Jill's Story - Sex, Sex & More sex Pt. 08

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Jill & her Mother + 2 cocks & Jame's first job at the clinic.
17.9k words
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Part 8 of the 12 part series

Updated 12/23/2023
Created 08/07/2022
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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, her ex boyfriend Pete and her new boyfriend James and 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 story features incest so be warned.

This chapter of this story also features gay sex and what could be considered a gay theme in one section.

"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.

JILL

I was awake first, James was asleep on his back next to me, he'd pushed the duvet partly off so that I could admire his muscled chest, his clippered hairy chest and his tattoos. I'd got myself a real man.

I pulled the duvet off of him to expose his thick thighs, washboard stomach and, of course, the most important part of a man, his cock and balls. His legs were parted so his big waxed and I hoped full balls hung down between them and his thick soft uncut cock lay across one of his thighs, his foreskin covered his cockhead.

I hadn't let him fuck me before we went to bed last night but had promised him an early morning fuck and I hadn't even let him have a shower after his cock had been working hard at the clinic fucking a clients arsehole, mind you he hadn't let me have a shower either after being fucked by two clients and James bringing me off in a spectacular climax when we got back to his flat before going to bed, we were both dirty.

James didn't stir as I moved between his open legs and positioned my face near his bull balls, I could smell him, the smell of man sweat, he smelt musty, he smelt good. I moved closer to his soft cock, I took a deep breath, the smell of piss, dried spunk and smegma hit me, I trembled and gently grabbed hold of his soft cock and pulled his foreskin back, that's what I wanted, his cockhead glistened with his smelly cock juices and as I'm a tidy kind of girl I thought that I'd better clean his cock up.

I licked his cockhead and pisslit savouring the acid taste of piss and smegma before taking the head of James's soft cock in my mouth and using a hand to cup his balls. I used my other hand to rub my fanny lips that were starting to get wet; I pinched my clit gently to get my juices flowing before pushing two fingers into my cunt.

James moaned gently as his cock started to fill with blood and stiffen and I took his cockhead into my mouth sucking gently, trying to get the last bits of smeg off of his cock and felt his cock swell and stiffen in my mouth as I frigged my fanny hard with my fingers getting it wet and ready for cock.

James's swelling cock filled my mouth and I took more of his cockshaft down my throat as I heard James say, "Morning Jill, take some more of my cock," and he pushed my head down further until my nose hit his firm midriff, I didn't even gag as he held my head down.

When he released me I pulled off and smiled at him, "good morning," I said and went to work on his cock and balls, licking and sucking until his cock was covered in my spit and saliva. I pulled off of his cock and looked at it, it was hard, skinned back and his cockhead was purple showing off his open pisslit.

I leant back so he could see me fingering my fanny and pulled my wet fingers out and held them up to his mouth, he opened his mouth and let me push them in so he could taste my fanny juices.

I was in charge and squatted over him, held the base of his hard cock and slapped his cockhead against my wet fanny lips and when it was coated in my fluids I inserted the head of his cock into my fuckhole. James tried to lift his hips so that the full length was pushed into me but I smiled and lifted myself up so his cock fell out of my hole. James got the hint and stayed still as I lowered myself slowly back onto his cock feeling the head open me up, the shaft stretch me and rub against the inside of my cunt, I grunted as the full length filled me until I bottomed out on his hips. I could feel James flexing his cock muscles inside my hole stretching me even further.

I lifted myself up feeling the length of his cock slide out of my fanny and only stopping when the head of his cock was about to pop out and then lowering myself back down again until I was full of James's cock. James held my hips to steady me as I started to fuck myself quicker and harder forcing myself down on his cock.

James grunted and his cock seemed to get bigger inside of me, a sign that he was going to spunk up. I was close to cumming as well but I wanted him to fill me up first, I lifted myself up off of his cock till just the head of his cock was inside my and I worked my cunt on his purple cock glan. James grunted and his cockhead started to swell and he shot his load spraying it into me and coating my fuck tube with his cum, shot after shot inside me and I lowered my fanny down on his cock so that my fanny and his cock was lubricated and coated in James's spunk. James's cock stayed hard even though he had emptied his balls into me and I fucked myself hard on him taking his cock right up to his balls while gently rubbing my hard clit, I was going to cum and James said, "Go on Jill, cum on my cock."

He thrust hard into my wet spunked up cunt and I pinched my clit and came, bucking on his cock and milking the last drops of spunk out of him by squeezing it with my fanny muscles. James held me tight as my climax ripped through me as I fucked myself on his cock through my orgasm. I was breathing deeply as I stopped fucking myself on his cock as James's cock started to go soft inside my wet well fucked fanny.

"That was good," James said with a big smile on his face as I lifted myself off of his shrinking cock and held my well fucked fanny lips open letting my fanny juices mixed with his cum drip out over James's cock and balls.

"Dirty girl," James laughed and grabbed hold of his cum covered cock and wanked it gently.

"You'll have to change the sheets now won't you? They're covered in our mess," I told him, "I've got to have a shower and get to work," and kissed him.

James and I seemed to be getting on well, I stayed at his flat most nights and our sex life was amazing, we fucked our way around the flat and James used all of my holes hard. We also had a social life, which I hadn't had with his brother. We both loved hard uninhibited sex so would often end up at the dogging site on our way back from a restaurant or the cinema and of course if we needed another length of cock to join in then his flat mate, Tom, was always happy to provide his beer can thick cock.

A few days later I was at work when my mobile phone bleeped, I had a WhatsApp chat message. Dad didn't like personal phones in the office but I was the boss's daughter, I had my own office and Dad was away for a few days, there's got to be a few perks being related to the boss.

The chat was from James.

James: "Hey beautiful, having a busy day at the office?"

Me: "Hey there big boy, how's it hanging? Up to my eyes in work."

James: "Just thinking about you makes it hard! Doctor Mac has asked me to work tonight at the clinic. You OK with that?"

Me: "Of course, its your job."

James: "As long as you are otherwise I'll cancel."

Me: "Just go and do it but don't wear your cock out, I have holes that need filling with it!"

James: "Yes Mam. Will you be at the flat when I get back?"

Me: "No."

James: "Oh."

Me: "Don't worry I'm not leaving you, Dad and my brother are away for a few days so I thought I'd go and keep Mother company, we're going to have a girls night in, she's even organised a masseur for us tonight."

James: "Oh yes, a masseur, so you and your Mum are going to get some cock tonight?"

Me: "Why, would you be jealous? Don't worry the masseur is gay and happily married so I don't think he'll want to put anything near my fanny."

James: Well as I'll be fucking tonight I can't criticise if you do get some cock tonight can I?"

Me: "Don't worry my holes are yours and you know it. Message when you get home and tell me all about it - XXX."

James: "I'll be a good lad and save some spunk for you - XXX"

I suppose that I should have been upset of jealous of what James was going to get up to at the Clinic but I wasn't, I was excited, I was jealous of not being involved.

JAMES

I was nervous about working at the clinic for the first time, well the first time officially and also nervous about what Jill would say when I told her about my first job there. Of course I needn't have worried about Jill, I think that she secretly enjoyed that her boyfriend, I think that I was by now, was a sexworker, as long as she got my cock when she wanted she was one happy girl.

I showered, checked my cock and balls were hair free, they were as I'd had them waxed about ten days ago, gave my cock a stiff talking to about getting hard when it had to perform and dressed in a tracksuit, I guessed I wouldn't have it on for long when I got to work and waited for the car.

My phone bleeped to say the car was waiting for me; I picked up my bag and headed downstairs. I got in the car and off we went, I didn't know the driver, turned out he was one of the security men, and we soon got to the clinic and drove around the back where the Doctors son, Charlie, was waiting for me.

The driver said, "Enjoy mate," with a big grin on his face.

"Hey there James," said Charlie, "I know its a bit early but we just need to go through a few things with you before we get down to the fucking."

"No problem with that mate," I told him.

"Shower first and then Dad wants me to fit you with this clinch ring round your nut sack," Charlie said showing me the ring that he was holding. His Mother had said that the clients liked a big pair of swinging balls and the ring fitted around the ball sack stretched the sack down and certainly made the balls stand out and look impressive.

"Don't worry mate, I'll give you the key to take it off when you've finished here although I keep mine on permanently, certainly makes the lads at the gym look twice when I'm in the showers," Charlie laughed.

Charlie started to strip off, looked at me and said, "Come on, let's get showered."

"Its OK mate, I showered before I got here," I told him.

"Did you wash your arsehole out though?" Charlie asked and I saw that he was holding a douche nozzle attached to a hose that was hanging in the shower.

I swallowed hard and said, "I had my soapy finger up there so I'm OK," hoping that that would do.

"Sorry," said Charlie with a smile on his face, "not good enough. I know you won't take cock up your arse but if the client wants to finger you or use a toy on your arse you've got to be squeaky clean. Don't worry its not going to be an enema just a douche to get you clean."

I suppose it had to be done so I got undressed, Charlie was already naked showing off his big black cock and his balls hanging low with a silver ring around them. He had a muscled fit body that looked even better with his ebony skin. He was happy with cunt as well as cock and I'm sure that his cock was starting to harden, I didn't have a problem with a mans hard cock, couldn't really avoid a hard cock when we were all fucking together.

"OK James, lube your arsehole up," he said and threw me a bottle of lube. I did as I was told, I should have been embarrassed about fingering my arsehole in front of a man but I wasn't, it was part of the job.

"I'll help you this time with the douche but next time when you get here you can do it yourself but don't worry there's always somebody around to lend you a hand, if you're lucky it will be one of the nurses, it will become just part of your pre fuck routine," Charlie laughed.

"You just want the water to be warm and you don't need a high pressure jet just a trickle of water," Charlie said and handed me the cone shaped nozzle that had water gently spraying out of the holes around its tip, "Get in up your arsehole, just relax and it will go in easily."

I bent over and spread my legs, put the end of the nozzle against my ringpiece and pushed. Charlie was right, the nozzle slide in easily right up to the base so it wouldn't go in any further. I felt the warm water starting to fill my arse, it was a strange sensation.

Charlie said, "When you feel full let it carry on for a few seconds and then pull the nozzle out, make sure you clamp your ringpiece shut, you want to hold the water in your arse for a while."

My arsehole was full, felt like a needed a serious dump, I grunted as I pulled the nozzle out of my hole and clamped my ringpiece closed tight but I knew that a few drops of water dripped out. I stood up, my stomach felt OK, my arse felt full and I realised that my cock was rock hard, fuck.

Charlie laughed and said, "Don't worry mate, the douche nozzle and water is pressing on your prostate so your cocks just responded" and he dropped down onto his knees in front of my hard cock and grabbed hold of my balls and pulled them down hard.

"Fuck mate," I exclaimed, at least he didn't try to suck my cock at the same time.

"Keep your cock out of the way so I can fit this ring around your balls," Charlie told me and clamped the ring around the tight skin of my ball bag forcing my balls down. He'd was an expert, didn't pinch my skin and quickly secured the silver metal ring around my ball bag. I could feel the weight of it and a slight ache was already starting but that was the least of my worries, I needed to empty my arse.

Charlie stood up and grabbed hold of my hard cock and looked at me and with a smile ran his fist up and down the shaft of my cock gently wanking me before saying, "Right mate push that water out, empty your arse," and he turned the shower head on so the water was spraying. I grunted and forced the water out, spraying it over the floor of the shower and down the drain. How embarrassing doing it in front of another man.

"There you go mate, that wasn't that bad was it?" Charlie asked, "Get it back up there and fill your arse up again, I'll join you."

Fuck knows what anybody would have thought if they walked in on two grown naked men bent over in the shower with their legs spread open, a hose up each of their arseholes sporting rock hard cocks and grunting as they douched. Actually now I had the hang of this place they probably would have thought it was just a normal day at the clinic.

"Right," said Charlie as we finished douching, "Dry yourself off, put these on and we'll go and meet Dad and the other fellow cocks." He laughed as he threw me a set of baggy training shorts and we walked down to the "examination" room.

I hadn't been in this room before, it was set up for fucking, four low fuck benches, a big leather covered mattress on the floor and a leather covered sofa, there was a trolley in the corner with bottles of lube, a few large dildos, butt plugs and leather restraints, everything needed for fuck session.

Doctor Mac was there and said, "Ah here you are James, let me introduce you to your fellow cocks, I think you know Simon and this is John."

It was Simon that I worked with when I worked with Noel the gardener; well we did more than just gardening as Noel also provided a fuck service for the bored housewives so Simon and I had already fucked together.

"I didn't realise that you worked here as well Simon," I said.

"Discretion is the word here mate," said Simon, "When Doctor Mac asked whether you could handle the job I just said that you had a big cock, knew how to use it and was a dirty fucker so you'd be ideal."

"Well thanks for the recommendation mate, I owe you one," I laughed.

John and I shook hands, very formal, the man thing to do. It was a bit unnerving as John was naked. He was older than all of us, early fifties I suppose. Dark haired and obviously very fit, very defined and not carrying an ounce of fat, no body hair apart from his trimmed pubes. His cock was hanging between his legs, long, fat and uncut. John said, "I hear this is your first official fucking session, don't look so worried, you'll be fine, just think of the money."

I laughed and Doctor Mac said, "Right it's going to be a hard session so lets get you all prepped," and he uncovered a medical tray that had a bottle of tablets and hypodermic syringes. Fuck, what was he going to do with those?

"You first son," the Doctor said to Charlie who nodded and stepped out of his baggy training shorts. "All douched out?" the Doc asked and Charlie nodded. "Good lad, hold your cock up for me so I can give you a shot of Caverject," he told him and picked up one of the syringes.

Charlie held his cock up so his balls and the underside of his cock were on show to the Doctor who swabbed his cock with an antiseptic wipe and then pushed the needle into the underside of his sons cock near the base of the shaft and to one side of the big thick vein than ran up his cock. Charlie winced and took a deep breath as his Dad pumped about half of the contents of the syringe into his sons cock before pulling it out and pushing it into his sons cock again but this time the other side of the cock vein.

He finished the injection, pulled the needle out and said, "All done son, just massage your cock, you know what to do."

Doctor Mac stood in front of me, I stood up and dropped my shorts, my cock was already half hard and filling with blood, "the cockring looks good on you James, makes those balls look big and round, she'll love those slapping against her arsehole when you're fucking, I know you've douched just in case," the Doc said, he must have seen the look on my face as he quickly said, "Don't worry you wont be getting fucked, well at least not today."

"Don't think I want a needle in my cock Doctor," I quickly said as he pushed the medical tray towards me.

"That's no problem James, I'll just give you a Viagra tablet, it will help keep you hard during this session," Doctor Mac said and handed me a tablet and a glass of water.

"I'll have one of those Doctor," said John, "You're not going to prick my prick with a hypodermic."

Doc Mac said, "If you haven't used Viagra before James you might feel a hot flush and a dry mouth but I know you're a fit lad so that will soon pass. RIght, just you Simon, I don't need to ask what you want."

Simon stood up, pulled his cock and huge balls out of his jockstrap, that was the only underwear Simon ever seemed to wear, and said, "Just pump it in Doctor."

"I see you've had your balls pumped up again Simon, they're looking good," the Doctor said and held Simons tight ball sack before plunging the hypodermic syringe into Simons cock shaft, Simon didn't even flinch and as the Doctor gave him his second shot Simon smiled, I think that he enjoyed the pain of a needle in his cock.

"OK gents, tonight's clients. Big spenders, husband, wife and daughter," the Doctor said, I could already feel my cock getting hard, the Viagra worked fast I thought.

Doctor Mac carried on, "Husband is in his early fifties, keeps fit, average sized cock, likes to be dominant with his wife and daughter, likes to see them fucked hard. He might just watch tonight's proceedings or might join in, he'll probably want to arse fuck one of you just to show he's the alpha male," he must have seen the look on my face as he said, "Don't worry James, Simon or Charlie will take his cock up their arse so you can relax but just to put the husband in his place in front of his wife one of you can arse fuck him, Charlie and Simon can toss for it, well not literally as I don't want you to waste your spunk."