Academy Anal Punishment

S.M. Wolf

Story, artand Mistress Miao © 2006 by S.M. Wolf, all rights reserved. Reproduction and distribution of this workby any meanswithout the expressed written permission of the author, or hotlinking from another website without the expressed written permission of the author is expressly forbidden. Any resemblenace to any person, living or dead, is purely coincidental.

Introductory Anal Sex for Male Furs was the first time most of the males had ever had homosexual sex. The Academy used it as a way to further break the wills of the male slaves and mold them into obedient pleasure slaves.  It also served a very practical purpose. About a quarter of the class could expect to be regularly lifting their tails to accept the intrusion of their Master’s hard cock into their tight tail holes. Those Masters expected well trained and pleasing sex slaves to satisfy their carnal lusts.

A dozen of the new males were led into the classroom.  Half of the males were bent over heavy tables and secured to rings set in the wall.  The other half was positioned kneeling on the floor behind them.  The guards used the occasional quirt to the inner thigh to get the inexperienced trainees to spread their legs wide and present their cocks to open view.

Several of the males swallowed audibly or paled when the guards deposited large containers of petroleum jelly on the tables beside the rumps of the males on the tables.  Most of the guards openly laughed at the slaves' discomfort. For the slaves it was their first training class involving sex following the intensive computer indoctrination. The guards looked forward to their reactions when they were forced to mount or be mounted by another male. They pawed several of the males' asses as they walked among the slaves.

The breath seemed to leave all of the slaves when the red PVC clad femfur stormed into the room.  Mistress Miao was known throughout the Academy among both slaves and instructors for her 'enthusiastic' training methods.

"All right, let's get going!  We have little time.

"Slaves on the floor get up and grease the anus of your partner on the table.  I want at least two well lubricated fingers in your partner's rectum up to the second joint within five minutes.

"When you get him greased up, lubricate your prick and mount him hard and fast. I want to hear flesh popping when you fuck him.


The tiger had drawn a slightly built skunk as his partner.  The somewhat effeminate male skunk looked back at him with pitiful eyes, but the tiger just shrugged. He could not do anything but obey.  He pressed the wide skunk tail forward and proceeded to lubricate the skunk's rectum as ordered.  The skunk writhed under the tiger's touch and whimpered continually.

When he was done greasing the skunk, the tiger coated his cock with petroleum jelly. He was surprised to see that he was already sporting a hard-on.  He had never considered a sexual relationship with a male before, and now he was about to rape this skunk.  For some reason the idea excited him. Apparently the Academy’s indoctrination worked on him well.

The programming had broken many of their inhibitions, but several of the males were still squeamish at the thought of mounting another male.  A liberal dose of lashes from the guards' quirts encouraged the slaves taking the top position into performing.

The tiger was nearly unnerved when the skunk screamed as the tiger pushed just the tip of his cock into his partner's ass.  The tiger would have withdrawn, but Mistress Miao struck his ass with a hard blow from her riding crop.

"All the way in!  Now!"

She emphasized the point with two sharp, stinging blows of her riding crop to the tiger’s ass cheeks.

The tiger could do nothing except comply.  He thrust hard and buried his cock deep into the skunk's bottom.  Despite the skunk’s screams and thrashing body, he repeatedly withdrew and thrust until he finally came.  His jism spurted into the skunk's rectum. At last he was done and could stop raping the skunk.

The tiger sunk down to the floor and knelt waiting. He was forced by his position to look at the skunk’s red anal rose. When all of the males were done cumming, Mistress Miao ordered the pairs switched. Now the tiger found himself bent over the table, secured to the wall with his tail high in the air.

“Now you get a chance for some payback,” she told the class.

“Grease them up and bugger them!”

The males complied with varying amounts of enthusiasm. The skunk barely seemed to want to move. His efforts were pitifully slow and inept. They soon attracted the attention of their instructor.

Mistress Miao brought the riding crop down on the skunk’s ass several times.

“You are pathetic!” she screamed at the cowering skunk.

“Now get to work. I want all four of your fingers in his rectum in two minutes or you will wish you had never been whelped!”

With the Mistress standing over him in an obvious furor, the skunk could only try his best. Somehow he managed to get the tiger’s pink anal ring stretched open and four fingers inserted before time ran out.

“Good!” Mistress Miao said sarcastically.

“Now there is just one more small thing…”

Without warning Mistress Miao grabbed the skunk’s arm and shoved it forward. His entire fist disappeared into the tiger’s ass. The tiger screamed in shock and pain.

Mistress Miao grabbed the tiger by his hair and bent his head back.

“Don’t think I missed your earlier reluctance, slave. I never miss anything that happens in my classroom, no matter how small, and I never fail to punish those who deserve it!”

She looked at the other slaves. All of them had stopped their screwing and were watching the feline femfur in wide-eyed terror.

“Did I tell you that you could stop?” Mistress Miao inquired sweetly.

The room suddenly echoed with grunts and flesh smacking flesh as the males started to mate furiously. None of them wanted to share the fate of the tiger and skunk.

“You,” Mistress Miao told the skunk, “get to work under this tiger’s tail.”

The skunk withdrew his fist. The tiger grunted as his behind was emptied. The void was rapidly replaced with the sleek, well lubricated shaft of his skunk partner. The skunk seemed to have no desire for this sex play and took many minutes to finish. Indeed, the rest of the class was done well before he returned to a kneeling position behind the tiger.

The class continued for some time. After each group orgasmed the males were switched. Sometimes they had to mount their partners hard and fast. Other times they had to draw out the experience until their partners spurted their seed on the floor. Quirts were used liberally on the back sides of the males, and Mistress Miao’s riding crop seemed to always find the tenderest spot of any slave dallying in his lesson.

Mistress Miao paid particular attention to the skunk and tiger. While the tiger likely could have performed acceptably with another partner, the skunk spoiled much of his efforts. Both males found themselves frequently the target of her riding crop.

After more than an hour the class finally ended. Each pair had to carefully clean up their partner’s anus and remove the grease and cum covering many of the males’ buttocks. For the skunk this must have been particularly painful as his anus was quite raw and somewhat swollen from the repeated entry of the tiger’s cock.

Mistress Miao eventually dismissed the class except for the tiger and skunk. The other males were grateful to head to the baths and dinner. After this day even the straw of the kennels and any fitful rest they could get would be welcome after their first day of classes.

"You two did so well, you deserve some extra 'training'!" she informed the worried sex slaves after the others had left. They cringed at her words.  Even though they were new to the Academy, they had already heard word of Mistress Miao and her cruelty towards the slaves from other slaves in the baths.  The faux castle dungeon had several possible ways to punish poorly performing slaves.

Mistress Miao did not keep the pair waiting in suspense. Soon the tiger was chained to a wooden horse.  He was on all fours with his tail pulled straight up by a rope attached to the ceiling.  A ball gag was inserted into his mouth, and a short chain snapped to his nose ring.

The skunk was forced to kneel beside him, roughly even with the tiger’s butt and ordered to watch and wait his turn.

Mistress Miao brought in a strange machine.  It consisted of a motor and a piston mounted on a table.  She placed it behind the tiger with the rod pointed dead center at his ass hole.

Mistress Miao disappeared for a moment again, but returned quickly with three large dildos.  The two largest she placed on the table beside the machine, but the third went on the end of the rod.  She pushed the table forward and forced the dildo into the tiger's tail hole.  He tried to scream as the unlubricated intruder forced its way between his ass cheeks, but the ball gag effectively silenced him.

Mistress Miao flicked a switch, and the .motor hummed to life.  The piton drove the dildo back and forth into the tiger's rectum.  There seemed to be some sort of random control as it continually varied the depth, speed and timing of each thrust to keep the tiger guessing.

Mistress Miao grabbed the chain dangling from the tiger's nose ting.  She pulled his head up.  She lifted her left foot and placed it on the tiger's right paw.  She put her weight on his paw and pressed down almost painfully.

Tiger Anal Punishment

"Maybe next time," she said cruelly, "you won't be so prissy about getting reamed.

"In the meantime, you can look forward to another fifteen minutes of this."

The tiger tried to scream again and again as his bottom was violated time and again by the mechanized dildo, but little sound escaped past his gag.

Mistress Miao looked over at the skunk and commanded him, "And you watch closely!

"As bad as you were you get twice the punishment, and I have a 'special' cream for you to help you improve your performance!”

Mistress Miao's grin grew even larger and crueler if possible.

"I am really looking forward to hearing your screams and pleas for mercy."

The tiger heard the skunk whimper, but he had little time to worry about him.  His anus was rapidly becoming raw and painful as the piston contused to thrust the dildo deep within his ass.

The fifteen minutes seemed to last a lifetime.

Eventually the tiger’s punishment was done. Mistress Miao left the dildo in his ass but removed the chains securing him to the horse.


The tiger slid forward off the dildo. It was just a little extra indignity to the slave, the cherry on the top of the ice cream so to speak, but it was effective in reminding him of his position in life now. Mistress Miao pointed to a spot beside the horse opposite the skunk. Almost gratefully he sank down to his knees and adopted a submissive posture with his knees spread wide and paws placed on his thighs palms up.

The skunk was trembling visibly. The tiger was not sure what he would do.

Mistress Miao reached down and caressed the skunk’s muzzle.

“Scared, little one?” she asked in a purring voice.

“Y- Ye- Yes, Mis- Mistress,” the skunk managed to stammer.

“Good!” Mistress Miao said enthusiastically.

“I doubt I will have to repeat this particular lesson with you after tonight then.”

Mistress Miao pulled back the machine and removed the dildo used on the tiger. She replaced it with the long smooth dildo. When she was done, Mistress Miao patted the horse.

“Up!” she commanded the skunk almost cheerfully.

With visible reluctance the skunk climbed onto the horse. The tiger watched with considerable sympathy as the skunk was secured to the horse. He was thankful when Mistress Miao unclipped the chain on his nose ring and placed it on the skunk. Apparently the skunk’s nose was as sensitive as the tiger’s. He yelped at the sudden addition of weight.

The tiger had a perfect view of the dildo being inserted deep into the skunk’s ass when Mistress Miao slid the table forward. The skunk screamed, and his back arched in pain. That did not deter the feline femfur in the least. She made some adjustments and switched on the machine.

The tiger watched in fascination as the dildo slid in and out of the skunk’s anus. He watched as it pulled and pushed the skunk’s pink rose in and out. Having just experienced the same, he could well sympathize with the skunk’s cries of pain and shame.

The new dildo was a good twelve inches long and at times the entire length would disappear into the skunk’s bowels. Apparently he found it very unpleasant, but he could do nothing to stop it. The smooth intruder continued to plow its way into his behind for a solid fifteen minutes.

When the machine stopped the skunk raised up his head in relief thinking his torment was over.

Mistress Miao instead grabbed his nose ring chain and pulled him forward until the dildo slipped out of his ass.

“That is just the first part of your punishment. I have more for you…”

The smooth dildo was replaced by one with many ribs. From inside the cleavage of her PVC top Mistress Miao brought out a red tube. She carefully opened it and squeezed out a white cream onto the dildo. Even at a distance of several feet the tiger could smell pepper.

Mistress Miao grabbed the base of the skunk’s tail and pulled backwards. His anus slipped over the tip of the dildo and came to rest against the ribs. The skunk looked back over his shoulder and pleaded, “Please, mistress! I will do better next time!”

“Oh, I am sure you will,” Mistress Miao replied, “if for no other reason than to avoid this!”

Relentlessly the feline pulled the skunk fully onto the dildo. He screamed and begged for mercy as he felt the pepper oil laced cream coat his ass crack, anus and rectum. Mistress Miao just laughed and turned on the machine again.

The tiger was forced to watch and listen to the skunk's screams as his punishment continued for another fifteen minutes. By the time it was over the male had been reduced to a sobbing mass of fur from his pain and debasement.

Mistress Miao removed the machine and put it away. The tiger was surprised when she ordered him to stand behind the skunk.

“Mount him again. When you are ready to cum, pull out and coat his ass. I want you to cum three times to finish your punishments.”

The tiger reluctantly placed his paws about the skunk’s waist. Again he was surprised to find himself hard from watching the skunk’s punishment. briefly he wondered about his reaction to the sights and sounds of the punishment of this male skunk.

The tiger’s first thrust was deep and hard. He hardly met any resistance at all form the widely stretched tail hole of the skunk, but he immediately withdrew and howled. His cock was on fire from the pepper oil cream still in the skunk’s rectum.

“Oh, yes,” the feline Mistress purred, “I imagine that was not pleasant at all. However it will teach you to do better in the future.

“Now get to work!”

The tiger somehow managed to continue his anal sex with the skunk. Each thrust was pure hell as he recoated his shaft with the pepper oil. It also dripped down onto his ball sack to compound his agony. Still he managed to reach orgasm three times though it took him more than a half hour.

Mistress Miao surveyed the standing tiger and nearly doubled up skunk. Despite the skunk’s obvious problems he was still alert and supporting himself. The tiger looked like he would have been able to continue as well. Both had obeyed her orders despite tremendous personal pain.

She purred contentedly as she released the pair. They were a pair of diamonds in the rough that had considerable potential for future fun with her and with the paying customers who enjoyed some of the more “exotic” offerings of the Academy. For now she would take them to the medical ward for treatment, but in the coming months she would be sure to take these two under her wing for special instruction at every opportunity.

Mistress Miao was looking forward to several months of fun before the pair of males was sold.

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