Sierra's Fun (Old Classics | First-Ever Femdom Story) (Patreon)

This is a special release of my first-ever femdom story. It has for years been exclusive to Boko's patreon which is where it debuted and there's a handful of stories that similarly have never been shown on here. I've decided bringing such stories over the next few days is a fine way to celebrate the season~

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A series of slaps awoke me, though it took me some time to realize that. Before I could even form a thought, I felt a horrendous ache spreading through my entire body. My mind was in a haze, I couldn’t even begin to remember what had happened to me. All I knew was that I felt like I’d been run over by a tank.

Slowly I opened my eyes to see my own body, completely naked and covered in bruises. Disoriented, it took me a moment to realize the position I was in; my hands and feet were shackled to a wall. I was forced to stand, my arms and legs spread by tight chains. I could barely move. I was utterly helpless.

With some effort, I pulled my head up to see the girl in the room with me. There she sat, on a little wooden chair, just ten feet or so away from me. I didn’t exactly mean to, atleast not at first, but I ended up scanning her entire body.

Her long, lovely legs - both hugged by thigh-high black leggings - were crossed, just barely hiding what her short skirt would surely fail to conceal. I could already see her lengthy, voluminous hair, the unnatural yet enchanting emerald green locks flowing all the way down to her shapely ass. Her arms were crossed just beneath her generous breasts, and if I didn’t know any better I’d think she was going out of her way to prop them up.

Finally, I rested my sight on her haunting blue eyes and the innocent smile that adorned her angelic face. Even in my current state, I knew exactly who was across from me. Her name was Sierra, a veteran of the underground fighting arena. Though she hasn’t been seen in some time, I can vividly recall many a beating dished out by her tantalizing legs.

That’s when it all hit me. Through luck of the draw I had won a VIP pass to the backstage area, a dream come true for a longtime fan like me. I met many of my favorite fighters… and ended up getting demolished by them. Was that… last night? How long was I out?

“Morning, sunshine.” came Sierra’s friendly voice. “How are you feeling?”

I groaned miserably before responding, “Hurts… it hurts… please, show mercy…”

I was never much of a prideful man and what little I had was certainly stripped away by now.

“Now now, relax. I’m here to help you.” she said in an assuring tone as she hopped up from her chair. “Tell me, where are you hurting the most?”

She scanned my naked body up and down with a mischievous grin. By all rights, this was quite humiliating but luckily the ache drowned it out.

“M-My balls…” I admitted. It was true, I felt like someone had taken a sledgehammer to my crotch.

The way her face lit up when I told her this terrified me to no end. “Well that’s no surprise. After the number those girls did on you yesterday, you’re lucky to have your balls at all!” she replied with a giggle. “It’s true, the doctors juuust barely managed to save ‘em.”

The casual way she recalled my near-castration made me desperate to escape those chains. I started struggling but the more I moved, the more the pain escalated. In mere seconds, I gave up.

“Aww, calm down honey. I know exactly how to ease your suffering.”

With no more warning than that, she lunged forward and drove a toe kick into my stomach, the tip of her pump stabbing deeply into my abs.  I bolted forward as far as I could against my restraints and emitted a loud wheeze as all the air was knocked out of me.

“There we go!” Sierra chirped. “That took your mind off the pain in your nuts, right?”

Well, she wasn’t wrong. All I could focus on in that moment was this fresh new agony. She smirked proudly before putting on a surprised face.

“Oh wait…” she spoke up in mock realization. “I’ve just replaced one problem with another, haven’t I? Silly me, let me fix that...”

I tried to scream out a plea, but I couldn’t get anything out. Not that it would’ve mattered. With an amazing ferocity, she unleashed a roundhouse kick that nailed me in the cheek. The brief glimpse of her panties sadly wasn’t quite enough to dull the sting.

“That solves that!” she boasts, her fists on her hips. It was palpable how much fun she was having with this.  “Now that just leaves the matter of what to do about that pain...”

After a few seconds of apparent consideration, she puts up a finger as if she’s just had an epiphany. “Aha, I’ve got just the thing!”

Slowly, she raises her knee, pressing the top of her thigh against her stomach. I had seen this before; felt it before, and I dreaded what was coming.

“P-Please…” I begged, to no avail.

Sierra uncoiled her leg into a vicious snap kick to my already injured, bare balls. I couldn’t help but scream at the overwhelming sensation. Tauntingly she left her foot there, pressed against my battered manhood for a few seconds. I wanted so badly to curse her devilish smile, but I couldn’t form a coherent sound.

When she finally lowered her foot, she began shaking her head. “Aw man, what’s wrong with me? Now we’re right back where we started!” she said, sarcastically thumping the side of her head. “God, I’m such a ditz today.”

“S-S-Stop…!” I choked out. “Please stop…”

“Don’t worry, sweetie, we’re gonna keep going at this until we get it right!” she replied in her cheeriest tone. Her words sent a chill through my spine.

She brought up her deadly leg once more, this time going for what fans of the league call a front stomp, thrusting the sole of her heeled shoe into my stomach. This slammed me backwards against the wall. In a split second, she reared her leg back and gave another front stomp to my face. Before I could even register the pain, she withdrew it once more and this time stomped heavily into my genitals.

Much to my horror, she repeated this pattern again and again for about two straight minutes, each strike worse than the next, each one driving me into the wall. There was no other word for it, this was torture.

Finally she returned her foot to the ground, watching me writhe in seething pain. I couldn’t help but cry from the devastating assault.

“Ohhh, I know, love. It must be just awful.” she states, her voice seeped in sarcastic concern. “But let’s be honest, you have it coming to you.”

“Wh-why…?!” I cried out. “What did I do?!”

She scoffed. “Where do I start? First off, you accost Sherri, sneaking up on her and trying to spank her.”

I couldn’t help but wince at this. It was true, my hormones had gotten the best of me, but I had hoped the beating she dished out in retaliation was punishment enough.

“Then you had your lewd dealings with Filrina, I saw that one for myself.” Sierra continues.

“I mean come on, on the floor of a locker room? Where everyone can see you?”

Damn, I had forgotten she was there for that one.

“B-But she-” I spoke up, trying to defend myself, but she was quick to cut me off.

“And then there was that disgusting thing you did to Mia!” she scolded. “It’s amazing she forgave you, but I’m afraid Ms. Lin will not.”

For this I had absolutely no defense. I can only assume Selene ratted me out on that one.

“You had the privilege of meeting our fighters, some of the greatest warriors in the world, symbols of powerful females for women everywhere to look up to… and tried to make them into your sex slaves.” she scolds, shaking her head. “That’s why this is happening to you. You must be punished. And so, this is what your life will be, for the next week.”

My heart sank. “A-A-A week?!” I shrieked.

“Them’s the breaks.” she answered with a shrug.

As I was struggling to process this, she stepped up to me and began seductively caressing my chest, twiddling my nipples until they grew stiff. She then proceeded to pinch and twist them painfully.

“Arrrgh, stop, stop!” I shouted.

“Come on, we just went over this.” Sierra sighed as she brutally pulled on my nipples. “This is just what happens to perverts like you.”

“I’m not…! A pervert…!” I gasped.

She stops and stares at my crotch. She glances back up with a sly grin. “Then why is this punishment exciting you so much?”

I looked down and saw she was correct. I had grown fully erect as she was torturing my nipples. I nervously replied, “I… I just woke up a few minutes ago… it’s morning wood, that’s all!”

I was lying through my teeth and judging by her giggle, she knew that perfectly well. But she decided to play along.

“Fair enough, maybe you’re right.” she replied. “Maybe I should give you a chance.”

She gave a loving caress to my cheek down to my neck, before taking a few steps back.

“Let’s test it out, shall we?” she chirps. After a few moments of consideration, her devious grin returns. “I think I’ve got it… if you were really a pathetic pervert, a slave to your own desires, with absolutely nothing but sex on your mind at all times, then I’d probably be able to make you cum without even touching you.”

She gave me a wink that made me think she had perhaps achieved this before. “So, let’s say I tease you a little while… can you handle that? If you can go just a few minutes without losing it, then I’ll accept that you’re telling the truth and let you go.”

As hot as she was and as desperate a man as I am, this still sounded pretty easy. “Okay! Okay, I can do that!” I was quick to accept. This seemed an easy ticket out of this situation.

She seemed pleased. “Alright, just one condition: you’re not allowed to close your eyes or look away, okay? That’d be cheating.”

I nodded and a sweet smile spread across her face. “Alright, this should be fun!” she starts, as she steps to the back of the room and takes a kitchen timer from a dresser. “Okay, let’s say five minutes. We’ll see if you can last five minutes, while I do everything I can to bring you to an orgasm, without touching your little dick.”

“H-Hey!” I called back. That came out of nowhere and rather stung. I lowered my head and sadly muttered, “Mia thought it was nice...”

“Hah! She would...” Sierra muses. She sets the timer to ring in five minutes and sits it back on the dresser. She turns back to face me with her devious grin and slowly walks towards the chair, her hips sashaying skillfully. She leans over the back of the chair, giving me a wonderful look down her deep cleavage.

Within seconds, the confidence I started the challenge with had evaporated and I was already starting to get nervous.

“I’m sure you won’t mind if I get a little more… comfortable.” she purrs.

She runs her hands up her hips, hiking up her skirt. Painfully slowly, she pulls down her panties. I couldn’t help but stare agape as she twirled them on her finger, chuckling mischievously. She took them up in both hands and slingshot them towards me. 

The frilly garment bounced harmlessly against my chest and fell onto my raging erection, ending up hanging comically off the head of my penis. This earned a giggle from her and it occurred to me that this would be incredibly fun if it weren’t for my freedom being on the line.

She turns and sashays back over to the dresser and picks up a wine glass, about half-full of what I can only assume was indeed wine. I surmised that she’d perhaps been drinking it as she was waiting for me to wake up, only to lose her patience and slap me into consciousness.

As you can maybe tell, at this stage I was trying to cling to any boring thought in an attempt to distract myself. It wasn’t working.

She walked back over to the chair and sat down with her glass, twirling it like a supervillain. She crossed her legs once more and I couldn’t help but try my damnedest to get a peek between them, her womanhood just barely eluding me. She takes a sip from her glass, only to ‘accidentally’ spill a few drops onto her ample bosom.

“Whoops… silly me.” she says as she pulls out a handkerchief. She bends over quite unnecessarily as she slowly rubbed her tits dry. Even if I could’ve looked away, I wouldn’t have, I was entranced.

She had me in the palm of her hand, and she knew it. I could see it in her eyes. She held out her glass and as purposefully as could be, tipped it over to spill a little on the floor before me.

“Oh goodness, I’m such a clutz!” she lied as she stood up, sitting the glass down on the seat of the chair.

She stepped up to me, turned around and kneeled on the floor. Her skirt hiked up on it’s own, giving me a glorious view of her bare ass. In that instant I forgot where I was and got lost in the sight. As she wiped up the mess, every slight contort of her body got a moan from me.

I was locked onto her ass, unable to think of anything other than my intense desire to get inside it. I could feel my cock twitching violently, longingly. She looked back at me, her face the picture of lust.

With just three shakes of her hips, she finished me. I came and came hard, likely the second greatest orgasm of my life. I moaned loudly, this time in pure ecstasy. I was in such awe that I didn’t even notice Sierra dashing along the room to stop the timer.

She looked at it and stifled a giggle. “Wow. Two minutes and twenty-eight seconds. That’s how long you lasted. Without me ever touching you.” she said. She proceeded to stop stifling her giggling. “Hahaha, you didn’t even make it halfway! Way to go, stud!”

The blow to my ego brought back to reality. That was likely my one chance to escape this hellish week and I blew it, in more ways than one. She shakes her head as she walks back up to me, pocketing the timer. “Tsk, tsk… how sad. And look at this!”

She whips her panties off of my shrinking erection and shows them to me. My eyes widen as I realize that in my stupor, I hadn’t noticed that I came all over them.

“I… I…” I stuttered, struggling to find the words necessary to apologize for this. Before I could, she smacked me in the face with the jizz-soaked panties and I dare say that was the point I had hit rock bottom.

“Your disrespect knows no bounds.” Sierra scolds as she tosses them aside. “I’m afraid I have no choice but to tack on an extra week...”

“No…!” I begged. “You can’t do-”

I was cut off by a cheerleader-style high kick, her foot slamming up into my chin.

“Yes I can.” she stated plainly. She delivered a couple of roundhouse kicks into my ribs, one from the left, one from the right. Another front stomp to the gut was followed up by a brutal thrust kick that caught me between the eyes. I tried to savor the resulting view up her skirt, which still had nothing underneath at the moment, but the pain was just a bit too great.

I slumped hopelessly against my restraints as she stepped back to the chair. She picked up her glass and pulled the chair up closer to me, sitting down just a foot away from me. She crossed her legs once again, this time keeping them between my own. It didn’t take a genius to predict her next move; firing a snap kick into my balls.

It was gentler than her previous attacks, though certainly not delicate, and after all that my testicles had taken in the past two days, it sent a tortuous wave of anguish through my entire being all the same.

Sierra donned a smug smile as her foot bobbed up and down. Without warning she launched another stinging kick. She waited a few seconds and then, as she was taking a sip of her wine glass, jabbed my balls with her foot again. She couldn’t have been more casual in her assault, it was clear she wasn’t even trying, yet the pain brought me to tears. I’ll never forget her taunting chuckle.

Her leg flew up again and I tried to brace for it, but it stopped just short. Teasingly, she feinted like this a couple more times, just to spook me and get another laugh. She kicked once more, this time stabbing into my groin when I wasn’t even expecting it.

“Pleeeaaasse…” I groaned between sobs. “Give me another chance...”

Sierra rolled her eyes. In one motion, she leapt up to her feet and sent her knee crashing brutally into my devastated nuts. She locked eyes with me as I screamed. Slowly her smile returned.

“Okay.” she conceded. “Just to show you how merciful I am, I’ll give you a shot at retracting that extra week. But first, I’m going to need you to show some humility.”

She grabs her chair, spins it around and shoves it roughly against me. Then, to my surprise, she stands on top of it and turns around. As she takes another sip of her glass, she shoves her lovely ass into my face. She looks back at me and casually demands, “Kiss it. Kiss my ass.”

Without even a split-second of hesitation, I obeyed. I kissed each cheek passionately, as many times as I could. She seemed a tad surprised. “Heh, guess that wasn’t much of a challenge.”

She gave her butt a wiggle, grinding it into my face, before turning around. I looked up at her as she downed the last of her wine and then tossed the glass aside callously. She proceeded to take out the timer again, and declared, “Let’s see if you can match me.”

She could clearly read my confusion so she explained as she set the timer, “I brought you to an orgasm in two minutes and twenty-eight seconds. So now, we’ll find out if you’re man enough to do the same to me. I’ll even give you an advantage; you actually get to touch me to do it.”

Before I could even comprehend what she expected me to do, she shouted, “Aaaand GO!” and leapt up onto my shoulders, her thighs wrapping around my head, her exposed womanhood smothering my face. 

Fervently, desperately, I thrust my tongue into her, trying my best to please her. I couldn’t believe I had found myself in this situation again so soon. I was certainly no expert but I seemed to be doing the trick, judging by her surprised moan.

After thirty seconds or so, she brought her legs together, her thighs clamping tightly onto my head. It got quite uncomfortable but her increasing frequency of pleasured gasps motivated me, so I continued undeterred, hungrily plunging my tongue inside her.

With a passionate howl, Sierra unexpectedly dipped backwards, cranking my neck forward as she hung upside down on it. Out of nowhere, she had locked me into a submission hold and the strain on my neck was intense, but her loud, primal yells inspired me not to give up. I fought through the pain and gave it everything I had, as she seemed to glance nervously at the timer.

After a minute or so of this, she pulled herself back up onto my shoulders. “Ohhh…” she moaned.  “OHHHHHHhhh just kidding.”

I opened my eyes to see her sitting perfectly still, not making a sound. A smirk of satisfaction was on her face but it was clear this was not my doing. Suffice to say this was disheartening. She held up the timer and showed it to me, letting me know I only had ten seconds left. I worked my tongue as hard as I could, but I couldn’t even get the slightest reaction from her.

The timer started buzzing and she backflipped off of me, smoothly landing seated on the chair. She leans in, her face inches from my own.

“Not. Even. Close.” she taunted. I had never felt more utterly worthless. “You’re such a disappointment… just getting more and more pitiful by the minute. In fact, I think I’ll have to add a third week, just to make up for this.”

My head drooped in dejection. I offered no resistance. I realized now she was just going to keep doing this, and keep me here forever. And there was nothing I could do. She had broken me.

I watched her sullenly, as she hopped off the chair and stepped over to the dresser to take out a fresh pair of panties. She slowly pulled them on, and while it was a nice sight, somehow I found it depressing as well.

She walked back over to her chair and aggressively swiped it to the side.

“I think it’s about time for my workout.” she said, an intensity flashing in her eyes. “Brace yourself, lover.”

Then she let loose with a barrage of stinging, hopping kicks - speedball kicks, as those in the business call them - lighting me up all over, her feet stinging my chest, ribs, shoulders, hips. Even if I weren’t chained to the wall, I doubt I’d have any sort of answer for this onslaught. She comes in closer and unloads a couple of high kicks into my chest, before turning and running all the way to the opposite wall.

I could do nothing but stare, my heart full of dread, as she turned and dashed forward, reaching terrifying speeds before slamming her instep into my balls. Her hard shin bashed into my groin like a baseball bat with a thunderous crunch. For a moment I was certain she had obliterated my genitals, and I almost wished she had, just to spare me from any more attacks like that.

She waited for a moment just to let me linger on this fresh hell, before rushing back to the other side of the room. Once again she bolted forward at inhuman speed, her breasts bouncing wildly with every step. She then leapt forward, launching herself into a brutal dropkick that smashed me right in the face.

Somehow I stayed conscious. I cursed my bad luck. To my horror she still wasn’t done, running one last time to the opposite wall before rushing back into another dropick, this one blasting my poor balls, sending them into - and crushing them against - the wall behind me.

Sierra stood and stared at me as at this point all I was doing was trying not to throw up. She put a finger to my chin, delicately raising my head up to look her in the eye.

“Tell me what’s on your mind, love.” she purrs.

“...Kill... me…” I pleaded.

Her eyes shimmered. With a clap and a genuine smile, she responded “Great! That’s exactly what I’ve been wanting to hear!”

With that, she reaches deep into her bountiful cleavage and pulls out a small key. Then she knelt down on one knee, and to my great surprise, unhooked the shackles around my ankles.

She glanced up and saw she was at eye-level with my crotch. She gave it a playful pat, earning a pained wince from me. As she stood up, I asked, “What are you doing…?”

She giggled and responded plainly, “Unchaining you, silly.” Her face was uncomfortably close to my own, in fact she seemed to be going out of her way to press her body against mine as she undid the shackles around my wrists.

The second she freed me, I realized I had absolutely no power to stand on my own. I immediately fell, my body held up only by hers. I leaned my head against her shoulder and wrapped my arms around her to try and support myself.

“Awww, you’re so sweet!” Sierra cooed sarcastically. She wrapped her arms around me, giving me a friendly hug. Of course she finished it with a brutal squeeze that nearly crushed my ribs. After letting go, she took a step back, causing me to slide down her body and crumple to the floor. I crawled back against the wall, looking up at her in terror.

“Wh-what are you going to do to me now…?” I asked.

“Not a thing, sweetheart.” she replied as she picked up her chair and set it back down in the center of the room. She casually sat back down, leaning back in her chair. She even went so far as to take off her elbow length gloves, just so she could flippantly check her nails.

“I… I don’t understand.” I stated. I began to wonder if she’d messed my head up more than I’d realized.

Without looking at me, she responded, “I’m not sure why, but I like you. So I’m giving you one last chance.” she gestures with her head towards the door.

If someone had asked me, I would’ve told them for certain the door must’ve been locked all this time, but looking at it I realized it was actually opened a crack. I could just barge right through. Sierra continues, “If you can get past me and through that door… you’re free to go. No strings attached.”

With great effort, making a lot of use of the wall for support, I eventually got to my feet. “You… you’re kidding, right?”

“Me? Never!” she responded in faux-shock. “In fact, I’ll even give you three chances to get it done.”

I stared in disbelief. Was it even worth trying…? I couldn’t seem to muster any courage. She seemed to notice my dilemma, and spoke up, “Hey, what have you got to lose?”

With a resigned sigh, I could only concede that she was right. I took a deep exhale, and then bolted to the left of her, trying to block out the pain in my legs and put them to good use.

But Sierra displayed some truly freakish reflexes, cartwheeling out of her chair directly in front of me. With a simple hop, she forced me to run facefirst into her breasts. She wrapped her arms around me in mid-air and ended up on top of me, smothering me beneath her enormous tits. I couldn’t breathe but I didn’t struggle.

After a moment of her rubbing it in so to speak, she stood back up and dragged me over to the wall. Then she sat back down and invited me to try again. She seemed so pleased with herself, that look on her face… I wanted to punch it and kiss it in equal measure. Trying to focus on that anger, I ran to the right of her this time. Once more, she cartwheeled out of her chair, but now she stood with her back to me. She leapt up and smashed her ass into my face.

I went to the ground once again, this time with her sitting on my face. As she grinded her ass into me, I put forth no resistance. I had so little will left at this point. Sierra seemed to notice, and she wasn’t happy. She reached forward and grabbed me by the balls, squeezing and yanking at them, forcing a muffled moan out of me.

“What’s wrong with you?” she demands. “I finally give you the chance to fight back and you don’t even try?!”

She stands up, pulls me to my knees and roughly shoves me to the wall. She stands in front of me and yells, “It’s boring if you’re not even resisting! If you have even an ounce of masculinity left in you, then prove it!”

I stared into her eyes and felt a hate broiling in me. I started thinking about what she’d been doing, and got an idea. I made another mad dash, but then dove towards the ground. As I predicted, Sierra jumped for the third straight time; it seemed she had intended to smother me with her pussy again. To her surprise I ended up diving beneath her attempt.

I started crawling towards the door. She turned on a dime and grabbed for my ankles. Desperately I turned and started kicking at her. As I did, I could see that smile returning. “That’s more like it! Crushing a man who’s giving his all is much more-” I cut her off by kicking her in the face. Amazingly, this broke her grip. I stood up and hobbled towards the exit.

Unfortunately, I couldn’t compete with her speed. Within a second she had closed the distance between us and dove on me, locking her legs around my stomach. Tackling me to the ground, she quickly adjusted to lay at my side, locking me into a tight legscissors hold.

“Heheh, appreciate the effort, sweetie. But I’m afraid that was your last chance.” she taunts, as her beautiful, powerful thighs crush my ribs. “Get ready for this to be your entire existence for the next three wee-”

“Sierra!” a voice cried out from another room.

Sierra’s eyes widened. In a flash she released her brutal hold. “Coming Ms. Lin!” she called out subserviently.

She rushed to her feet and scrambled over to the dresser. She pulled out… my clothes, and threw them at me? I certainly didn’t expect that.

“Thanks for playing with me sugar, but I’m afraid that’s our cue to stop.” Sierra told me hurriedly. “Go ahead, get dressed and get out of here. Try not to let anyone see you.”

“W-Wait, what?!” I asked, shocked.

She looked at me with her mischievous smile. “Eheheh, see… I was actually playing a little trick on you this whole time.” she admitted. “Turns out, Ms. Lin expected your visit to go the way it did, more or less. She kinda figured our leagues’ fanboys would be huge perverts, so yeah. She was never actually mad, and she never actually asked me to punish you. I just took the chance to have a little fun with you.”

She reached over and instinctively I braced myself, but she simply patted me on the head. “You provided plenty of entertainment, hon.” she chirped. “Sadly, playtime’s over...”

“SIERRA!” the voice boomed louder. Frightened, Sierra bolted for the door, looking back and calling out, “No hard feelings~!” as she made her leave.

I just stood there, bewildered for a moment. Slowly I got dressed and made my way out, making sure no one saw me as I exited the mysterious building.

As I made the lonely walk home, and I recalled everything Sierra had done to me, there was just one thought that kept swirling around in my mind…

...when the hell was she getting back into the arena? And how fast could I get a ticket?