Learning To Laugh Again
A Cupcake Chronicles Side Story Series
by milesprower06

Part 5

Regardless of the fact that she was on vacation, Applejack simply couldn't resist the temptation. She missed farm chores terribly. She even learned from Apple Bloom that Filthy Rich had actually brought Diamond Tiara along for several days of helping out.

“And how did that go?” she had asked her younger sister.

“A lot better than I thought it would.” Apple Bloom told her.

So feeling the farm labor itch that she had gotten from being home, she took some baskets out to the north fields and harvested some of the remaining berries. The Ponyville region was due for a late winter, so she only had a couple more days before the snowfall began.

Since the temperatures were in the low 50's, Applejack was able to work a lot faster because she wouldn't be getting overheated. By the time she had come back to the house and gotten a bite to eat, everypony else was already in their rooms. When she walked down the hall to her room that she now shared with Rainbow, she found the Pegasus had returned while she was out working. She was laying on the bed, reading a book. She dropped her saddlebags and made a quick stop to the closet before coming over to the bed to see what Rainbow was preoccupied with.

“The Battle of Eternal Night: A Historical Chronicle” Applejack read the title aloud, finally getting Rainbow's attention out of the book. “Where'd you get that? Never took you for a reader.”

“After I finished meeting with the Princess, I got permission to make a quick stop in the Canterlot Archives. It's about the battle between Celestia and Nightmare Moon 1,000 years ago. My dad got the family heirloom today, an insignia band of my ancestor. Celestia told me he played a pivotal role in this battle.”

“Ah, so I suppose that's what you've got in that little chest there,” Applejack motioned towards the oak box on the floor next to the night stand. “So what'd the Princess want?”

“She...had a task for me to focus on...but not focus too much on that I forget to relax during my time off...it was rather confusing.”

“Uh-huh, so...one of those 'it'll happen at the right time' deals?”

“Something like that, yeah.”

“Couldn't she have said that to you in the letter?”

“Well, if she did that, then I wouldn't have gotten the lesson in family history. Besides, I'm glad she brought me up there to tell me. Any other way...and I don't think I would've liked it. I still don't think I like it yet...” Rainbow said, closing the book and setting it on the night stand.

“Well, why don't we snuggle up, and you can tell me all about it.” Applejack said, climbing into bed next to her marefriend.

“Well, when I first got there, I- hey what the-?”

In the span of three seconds, Rainbow found herself forcibly rolled onto her back, pinned, and had a red rubber ball gag forced between her jaws.

“On second thought, you talk too much.” Applejack said, her tone and demeanor instantly becoming much more aggressive and authoritative. As she fastened the strap around the back of her head, Rainbow instantly knew it was time to play. Rainbow mumbled incomprehensibly through the gag as Applejack quickly and expertly bound her front legs together with rope.

“You hush up.” Applejack sternly told her, rolling her over on her stomach. She gave her a quick barehoof smack on the flank.

“Present, my pet. It's time for a test.”

Rainbow did as she was told. Keeping her front bound legs tucked underneath her chest, she raised her flank up by bringing her back legs to a standing position, flicking her tail with anticipation.

“Tonight will be a test of endurance. As your mistress it is my place to train you. My first requirement of my pet is self control, something I remember you lacking during our first session. So you're going to improve.” AJ instructed, gliding the tip of her hoof up Rainbow's slit, eliciting a muffled moan from the Pegasus, bringing her wings to attention.

“It's so cute how you quiver at my touch, sugarcube. It's perfectly okay to love and enjoy your mistress pleasuring you, but it's not okay to orgasm without my expressed permission. If you want to cum, you have to earn it. Doing so without my permission will have consequences, understood?”

Rainbow nodded. As she felt Applejack sit down, tucking herself between her legs, wrapping her front legs around her flanks, she shuddered as she felt her hot breath on her swelling marehood, having a good idea of what was coming next.

She felt the farmer's tongue prod her flower, starting at the bottom, drawing up to the top. Rainbow whimpered through the gag as Applejack took her time in tasting her, not going deep enough fast enough. But she remembered her punishment in Las Pegasus when she tried to preempt her mistress, so she tried her best to relieve her tension through her whimpers.

'You belong to your mistress.' she told herself, immersing herself as deep as she could in her submissive mindset. Another whimper escaped from around the gag, as AJ licked up her slit again, not going any noticeably deeper, and teasingly avoiding the clit.

“Mmmm, my pet tastes good tonight.” Applejack said softly, after withdrawing her tongue. She sensually rubbed Rainbow's cutie marks within her grasp, kissing her inner thighs. “This is a treat best enjoyed slowly.” she added, putting another soft kiss directly on her clit, adding more fuel to the fire in Rainbow's stomach. That last kiss made Rainbow squirm, but she did not her legs, nor did she grind her hips into Applejack's light caresses and kisses.

Being ordered not to cum when being teased so slowly by somepony you loved so deeply was a tall order, but it was not as tall as Rainbow was being led to believe. Between their night at the hotel in Las Pegasus, and right here in her bed, Applejack had discovered one of her newest and biggest turn-ons.

Making Rainbow squirm.

It wasn't just that, either. It was the sounds too. Unable to speak with a dildo or gag in her mouth, the only way she could make her pleasure known was through muffled whines and whimpers. Knowing it was her own touch and tongue that prompted those sounds...she liked that.

Impressed with how Rainbow was enduring so far, AJ decided it was time for a curve ball. She wrapped her lips around Rainbow's clit and gave a short vigorous suck with a flick of the tongue.

That turned out to be a mistake. Rainbow jolted, her wings fluttering as she squealed into her gag, and Applejack got a hint of the undeniable taste of climax.

“What did I say abut cumming, pet?”

Rainbow simply panted through her gag, drool dripping off the bottom onto the sheets.

“Guess I'll have to show you that there are dire consequences for disobeying your mistress.” Applejack said sternly. Moments later, Rainbow felt something press against her marehood. Fresh from her climax, there was no resistance as AJ pressed the wired object into her. Judging by the shape she felt her sex clenching around, Rainbow concluded that AJ had just put an egg vibrator in her. With the control laying on the bed next to her left leg, AJ flicked it to low, which did little more than tease Rainbow, and make her want more.

Rainbow saw the tip of a hazel switch come into her gaze. She felt her flanks ache in anticipation. Switches cut through the air like nothing else, and the sound they made did not carry very far, no matter how hard they made contact. Lastly, their near-silence spoke nothing of the lingering sting they left. It wasn't as quite as effective as the leather strap she had used during their first session, but with the switch, Applejack could punish the gagged Rainbow as severely as she wanted, and the rest of the house would be none the wiser.

“Cut fresh just this evening, because I know how new you are to this, and I was sure you'd need some correcting. Twenty for cumming without permission, and keep presenting through all twenty.”

Rainbow did as instructed. Positioning her bound front legs underneath her chest, she rose her flank in the air again, head resting on the bed. She flicked her tail up, so it was off to the side, brushing against her left cutie mark, out of Applejack's way.

As much as she tried to anticipate it, she was not mentally prepared for the sting of the first swat. She gave out a muffled yelp, and her back left leg dropped to a knee.

“Add five for breaking posture. Get back into position, now.”

Rainbow immediately returned her leg to its standing posture, and was now more prepared for the pain as she endured hits two through six of the new total of 25, giving out little more than short cries that were effectively muffled by the ball gag.

Applejack understood the yelps; the switch left quite an impression. What surprised her were the brief moans of pleasure between each hit, vibrator or not. Rainbow's marehood was glistening with fresh arousal, and each new lash brought out another few drops down her thighs. AJ couldn't wait to be done with this and snuggle up next to her love for the night. But she needed to complete the punishment; a mistress mustn't appear soft. But on the tenth hit, Rainbow's right leg gave out ever so briefly before she corrected her posture again.

“Five more.” Applejack stated moments before coming down for the eleventh blow, as twenty-five became thirty.

As she worked through the high teens, Rainbow's rear was beginning to bruise. When she hit twenty-five, the light red marks had joined to form splotches of dark red, contrasting frighteningly against Rainbow's cyan coat. On twenty-five, she faltered in the home stretch, and her moans were increasing right along with the yelps. Eying her swollen vagina, AJ knew that Rainbow was getting close again. As she broke into the low 30's, her lover's entire body was quivering. Sure enough, on the thirty-fifth and final blow, Rainbow squealed into her gag, as the walls of her marehood convulsed, and she actually managed to ejaculate, squirting her juice onto the sheets in front of AJ as she came a second time.

Without any assistance from Applejack in maintaining her high, Rainbow descended from her peak rather quickly. After switching the vibrator off, Applejack walked around to where she could see Rainbow's face, and the panting Pegasus' gaze immediately held firm to the sheets in front of her.

“You know you deserve another set of twenty for that. But you know you have a very loving and merciful mistress, isn't that right?”

Rainbow nodded, tears flowing from her eyes.

“You love your mistress so much that you even get off on her punishing you. I know you're still learning. You're not going to be perfect overnight. You nearly doubled your initial punishment because you couldn't hold still, yet you managed to keep presenting even as you came all over my bed. You seem to have learned the importance of holding your posture.”

Rainbow sniffled from the tears, and shuddered in the aftermath of the orgasm.

“Besides, if I gave you what you deserve on top of those bruises, they probably wouldn't disappear by morning, and then everypony would know what a bad pet you are and how hard of a time you have with following instructions. Everypony makes mistakes, and overall, you have pleased your mistress. So now before bed, you're going to please me one more time.”

With that, Applejack walked behind Rainbow, and climbed atop the presenting mare. Positioning her own slit against the base of Rainbow's tail, she began to grind herself against her backside.

Applejack was much quieter in her lovemaking than Rainbow was overall, gagged or not. She was already quite heated, and she knew that this wouldn't take long at all. Rainbow merely rode it out, as Applejack ground her marehood against Rainbow's tailbone. Only her breathing increased as she neared climax. Rainbow wondered how she remained so controlled. Sure enough, as eating Rainbow out then punishing her to a second climax had already pushed her close, it only took a minute of grinding against the Pegasus to send her over the edge. With a gasp, Applejack suddenly increased the pace and pressure of her thrusts, alternating between fast and slow to prolong her orgasm as long as she could. She felt Rainbow shudder underneath her as her climax seeped down around the base of her tail, rolling down her flanks. Then with one final thrust, she collapsed on top of Rainbow, wrapping her legs around her and pulling her down into a laying position.

“Very good, Rainbow. Very good. Sooner or later you have to tell me why you enjoy that so much.”

AJ didn't get an answer, and the steady rising and falling of Rainbow's chest was a sign that her dreams had already taken her, as she steadily breathed through her nostrils. She was always a heavy sleeper, so she didn't wake up as Applejack gently unfastened the ball gag, and very slowly pulled the vibrator out. She decided to leave her front hooves tied up, so Rainbow could have an instant reminder of the fun they had the night before. Rainbow kept sleeping as she got a soft kiss on the cheek. But for AJ, her mind kept her up for several more minutes. Rainbow achieving a second climax just from being hit was certainly the biggest surprise of the night. She knew that she enjoyed being a dom, no doubt about it. Controlling a brash, egotistical pony like Rainbow, making her squirm...yes, she liked that very much. As she read it more about it, she believed she was getting better with every session she and Rainbow had.

But there was that hint of curiosity. She wanted to know what made Rainbow enjoy it. The book that Twilight lent her offered her little in the way of specific answers:

Subs get their thrill in a variety of ways. Some like being controlled. Some like testing limits and rules; being disobedient and subsequently punished. Some enjoy just being nothing more than a bucktoy. No two subs are exactly the same. The more you know your sub, and the more time you spend with them in sessions, you will inevitably learn what makes them tick.

Tonight was their second session, and Applejack had gotten only one obvious answer: that Rainbow was enjoying it immensely.

Well, there was always the next session, or the next chapter of Twilight's book.