Lesson 11, Endurance training
Silver Wing, a Pegasus with a coat that matched his name, sat in his office, looking thoughtfully through a seemingly endless stacks of reports and mission requests he had to file away. Running a Guild was not the walk in the park he had hoped it would be, but he and his friends were doing their best to help the ponies of Equestria, so he’d deal with the paperwork, no matter how endless it seemed.
A clock on the wall nearby emitted a series of chimes and Silver sat back in his chair and stretched. “Noon,” he sighed, “Guess it’s time to go check on Sky Flare.”
He was glad for the break, and a slight groan escaped him as he rose to his feet. He stretched lazily, then trotted towards the locked room at the back of his office and unlocked the latch. The door swung open slowly, and as the light of his office flooded into the dark room beyond, he grinned at the sight before him.
His long-time friend, Sky Flare, hung from a series of chains that were anchored to the floor and ceiling. Metal cuffs with furred padding to avoid chaffing were secured to her wrists and ankles and pulled her limbs taut, holding her in place within the room. She was forced into a wide “X” like pose, with her arms held outstretched towards the ceiling, while her legs were held just above the floor. Her wings too were bound, though far more carefully than her limbs. Black silken wraps were tied around them and wrapped across her chest, binding her delicate wings tightly to her upper back.
Silver Wing grinned at the sight before him and crept over to his friend silently.
A heavy leather blindfold hid his approach from her sight, and the muffled buzzing sound of the wildly vibrating toy strapped in place inside her soaked marehood masked any sounds his hoof falls created.
As he drew close, he admired her sweat covered coat and grinned anew. The large ball gag in Sky Flare’s mouth glistened with her drool, and there was a sizable pool of her juices on the floor beneath her. Clearly, she had cum several times since he’d first slipped the vibrator into her earlier that morning.
Silently as a shadow, he moved behind her and slid his face just beside hers. He could see the hazy, pleasure drunk grin on her face, and while it amused him greatly, he couldn’t let her know, not yet anyways.
“I take it you enjoyed your morning?” He whispered hotly into her ear.
Sky Flare let out a muffled shriek of surprise and jerked on her chains as she tensed.
He chuckled at her reaction and traced a hoof slowly up her spine. He watched Sky Flare tense bodily at his touch and try to move away from him, but her chains forced her to remain close.
“Memuff Milmer! Meeease!” she protested weakly though the ball gag in her mouth. It had holes in it to allow for easy breathing, and semi legible speech, but it also forced the wearer to drool heavily, especially when they tried to speak.
Silver Wing watched the drool run down his captives chin and trail along her neck and shook his head in amusement. “I’m sorry my dear,” he cooed, “I’m afraid I can’t hear what you’re saying.” He slid his hoof back down her spine, then ever so slowly along her hip. He could see Sky Flare tremble at his touch and he bit her ear softly as he spoke again. “Mind repeating yourself?”
“M-memuff…” She tried weakly, “Mee-Ahn!”
As she tried to speak, Silver Wing slid his hoof down fast and pressed it hard against the vibrator that was strapped into his captive, forcing it even deeper inside her.
Sky Flare shook her head and panted breathlessly as the already mind numbing pleasure cascading through her abused nethers grew abruptly as her captors’ touch.
She shuddered as she was struck with yet another orgasm and with a muffled moan of release, fell limp and passed out from exhaustion.
Silver Wing chuckled and shook his head at her. He was pleased she’d lasted this long. Six hours was no easy feat, but he’d have to seem disappointed when she woke up. After all, he couldn’t let her feel like she’d succeeded so easily, not when they’d only just begun…
He left Sky Flare’s limp form chained up and trotted back to his office to continue his paperwork. He’d wake her in few hours, then the real fun would begin. Closing the door behind himself, he grinned as he thought about how all this had come to be…
It all started a few months ago. He’d been drinking with his friends as they celebrated, and he had let slip that he was a bit of a letch back where he was from. He knew a great many ways to pleasure a lover, and he had made the mistake of describing some of his techniques to his close friend Sky Flare. She was a Pegasus, like he was, with a fiery red coat and an equally fiery personality. She had pressed Silver Wing for more examples, under the guise of curiosity, but Silver Wing quickly learned that she was far more than simply curious.
Sky Flare had practically forced herself onto him that very night, demanding to experience his methods first hoof. Silver Wing had resisted as best he could, but there was only so long anypony could turn down such a haughty and lust fueled mare.
It started out simply enough. Different positions, different locations, role play, the occasional toy here or there, those sorts of things. But then, the wilder their encounters became, the more Silver Wing revealed his more guarded side, and Sky Flare in turn revealed hers. Bondage and rope play quickly became a favorite of the both of them, and then the next step happened… She had asked him to dominate her, in body and in mind, and his position as her one and only Master became absolute.
None in the Guild knew of this of course, as it was their most closely guarded secret. But so long as they were alone, she was his to do with as he pleased, and she loved every moment of it.
Silver Wing had written a book about the art of love making some years ago, and while he no longer had the original copy, he still knew all the lessons by heart. There were one hundred Lessons in all, and Sky Flare was only on the eleventh now. Lesson eleven was all about endurance, and learning just how much you could handle when it came to the more pleasurable side of stimulation. There were rougher lessons to be sure, but she wasn’t ready for those yet, she was barely ready for this one, but that was half the fun. Trying new things, testing your limits, and seeing what truly makes you tick. She had an out if she wished it, lesson four had been all about safe words and when to use them. So, as long as she didn’t use it, he had free range to keep her tied up all week if he wished to. Not that he would. They only practiced such things when the Guild was empty, which would only be for another few days, but they’d use what little time they had to its fullest potential.
As the sun was starting to set, Silver Wing rose from his desk once again, and checked in on his exhausted lover for a third time. She was still out cold and he shook his head at her. She’d only been strung up for six hours before she passed out, and the last six sleeping had apparently done nothing to revive her…
With a sigh, Silver Wing trotted out of his office and grabbed a metal bucket from the nearby storehouse. He filled it with water from the river than ran behind the Guild and returned to his captive, a grin of anticipation growing on his face.
“Wakey wakey my dear.” he called softly. Receiving no reply, Silver Wing hefted the bucket of frigid water and dumped it over Sky Flare’s unconscious form.
She awoke with a startled gasp of fear and confusion, then moaned deeply as her thrashing reminded her of the vibrator still buzzing away inside her marehood.
“Who said you could sleep, hmm?” He cooed.
“Mat mammet mife Milmer!” She growled angrily as she shivered from the cold that clung to her.
“It’s your punishment for disobeying my orders,” He stated simply, “Not only did I not give you permission to sleep, I recall saying that you couldn’t cum either, which you’ve clearly disobeyed quite a few times judging by the pool beneath you.”
Sky Flare was still blindfolded, but she glared angrily in the direction of his voice for a moment more, then looked away in embarrassment as she remembered her place.
Silver Wing smiled at her reaction and trotted up to her. Gently, he reached a hoof up and unclasped the cord holding the ball gag in her mouth.
She spat out the item and swallowed hard, though she didn’t dare say a word.
“Good girl.” He said. Next, he undid the clasp holding her blindfold in place and let if fall free. It dropped to the floor below with a slap as it landed in the pool of water.
Sky Flare knew better than to make eye contact without her Masters’ permission, but she couldn’t help but to glance in his direction nervously. She could never tell what he’d do next, even after all the times they’d played games like this before. It was always a thrill, but at the same time, a mixed knot of fear and anticipation always grew in her stomach when he was this close to her. Would he kiss her? Would he berate her? Whip her? She never knew, but she eagerly awaited the answer to her unspoken questions.
“So,” Silver Wing asked softly, “How many times did you disobey me this time, hmm?”
She debated lying to him by saying that she couldn’t remember after having been strung up for so long, but she knew he wouldn’t fall for that. Her memory was nearly perfect, and though she tried her best to resist the pleasure rising up within her, she could only take so much…
“S-seventeen…” She whispered shakily.
“Hmm?” Silver Wing said, “Speak clearly now.”
“S-seventeen times.” She said louder.
“What did you do seventeen times,” He asked, “You are not being clear enough my dear.”
“I…” Sky Flare started, then paused as she took in a deep, calming breath. “I disobeyed you… S-seventeen times…”
“Seventeen times?” Silver Wing whistled and shook his head, “That is quite the failing. I don’t know if I can continue to keep you as my Pet if you’re going to perform so poorly.”
She gasped and looked at him pleadingly. “N-no! Please Silver!” She begged, “Don’t say that! I’ll do better, I promise!” She bit her lip and looked away from him in embarrassment, “I-I mean… Master…” she corrected herself.
Silver Wing forced himself not to smile at her plea and simply shrugged. “You say that,” he said, “But I have a feeling you’re about ready to disobey me again at any moment.” He reached between her legs and pressed hard against the vibrator she still had strapped into her.
Sky Flare arched her back hard at the sensation, her chains clanking loudly as they were pulled taut. She bit her bottom lip as she tried with all her might to resist the orgasm she felt rapidly building within her loins. She’d all but forgotten about the vibrator, but her Masters’ touch brought its presence to the forefront of her mind like a scream of white hot pleasure.
Silver Wing shifted his hoof against the vibrator, forcing it to press this way and that. He loved to watch her squirm like this, and the sounds she made were almost too much for him to bear, almost.
Sky Flare’s mind went blank at the change in sensations and she gurgled out weakly as she was quickly brought to the very edge. “I-I’m..!” She said shakily, “I’m s-s-sorry!” Abruptly, the sensations she was being bombarded by vanished with a wet slurch and a distant thunk. She trembled in place breathlessly as she struggled to understand what had happened. Looking down tiredly, she spotted the strap in vibrator laying on the floor and could not stop herself from whimpering a little in disappointment.
“I heard that,” Silver Wing cooed, “You weren’t wanting to disobey me just then, were you?”
It took everything Sky Flare had to shake her head no, but she didn’t dare look at him just yet, lest he see her disappointment and desire as clear as day.
“Then it’s a good thing I helped you by undoing the straps of your little buzzing friend,” Silver Wing said, “Thank me for helping you.”
“T-thank…” She breathed out tiredly, “Thank you…”
“For?” He asked.
“T-thank you, f-for helping me…” She corrected.
“Anytime,” Silver Wing said, a charming smile crossing his lips, “After all, a Master always strives to help his Pet whenever she may be in dire need.”
Sky Flare smiled weakly at being called his Pet, then regretted her action as she found her Master to be watching her very closely.
“And why are you smiling, hmm?” He asked her seriously, “Have we forgotten that we have disobeyed seventeen times now, this morning alone? Eighteen if you count that little nap you took.”
She dropped her head in shame and fell silent.
“Better,” He said, “But whatever will we do with you…” He started to walk around her, circling like a shark as he thought on a fitting punishment for her transgressions.
Though she tried not to, Sky Flare couldn’t help but follow him as he circled her. She was exhausted. Her arms hurt and her stomach panged with hunger. On top of it all, her nethers were numb from the prolonged vibrations, and her mind was a haze of pleasure tainted emotions. She was so nervous as to what he’d do next, but deep down, she was still eager for more. She loved this. Being forced into his fantasies like this, being made to submit and serve… For reasons she did not fully understand, it made her feel complete, made her feel whole. She was always in charge in outside world. Always the top dog that made others quake in their horseshoes. But here? With him holding her leash and giving the orders? Here she could feel what it was like to be on the other side of things. Here, in secret, she could let herself be vulnerable and have her every fiber exposed and violated. It was exactly what she needed to really unwind, and she was grateful to whatever unseen gods had blessed her with that night that made all of this possible all those months ago.
“I know…” Silver Wing said softly.
Sky Flare tensed at his words, having been brought back to the moment by the amusement in his voice.
Slowly, he extended one of his wings and trailed one of its many flight feathers along her well-toned abdomen.
Sky Flare gasped and tensed at his touch. “N-no!” She squeaked, then she bit her lip again and cursed herself for breaking her silence.
“No?” He cooed. He twirled a feather in a small circle around her belly button and grinned as he watched her core muscles shift and tremble in response. “What’s the matter my Pet? You aren’t ticklish, are you?” He knew she was. Despite her love of combat and hoof to hoof fighting styles, Sky Flare was almost unbearably ticklish. Unfortunately for her, tickle play was one of his favorite things… Especially when his victim protested.
Sky Flare bit her bottom lip harder as she felt her Masters’ wing tip slither up along her stomach, then back down along her side and inner thigh. She shook her head in anguish and pulled hard against the chains that held her in place. She hated to be tickled, but at the same time, it drove her wild. The sensations were too much for her to bear, but she knew, the more she protested, the more he’d continue, so she’d have to endure it and make as little noise as possible.
Silver Wing smiled darkly as he watched his captives’ expression shift into one of dismay and he licked his lips in anticipation. ‘This is going to be fun,’ He thought, ‘Let’s see just how long you last this time…’
Brining his second wing into the mix, Silver Wing began to expertly and relentlessly trail his feathers all over Sky Flare’s exposed form. Nowhere was safe from his assault. Stomach, sides, thighs, arms, neck, he hit them all and reveled in his Pets’ wild thrashing.
Nearly every muscle in Sky Flare’s body burned with exertion from her failed attempts to resist her Masters’ torturous tickling of her body, and in less than a minute she was gurgling out a mix of laughter and tears.
Silver Wing grinned victoriously at his achievement and ceased his assault for a moment. He wasn’t cruel after all. He’d allow his Pet a few moments to catch her breath… Before he’d begin again.
Silently, he crept behind her and kissed an ear tenderly. “That makes up for one of your transgressions,” he whispered darkly, “Only Sixteen more to go…”
“W-what!?” Sky Flare squeaked out, “B-but-”
Silver Wing buried his nose into the soft spot in the center of her back, just between her bound wings and nuzzled into her expertly.
She practically screamed out at the sensation and tensed bodily. Her entire body locked up as her greatest weak spot was exploited. She couldn’t handle somepony touching her there, and when Silver of all ponies hit that spot, she couldn’t even breath anymore.
He kept her immobilized like that for a full minute before stopping to allow her to draw breath again.
Sky Flare gasped for air and looked back at him weakly and she was forced to pant. “N-not…” she tried weakly, “Not… Fair!”
“I’m the Master,” Silver Wing stated simply, “I don’t have to play fair.” He smiled at her for a moment, then said softly, “Fifteen transgressions to go.”
Sky Flare dropped her head in defeat drew in a ragged breath as she fought not to whimper.
With a grin, Silver Wing moved back in front of his Pet and nuzzled her stomach in much the same way that he had just nuzzled her back.
Instantly, she pulled her stomach away from him as far as she could and pulled against her chains as she tried to escape what she knew was coming next.
“And just where do you think you’re going, hmm?” Silver Wing teased. He followed after her tummy and, without warning, drilled his tongue straight into her sensitive bellybutton.
Sky Flare shrieked a giggled wail of protest and writhed against the tongue that was assaulting her.
Again, his onslaught was maintained for a full minute, before he ended it with a loving kiss on her navel. “Fourteen transgressions to go.” He whispered into her.
“I… I can’t…” Sky Flare panted out, “P-please…?” She was losing her mind. There was only so much tickling she could endure, and she was nearing her limit. Any more and she’d either faint, or pee herself. Both would be just as mortifying for her.
“Hmm.” Silver Wing mused, an air of thought about him. After a moment, he smiled at her and shrugged. “I’m not a cruel Master,” he said finally, “If you don’t want me to be gentle, I’ll oblige.”
Sky Flare gulped at his words, but before she could speak, a sharp sting raced over her marehood, forcing her to wince in pain.
“Is this more to your liking?” He asked her playfully. He swept his tail back again, then whipped it across her trembling lower lips for a second time.
Sky Flare lurched at the sensation but held her tongue. Speaking out is what had gotten her into this situation in the first place, and she had no desire to make things worse for herself.
Silver Wing whipped her marehood a few more times, then moved to her flanks, before making a final, harder swipe across her abdomen.
Sky Flare panted weakly as she hung limply from the chains. She stung where she’d been whipped, but the grin at the edges of her mouth showed her love of what had just happened to her. She loved being punished. It drove her wild. So much so, that after all that, even a gentle breeze would be enough to get her off now.
“Five transgressions to go,” He whispered into her ear. Tenderly, he began to kiss each and every spot he had just whipped, in reverse order.
Sky Flare moaned out each time his lips graced her body, then held her breath as she waited in eager anticipation for him to kiss her where he had first struck. Her marehood burned with the stinging pain his tail had left behind, but it also burned with a now unbearable desire. She needed release, now more than ever. She felt like she was on fire, and if he did not help to quell her blaze she knew she’d lose her mind.
Silver Wing knelt down before her and looked up into her pleading eyes. Grinning evilly, he leaned tantalizingly close to the eager slit, then blew ever so teasingly against it.
She felt a shiver of pleasure race up her spine, then whimpered audibly as she watched her Master move away from her again.
“Four transgressions to go.” He cooed.
Sky Flare whimpered again at his words and opened her mouth to protest, but fell silent as she felt tears of frustration and disappointment creep into her eyes. She shut her eyes tightly and dropped her head in defeat. This was it, she realized, this was her breaking point. She couldn’t take it anymore. She had to get off. She needed that sweet release of climax and if he wouldn’t do it for her now, she’d have to use her out and do it herself. She tried, but she just couldn’t take it anymore. Her safe word was the only thing that could save her now…
With a shuddered breath, Sky Flare opened her mouth to speak the word she never dreamed she’d have to use. “Rati-” she gasped in the middle of her word as she felt something hot press against her burning marehood. Looking down in confused hope, she was surprised to see a fully erect penis reaching out between her legs from behind. She looked back over her shoulder and found Silver Wing to be standing upright on his hind legs behind her.
“You make too much noise my dear,” he cooed as he wrapped his forelimbs around her in a loving embrace, “Now you’ll have to face the consequences.” Silver Wing could only take so much himself. Between Sky Flare’s reactions to his tickling, and the moaned laughter of protest his actions evicted from her sweet mouth, he’d grown harder that a steel bar. He’d known she was at her limit even before she did though, and he’d slipped behind her to wait for the exact moment she broke to strike. That’s what this lesson was all about after all, and he’d been waiting all day for this.
Sky Flare swallowed nervously and wiggled her hips ever so slightly, loving the feel of her Masters’ cock pressed up against her like this. Leaning back into him a little, she thanked those same unknown gods for her hesitation. There were few things she enjoyed more than being in her Masters’ arms like this, and she’d have savored the moment if she wasn’t so hot and pleasure starved.
Teasingly, Silver Wing slid the full length of his swollen member along his Pets’ drenched marehood and grinned as he caught her inhale sharply. Normally, he’d have teased her for that, but she’d been through enough, for now, so it was time he rewarded her for what she’d done right.
Sky Flare’s breathing grew faster as she watched her Master place his engorged tip against her burning slit and she struggled not to try and force herself down onto it. She knew that if she did that, he’d pull away and make her wait even longer for it, and she would rather endure an endless onslaught of tickling than miss the chance at having him inside her again.
Silver Wing pressed himself against her marehood ever so gently and whispered into her ear again. “Do you want me to punish you for your last four transgressions with this?” he asked heatedly.
“Mmm!” She moaned out softly at the contact, “Yes! Please! Punish me with that!”
“Very well.” he answered.
Sky Flare felt him pull away from her and whimpered in dismay. She started to look back at him, preparing to plead with him to come back, but abruptly, a thick, hot, fleshy shaft pierced straight into her and slammed against the entrance to her womb. She threw her head back and cried out in ecstasy as she was brought to orgasm from that one solitary thrust. She’d been so close before the vibrator had been removed, and despite the torment of her Masters’ tickling, and the whipping, she had stayed on the edge the entire time.
Silver Wing fought to hold back a moan of his own as Sky Flare’s already tight passage trembled and convulsed around him tighter than ever as she came against his deeply embedded cock. He’d only meant to slide about halfway into her, but she was so wet from the day of cumming against the vibrator he’d stuffed into her that he slipped right in with almost no effort at all.
“A-and who said you could cum, hmm?” He said, more shakily than he had intended.
The faintest of grins crept over the corners of Sky Flare’s mouth and she felt a victorious swell of pride rise within her at his broken tone. She may be playing the Pet, but that didn’t mean she couldn’t feel satisfied when she made her Master slip up a little.
Regaining his composure, Silver Wing pulled halfway out of his still climaxing lover and thrust into her again, holding her over the edge for as long as he could.
Sky Flare gasped out as she felt her Master start thrusting deep into her and she tensed against her chains as she was made to cum even harder.
“My my,” He teased as he looked down over her shoulder, “I can see myself from here.”
Sky Flare glanced down from her hazy plateau and grinned widely as she saw the subtle bulge in her lower abdomen. From this angle, thrusting up into her like he was, Silver’s embedded cock could be seen quite clearly as it slid in and out of her straining passage.
Never one to miss an opportunity to take things one step further, Silver Wing leaned back, then ground his nose into the ever so sensitive spot between Sky Flare’s wings, and grinned into her silken bonds as she cried out in surprise.
She couldn’t handle that. She was already cumming hard around her Masters’ delicious cock and now he was nuzzling her spine as well. It was too much for her mind, and with a final gurgled cry of ecstasy, Sky Flare felt her consciousness fade again.
Silver Wing felt her fall limp against him and chuckled. He’d loved the extra tightness her writhing around put on his dick, but he knew tickling her while mid orgasm was a short-lived pleasure. “Looks like that’s all you can take,” he said, “…For now anyways.”
Speeding up his pace, he thrust harder and deeper into his unconscious Pets’ still trembling snatch. She may have had enough, but after having listened to and witnessed such pleasured cries of agony, he needed release himself.
It didn’t take him long to reach his goal, and with a deep, guttural groan, Silver Wing drained himself deep into his Pets’ marehood. He panted against her back for a moment to catch his breath, then, with a shudder of pleasure, withdrew his still hard member from its place of rest. A thick glob of his sticky cum followed after his withdrawing tool and splattered onto the floor wetly.
Cleaning himself off with a towel that was hung nearby, Silver Wing got to work untying his exhausted Pet. The lesson was over, it’s point made. She’d earned a good long rest now. Gently, he unchained her and carried her to his bed. She’d done good, and when she awoke, he’d have a warm meal ready for her. After they ate, he’d wash her, then spend the rest of the night relaxing together by the fire. For now though…
Silver Wing returned to his sex dungeon and sighed at the mess on the floor. It’d take him quite a while to clean all this up, but it was worth it. He’d had his fun, and he knew Sky Flare had loved every minute of it.
‘She’d need to repeat this lesson a few more times before she’d be ready for lesson twelve though,’ he thought, then he paused as a grin crept over his face, ‘Then again… It might be fun to watch her fail on something really hard.’ He chuckled to himself and got to work cleaning the room, his mind already planning out their next night alone to every last detail…