Cheerleaders of the Head Mistress

by StormLuna

Rating: mature
Tags: Human, Twilight Sparkle, My Little Pony: Friendship is Magic, Other, Porn, Sex
Length: 4465

After their performance at the buckball game, Shimmy Shake and Lighthoof return to their dorm room to discuss the day's events. Things very soon transform from a mere conversation into something more, much more.

After their performance at the buckball game, Shimmy Shake and Lighthoof return to their dorm room to discuss the day's events. Things very soon transform from a mere conversation into something more, much more. Fortunately for Shimmy and Lighthoof, their activities would not go unnoticed by Twilight.

Primary characters in this story are 18 years of age and older

Warnings: Body fluid consumption and water sports.

Published 2019-08-14 23:10:02 UTC
Last updated 2019-08-14 23:10:02 UTC

First Experience

The buckball game between the School of Magic and the School of Friendship had just ended and unfortunately, the School of Magic won the game 5-4. Normally such an outcome would be taken negatively by the School of Friendship and everyone involved but the coaches of the team were not upset nor was the coach of the cheer squad. For her it seemed like an afterthought. What was more important to her was the performance of the cheer squad at halftime.

Rainbow turned to the cheer squad and exclaimed, "You guys were amazing!" The buckball team groaned upon hearing this. They weren't sure whether she was talking to them or the cheer squad but knew that they definitely were not amazing. Rainbow continued, "It was flawless. I can't think of any way that could've been better!"

While Rainbow was in a great mood, Smolder was not in the same mindset and knew that things could have been better. She commented, "We could have won the game."

Rainbow scoffed, "The game was just a sideshow. You guys were the main event!"

After what had been several frustrating days of Rainbow not caring one bit about the cheer squad, here she was complimenting them and acting like their performance was what mattered. After one final compliment, Rainbow headed off to talk to Twilight while the cheer squad dispersed and returned to their dorms.

As they were returning back to their dorms, the head dancers, Shimmy Shake and Lighthoof began to talk among themselves. "What was up with that?" questioned Shimmy. "For so long Rainbow didn't seem to care one bit about the cheer squad and now all of a sudden she is acting like we are more important than the game? The big time sports pony acting like we are more important?

Lighthoof was skeptical. "I personally think that she was only putting on a show. After all, she didn't want to look bad in front of Head Mare Twilight or Princess Celestia."

Once the two were out of sight, like they often do when they are not around others, they joined hands like they have ever since they became friends. Once they got into their room, they shut the door and Lighthoof plopped down on her head. She continued to question Rainbow's actions, "So do you think Rainbow will be back to her 'I don't care' attitude next time we practice or will she remain enthusiastic like she was today?"

"Oh I'm sure she will be back to her normal self. Like you said, she was likely just putting on a show for Twilight." replied Shimmy.

Shimmy too plopped down on her bed but while Lighthoof was laying on her back, Shimmy was on her side staring in the direction of Lighthoof. While the two had been friends for years, Shimmy had always found her friend attractive and as time passed, that sense of attraction had grown. Lighthoof never paid much attention to this though as she seemed to be looking straight forward or had her attention elsewhere.

Several minutes had passed and neither had said a word after questioning Rainbow's actions, which was very unlike Shimmy as she was normally fairly talkative. While she did not look over towards her friend, Lighthoof could sense something was off. She asked, "You ok Shimmy, you're usually not this quiet."

Her statement snapped her friend out of the daze she had fallen into, "Oh yeah, I'm alright. I just have some things on my mind."

Lighthoof turned over and faced her friend and couldn't help but notice that not only was she intently staring in her direction, but that she had a dream like smile on her face. She knew something was up with her friend and was going to find out. She walked over to Shimmy's bed, grabbed her by the hand and pulled her up. She then sat down and still holding onto her hand, she faced Shimmy and asked, "What is up with you? Are you ok?"

Shimmy blushed and put her head down, "Well you see, uh....."

Lighthoof had a feeling as to what was going on but thought of a way to find out. She turned her body towards Shimmy, grabbed her leg and began to run her hand up her thigh. Immediately Shimmy's nipples hardened and were clearly visible. Lighthoof noticed this and giggled, "You want me don't you Shimmy, you think I'm hot, don't you?"

Shimmy's blushed deepened as she looked over towards her friend. This was something that she never expected to happen and it continued to be hard for her to give an answer, "Well, uh...."

"You do, don't you?" giggled Lighthoof. She broke into a smile and continued, "Is that why you always give me those cute, seductive looking smiles?

While Shimmy continued to be nervous, she knew that the time had come to admit it. She turned towards Lighthoof, placed her hand on her knee and replied, "Yes Lighty, I mean Lighthoof, I've thought you are hot for years."

"Lighty?" Lighthoof giggled. "You already have a special name for me?"

"Uh, well yeah." replied Shimmy.

Lighthoof pulled Shimmy closer to her and cupped her breasts. She gave her a smile and giggled, "Well I find that incredibly sexy!" She then pointed towards her breasts and continued, "You know, you can hold mine too."

Shimmy gave her a smile and reached out to cup hers as well. The two sat there in an odd silence until Lighthoof pulled her up and asked, "So Shimmy, now that I know about this what would you think about being more than just mere friends? Would you want to be something like friends with benefits?"

This was a situation that Shimmy had wanted to hear for ages and finally it was happening. She planted her hand on Lighthoof's butt and gave her a very enthusiastic, "Yes, yes! I'd love that!"

The two pulled one another into a tight embrace and began to kiss passionately. Soon their hands would move to the other's butt and the groping began. They pressed themselves as tightly together as they could and their breathing intensified as the kissing became more intense. Mere kissing was not enough for Shimmy though, she wanted to feel her friend's tongue up against hers so she began to stick her tongue out and the moment Lighthoof felt it, she parted her lips to allow entry.

The moment Shimmy's tongue touched Lighthoof's, both opened her mouths wider and began to rub their tongues together with a great amount of force. As they did this, their breathing became more intense and their groping became harder and harder. Soon though other thoughts began to run through the mind of Lighthoof, she began to think about how they had too many clothes on.

She immediately broke the kiss, gave Shimmy a smile and giggled, "You know Shimmy, you have way too many clothes on for my liking!"

She then immediately began to tear Shimmy's uniform off of her and this was a signal to Shimmy that Lighthoof wanted the same done to her. Once they had stripped down to nothing but their underwear, both girls were drawn in by the other's breasts. Lighthoof giggled, "My oh my Shimmy! I knew your girls were big but I didn't know they were that big!"

Shimmy commented, "And yours are so big, so beautiful, so sexy!"

The two blushed at one another before Lighthoof grabbed her underwear and continued, "Now let's rid ourselves of these things, alright?"

Shimmy quickly agreed and they proceeded to rip the other's underwear off. Being fully nude, more of Shimmy's long held fantasies began to surface as she got down on her knees and in what sounded like begging she said, "Please spread your legs Lighty."

Lighthoof did as requested and Shimmy immediately dove in on her. She began to suck on her and was forcing her tongue into Lighthoof's pussy. The sensation this brought her caused her to begin to squeal in ecstasy. The grabbed Shimmy's hair, began to pull on it and begged, "Suck harder baby. Suck harder, probe me deeper!"

Shimmy did as requested and then an idea began to run through her mind, she wanted to see how Lighthoof would react to being penetrated in the behind. She began to grope her ass before moving her fingers towards her crack. Once her fingers made contact with her opening, Lighthoof gasped, "Shimmy, are you?"

Shimmy nodded her head before getting back to work. She then began to run her fingers into her opening. As they gained entry, Lighthoof gasped, "Shimmy!"

While Shimmy wanted to answer her, sucking on her was more important so she gave her a simple "Mhmm!"

Shimmy continued to penetrate her fingers deeper and deeper into her before she began to thrust her. The thrusting caused Lighthoof to start screaming out her name and pulling on her hair violently. Shimmy's sucking intensified and her breathing became harder and her thrusting got harder and harder. Finally she heard the words coming out of Lighthoof's mouth that she had been wanting to hear for ages, "I'm gonna, I'm gonna, I'm gonna cum!"

Immediately a flood of nectar filled Shimmy's mouth. She moaned in pleasure as she swallowed the sweet liquid. She was enjoying this too much to stop desoute Lighthoof having climaxed. She continued to thrust her in the behind and continued to suck on her pussy. Both girls were still so lost in one another that they didn't even hear a pound on the door and a voice yell, "What's going on in there?"

When the moaning continued, the lock on the door clicked and opened. The door opened and on the other side was Twilight. What Twilight saw was something that would not please her. She stormed over to the two, ripped Shimmy's head out from between Lighthoof's legs and yelled, "What is the meaning of this?"

Both girls gave her a sheepish grin before Twilight continued, "GET DRESSED, NOW!"

Twilight stood there with a furious look on her face and once the girls were dressed, Twilight ordered, "Follow me ladies, we need to talk."

The two knew that they were likely in a world of trouble as they had never seen Twilight angry before. What the two did know though was that engaging in sexual activities in their dorm room was likely not the best idea.

Fun With the Head Mistress

As the two girls followed Twilight out of their dorm room, all sorts of things began to cross their minds. They realized that for what they did for what they did, they could very well be expelled. What would happen afterwards they were not sure but they did know one thing, they knew that simply moving back in with their parents after this kind of expulsion would not be an option. One thing that did confuse them though was that Twilight was not leading them in the direction of her office, she was taking them to the palace.

They couldn't help but wonder why Twilight was taking them there, especially given that Starlight was in her office. The two became more nervous realizing that what Twilight has planned for them may involve something more than a mere expulsion. Their paranoid sides began to wonder if perhaps Twilight isn't so friendly, they began to wonder if perhaps some sort of corporal punishment would be in store for them.

Once they got into the palace and Twilight shut the door, she grabbed the two by the hands and ordered, "To my sleeping chambers, NOW!"

This caused the two to gasp in shock. They couldn't help but wonder why Twilight would be taking them to her bedroom but had a bad feeling about it. They began to think that perhaps Twilight likes to punish students in strange and painful ways and that her bedroom was where she did so.

When they arrived in her sleeping chambers, Twilight closed and locked the door. The two looked around and didn't see anything out of the ordinary until Twilight opened a drawer and pulled out a paddle. She set it down on her bed and approached the girls, "I want to know something, what was up with what you were doing in your room?"

Shimmy began, "Well uh, you see....."

She was unable to finish the sentence so Lighthoof finished it, "You see Headmaster Twilight, we find each other hot and...."

Twilight swatted her butt and corrected, "From now on that will be Head Mistress Twilight to you." She got closer to the girls and continued, "You know, normally the punishment for what you did would be expulsion but you better thank your lucky stars that I...." she paused for a moment, groped their butts and giggled, "find you two incredibly sexy."

Both girls gasped, "You do?"

Twilight's demeanor changed immediately as she giggled, "Yes girls I do. I have decided that you can stay but you must do something for me today, something that will make me very happy."

What the two thought would be a horrible fate in Twilight's room was suddenly beginning to look not so bad, especially once Twilight began to undress. She pointed at the two and continued, "Now girls, could you do me a favor and get undressed? Seeing you fully clothed like this isn't much of a turn on."

As the two began to undress, they realized that there was a side to Twilight that no one likely knew about and a side that no one would expect. Once they were undressed Twilight grabbed the paddle and began, "Now where shall we start." She pointed towards her bed and ordered, "Lean over girls, your head mistress must punish you for your actions today."

The two leaned over and waited for Twilight to strike them with the paddle. Rather than it being a violent, hard hit, she was gently paddling the two. She kept gently paddling Lighthoof but would do something completely unexpected to Shimmy. Twilight leaned down and began to lick Shimmy's butt cheeks. Shimmy immediately began to giggle, "Stop it, that tickles!"

Twilight giggled back, "Oh no Shimmy. You were a very bad girl today and you must be punished!"

Twilight continued to lick her and shortly began to suck on her. Twilight had a feeling that would be even more ticklish for the cheerleader and she was right. Soon Shimmy was giggling so hard she began to cry. This was something that brought about a great amount of joy to Twilight, bringing one of her hottest students into a giggling cry. This did not sit so well with Lighthoof though as she wanted in on the action. She pouted, "Head Mistress Twilight, when are you going to punish me?"

"My my, so impatient." laughed Twilight. "I know you want in on the action but I'm not done with your sexy friend yet."

Twilight swatted Lighthoof's butt before returning to sucking on Shimmy's cheeks. While no one else would see it, Twilight wanted to turn her ass red and wasn't about to let anything stop her. She continued to suck harder and harder on the girl and would be pleased as she had begun to slowly but surely accomplish her mission. After an hour of sucking, giggling from Shimmy and pouting from Lighthoof, Twilight was finally finished. She stood up, swatted the girl's butt and laughed, "You know Shimmy, you look awfully hot with a red ass." She then turned to Lighthoof and continued, "Now don't go thinking I forgot about you, you're just as hot as your friend."

Twilight had different plans for her. Rather than licking and sucking, she began to gently nibble on her, bringing about a giggle from the girl. While one part of Twilight wanted to bite her hard, there was one part of her, the side of her that wanted the girls long term, wouldn't allow her. Twilight continued to nibble while Lighthoof continued to giggle. Twilight decided to give the two an equal amount of time so after an hour, she stopped. She ordered that the girls face her and asked, "So girls, are you enjoying this."

In unison the two replied, "Yes Head Mistress Twilight, yes."

Twilight began to eyeball them further and said, "Now you do know that this was merely the beginning, right?" She pointed towards Shimmy and ordered, "Lay down hot stuff." She then turned to Lighthoof and continued, "Help me out here. I want to give your hot little friend here an experience she will never forget."

Both Twilight and Lighthoof approached Shimmy's feet. While Twilight did not say what to do, Lighthoof figured that it would likely be the same thing, starting with the toes. They leaned down and began to suck on Shimmy's toes, bringing about a giggle and a slight kick from the foot Twilight was sucking on. While it did knock Twilight back, it did not anger her. She gave Shimmy a smile and giggled, "Oh so you're going to make it hard for me huh?" She gave her a smirk and continued, "You know its not nice to deny your Head Mistress what she wants don't you?"

Shimmy simply nodded and the two got back to work on her. They slowly began moving their sucking up her legs, causing more and more giggling from her. Not only was the giggling really turning Lighthoof on, it was making Twilight hot, very hot. Once the two got up to her knees, Twilight knew that there wouldn't be room for both of them as they got closer to their prize. Twilight pointed up and ordered, "Lighthoof, you can go suck on those sexy tits of hers, I'm going for the sweet tasting prize."

"Alright Head Mistress Twilight, whatever you say." replied Lighthoof.

Lighthoof immediately moved up and began to suck on Shimmy's tits. She immediately began to moan loudly and squeal, "Oh Lighty, oh Lighty!"

Twilight heard this and immediately laughed, "Lighty?" She sat up, swatted Lighthoof's ass and giggled, "So you have a pet name huh?"

Lighthoof blushed and nodded yes. Twilight gave her a smile and giggled, "Well Lighty, I have plans for you later!" She then turned towards Shimmy and added, "For both of you, very sexy plans."

Twilight continued to move her sucking up and knowing where Twilight was headed, Shimmy spread her legs wide. Once Twilight got to the inner thighs, she smelled something she liked, something very sweet. She swatted Shimmy's side and giggled, "Someone's turned on, isn't she?"

Shimmy gave her a response that Twilight found adorable, "Mhmm!"

"Oh my!" Twilight gasped, "My Sexy Shimmy must really want me!"

Twilight then got back to working on her and when she reached her prize, it was sopping wet. Twilight immediately dove in on it and began to suck hard. When Shimmy began to moan and call out Twilight's name, Twilight began to probe her. For Twilight, this was the tastiest thing she had ever had. While she had sucked on other pussies before, there was something about Shimmy's that began to drive her wild, drive her wild to the point that she wanted Shimmy all to herself. She gave Lighthoof an order, "Lighty, get off of her. I want her all to myself."

Lighthoof wasn't thrilled but did as requested. Twilight crawled up on top of Shimmy, buried her pussy into her face and ordered, "Shimmy, on our sides!"

Shimmy complied with the order and the two began to suck on one another. Both began to moan loudly as they intensified their sucking. While LIghthoof tasted very good to Shimmy, Twilight tasted even better. She pulled her head out momentarily and squealed, "Oh Twilight, you're the tastiest thing I've ever had!"

Her comment did not sit well with Lighthoof but rather than saying anything, an idea crossed her mind. She wasn't sure how they would react to it but had fantasized about it. Once she noticed the two were so lost in one another that they wouldn't notice, she crawled up on the bed and stood over them. She spread her legs wide and began to pee on them. As soon as the warm liquid struck them, they both stopped sucking and gasped, "What? What was that?"

They both looked up to see a mischievous grin on Lighthoof's face. She looked down and said, "Shimmy, how dare you think someone tastes better than me!" She then turned her attention to Twilight and pouted, "How dare you taste better than me!"

Shimmy gave her a smile but Twilight broke down into a laugh before pulling Lighthoof down, "Oh so that's how it's going to be huh? You're going to be that naughty, huh?" She then knelt over Lighthoof and continued, "And you know all naughty girls must be punished, right?"

Lighthoof knew what was going to happen and replied, "Mhmm!"

Twilight then proceeded to give her a golden shower of her own. As she was releasing the liquid, Lighthoof exclaimed, "Oh it feels so good, it is so warm!"

Twilight giggled, "Oh so you like it?" Lighthoof nodded and Twilight continued, "You know girls, I'm getting kind of tired so how about all three of us take a little nap. After that, we can discuss your futures here."

"Our futures?" the girls gasped.

"Yes," Twilight replied "your futures or should I at least say your living arrangements." She laid back and finished, "For now though, you need to come and hold your Head Mistress tight. She does not wish to nap alone."

Immediately the two headed to Twilight and wrapped themselves around her. While they knew that they probably wouldn't have to worry about being expelled but did realize one thing, they knew that their days of living in the dorms were probably over and that Twilight probably wanted them much closer to her.

Epilogue: Planning the Future

Epilogue: Planning the Future

Three hours had passed and Twilight woke up to discover that Shimmy and Lighthoof were sound asleep clinging to her. Twilight was happy to see this but also knew that the time had come to discuss with the girls something very important, their futures. She nudged them and giggled, "Wakey wakey!"

The girls stirred some before coming to. At first Shimmy was a bit confused as to why she was in bed with Twilight, "Twilight, how did we get in your bed? Why are we in bed with you?"

Twilight could tell by the look in her eyes that she may have forgotten about their experience or thought it was a dream. Lighthoof was still a bit drowsy so Twilight nudged her again. She turned back to Shimmy and giggled, "Don't you remember, you and your sexy friend here were being very bad girls so your Head Mistress had to punish you!"

Once she mentioned the term "head mistress" she became more coherent and so did Lighthoof. Shimmy was curious about one thing, their futures, "So Head Mistress Twilight, what now? Are we going to get expelled?"

Lighthoof added, "Are you going to make us return home?"

Twilight pulled the girls closer and laughed, "Oh no, you girls won't be going home but you won't be living in the dorms, that is for sure."

Lighthoof asked, "Why and where are we going to live?"

Twilight had made plans for the two and was going to reveal them to them immediately. She pulled the girls up, unlocked her door and led them out. The girls were shocked about this and Shimmy was the first to speak, "Twilight, you're taking us out of your room naked? What are you going to do?"

Twilight laughed, "Oh I'm just going to show you your new living quarters."

Twilight continued to lead them down the hall until she opened a door on the left, the door to a bedroom. Twilight led them in and stated, "Girls, this will be your new bedroom. I am sure it will be to your liking."

The girls looked around and were pleased to see that it was twice the size of their dorm room. Another thing they noticed was that there was only one bed, which they took as a sign that Twilight had absolutely no problems with them engaging in their fun activities in her castle. Shimmy swatted Twilight's butt and giggled, "I take it we can have fun in here?"

Twilight swatted hers back and laughed, "Yes but you two can but to have this room there will be conditions.."

Lighthoof asked, "And what are these conditions?"

Twilight swatted her butt and giggled, "Ok, on school nights you two shall sleep in here but on Friday and Saturday nights, you shall sleep with me. You will also, regardless of when it is, submit to my desires, even if it is in the middle of the day on a school day." She stood behind Lighthoof, groped her breasts and continued, "And you two will put on shows for me on demand and if I so desire, you will not only allow me to record you but join in as well."

Both girls got smiles on their faces, "That sounds great Head Mistress Twilight!"

Twilight continued, "Oh and another thing, if I so desire, you will allow me to 'mark you.'" She then began to giggle, "And you girls can mark me too. After all, it wouldn't be fair for me to pee on you if you can't pee on me."

Both girls clung to Twilight and exclaimed, "We would love that!"

Twilight began to stroke her hands through their hair and finished, "And one more thing, if I decide that pop quizzes in my sleeping chambers are necessary, you will take them!" She broke into a laugh and added, "And you girls better not fail or I might just stop letting you mark me until you can pass!"

Shimmy giggled, "Oh you don't have to worry about us failing. We can tell what you like!"

Twilight gave the girls a smile, began to lead them towards her chambers and said, "Now lets get showered, get dressed and get your stuff out of your dorm. After all, I'm certain that it will be needed before too long."

Twilight led the girls back towards her chambers with a smile on her face. While she had always found the girls sexy, even before she should have, now that they were of age she could have them. Shimmy and Lighthoof were both happy. While they never dared to bring it up to anyone, they had been desiring to belong to Twilight for quite some time and now that their living arrangements were changing, everything they desired was coming to pass. Their desire to belong to Twilight had come true.