Simon Says - My Story Pt. 01

"Slow down big boy, you can't spunk up within the first ten minutes unless your a multiple cummer but we'll find that out wont we. You need to pace yourself, give the client their monies worth, they might have paid for a couple of hours so unless they want you to cum right at the beginning of the session you have to save it for the end" Noel instructed.

"Anal or arse fucking next, what ever you like to call it, turn over ladies, on your knees and present those arseholes to your son" Noel told them.

Mum and sister turned over and their arsehole puckers winked at me. Noel and I stood there with our hard cocks sticking out in front of us.

"You've got to remember that an arsehole has no natural lubrication so you either use lube or spit. Your Mum and sister love anal so their holes aren't too tight and they know how to relax them so they can both take big cocks can't you girls." Mum and sister both nodded.

Noel carried on. "There's nothing better than the look on a women's face when she takes cock in her arse, the pain as the cockhead forces through the pucker and then the look of pleasure as they take the full length. You fucked arse before Simon"

I looked embarrassed and said "no."

"So here's your chance, your an anal virgin. Get on your knees and get your sisters arsehole nice and wet and open, use spit and your fingers," I was told by Noel.

I was going to lick and finger my sister's arsehole...what the fuck was going on?

Jo pulled her arse cheeks apart and I could see her little pink hole, it was beautiful. I leant forward and started to lick all around it and across it, she moaned as I started to push the tip of my tongue into her little hole, I ate it out like it was her cunt, I licked my fingers and pushed one into her arsehole and felt her sphincter relax and open, I followed it with another finger and then a third and forced her ringpiece open. Noel already had four fingers in Mums arsehole.

Noel grabbed a bottle of lube and lubed my cock up for me and positioned the tip of my cock just at the entrance to my sister's arse.

"Right mate, fuck your sisters arse" Jake told me and he held onto my cock and he pushed my buttocks forward and my cock slid into my sisters arsehole till it was up to my balls. My sister waggled her arse to get comfortable and sighed.

I heard a muffled scream and a grunt, Noel had given Mum the full length of his cock in one thrust up her arsehole and was now banging away hard, Mums legs were twitching and I could see her tits flapping as Noel pounded. I took the hint and fucked my sister's arse hard. Sis was breathing heavily, I realised that she was working on her clit.

"I need to come Noel" I shouted.

"Don't you dare mate. Pull out" Noel told me, so I did. My cock was jerking to its self and I could feel the spunk rising, I gripped hold of the base of my cock and squeezed hard. My sister's arsehole was open and I could see her pink insides, she moved her hand around and fours fingers went straight in.

Noel was still arse fucking Mum, not missing a beat he said, "the client decides where she wants your load not you. Some of them want it in their cunt or arsehole but most want to see you spray over their fanny, tits or face" Mum grunted as he thrust hard into her arse. He carried on saying, "if the clients husband or partner is there watching or joining in he'll want to see you glaze her face, he thinks that he's got his monies worth then."

I nodded and thought hurry up Noel I want to come.

Noel continued "you can shoot from a distance or hold her head and unload over it, if she's got her mouth open than that means its OK to fill her mouth with your jizz"

Well, you learn something new everyday!!

"OK then mate, over your sisters face and I'm going to fill your Mothers mouth" Noel told me.

The girls heard and flipped over, I heard the "plop" noise and Noels cock emerged from my Mums arsehole.

"Give me your spunk little brother" said Jo, so I did, I only needed a few strokes with my hand on the shaft of my cock and I fired off, I thought that I was never going to stop spunking, six good squirts followed by a few dribbles. Jo was covered in her brothers cum. She did her best to swallow and wipe it off of her face with her fingers but it still dripped all over her tits and fanny.

I heard Mum cough and watched Noel push his cock into my Mothers mouth and I could see it throbbing as he churned out his load into Mums mouth. He pulled out and flicked a few drops over her face.

"Show me" he demanded. Mum opened her mouth; I could see that it was full of white creamy cum. "Swallow" Noel told her. So she did. I was watching my Mother eat a mans spunk.

Noel gave me a high five, "you did well for your first time, its not like sex with a girlfriend is it Simon"

"Defiantly better" I said, "I need a shower" and started to walk away.

"Oh, where do you think you're going you've got two women in front of you, you've spunked up but they haven't cum yet have you girls" asked Noel.

Mum and Sis shook their heads.

"You've got to give the clients their monies worth and make them come at least once during the session so lets do it" Noel laughed.

"But I don't think that my cock has got anything left in it Noel" I said as I looked down at my battered and red cock that was just hanging there.

"Well you've lost your tip then haven't you" said Noel. "Lucky these two aren't paying for your cock or they'd want a refund. You know what to do girls" Noel told Mum and Sis.

They sat on the sofa with their arses over the edge, flipped back and open their legs to expose their well-fucked cunts. Mums was big and open, Sis's was red and bloated.... both needed finishing off. Noel and I sat down on the floor between their legs.

"Fist your Mothers cunt Simon, she loves it while I see how many fingers I can get in your sisters hole" Noel told me.

Fist? He wanted me to put my fist in my Mothers fanny. I knew what he meant, thank God for porn.

Mum held her fanny lips apart and said "finish me off, fist Mummy's cunt son."

I put all my fingers together, pointed them at her cunt hole and pushed. She groaned and I watched as her hole opened up and took all my fingers up to my knuckles, I pushed harder and my hand disappeared into her cunt up to my wrist, I stared to fuck her, pushing my fist in and out, her grunts changed to moans that changed to screams, "fist me, fist me" she screamed. Mums big swollen clit was getting stimmed as I pushed in and out.

Sister was panting, "I want to take it, push it in Noel" Jo said. Noel had his fingers in my sister's fanny up to his knuckles and was fucking her. His thumb was rubbing on her clit.

Mum started to twitch, I felt her hole tighten on my wrist and her body convulsed. I pulled my hand out just in time as she convulsed and orgasmed. She squirted a load of fanny juice at my face and then pissed herself, I saw her little piss hole open, pissing all over me, I could taste it.

Sis came but Noel kept his fingers in her gash so the fanny juice leaked out around his hand. She didn't wet herself.

It went quiet, apart from the sound of Mum and Sis panting.

"Sorry, I forgot to warn you that your Mums a great pisser when she's fisted to a climax, think its an age thing. You OK with piss?" Noel asked.

I'd never had anybody piss on me, not even during the rugby club after match games but I realised that I loved the smell, the heat and the taste of piss.

Mum and Sis just lay there, at least they closed their legs with stupid grins on their faces...they looked well fucked.

"I'm off home" said Noel, "the boy will be waiting. I'll see you at work in the morning and you can let me know your decision. If it's a yes I'll organise with the Doctor to give you a full sexual heath check before I let your cock anywhere near a client. You did well mate. Night" and Noel headed home.

I sat down between Mum and Sis. They both looked at me and said "well?"

"Yes, defiantly, more than anything that I've ever wanted to do" I answered.

"Great, I can tell that you want to, look at your cock," laughed Mum.

My cock was hard again.

"We're going to have to train you, hard work and homework every night" said Sis.

"Oh and Simon" said Mum.

"Yes Mum" I asked.

"Take your fingers out of my cunt, its had enough tonight" Mum laughed.

"Sorry Mum, I'm just getting in some practice!!" I answered.

The next day at work I told Noel that I wanted to go ahead with becoming a male sex worker and become one of his "studs in the stable" as he put it.

"I'm really pleased mate, your a hard worker and with a bit of training you'll be great at your new job. I'll organise a full medical with the Doctor for you. Now you carry on gardening, I've got a fanny to fuck" he told me as he wandered off into the house, kicking off his shorts as he walked. I noticed that he had a small lion tattoo on each buttock.

If I wasn't working in the evening or during the day and my Mum or sister were at home they put me into training, it was like being back at school even to the point that if I got it wrong I was punished.

I liked it when Mum taught me about how to please women, as she said I was there for the client's pleasure, not mine. Mum would teach me and then I was allowed to try everything that I learnt on my sister.

Mum showed me how to work on a women's tits, not just grab, pinch and suck but how to hole, caress, tease with my fingers and mouth, how to suck and tweak, how to increase suction till she would moan. Mum was happy to sit on the sofa with her legs wide open exposing her fanny and to teach me about all the parts of it. The outer lips, the inner lips, the clit and its hood, her piss hole - I loved to see her piss out of it - and of course the vagina itself, or as I called it, her fuckhole. I loved to open it up and see the pink moist flesh, and to think that I came out of that hole all those years ago and now my fingers and cock were going back into it.

I loved a women's arse, well to be correct I loved my Mums arsehole. The pink pucker, her starfish, her arsehole. I learnt to lick it, get the tip of my tongue into it, taste it, the taste of sweat and the taste of a woman. Work on it enough and it would relax and open and allow my finger into it. My Mum loved her arse played with and fucked, apparently she was known for what she could take up it and was in great demand. But that will be another story.

When she was ready I would be allowed to push my hard cock in there, I loved the tightness and the warmth of her arse.

In my keenness and lust, that's when I got punished. I tried putting too many fingers in my Mums arsehole before she was fully relaxed, she pulled away and screamed, "you stupid boy, you could have hurt me, don't you ever do that again to any women, always respect what a women wants, its not about you."

"Yes Mum, sorry," I answered.

"If you're going to be a stupid boy then I'm going to have to punish you so you learn" Mum said.

"Bend over the chair and present your arse to me" She demanded.

I did as I was told; I knew that even at 20 years old it was better to do what my Mum told me to.

"See this" Mum showed me a riding crop; I knew what it was all about as the rugby coach had used one, just jokingly, on our arses when he thought that we weren't training hard enough. "I use this on some of my naughty boy clients, didn't think that I'd have to use it on my son. Pull your pants down so I can see your arse."

I shrugged my tight boxers off, I was hard and my cock was leaking just at the thought of what was about to happen. Mum noticed the cum stains and the state of my cock and exclaimed "you dirty little boy, you wont be hard when I've finished with you."

I heard the swish and my arse exploded as the crop made contact with my buttocks, I wanted to scream but wasn't going to give Mum the pleasure of that. Mum wasn't holding back, my arse was on fire, as she gave me another five strokes of the crop across my arse, I could feel that it was glowing red and that welts were starting to form. Six strokes in all.

She was right, my cock had gone soft and it looked like it was trying to hide in case it was on the receiving end of the crop.

"One more Simon. Pull your arse cheeks apart so I can see your pucker" Mum said.

She wasn't going to hit that was she; before I had time to think she bought the leather piece on the end of the crop down across my arsehole...hard. I screamed and fell forward, I could feel the tears forming in my eyes....why had Mum done that to me? The problem was I was enjoying, in a strange way, getting punished by my Mother.

"Your holes going to sting for a few days so you'll remember what happens when you get things wrong. Now come and sit on my lap, you can play with Mums fanny and suck on Mummy's nipples."

I did, I was Mummies little boy again.

The next day at work Noel asked what was wrong. Should I tell him?

"Mum punished me, it still hurts," I told him.

He laughed and said "don't worry, she did the same to me when I over stepped the mark, and I'm older that you. Punishment and taking things up her arse are her specialities. Drop you pants, lets have a look"

Noels son, the boy as he was known, wandered over to have a look as well. I'd long stopped being embarrassed by showing my bits off to other men, well, if I was going to work in the sex industry you can't really be embarrassed can you?

"Nice, you've got six crop marks across each or your arsecheeks" said Noel, I felt Noels son touch my arsecheeks and whistle.

"Open up your cheeks and show me your hole" Noel said, so I did.

"Ouch, I bet that stings, I think you've got a bruise coming" Noel laughed.

"It bloody stings when I have a shit I know that" I said and we all laughed.

"By the way, your sexual health check with the Doctor is at the next week so I hope it all heals up by then, but then the Doctor has seen and done worse" Noel looked at me and smiled.

A few days later, my pucker and arse had returned to normal, I came in from work and only Jo; my sister was in the house.

"Mums out on a job but she's left me instructions" she said.

That sounded ominous.

"Get your arse upstairs into Mums bathroom and strip off" she told me. Now what was going to happen?

I hadn't been into Mums bedroom in years, as a family and the me being the only man in the house and spending all my time working or at the gym or at rugby during the season I kept out of the way of the women and what they got up to, although I now knew what they got up to, selling their bodies.

Our house, in its day, had been in a nice area although the area had slipped, and was a four bedroom house, two on suite bathrooms for the ladies and I had the family bathroom next to my bedroom so we could all have a bit of privacy and stay out of the way, looking back some evenings it could be total chaos in the house when Mum and sister were trying to get ready to go out whoring.

"Get undressed little brother" Jo said. Even stripping off for my sister didn't bother me now. A few weeks ago I wouldn't even have let her see me in my underwear and now look!!

I was soon naked.

"You stink, I can smell your cock from here" sister exclaimed.

It was bit ripe; even I could smell piss, sweat and smeg. "I've been grafting all day so I'm not going to smell of roses am I?" I told her.

She stood in front of me and pulled back my foreskin, it was sticky. "You're lucky I don't use a nailbrush on it, some of my clients would enjoy that" she laughed. I pulled away quickly just in case she did.

"Go into your own lads bathroom and have a shit and a shower as you rugby boys call it, come back here when your ready" Jo said and I picked up my clothes and scurried off, she slapped my arse as I went past her.

Ten minutes later I reported for duty with a towel around my waist and said "all clean, fresh and sparkly."

She pulled my towel off, dropped to her knees, skinned me back and said "that will do" as she took my cock in her mouth. She didn't suck it, just let it rest in her mouth, the warmth of her mouth soon meant that my cock was standing to attention.

"Mum and I take a lot of fingers, cocks and toys up our arseholes so we always have to be washed out and clean and if you want to sit on a women's face and let her eat your hole out or want her to finger it then you've got to be clean and just washing your pucker is not enough. Who knows, eventually you might take toys or even cock up there" Sis said.

"No way, I'm straight, don't mind touching cock but that's it" I told my sister.

"We'll see, I mind remind you of what you said in a few months time" she laughed.

"So I'm going to teach you how to wash your arse out, how to douche your hole" Jo said.

I wasn't sure about this but I was intrigued.

"Mum and I do a deeper was out or enema, you only need to douche so you don't need too much water in your arse, just a couple of pints a few times." she unclipped a hose with a thin nozzle attachment that was in Mums shower. "I'm going to lube your arsehole then this is going in there, don't worry its only a small one the size of a finger, you wait till you have to have an enema and see the size of that nozzle" she laughed.

I just went with the flow; whatever I did it was going to happen.

"Bend over brother" she told me and I felt her push a lubed up finger into my hole, it went in easily. "See that's wasn't hard was it" Jo said, that wasn't hard but my cock was.

She turned the water on till it was running warn and was a trickle, I don't know why but I expected it to be a water jet...that wasn't going to happen until I worked at "The Club." I felt my sister push the nozzle into my arsehole, it wasn't painful, just it seemed strange something going into my hole rather than coming out!! I could feel the water running in, I could feel the pressure building up and I could see that my cock was jerking and leaking precum.

"That's enough, you know what to do, push the water out Simon" said Jo and she pulled the plug out. I tried to hold the water in, I was embarrassed in front of my sister, "just do it, when you're used to it you can do it in the privacy of your own bathroom, I bet your rugby boys do far worse than this on tour?" She was right, so I let it all go.

"Good lad, lets fill you up again," Jo laughed.

Two more flushes and my sister was happy with the result even if I'm not sure I was, my arse felt sore. "Oh stop complaining, you'll get used to it so here's your own nozzle for your bathroom shower."

"I'm not doing that again," I said.

"It goes with the job Simon so get used to it, it looks like your cock enjoyed it anyway."

My cock was rock hard and oozing fluid.

"Put it in your sisters cunt big boy" Jo demanded, so I did. I fucked my sister in my Mums bathroom, pounding her hard, she was squealing, especially when I pinched her clit a bit too hard. She pushed me away from her and my cock sprung out of her fanny, she checked out her clit and said "no permanent damage done, bend over and spread your legs" and I saw her pick up the lube bottle.

She pushed two fingers into my arsehole and found my prostate, she was an expert fingering it, she knew she was in the right spot as I let out a yelp, followed by a moan. Her other hand went between my legs and grabbed hold of my cock and wanked me, it didn't take long, manual stimulation of my cock and prostate produced a huge stream of pent up spunk to fire out from my cock across Mums bathroom floor. "Well done brother," Jo laughed as she pulled her fingers out of my arsehole. "See, that's why you need a douched out hole. Drop to your knees, its my turn."

I thought that she wanted finishing off and I was going to be allowed to finger her to an orgasm or eat her fanny out till she came. I was wrong. On my knees, looking up at her open fanny she let go a long stream of piss all over my face, the dirty bitch....but it was hot.