Entertaining Miss Assbugger

There is a tiny island in the Caribbean owned by a multi-billionaire and she has had built upon it the ultimate in luxurious hotels in which, if you can afford it, your wildest sexual fantasy will be satisfied.

If you are a woman and your dream is to be gang-banged by Adolf Hitler, Benito Mussolini and Joseph Stalin, well-endowed look-alikes will be sourced, hired, trained, groomed and made up. They will have the perfect mannerisms, accents, moustaches, haircuts, uniforms and, if necessary, weapons. And they will be as gentle with you or as brutal with you as you desire.

And if you want to spice it up a little more you can have Eva Braun join the party, either dressed as a Bavarian beer-cellar serving wench or just stark naked, it's your fantasy.

If you are a man and your fantasy is to be the only man shipwrecked on a desert island with a dozen beautiful, eighteen year old, horny virgins who all have the hots for you, then only the most beautiful, large-breasted, horny, slutty virgins will be provided for you, by the dozen.

If you are a woman and your fantasy is to be the only woman shipwrecked on a desert island with a dozen beautiful, eighteen year old, horny, lesbian virgins who all have hots for you, no problem. Or maybe you'd prefer a dozen eighteen year old, muscle-bound jocks with big cocks. Or both.

Maybe your fantasy is to whip your mother-in-law's scrawny naked butt until it bleeds and she begs you to stop and promises you a blowjob if you do. If so a look-alike painslut will be hired for the job.

I think you get the picture, you can have any scenario you choose, just so long as you can pay for it.

Shortly before noon Jenny, a guest welcomer at the Dreams Come True Hotel, opened the door of a suite of rooms and admitted four eighteen year old young men into the lounge. The lounge was large and luxurious. There were also four bedrooms in the suite, each with its own bathroom.

"Your luggage is already here, gentlemen," she said. She indicated a rather plain-looking woman of about fifty, dressed soberly in woollens and tweeds, standing in the middle of the room, "and this is Miss Gertrude Assbugger, your hated and despised geography teacher.

"She will be your slave for the next twenty-four hours. I do hope she meets your specifications."

"Slave," Jenny addressed Miss Assbugger, "these gentlemen are your masters and you will address them as 'Master' followed by their name, Master Adam, Master Barry, Master Cliff and Master Dan."

"Yes, Mistress. Thank you, Mistress."

"Wow," said Adam, "it's uncanny, she looks exactly like the old battleaxe, now we can have our revenge for all the grief she's given us over the years."

"She could be her identical twin sister," said Cliff, "I don't think the world's ready for two of them."

"I don't know how they could have found such an exact look-alike," said Dan, "it's like they've cloned the evil old witch."

"She's exactly like her," Barry said to Jenny, "can we do anything we like to her? Anything at all?"

"Of course you can, sir," said Jenny, "would you like me to demonstrate."

Four male heads nodded.

Jenny stood with her legs apart and hitched up her skirt, she wasn't wearing any underwear and her vulva was completely hairless and visibly moist. Four male mouths gasped.

"On your knees, Slave," she commanded Miss Assbugger, "and worship my clit with your tongue."

"Yes, Mistress." Miss Assbugger dropped to her knees and energetically licked Jenny's erect clitoris.

"Now worship my clit with your lips, Slave, and don't stop when I come, I'll tell you when to stop."

"Yes, Mistress." Miss Assbugger sucked Jenny's clitoris as four young men looked on in fascination.

Jenny didn't come quietly. "Ayayayayeeeeeeeee," she screamed, as she emptied her bladder all over the face of Miss Assbugger, who was still sucking her clitoris. "Stop sucking now, Slave."

"Yes, Mistress."

"Look at the mess you've made, Slave, you were supposed to swallow all of that piss. Your clothes are soaked. Stand up and take them off now, you filthy slut, and then you will be punished."

"Yes, Mistress. I am sorry I did not catch all of your piss in my mouth, Mistress." Miss Assbugger stood up and took off her jacket, sweater and bra. The young men looked appreciatively at her large firm breasts with their large firm nipples. The swollen nipples betrayed her arousal.

"Get a load of Dirty Gerty's tits, boys," said Dan, "who would have guessed the evil old witch would have such a pair of beauties? And look at those nipples, you could hang your hat and coat on them."

Miss Assbugger took off her tweed skirt, she was not wearing panties and her vulva was as smooth and hairless as Jenny's. She was wearing a black suspender belt, black fishnet stockings and stilettos.

"Stop stripping, Slave," Jenny said. Miss Assbugger stopped stripping. "As you can see, gentlemen, your slave has been plucked and waxed for your convenience and she has a lubed up butt plug inside her to slacken her sphincter for your comfort.

"Would you like her to continue undressing or to stay as she is?"

"She can stay as she is for now," said Cliff, "but let's get down to business, I want my cock sucked."

"Should I suck your cock, sir," asked Jenny, "or will your slave suck it?" She already knew the answer.

"Thanks for the offer, Jenny darling," said Cliff, "and as much as I would prefer your hot young mouth to this wizened old pie-hole, I need to get my revenge on her for all the times she has called me an underachiever. My cock is going to get under her butt and achieve balls-deep penetration."

Cliff took off his trousers and Miss Assbugger's eyes widened when she saw the incredible length and thickness of his erect penis, and so did Jenny's.

"And I want my revenge for all the times she has called me a malingerer," said Barry, "When my cock is inside her butt it'll linger there until she screams for mercy, and then it'll linger longer."

"And for all the times she's called me an illiterate ne'er-do-well," said Adam, "maybe one day I'll find out what that means, if I can be bothered to look it up."

"She's called me a backslider a hundred times in front of the whole class," said Dan, "so I'm going to slide my cock up her back passage a hundred times in front of you guys. That'll wipe the smile off her face"

Adam, Barry and Dan took off their trousers and Miss Assbugger's eyes widened even further and so did Jenny's, Cliff's mighty penis was the smallest of the four. Dan's was the largest.

In front of a large couch was a long, upholstered footstool. Dan lay on his back upon it with his huge erect penis pointing at the ceiling. He reached out and yanked the large butt plug roughly out of Miss Assbugger's backside, causing her to yelp, and tossed it aside.

"Sit on my cock with your back to me, Slave," he said, "and clasp your hands behind your head and pull your elbows back as hard as you can. That should make your tits stick out nicely."

"Yes, Master Dan," replied Miss Assbugger as she painfully inserted the mighty penis into her still gaping sphincter. Ignoring the intense pain, she managed to get the whole length of it inside her.

Despite the lubrication and the stretching of the huge butt plug it was still a very tight fit.

"Now slide up and down on it, Dirty Gerty, and tell us what you saw Miss Lickok do to the janitor and his assistant in the furnace room last January."

"Yes, Master Dan," said Miss Assbugger as she dragged her tortured sphincter repeatedly up and down the full length of his long, fat penis, "I was hiding behind the furnace and I saw Miss Lickok, the students call her Wild Jill Lickok, she was stark naked and on all fours and she was deep-throating the janitor while his assistant's cock was balls-deep in her butt hole."

"And why were you hiding behind the furnace, Slave?" asked Dan as, at the bottom of her stroke, he grabbed Miss Assbugger's impressively large breasts and roughly pulled her back to lie on top of him. "You will now massage my cock with the internal muscles of your butt hole, Dirty Gerty."

"Yes, Master Dan, I will massage your cock with my butt muscles. I was hiding behind the furnace because I was stark naked too and I was taking a rest after being gang-banged by the six guys who crew the garbage truck that comes to the school every Friday to empty the dumpsters. I secretly filmed Wild Jill Lickok and her two guys on my cell phone. I uploaded it to the internet and all three of them were fired."

"Cliff," said Dan, "shove your cock into Gerty's pussy and don't be too gentle about it. Adam you can have her mouth, see if you can get your cock right down her throat. Barry, you straddle her belly and she will squeeze your cock between those melons she calls tits. After we've all come we can change places." Smiling, the three young men did as Dan had said, thrusting happily into their helpless slave.

Jenny was still standing in the room watching the show and hoping they would invite her to join in.

They didn't. "There are several implements available to enable you to punish your slave should you so desire, gentlemen," she said "whips, floggers, canes, etcetera. There are collars that will fit her wrists and ankles and two that will strap onto her tits. There is a hook in the ceiling and there is rope and pulleys should you desire to suspend her by her wrists or ankles or tits while you punish her."

All four of the young men had ejaculated on or inside their slave and they were changing positions.

Jenny marvelled at how quickly these young men could regain their huge erections.

Dan's penis was deep inside Miss Assbugger's throat, Adam's was in her vagina, battering her cervix with every thrust, Barry's was deep in her anus as she squeezed Cliff's erection between her breasts.

"I have to attend to my duties now, gentlemen," said Jenny, "if you require any food or drink or anything at all, just pick up the phone and name your pleasure."

"If we phone for food and drinks, Jenny," asked Dan, "will you show us your tits when you bring it?"

"I will bring you your food and drink stark naked if it pleases you gentlemen." She left the room.

Six hours later the young men phoned to order beer and sandwiches, a can of dog food and a dog bowl for their slave to eat from, and a bowl they could urinate in if she got thirsty. True to her word, Jenny arrived naked, apart from a black suspender belt, black fishnet stockings and black stilettos.

Jenny opened the door to the room and pushed her trolley in, smiling.

THWACK! "Thirty-two with the paddle on my big fat left butt cheek. Thank you, Master Dan."

SWIPE! "Thirty-two with the cane on my big fat right tit. Thank you, Master Cliff."

THWOMP! "Thirty-two with the flogger on my big fat right butt cheek. Thank you, Master Barry."

THWISH! "Thirty-two with the buggy whip on my big fat left tit. Thank you, Master Adam."

THWACK! "Thirty-three with the paddle on my big fat left butt cheek. Thank you, Master Dan."

Miss Assbugger was hanging by her ankles from the ceiling and the young men were whipping her naked body with several of the implements Jenny had mentioned earlier. She was covered with hundreds of angry whip welts and her body was trembling. Her nipples were still hard and erect.

The hanging slave's wrists were cuffed behind her and her voice was rising higher and higher as she counted the blows and at first Jenny thought she was reaching the limit of her ability to endure this torture, and then she realised that Miss Assbugger was having an almighty mind-blowing orgasm.

SWIPE! "Thirty-three with the goddam cane on my goddam big fat right tit," Miss Assbugger screamed, "Thank you, thank you, thank you, thank you, Master Cliff. Please whip my goddam big fat pussy and my goddam big fat nipples, Masters, please."

The four naked young men put down their implements of chastisement and sat down to enjoy their beer and sandwiches. The beer bottles were in a big bucket of ice.

"Shove a couple of ice chunks into Dirty Gerty's pussy, Jenny, would you? She needs cooling off a bit judging by that performance," said Dan, "shove a couple in her butt hole too. Nice tits, by the way."

"Thank you, sir," said Jenny smiling as she inserted the ice into Miss Assbugger's orifices, "nice cock."

"Thanks, Jenny," said Dan, "and you might have noticed that we've hung the old battleaxe so that her mouth is exactly at clit height. Please feel free to take advantage of that fact."

Jenny took a very large bowl from her trolley and placed it under the hanging slave's head.

"Thank you, sir," said Jenny, spreading her legs and shoving her groin into Miss Assbugger's upside-down face, "I don't mind if I do. Suck my clit, Slave, suck it good and don't stop until I tell you to."

"Yes, Mistress. Thank you, Mistress." Miss Assbugger sucked Jenny's clitoris with enthusiasm.

The four naked young men sat and drank their beer and ate their sandwiches and watched the show.

Eventually Jenny and Miss Assbugger orgasmed simultaneously.

"Ayayayayeeeeeeeee," screamed Jenny as she emptied her bladder all over the hanging slave's face.

"Mmmff mmmff mmmff mmmff," gasped Miss Assbugger, still sucking Jenny's clitoris.

"Stop sucking now, Slave."

"Yes, Mistress. Thank you, Mistress. I'm sorry I did not catch all of your piss in my mouth, Mistress."

"No, Slave, but I caught it all in that bowl. That's your drinks for the rest of today and tomorrow morning taken care of. If that bowl needs topping up I'm sure these gentlemen will oblige."

"Yes, Mistress. Thank you, Mistress."

"I have to leave now, gentlemen," said Jenny, "is there anything else I can do for you before I go?"

"No thanks, Jenny," said Cliff, "we're going to take a nap now, we might even sleep right through till morning. We'll leave our slave hanging there until we wake up. We'll leave that bowl on the floor there in case she pisses herself during the night."

"Yeah, Jenny," said Adam, "after breakfast we're going to hang her from the ceiling by her tits."

"If you like, Jenny," said Barry, "we'll phone you and you can come and watch, would you like that?"

"Ooh yes please, sir," said Jenny, "I love to watch tit hangings. I will look forward to it. Goodbye."

It was four in the afternoon on the following day. It was not only Jenny's duty to greet guests on their arrival it was also her duty to make sure that everything went smoothly upon their departure.

"Your luggage is already in the car that will take you to board your plane," she said, "we hope that you have enjoyed your stay at the Dreams Come True Hotel and that you will visit us again in the future. I trust that everything was to your satisfaction and that the four look-alike students we provided for your enjoyment were everything you hoped they would be, Miss Assbugger."