Nisan 24, 2023

Simon Says – My Story Pt. 08

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Chapter 8

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. Simon is one of the characters featured from outside of the family. This story explores his sex life.

Please note that I am the original author of “A FAMILY THAT PLAYS TOGETHER STAYS TOGETHER” and the original author of “SIMON SAYS – MY STORY”



I was starting to get worried that at the rate I was going that I’d wear my cock away with all the sexwork that I was doing.

I was working at The Club for a few days or evenings a week; sometimes I’d be there for days on end. I was working with Noel on a regular basis, gardening, which was my fallback earning, and of course fucking the clients with him. Craig, who I’d worked with at The Club, we’d met performing a teacher / pupil scenario that had also involved fucking my Mother, had asked me to work with him, he was an escort and had a string of regular clients and he needed another length of cock to help him out.

I didn’t want to fallout or disappoint any of them.

Noel was fine about it and said that as long as I could get my cock up and perform when required then he had no problem. None of Noel’s clients use Craig’s services, or so I thought, so Craig and I wasn’t pinching any of Noel’s clients.

Doctor Moore was OK as well. Craig and I were both some of his best stud cocks and holes so he didn’t want to loose us and as long as we were discreet and available when he wanted us to perform then he had no problem.

So it looked like Craig and I would be working together.

Craig was a nice bloke, we both have similar interests, gym, football, rugby and of course sex. We both had similar sized cocks, both had very few inhibitions and were both fucking to build up a university fund although I think that, maybe, I was beginning to have second thoughts about that. He had no problem with the gay or bi side of sexwork; it meant that you could get a lot more work.

It was good to have somebody about the same age as me that was working as a sexworker, meant that we could be open about it all when we were together. We both smiled when we were out with the lads from the football or rugby club listening to them boasting about what they’d got up to with their wives or girlfriends or what they’d like to get up to with them, we’d look at each other and think that we’d already done it and got paid for it.

My Mum had already met Craig, Craig had already fucked her when we were all working at The Club, she liked him and thought that both of us working together was a good idea so had the bright idea of asking him to the house for dinner one evening, “So I can get to know him better” Mum said. She’s already had his cock in her fanny so how much more did she want to get to know him?

It took a bit of organizing as it seemed my Mother and sister were always booked for clients or Craig and I were working at The Club but we found a free evening so a few days later Craig arrived at our house about seven o’clock, he’d done the right thing and bought a bottle of decent wine.

“Hello Craig, lovely to see you again, last time we met you were shooting your load of spunk over my tits and then licking it up” said Jenny, my Mum.

Craig laughed and said “And I loved every moment of it Mrs. Scott.”

“Oh call me Jenny, you’ve fucked me after all so I think that we’re on first name terms” Mum answered.

My sister, Jo, appeared, I’m sure that she could sniff out fresh cock.

“Craig, this is my sister Jo, she works as an escort as well. I think that it runs in the family,” I told Craig.

Craig gave my sister a friendly kiss, I saw my sisters hand rub over Craig’s cock bulge. I knew how the night would end!!

It was a good meal, Mums a great cook, the wine and conversation flowed, most of it about sex work, Craig was a new boy in the job so I think that he was a bit shocked about some of the stories that came out.

Craig jumped and Jo said, “I think that he’s getting excited about these stories, I can feel he’s getting hard.” As always my sister was being a slut and was already checking out Craig’s cock bulge under the table.

“Right, I cooked so you boys can clear up and load the dishwasher, make yourselves useful and then you can have your dessert” said Mum.

Out in the kitchen Craig said “Wish my family were like yours, open about everything, if my parents ever find out about what I’m doing for a living I’ll get chucked out on my ear, and your sister is fucking hot, have you fucked her yet?”

“Certainly have, for work of course, never for pleasure. Lets go and get our dessert,” I said. Craig laughed.

I sort of knew what to expect before we both walked back into the living room and I was right, Mum and sister were sitting naked on the sofa, their legs were spread wide open and they both had vibrators that were buzzing away shoved deep into their wet fannies.

“Come şanlıurfa seks hikayeleri on lads, told you it was time for your dessert so what are you waiting for, strip off and come and get fed,” demanded my Mum.

As Craig and I stripped off, Mum and sister pulled out the vibrators from their cunts and held them up to us. Like two kids given lollipops Craig started to lick the fanny juices off of my sisters vibrators and I did the same to the vibrator that had been deep in my Mothers open cunt. My Mum tasted good.

Craig licked his lips and said, “You taste so good Jo but you could have turned off the vibrator first, nearly rattled my fillings loose.”

We all laughed and Mum said, “You two lads go and shower and we’ll be waiting for you.”

Craig looked at me and said, “I’m fine, and I showered before I got here.”

Mum laughed and said “You really need to learn a few things about working in the sex industry. Simon, take him upstairs to the shower room and show him the shower, and you shower as well.”

Craig and I went upstairs to the shower room, I said “Hey mate, this is an equal opportunities house so if we want to use Mum and sisters holes then we have to be up for them using our holes, fairs fair.””

Craig laughed “I’m with you now.”

He saw the douche nozzle hanging in the shower and we both stripped off. “We’ll take it in turns mate, you first” I told him, “Lubes in the bottle.”

I sat on the toilet and watched him lube up his arsehole and the nozzle and then push it into his hole, he winced a bit, his hole wasn’t as used to being opened up as mine was. He turned the douche tap on and let the water fill his arse. Like me, as the pressure built up in his arse and put pressure on his prostate gland his cock started to harden. I watched, neither of us were embarrassed about douching, getting hard or emptying out our arses in front of each other, it had to be done and if we were going to do more work together we couldn’t afford to have any inhibitions.

“Got to let go mate” Craig said and pulled out the douche nozzle and gave it to me, I lubed my hole up and pushed it in, Craig and I swapped places and I let the water jet into my arsehole.

When we were finished we put on our underpants, well I put on my jockstrap, I need the support for my pumped up nuts, and Craig pulled on his designer tight boxers. “You ready for your dessert mate?” I asked him.

“Defiantly ready for your Mums and sisters holes so lets go,” said Craig and he almost ran down the stairs.

Mum was on the sofa, legs open wide and my sister had her head between them and was licking away on her Mums fanny.

“You started without us Mum,” I said.

“Oh there’s plenty of holes to go around so don’t worry. Your holes and cocks nice and clean lads?” Mum asked.

Craig and I nodded; our cocks were hard and trying to escape out of our underwear.

My sister Jo stood up, her face was covered with my Mums fanny juice, and said “On your knees lads and let Mum and I check your arseholes and cocks out, so drop those pants and jocks.”

We stripped off our pants, dropped to our knees and spread our arsecheeks. I looked at Craig and he looked at me, we both had stupid grins on our faces.

Mum was behind Craig and my sister was behind me and I jumped as I felt Jo’s wet tongue on my pucker, Craig sighed as Mum pushed the tip of her tongue into Craig’s tight pucker. They were eating our arseholes out; it’s great getting rimmed by your sister. When we were wet and starting to relax I felt a lubed up finger penetrate me and I watched Craig push back onto my Mums finger that was deep in his arsehole.

I knew what was coming next as the finger was pulled out of my ring piece and my sister said, “Relax both of you” and I grunted as I felt my pucker stretched open by what felt like a big wide butt plug.

Craig was panting and looking at me as if to say “What the fuck is happening?” and then he let out a low groan as my Mum pushed the butt plug all the way in. Jo slapped the base of the butt plug that was fully up my hole and said, “There you are Si, you’re plugged.”

I bloody well know that, I could feel it all the way in there.

Craig moaned and said, “Fuck me, that’s big, my arsehole is stretched.”

Jo said, “Now you know what it feels like when you men arse fuck us women.”

Mum and Sis took up their positions on the sofa, on their backs, legs spread wide open. Mums fanny was open, she’s older and has been well fucked so her labia fall open naturally, my sister’s fanny was tighter and closed, more like a slit than a gash.

The ladies clicked their fingers and pointed at their fannies. Craig and I didn’t need telling twice and dropped to our knees and buried our faces in their cunts, kissing, licking, chewing, teasing and fingering. We were both rock hard, our arseholes were plugged. I had one hand on my cock and one hand on my Mums clit while Craig was using his hands to pull open my sisters tight gash so he could find her clit and her fuckhole.

Mum pushed my head deep into her fanny, she was sliding it up and down my face so my tongue licked her slit and then locked onto her hard clit. She was moaning and muttering “Yes son, that’s it, eat out your Mums cunt.” Her dirty talk made me even harder.

Craig called out “I’ve got to fuck you” he looked at me and said, “Can I fuck your sister please?”

“Go for it mate, looks like my sister needs your cock in her cunt, just look at it” I told him.

My sisters cunt had opened up like a flower, it was all pink and wet and I couldn’t resist it, I leant across and pushed two of my fingers deep inside her hole, pulled them out and licked them, my sisters juices tasted good.

Jo leant forward and grabbed hold of Craig’s cock and pulled him forward, he got the hint and thrust into her with one long hard push.

Not wanting to be left out I coated my cock with my Mums fanny juices and thrust into her as well. She sighed and said “Good lad, fuck your Mother hard.”

Craig was fucking my sister hard, very hard. She was taking it, of course, she’s a professional, but even she was squealing and her legs were twitching, Craig grabbed hold of them and spread them even wider. Craig’s cock isn’t huge, big enough and thicker than mine so it had obviously found my sisters spot. I followed Craig’s lead and started to use my Mothers fanny hard.

It really is special, and very horny, fucking the hole that I’d been born out of, fucking your Mothers cunt. Every time I thrust deep into my Mothers hole and she gripped my cock with her fanny muscles the butt plug in my arsehole would hit my prostate gland and give me another belt of pleasure, my cock was getting pleasured and so was my arsehole.

Craig was grunting, I was grunting, Mum was moaning and my sister was whimpering.

Just as we were approaching our spunking up point Mum said, “All change” and pushed me out of her fanny. My cock twitched and pulsed, I was trying to hold my spunk back.

“Change partners and change holes,” my sister shouted out. I shuffled across to my sister, well you try walking normally with a plug up your arse, and lifted her legs up almost over her head so her arsehole pucker was on show and available. Craig flipped my Mother over so she was on her knees, well she is an older women so not as supple as my sister, and slapped his hard wet cock on her pucker.

“Lets fuck arse Craig” I said and pushed the full length of my cock into my sisters open and relaxed arsehole.

She took it with a grunt and said “Bastard arse fucker.”

Craig was more of a gentleman and slowly pushed his cock into my Mum’s arse pucker inch by inch, well his cock was thick. When he was through her sphincter he pushed the last few inches in hard and strong.

Jo’s hand went between my Mothers legs, found her clit, I saw my Mum jump so she had the right place, and started to rub it. I started to rub and pinch my sister’s clit and she smiled back at me.

Craig and I were fucking their arseholes hard, we were panting with the exertion, the pleasure from our cocks deep in their arses and from the pleasure of the butt plugs up our arseholes.

“Oh God Craig, I’m going to cum, fuck my arse hard, Jo rub my clit hard” shouted my Mum.

We all did as we were told, Craig pounded my Mums arsehole, Jo was pinching Mums clit and I, almost the odd man out was still fucking my sister’s arsehole.

Craig pulled my Mother up and held her tight, actually he was pinching her nipples, shoved his cock right up her arsehole as far as it would go, Jo pinched my Mums clit hard and this pushed Mum over the top and she orgasmed, moaning, screaming and shaking. Mum was a squirter when she came, fanny juices and piss squirted out of her cunt all over the sofa, lucky that its leather so it would wipe clean.

Craig didn’t stop fucking her arsehole, he was having to hold my Mother up so she didn’t collapse as she was still shaking.

“Enough, enough” she moaned and Craig pulled his cock out of her arsehole with a plopping noise, “Nice big gape Mum” I said laughing. That wasn’t a good idea I realized later.

Mum collapsed and I pulled my cock out of my sister’s arsehole.

My sister grabbed hold of mine and Craig’s wet cocks and wanked them slowly just, edging us to keep us hard and close to spunking up. It gave Mum time to recover and she stood up, her fanny was still dripping juice and piss, and said “Time to empty your balls lads.”

We both smiled, assuming that we’d be getting a blowjob from the ladies or at least wanked off by them. We were wrong.

“Bend over both of you and lets get those butt plugs out of your arseholes. We bent over and Mum eased them out. Craig sighed and I flexed my sphincter muscles to open and close my arsehole.

“Lets have a look Mum,” said my sister, we turned so she could see our holes, “Oh look Mum, they’re both open as well.”

“Well we better do something about that then hadn’t we” said Mum and she picked up two big dildos, they were both long and thick, one bigger than the other, both had a big set of artificial balls and a grip on the end so the dildos could be held. I knew what was going to happen, I shouldn’t have laughed at Mums arsehole gape.

“Time to you let you shoot off boys, you’ve fucked us hard so now its our turn to fuck you” Mum said.

“You first Craig, as you’re our guest, so bend over and lets get this in you, you’re already open and lubed up” she said.

Craig looked worried looking at the dildos and said “I can’t take that big one in my hole, it will split me in two.”

“Don’t worry,” said my sister, “The big one is for my brothers arsehole, he shouldn’t have laughed at Mums gaping arsehole, he won’t be laughing when that big dildo is up his arse though.”

I swallowed hard.

Craig bent over slightly and moaned loudly as my Mother pushed the dildo deep into his arsehole until the set of balls stopped it going in any further. My sister was on her knees in front of him, holding his balls and gently stroking the shaft of his hard cock.

“Your turn son” said my Mum and I bent over slightly and spread my arse cheeks.

I felt the tip of the thick dildo touch my arsehole and tried to relax and push out so my ring piece opened up. Mum carried on pushing even though I was yelping as it pushed through my sphincter. It went in deeper and I could feel my hole being stretched, it was stinging as it got opened up more and more. “It’s too big Mum, no more please,” I pleaded with her.

“Don’t be a wimp in front of your mate, he took his dildo without complaining so you can take this, only a few more inches” she laughed and with that she pushed the last few inches up my hole and I felt the set of balls hit my arse. I just moaned loudly.

My sister, Jo, licked the end of my cock and held the shaft firmly. “I can taste precum Simon,” she laughed.

“OK lads, brace yourself, I’m going to fuck the spunk out of you” said Mum and she started to pull the dildos almost all the way out of our arseholes before pushing them all the way back in till the balls hit our arsecheeks.

Craig and I held onto each other, my sister was on her knees in front of our hard cocks just teasing us, edging us waiting for our hot spunk. You could smell the tension in the air, you could smell the sex in the air, we were both moaning, I could feel my balls churning, Craig’s jock was jerking and the veins were bulging along the length of his cockshaft.

Mum picked up the speed of the thrusting, fucking us both up our arseholes with the big dildos. I was close, my arsehole had been plugged, I’d fucked my Mother and sister in their cunts and arseholes and hadn’t come yet, and I needed to spunk up.

Craig shouted “I’m going to cum, I need to spunk” and with that he let go of a huge load firing thick wads of his spunk out of the end of his cock, firing it across my sisters face and tits, six thick hard shots. I could hear him panting as he pushed his load out of his balls. I thought that he was going to collapse afterwards so lucky I was holding him.

I looked down at my sisters spunk covered face and tits, it was dripping off of her chin onto the carpet. She looked at me and said “Your turn little brother” and with that she took the head of my cock in her mouth.

Mum pushed the dildo right into my arse and it hit my prostate, I growled and my balls started to pulse, pushing my cum out into my sisters mouth.

She was swallowing hard, trying to drink it all but with my huge load she had to give up and pulled off of my cock so the last shot of my spunk hit her in her face.

Mum pulled the dildos out of our sore and open fuckholes; she dropped to her knees and took Craig’s cockhead in her mouth, cleaning off the last trickle of spunk. She held hold of my balls almost massaging them and licked up the last drops of my cum.

I pulled my sister off of her knees and Craig and I both kissed her, who cares that she was covered in both of our loads; we’d both done a lot worse at The Club. I pushed her onto the sofa and Craig spread her legs open, he then stood over her and pushed his arse into her face so she had his gaping arsehole right in her face.

“Eat it out Jo,” and from the slurping noises that she was making I guess she was, “That’s it, get your tongue in there.”

I picked up the big dildo that had been up my arse, held open her cunt lips and started to fuck my sister with it. She took it all in her fuckhole, well she was soaking wet. Craig bent down, he was an athletic fucker, so his arsehole was pushed into my sister’s face, and squeezed her clit.

She screamed, not that you could really hear her as the scream was muffled by Craig’s arse, and with another thrust of the dildo up her fanny my sister orgasmed, she orgasmed again and again. I pulled the dildo out of her cunt and she fired a stream of her juices out of her hole all over me.

A little bit later we were all sitting having another glass of wine as we came down from our orgasms, the room smelt of sex juices, piss, spunk and lube. We were all still naked, like most men Craig and I were still playing with our soft cocks, I was just pulling my foreskin backwards and forwards while Craig was playing with his, by now, empty balls. Mum was stroking her clit gently and my sister was fingering her fuckhole.