Jill's Story - Sex, Sex & More sex Pt. 10

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Jill and James's sex life and her brother joins in.
19.5k words
4.95
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Part 10 of the 12 part series

Updated 12/23/2023
Created 08/07/2022
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JILL'S STORY - sex, sex and more sex. Pt. 10

This is a "spin off" story from "A FAMILY THAT PLAYS TOGETHER STAYS TOGETHER -- or so they say" - of which I am the original author - which is about a family that discovers sex with each other or others outside the family.

This is a story about Jill, the daughter, and her sex life with the family and her boyfriend James, and what he gets up to, plus any cock that she meets on the way

It can be read as a stand-alone story or have a look at "A FAMILY THAT PLAYS TOGETHER STAYS TOGETHER - or so they say" to connect the two.

That and this story features incest so be warned.

Part of this story also features gay / bi sex.

"A FAMILY THAT PLAYS TOGETHER STAYS TOGETHER -- or so they say" is an Incest / Taboo story, "JILL'S STORY" is a fetish story and contains fetish themes.

Please note that I am the original author of "A FAMILY THAT PLAYS TOGETHER STAYS TOGETHER" and the original author of "JILL'S STORY."

Enjoy.

JAMES

I don't think that I'd ever worked so hard, not even in the Royal Navy; I was worried that I might wear my cock away with all the fucking. I was working with Noel helping with his gardening business and providing cock for the bored housewives, I was working at The Clinic, I seemed to be popular there and was getting more and more work there plus I was helping out my flatmate Tom with his building business, I just provided a bit of muscle when he needed it, what with all this work I barely had time to get a back, crack and sack wax!!

As the winter approached there was less and less gardening work and hence less fucking of the housewives, the excuse for us being there was the gardening after all, they seemed paranoid about getting found out, it would have been much easier if we just turned up and fucked, sod the gardening. I suppose that they'd have to explain to their city type husband why the gardening bills were so high even during the winter. Noel wasn't bothered as he made enough money during the season to have a few months away in the sun during our winter.

Tom gave me as much work as I wanted, of course that work was only during the day whereas The Clinic work was evenings and weekends so it all fitted in perfectly.

It did make it a little difficult to spend time with Jill but we usually managed a few hours late afternoon, if she started in the office early it meant she got home early, before I was picked up to go to work at The Clinic if I was working there. Weekends would either be working at the clinic during the day or the evening so I could pick and choose. Tom was flexible when it came to me working for him; well he had to be if he wanted to suck my cock again. (See JILL'S STORY -Sex, Sex and More Sex. Pt. 9)

The whole atmosphere in the flat had changed, more relaxed since I'd sucked his cock and he'd sucked mine and we'd both been fucked up the arse by Jill and her strap on, we all joked about it, I'd come up behind him and squeeze his arse cheeks and whisper in his ear, "Nice arse," and he'd turn around, grab hold of my cock, made easier by the fact that we'd walk around the flat naked most of the time, and say, "Little cock."

Nothing like the sucking and fucking had happened since; I'm sure that it would happen again and Tom, Jill and I wanted it to happen again but the time and the opportunity hadn't presented its self so it was a case of wait and see.

Jill was good for me and kept me on the straight and narrow, I had gone off the rails a few times since leaving the Royal Navy before meeting Jill, don't get me wrong, we still had some fun times just more sensible fun times. She even looked after my bank accounts and earnings, she set up a set of books and she made sure that I paid tax and National Insurance on my earnings, apparently I was a male masseur in the eyes of HMRC, if it had been left to me the money would have gone straight into my pocket as part of the black economy which is all very well until you get caught. She even paid money into my account as she said as she almost lived at the flat full time she should pay part of the rent, Jill was a one off and she had no problem with me fucking for a living as long as my cock was always available when she wanted it and she was allowed to fuck around as well, it was a win win relationship for both of us.

A few evenings later I was showered and ready to head out for an evenings work at The Clinic, I was just waiting for the car to pick me up, when Tom came in, he'd been to the gym straight from work and looked hot, sweaty and pumped.

"Off to sell your cock again," he laughed.

"Got to be done, it's going to be a long hard evening apparently so don't wait up. Jill's working late as well so she will probably stay at her Mum and Dads so you'll have the flat to yourself," I replied. Neither Jill or I had any problem with just her and Tom in the flat together, Tom was too much of a gentleman to try anything unless Jill wanted his cock and then she'd give him the hint by showing him her fanny, she wasn't subtle. In fact last time I'd come back from work I'd caught them both playing Scrabble, it was getting quite competitive, so much for me thinking that they'd be fucking.

"Right then mate, going to the gym and order a take away, hope you can get it up for the clients tonight," Tom said.

I grabbed my bulge through my sweatpants and said, "Never had any problem with that mate as you well know."

I saw the look on Toms face, he wanted my cock. The intercom buzzed, my car was here.

I knew the routine when I got to The Clinic and headed straight to the showers, Simon was already there, I recognised the brand on his arsecheeks before he turned around, and was just finishing douching, part of the deal was that our arsehole had to be clean just in case the clients wanted to use fingers, dildos or butt plugs on them.

"Hey there Simon, am I working with you tonight?" I asked.

Simon turned around and said, "Not sure mate, I know I'm pulling a late one so I'm staying here tonight, you'll have to wait and see."

"Fuck me Si, your balls are huge," I said looking at his balls that were hanging between his legs.

Simon laughed, "I had them infused earlier on and I think that the Doctor wanted to see how big he could get them, the procedure was being streamed live to clients in Germany so they were calling the shots. How's your balls?"

When "on duty" I was expected to wear the clinch ring around my balls, it made then hang lower and stand out and the clients liked my nuts swinging and banging against their arsehole or fanny. When I first started wearing the ring it had made my balls ache but I'd built up the length of time I'd kept it on and now could wear it all day, forgetting it was clinched around my nuts which caused a few strange looks from the other men in the showers at the gym.

"Used to it now, maybe I'll try having my balls pumped up like yours next," I laughed and quickly said, "That's not going to happen,"

I stripped off and walked into the shower, Simon handed me the douche nozzle and said, "All yours mate, knock yourself out," and he sat down on the shower room bench and dried himself off.

I stood under the shower for a minute or so and then adjusted the flow and temperature of the douche nozzle, lubed it up before pushing it into my arse, I was used to it now and knew how to relax my ringpiece. If, a few weeks ago, you'd told me I would be filling my arse up with water and doing it in front of another man I would have said no way but now it seemed almost routine. I grunted as the pressure on my prostate gland increased and my cock hardened, I pulled the plug out and flushed the water out, repeated it a few times and walked out of the shower to dry myself off.

Two other men that I hadn't met before came into the shower room and started to strip off. One was an older man, mid fifties and the other was much younger, just a lad, maybe just twenty. Simon obviously knew them both and stood there naked and introduced them to me.

"James this is Derek," and nodded towards the older man, "and this is his son Sam and of course this is James," said Simon. We were all naked and I awkwardly shook hands with them.

They checked me out and I checked them out, Derek, the Father, was shorter than me, dark haired and muscled through work and with what I'd call a builders tan, hairy and a few tattoos that he'd obviously got when he was younger. His cock hung down over a big pair of balls, a thick uncut cock that looked like it would be a decent size when hard. His cock, balls and pubic hair had been waxed leaving a sharp line where his chest hair started. Sam, his son, was the same height as his father, his hair was long on top and shaved down the sides, but a completely different build, thin with good muscle definition, hairless, an uncut cock that even soft must have been seven inches long just hanging over his hairless balls that, like me, had a clinch ring around them pulling them down between his legs but the head of his cock was still lower than his nuts.

Simon said, "We'll leave you two to it, see you in the lounge."

I pulled on a pair of shorts and as Simon and I went into the lounge next to the shower room I heard Derek say, "OK son bend over, spread your arsecheeks and lets get the nozzle up your arse and get you washed out."

Sam replied, "Fuck, I hate this bit."

Fifteen minutes later we were all in the lounge waiting to see what we were going to be up to later that evening, it looked like we were waiting in a Doctors waiting room for an appointment, I suppose we were.

It turned out that Derek was a builder, he knew Tom my flatmate and had worked with him, it was a small world.

"I know one of the nurses that works here so got some building work here, the kind of building work that you probably wouldn't ask most builders to do. One day the Doc asked me if I'd be willing to provide some extra services, they were after some older cock, I jumped at the chance, my wife had left me a few years ago and I wasn't getting any fanny so it suited me. When Sam finished college he needed to earn some cash and the Docs wanted some younger cock so I brought him along, he spent most of his time in his bedroom wanking anyway so he was the obvious choice. Its worked out well, we can provide the genuine Father and son experience and the women love mothering him, don't they son?" explained Derek.

"Certainly do Dad," laughed Sam.

The door opened and Doctor Mac, the female one, and Nurse Sally walked in. Doctor Mac was dressed in her Doctors whites and Nurse Sally was squeezed into a nurses uniform, the type you see in the lingerie catalogues, her tits were almost popping out, her skirt hardly covered her arse and she wasn't wearing any knickers.

"Hello Aunty Sally, you're looking hot," said Sam.

"Hello Sally, you could at least have worn some panties as your knew your nephew is here," laughed Derek.

Nurse Sally just smiled and said, "Well you've never complained before about me not wearing knickers and Sam, don't call me Aunty, it makes me feel old."

So Nurse Sally was Derek's sister and Sam's Aunt and I got the impression that Nurse Sally had already had their cocks in her holes and that she was the one that got them their jobs at The Clinic.

Doctor Mac coughed, "enough of the family reunions, we better get started, I don't want to run late this evening. Simon, when you've finished here you've got an hours rest and then my husband and I will be giving you a full medical, it will be streamed to our overseas clients and I warn you now it will be a hard medical but I'll give you a shot of painkillers and a relaxant before we start, oh and I've got a new nurse to help us out but be warned she's a nasty bitch but you'll be OK with that wont you?" she asked.

Simon had a big grin on his face and said, "Of course Doctor, you know me, anything for you and for the money."

The Doctor smiled and said, "I do and that's why we've got some new equipment to use on you later. Derek and Sam, I might have another session for you after this one as well, not sure yet as they're flying in from the Channel Islands so it depends on the flights. They're both high profile influencers, both in their mid twenties, my husband carried out a couple of medical procedures on her to stretch her fanny and arsehole and recommended that she tried more cocks to keep her open, at they're influencers with a huge following they can't just go out and pick up a length of cock or hire a male escort and they know how discreet The Clinic is so have asked us to organise a session for them, at the moment she's using big dildos but wants the real thing so I thought an older cock and younger cock would be a start. Her husband will watch and might join in and he's strictly straight. I haven't forgotten you James, I've got a hard weekend booked for you so you've got a few days off to fill those balls up."

My cock stirred just at the thought.

"Back to tonight's session," Doctor Moss said, "Two older ladies, husbands are well known as are they, the husbands spend most of their time away on business so while they're away their wives like to play. All their holes are available for use, they want a hard fucking from a selection of cocks, from old cock to young cock."

"Hey, I'm not that old Doctor, I can still get it up," said Derek.

The Doctor laughed and said, "You know what I mean Derek. As they want total discretion and don't want you to see them you'll all be blindfolded and as you'll be getting no visual stimulation you, Simon and James will all get a shot of Caverject to keep you hard, the joys of youth means that I don't think that Sam will need it."

Fuck, I thought, I hadn't had an injection in my cock before.

Nurse Sally wheeled a medical trolley across with a tray of hypodermic syringes on it and said, "Drop them please gentlemen," and we did as we were told.

Simon was first, he knew the routine and held up his cock so the Doctor could get to the underside of his shaft, she said, "Full dose for you, need you rock hard for your medical later no matter what we do to your arse or cock."

"Pump it in Doc, I like a prick," Simon laughed.

"You next James, hold your cock up by your foreskin so I can swab the underside of your shaft and give you the shot, just take a deep breath and breathe out as I inject you," Doctor Mac told me.

I gritted my teeth and breathed out, most men don't want anything sharp near their cock, I felt a sharp prick and some cold liquid flowing into my soft cock followed by another sharp prick and the cold feeling again and then the Doc said, "All done, just rub where I've giving you the shot for a few minutes."

"Well who's a brave boy?" laughed Simon, "Let me rub it better for you," and he reached out, grabbed hold of my cock and rubbed the shaft up and down," I let him do it, I had no problems with it.

I heard Derek say "fuck" under his breath as he got his shot into his cock and his son laughed and said, "I don't need that to get me hard do I Aunty?"

"Oh go on then, I better help you out," Sally said and I watched as she pulled the front of her nurses uniform down to let her big tits spill out and then lifted her skirt up to show off her bald fanny and bent over slightly.

Sam didn't waste any time as his Aunt fed one of her red hard nipples into his mouth and he sucked away happily like he was breast feeding and his hand found her fanny and he pushed two fingers in and started to frig her off hard, the stimulation had the desired effect on his cock.

"When you've quite finished Nurse" Doctor Mac said sternly, "Gents we'll be back in fifteen minutes."

Sam pulled his fingers out of his Aunts, by now, wet fanny and just like lads do held them up to his nose and sniffed them and said, "Very nice Aunty."

Derek just smiled and said, "I gave up trying to stop the dirty little fucker, his Aunts as bad as him."

The injections in our cocks had the desired effect and my cock was soon rock hard and my foreskin rolled back. None of us men were shy about what we had between our legs and chatted away as if it was the most natural thing in the world to sit there naked with a hard cock. Simon groaned and said, "Look at this fucker, its going to burst," his cock was very hard and sticking straight up in the air, you could see all the veins along it and the glan of his cock was fully exposed and looked like it was throbbing.

I couldn't resist it and laughed saying, "You've got hours of that ahead of you as well."

I checked out Derek's and his sons cock, Derek's was a decent length but very thick, reminded me of my flatmates cock, the head of his cock was still covered by his foreskin and his son said, "Here we are old man, let me give you a hand," and reached out and pulled his fathers foreskin back from his cock head to expose a slash of a pisslit.

His son, Sam's, cock was completely different, much thinner than his Fathers, maybe only an inch and a half in diameter, but much longer, longer than all of our cocks, a good ten inches with a big foreskin hanging down covering his cock head making it look like he had another inch to his length.

Sam saw me looking, smiled and said, "That's why Dad and I work together, Dad stretches their cunt or arsehole open wide and I go in and give them a few more inches, hits their spot and makes their eyes water." Sam was a cocky fucker but with a cock that long he could afford to be.

The Doctor and Nurse came back into the room, "Lets get you masked up, the clients are waiting, they've had a few glasses of bubbles so are nicely relaxed and all their inhibitions have gone. Stand against the wall over there with your cocks on show, Nurse Sally and I will be staying here to guide your cocks into their holes as you wont be able to see where you putting it," said the Doctor.

The Doctor pulled a mask over my head, not sure what I expected but it wasn't this, it was like a mask that Batman used to wear, a half mask made of black latex, it went over the top of my head covering my eyes and with a shaped nose piece that sat over my nose so I could easily breath and a strap that went under my nose and around the back of my head and was fastened up by the Doctor so no way was it going to fall off, there was cut outs for my ears so it wasn't uncomfortable and I could easily hear, one thing was guaranteed and that was I couldn't see anything. I heard Simon say, "Fuck me mate, you look scary in that, wouldn't want to meet you on a dark night out dogging."

The other three had their masks strapped on and the Doctor said, "Right gents, you all look ready to perform so I'll bring the clients in," my cock twitched at the thought of holes to fuck.

A minute of so later I heard the Doctor say, "Well here you are ladies, here's the cocks that you ordered, hard and ready for your use. The Nurse and I will stay here to help you out, as they can't see where they're supposed to be putting their cocks. Please get closer and inspect and play with them."

"Oh Joan, aren't we the lucky old ladies, look at them, all hard and just waiting to fuck us," said one of them.

"Susan you've turned into such a cockslut, there's some advantages to having rich husbands who can't get their little cocks hard anymore and don't mind us getting fucked still, well as long as we're discreet," the other one said.

"Please ladies, don't be shy, come and handle the goods," the Doctor laughed.

At that point I felt like a bit of meat in a butchers shop but then I suppose I was, just a length of cock for sale.

"This is James, one of our newer lengths of cock" Doctor Mac said and I sensed that the two ladies were standing by me but I still tensed as I felt their hands on me as they ran them over my chest, arsecheeks and of course my cock and balls. There was comments like, "oh look at the muscles and the beautiful chest" as they pinched my nipples or "the arse cheeks are so firm" and a hand slapped them, "look at the veins on his cock" and "his foreskin is so loose" and then my balls were yanked down hard with the comment "that metal ring certainly makes them hang down low."