Principal Celestia's Anal Training
Cheerilee pulled into Principal Celestia’s driveway, her panties already soaking wet. She couldn’t stop thinking about all the kinky things that she was going to make her submissive lover do tonight. She had to drive a lot slower than usual, though, for it had started snowing late last night, and the dark clouds above showed no signs of letting up anytime soon. She sighed in relief, happy that she was able to get to her secret lover’s home without having an accident. Putting the car in park, she turned it off and tightened the scarf around her neck. She enjoyed the heat for just another few seconds, then opened the door. The icy wind bit into her exposed skin, sapping away her warmth. She wrapped her arms under her breasts as she hurried up the path to Celestia’s front door. “The things I do to get some release...” she muttered to herself as she nearly slipped on the way up, a small grin tugging the ends of her lips upwards.
Now standing on the front porch, she thought to just open the door and walk right in, but she felt that doing such a thing wouldn’t be that proper. She knew she’d hate it if someone did that at her house, so she raised her fist and insistently rapped on the door. About a month ago, Celestia had come by her classroom and had found her exasperated, her papers to grade overflowing. She’d worked herself to the limit, and Celestia had noticed that immediately. Even though she had assured her boss that everything was okay and that she could handle it, Celestia nevertheless sat down and helped her, something she thought that a principal would never do. She appreciated the kind gesture, and offered to take her out for a dinner, and afterwards, Celestia had tentatively offered her a different kind of release from her stressful job.
This was going to be the third weekend in a row that she’d slept over at Principal Celestia’s, and the last time she’d answered the door, Celestia had been wearing a light pink thong and a matching see-through negligee that barely gave any support to her large breasts. Cheerilee had to keep herself from pouncing on her the moment the door swung open, and she wondered what Celestia was wearing to greet her on such a cold night.
The front door swung open wide, the house’s warmth flowing out and banishing the cold away. Celestia was wearing a pair of red high-heels, a pair that Cheerilee recognized as the ones that she’d left behind last weekend, to be exact. As a smirk grew on her face, Cheerilee took in Celestia’s toned legs as her eyes swung upward, spotting her favorite silky white thong, her puffy lips just barely hidden by the floral pattern.
Flicking her gaze higher still, Cheerilee noticed her wearing a matching push-up bra, and as her eyes slipped up to meet Celestia’s gaze, she saw her reaching out for her. With a small blush, she felt Celestia’s fingers intertwine between her own as she pulled her in from the wintery cold. “I see that you’re properly attired, little one,” she murmured with a grin, her hand slipping from Celestia’s as she stepped aside. Cheerilee pulled her gloves off, tossed them on the small table right next to the door, kicked off her shoes, then turned around to find Celestia’s ass on full display to her as she tried to close the door. “Aren’t you afraid of someone seeing you like this? It’s nice to see you all dressed up for me, but I wouldn’t want you to cause problems with your neighbors,” she said with a giggle, her eyes locked on Celestia’s spankable butt. “But I bet you want them to see you like this, though.”
As Celestia tried to push away the carpet that somehow got in the way of the door, Cheerilee grabbed her submissive’s ass and shook it. “Still as beautiful as always...” she murmured, letting her fingers drift closer and closer to her panties. “Oh, and what might this be?” she asked, cocking her head to the side as the tips of her fingers brushed against something rubbery. “Don’t you remember that only I can give you pleasure?” She pulled Celestia’s panties aside and noticed a thick butt plug, one of the sex toys that she had purchased for her new submissive’s training. Celestia had made very significant progress over the past few weeks, going from barely able to take a couple fingers to butt plugs slightly larger than her fist.
Cheerilee was more than pleased at that fact, for she had something oh-so-intoxicating in mind for tonight.
“Oh, I am not wearing this for pleasure, Mistress!” Celestia stammered, her voice filled with worry as she pushed the door the rest of the way shut. “I only did it so that we could maybe go straight to the big toys right away, and I... I got a new toy for us to play with.” She tried to stand back up, but felt an insistent hand upon her shoulder. Celestia glanced up for a moment, then knelt back down as she wondered what her Mistress had in store for her.
“Glad to hear it...” With a naughty grin, Cheerilee knelt down behind her submissive and placed a hand on the small of her back, applying a little bit of pressure. When Celestia pushed her ass up, already well-familiar with her silent command, she grabbed the base of the butt plug and wiggled it around, keeping her thumb pressed on the flimsy G-string to keep it from slipping off of the toy. “I see you’ve been a naughty girl... Taking one of the biggest butt plugs we have to keep your ass nice and stretched for me...” She slapped Celestia’s butt, making her cry out with a muffled squeal of shock. She loved those cute sounds she made, so as her grin deepened, she slapped her ass again, right on the same spot. “How long have you kept this one in, cutie?” she asked, once again wrapping her hand around the sex toy.
“A-An hour, Mistress,” Celestia admitted with a blush. “And I have been practicing all week, too! I managed to get up to this size two nights ago, and I even wore my medium-sized one to school yesterday so that I can show you just how far I have gotten! Also, I got that new toy in the mail today, and it is far too big for me to take without some proper stretching. I thought that maybe...” She stood up and turned around, pressing Cheerilee up against the wall. Looping her right leg behind her Mistress’s left leg, Celestia leaned in and whispered, “You could help stretch me out... down there...” She unzipped Cheerilee’s jacket, wrapped her fingers around the collar, then yanked it down, pinning her lover’s arms to her sides. Celestia leaned in, her lips a hair’s length away from Cheerilee’s lips. Her eyes drifted shut, and as she tilted her head to the side ever so slightly, she gently stole a kiss from her lover’s soft, tender lips. She pulled back, biting her bottom lip as she gazed into Cheerilee’s eyes. “I am sorry for being so forward, I just...”
“Need to be punished, that’s what!” Cheerilee said as she tossed her jacket on the floor. “Get on your hands and knees, my pet...” she said in a low, commanding voice. She felt her nipples harden through her bra, and as she glanced down, she noticed them poking through her shirt. With a light chuckle, she placed her car keys down on the small table, then slipped a hand up her shirt and into her bra. Her nimble fingers found her perky nipple, which she squeezed tightly. Feeling a little more of her arousal drip into her panties, she groped her breast a couple of times, then opened up the drawer and pulled out a slim riding crop, thoughts of her submissive’s mouth on her nipples driving her wild with passion and lust. In time... She turned back around and found Celestia presenting again, just the way she liked. Her head was flat on the floor, resting upon her hands as her ass was pushed up into the air, her legs spread wide.
Cheerilee knelt down behind her, then placed the tip of the riding crop on Celestia’s pussy. She drew small circles right where her clitoris was, making her submissive’s legs tremble. “Tell me... what size butt plug is this?”
“Extra large, ma’am,” Celestia said, biting back a moan as she felt her silk thong slip between her puffy labia. A single drop of arousal dripped from her folds, only to be soaked up by her panties. Her heart raced in her chest, and her breaths came in short pants.
“I see... And you worked your way up from the small one as soon as you got home from school?”
“Actually, I started on the medium one, Mistress. I think the small one is not necessary anymore.” Celestia nearly whimpered as the riding crop disappeared from her clitoris, nearly wishing to feel its wonderful touch once more.
“Good... Your ass is getting used to my training, isn’t it...” Cheerilee whispered, leaning in close. She wrapped her fingers around the base of Celestia’s butt plug and gently pulled on it, watching her ring expand as the thick part of the toy started to slip out. “Let me know if it’s starting to feel too much, little one,” she said, laying a kiss on Celestia’s right butt cheek.
“I am... fine,” Celestia said, forcing herself to relax. A little more of the butt plug slipped out, almost nearing the thickest part. As it finally reached that part, she felt Cheerilee pause. She glanced over her shoulder and saw a wicked grin upon her face, making her blush deepen. “What is it, Mistress?”
“I want you to clench down as hard as you can, right here, and walk on your hands and knees onto the bed,” Cheerilee said as she stood up, once again laying the tip of the riding crop against her sub’s pussy. “If I see it slip in or out, you’ll be in trouble.”
“Yes, Mistress,” Celestia murmured as she took a single step, letting the riding crop guide her forward. The butt plug, despite her best efforts, started to slip back inside, so she paused and pushed it back out, just a bit. With her vision starting to blur from sheer pleasure, Celestia slowly lifted her right hand and left leg and took a trembling step towards her nearby bedroom door. Good thing I don’t have stairs in my home... I’d hate to try to walk upstairs like this! She turned the corner, going as slow as a turtle, and right before her left hand touched the bed, her thong pushed the butt plug all the way back inside of her.
“Tsk tsk...” Cheerilee said as she shook her head. “Couldn’t do it, huh?”
“B-But Mistress!” Celestia pushed herself up, sitting on her folded legs as she shot a pleading gaze up at Mistress. “I made it to the bed like you asked!”
“I wanted you to get up on the bed, not sit in front of it.” She nodded at the bed. “Now go ahead, climb up and assume the position so I can administer your punishment.”
“Y-Yes, Mistress...” Did she really say onto the bed? I do not remember her saying that, though... Celestia bit her bottom lip, but did as was ordered, her shoulders slumping from disappointing Mistress. With her feet hanging off of the bed, she pulled a pillow from the head of the bed and laid her head down upon it. She spread her legs wide, though before she could get in the proper position, Mistress pushed her forward, making her fall flat. She rolled over just in time for Mistress to straddle her hips.
Cheerilee gazed down upon her softly panting submissive with a smirk. “Take off your bra; we shall not be needing it anymore.”
“Yes, Mistress.” Celestia pushed her hands behind her back and unclasped her bra as her mistress grinded on her hips. She tossed it aside, her breasts now on full display. Celestia felt her cheeks warm up as she looked around, anywhere but Mistress’s piercing gaze, then finally settled on Mistress’s breasts. Though while the blessing of seeing such perfect breasts wasn’t allowed right now, she prayed for a chance to see her lover’s naked body. She thought back to when they had started their dominant and submissive relationship to the point where she had seen Cheerilee fully unclothed for the first time. Her bountiful breasts had glimmered in the light, free of any blemishes and imperfections. Her nipples, perky and standing proud, made her mouth water at the thought of being given the gift of feeling them upon her lips once more.
Waiting an entire week was much too long for Celestia.
“So... where is this new toy that you spoke of?” Cheerilee asked, running a single finger down between Celestia’s breasts before she squeezed the base of her beasts.
“Right here, Mistress!” Celestia said with glee. She reached underneath a pillow and pulled it out, holding it to her with both hands, blushing furiously.
“And what might this be, hm?” Cheerilee asked, lifting it from her submissive’s hands. She couldn’t even wrap her hand all the way around the massive toy. It had a flat head, a thick medial ring with small bumps, and a set of straps meant for the giver. It was almost as long as her forearm, and was a little bit thicker than it.
“The biggest strap-on I could find online, Mistress,” Celestia murmured, already soaked at the thought of her being bent over the bed and fucked with her new toy. Her heart raced in her chest as she felt her arousal slip from her folds and down her butt-crack.
“Yes, I can see that, but why did you buy it?” Cheerilee asked, squeezing the new toy.
“Because I wanted you to fuck me with it,” Celestia murmured, biting her bottom lip as she gazed up into her lover’s eyes.
“Is that so? Well, I don’t think you’re ready for a toy this thick, little one,” Cheerilee said, running her hand through Celestia’s hair.
“But I am, I promise!” Celestia said indignantly, pushing herself up on her elbows. “That was why I was wearing this butt plug all day!”
“Well... we would have to stretch you out...” She lifted her arm up, then threw on a sly grin. “I think a good fisting will help loosen you up.” Cheerilee pushed herself up, still holding the strap-on. “Assume the position, you slut, and I’ll get ready...” She set the toy down on the bed and went to her submissive’s nightstand. Pulling open the top drawer, she observed the wide array of toys that she had at her disposal. Choosing her favorite one, she grabbed a light pink vibrating dildo with a thick knot at the base, designed to keep the toy inside once the knot was fully seated. With a smirk, she turned back around and found Celestia’s ass on full display for her, the butt plug sticking out like a sore thumb. “Let’s start with something easy, hm?” she asked, coating the dildo with her lover’s arousal.
“Huh?” Celestia managed to ask before the dildo slid inside of her, making her give a long, throaty moan. “Oh, Mistress...” she groaned, pushing back on the toy. “You know how to make me feel so good... I really don’t know what I would do without you...” She shot a loving smile over her shoulders, only to have the knot press up against her softly-throbbing slit.
“I’m glad to hear that, little one...” Cheerilee slapped Celestia’s ass as hard as she could, making her lover clamp down on the toy as her legs trembled. She rubbed the spot that she’d just hit, then whispered, “Be a good slut for Mistress and I’ll make sure you cum so hard you’ll be dehydrated from squirting so much...”
“Y-Yes, Mistress!” Celestia said, her breaths coming in short and fast. She made her pussy’s muscles relax, then pushed herself back, taking the knot bit by bit until she nearly reached the thickest part. She took a few deep breaths and tried again, but still couldn’t achieve her goal. Her heart dropped into her stomach at the thought of failing her Mistress’ wishes. “Um... I... I...” she stuttered, unable to form a coherent sentence.
“Don’t worry, I’ll help.” Cheerilee turned the vibrator on and twisted the toy from side to side, gently working it deeper inside of her lover until the knot disappeared inside of her pussy. “There you go...” she cooed. “Such a good girl... Taking that thick knot like a bitch in heat...” She slapped Celestia’s other cheek, then gently rubbed her clitoris with a finger, drawing small circles on it.
“T-Thank you, Mistress!” Celestia panted, her legs quivering from sheer pleasure. Her heart soared, for the knowledge that she had such a caring and tender Mistress gave her much pleasure, especially now that she’d taken the entirety of the toy. The knot pressed right up against her G-spot, and the tip of the toy brushed a couple of centimeters away from her cervix if she bucked her hips the right way, sending small tingles of electrical pleasure all throughout her body. “Eeep!” she squealed, suddenly feeling Mistress’ lips and tongue caress her throbbing clitoris. “Unh...” Her vision went blurry as she felt herself grow close to the edge of an orgasm, but moments before she squirted all over her lover’s face, she felt Mistress pull away, her little love button dripping with her warm saliva. “M-Mistress...” she whined, bucking her hips back. “I was so close...”
“Heh, yeah, I know. Your toes curl up in the cutest of ways when you’re about to cum.”
“...Oh. Really?”
“Mhm.” Cheerilee grabbed the base of the butt plug and gently worked it out of her. With her hole gaping, she grabbed a bottle of lube from the drawer and squirted no small amount in the slowly-closing hole. “That feel good, you slut? You like feeling me squirt lube into your asshole?”
“I think that it would feel better if I had your arm in me,” Celestia said without thinking, a small smirk on her face. A moment later, her left butt cheek exploded in pain, making her eyes go wide. She gasped softly, clenching down on the vibrator within her. Her ass felt rather empty, a fact that made her disappointed, but the fact that she was about to get fisted pushed those depressing thoughts away. “I am sorry, Mistress, please forgive me!” she said, praying that Mistress wouldn’t withhold pleasure.
Cheerilee waited a few moments for dramatic effect, then sighed. “Very well, but another outburst like that will mean edging with no orgasms for the rest of the night. If you do manage to cum, then I’ll make you wear a chastity belt until the next time I come over. I know how much you like to play with yourself after work, so ensuring that you won’t be able to cum for an entire week would be a suitable punishment. So do you promise to be a good slut for me?”
“Yes, Mistress!” Celestia said, her shoulders drooping in relief.
“Good.” She dripped some lube onto her right hand, then spread it halfway up her forearm with her left. She smiled as the tips of her fingers brushed against her submissive’s puckered ring, taking pleasure in how soft it was. She spit on it, watching as her saliva slowly dripped into her still-open hole. Running a single finger around the rim, she slid four fingers inside of her, spread them out, then pulled her hand out, stretching her lover’s hole little by little with each insertion. “You ready, my love?”
“Yes...” Celestia panted, her head buried in her arms.
“Yes, what?” Cheerilee asked, her tone low as she stretched her submissive’s hole with her thumbs.
“Yes, Mistress!” Celestia said, her voice muffled by the sheets.
“Excellent...” Cheerilee purred, forming a fist with her hand. She placed it against Celestia’s ring, then pushed it inside. Her submissive instantly clamped down on her fist as she let loose a low, throaty moan. “Hm...” She glanced down at Celestia’s toes and noticed that they were curled up tight. With her eyes going wide, she turned the vibrator to its lowest setting, waited ten seconds, then when her toes relaxed, Cheerilee slowly worked her fist inside of her. She felt the knot of the vibrator through her ass, spending a few seconds there as she worked her arm back and forth, gently thrusting in and out of her. Her submissive’s puckered ring clamped down on her arm whenever she let her fist relax, letting her fingers explore her insides and pushing against the toy in her pussy. Knowing that Celestia would need further stretching, she started fucking her with her arm and fist, making lube splatter all across her shirt and on Celestia’s ass from her fast, fervent pace.
Celestia’s vision went blurry again as she moaned like a true bitch in heat. Every time that Mistress’ arm plunged deep inside of her, she felt as if everything was as it should be. She was under Mistress’ control, and that fact alone made her feel content, and the knowledge that Mistress would tend to her needs after their session made her heart swell with joy. She’d never felt so trusting of someone else before. To give someone else full control of yourself, to let them tease you and play with your body and mind in ways unthinkable, and to make you cum in ways unimaginable told Celestia that she had found a keeper, someone she could share her life with. Although, when Mistress was gone, Celestia found herself fantasizing about her several times a day, more often than not leaving her panties a little wet. The thought to ask her to move in with her crossed her mind, making her pussy leak more of her arousal around the tight seal of the knot, but they were still so early in their relationship that she feared that such a question would scare Mistress off. Such an important and life-changing question would surely have to wait.
Besides, it’d be nice to have someone to fuck you every night to blow off some steam.
Celestia’s tongue slipped from her mouth as she panted, her vision still blurry. Her lover’s fist slowed down, then stopped altogether, her ass feeling particularly full, just how she loved it.
“There we go... I think that’s good enough,” Cheerilee pushed her arm as deep as it could go, then spread her fingers wide. She pulled her tired and sore arm out of her submissive’s ass with a loud ‘plop’, then wiped it down with one of the towels that lay on Celestia’s nightstand. Tossing it aside, she switched the vibrator off in her submissive’s sopping wet pussy, then said, “Be a good slut and relax so I can work this thick knot out of you...” With her clean hand, she pushed her fingers inside of Celestia’s pussy, working them around the toy’s knot. “There we go...” she murmured as she slowly pulled the pink vibrator from her dripping cunt. Cheerilee leaned in, took a deep whiff of her heady scent, then lapped at her slit with her tongue until she had licked up all of her arousal. “I think I’ll go wash my arm in the bathroom, little one. I’ll be right back, okay?” She walked from the room and down the hall, then into the bathroom. She turned on the faucet, and right as she finished cleaning off her arm, she heard a soft ‘ahem’ behind her. Cheerilee looked over her shoulder and found Celestia on her knees, sitting on her legs with her hands in her lap, holding a slim, silver vibrator. “Something wrong?” she asked, cocking her head to the side.
“No, of course not! Well...” She bit her lip and glanced away, wondering if she should speak the words that danced on the tip of her tongue. “I, um... I don’t think it’s fair that I’ve gotten all the pleasure so far, so could you, um...” She blushed furiously as she wondered if it was proper to ask such a question to Mistress. “Could you maybe let me pull your pants down and eat you out until you cum? Please?” she asked, looking up at her with a hopeful and shy smile.
Cheerilee was taken aback at this. “Oh! Uh... very well, then,” she said, letting a soft smile slide onto her face. This one’s a keeper! she thought, propping herself up on the sink with her elbows. She leaned over and pushed her butt up, felt her submissive’s slightly ticklish fingers undo her belt, then finally felt her pants slide down her legs to rest upon her ankles. She stepped out of them, then kicked them off to the side. “You remember these panties?” she asked softly, feeling her cheeks warm up with a soft blush. “They’re yours. I didn’t bring over any clean ones last weekend, and I kinda needed some after how we ruined my last pair. All of that lube...” She felt a shiver run up her back as Celestia slowly and tenderly pulled her panties down.
“Would it please you if I asked you to keep these? These cute purple hipsters sure do make your butt look good...” Celestia licked her lips as she eyed the crotch of what used to be her panties. It was simply soaked through with her Mistress’ arousal, making the crotch look a deeper shade of purple.
“I think I might need to borrow another pair, if you don’t mind,” Cheerilee said, hearing Celestia scootch up closer.
“Oh, you can borrow as many panties as you like, so long as you come back wearing them... I think it’s hot to see you wearing my panties, by the way.” She licked her old panties clean of Cheerilee’s arousal, then licked her lips clean as her gaze shifted to her prize. Her grin deepened as she wrapped her hands around her lover’s hips, pulling her ass right into her face. She found her sopping wet pussy with her mouth in an instant, then used her left hand to turn on the vibrator that was held in her right hand. Celestia pushed the vibrator against her lover’s clitoris, and when she heard Mistress moan, she plunged her tongue inside of her, licking as fast as she could.
With Mistress’ arousal dripping down her face, Celestia couldn’t help but feel her heart swell with joy. Nobody else had been able to make her feel this way, used, but loved at the same time. With that thought firmly planted in her mind, she lapped at Mistress’ slit with a renewed vigor, feeling every single little twitch that ran down Mistress’ legs. Knowing that she was getting close, she stood up and kept the vibrator pressed firmly against her lover’s clitoris. She pressed herself against Mistress’ back, then used her left hand to pull her hips into her own. With her lips still wet with Mistress’ arousal, she planted a soft and tender kiss just under her right ear, nuzzling away her hair as she gazed into her eyes in the mirror. “You getting close?” she whispered, fingering Mistress’ dripping wet cunt with her left hand. “I want you to cum for me...”
“Nnggh... I’m so close, but... I need something more, please!” Cheerilee begged, her eyes clenched shut. She bucked her hips back into her submissive’s, the vibrator never leaving her clitoris. “P-Please!” she begged, staring into her lover’s eyes through the mirror with a pleading gaze.
Celestia let a soft smile slip on her face as she laid her head on her shoulder, her eyes never leaving Cheerilee’s. “I love you,” she whispered tentatively, slipping a hand up Cheerilee’s shirt, praying that her first utterance of such a powerful phrase would land on accepting ears. She pushed aside Mistress’ bra and groped her right breast, her hand soaked with her arousal, then teased her nipples with the tips of her fingers as she gently nibbled on Cheerilee’s ear lobe.
She... She loves me? Cheerilee’s eyes drifted shut as she finally neared the edge, a soft smile on her face. “Oh... Oh... I’m I-I... I think I’m gonna... Celestiaaaa!” she cried out in sweet bliss, throwing her head back.
Celestia cupped her hands underneath her lover’s slit a moment before she started squirting. She watched on breathlessly with wide eyes as she collected a small pool of her lover’s cum, the sweet-smelling liquid shimmering in the bathroom’s light. “Mistress? May I?” she asked, her lips still smeared with Cheerilee’s arousal.
“Yes, you may...” Cheerilee murmured, turning around to prop herself up on the sink as she reached into her bra, placing her breasts back into the cups. She grinned as she watched Celestia drink her cum as if it was the elixir of life, then when she could drink no more, she smeared what was left on her breasts. “Heh, you’re such a cute slut. You know that, right?”
Celestia beamed up at Mistress. “Shall we get back to the bedroom?”
“Yes, I think we shall, though I require you to remove my shirt. No point in wearing it since we’re gonna get dirty later on,” she said with a smirk as sweat dripped down her brow. She put her arms up as Celestia reached for the hem of her shirt. Cheerilee felt her lover’s warm breath tease her lips as she leaned in close, tugging the shirt from her body.
Letting it fall to the floor, Celestia couldn’t resist the urge to let her gaze slip down to Cheerilee’s bra. Her mouth formed a small ‘O’ as her breasts glimmered in the light, slightly sweaty from her orgasm, encapsulated in a purple lacy, see-through bra. Her nipples were rock-hard, standing at attention and begging to be tended to. Celestia flicked her eyes back up to silently plead with Mistress as she licked her lips, her gaze going back and forth from her beautiful face to her bountiful breasts.
“Oh, very well,” Cheerilee murmured, running her fingers through her submissive’s hair. She reached up to her bra’s straps, then let them slip from her shoulders, partially-revealing her nipples to the slightly-cold air.
When Cheerilee nodded, giving her consent, Celestia dove right on in, wrapping her lips around Mistress’ right nipple as she used one of her hands to massage, squeeze, and play with her other breast, letting her other hand drift down to Mistress’ rear end. She flicked her nipple every which way with her tongue as she suckled on it. Even though she knew that her lover’s breasts weren’t producing any milk, the mere thought of drinking from her breasts made her cheeks flush, for she considered it just as naughty as drinking her lover’s cum. With a tinge of regret, she let go, holding her hands in front of her with her head bowed. “Does Mistress wish to return to the bedroom to play with me now?”
“Yes, I think that is a swell idea,” Cheerilee said, planting a soft peck on Celestia’s cheek. She took her by the hand and led her back to the bedroom and kicked the door shut behind them. Cheerilee let a sly grin slip on her face as she pushed Celestia onto the bed, making her land on her hands and knees. “Come to the edge of the bed, little one,” she said, pointing at where she wanted her submissive to be.
“Yes, Mistress!” Celestia backed up, letting her feet dangle over the edge. She looked over her shoulder as she watched Mistress tighten the strap-on onto her groin. “If you look at the top of the strap, Mistress, there is a little switch that will give us both pleasure. I got the upgraded model,” she said, feeling herself blush once more.
“Oh? And what might that mean?”
“Well...” Celestia licked her lips as she spread her legs, the tips of her nipples brushing against the sheets. “It has two very strong vibrators, one at the tip of the toy, and one at the base. If you turn it on, you’ll see what I mean. The store I bought it from says that it helps when you’re trying to insert it into your loved one, so...” She wiggled her butt and used her fingers to spread her butt cheeks apart, revealing the fact that she had inserted the large butt plug from before.
“Very well, then.” Cheerilee grabbed the base of the dildo and swatted the flat part of the butt plug, then rubbed its length along Celestia’s slit, getting the toy all nice and wet with her arousal. She wrapped her fingers around the butt plug’s base, then before she pulled it out, she said, “Make sure you try to hold it in for as long as possible, my little slut. We gotta make sure that you stay nice and stretched out if you’re going to take the full length of my new toy!”
“Y-Yes, Mistress!” Celestia panted, wishing that Mistress would hurry up. All of this teasing was driving her wild with an animalistic lust, especially with how the bumpy medial ring of the dildo teased her slit as it slid back and forth across her softly-throbbing folds, getting slicker and slicker with each and every second. She clenched down on the butt plug with all the strength she could muster, then pushed her legs together, holding the dildo tight against her pussy. As more of her juices leaked onto the toy, and as the thought that her arousal was going to be fucked inside of her ass, she felt Mistress start to pull the butt plug out. She let her eyes drift shut as it began to slide out of her, feeling each and every centimeter of the toy as it stretched her ring. When it reached the thickest part, she felt Mistress rub her butt with a loving hand. She opened her eyes, wondering what she had on her mind.
“Okay, you can relax now, sweetie...” Cheerilee purred, softly thrusting her hips back and forth to get the toy all nice and wet. “But only for a few seconds. When you’re ready, I want you to clench down as hard as you can again, and hold it for as long as you can.”
“Yes, Mistress...” Celestia pulled a pillow over, took a few deep breaths, then used what little strength she had back there to do as Mistress had ordered. She held the toy for as long as she could, then after several quiet moments, save for the soft schlicking sounds of the dildo sliding back and forth against her crotch, she relaxed, panting softly. “I... I think I’m ready, Mistress,” she said as the butt plug finally slipped out.
“Good, because I’m ready, too,” Cheerilee replied, squirting no small amount of lube into her submissive’s gaping hole and onto the dildo. She wrapped a hand around the toy and stroked it as if it were a real cock, coating it in the slick substance, and after she squirted more on the tip, she placed it against Celestia's slowly-closing hole. “You ready to be fucked senseless?” she asked, placing her left foot on the bed beside her lover, standing over Celestia as if she was an alpha dog about to mercilessly breed his bitch.
“Yes, ma’am!” Celestia said with a nervous grin. She dared not push her hips back, for only Mistress could give her pleasure. If she tried to pleasure herself, she knew that she’d be worse off than if she waited for her Mistress’ loving touch. So instead of doing what her heart and body yearned for, she wiggled her hips and spread her legs, arching her back so that her butt was easily accessible to the dildo that was sure to be inside of her in any moment. The thought to spread her cheeks for Mistress crossed her mind, but she hadn’t been ordered to do that, so she didn’t move. After several seconds passed in silence, the flat head of the dildo pressed against her hole. As it spread her ring further than ever before, she couldn’t stop a soft whimper of need from escaping her lips.
“Heh, is my little slut in need of a good fucking?” Cheerilee purred, slapping Celestia’s butt with the palm of her hand. She heard another whimper slip from her lips, and knowing how long it’d been since she’d last fully pleasured her submissive, she gave in after another few moments. “The safety word is cake if things get too much for you to handle. Mistress will never think poorly of you for trying to handle something that you’re not ready for...” she said softly, rubbing the spot that she’d just slapped.
“I know, a-and thank you,” Celestia murmured, feeling her cheeks warm up as she blushed. Her eyes went wide as the tip of the toy finally slipped inside of her, and her mouth formed a small, tight ‘O’ as her ass was stretched far wider than ever before. She clenched down on the dildo and grunted, making Mistress stop her inevitable domination of her body, mind, and soul. She almost said the safe word, but bit down on her tongue instead, for her pride would surely be injured if she uttered such a depressing phrase moments into the part of the night that she’d desperately been waiting for.
She had wanted a good fucking for most of the week, and she was going to get a good fucking, one way or another.
Preferably this way.
“You okay, my cute little butt slut?” Cheerilee asked, running her fingers along the underside of her submissive’s right foot.
“Yes, Mistress, I’m fine. You can keep going,” Celestia panted. “Thank you for asking...” She licked her dry lips and pushed down like Mistress had taught her. In their first night under the sheets, Mistress had shown her that it helps when you’re trying to take a toy such as this, and it was definitely helping her now. The dildo, still vibrating, passed the halfway point, going much too slow. The thick, bumpy medial ring grazed against her puckered ring, then she felt Mistress gently work it inside of her through short, yet firm, thrusts. A minute passed in silence as the medial ring slid in and out of her hole, over and over, almost as if Mistress was teasing her. Celestia couldn’t take it anymore, so when the ring slipped inside of her once more, she pushed her hips back, taking the rest of the toy in just a few seconds, throwing all caution to the winds as she wondered what naughty punishment Mistress had in store for her. Before she could look over her shoulder to hopefully see a look of approval on her lover’s face for taking the entirety of the toy, she felt Mistress’ fingers wrap around her long hair, yanking her head back.
“Getting a little cocky, eh? We’ll see how you feel after I’m through with you...” Cheerilee snarled, gently bucking her hips back and forth. The toy’s base, centered right around her clitoris, rubbed against her little love button, pressed up against it nice and snug. She pulled the toy out of her lover, slapping her gaping hole with it while pressing the toy firmly against her clitoris. Before she could give her lover a chance to whimper, she pushed the toy back in until Celestia’s ass met her hips. “I hope you’re ready...” she murmured, yanking her hips back. The toy’s vibrations were already making her legs tremble, the tingles of an orgasm already starting to form in her core. She watched on with an unwavering gaze, slightly amazed at how quickly Celestia was able to become accustomed to such an enormous toy so quickly. The sight of the dildo gliding in and out of her ass made her a little envious, but as a Mistress, it was her job to ensure that her submissive was always taken care of first, in every sense of the phrase.
Besides, she could always order Celestia to fuck her with the strap-on.
That thought alone sent a naughty shiver up her back.
As a sly grin formed on her face, Cheerilee pistoned in and out of her lover, listening to Celestia’s cute, soft moans grow louder and louder until she was moaning incomprehensibly. She slowed down a little bit, letting her lover regain her composure for the finale as she let go of her hair. “I bet you love getting bent over and fucked senseless, don’t you, slut?” she purred, noticing that Celestia’s toes were starting to curl up. She felt tingles emanate from her core, starting to course through her body like an overflowing river.
“Yes, Mistress!” Celestia moaned. “I love how thick your cock is!”
“Yeah, I bet you do...” Grabbing her lover’s hips with a firm grasp, she rammed in and out of Celestia with all the strength she had left, pulling out most of the way before shoving her length all the way back inside. She bent over her, pulling her ass up so that she could fuck her harder, faster.
The vibrations, mixed with the constant, fast-paced fucking of a lifetime, was way too much for Celestia to handle. Her legs collapsed out from under her as her vision went blurry. The wonderful fucking halted for a second, but started up again just as fast when Mistress held her ass up, fucking her as if she was trying to milk her for her cum. She grabbed her breasts and pinched her nipples, squeezing her breasts with the rest of her fingers as her mind went blank. Wave upon wave of glorious pleasure built up and burst within her core, her juices squirting against Mistress’ legs and the sheets below her over and over again. Now utterly exhausted, and dripping with sweat, Celestia felt Mistress lower her butt back onto the bed as gently as she could, then slowly started to pull the dildo from her used and abused hole, her warm cum trickling down from her slit. The thick head slipped out of her with a soft plop, and she jumped a little bit, feeling the tip brush against her overly-sensitive clitoris.
Cheerilee turned off the vibrating part of the toy, undid the straps, then pulled it down a little bit as she observed just how wet the inside of the crotch was. Her juices glimmered in the soft light, already dripping through the soft material. She set the toy on the edge of the bed, then planted several kissed on the back of her right leg, finally ending up on her pussy. Cheerilee nudged her legs aside with her head, then lapped at Celestia’s slit, cleaning her and giving her a minute amount of pleasure. Standing back up, she placed a hand on Celestia’s shoulder and gently shook her. “You okay, cutie? I’ll be back in a few seconds with some water...” she said, running her fingers through Celestia’s hair.
“Okay...” Celestia said, pushing herself up. Good thing I have another set of sheets... These are gonna be ruined after tonight... she thought with a smirk. Hearing footsteps come ever closer, she lifted her head up just in time to see Mistress walk back in, carrying a couple of cold bottles of water from the refrigerator. Mistress sat down next to her, draped an arm over her shoulders, then pulled her close, laying her head against hers as she handed her a bottle. “Thanks,” she murmured with a soft smile, her mind still hazy from the best butt fucking she’d had in her life.
“How’re you feeling? I didn’t go too hard, did I?” Cheerilee asked, looking into Celestia’s eyes with a hopeful smile. “Heh, my legs are still trembling from that toy! I can only imagine what it was like for you...”
Celestia took a few deep swigs of water, then set it aside. “Well, you know you do not have to imagine it, Mistress...” she said, biting her lip as she flicked her gaze up to meet her lover’s. “The night is still young, after all...” she breathed, leaning in to steal a quick kiss from Mistress’ lips. She pulled back, a small bridge of saliva connecting their lips. Picking up the strap-on, she held it up in front of her, the scent of Mistress’ juices still fresh. “So what do you think, Mistress? Care to partake in one of the best orgasms you will have in your life?”
Cheerilee smirked. “Now, how can I say no to that?” she asked, her mouth watering at the thought of taking the toy to the hilt like her submissive had done just mere minutes ago. “I do have one condition, though...”
Celestia cocked her head to the side as she watched Mistress grab something from out of her sight. “Oh? And what might that be, Mistress?” she asked, a little bit of curiosity coloring her tone.
Cheerilee held up the butt plug and the vibrator with the knot and shot a sly grin her way. “You have to wear both of these at the same time, and you have to let me knot you again with my toy. Seeing it slip inside of you, and how your pussy accepted it as if it was its rightful place?” She paused as a shiver ran up her back, emanating from her now-sopping wet pussy. “I want you to have at least two more orgasms before I cum. Is that understood?”
“Y-Yes, Mistress!”
