Incest/Taboo My First Visit but Not My Last

I was still chewing on the teachers nipples, and she moaned every time I bit down on them hard. The headmaster stood there watching, "that's not good enough girl, try harder when you suck cock," he told Jane and pushed her head down on my cock so she took the full length into her mouth and down her throat, she coughed and spluttered and I felt her throat muscles spasming on my cock, she was gagging and put her hands on my thighs trying to push herself off of my cock but the headmaster held her head so she couldn't. The headmaster laughed and told her to breathe through her nose and her gagging subsided, I have to admit that every time she gaggged it felt amazing on my cock. I decided to be the gentleman and pulled my cock out of her mouth, she spluttered, and the drool ran out of her mouth, my cock glistened with her saliva, Jane took a deep breath and leant back on her knees breathing deeply but with her mouth open waiting for cock.

I held her head, the headmaster nodded, and I face fucked Jane, ramming my cock in up to my balls and holding it there as she massaged the shaft of my cock with her throat muscles and when she gagged I pulled out, my cock glistening with her throat gunk, when she got her breath back I rammed back into her mouth, again and again using her mouth as just a hole for my pleasure before Jane squeezed my balls as if to say stop. I pulled out, gave the teachers nipples a hard bite, and watched my cock twitch and drip a mixture of my precum and Janes saliva.

"Good lad," said the headmaster, "I think you deserve a fuck for that," he turned to Jane who was still on her knees, "get up and get in position, help Miss Bishop onto the desk," he told her. She jumped up and helped the teacher onto the desk, she lay on her back, spread her legs open wide and lifted them up by hooking her hands underneath her knees so that her well used and open fanny opened up on display. Jane bent over and pushed her head between Miss Bishops open legs, the teachers fanny was hanging open, Miss Bishops pulled her legs back a bit more to show off her arsehole, it looked in better condition than her cunt, Jane pushed two fingers into the teachers arsehole and used them to stretch the ring piece open and started to lick and probe the hole, slurping away happily, I heard Miss Bishop say, "Good girl, eat my arsehole out," and she did, I could hear her snuffling and grunting as she used her fingers and tongue to stretch and eat the hole.

I looked at Janes arse, I could see her hairless slit and her arsehole, it looked tight, I wanted to fuck her fanny and arse, I didn't even flinch when the headmaster grabbed my cock as since visiting The Club I'd got used to other men's cocks, arseholes or other men handling my cock and arsehole, he said, "No need for lube, plenty of saliva and precum on it," he then pushed a finger into Janes fanny, pulled it out and licked it before saying, "she's wet enough," and then he shoved his finger into her arsehole, Jane grunted and tried to stand up but he pushed her back down and said, "Concentrate on Miss Bishops arsehole girl," he then turned to me, "her arseholes nice and tight but she'll take cock in there if you stretch her and take it carefully, so its up to you lad, cunt, arse or both," and he slapped my arse as if to encourage me to get on with it.

My cock was hard and ready for use, I tapped my cockhead against her arsehole and she pushed back as if to say yes but I went for her wet fanny, moving down a little, finding her wet hole and pushed the full length of my cock into her cunt, all the way in and then held it there, she took it all and used her cunt muscles to milk my cock, gripping it and then relaxing so I pulled all the way out of her hole, my cock was coated in her juices and I rammed back into her and fucked her, short hard thrusts, long slow thrusts and each time I bottomed out in her cunt she'd grunt, a muffled grunt as her face was in the teachers arsehole.

With one hard deep thrust I pulled out and lined up my wet cock with her arsehole, she knew what was coming and relaxed her ring piece as I pushed just the head of my cock into her, I felt her ring piece open up and my cock head glan pop through, I held my cock there and just rocked backwards and forwards. As I was about to gently push my cock in further the headmaster slapped my arse cheek hard with his hand right across the cane marks, I yelled and reared forward pushing the full length of my cock all the way into Janes arse in one go, she screamed but took my cock, she didn't have a lot of choice as I was already deep in her, she pulled her face out of the teachers arsehole as if to say something but the headmaster just pushed her face back down, this time, into the teachers sloppy fanny.

"Go on then lad, fuck her arse," the headmaster said and slapped my arse again. I pulled all the way out and looked down as my cockhead popped out of her ring piece which stayed open nicely to allow me to thrust back in again, full length in one thrust and that's how I carried on, the full length out and then the full length in, now that Jane had opened up, she seemed to be taking my cock with just the odd grunt.

The headmaster walked across to the cupboard, oh fuck I thought, hope he's not going to get another cane and beat my arse but as he opened the cupboard door, I could see that there was shelves full of sex toys, dildos, butt pugs, inflatable plugs, strap on's, gags, you name it then it was there. He picked up a large conical black butt plug with a wide base, the plug must have been six inches in diameter at the base and about an inch diameter at the top of the cone, probably about eight inches long, he picked up a bottle of lube and walked across to where I was fucking arse. Was I going to get the plug shoved up my arse? I don't think that I was ready for something that big yet, I wanted to be able to walk the next day.

The headmaster pulled a high stool out from underneath the desk and slapped the base of the butt plug down on the top of it, the base acted as a suction cup and the plug stuck to the seat, the plug wobbled and twitched obscenely. I got another slap on my arse from the headmaster who said, "OK lad, pull out of her arse and help me plug her," I reluctantly withdrew my leaking cock from her well fucked arsehole, she stood up, her face was covered with fanny juice from Miss Bishop whose cunt hung open showing off her pink insides. I put one arm under her armpit and the other arm behind her knee and the headmaster did the same and we lifted her up, so she was in a sitting position, she looked at the quivering butt plug and knew what was going to happen next.

We positioned her open arsehole pucker over the tip of the lubed up butt plug and started to lower her down, she took the first inch or so easily but then started to moan as we lowered her down further and the cone opened her arsehole up more, when she'd taken about half of the plug in her hole she grunted, "I can't take anymore."

The headmaster just laughed at her, "oh you can and you will, your sister was a slut and could take it and as it seems to run in the family being a slut you're going to take the plug up your arse even if it does hurt," he told her and we lowered her down further until there was only about two inches of the plug still to go in and Jane was standing on her tip toes and we let her go. Her face was red, and she was moaning knowing that she couldn't stay on the tips of her toes much longer and that the widest part of the plug would be going into her arse.

The headmaster and I stood back and watched her straining to stop the last part of the arse plug stretching her arse wide open and her legs shook before she had to give up and with a yell, she fell onto the last few inches of the butt plug and it penetrated her arsehole, she screwed her face up and panted with the strain of having her arse opened up. Just to be sure she was fully down on the plug the headmaster pushed down on Janes shoulders and she moaned again. He said to me, "Check she's taken all the plug," I nodded and squatted down in front of her and slide my fingers under her arse cheeks, all I could feel was the base of the plug, I pushed two fingers deep into her wet cunt and could feel the hard latex butt plug through her cunt wall, I gently rubbed her clit just to take the pain of her stretched arsehole away.

"At least I know where you are and won't be able to sneak out of detention," the headmaster laughed.

There was a cough and a voice said, "Headmaster, when you're ready I need a hand," it was Miss Bishop who was still flat on her back showing off her wet arsehole and open fanny.

"Oh, I'm sorry Miss Bishop, come on lad," he said, "lets sort Miss Bishop out," I hope that he didn't think I was going to fuck her, my cock is a decent size, bigger than most, but it wouldn't touch the sides of her wrecked cunt. The headmaster looked at me, "don't worry lad we'll need something bigger than your cock to satisfy her, get a couple of fingers in her, she's wet and open," he said.

I squatted down in front of her cunt, the headmaster stood behind Miss Bishop and held her legs wide open, and I pushed two fingers into her, she was very wet and warm, there was no resistance, so I pulled out and pushed four fingers in, she was still loose. I looked at the headmaster who nodded and said, "Fist her, she can take it, form your fingers into a point and tuck your thumb into your palm and push your way in, Miss Bishop will open up for you," so I did, I pushed into her cunt with my hand and with a grunt from her my hand disappeared into her, I was getting to fist a cunt at last so I carried on pushing and my hand went in as far as my wrist, I held it there and the headmaster said, "Open your hand and form it into a fist inside her," I did and she trembled as if she knew what was coming next, I had my fist in her cunt, "now pull out and then push back in, keep pushing, she'll take it."

I pulled out, my fist was lubricated with her fanny juice, her cunt stayed open, and the headmaster nodded so I pushed my fist back in, pushing harder as I went past my wrist and her cunt swallowed my hand and forearm till, I was nearly up to my elbow in her. She was panting but took it and the headmaster said, "Good lad it feels nice inside your teacher, doesn't it?" he was right, it was warm, my arm was being squeezed by her cunt muscles that she relaxed and tensed, "so now you need to pull all the way out and then punch all the way back in, don't worry her cunt can take it, she's had bigger things up there before, go as deep as you can lad, you'll know when to stop."

My cock was dripping, I heard a moan from Jane who was still impaled on the plug in her arse and who was rubbing her clit as she watched what was happening to Miss Bishop. Miss Bishop coughed as if to tell me to get on with fisting her, I pulled my arm and hand out of her, her hole stayed open and before it had time to close up, I pushed my fist and most of my forearm back into her, hard. She yelled, bucked but took it and tried to hold onto my fist with her cunt muscles but I pulled back out again and started to punch fist her, her fanny slurped and squelched, she moaned and pushed back against me trying to take as much of my fist and arm inside her, As I was a gentleman with my other hand I found her clit, more like a small cock, and wanked her off, sliding my fingers up and down her pink nub.

Her cunt started to spasm around my fist, so I fisted her harder, faster and deeper until I thought that my fist must be in her womb. Miss Bishop screamed, and her cunt exploded as her climax ripped through her, she bucked and tried to close her legs, but the headmaster kept them wide open. She gripped my fist and arm in her cunt as her muscles contracted as more climaxes hit her and I carried on rubbing and milking her clit. I managed to pull my fist out of her, and she almost howled and sprayed me with a mix of fanny juice and piss, her hole stayed open and dripped so I rammed my fist back into her, just up to my wrist and let her climaxing wet fanny squeeze it. I had to put my cock into something or someone, her fanny had my fist inside it so that only left her arsehole empty, so I just pushed my cock into her little pulsing arse pucker.

Her arsehole was surprisingly tight, but my cock was well lubricated with my precum, and Miss Bishops pucker was wet from the tonguing that it had received from Jane and from all the piss and fanny juices that had run out of her cunt and dripped onto her pucker. I fucked Miss Bishops arsehole hard; she was still coming down from her climax so probably couldn't even feel my cock in her but I needed to unload my balls and I wanted to unload them but not up her arsehole so I pulled my cock out of her arse and my fist out of her fanny and turned around, Jane was still sitting on the stool with the plug in her arse but she was lifting her arse off of it till only about half the plug was still in her before letting herself drop back down on it with a sigh, her arsehole must have been gaping, she was also pushing two fingers into her cunt, she needed spunk and I needed to give it to her, my balls were aching with the pent up pressure.

I really wanted to spunk up over her face, but my cock was level with her fanny, I looked at the headmaster and said, "I want to unload over her face sir," he nodded and dragged a wooden box across and pointed at it I and up on it, it was the perfect height as my dripping cock covered in arse juice was in line with Janes face, she smiled.

I wrapped my hand around the shaft of my cock and tried to wank but my cock was covered in precum and arse juice and my hands were still covered in lube and Miss Bishops cunt juice, I need a bit of friction when I wank off, the headmaster looked at me and laughed, "hands behind your back lad," he said, I realised what he was going to do so shook my head and he repeated, "hands behind your back lad, do as I tell you," and before I could do anything he picked up the cane and brought it down hard across my already caned and red arse cheeks. I yelled and nearly fell off the box but that didn't stop him as he caned my arse another three times.

Fuck that hurt, I knew that he'd keep caning me until I did as I was told so I put my hands behind my back and stood there, the headmaster said, "Good lad, I'm going to help you out and masturbate you till you cum, I want a really big load out of you, understand?"

Oh fuck, I really needed to empty my balls, they were aching but letting the headmaster wank me off was going too far but if that was the only way then I was going to have to go for it. When I was an apprentice part of the initiation ceremony for the new lads was to wank off his fellow apprentices so I had had another bloke do it for me and of course since coming to The Club I'd got use to seeing cocks, feeling other cocks against mine when I'd been DP'ing, I'd even been sprayed with other blokes cum so if I wanted to spunk up I was going to have to go with the flow, beggars can't be choosers so I nodded at the headmaster.

He stood to one side of me and held the shaft of my hard cock and slide his hand up and down my cock, sliding over my exposed cock head and then down to my balls. He knew what he was doing, just the right amount of pressure, just at the right speed, he even knew how to twist his fist and he slid up and down, perhaps men know what another man wants whereas some women just grab hold and wank a cock like they're trying to pull it off. With his other hand he cupped my balls and massaged them, I was close, I couldn't take much more of this before I shot my load.

I started to breath hard and let go of the odd grunt, the headmaster said, "He's close, open your mouth girl, you want to shoot lad?" I just moaned before my balls lifted and the first shot of cum fired out of my piss slit and hit Jane right between her eyes, the headmaster carried on wanking me and this time his aim was better, and my second shot of spunk was right into her mouth followed by a third and forth load of my cum. The headmaster carried on wanking me and I carried on spunking up, I'd hadn't shot so much cum since I was eighteen years old, perhaps I needed spanking and pissing on, perhaps I needed to be put in my place, perhaps I was enjoying being a sub?

"Come on lad, there's more in those balls to get rid of yet," the headmaster said as he carried on wanking me, making sure he worked on my sensitive cockhead and I managed two more spurts of cum into Janes mouth, my spunk was starting to drop out of her.

"Enough," I groaned, like most men after I'd shot my load my cock was very sensitive so with one last hard rub of my cock the headmaster stopped but ran his hand up from the bottom of my cock shaft to the head of my cock as if squeezing the last drops of cum up and out of my piss slit. I stood there breathing deeply looking at Jane, her face was dripping in cum and her mouth was full, she swallowed my load, then opened her mouth to show that she had before licking her lips.

I climbed down off of the box and said, "Lets get that plug out of her," and the headmaster and I stood either side of her and lifted her off of the plug that was rammed up her arsehole, she yelped and her arsehole held onto the plug as if it didn't want to be empty but with a squelch and a fart her hole let go and we helped her walk, almost bow legged, across to the desk that Miss Bishop was still laying. Janes arsehole was well fucked and hanging open, but I could see that she was trying to squeeze her ring piece closed, it looked beautiful as it winked at me. Now that I'd emptied my balls and the Caverject was wearing off my cock had started to soften, I needed to piss badly and now my cock was going soft it meant I could.

I grunted and let go a jet of piss high into the air letting it splatter down over Miss Bishop and Jane, I was getting my own back for them pissing on me. I held back my piss and pushed my cock into Janes open arsehole and carried on pissing, she sighed as she felt my hot liquid jet into and fill up her arse and I had a lot of piss. The headmaster cheered and picked up the big butt plug that had been up her arsehole earlier and threw it at me, I caught it and pulled my cock that was still pumping out piss out of her arse and shouted, "Keep it in girl," and shoved the butt plug back into her open arse, she jerked, and her ring piece closed up and gripped the neck of the plug.

I didn't want to piss all over the floor so needed something to contain my urine and I looked at Miss Bishops gaping arsehole, even though my cock was soft her arsehole was nicely open, so I didn't need a hardon to penetrate her, so I pushed my cock in and carried on pissing, filling her arse with piss as well, she managed to grunt saying, "Fill me up lad."

With one last grunt and a clench of my arse muscles to push the last drop of piss out of me I slowly pulled my wet cock out of her arsehole, I said to Miss Bishop, "Close your arse hole up, squeeze that pucker shut," and as my cock emerged from her hole she grunted and with just a few drops of piss leaking out her ring piece closed up.

"Good lad," said the headmaster, "now on your knees and take your own piss."

I shook my head and picked up the cane, "don't think so headmaster, get on your knees and take my piss," he laughed but that changed to a yell when I bought the cane down hard across his arse, even though he had trousers on he felt it especially as I carried on caning him until he dropped to his knees.

He looked at me, "I'll get my own back lad, you won't know what's hit you."

I just smiled and said, "Ready ladies, on the count of three force that piss out of you like when you douche, empty your arses over the headmaster, one, two, three, push," and I yanked the butt plug out of Janes arse to release a jet of high pressure piss and at the same time Miss Bishop opened up her arse pucker and joined in soaking the headmaster with my piss, the ladies knew what to do waving their pissing arseholes so the headmaster got well and truly soaked in piss.

With a few grunts from them both the piss flow ended, their arses were empty, and I watched as the last few drops of my piss dripped from their open arseholes. I nodded at the piss soaked headmaster, pushed his face into Miss Bishops open wet arsehole and said, "Clean her up," he sucked and licked before I pulled him away from the older woman's arse and pushed his face into the younger woman's hole, he did the same to her till her hole was piss free. I dropped the cane and walked away with my now soft cock hanging between my legs. The door opened and Mark walked in, "finished Sir?" he asked, I nodded, "you need a shower, you stink of piss," he continued.

We walked down the corridor, I was naked, to the shower room and Mark stood there, "I'll be back to collect you when you're ready Sir, you have an appointment with the doctor and nurse for a butt plug fitting session, I'm sure that you'll enjoy that," he said with a smile on his face.

The worrying thing is that I probably would.​