You're Anonymous, and you had no idea how you ended up in this town, let alone this technicolor pastel colored land itself. Maybe it had something to do with a bad drug trip or something? Maybe, in your 25-vodka shot inebriated state, you swam too far off the coast of your home state, Florida, into nefarious waters? The Bermuda Triangle had some pretty screwed up stories attached to it...
You couldn't complain though, because your home planet sucked pretty bad. Sure, you may have wandered around this land for a long time, and nearly starved to death twice, but you managed to stumble into a frontier town, Dodge Junction, before you keeled over and died. But in the nick of time, a very kind woman by the name of Cherry Jubilee was able to pull you into her house, and she fed and took care of you for days.
Every time she walked near you, when she wasn't busy running her cherry farm, she got this look in her eyes that only a caring mother could muster. Every little need of yours was taken care of with seemingly great joy, and whenever she walked around the house to get you things, her hips swayed...back and forth, back and forth, hypnotically. You caught yourself taking a look at her velvet red high heels more than a few times, wondering what those wonderfully cream-colored feet felt like.
That's not to say you didn't ever check out her large, curvy behind, or her rather ample bust. It's just that it was harder to see either of them with her concealing, frilly yellow dress, and the fact that she wore a pink scarf around her neck didn't help.
You felt really bad about having her wait on you like this, though, and determined that enough was enough. You weren't just going to rest on her couch, and munch on her sweet, sweet produce, reading books all day. You were determined to help her out, but you couldn't do that because it was late at night. So you planned to ask her for a job the next day.
"Lights out now, Anon, sugar...can't be havin' you missing out on your rest, now, can we?" came Cherry's quiet, soothing voice from the kitchen. She stepped out of the kitchen into the living room where you were, approaching you on the couch. You couldn't help but grin slightly up at her, as her hand stroked your hair.
"Of course, Miss Jubilee..." you murmured, blushing a bit, "may i ask you something though?" you finished. You suddenly felt the need to seem helpful right now. She shook her head, closing her eyes.
"That can wait until tomorrow, can't it, Anon? Right now, just get yer shut eye..." she replied. You felt a little disappointed, but you nodded. You were in no position to argue with her. And then up the stairs she went, out of sight. You could hear the sound of her bare soles hitting the floor as she walked on the floor above you, there was no heel sound. You only wish you managed to get a peek.
With images of what her bare feet would be like, floating around in your head, you finally managed to drift off to sleep.
You awoke to a rapidly brightening room, and a bowl of red and yellow cherries still beside you from last night. Then the smell hit you. The scent of waffles and Vanhoover-harvested maple syrup. You shot out of bed, not caring about your appearance, and rushed to the kitchen. Sure enough, Cherry was there, and she was dressed in very...form-fitting pajamas, as well as a light pink apron.
You tore your gaze away from her gentle curves, and the hypnotic movement of her behind as she walks and stretches, and tried not to notice her bare feet on the old wood floor.
"Good morning, Miss Jubilee! Do I smell what I think i smell?" you inquired. She turned around and gave you a bright, happy smile and nodded, pulling a waffle off the iron and placing it on a small plate.
"Mornin', Anon! You're right about that, it's waffles today! Now come, get it while it's hot!" she chirped, setting out places for both you and her at the antique dining table you've become familiar with. You sat down across from her, and for once, you stopped thinking about how much of a total milf she truly was.
In front of you was a single waffle, decorated in whipped cream, maple syrup, and little bits of red and yellow cherry from the ranch. Cherry Jubilee really knew the meaning of breakfast food...so you dug in with great gusto, and also a slight bit of guilt. You didn't really deserve such hospitality...it was time to ask.
Cherry stretched out her legs under the table as you opened your mouth to ask her for the job. Before you could get anything, you felt two cool, yet unbelievably smooth surfaces press against your shins. Gulping down your mouthful of waffle, you realized what those were.
Your legs tightened, and you prayed not to get too excited around her. They were so soft, they were the perfect length and width...and they were getting warmer the longer they were pressed on you. You never imagined you'd ever get to feel...them.
When Cherry was dont stretching, she grinned and retracted her legs, thankfully, none the wiser. "So, Anon, hun, you wanted to ask somethin' last night? Now that ya got your rest, you can tell me..."
When the images and feeling of Cherry's sexy soles faded from your mind (mostly), you finished up your waffle and spoke up. "Miss Jubilee...I've just been thinking. I've been here for days now, doing absolutely nothing, while you run around and manage a whole ranch, AND SOMEHOW, still attend to my every need..."
Cherry waved her hand gently, responding, "Oh, Anon, it's all fine, glad to see you safe and sound...it's just what anyone would do, ya know? So what is it, you feel better now, so you want to leave now or somethin'?"
You shook your head, and said, "No...I wanted to ask you for a job. On the ranch. I gotta repay you somehow, for all your kindness..."
Cherry seemed rather surprised. "Uhh...are ya sure about that, hun? You only just recovered...not that I'd ever turn down a hard worker..." she began, looking deep in thought. "...well, I wouldn't if we had all the help we needed 'round here, I can't afford another worker, I'm so sorry..."
Truth be told, you really didn't need to get paid for this. Being around her was enough for you. So you held out a hand and replied, "Nonsense! After all you did for me, I won't take any bits. Just tell me what I have to do, I'll do it. As long as you keep making me waffles..."
That made Cherry giggle. "Weeelll, if you're THAT hard workin', I ain't gonna deny the help...but you live here while ya work, is that fine?"
Immediately, you nodded.
"Perfect, hun. I'll get you a pair of work boots by tomorrow. For now, just kick back and relax, I got a ranch to run." Cherry ran back upstairs, out of your sight, but you managed to catch a glimpse of her...well-endowed breasts bouncing as she moved, and a short look at her plump-looking toes.
You made it a point to sleep for the entire day, as you had the next day of work ahead of you.
The next morning was the beginning of your first day of work. Cherry, in all her kindness, provided you with a sturdy pair of work boots, suited especially for kicking trees. For some reason, the denizens of this world kicked their trees to make the fruit fall into baskets, instead of picking the fruit by hand, like normal human beings.
"...and over here, finally, is the sortin' room...ya'll will be workin' the fields the first half of your shift, and the sorting the other half. My office is at the back of it, so don't you hesitate to tell ol' Cherry if something goes wrong, ok?" she explained. You were only half-paying attention, since the job seemed simple enough. Mostly, you were distracted by the sway of her hips, because you were walking behind her, and the tiny glimpses you caught of her heels. Regardless, you nodded anyways, signifying that you understood.
"Yeah...yeah, I do, Miss Jubilee, thank you..." you responded. She turned around just in time to catch your eyes on the hem of her dress, trying to look at her feet. You tore them away faster than Ponyvillians become suspicious to a newcomer, praying that she didn't actually see you ogling her.
"Weeeell, alright then, good luck to you, hun!" she said, waving goodbye and leaving you alone in front of the orchard. Unable to get the picture of her feet, pressed on your legs this morning, out of your head, you wiped some sweat off your forehead and decided to get to work.
You never really understood these people, or how things worked around here. Did the laws of physics actually apply here, or do you and your coworkers just have exceptionally powerful right legs? You'd think that you'd need to PICK the cherries out of the tree, but no, all the workers here just kicked the base of each blossoming tree with one leg, and hey presto, all the cherries fell out.
You decided to put that out of your mind, and try it yourself. And surprisingly, it worked. All of the red and yellow cherries snapped off the branches and into the baskets placed below. A grin plastered itself onto your face as you thanked yourself for never skipping leg day back home. You continued to kick those pink, blossoming cherry trees like they were your second cousin trying to steal your pony collection.
The other workers gladly offered you help whenever you needed it, which was rarely. It was quiet, the air smelled nice, and the job was a nice workout. But best of all, you were able to occasionally spot Cherry Jubilee wandering the fields, handing out glasses of ice cold yellow cherry juice.
You suddenly felt the need to take a shot every time you thought of the word 'cherry'.
But you continued your work for hours regardless, trying to be as close to your boss as possible. You could swear her eyes meet yours on occasion, and she happened to bend over a little bit every time she saw you. You tried to think nothing of it, there was no way that she KNEW you liked her. Right?
You brushed away the thoughts of her sweet, soft soles on your face, because it was time for you to move on to the second part of your shift: sorting the cherries. After taking a moment to catch your breath, you entered the front door of the factory-like structure in the middle of the ranch, having dumped your baskets laden with cherries in the back room.
There was only one other guy in the room, and he was sitting on what seemed to be a giant hamster wheel, that was connected to the conveyor belt in the middle of the floor. You suddenly had a recollection of Cherry Jubilee telling you to let him know NOT to go too fast, as she apparently had a problem with six delinquents who came into town and did exactly that. It apparently took weeks to clean the place up...
You signalled to the guy on the wheel, and he nodded, beginning his work. Cherries slowly began moving out of the back room and towards you, and you pushed the red and yellow ones into labeled barrels with ease. This really wasn't too hard of a job...and you were unwilling to ask your partner to go any faster. You didn't want to end up in a situation like those two TV stepbrothers working in a sushi factory after getting robbed.
Your boss, Cherry, then popped in through her office door. You gave her a kind nod, but then returned to focusing on your work. After all, you had no desire to let the kind lady down. But she was walking towards you, humming a soft tune, and stopped when she was directly behind you.
Cherry then leaned down, her hands softly grasping your shoulders. "Hey there, Anon...how's my favorite worker doin'?" she chirped. You began to sweat, the grip was firm, but affectionate at the same time.
"I'm...doing pretty well, Miss Jubilee...and you?" you responded, a hint of nervousness in your voice.
She whispered into your ear, "At the end of your shift...I wanna see ya in my office, y'hear?" Despite the chilling message, her words, and her breath on your neck, sent pleasurable shivers down your spine. She then pulled herself back up, and walked back to her office, looking back at you with a sultry smile...or was it evil?
You didn't know, but you had to find out.
Slowly the hours ticked by, and your entire body smelled of cherries by then, but you were finally able to finish up your shift. So you made your way directly over to Cherry's office, knocked quietly twice, and then stepped inside. You weren't sure exactly what she was going to say, but you did notice something odd.
Her cream-hued, silky feet were bare under her desk.
"Are ya gonna stand there the whole night, hun, or are ya gonna sit down and relax?" Cherry inquired, holding back a little smirk. She pointed to the seat directly in front of her, "Don'tcha worry, hun, I promise you're not in trouble."
You let out a sigh of relief, taking your eyes off her tantalising toes, and lowering yourself into the comfortable leather chair. "So...Miss Jubilee, what was it you needed?"
She leaned forward, resting her ample bust on the desk and resting her head in your hands. "Y'know, Anonymous, I wanted to see if you might be into a DIFFERENT type of work..."
"A...different type? What?" you responded, your heart racing from her naturally seductive grin, and the sight of her chest pressed up on the table.
"I saw ya workin' your hardest today, hun, and maybe your muscles might be suited to somethin' else...I'll even give you a raise if you do a good job! C'mon with me, I'll show you what you gotta do...I know ya can do it!" Cherry answered, causing your face to redden. But were you going to deny whatever she asked of you? Of course not.
She slipped her heels back on, getting up from her desk and grabbing your hand, tightly. You bit your lip and became flustered, but you followed her back to her home on the ranch. Without skipping a beat, Cherry locked her front door, walked over to her couch and beckoned you over, her beautiful eyes remaining locked to yours.
You obeyed, sitting on the other end of her rather comfortable couch. You may have imagined this happening the whole way here, but you still didn't expect what this amazingly sexy fruit farmer did next.
She reached down to her lower legs, and at a snail's pace, as if she knew how much she was teasing you, she removed her heels, and placed them neatly below her coffee table. "Ahhhh, there we go...now..." Cherry started.
She pulled her legs up onto the couch, laying on her back, and rested her curvy, lovable feet on your lap. "This'll be YOUR new job, Anonymous, hun...my poor feet gotta breathe a little...the spa is a little too far for me..." she finished, flexing her long, slender toes, and giving you a sultry wink.
You knew EXACTLY what she was asking of you. And you were going to do it.
Without hesitation, but forcing yourself to remain calm and collected, you began to knead her left foot with both your hands. Her foot was warm, and slightly slick with sweat from being kept in a set of high heels all day. Your thumbs rolling around in the immensely soft flesh of her arch felt like heaven to you, but you could sense how delicate her feet were. So you made sure to take extra good care of them.
She let out a quiet moan, grinning and flexing her slender toes as your fingers gently worked their way up to the ball of her left sole. Cherry's right foot, however, wasn't getting any sort of attention, and began to wander a little...you didn't notice it, though, until the unattended sole came to rest on the tent pitched in your trousers.
You couldn't help yourself and let out a pleasured groan, your hands accidentally squeezing her fragile left foot too hard. But instead of hurting your boss, you actually made her moan in relief, much louder than last time.
"Mmmmm, that's it, Anon, you can be a lil' more firm than that...remember that 'raise' I promised ya if you do a nice job..." Cherry cooed, her delectable right foot continuing to tease you through your pants. To further motivate you, she crossed her arms beneath her large, bouncy breasts, defining them just a little more for you to see.
And it worked wonders on you. Now, your hands were moulding around her left foot, like it was a firm batch of pastry dough. You slid your fingers between all of her tight toe spaces, dragging them outwards, the tips of your fingers sliding down her curved arch, all the way down to her heel.
With a little giggle from her at the ticklish sensation, and a few final squeezes from both of your hands, you reluctantly let go of her left foot. You also made sure to give each toe an affectionate 'farewell' kiss. Now, the opposite needed to be tended to. Cherry then offered you her right foot, the big toe soaked in precum because of the teasing her foot had done to you earlier.
There were no hesitations in your mind now, you'd simply gone too far to disappoint your boss now. You held her soft, pleasantly warm right foot like you owned it, making sure to press your thumbs into every little nook and cranny of her sexy, enticing sole. Meanwhile, her cared-for left foot continued to keep your bulge occupied, but this time, down went your zipper between her graceful big and second toe, and she dug into the little crevice with both of those digits and teased you through one less layer of clothing. This only made you more hot and heavy, and made it harder to focus on the massage.
You clenched your teeth, but didn't dare to close your eyes and relax. You had a job to do. Back and forth you pulled each one of her adorable toes, listening to her angelic moans as each one of them loosened and cracked. When you finished that, you worked your hands down under her toes, and then squeezed her upper sole while running the back of your hand up and down the gentle curve of her arch. You couldn't live with yourself if you hadn't felt how divinely smooth that was, with her foot fully stretched out.
With two more firm, but loving, squeezes to the arch, and five more kisses to her lovely toes, you were finished with the massage. Judging by the blush on her face that was almost the color of her hair, and the relieved grin, you could tell you did a wonderful job. And that was what she deserved.
"Mmmmhhh, I haven't felt a massage like that...in years, hun...I really needed that..." Cherry sighed, curling her left set of toes on your member through your boxer shorts. You clenched your fists and bit your lip, trying to refrain from taking them right then and there.
"But I did promise you a lil' raise, and I'm gonna do that right now...just bear with me, yer lil' friend'll feel good again soon..." she murmured. She then took her silky sole away from your length, and you could practically HEAR it cry out in protest. But Cherry wasn't about to disappoint you.
She pushed herself up off the couch, and gave you the sexiest wink you'd ever seen. "Anon, I could use a little help here..." she called out to you, pointing to the zipper in the back of her gown. You immediately obliged, pulling it down fully, so she was able to slip it off her body, allowing her defined, yet still soft, curves be seen, much more clearly than when she wore her pajamas.
Cherry tossed her gown across the room, walking towards you, and swaying her bare body in quite a sultry manner. She had absolutely no bra or panties underneath that dress, and that just made her all the more delicious-looking. Her breasts, easily a D size, bounced in the most inviting way as she walked, her wide, defined backside made the slightest sound of silk rubbing together. You also noticed her nethers were glistening wet, and she was biting her lower lip. While you did admire the rest of her grope-worthy body, both you and her knew that there was one thing you truly wanted.
And she sat back down, rubbing her precious, curvy soles together, and placed them on either side of your cock, still constricted by your undergarments.
You threw your head back and let out a strained groan of pleasure, but concentrated on holding yourself back. It would’ve been incredibly impolite to just blow it on her peds right then and there, and it would have also cut your hot, sexy ‘raise’ way too short.
Your boss grabbed both your pants and your boxers at the same time, using her flexible toes, and pulled both garments down to allow your heavily-leaking length to spring out, so she could do her work.
Suddenly, you had an enormous explosion of pleasure run through your entire body, as you were able to feel her silky smooth, naked feet hug your bare member for the very first time. The fact that her soles were blushing slightly from the love they received earlier made it all the more sexy.
It was like the soft curvature of her beautiful feet was made especially to fit you between them. Her soles glided expertly up and down the sides of your twitching cock, in opposite directions. One sole made its way upwards, collecting the precut from your tip, and the other foot slid downwards, pressing firmly on the base of it.
“W-why…did I not come here earlier…” you stuttered, as Cherry’s left set of toes began to fondle and squeeze your sack. Her right foot worked its way to your upper member, the big toe pressing down on the tip. This caused you to shudder and spurt a little on her smooth toe. She giggled a little at the warm, sticky feeling and made sure to continue circling your tip with the toe.
You couldn’t hold yourself back much longer. The longer she stroked you off between her up to your tip, the more you leaked pre. The more you leaked, the easier it became to slide her soles up and down. And the easier it was to slide her feet up and down…the closer you came to unloading.
But Cherry wasn’t just about to let this end without you feeling her love from other parts of her feet. She positioned herself so she could hold your cock tightly between the top of her left foot, and the sole of her right. She continued to run her slick, sexy sole up and down your member faster, with more passion.
You gasped and started to pant erratically, laying back and tensing yourself as hard as you could, so you could enjoy being hugged between her angelic feet for even a second longer.
Cherry glanced down at your length, then batted her eyelashes seductively at you. “Aw, c’mon now, hun, don’t be holdin’ out on me…” she cooed, tracing the tips of her toes along your shaft, forcing you to grow more painfully hard than you ever have before.
She quickly returned both of her soles to the sides of your member, holding them in a vertical position so every inch of your as engulfed in their snug, heavenly warmth. You finally lost control and let out a grunt, bucking your hips and unloaded all over her silky, tender soles, the white fluid spurting upwards, and then raining down on her curvy, sexy soles, which were massaging you the whole way through your intense orgasm.
“Theeeere ya go, hun…how’d you enjoy your raise?” Cherry said, as you calmed yourself down out of your blissful orgasmic high. You weakly pushed yourself up and gave her a small smile, nodding, and catching your breath.
“Now that you got yer new job, hun, I think it’s time we upgrade your sleeping arrangements…come on with me…” she whispered, beckoning you along. Not bothering to redress yourself, you followed behind your boss, keeping your hands on her squishy, wide hips. She giggled as she reached her bedroom, pointing to her luxurious four-poster bed.
“That’s where you sleep now, Anon…now come get your rest, ya hear? I know yer gonna need it for tomorrow…I got a LOOONG massage I’m expectin’…” Cherry said to you, giving you her signature bedroom wink.
“….And if you do a good job…I think I can arrange a lil’ ‘raise’ for you when I got the chance…sound good, hun?”
Of course it did.
You threw off your work shirt, because it would be rude to Cherry if you were clothed, and she was not. You then pulled your soft, sexy boss into bed with you. Since she obviously wasn’t as tired as you, she brought a pillow with her and laid her head at the foot of the bed, reading a book. But she didn’t forget you, because she pressed both of her amazing soles back into the sides of your member, giving you a warm, safe and happy feeling. You just had to close your eyes and take a long rest…Cherry was counting on you to ease her tension. Would you want to let her down?
-End
Author's Note
Once again, I wanna thank daba zaba for this idea. It was sexy as hell, and it took me way longer than I liked. But it's done!
