There was a knock on Fluttershy’s front door, so she left the kettle on the stove and went to answer it. As she opened the door, a tingle went down her spine. “Hello, Cheerilee.”
She smiled. “Hi, Fluttershy.” Cheerilee walked inside and looked around. Fluttershy was wearing a beautiful pink blouse with yellow flowers on it and a pair of faded jeans. There were tea saucers on the coffee table and she went over to take a seat on the couch. “That’s a lovely top, Fluttershy.”
“Thanks. I’m glad you came over.” She eyed her guest from head to toe, taking in the rather plain outfit she could afford on a teacher’s salary. Not everypony could be friends with Rarity and afford nicer things, and her tan shorts and shirt looked like something out of a bargain bin.
A loud whistling sound came from the kitchen, drawing Cheerilee’s attention. She saw Fluttershy walk into the kitchen and pull a kettle of boiling water off of the stove. A minute later she walked into the room with tea bags in nice cups, filled with steaming water. Fluttershy set them down on the table.
“I’m really glad you invited me over, I’ve always wondered why you always seem to avoid me in town. I guess I was just being paranoid.” Cheerilee smiled.
“Oh, it’s nothing like that. Do you want sugar?”
“Two lumps, please.”
Fluttershy picked up the small tongs and dropped two cubes of sugar into Cheerilee’s cup. She then stirred her own tea and pulled the bag out. “Well, I was just shy. I’ve wanted to invite you over for so long I just had to be…ready.”
Cheerilee took the tea bag out and lifted the cup up to blow on it. She took a sip of the hot tea and tasted chamomile and something bitter. “Hmm, an interesting flavor. So, tell me a little more about yourself.”
She drank some of her own tea and set the cup down. “Oh, there’s not much to tell and we’ll have plenty of time to chat.” Angel jumped up on the coffee table and began to gesture at Cheerilee. It looked like he was begging for something, possibly Cheerilee’s tea. “Angel Bunny! What have I told you about getting on the furniture?” She brushed him off the table.
“Hmm, odd. He always seemed so well behaved.” Cheerilee took a longer drink of her tea, feeling her forehead begin to sweat. “My, it seems hot in here.”
“Oh, I’m sure it’s just you,” Fluttershy replied.
Cheerilee felt her throat tingling and tightening up, dry as cotton. She tried to drink some more tea and looked at her hand, shaking and spilling the tea everywhere. Her vision got blurry and she struggled just to let go of the cup. “F-Flutter—”
There was a thud as she toppled off the sofa and hit her head on the floor. Angel was hiding under the couch now, watching as Cheerilee was grabbed by the armpits and dragged off towards the basement.
Fluttershy was grinning ear to ear as she pulled the unconscious mare down the steps to the cellar. It was a wide room underground, perfect for what she had in mind. All those years, all the uncomfortable silences, it would all be worth it tonight.
Cheerilee’s shirt was cut off and her bra removed. She was a beautiful woman despite her small bust.
Next were her shorts, which she unbuttoned and tugged off. Once they were removed, Fluttershy pulled out the black thong and red skirt she remembered. The school uniform was very specific, the same today as it had been when Fluttershy was a filly.
It was easy to get the thong and skirt in place, and she fastened it to her waist. It was a bit small on Cheerilee, but the fact it wasn’t large enough to cover her entire ass seemed fitting, in a way. The black tights proved to be a little trickier. Fluttershy had rolled them up and placed them over Cheerilee’s feet, then began to unroll them. It took a lot of time to straighten them out and get them just right, lifting the limp legs one at a time as she worked.
The hardest part was getting her into the white button-up shirt. Fluttershy slid one arm through, then lifted Cheerilee off the floor. The other arm went through the shirt and she straightened it out before laying Cheerilee down. Fluttershy didn’t bother with a bra, instead just buttoning up the tight shirt against her stomach.
As she buttoned it over her breasts, they pushed back against the fabric, stretching it out. With the top button undone, the shirt revealed the best features of Cheerilee’s chest. There was still the tie to put on, so Fluttershy fastened it loosely around her neck. She fixed the collar and got things just right so you could see a little more cleavage than the dress code had allowed back then.
Cheerilee looked perfect, just like the mare in flight school but without the wings.
Fluttershy dragged her over to a wooden table and lifted her up onto it. Built into the table were thick leather straps. Cheerilee’s wrists were buckled into the straps, forcing her stomach against the planks of wood. Fluttershy fixed her skirt and adjusted it, then spread her legs to fasten them to the legs of the table. She’d be stuck bending over like this until Fluttershy let her free, and she didn’t plan to do that.
Cheerilee groaned as she woke up, feeling first the bump her head had taken. As she tried to rub her head, she felt a sharp bite as the leather dug into the skin of her wrists. Next was the ankle cuffs as she tried to stand up, and straighten her waist out. Both her feet were trapped by the straps.
While she struggled her way back to consciousness, Fluttershy grabbed the largest ball gag she could find and carried it over. Without warning, she reached around Cheerilee’s head from behind, and yanked the gag into place. Fluttershy put her body weight into it as she pulled the strap to the final hole, and buckled it into place.
There was a clear depression all around Cheerilee’s face where the strap had dug in, turning her upper cheeks red as blood couldn’t circulate back out. The ball in her mouth was pulling back at her lips so hard she could taste a little blood. Her jaw was forced wide open, and the pain served to finish waking her up.
Fluttershy walked around to the front of the table, her kind demeanor gone. In its place was something few ponies had seen on Fluttershy’s face: anger. Her brows were furrowed and her narrow eyes looked down on Cheerilee as if she were a violent criminal.
“All these years, all the things I’ve wanted to say and do to her, and then you came along…” Fluttershy continued to pace around the table, finally reaching for a three-inch wide strap of leather attached to a small handle. She walked over and lifted the skirt from Cheerilee’s backside, squeezing one of her ass cheeks.
Cheerilee mumbled and groaned into her gag, tugging at the straps holding her in place. She let out a yelp in pain as she felt a burning sensation and heard a loud slap.
Fluttershy pulled back and spanked Cheerilee again, the nylons doing nothing to dull the pain. They did hide the quickly-growing red welts on her body. She showed no mercy, striking the exact same spot a third time, before pacing around the table again.
The wood of the table creaked as Cheerilee struggled to pull free. It was useless, so she looked around for some sign of what was going on. The walls were bare of decoration, instead bearing only things like chains or saws. It looked more like a workshop than a room she’d expect in an animal caretaker’s house.
“You look exactly like her, you know? Minus the wings. I’ve got so much to get even for.” Fluttershy raised the strap of leather and swung it down. A loud crack echoed in the small room only once, replaced by a squeal of pain and frantic breathing. The now-red and sore right ass cheek was quickly getting a duplicate, as Fluttershy swatted her left cheek again.
“Mmmgpppghgg?!” Cheerilee tensed all her muscles at once and felt her wrists getting cold and numb. She was struggling so hard she was cutting off her own circulation.
“Oh, we’re just getting started. What’s the matter? Too quiet to speak up and ask me to stop? Too scared to say something?” Fluttershy brought the strap of leather down for her seventh time tonight. The sore, burning flesh began to ache with renewed pain.
Tears streamed down Cheerilee’s face as she struggled to figure out what was going on. She hadn’t done anything wrong, Fluttershy had always avoided her in town. Her train of thought was interrupted by another loud swat, and she convulsed a couple times against the table, feeling her heart pounding against the wooden boards.
“Too shy to even defend yourself. Who’s pathetic now?” Fluttershy lifted the strap and began to hit Cheerilee’s as fast as she could. She lost count at ten, feeling the burning in her shoulder as she lifted her arm again and again, just to smack the leather down on her rear end.
Finally the pain in Fluttershy’s arm was too much and she dropped the strap, stretching her arm. Cheerilee was thrashing wildly against the table, causing the legs to come off the floor and the table to slowly wiggle across the room. Her ass wasn’t bleeding, but the bright red of the welts easily showed through the thin pink fur and black stockings now.
It had been a good fifty or so hits, and it felt to Cheerilee like she had sat down in a fireplace. The burning was so intense that she thought it might actually blister and split open, her skin so abused that it couldn’t possibly hold together. It had held together, however, and continued to throb in tempo with each heartbeat.
Cheerilee was trapped in her schoolgirl’s outfit with her upper thighs on display. She felt Fluttershy’s fingers dig into her butt cheek. She cried out in agony, unable to make any comprehensible sound.
“Oh, I know what you want, but you won’t get it. Do you know how many times I went home from school early just to cry in my room? I guess not…” Fluttershy looked at the table, just wide enough that it gave her an idea. “Why don’t we try something else?”
Cheerilee whimpered, her head resting in a pool of drool and tears that was slowly being absorbed into the table. She felt her right ankle released and tried weakly to kick her leg. Fluttershy had a firm grasp on it, and stretched it out until it sat on the table. Her leg was now at a nice ninety degree angle from her waist, and Fluttershy found some rope to improvise a strap to keep her leg there.
The rope itself was abrasive and burned Cheerilee’s skin, but it wasn’t until the knot was tied that the rope truly bit into her flesh. She tried to bend her knee, but her leg was stretched out all the way. Her thighs burned from the stretching, and she tried to move her one leg on the floor to make the pain stop.
Fluttershy giggled at her pathetic attempts to get free. “Oh, you’ll never be a cheerleader like that. Maybe I wasn’t good enough, but I bet you couldn’t even do the splits.”
Cheerilee felt her left leg released and pulled upward. She kicked and struggled to get out of Fluttershy’s grasp. She succeeded momentarily, as her body couldn’t stretch in the way Fluttershy wanted.
Giving up on tying her to the table after putting her in the splits, Fluttershy instead bound some rope around her ankle, wrapping around the leg nearly a dozen times. She tied off a couple knots and found an eye bolt on a nearby workbench. While Cheerilee kicked her leg around a little, Fluttershy screwed it into the table and put the rope through it.
Next Fluttershy began to pull on the rope, straightening Cheerilee’s leg out and bringing it up onto the table. She was doing the splits now, but not fully. Her left leg was only halfway there, and Fluttershy pulled harder, aiming for perfection.
Cheerilee screamed as she felt tendons and muscles stretch. The burning in her inner thighs intensified as they began to tear. She’d never stretched or even tried to do splits, so her tendons were far too short to reach. One by one, fissures formed in them and the burning got worse.
She tried to kick her leg back and instantly regretted it. By tightening up her muscles to try and resist, she began to tear a tendon in her left leg. There was a small audible pop as it was strained past the breaking point, and Cheerilee’s leg slid up into position.
Fluttershy tied it off, looking at the pony now doing a perfect one-hundred eighty degree split. “There you go! I guess you were cheerleader material after all.”
The pain was so intense that Cheerilee was struggling to breathe. Her entire body was frozen in place as she focused on not moving. The muscles that had been pulled outward were running out of energy, and burning to return to their normal resting state. The tendons that weren’t broken were badly torn. If she wasn’t careful, she could easily snap more of them.
Fluttershy picked up a camera and took a picture from behind the mare. Her two legs were interrupted only by the thin black thong, and the red skirt that was slightly draped over her thighs. The stockings had torn down the middle, exposing the inside of her legs. In addition, some wooden splinters had caught the stockings and made several small rips.
Next, she got a small feather duster and went over to one of her prisoner’s feet. She began to dust it lightly and found her prisoner was very ticklish.
Cheerilee laughed, but the twisted sound that escaped the gag sounded more like a cough. Her legs twitched as they tried to pull away from the tickling, which caused a searing, stabbing pain in her thighs.
Fluttershy tickled her right foot a little longer then went over to her left. Knowing it was hurt worse than the other leg, she focused on tickling her for several minutes on that single side.
Cheerilee felt like the ligaments were tearing from the bone, the pain so intense she was certain her legs were going to fall right off at any moment. Luckily her ligaments hadn’t broken yet, they were just strained nearly to the breaking point. She looked at Fluttershy seeking mercy before the mare rendered her unable to walk.
She tossed the duster aside and went to get something else from the workbench. It was a metal device looking somewhat like a pear attached to a stick. Fluttershy carried it over and began to rub Cheerilee’s sore thighs. “How about a little reward, slut? You did always get the stallions when we were young.”
The restraints strained against the wood as Cheerilee pulled back from Fluttershy’s touch. The metal pear was slowly pushed against her womanhood. The cold metal was unyielding and forced its way past the lips of her pussy. Cheerilee let out a muffled cry of pain, her attempts to avoid this violation of her privacy were useless. The pear felt like it was stretching and tearing her dry slit, and let out a sigh of relief when it finally stopped.
Fluttershy smiled and begin to twist a knob on the end of the device. She kept this grin as Cheerilee looked down at what she was doing.
As the metal pear began to expand, three thick segments were pushed outwards. The choke pear began to blossom inside of Cheerilee’s cunt, putting intense pressure in every direction. At first it felt like she was at a doctor’s office, but that quickly passed. It began to strain against her muscles to push the narrow canal ever wider.
Rapid breathing and whimpers of pain filled the room as the pear continued expanding. It felt like her hip was being broken and ripped apart from the inside. Her legs were trembling and she felt lightheaded as the pressure increased in her stomach. The metal tongues of the device began to tear flesh inside her from the stretching.
When blood began to trickle out, Fluttershy stopped. She just enjoyed the pained expression as Cheerilee looked around, so panicked she couldn’t even focus on any one thing in the room. Fluttershy finally began to unscrew the torture device until she could slide it out. The metal pear was now stained with a little blood, but unharmed; the same could not be said for Cheerilee’s pussy.
Fluttershy put the device away and went back to see her prisoner’s face, taking great pleasure in the wet spot on the table from all of her pathetic whimpering. “Oh, I think I’ll leave you like this all night.”
Cheerilee didn’t know why she was being tortured, but she fought hard to shake her head and mutter out a single word.
“Hmm? You don’t want to spend the night like that? Crying, all alone? I spent plenty like that.”
She made a few short grunts and shook her head.
“How fortunate for you I’m not a monster. You just look exactly like an old bully I used to know, and I never got to get even with her… I don’t want you to die, not yet, and I think I know just the device to let your sore legs recover.” Fluttershy reached her right arm and unbuckled the strap.
Cheerilee tried to yank her arm away, and Fluttershy slammed her fist into the back of her head, crushing her nose against the table. Now Cheerilee could see the blood mixed in with her drool on the table.
Seconds later, her wrists had been tied together over her head. Fluttershy went back and untied the ropes from the table, but left the knots on her legs. As the second rope was released, Cheerilee fell backwards onto the floor.
Her legs finally pulled closed, but the pain only got worse. The soreness and burning of so many damaged muscles was renewed, and her legs felt like rubber. She tried to stand, to run, or do anything, but the pain was too great. She just wanted to curl up and cry.
Fluttershy had other plans, dragging her over to a special bed by her wrists. She took a rope attached to a pulley and hoisted Cheerilee up by her arms. The bound mare might have been able to kick Fluttershy with her free legs, were they not dangling limply and feeling like knives had been jammed into every inch of them.
Once Cheerilee was hoisted over the bed, a knot was tied off. She looked down and saw hundreds of nails sticking through the bed, pointed upwards. Her eyes went wide as Fluttershy threaded the ropes through small holes in the bed, and tied them down. On each end of the bed was a wheel to put tension on the ropes and force her feet into the nails.
Cheerilee pushed with her feet and felt dozens of pin-pricks along the soles. “Careful now, I wouldn’t want you getting hurt unless I’m the one doing it. This has been very theraputic so far.”
Fluttershy turned the levers and the ropes tightened up, pulling Cheerilee’s feet into the bed of nails. Cheerilee looked down as they pushed against her feet, but with the weight distributed evenly, no one nail punctured her skin. Once she had gotten each foot tight enough, she leaned over to closely examine her handiwork.
Each nail was pushing in about half an inch. The thick skin of the foot was near the breaking point, but so far had not torn open under the assault from the nails. Fluttershy had made sure the nails were blunted before building this bed.
Cheerilee squirmed uncomfortably. The pressure was quite painful where the nails had met bone. Her heel and the ball of her foot were the worst, having the least fat to pad them from the torture device.
She nearly lost her balance and fell over when the rope over her head was given slack. Now Cheerilee was standing and balancing herself on the bed of nails.
“I wonder how much more pressure your feet can take before all the nails have broken the skin.”
There was a steady click every couple of seconds as Fluttershy slowly tightened the ropes. This forced Cheerilee’s feet and body weight to push down more on the nails.
Cheerilee felt stabbing pains shoot through her feet and she struggled to lift her feet. In order to lift one foot she had to push down with the other, and after mere seconds, her struggling caused half the nails to penetrate her foot.
The ball and heel of her foot were now dripping blood down the long pointed nails. Cheerilee’s bones began to grind against the nails as her weight settled and she stopped moving entirely, except to breathe and whimper in agony.
“Fascinating, the nails still haven’t broken the skin in the arch of your foot.”
The next click caused Cheerilee to panic and struggle, despite the pain. Fluttershy was tightening the ropes further. Her feet felt as though red hot pokers were being driven between the bones. She was getting dizzy and lightheaded just imagining the dozen or so nails squeezing their way between her bones. If she could see her own foot, she’d realize there were at least sixty nails under each foot, every one having torn the skin.
Fluttershy finally stopped, looking up to see Cheerilee’s head hanging. She got up and lifted Cheerilee’s head up to look in her eyes. “Oh, it’s not so fun on the receiving end, is it? This little session has made me feel much better, however, so I suppose I can let you down…maybe go out and get you a tetanus shot tomorrow.”
Cheerilee had run out of tears, and her throat was dry. All she could do was weakly shake her head and try to pull back from Fluttershy.
There was a loud click as the tension was released and the ropes went slack. Cheerilee fell forward, but Fluttershy was ready with the rope threaded through the pulley overhead. She used it to slow her fall to the ground, and watched the mare lay limp in defeat. There was a lot of blood on her feet and dozens of small puncture wounds.
Since Fluttershy didn’t plan to let Cheerilee die anytime soon, she got a bottle of rubbing alcohol and poured it on her feet.
Cheerilee let out a hoarse grunt in pain, her legs twitching, as the alcohol seeped into her flesh and renewed the burning agony of the nails. Her will to fight was almost gone, her mind so clouded with pain she couldn’t even remember why any of this was happening.
She felt her body dragged over to the wall and her arms hoisted up. There was the rattling of a chain, and metal shackles closed around her wrists. They were locked in place, the three-inch thick steel securely wrapped around each wrist, holding them together.
Fluttershy fastened the chain over her head, leaving Cheerilee to sit against the wall with her arms painfully stretched upward. Her legs were spread out in front of her, still oozing blood. Fluttershy soaked a towel in the alcohol and placed it on the ground, folding it over her feet. She delighted in hearing her weak whimpers from the renewed pain.
Much to Cheerilee’s dismay, Fluttershy grabbed one of her feet and began to rub her thumbs against the sole hard. The towel began to get stained red as she massaged Cheerilee’s foot. When Cheerilee began to whimper in renewed pain, Fluttershy stared up at her, frightening Cheerilee into silence.
The right foot was done with the massage now, and the towel a pink color from the mixed alcohol and blood. Each hole from a nail was filled with alcohol and burning to the point that they went numb.
Fluttershy squeezed her left foot as hard as she could until she could feel the bones rubbing against each other. Cheerilee hit her head on the wall as she recoiled from the pain. For agonizing minutes the massage continued, until at last Fluttershy has stained the entire towel.
Cheerilee tried to kick off the towel and continued to spasm from the torture. “Oh, shut up,” Fluttershy said, “I’m doing you a favor. If this towel has moved an inch in the morning, I’ll tie you down to the bed of nails and you’ll sleep there from now on.”
Cheerilee made her incoherent mumbling noises again, the chain rattling as she moved her arms.
“Good point, I’ve got years worth of pent up anger to get out… we’ll save the bed of nails for later. There’s just one last thing I need to do then you can get some sleep. I need to take a momento of our first day together.”
Fluttershy walked away and opened a toolbox. She came back over to Cheerilee, twirling a scalpel around in her hand. Fluttershy knelt and looked at her right ankle. “Hmm, this will do nicely.” She sliced the flesh above the ankle, then sliced again, making a narrow strip of skin. Only an inch long and an eighth of an inch thick, it would scar and heal quite nicely.
She placed the strip of flesh into a small compartment in the toolbox and put the scalpel away, then came back over and grinned. “This was very fun and relaxing. Thank you. And just think, each day I’ll take a pound of flesh until you’ve got none left to give. Then, I’ll toss your remains into the Everfree for the wolves.”
Cheerilee’s head hung limply as she cried, every muscle from the waist down throbbing and sore. The light flicked out and left Cheerilee to ponder her slow agonizing death as piece by piece, Fluttershy tore her apart.