Author's Note

This chapter was written by Jubilee Glider.

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A Helping Hoof (Jubilee Glider)

The creativity room was in shambles, more so than normal. Rarity had a whole line of dresses she was trying to make for a play that was to start in less than a week. The problem was that she had an itch, so to speak. She had been helping Twilight establish and continue her relationship with Princess Luna. They make the cutest couple, she mused. Also, Fluttershy and Rainbow Dash couldn’t seem to keep their hooves off of each other now that they have openly shared their love for one another to everypony. “Get a room you two!” she would say, not meaning it, of course. She liked watching them make out. Not that she would admit it to anypony, but this left her feeling… rather… frisky.

Normally she would go to Manehattan or even Canterlot and find a stallion. Tonight she was in need of something different. She was always in control of the stallions, but this time she wanted to be controlled. There was only one pony she trusted enough to lose herself to. She had to find Pinkie Pie, and she had to find her fast.

Pinkie Pie hosted a party for her friend Jubilee. It was her 20th wedding anniversary, so Pinkie was going all out. There were cakes and pastries of every flavor and size imaginable, and Sweet Apple Acres Cider to drink. She had gotten Vinyl Scratch to come DJ, and Octavia with her orchestra for those special moments to set the mood just right.

The party was in full swing as Rarity appeared at the door. She knew she could go in and nopony would think twice about it. Although, if Pinkie Pie and she disappeared after she crashed the party then there might be talk. She didn't really care. The need was too great. She opened the door and entered with intention to seek out what she needed.

Pinkie Pie was dancing with anypony and everypony she could. She was having such a great time that she almost missed her friend coming in through the front door. As she noted the look in Rarity's eyes, Pinkie knew the what brought her around. Oh gosh! She gave a nervous smile to the pony in front of her. I wish I could help her right away, she thought to herself. But this party is too important to Jubilee. She graciously withdrew from her partner. I’m so sorry, Rarity. You’re going to have to wait a little longer. With that thought Pinkie danced herself in the opposite direction.

Anxiety was getting a hold of Rarity. She was in the most dire need of some special relief. She had been searching the party for Pinkie Pie for the last hour and a half, but to no avail. Rarity had seen her there. She was sure of it. It was like Pinkie was avoiding her. That's it! Rarity realized. She must've seen me come in, and now she's trying to ditch me! Her sneer was getting noticed by the party guests as she continued her search. How could she do this to me? Now Rarity was about to lose it. She didn't know if she was going to cry or scream. She was almost ready to announce why she was there just to try and draw Pinkie out of hiding. That's when somepony tapped her on the shoulder.

Pinkie Pie had been watching Rarity the whole time. She knew that the mare was about to either explode or break down. Pinkie was confident she could make her exit without too much heartache from Jubilee. "Hi, Rarity," Pinkie Pie said sheepishly.

"Oh, my goodness, Pinkie Pie. Where have you been?" Rarity cried. "I've been looking for you for over an hour. I need your services! I need you…" She glanced around at the other party guests, suddenly self-conscious. "Ah, your special party skills, as it were," she said as her cheeks turned crimson.

"Of course, silly,” Pinkie said, still dancing to the music. “I knew what you needed as soon as you came through the door. I wasn’t able to leave then, but I can now. Are you ready?"

"I am so ready. Just thinking about it is driving me absolutely crazy," Rarity said, heading to the door.

"Not as crazy as when you thought you weren't going to find me,” Pinkie giggled at the back of Rarity’s head. “That's why I decided it would be a good idea to stop playing hide and seek,” she said as she followed Rarity back to the Boutique. “There's no reason anypony else needs to know about this.”

"I am truly sorry about pulling you away from the party, but this is rather urgent," Rarity said. She slid her tail off to the side so Pinkie could see just how wet and swollen her pussy was.

She growled appreciatively at the sight, but her eyes were drawn upward to the soft flesh under her tail. "It was a great party too,” Pinkie Pie said as she bounced along, mesmerized by the view in front of her. “It looks like the afterparty will be just as awesome but on a different level." She didn’t think Rarity knew how much Pinkie liked her plot. She’ll find out tonight… She nodded to herself and put a little more bounce in her step.

As they were going through the front door of the Boutique, Pinkie stopped and gave Rarity a look of alarm. "I don't think that Sweetie Belle would like to wake up to what we are about to do. Do you?"

"That's the beauty of it, dear,” said Rarity, looking over her shoulder at Pinkie with a devilish grin. “Sweetie Belle and Scootaloo are at a sleepover at Apple Bloom's tonight. I don't think we have to worry about that.”

Pinkie Pie knew that she was in for an extreme session, to say the least. She followed Rarity up the stairs, staring at her flank and plot and getting little shivers the whole way until they entered the creativity room. Rarity used her magic to pull out her ‘toy’ box. Pinkie immediately opened the box containing dildos, whips, gags and Rarity’s other dominatrix goodies.

Wearing a mischievous smile she slipped on a set of latex stockings - slowly, so Rarity could watch. The corset was next. She had Rarity help her lace it. Finally she picked up the riding crop. “Ready, Rar?”

Rarity took a deep breath. “Ready, Pinkie.”

The crop smacked into Pinkie’s hoof with a loud crack. “Then playtime is over!” Pinkie said harshly. “You are mine! You will do as I say, when I say it!”

"Yes, Mistress," whispered Rarity, so excited her voice refused to come out.

She turned her back on her play pony and lifted her tail high. "Now, lick my slit!" Pinkie demanded.

"Yes, Mistress!" She immediately started lapping at Pinkie's now soaking wet gash, eliciting a soft moan of approval. While she worked on Pinkie her horn started glowing blue, and her special bench came floating out of the closet.

The bench was cushioned and equipped with stirrups and straps. The stirrups faced down instead of up, putting her legs in just the right position so Pinkie could have full access to her luscious and almost dripping wet pussy and her tight little asshole.

The thought was enough to make Pinkie push back eagerly against Rarity’s tongue, making her play pony squeak in surprise. She hid a smile and pranced out of reach. "That's enough for now," she told Rarity. “Get into position.”

"Yes, Mistress," she acceded, licking her lips clean of Pinkie's juices. She lay on the bench and put her legs into the stirrups. Pinkie leaned over her to strap her legs and her barrel in. Oh my! A look of concern flashed across her face. This looks to be serious. She's never strapped me in like this before.

The leather flap of the crop found its way to Rarity's flank. Pinkie dragged it down her hip, around the lower part of her ass. It traveled upwards; Rarity shuddered as it lightly brushed her left outer pussy lip. It came to rest on her tight rosebud for a few seconds. It lifted and immediately came down sharply across the back of her legs, just below her ass. She twitched from the sensation. Her breath caught, but she remained vigilant in her silence. She knew from her past sessions with Pinkie that she wasn't allowed to make a peep without permission.

Leaning in close Pinkie confessed, "I will give you permission to scream, but not yet, my little filly. You have to show a little self-control first. I can tell that you’re enjoying this by how wet your pussy is. It's practically dripping."

Oh, Celestia. It’s so true. She could feel her juice starting to pass across her clit. I want her so badly that it hurts. She wanted to tell her, but she didn't like to get spankings as a punishment. Not all punishments were as hurtful as that one. Sometimes it almost seemed like she was rewarded for misbehaving, but every once in awhile Pinkie would really punish her. She couldn't sit for nearly two days after the last time.

Pinkie walked slowly around Rarity, trailing the crop through her coat until it suddenly met its mark and stung her again. "Speak, my little whorse!" Pinkie said, quickly jumping back in front of Rarity.

“Aahh! I need you so badly, Pinkie– I mean, Mistress!” Rarity blurted out, unsure of how long she would be allowed to talk. “Please, say you’ll never leave me! I love you, Pinkie Pie!” Her eyes grew wide in astonishment even as the words left her lips.

Surprise showed in Pinkie’s eyes, but she recovered quickly. "Silence!" She raised a questioning eyebrow. "You 'need' me, do you? And how could I ever leave a pony that needs me sooo bad?" Then she leaned in so close to Rarity's ear that her lips brushed it when she spoke. "I love you too, Rar," Pinkie whispered. At that very moment, she was happier than she ever was.

Unable to contain her joy, a squee escaped Rarity’s lips. Unfortunately, she had forgotten that Pinkie was still in charge. She knew by Pinkie's reaction that she had slipped up, and that she was about to be punished. Again.

"Did I just hear a sound?" Pinkie’s eyes squinted to show anger, but the light that shone in them gave her away. "Ooohoho, my little pony! You did not just break your silence! You know what this means don’t you?" A wicked little grin grew upon Pinkie’s face. Yes! Now I can use her slip-up as the excuse for my plot play plans.

Rarity’s anticipation grew as Pinkie let the silence stretch. Oh, yes. This going to be good. If it's taking this long for her to decide… Rarity closed her eyes and trembled. Not from fear, but because she could tell by those eyes and that smile that her punishment wasn’t going to be by spanking. Not that time around.

Out of the plethora of dildos to choose from, Pinkie chose the smallest. She rubbed it lengthwise against her captive’s clit, trying to get her to squeal again. She actually liked it when Rarity made noise, but she had to play the part she was given. Rarity couldn't be allowed to get away with making noise when she wasn't supposed to. She pulled Rarity’s lips back with her free hoof and was surprised to feel Rarity shaking. Pinkie’s face softened. This was supposed to be fun, not frightening. After Rarity’s profession of love for her, Pinkie was determined to make it more about the fun. As she shifted around in front of Rarity, Pinkie put on as serious a face as she could, "Know that you will be punished for your little outburst, my pony slut. You are allowed to make noise, but not speak, unless spoken too. Do you understand?"

“As you command, Mistress," Rarity replied.

"Hmm…” Pinkie was back behind Rarity in a bounce. “What shall your punishment be?” The crop once again landed on the back of Rarity’s thighs. “A spanking, perhaps?" She paused for dramatic effect. "I think not! I believe I know exactly what you need," Pinkie said, giggling to herself.

Rarity whimpered at the attack on her thighs, but was also elated at Pinkie's words. I wonder what she could have planned? I hope it will get me off soon! This is driving me crazy!

Pinkie moved the toy box behind Rarity. She grabbed the lube and applied a generous amount to Rarity's ass.

Rarity's eyes popped wide open, and she squeaked as she realized Pinkie's intent. All she had to do was speak the safety words – Pinkamena Diane Pie – and everything would stop…

Pinkie knew to start small and work her way up. "You are going to enjoy this, my pet! And so am I!" She put the head of the small dildo that was in her hoof against Rarity's tight little asshole. She could tell that Rarity was nervous because she tensed her entire backside as the toy touched its mark. "You really should relax, my little anal virgin; it will help this whole process. We’re going to try something new this time. I want you to become my butt slut.” Pinkie hesitated. “And by my, I mean that your luscious plot will belong to me! I don't want you to share with anypony else. You need to Pinkie Promise, Rarity!”

Nervous but eager to try, Rarity spoke the words without really meaning them. "Cross my heart and hope to fly, stick a cupcake in my eye."

Pinkie’s head dipped a little. “Rarity, I don't think you get it,” she said softly. “This is for Pinkie Pie, not your Mistress."

"Oh? Okay, Pinkie Pie. I thought we were still in the session," Rarity said, a little confused. "Is the session over, then?"

"No, it's not. I know how you like the stallions, and I need you to do this for me," She was shuffling a hoof on the floor. "I'm going to be selfish and I want you to go along with it. I want a little something just for myself. I need you to Pinkie Promise me that you won't let a stallion have your plot. I need you to really mean it!" Pinkie said in a somewhat pleading voice.

Feeling the importance of Pinkie Pie words, she took a deep breath, "I, Rarity, Pinkie Promise that my plot belongs only to Pinkie Pie,” she said solemnly. “Cross my heart and hope to fly, stick a cupcake in my eye." She hoped Pinkie could feel the essence of her declaration.

"Thanks, Rarity. You’re the best." She kissed Rarity on her flank. "Now, are you ready for this?” she asked excitedly. “It's going to be sooo awesome! I love you, Rarity!”

Rarity realized that it wasn’t just the heat of the moment that had caused the words to come out. "I love you too, Pinkie Pie." She knew it to be true.

"Now that that's out of the way… Let the romp begin!" Pinkie announced.

"Please be gentle. This is new to me," Rarity said uneasily, not getting the hint that the session had resumed.

"Your Mistress is going to let that outburst slide. Keep that up, though, and you may not sit again for a week."

"Eep!" is all Rarity could get out.

The corners of Pinkie’s lips bent up as she turned her attention back to the job at hoof. She dug through the box of toys until she found one of Rarity’s egg vibrators and held it up, the egg in one hoof and the remote in the other. "Rarity, I need you to hold this to your clit with your magic."

"Mistress,” she protested quietly, bewildered by Pinkie’s request. “I thought you didn't like me to use my magic because it takes away from the sex."

"You may use it when I want you to,” Pinkie said certainly. “Only when I want you to. Understand?"

"Yes, Mistress," Rarity said as she took hold of the entire contraption with her magic.

The crop struck once more against Rarity’s thighs. "Uh-uh, only the egg,” Pinkie corrected her. “I keep the controller.”

How did she do that? She only has two hooves! Rarity let go of the controller, and put the egg against her clit, just like her Mistress commanded.

Pinkie started the vibrator off on the lowest setting and strapped the controller to the inside of Rarity's left leg. She didn't want to push Rarity over the edge too soon. She then found the other egg vibrator and pushed it into Rarity's pussy.

"Mmm-hmmm," Rarity moaned as it slipped into her still wet gash.

"You like that, don't you?" Pinkie asked of her prey.

"Ooh, yes, Mistress," she said dreamily.

"I haven't even started it yet." Pinkie switched it on, and strapped the second controller to Rarity’s right leg, all the while maintaining the pressure of the dildo against Rarity’s sweet little pucker.

"Hhhnnnggg," Rarity moaned again.

"That's my pony slut," Pinkie breathed. She pushed the head of the small dildo into Rarity's ass.

Rarity inhaled deeply through her teeth, then slowly exhaled.

Pinkie slowly removed the head, so that it was just at the edge of Rarity's asshole, then pushed it back in and added an inch to the part that was already immersed. She pulled it out to the edge of Rarity's asshole, then in again, making her whimper in discomfort. Each time she pushed it back into her, she added another inch until the entire thing was inserted to the hilt.

Rarity felt at first like her ass was going to tear open, but as Pinkie Pie worked the toy back and forth, her muscles relaxed and she enjoyed the sensation. It actually surprised her. With both vibes going and the new sensation filling her, she wasn't sure how long she would be able to keep herself from cumming. A sudden "Oh, yes" escaped her lips and only the straps kept her from pushing back into Pinkie's thrusts.

"Ah-ah-ah! You may not cum until I say so. I think you’re starting to enjoy this little guy too much," Pinkie said as she slowly removed the dildo from Rarity's ass. “Time to move on!”

Pouting at the loss of fullness in her backside, she realized that she might actually enjoy being fucked in the ass. Maybe that's the punishment she was talking about: getting me to like it, and then taking it away. I want it so badly now! Please, Pinkie, put it back in!

Pinkie grabbed the double-ended dildo they had shared on occasion. It was the next in line for the increasing sizes that were available in Rarity’s collection. Pinkie added some lube to its head, and gently nudged it against Rarity’s asshole.

Her breath caught with anticipation.

Pinkie started to push the head in. Rarity’s ass seemed to be just as tight as when the little one was going in the first time.

As her ass stretched again, Rarity tightened her muscles and tried working through the sensation. "Aahh!"

Pinkie paused. "That’s not going to work. Relax. Take a deep breath. Exhale, and relax. Good girl," Pinkie said as Rarity did as she was told. The resistance began to wane, and the head slipped in. "See? I think this could be the start of a beautiful anal relationship!” Pinkie chuckled.

"Uh-huh," Rarity said closing her eyes and imagining her biggest toy sticking out of her backside. At least that's what it felt like.

Pinkie pushed the dildo into Rarity's ass, and then pulled it out so she could just see the head. Pushing it back in again and adding a little more depth each time until about three-quarters of it were in the embrace of Rarity's ass. At that point Pinkie's own juices were trickling down her leg. She had dreamt of such a session for so long, and now it was finally happening! She watched as she slid the dong out of Rarity. She was captivated at the sight of Rarity’s asshole being drawn out by the dildo as she removed it, and how it clung and sucked in as she slid it back home. She also noticed, as she worked it back and forth, that Rarity's ass was relaxing. "How does that feel, my little pony?"

"So good…” She arched her back as much as the straps would allow. “Please, don't stop."

"Would you like it a little harder or faster?" Pinkie Pie asked.

"Both please, Mistress," Rarity begged.

"Only for you, my butt slut," said Pinkie as she picked up the pace a little. Pushing the phallic in as far as she could each time.

"Oh Celestia, yes. Yes!" screamed Rarity as she tried her hardest to buck back into Pinkie again.

"No, no, no. You can't cum yet," Pinkie sang and pulled the dildo out of Rarity's ass with a loud popping sound. Pinkie’s body quivered from her exhilaration. She was so close to cumming, yet she would wait and come with her lover. But that pop that came from Rarity's ass almost sent her over the top. Oh my Celestia, that was the most awesome thing I have ever been a part of.

Rarity groaned. She wanted to cry. She needed Pinkie to put it back inside her. She wanted to cum. She needed to cum! Her asshole felt so vacant again. She was sure that she was in the midst of the punishment Pinkie had mentioned before.

Pinkie was staring at Rarity's ass. It was stretched slightly, but not gaping. She looked down, and saw that her own inner thighs were soaked from her excitement. It wasn’t about controlling Rarity anymore, or the punishment she was supposed to get. It was about Pinkie’s own deepest desires. She picked up the next dildo in the collection. She lubed the end and touched Rarity's asshole with it.

"Oh yes, thank you, Pinkie…" She didn't even know she had said it. She had only meant to think it.

The crop landed with a loud smack. "Only when spoken to, ass whorse!" Pinkie screamed.

"So sorry, Mistress. Please forgive me," Rarity breathed as she relaxed her ass muscles to invite the new toy.

"I would punish you severely if I wasn't so turned on right now," Pinkie said, watching Rarity take her second biggest dildo slowly into her anus. The sight was mesmerizing to Pinkie Pie. She could almost imagine it sliding into her own back door as she watched. She was so horny that it wasn’t just her vagina that was trembling, but her ass as well. Pinkie suspected Rarity was aching to cum herself and was frustrated at not being allowed. "Do you want me to fuck you? Do you need me to fuck you?"

"Yes. Yes, I need you to fuck me!" Rarity screamed.

"Where do I need to fuck you?"

She caved. "I need you to fuck me in the ass, Mistress. Oh Celestia, please fuck me in my ass!"

"Are you sure? Because you’re still not allowed to cum yet," Pinkie teased. She started to pump the dildo in and out of Rarity's asshole.

"Why-hy-hy no-ot?" Rarity whined, "Please. I need to cum so bad. I want to cum for you, Pinkie Pie."

"Soon, my little filly. Soon." Pinkie started to fuck Rarity a little faster for a few strokes. Then she slowed down, making Rarity cry out in frustration. She needed to use the final dildo – Rarity's favorite one, in fact. It was also the biggest one in her collection.

Pinkie pulled the dildo in Rarity's clinging ass out to another loud pop. Oh, that sound is sensational! She exchanged it for Rarity’s favorite. "I think you're ready for this."

Rarity’s eyes had rolled into the back of her head. "Please, just fuck me, Mistress."

She squeaked and fell silent as Pinkie pushed the favorite into Rarity's ass. It took a little force, with quite a few pauses for some relaxation, but it inched further in. Then she started to reach the toy’s knot, a bulge almost as big as her hoof. As she pushed the knot up to Rarity's butthole she could tell that Rarity wanted it. Her asshole was practically sucking it in. It was the most amazing thing Pinkie Pie had ever seen.

"More. Push it all the way in, Pinkie.” Pinkie hesitated, not wanting to hurt her. Rarity pulled at it with her muscles, trying to coax it in. “Please,” she pleaded. “Fuck my ass with it. I need it. Push the knot in. I can take it.”

Pinkie pushed carefully and the knot slowly slid in.

"Yeees! Push! Push!” She trembled as she fought to open up for it. “I love you, Pinkie Pie! Oh Celestia, I love you!" Rarity screamed as the knot passed by her sphincter muscles. "Now, fuck me! Fuck me hard!"

"I love you, too, Rarity!" Pinkie said, obliging her charge’s screams, and fucked her as hard and as fast as she could. Rarity’s hips shivered as her pleasure neared its peak. She was on the edge of cumming when Pinkie Pie pulled the dildo from her ass.

Rarity whimpered at the pain and the sudden emptiness. "Why!” she howled. “This is cruel and unusual punishment, Pinkie Pie!” Then she felt something else press against her butthole.

Pinkie had lubed up her hoof and pressed it to Rarity's yearning anus. She pushed her hoof inside.

Rarity gasped and moaned in ecstasy. "I don't know what you're doing back there, but please don't stop until I cum. It feels as though you have your entire hoof in my ass. I don't care if it is. Just fuck me until I cum, please!" Rarity begged.

Pinkie pushed her foreleg into Rarity until she was up to her fetlock. She added more lube and started to hoof fuck her lover's asshole. That was her dream, her greatest fantasy come true.

As she quickened her pace, so did Rarity's breathing. "Yes! Yes! I'm going to cum!” Rarity let loose with the greatest orgasm she had ever had in her entire life. ”Aaaaahhh!" She had fireworks going off in her head as she came so hard she shot out the egg that was buzzing in her pussy, and she dropped the other from her clit. She was lost in the sensation of Pinkie Pie fucking her.

The sight in front of her turned Pinkie on so much that she only needed to exact a little bit of self-motivation to cum with Rarity. She could feel her marefriend’s ass compressing around her hoof and fetlock as she pulled and pushed. "I can feel you clamping around me… This is way better than cupcakes. I love you so much, Rarity!"

"I love you too, Pinkie Pie! I am yours forever, dear," Rarity said as Pinkie slowly removed her hoof from Rarity's back door after her orgasm finally subsided. "I think I am going to be sore for a few days, Pinkie, but it was sooo worth it."

Pinkie looked up sheepishly from her sticky hoof. "I wasn't sure if you were going to like some of the plot play I did…"

"It was simply amazing, dear. I didn't realize you liked my plot so much. Is this a new interest?" Rarity asked, shifting her backside with a look of slight discomfort on her face as Pinkie undid the straps.

"No, I've liked it for some time now. In our previous sessions, I wasn't sure if you would enjoy it,” Pinkie said as her cheeks got slightly pinker. “But tonight, I just felt that it was a good time to let you know about it."

"I didn't know I enjoyed it until tonight, either. Thank you, Pinkie Pie." Rarity removed herself from the bench and stood, a little bowlegged.

Pinkie felt an overwhelming urge to latch onto Rarity’s neck, pulling her to the floor in a huge full-body hug. “I love you,” she mumbled into Rarity’s shoulder.

Rarity returned her hug. “I love you, too, Pinkie Pie.”

The two mares remained in the embrace for quite some time, caressing each other until their work forced them appart. Each finally called them away to their separate lives.