Lessons Learned
by Nom deCheval
“I’m telling you it was something else!” he said, his chest thrust out. “That mare was all over me like she was in heat! Didn’t matter what I said or did, it got her worked up like you’ve never seen. By the time I stuck my dick in her, she came in like, ten seconds flat!”
“Sure...” his friend answered. The other stallions with him began to laugh.
“I’m serious!” he defended. “Do not doubt the power of my stud ability!”
This only sent them into a deeper state of laughter.
“Right!” one of the others replied. “Is this the same ‘stud’ that stumbled over his own words when talking to that mare at the lake last week? The same one that ran out of the club the other week after a mare was a little too forthcoming with her thoughts towards him? THAT ‘stud?’”
“Hey now! None of you can say that you haven’t had bad days either!” He pointed his hoof in an arc, gesturing to them all. “So don’t look to past experiences when I tell you about last night!”
“So we’re supposed to believe that you nailed this mare and shook her world?” his friend asked.
“I’m telling you! Why don’t you believe me?” he asked.
“Excuse me?” a soft voice asked.
They all turned to see a deep reddish-pink mare with a light rose mane standing nearby. A pleasant smile was on her face and her eyes lit up easily.
“Oh, hi Miss Cheerilee,” the stallion said. “What can I do for you?”
“I hate to be a bother, but I was curious,” she began, “this mare that you’ve been boasting about, what was her name?”
His cheeks turned crimson, and all of his companions suddenly found themselves turning away and acting as though something extremely interesting was happening very nearby.
“Uh...well, I didn’t mean to offend you, ma’am,” he fumbled through his words.
“Nonsense. You were bragging about a conquest, as boys are prone to do, and I just happened to overhear you. No need to feel embarrassed,” she explained. “Just tell me the name of the mare, please.”
“Uh,” he brought his hoof up and began to rub the back of his head. “I’m not sure I should do that. I mean, I don’t want to be known as a guy who was spreading around the name of a mare that way.”
“Weren’t you just bragging about her?” she asked.
“I guess so,” he answered slowly, “but I never told any of these guys her name.”
“You still don’t have to,” she suggested with a smile. “In fact, why don’t you just whisper her name to me. I promise to keep it a secret.”
“Wouldn’t that pretty much be the same? I mean--”
“Young man!” She stamped her hoof, cutting him off. “I will not ask you again! You tell me that mare’s name this instant!”
He gulped and leaned over to whisper a name.
* * * * * * *
In a blur, she skidded to a landing, the wind she created catching up to her a moment after she came to a stop, sending her mane and feathers ruffling.
“Oh yeah!” Rainbow Dash said excitedly. “Outrunning my own breeze! Now that is speed!”
She glanced around quickly, trying to find somepony else to brag to about her accomplishment. Seeing no pony, she simply did a quick hoof pump for her own gratification.
With a strut, she trot over to her destination, a small building on the outskirts of town. She stepped inside without knocking, spying the sole pony inside immediately.
“Heya, Miss Cheerilee!” Dash announced. “What’s up?”
“Oh, Rainbow Dash,” Cheerliee answered as she turned to face the pegasus. “I didn’t hear you come in.”
“Oops. Sorry about that one,” she answered. “I got your note. What did you want to see me about? Are you hoping that I can teach the kids about how to be more awesome?”
Letting out a light chuckle, Cheerliee shook her head. “No, nothing of the sort. I do want to thank you for coming by this afternoon, though.” She moved over to and past Rainbow Dash, shutting the door into the schoolhouse.
“Not a problem!” Dash answered. “Always willing to help out.”
“I’m so very glad to hear that,” Cheerilee answered as she moved from window to window, closing them tight and pulling down the shades. “I do hope that you haven’t got anything planned for the afternoon, either. I’m afraid that this may take a while.”
“Nah. I’m off from weather patrol duty until tomorrow. Ain’t got nothing planned for the whole day,” Dash answered.
“Oh, that’s excellent news,” Cheerilee moved back over to her desk, walking behind it and opening a drawer. Rainbow Dash looked about, noticing how sparse the walls were. No decorations of any sort.
“Are you needing some help putting up stuff to make the room look better?” Dash turned a full circle, seeing nothing on the walls. “The place is looking a little bare.”
“Oh, no. The children are out of school for the next five weeks. It’s time for their summer break,” Cheerilee explained.
“Ah, yeah, I guess so. Hadn’t thought about it,” Dash answered, still staring at the walls, oblivious of Cheerilees actions.
“So, uh,” Dash scratched the back of her head, “why did you ask me over today?”
“To teach a lesson,” Cheerliee answered.
“I thought you just said that the kids were out of school for a few weeks,” Dash replied.
“I did,” she stated, “but I never said it was a lesson for the children.”
“What?” Dash twisted her head in confusion.
“Are you aware that you have a rather strong reputation in Ponyville, Rainbow Dash?” Cheerilee asked.
“Sure I do!” She pushed out her chest. “For being amazing, spectacular, and just downright awesome!”
“Well, I guess there are some of the children who say that about you,” she answered. “Do you know what the adults, specifically the stallions in town, are saying about you, though?”
“Uh,” Dash thought for a moment. “Same thing, isn’t it?”
“Not exactly.” Cheerilee walked from around the back of her desk, her appearance raising an eyebrow on Rainbow Dash. She was wearing fishnet stockings on all four legs, with shiny black shoes over tops of her hooves and fetlocks. In her mouth she carried a bridle with a thick black bit on it.
“Woah!” Rainbow Dash stepped back. “That’s...quite an outfit Miss Cheerilee.”
“First off, Rainbow Dash,” she explained, setting the bridle down on her desk, “it’s Mistress Cheerilee. And secondly,” her tone turned cold, “get over here!”
“I, uh, gotta go,” Dash said. “I just remembered that I--”
“Rainbow Dash!” Cheerilee stamped her hoof. “I will not tell you a third time! Get over here!”
“Yes, ma’am,” Dash answered meekly and slinked over next to the other mare.
“Very good,” Cheerilee stated when Dash was standing next to her. “Now, you don’t know much about me as a teacher, being from Cloudsdale and all, but let me explain one thing to you: with foals I am understanding, but with adults I am very, very strict. Is that clear?”
“I don’t think that I--”
“I asked you a question, young lady!” Cheerilee interjected.
“Yes, ma’am,” Dash answered again.
“Excellent,” Cheerilee smiled. “Now, as I was saying, you have a bit of a reputation in town. Since you don’t know what that is, I will tell you.” She looked directly into Rainbow Dash’s eyes, and the pegasus suddenly felt surprisingly small. “It’s that you are an easy lay.” Dash blinked at the surprising statement. “And worse, that you have an orgasm from almost anything. Is this true?”
“I...uh, well, I...” Dash stammered. Then she shook her head and looked at the other mare. “Now wait just a minute! Who the heck is saying that about me? I’m not easy!”
“Several stallions are saying it about you. I’ve heard it personally, so this isn’t coming as second-hoof information,” Cheerilee stated. “Reputations like that are a bad thing, Miss Dash.”
“I didn’t think that I slept around THAT much...” Dash mumbled.
“What about the other part?” Cheerilee asked. “How good is your stamina?”
“Huh? Well, I don’t know. I can go for a while, I suppose,” she answered. And then cocked an eye. “Uh, and this conversation just got weird, by the way. Are you...are you hitting on me?”
“Do you not like mares?” Cheerilee asked.
“It’s not that,” Dash answered. “I mean, I’m fine with mares. I don’t consider myself all that picky. It’s just...weird.”
“Well, you answered one of my questions perfectly,” Cheerilee stated. “You aren’t that picky.” Cheerilee stared daggers into the pegasus. “You should be. As a mare, it is you that is in control. Stallions are easy creatures, and if you do things right, they are easily handled.”
“Uh, okay,” Dash replied. “What about mares?” She followed that up with another mumble, “And why am I asking this?”
“Mares are a different story. Two mares that are together can experience a far more enduring encounter, based on mutual satisfaction,” she said. “And as to why you are asking, well, it’s because I’m a teacher. I’m here to educate you.”
“E--educate me?” Dash asked with a gulp.
“Don’t be so overly dramatic,” Cheerilee scolded. “I won’t do anything that you do not agree to. I will tell you, though, that if you give me full leeway, I can help you reach newfound heights in both skill and enjoyment.”
Dash blinked a few times.
“Wait,” she stated, “are you telling me that you want to teach me how to have sex? Me? You want to teach the amazingly awesome Rainbow Dash how to have sex?”
“No,” Cheerilee corrected. “I want to teach you how to have better sex.”
“And...what do I have to do?” Rainbow asked curiously.
“Everything I tell you to do,” Cheerilee responded.
“And if I don’t?” Dash asked.
“Then you will always wonder what you are missing,” she answered.
Dash looked away, her mind racing. Her eyes darted back and forth, her lower lip found its way between her teeth, and she stood there trying not to dance around on her hooves.
“Okay!” Dash blurted out. “I’ll do it!”
“Excellent,” Cheerilee stated. “Now, the first thing that you need to know is that your safeword is ‘blackboard.’ If you say that at any time, I will stop immediately. If you cannot speak, I want you to tap my leg or the ground four times in rapid succession. Is that clear?”
“I guess so,” Dash answered. “But why would I need to--”
“Shush!” Cheerlee stepped up, standing over Dash with authority. “You do not question you lessons! You answer when I tell you to, and only then! If you speak my name, you will address me as Mistress Cheerilee or simply Mistress.”
Dash opened her mouth to answer, but thought the wiser of it.
“Excellent,” Cheerilee said with a smile. “You’re learning already. Now, let’s start with this reputation of being the fastest mare in Ponyville.”
“Aw yeah!” Dash couldn’t help herself. Cheerilee raised an eyebrow.
“As a reminder, Miss Dash, I will discipline you if I feel it is necessary,” she said calmly. “Now, being fast is not always a good thing. You have the reputation that you reach an orgasm in a mere ten seconds. Is this the case?”
“Uh, I guess. I don’t know,” she answered. “I never time myself there, but I do really get into it, and cum pretty darn quick most of the time.”
“Unacceptable!” Cheerilee stamped her hoof. “While it is good to reach an orgasm--for both yourself and your partner’s benefit--doing it quickly tends to make the other participant feel there is nothing of a challenge to you. They will lose interest very quickly.”
“Lose interest? In me? Ha! Not likely!” Dash boasted.
Cheerilee stood there coldly, staring at Rainbow Dash without moving. Without a thought, Dash lowered her eyes.
“I see now that you are going to be unable to control yourself without help,” Cheerilee said, turning back to her desk. She grasped the bridle with her mouth and stepped behind Rainbow Dash. In a single swift motion it was around the mare’s head, the bit firmly lodged in the pegasus’ mouth. “If you behave yourself, this may come off. Until then, it stays on.” Moving to a nearby chair, Cheerilee pointed in front of her. “Come here!”
Slowly, Dash walked over to her, her ears back and her eyes slightly closed. Before she knew what was happening, a hoof flashed out and grabbed her, pulling down across the teacher’s lap. Just as quickly, a hoof came down on Dash’s flank.
“Disobedience is not tolerated, Miss Dash,” Cheerilee explained as another hoof came down on the meaty part of Dash’s rear. Her eyes looked like saucers as Cheerilee’s hoof slapped repeatedly against Dash’s ass, her flesh shaking with every impact. Dash felt a dampness suddenly growing between her legs.
And just as suddenly as it started, Cheerilee pushed Dash off her lap.
“Now, step up to the desk!” Cheerilee stated.
A quick slap on the flank encouraged Dash to take the short walk.
“Front hooves up on the desk,” Cheerilee instructed.
There was a brief pause, followed by another slap on the flank. Dash moved her hooves up to the top of the desk, scooting a little forward. From the corner of her eye, Dash saw Cheerilee moving around to stand in front of her.
“Slide your hooves forward,” she instructed. This time, Dash obeyed without question.
“Good. It makes it so much easier on both of us if you just follow instructions,” Cheerilee smiled. She then reached down and pulled up a section of rope. “Now, hold still.”
Her eyes bugging out, Rainbow Dash swallowed hard as the rope looped around her fetlock, a knot pulling it tight to her flesh. Her hind legs shifted, squirming unexpectedly, feeling a wetness building. A moment later, another rope tied her other leg down. She pulled on the rope, testing it, but there was little give, and no getting loose.
“Now that I have your complete attention, we can proceed.” Reaching into one of her desk drawers, Cheerilee pulled out a long, flexible object shaped exactly like a horse cock, with straps and buckles meant to hold it in place.
Her eyes danced along the length of the phallus, measuring the size of the thing visually as Cheerilee stepped into the straps and brought her head around to tighten it snug to her body.
“Now the real instruction can begin,” she said with a smile.
Dash followed her as the mare walked around behind her, the long, thick toy bobbing between her legs.
“Eyes front, Miss Dash,” Cheerilee said without turning her head. Instantly, she snapped her head around, focusing her eyes on nothing in particular, all of her interest still behind her.
“Legs apart.” The words were like a shot. Softly spoken, she obeyed them instantly, and as she did she felt something ease down her leg. Her marehood was drenched.
A moan was her only response when she felt something delicately caress her nether opening. She closed her eyes and lowered her head, letting her ears go flat to her head.
“I was wondering if I was going to need to get you ready,” Cheerilee said, her hoof working across Dash’s slit, “but obviously that isn’t going to be an issue with you.”
Dash pressed backwards when her sex was left suddenly untouched.
“I feel like this is a pointless task, but we have to test theories before they are proven correct, don’t we?”
Something pressed against the opening to Dash’s marehood, as she heard Cheerilee's hooves settle on either side of her on the desk. She knew in her mind exactly what it was, but she still wanted to turn around and look, just to see the toy as Cheerilee wielded it. Dash kept her eyes forward, letting her mind see for her.
She imagined the head of the thing pushing its way inside as she felt it part her lower lips. Her brain saw the length of the shaft slowly disappearing with the sensation of it filling her up. Drool began to well up around the bit, falling down onto the desk beneath her as Cheerilee started to move the fake horse cock in and out of her pussy.
With a shudder, Rainbow Dash came, her juices sluicing around the dildo in a torrent of cum.
Unceremoniously, Cheerilee pulled out of the spent mare. “Ten seconds flat,” she said coldly. Walking around to face her directly, Cheerilee shook her head and pulled the bit from Dash’s mouth. “I was hoping it was an exaggeration, but that was very disappointing.”
“Huh?” Dash looked up at her, eyes glazed over.
“Your endurance is pathetic,” she stated. “You lasted a mere ten seconds.”
“What guy wouldn’t like that?” Dash asked with a smile.
“As the news gets around, Rainbow Dash, this becomes less about how proficient a stallion is, and more about how slutty you are.”
“I’m not a slut!” Dash announced.
“Perceptions make reality,” Cheerilee explained. “And do not raise your voice to me, young lady!”
“Aren’t we done?” Dash asked.
“Done?” Cheerilee shook her head. “That was just to test the hypothesis. Now is when we start to find a solution to the problem.”
“Solution? Wait, what are you going to do?” Dash asked.
“Simple. I’m going to fuck you again. And again. And again. Repetition makes mastery, and we will practice this all night if we have to, until you learn to control yourself,” Cheerilee said as she trotted around behind the mare once more.
“Uh, not that I’m gonna complain about another good rut,” Dash stated, “but how’s this going to teach me anything?”
“It will teach you to be in control of your body, young lady,” Cheerilee said. “Let’s look at this another way, though. Think of it as a competition.”
“A competition?” Dash’s ears perked up.
“Yes. It’s not a race to see who finishes first, but a challenge to bring yourself to the highest level of pleasure, and to hold yourself there until your partner is ready to orgasm. The reward is you having the most spectacular orgasm of your life,” Cheerilee described.
“Oh yeah! I can do that!” Dash boasted.
“Prove it, then, Miss Dash. All you have to do is outlast me, and you will graduate from class,” she said.
“Wait,” Dash paused. “You are using that fake dick on me! There’s no way I can outlast you!”
“Giving up before even trying?” Cheerilee asked.
“It’s like you’re cheating!” she stated.
Moving up behind the mare, Cheerilee directed her hoof between Dash’s legs, rubbing against the outside of her slit. “It’s nothing of the sort, Miss Dash. This device strapped onto me has an end that inserts into my own vagina. I feel every thrust that I make.”
“So, you can cum from this?” Dash asked.
“I can,” she answered.
“Oh yeah! Now we’re talking,” she turned her head around to look back towards Cheerilee. “Give it your best shot, babe!”
A single eyebrow went up on Cheerilee. “Respect, Miss Dash. It seems that I am going to have to remind you that you are to call me Mistress.”
“Earn it!” Dash curled up her lip, shaking her hips towards the dominant mare.
“I could say the same of you,” she replied.
“Well, you’re the one that wanted me to learn something, right? Well...teach me!” Dash pushed backwards trying to rub her flank against Cheerilee.
“I give you another ten seconds,” she answered, maneuvering to align herself hips with Dash’s entrance. “And if I’m right, then we will have to begin your training in earnest.”
“Yeah, yeah,” Dash answered. “Less talk, more rutting.” Another thought came to mind. “Oh, and WHEN you cum before I do, then you have to apologize to me and...and something else, too. I’ll figure it out then.”
Deciding not to deem that with an answer, Cheerilee lifted her hooves up, placing them on either side of Rainbow Dash’s body. She slowly moved her hips forward, until she felt the resistance of Dash’s flesh.
“C’mon! Stick that thing inside me,” Dash urged. “That is, unless you’re already afraid that you’re going to lose.”
In a single, deep thrust, Cheerilee plunged herself deep inside Dash’s already sopping cunt, burying herself until her hips struck against Dash’s.
“Oooooh!” Dash cried out, her eyes bulging.
“Too fast, Miss Dash?” Cheerilee grinned.
“H--heck no! Just...just getting myself comfortable,” she defied.
“Well, don’t let me stop you,” Cheerilee began to move her hips in a tight circle, rubbing the inside of Dash’s walls with her phallus. “Get as comfortable as you would like. Oh, and you have about five seconds left.”
“O--oh yeah?” Dash was already panting. “W--well, that...that...that’s not gonna...be long enough!”
“Two seconds,” Cheerilee stated.
“Ahhhhhh.” Dash shut her eyes tight and bit down on her lip--hard. She felt her walls spasming, contracting tight against the teacher’s toy, but she fought every moment of it. For the first time that she could remember, she was trying not to have an orgasm.
And then the motion stopped. Dash spun her head back to face Cheerilee, and was greeted by a wicked smile.
“Congratulations,” she said, “You’ve passed ten seconds.”
“Aw yeah!” Dash shouted.
“You won’t outlast me, though. You barely outlasted a short timer,” she boasted.
“Still only hearing talk, lady!” Dash answered.
Pulling her hips back slowly, Cheerilee once again thrust forward, driving her phallus deep into Dash’s waiting pussy. She ground her hips against the mare, leaning forward to whisper in Dash’s ear. “Are you the type of slut that likes it hard and fast, or slow and grinding?” There wasn’t a long enough pause for Dash to answer. “Nevermind. Fast is all you know. Well, there are other things besides a quick fuck, Miss Dash. I am going to show you one of these, just as an example.”
“Oh yeah? Can’t take my speed, ehhhhhhhhHHHHH!” Teeth bit down on the shank of Dash’s wing, just firm enough to send electric jolts racing through her body as Cheerilee slowly pulled herself out, and then deliberately drove herself back inside at the same tempo.
“Now that you’ve lasted more than ten seconds, let’s see if you can make it a full minute,” Cheerilee stated, releasing Dash’s wings.
“I...I can if you stop...cheating!” Dash growled.
“Cheating?” Cheerilee’s voice was steady.
“No wing biting!” Dash shouted.
Cheerilee stopped her hips.
“Did you just raise your voice at me, Miss Dash? Again?” Cheerilee asked. “That is not something I tolerate in my classroom!”
The pounding began. Without hesitation, Cheerilee began to drive the fake cock deep into Dash, relentlessly thrusting in and out of her marehood. Dash’s eyes rolled back into her head, her mouth hanging open wordlessly.
In less than eight seconds Rainbow Dash came all over Cheerilee’s toy.
The teacher didn’t stop. She continued to drive into the mare’s pussy, her hips working with precision as she drove the phallus to the hilt each time. Twenty-three seconds later, Dash felt her whole body quake and quiver as she orgasmed for the second time. And then again in seventeen seconds. And again after thirty-two. And once more after another nineteen had passed.
“St--stop,” Dash whimpered, her body starting to feel the strain. “Please, stop.”
“Address me properly, Miss Dash, and I will,” she said, her hips still working pendulously.
“Stop, pl--please, Cheerilee,” Dash begged, her body suddenly wracked with another orgasm.
“Properly, Miss Dash. Properly,” Cheerilee instructed calmly.
“Pl--please stop...Mistress Cheerilee!” Dash groaned.
Just as suddenly as she entered her, Cheerilee pulled herself free, and Dash collapsed on the desk.
“Very good, Miss Dash,” Cheerilee stated as she bent down and loosened the straps on her phallic device. With another tug, it pulled free, and she walked around and sat it down behind her desk. “Now, that wasn’t so hard, was it?”
Rainbow Dash looked up, her eyes unable to clearly focus. “Huh? What?”
“You did very well, Miss Dash. I was impressed,” Cheerilee said.
“I did what now?” Dash squinted at the mare, trying to make sense of what she was saying.
“Well, your reputation was clear, and a single test proved that theory to be most likely true,” Cheerilee said, “but you proved yourself very willing to learn. Very willing to take instruction.”
“But...but I never even got you close to cumming,” Dash said weakly. “I lost.”
“There are no winners and losers in education, Miss Dash. Besides, you were never going to be able to give me an orgasm if I didn’t want it to happen. That only occurs when I am ready. When I let myself reach that plateau.”
“You...you don’t ever cum?” Dash asked.
“That’s not what I said, Miss Dash,” Cheerilee said with a smile. “I said that I only cum when I let myself cum. When I want to. And, just like you, I can orgasm many, many times, but at my own rate. I can outlast any stallion.”
“Really?” Dash watched Cheerilee reach down and loosen her bonds. Rubbing her fetlocks, Dash pulled back and stood on the floor next to the desk. “Is there any way you could teach me that?”
“That was the whole point of this exercise, Miss Dash! To test you and see if you had what I was looking for in a student,” Cheerilee stepped back around to stand beside Rainbow Dash.
“You tested me by fucking me?” Dash’s face twisted up.
“Well, I couldn’t just ask you, could I? Watching your reaction was far more important to seeing how well you would work as a student,” Cheerilee said.
“And I failed,” Dash shook her head. “I came so many times I think that I’m dehydrated.”
“Don’t be ridiculous!” Cheerilee said. “I already told you that you did very well. I was quite impressed.”
“Huh? I don’t get it,” Dash said.
“Your body is trained to do one thing, but you fought against it. You showed a willingness to learn and change, and that’s the key. No pony ever learns everything in a single lesson. You’ll make an excellent student,” Cheerilee said calmly.
“I thought...” Dash stopped herself. “I mean, this isn’t a one-time thing?”
“Only if you want it to be,” Cheerilee said. “Otherwise, I’m offering you private instruction. In time, you’ll be able to control yourself as well as I can.”
Dash’s eyes lit up.
“Oh yeah! Now that would be cool!” Dash flitted up into the air in excitement.
“All you have to do is say the magic word, and it will happen,” Cheerilee said.
Dash glanced around the room, her mind trying to capture the secret.
“Uh, please?” She said with no confidence.
“No. You know what it is,” Cheerilee said with a smile.
“Huh?” A spark lit in her eye. “Oh!”
Dash smiled playfully. “Please...Mistress Cheerilee?”
Class was back in session.
The End.
