Fiction - The Job

My 'hands off' policy had served me well over the years. Naturally, like most policies of this sort, there is a little wiggle room when it comes to implementation. This meant that I could relax the policy at times that warranted such relaxation, but always at my own discretion. For example, I don't mind the occasional well-intended slap on the arse or a group photo at the end of the evening, but I draw the line at any serious groping attempts and have slapped many a face in defence of that line.

There was one time, and only one time, where I gave one guy a hand job. A group of university dorks had saved up all of their allowances and booked me for the evening. They all looked so awkward. Anyway, I gave the dweeb who made the booking a hand job in front of all of his friends, but that was a one time thing. Generally, the 'hands off' policy applied.

This leads me to my current quandary. I would not only have to break my policy, I'd have to shatter it into tiny little pieces. The cash amount on offer was significant, highly significant, adding a sizeable chunk of significance to my growing nest egg. On top of this, after showing the slightest bit of hesitation, another ten percent had been added unsolicited. It was certainly tempting.

"OK!" I finally said.

"Great." they responded.

"But only one at a time." I said.

"Agreed." they said nodding.

"And the supplies that I mentioned?" I added.

"The supplies that you mentioned will be ready and waiting for you on the night." the younger gentleman said.

"Miss, you are not the first young lady that we have booked for such an event and we can assure you that your safety will be well looked after." the older gentleman said quite seriously.

"Yes. You will have a private room to the side of the main proceedings. It will be right next to the ladies' room and you will also have an escort with you the whole time." the younger gentleman added nodding towards the young guy standing silently in the corner.

I extended my hand and shook each man's hand in turn, looking each in the eye saying "It's a deal."

"We'll see you on Saturday then Miss." the younger gentleman confirmed.

"What time would you like me here?" I asked.

"Let's say eight thirty? Give you some time to set up." the younger gentleman said.

"Eight thirty it is." I agreed.

"And you'll stay until everyone that requires your services is satisfied. Understood?" the older gentleman said, half asking, half telling.

"Understood." I replied.

"Here," he said reaching into his coat pocket, "consider this to be a down payment." he said handing me a wad of cash.

I hope that my poker face held as I placed the cash straight into my handbag before zipping it closed.

"Once you get dressed, Jimmy will show you to the door." the younger gentleman said as they both left.

That just left Jimmy and I alone. Jimmy studied me closely as I dressed in silence. Not in a leering or perverted sort of way, it felt more protective than anything else. Once I was clothed again, Jimmy extended one arm towards the door at the rear of the room and bowed his head slightly.

***

Saturday evening came around and I was getting ready to leave home for the big event. I used to get a few butterflies in my stomach before one of my regular shows, but they had faded over the years. These days, it was just like another day at the office. Tonight, those butterflies had returned, but this time they were slightly more active. I've never been paid so much for a personal show before. Bucks parties and birthdays were my normal clientèle. The pay for those was normally OK, but this was my first corporate gig and it was on another level completely. I'd never done anything like this before and the prospect simultaneously excited and terrified me.

***

Being naked in front of strangers never bothered me too much. I did my show with most of the men and one or two of the women getting to slap my arse. On top of that, a fair number even copped a feel of at least one of my tits. With the amount that I was being paid, I was more than happy to waive the 'hands off' policy for this performance. Music pumping, I pranced around and danced and gyrated for my appreciative audience before taking my final bow. Collecting my discarded items of clothing, I returned to the room that had been provided for me.

Everything was still in place as I entered. In the middle was a large table covered by a soft quilted fabric with what seemed to be a small foam mattress underneath. Just inside the door there was a smaller table with three boxes labelled small, medium and large along with two pump packs, a box of tissues and some wet wipes. There were also some extra chilled water bottles and an assortment of individually wrapped chocolates that had appeared since I had left to give my performance. All perfectly in line with expectations.

I placed my handbag and my discarded outfit on the far corner of the large table and went back to the door to collect one of the pump packs. The label said that it was lavender scented, I had a quick sniff and it did not seem to be too strong.

As I put the pump pack down, there was a soft knock at the door.

"Come in." I said.

"You were wonderful tonight Miss. Everyone enjoyed your opening performance." the younger of the two gentlemen that I had met earlier in the week said as he entered.

"Thank you sir." I replied.

"Frank, Miss, call me Frank." he said.

"OK, thank you Frank." I said nodding.

"Are you ready for your encore?" Frank asked.

"Everything looks fine in here, so I suppose I'm ready to go." I responded.

Frank walked over to the table by the door and inspected the three boxes in turn.

"What do you think Miss? Small, medium or large?" Frank asked.

"Whatever you're most comfortable with." I replied diplomatically.

"I think medium Miss." Frank said as he opened the box.

Looking to the door, Frank said, "Wait outside for this one Jimmy, I'll let you know when I'm finished.

"Yes boss." Jimmy said as he backed out of the room closing the door.

"Now, medium, wasn't it?" Frank asked rhetorically as he fiddled trying to open the package.

I took my position up on the table and pumped a few squirts onto my hand, applying it liberally as needed.

"I hate using these things, you know, but I respect our ladies too much not too." Frank said as he stepped towards me.

"Ready Miss?" Frank asked.

"Ready Frank." I replied.

Frank stepped forward and entered me in one smooth and gentle motion.

"Nice!" Frank said, "Not too loose, not too tight. You're just like goldilocks Miss, you're 'juuuuust right'"

This wasn't my first time having sex on a table in the back room of a bar with a man that I didn't know very well. It was, however, the first time that I was having sex on a table in the back room of a bar with a man that I didn't know very well who was paying me a small fortune to do so.

"Everything OK Miss?" Frank asked.

"Oh fuck that's good." was all I managed to say in response.

"Wonderful." Frank said as he picked up speed.

To be honest, Frank could have selected a small condom and it would have suited him just fine. Whilst it felt OK, it was not earth shattering. He blindly stimulated my most sensitive spot a few times, and that wasn't too bad, but I knew that tonight was not really about my satisfaction.

I was watching Frank's face as he continued to thrust in and out. It was clear that he liked watching my tits flop around in circles, but from time to time I played with my tits and rubbed my nipples just to spice things up for him. The first time that I reached down to rub my clit to help get myself off Frank frowned. He didn't say anything as he kept fucking me, he just frowned. I took the hint and just laid my arms to the side and let him continue.

I moaned for him, lifted my pelvis in time with his thrusting and squeezed my vaginal muscles from time to time to enhance his experience. Before too long, he was moaning and groaning and otherwise signifying that his orgasm was well and truly in progress.

Once he had returned to his senses, Frank looked at me and said, "Very nice Miss, very nice indeed."

He kept thrusting gently into me for a few more seconds before stepping back, removing himself as he did before yelling "Jimmy!".

Less than a second later, Jimmy opened the door and said "Yes boss."

As Frank took a few tissues from the box, used one to remove the condom and one to clean his penis, he said, "Go tell papa that he needs to try this one."

"Yes boss" Jimmy said as he exited and closed the door.

I was still on the table, half sitting, half reclining as I watched Frank pull his trousers up, "Thank you Miss. Very nice indeed."

Frank lingered briefly as he fiddled with his fly and aligned his tie, the whole time staring directly at my crotch. Men were visual animals, I knew that, they liked to look. Lots of men had stared at my pussy before, but the overwhelmingly vast majority of them did so with lust. Frank, on the other hand, seemed to have a slight hint of admiration.

"Papa should be in shortly Miss." Frank said as he turned to the side and headed for the door.

***

I'd had barely enough time to have a sip of water and pop a chocolate into my mouth when there was a stern knock at the door. I'd only just begun to say 'come in' when it opened and a young woman entered the room. She had a very attractive face, her makeup was superb: subtle, yet elegant. She had a pronounced waist and hips and wore a typical form-fittting, very short, 'little black dress'. She walked over to me and spun around with her back facing me.

"Unzip me please." she said.

"OK," I said as I started to oblige her, "but I did not know that I'd be entertaining any women this evening."

"Relax," she said as she turned to face me an let her dress drop to the ground revealing her elegant matching bra and panties, "I'm here to get Robbie ready for you."

"Robbie?" I asked.

"Yes." she responded as she stepped out of the dress before squatting down to pick it up, "But you should refer to him as either Robert, or sir."

"OK" I replied.

"Oh, sorry Miss. I'm Amanda, Robbie's personal assistant." she said offering her hand for me to shake.

"Pleased to meet you Amanda." I said as I shook her hand.

Looking me in the eye, Amanda said in a matter-of-fact tone as she removed her underpants cocking her head slightly, "You will ride him on that chair in the corner."

"OK." I replied before adding, "Um, but why are YOU undressing?"

"Robbie likes me to be naked when I go down on him." Amanda replied as she reached backwards with both arms to unclasp her bra.

"OK." I replied.

"When you see it, compliment him on the size of his cock. Be subtle, nothing too over the top." Amanda instructed as she tossed her bra to one side exposing her ample breasts.

"Right." I acknowledged.

"He likes tits, so if he wants to play with yours, let him. OK?" Amanda asked squeezing her own.

"OK." I said nodding as I replied.

"Sometimes he also likes to suck them, but only if he really likes them." Amanda continued.

"Good to know, thanks." I replied.

"If you do a good job, he may also want to take you from behind. Purely doggy, nothing anal, but he likes to do that squatting behind you on the floor. Any questions?" Amanda said.

Before I could respond the door opened and the older gentleman that interviewed me earlier in the week entered the room. Completely ignoring his naked personal assistant, he approached me and extended his hand. I offered my hand in response and he gently lifted it to his lips and kissed it softly.

"A pleasure to see you again Miss." he said.

Amanda was already busy loosening his tie and unbuttoning his shirt.

"I trust you've met Amanda, my new assistant?" Robert enquired as Amanda removed his shirt to reveal a chest covered in equal parts grey hair and surgical scars.

"Yes, she's very efficient." I replied.

"Your accent is unusual. South African?" Robert said.

"New Zealand." I replied.

"Do you like Amanda's breasts?" Robert asked abruptly changing the subject.

"Yes," I said, "they are very shapely." I answered as normally as I could considering how surreal the situation was.

As Amanda untied his belt and lowered his fly, Robert said, "But I can't seem to stop her from shaving her pussy. Amanda, show Miss your shaved pussy.

Amanda allowed Robert's trousers to fall to the ground and she turned to face me and said, "It's waxed, actually, not shaved."

"Let her feel how smooth you are down there sweetheart." Robert instructed pointing at Amanda's crotch.

I raised my eyebrows slightly looking Amanda in the eyes, however, she nodded her assent taking a few steps towards me. I reached down and touched her hairless vulva. Not seeming to be the slightest bit phased by the situation, Amanda broadened her stance so that I could trace her hairless labia all the way around.

"Smooth." I said nodding in agreement.

Whilst Amanda was letting me feel her waxed pussy lips, Robert stepped to the side and slid his trousers out of the way. Seeing this, Amanda turned to face him, squatted down and cupped his scrotum in one hand as she guided his limp penis into her mouth with the other.

"Amanda gives wonderful head." Robert said as he looked me up and down.

Moving to his side I said, "I can see that. You seem to be enjoying yourself."

"She won't let me fuck her though." Robert said as he looked down to watch Amanda's head bobbing back and forth.

"You don't pay me enough to take that monster inside me Robbie." Amanda said as she pulled back and stood.

"Oh my Robert, I'm sorry to side with Amanda, but I'm not sure that I'll be able to fit your, um, manly equipment inside me either." I added.

"Nonsense! Amanda, get Miss some more lube." Robert commanded.

"Here's your lube Miss." Amanda said as she passed me one of the pump packs.

Amanda ripped the condom wrapper open with her teeth and removed it. Squatting once more in front of her boss, she rolled the condom onto his shaft and said, "Ready when you are Miss!" as she escorted Robert to his chair.

I squirted a generous portion of lube onto my hand and applied it to Robert's latex-clad penis. I then made a point of pumping the same generous portion onto my hand in front of Robert and applying it to my inner lips and the first few centimetres inside my vagina before saying, "I hope that's enough lube."

"Not bad for an old man hey!" Robert said flopping his erect penis back and forth as I returned the bottle of lube to Amanda.

"A lot bigger than my boy Frankie's right?" Robert asked.

"Frank is your son?" I asked.

"Sure is. Not that you can tell from his microscopic sausage." Robert almost spat in disgust.

"Robbie, he's given you five grandchildren to take over the family business when it's their time." Amanda added.

"You got that right, two handsome grandsons to take over for me." Robert said still playing with his penis.

"OK Miss. Show me these skills of yours that Frankie's been raving about." Robert said pointing his penis towards me.

Taking my cue, I moved forward until I was standing within a few centimetres. I moved my feet apart and squatted down slightly as I shuffled myself into position, straddling him nicely.

Robert reached up with both hands and cupped both of my tits judging their weight. He squeezed them a few more times before briefly rubbing my nipples and then leaning back in his chair. Knowing what he wanted next, I reached down and took hold of his penis as I lifted myself slightly up and forward before lowering myself ready for penetration.

As I lowered myself, I could barely feel him enter me. Nonetheless, I let out a low satisfying moan as I took him all of the way in. As I was doing this, Amanda had taken up position behind Robert. Nodded approvingly, she mouthed a silent 'ohhh' and nodded again.

"Oh my!" I said as I started to lift myself slowly up again before descending once more.

Robert just moaned as he stared at my tits. I thrust my chest forward as I picked up speed so that he had something to look at.

Amanda held out a hand, opening and closing it a few times as if she were operating a puppet.

"Oh Robert. That feels soooo gooood!" I said breathlessly as I continued to ride him.

Robert then let out a long, low satisfying groan. At first, I though that he was just enjoying himself, getting into the mood. However, as I watched his body spasm slightly followed shortly thereafter by a growing grin of approval on Amanda's face, I realised the boss man had a hair trigger and had already shot his load inside me.

I would not be lying if I said it took longer than a minute, but I'd be stretching the truth at two. I'm honestly struggling to remember a guy, any guy, discharging his load that quickly ever before. I stopped my movement wondering exactly what I should do next. Luckily, Robert broke the silence.

"Very nice Miss!" Robert said matter-of-factly, "Very nice indeed."

I was still sitting on top of him and his penis was still inside me. I thought that I could feel it kinda starting to soften, but I wasn't really sure. Glancing up at Amanda briefly, I saw her flick her chin up sharply indicating that I should dismount.

I reached down to grab the base of Robert's penis in order to keep the condom in place as I dismounted. By the time I had extricated myself, released my grip and stood upright, Robert had gone completely limp with a small amount of semen visible at the tip of the condom.

"Ready for cleanup?" Amanda asked from beside me, snapping me back to reality. I'd not even realised that she had moved.

"Give me a minute, I've gotta catch my breath." Robert responded.

I grabbed a nearby water bottle and offered it to Robert, but he swatted it away with one had. Amanda and I stood in awkward silence for a minute or so until Robert regained his composure and simply stood up.

Amanda stepped forward holding a box of tissues and knelt down in front of her boss. Snatching three tissues from the box in quick succession before placing the box on the floor next to her. I watched as she carefully wrapped Robert's penis with the tissues and removed the condom. Repeating the action once more, she used the clean set of tissues to remove any residual fluids.

"Thanks you Miss. I enjoyed that." Robert said looking at my tits as Amanda sprang to her feet.

"You're welcome Robert, I'm glad you enjoyed it." I replied as Amanda hurriedly disposed of the tissues, grabbed Robert's shirt and held it open for him.

I wasn't exactly sure what was expected of me at this point, so I just stood back and watched Amanda as she fussed over every detail making sure that her boss was just right. Shirt, jocks, trousers, belt, tie every detail fussed over and aligned with precision.

Once he was fully dressed, Robert looked me up and down once more, nodded, said "Miss" and ignoring Amanda completely walked over to the door, opened it and left.

Still completely naked, Amanda walked over to the door and closed it. Turning, she said, "I think he liked you." as she reached for her bra.

"What? Really? Um?" was all I could say.

"Yeah, I think that he liked you." Amanda repeated as she fastened the clasp on her bra and adjusted both cups.

"But he came in under two minutes." I replied.

"So?" Amanda responded as she pulled her knickers up into place.

"So! Most guys normally last a bit longer than that." I replied as I watched Amanda sort out her dress.

"Miss, he was happy. That's it. Now zip me up please." Amanda replied as she turned her back.

I zipped up Amanda's dress as requested. She turned to face me and extended her hand. As I took it and shook it, she said, "Nice to meet you Miss.", released her grip and then left the room.