Simon Says - My Story Pt. 07

"Lets get the milking machine on your cock and drain your balls" she said to Jake.

She unrolled a sheath over his cock, like a condom and then pushed a clear tube over his cock, it looked just like teat that was pushed onto a cows udders when it was milked.....and that's what it was going to do to Jake, milk him dry. A thin plastic tube from the top of the clear tube was connected to a machine.

The machine started with a whirring noise, you could see the rubber sheath tighten and expand around Jakes cock, the plastic outer tube moved up and down. Jakes cock was getting wanked and sucked at the same time. As the machine sucked the fuck machine pushed the dildo deep into his guts, rubbing his prostate.

Jakes moans increased and his hips started to buck, I stroked his crop-marked arse. The dominatrix grabbed hold of his bruised engorged nipples and squeezed them hard.

The clients watched, the men wanking and the women fingering their cunts.

"That's it Jake, lets get those balls churning, lets get that spunk pumping, give me your load like a good boy should" the Dom said.

Jake thrust his hips forward, screamed out through his gag and I saw his arsehole tighten around the dildo as he shot his load, another six pulse of cum shot out and was sucked away by the machine into a sample pot.

The Dom let the machine carry on its work, sucking and pulsing away and said "come on Jake, one more shot, show me what you've got" and she brought the riding crop down across his balls.

The scream was followed by another shot of spunk from Jake. Jake was finished, running on empty, as his cock went soft the milking machine sheath fell off of his cock. His cock was red and bruised.

I removed the fucking machine from his well-fucked arse. His hole was open and red, it looked sore. One of the clients came around to inspect and she pushed four fingers deep into his hole. Jake was past caring and just stayed still.

"Well done Jake, a good load, you've earned your money today" said Doctor Moore.

He removed Jakes gag.

We all heard Jake say "thank you Sir."

The security men released Jake and helped him from the room.

"Ladies and Gentlemen, drinks and food is available and then if you want to watch the next performance, you know what it is, you'll be escorted to the room" said the Doctor making it sound like an interval in a play.

"Simon, you need to go and get ready, get your shot and meet your fellow performer," I was told.

I walked back into the medical room, my cock was still hard and plugged and my arse still had a butt plug up there. Sitting on one of the examination tables was another man, naked, about the same age as me.

'Hey there" I said " I'm Simon."

He stood up and said "I'm Craig."

We didn't know whether to shake hands or not, I suppose that we could have grabbed hold of each other's cocks and shake those, might have been more appropriate!!

We checked each other out. He was buff and muscled, gym trained, not by hard work. Same height as me, he'd clipered his chest hair, he looked after his appearance, had a smart haircut. His cock was soft, hanging nicely over a set of waxed balls and his pubes were trimmed to a two-inch square of hair above the shaft of his cock. His cock was probably the same size as mine when hard but thicker and he had a big loose foreskin hanging below the head of his cock.

"You been working already?" Craig asked, he pointed at my still hard cock.

"Not really, just been helping out, been getting Jake to produce a big load," I said, not really thinking.

He looked at me and asked "Jake, lad about our age, fit?"

I nodded.

"Jake Moss" he asked.

I nodded again.

"Well the dirty little fucker, he kept quiet about coming to The Club" laughed Craig. "He didn't tell me and I'm one of his best mates."

I laughed and said, "well I bet he doesn't know that you work here either, I'd love to be watching when you two both meet up here."

We had a chat. Craig was working here full time and raking the money in, a fresh bit of cock or cunt always does. He'd started off selling spunk and piss stained underwear on the Internet, then done a bit of gay escort work and then moved onto straight escort work. One of his female clients had taken a fancy to him and decided to help him out in his "career" and introduced him to Doctor Moore.

"So after a very strange, painful and spunk producing medical I'm working here and earning great money and as I'm happy to see men or women I'm proving popular," Craig said.

As we were talking he'd been playing with his cock that was now nearly fully hard. He had a really big and open piss slit, reckon you could get the tip of your finger in there.

With that the Doctor and the medic walked in, Doctor Moore said, "I see you've met. You did well today Simon, decent tip coming your way. Your balls must be desperate to spunk." I nodded. "Lets get your sperm stopper and butt plug out."

The medic held my cock and the Doctor pulled the sperm stopper out of my piss tube in one pull, I yelped and squirmed. Precum flooded out. I turned around and he eased the butt plug out of my arsehole, I could feel it was open. I went to straighten up and the Doctor said, "stay where you are."

I looked over my shoulder and saw the Doctor open his white lab coat and skin back his hard cock, then in one push he was up my arse, up to his balls and he pounded away. Craig watched and smiled.

"Spunk time Simon" the Doctor said and fired his load deep into my arsehole. I knew that I wasn't allowed to wank or cum. He pulled out his cock with spunk still dripping from it, turned around to Craig and said, "clean it." I looked at Craig and wondered if he would, Craig dropped to his knees and took the Doctors spunk covered dick in his mouth and sucked and licked it clean.

"Good to see that neither of you have any hang-ups with being bi" the Doctor said. "Best of both worlds, cunt and cock." he laughed.

"Lets give you both the Caverject shots to keep you hard for the next few hours and then we'll get you ready for the clients" he said.

The medic approached with two hypodermics. Injections don't bother me but having a needle pushed into your hard cock makes your eyes water. The Doctor held my cock and pushed the needle into the underside of my cockshaft, one shot one side and one shot on the other side. As he injected Craig I heard him say "fuck, that hurts."

We now both had rock hard cocks.

Twenty minutes later Craig and I were standing at long urinal in a toilet that looked like a school toilet. We were dressed up as college boys; we're defiantly over 18 years old so I suppose that we were mature college boys, more college men. Craig and I were identically dressed. Short sleeved white shirt with a college tie, the shirts were tight, showing off our muscled bodies. We were also wearing tight grey tailored shorts; they showed off our muscled arses and just about contained our hard cocks that were clearly outlined. Underneath we had on tight white briefs. To finish the uniform we had long grey socks that finished just below the knee and black uniform shoes. We could have passed as college boys although as we were showing off our cock bulges I think we might have been asked to leave he college!!

We knew what we had to do.

We unzipped our shorts flies and fished our hard cocks out, pulled back our foreskins and, after a bit of straining, we both started to piss, aiming our streams of piss up the back wall of the piss trough. You could hear the strong streams of yellow piss hit the steel trough.

We knew that we were being watched and this was being live streamed to some of the clients at The Club. We both undid the belts on our shorts and let them drop to the floor and then slide our white briefs down to our knees to show off our arses and hard cocks.

Craig turned around, aimed his cock at me and pissed soaking my cock in his piss. My underpants got covered and so did my cock.

"You dirty fucker, I'm covered in piss," I shouted so aimed my piss dripping cock at his cock and pissed all over him as well.

We put on a good show, pissing over each other, soaking our underwear in piss; we even started "sword fighting" with our dicks. It bloody well hurts getting a hard cock slapped against your hard cock.

There was a bang on the door and a mans voice said, "what's going on in there?" and Doctor Moore walked in, I was tempted to piss over him but my arse would never recover from the punishment it would receive. "You dirty boys, this is a toilet not a playground, I'm putting you in detention and calling your parents. Come with me" and he grabbed hold of our hard cocks and pulled us out of the toilets with our underpants and shorts still around our ankles.

We were taken into a classroom. It had a blackboard on the wall, a big desk at the front and a row of small desks, just like a college classroom. We managed to squeeze behind two of them.

The door of the classroom opened and the "teacher" walked in.

She was fit, very fit. About 35 years old, tall, blonde hair pulled into a school teacher bun, slim, big tits squeezed into a half cup bra covered, just, by a white blouse, a great looking arse with a short black skirt, black stockings and black high heels. She knew how to dress to impress and create hard cocks in her pupils. She was a college boy's wetdream!!

She was the wife of a much older man, both were clients of The Club. He was the owner of a large family firm in the area and they were both well known. He preferred, sexually, to be dressed up as an adult baby and be used and mothered by older women whereas his wife preferred younger men. They were both regulars at The Club and always played separately but always watched each other fucking or getting fucked so her husband was probably watching this scenario play out.

"Good Afternoon, I'm Miss Price" she said "and stand up when a teacher enters the room."

We both stood up, she couldn't help but notice the bulge in our shorts, especially as Craig rubbed his through his shorts.

"Typical boys" Miss Price said. "Now you know what you're here for, detention, after being caught in the toilets playing around with your penis and urinating over each other. I can smell you from here. So if you behave and do what I ask you to do the sooner you can both get out of here and get changed into clean underwear and shorts. Sit down and get on with your work."

She turned around to face the blackboard and bent over to pick up the board rubber. Her short skirt rode up showing off her black stocking and matching suspenders and a tiny pair of lacy black knickers barely covering her arsehole. She knew what she was doing.

I hadn't come all day and so was desperate to unload, I was tempted to leap over the desk, grab hold of her and ram my very stiff cock up her arsehole and fuck her till I spunked. I knew better than to do that as the client always comes first.

"Get on with your work" she said as she stood up pulling her skirt down to cover her panties.

Craig had undone he shorts and pulled them down enough so that his hard cockhead was sticking out from his underpants waistband. He put his hand up and said "Miss Price, I don't understand this sentence in the textbook."

She walked across and bent over Craig's desk looking at his textbook, her arse was facing me, almost positioned right in my face. I couldn't resist it so ran my hand up her leg until it reached her crotch. She didn't resist or push my hand away, she just spread her legs open wider so I had easier access.

She suddenly stood up, closing her legs and trapping my hand, she shouted out "is that your penis I can see, have you got your penis out in my classroom?"

She grabbed hold of Craig by the hair and almost dragged him to the front of the classroom; I just managed to get my trapped hand out of the way.

"You dirty little boy, you have got your penis out. Stand still and put your hands on your head" she shouted. As he did as he was told his shorts slid down to the floor.

My cock was getting even harder, especially after feeling her crotch, her skimpy knickers were wet, so undid the belt of my shorts, unzipped my flies and pushed my shorts down and pulled the front of my underpants down and pushed them under my pumped up balls. My cock was free but Miss Price didn't notice, she was too busy with Craig.

She picked up a cane from off of the desk and said, "I don't want to do this but you have to be taught not to play with your penis in class" and with that she brought the cane, expertly, down across Craig cockhead that was sticking out from the waistband of his underpants.

Craig screamed and I winced, a slap across the cockhead is bloody painful but Craig straightened up still with his hands on his head. "Do you want another one?" she said.

"No Miss, I'm sorry Miss" Craig said.

"Stand there, don't move or touch your penis" she said and moved across to me, I didn't have a chance to get my cock back inside my underpants and pull up my shorts so she caught me. "You're playing with your penis as well, what is it with you college boys, always playing with yourselves."

She grabbed hold of my cock and dragged me out from behind the desk to the front of the classroom; I had to shuffle as my shorts were around my ankles. My cock was standing to attention with my underpants underneath my balls and Craig's cockhead was still trapped by the waistband of his underpants.

Miss Price looked us both up and down and said, "as you both love showing and playing with your little penises you better strip off your shorts and underwear and show them off."

Craig and I ended up standing at the front of the classroom wearing our white shirts, long grey socks and our black shoes with our cocks, balls and arses on show. "Miss" just stood there and smiled.

There was a knock on the door and Doctor Moore walked in. He looked at both of us standing there with our cocks on show and nodded and said "Miss Price, I contacted Simons Mother as you asked and she's waiting outside. Shall I show her in?"

"Yes please Doctor, I'm sure she'll be interested is seeing what her son and his friend has been up to in detention." she said.

The Doctor left and my Mother, yes my actual Mother walked in to the room. She hadn't told me that she was working at "The Club" today, let alone involved with this scenario. Mum was dressed how you see those American soccer Moms on the porn DVD's just before the Mom gets banged by the coach and the team, she was all class.

Tight leggings, you could see she wasn't wearing any knickers under them as you could see her fanny lips and a tight top that showed off her hard nipples, so no bra, she could get away with it despite being an older women. I could see Craig looking wondering if it was my Mum.

"Miss Price, I'm Simons Mum, I'm so sorry about this but you know what 18 year old boys are like, hard cocks all the time" Mum said.

"Well I understand his hormones are raging but he should learn to keep his penis in his pants and not encourage his friends to behave the same and think that it's OK" Miss Price said.

"Well he's like this at home, always walking around in just his underwear with his hard cock showing, his sheets on his bed and his underwear are always stained and sticky with spunk, he's always wanking, but that's boys for you. You've got to admit that he has got a great cock and balls, just the thought of it makes me wet...look," said Mum

Mum pulled her leggings tight and you could see that her crotch was wet, her fanny was leaking. She then stood between Craig and I and grabbed hold of our hard cocks pulling our foreskins back.

"Mrs. Scott, that's not appropriate behavior either, now I know where your son gets it from" the teacher said.

"Oh come on Miss Price, I bet it gets you wet, all these 18 year old men walking around in their tight shorts showing off their bulges, you imagining how big their cocks are and what they'd feel like in your cunt. Bet you're wet now aren't you?" said Mum.

"Mrs. Scott, I'm certainly not wet and don't have those thoughts" Miss Price said.

"Oh I know that you're wet, I could smell it as soon as I walked into the classroom. Lets have a look" said Mum and walked across to Miss Price pushing her against the teacher's table.

Mum dropped to her knees, lifted Miss Price's short skirt up, showing off her knickers and pushed her face into the teacher's crotch. Craig and I could hear my Mum sniffing and licking away. Miss Price sighed.

Mum pulled the teachers little knickers down and started to finger the teacher's cunt with two fingers, pulling them out and licking her fingers clean.

Mum stood up and said "told you that you were wet. Craig come here, your teacher needs fucking."

Craig didn't need telling twice. He lifted Miss Price onto the desk and the teacher opened her legs. My Mum held Miss Prices fanny lips open and pointed at the teachers clit, "I'm going to rub your teachers clit to stimulate her till she's desperate for your cock, when her hole opens put your cock in her and fuck her" said Mum.

Craig nodded and walked forward so that his cock was in line with the teacher's fanny. Mum started to rub and pinch Miss Price's clit, I was standing there watching, I could hear Miss Price moaning and saying, "no, stop, its wrong" but made no attempt to push my Mother away. Mum started to stim her harder, the teacher was panting and her fanny was starting to get very wet and her fuckhole was slowly opening up as if asking for cock. As the teacher started to lift her arse off of the desk Mum said to Craig "now, get your cock in her cunt, fuck your teacher hard, she wants your cock."

Craig entered into Miss Price hard and in one stroke, right up to his balls. His cock was a decent size but it was the thickness of his cock that did the damage and stretched Miss Price's cunt open, she moaned and muttered "fuck me, fuck me hard, I need young mans cock." Miss Price was a cock slut.

Craig pounded away and I stood there like a spare prick.

"Mum, what about me?" I whined.

"Well as you're a good boy, come and fuck your Mum," she said. Mum pulled off her leggings, climbed onto the teacher's desk, laid on her back and opened her legs wide, her fanny was always open and she was very wet. I pushed my cock into her cunt and started to fuck my Mum. The classroom smelt of sex and echoed to the sound of two older women getting fucked by two young men. All you could hear was the slapping of our balls as we went in deep and our balls slapped against their fannies, and the sound of the women on the end of our cocks panting and moaning.

Fucking, panting, groaning, we were in our element when Mum said to Miss Price "time for my sons cock up your arsehole Miss Price." Craig pulled out, rock hard and his cock covered in the teacher's fanny juice.

"No" said the teacher, "I've only ever had a dildo or fingers in my arse, I've never had anal sex before."

"Well it looks like your students are going to teach the teacher something then" said my Mum. "Don't worry Simon is an expert arse fucker."

Craig and I flipped Miss Price over so she was bent over the desk. Mum handed me a bottle of lube, well every classroom has lube instead of chalk doesn't it? I coated my hard cock with a generous dollop and pushed a lubed up finger into the arse that had been presented to me. I pushed my finger through her pucker and she jumped. I pulled my finger out and pushed two fingers deep inside her, she moaned and tried to stand up and said, "no, you mustn't, I won't let you, it's disgusting."

I pushed her back down and said "Craig, hold Miss down and put something in her mouth to shut her up before she starts moaning or screaming." Craig held her head down as when she opened her mouth he pushed his cock in up to his balls. She started to splutter but Craig nodded as if to say, "she's sucking cock."