn't like that idea.

"Now that I am here why can't you do it? It's just a massage."

I had never considered that. Was that an option?

"Well?"

I looked at her, she now had her hands on her hips and she seemed determined to get her own way.

I nodded, what harm could there be in giving my big Sister a simple massage?

"I will go next door while you undress. When you are ready please lie face down on the table. Use the towel to cover your lower body."

"OK, but do I keep my underwear on?"

"Take your bra off, the straps will get in the way while I do your back. You can keep your knickers on if you want, but it is best if you take them off, they might get stained by the oil I will be using."

As I was leaving the room I heard her say, "They are very expensive, I will take them off."

Five minutes later when I returned, she was ready. She hadn't bothered to use the locker, instead she had draped her clothes over the chair, and her knickers were on top. I couldn't help smiling, they were so small, not much more than a thong. What would they look like on her? Thinking about that was a mistake, I felt my cock harden. I needed to be careful, she wasn't a normal client, she was my Sister.

I started on her shoulders, they were very tense. I massaged them deep and hard, and she responded with a few moans and groans, but she didn't complain so I carried on.

When I moved onto her back she gave a small sigh, I think it was out of relief that I had finished with her shoulders. This time my touch was gentler, still firm but not as strong as before. I was now doing long strokes down the full length of her back, only stopping when I reached the edge of the towel that was covering her bottom.

"That's good, you have a nice touch."

"Thanks, I am glad you like it."

"I bet the other women like it as well."

"I think so. I have a lot of regulars so I must be doing something right."

Her back was now done, it was time to work on her legs. It made a pleasant change to have a firm body on the table. Gemma was twenty five, which was a lot younger than most of the clients I see, typically they are at least forty years old.

"It's a bit hot in here."

"I can turn the heating down."

"No, I think I will be OK if I just get rid of the towel."

I stopped mid-stroke for a couple of seconds, she had taken me by surprise. Normally when the client asks for me to take it off it's not because she is hot, it's because she wants more than a massage.

When it was off I got back to work on her calves, but my eyes were now glued to her bottom. It was like the rest of her body, perfect. She has the good looks that seem to run in our family, and she has the body to go with her pretty face. If I was being over critical I would say that ideally her tits could do with being a bit bigger. They are not small, probably bigger than average, but my personal preference has always been for women with big tits. As a total package she is definitely a stunner. That, and her charming personality, enabled her to bag Peter, a very wealthy business man. I like him, and they seem to be a happy couple despite him being fifteen years older than her.

"That's nice, I like that."

Without realising it I had moved my hands to her bottom. I was so engrossed in thinking about her that my hands had gone onto autopilot, they were massaging her there as if she was just another client. I didn't stop, but it had been unintentional. I needed to be careful that I didn't go too far, after all she was my Sister.

"Harder please."

When I pushed down on her she gave an appreciative moan. Most of my clients like that, it grinds their cunt against the table. It's a way of getting their juices flowing, and it gives me an indication of how keen they are to go further.

As I continued to firmly massage her bottom she responded by moaning even more, she was obviously enjoying it. I was as well, my cock was now almost fully erect. I always wear shorts and a baggy T-shirt. The shorts have a tight waist band that holds my cock in, and the T-shirt covers the bit that sticks out. It's comfortable for me and it also covers it up.

It was now decision time. I could ease up and get this back to just being a simple massage, or I could continue like this as if she was just another client. Then I almost laughed, I don't know why I was bothering to think about it, if she wanted to take it further I knew I would be too weak to say no.

"Hillary was right, you do have amazing fingers."

"Hillary?"

"The woman who told me about this place, specifically about you. I met her at a dinner party and we got talking."

It must have been an interesting conversation.

"We don't use first names here, what's her second name?"

"Hendrix, no I think it's Hanson."

"Are you sure, none of them sound familiar?"

I got back to work on her bottom while she thought about it.

"Got it, she was Henderson."

I laughed, my Sister probably thought that it was because of how long it had taken her to drag up that name from memory, but it wasn't. I had laughed because less than two hours ago I had fingered Mrs. Henderson to a climax. However I wasn't going to tell her that, rule number one in this establishment is, 'What goes on in the room stays in the room'. I like my job, and there is no way I am going to risk losing it by talking to her about another client, even if she is my Sister.

I was now pushing even harder on her bottom, and I was also making circular movements, pushing her cheeks apart and then back together again. From the noises she was making I could tell she liked what I was doing. It might even end this way with her reaching a climax without me actually touching her cunt. That has happened before with other clients.

"I want..."

I continued working her pert bottom, waiting for her to tell me more.

"I want what you do to Hillary."

I had no idea how detailed there conversation had been, but it must have been quite graphic, because Gemma was now opening her legs.

"Tell me Hillary what EXACTLY does David do to you?"

"It's quite simple really, he puts his fingers up my cunts then he rubs my clit until I climax. Now would you like me to get you another glass of wine? "

"Please."

I was so engrossed in imagining what might have been said that I had stopped. I muttered a quick "Sorry," before moving my fingers to her opening.

When I gently pushed the tips of two fingers in she shuddered, then she wiggled her bottom as if she was trying to get them in deeper. I was in no hurry, this might be a one-off so I needed to savour it. All cunts are nice but there was added excitement for me because she was my Sister. Was it also special for her because I was her Brother?

As I pushed them in deeper she raised her bottom, that gave me a better view of her. I was surprised how hairy she was. Was that her choice or was it something that Peter preferred?

She now had two fingers deep up her cunt, they were in up to the knuckles. That was how I had started with Mrs. Henderson, but Gemma felt a lot tighter than her. As I started to finger fuck her I searched for her clit with my other hand. I had no problem finding it, it was a big one. It got even bigger when I started to rub it.

"Fuck that's good. Don't stop."

That made me smile. They nearly always say that, what makes them think that when I have my fingers on a nice cunt I am going to consider stopping? I was tempted to say the following.

"Do you mind if we take a break for a few minutes? I just want to read my text messages. Don't worry I will get back to your clit when I have finished."

I am many things, but stupid is not one of them, so I kept my mouth shut.

Two minutes later her breathing changed, she was now almost panting. I considered adding another finger but I was worried that might be too much for her. My two fingers in her cunt and the one on her clit were doing their job, so why change things?

Gradually her panting increased, at times she appeared to be struggling for breath. She must be close to a climax, it was now time to finish her off. I was now fingering her faster, and the finger that was on her clit was almost a blur.

"I am going to come. For fucks sake don't stop."

I didn't stop, instead I pressed harder on her clit, that gave her the climax she wanted. When she went rigid I stopped moving my fingers. She was now shaking her head from side to side. I kept my fingers still until she relaxed, then I removed them.

I was now standing next to her waiting for her to recover. It was two or three minutes before she moved, turning over to face me. Then she sat up.

I got a big smile from her before she said, "What happens now?"

"I will leave you to shower and get dressed. When I return you will give me a big fat tip."

chris99999
chris99999
3,985 Followers