Casual Sexquestria

by Frizzy

A Helping Hoof

Previous ChapterNext Chapter

Cheerilee weighed her options, carefully. Sure, Trixie's ass was deliciously round and soft, but Rainbow Dash's had a wonderful firmness to it with the perfect balance of shape. She pondered her choices for another moment, giving both flanks another squeeze, before finally tossing a bit into Rainbow Dash's jar.

"Yes!" The athlete cheered. "Suck it, Trixie!"

"You haven't won, yet, you overgrown pigeon," Trixie retorted. "This contest has only just begun. We have all day for ponies to realize that Trixie has the superior behind. When we're done here, Trixie will use that spell Sparkle taught her last week, and I assure you, you will be the one sucking it."

"Well, have fun, you two," Cheerilee said, waving the two competitors goodbye. "I wish you both the best of luck in your competition, but I really must be going."

"Uh huh," Trixie said, dismissively, offering a short wave in return.

"Yeah, see ya, Lee!" Dash replied, waving more enthusiastically, a grin plastered to her face. "Just remember, this ass is yours whenever you want it," she seductive wiggle of her rump.

"I'll keep that in mind," Cheerilee said, turning around to continue her errands. In all honesty, while Rainbow Dash did have the nicer butt of the two, Trixie would have easily won, had this been a contest on who was the better fuck. Sure, she barely did any of the work, but she was an excellent dom, when Cheerilee had that particular itch. Dash would typically try to rush it, then gloat about how awesome it was. She required very firm discipline, if they were to both reach satisfaction (and last more than two minutes).

Speaking of a good fuck, that was exactly what the schoolteacher needed. Fortunately, she had planned this particular errand for last for this very reason. She needed to pick up her bi-weekly supply apples and everypony in Ponyville knew that Sweet Apple Acres had the best apples this side of Equestria. Plus, it didn't hurt that either Applejack or Big Macintosh were usually up for a quick roll in the hay.

As she approached the Apple family's stall, she saw that it was being tended by Mac, much to the the fuchsia mare's delight. "Oh, Big Mac!" she called, with an extra bounce in her trot. The stoic stallion turned his head to meet her gaze, giving her a friendly smile. "Are you doing well, today?" she asked, adding a subtle sway to her hips.

"Eeyup," came his typical response.

"That's good to hear," Cheerilee replied. "I was hoping to get one dozen Granny Smiths, a half dozen Fuji, three Winesaps, and three Pippins. Also, I was wondering if you would..." she trailed off when she heard a strange sound coming from beneath the table.

GLRK GLRK GLRK GL-

The sound was quickly interrupted by a series of wheezing coughs. Cheerilee gave a knowing smirk. "Sugar Belle?" she whispered.

"Eeyup," Big Macintosh whispered back.

"Mind if I...?"

"Nnope."

Cheerilee smiled, walking around the stall's counter, and crouching down. Sure enough, Sugar Belle was lying down between Mac's legs, taking deep, wheezing breaths, while tears rolled down her face, and thick strands of saliva connected her mouth to her husband's throbbing erection.

"Hi, Sugar Belle!"

"Hey, Cheerilee," Sugar Belle replied, smiling. She wiped away a few strands of spit and tears.

"Still having difficulty taking all of him?"

"Yeah..."

Big Mac, true to his name, was huge. His cock was easily as long as one of his legs and just as thick. He was the wet dreams of many mares and the envy of all stallions.

"You know there's no shame in not being able to swallow the whole thing, right?" Cheerilee asked, placing a comforting hoof on her friend's shoulder, while her other idly stroked the topic of conversation. "Most mares have difficulty with it. Even Pinkie Pie can't get more than three quarters of it down, and even then she's struggling, which is saying something, since she routinely inhales entire cakes, and she's been Ponyville's Cocksucking Champion three years in a row."

"I know, it's just..." Sugar shut her eyes, tight, trying to hold back more tears, and slamming a hoof down in frustration. "I'm his wife! I should be the one who can handle the most, dammit! Yet, I can't even take a third of it without nearly suffocating!"

One of Macintosh's hooves began stroking her mane, trying to comfort his wife. "You know that don't matter to me," he said.

"It does to me," Sugar Belle grumbled. She half-heartedly raised her hoof and began to pump it along Big Mac's length, her hoof occasionally bumping into Cheerilee's.

"Hey, there's no reason to be upset," Cheerilee said, offering her friend a supportive smile. "So what if you aren't the best at giving blowjobs? None of the stallions particularly care and every mare in Ponyville knows that what you lack in oral skills with stallions, you more than make up for with your pussy eating! And don't even get me started on your ease with anal. If you want, I could teach you how to suck dick like a pro."

"You really think you could?"

"I don't have a teaching cutie mark for nothing!" Lee beamed. "Now, get your head up, mouth open, and stick your tongue out."

"Wike thith?" Sugar Belle asked, replicating the actions the teacher had just instructed her to do.

"Yes, excellent," Cheerilee said, rapidly jerking Big Mac's impressive cock. "Now, take just the tip into you mouth, and hold it there."

Sugar Belle did just that, looking to her teacher expectantly, awaiting further instruction. Cheerilee continued to give Mac a hoofjob, the virile stallion leaking precum into his wife's mouth, profusely.

"Run your tongue along the head," Cheerilee said, now using her other hoof to cradle Big Mac's testicles. "When you're ready, move forward."

Sugar Belle followed her teacher's guidance, swirling her tongue around Mac's throbbing glans, savoring the pre that continued to flow at a steady pace. Taking a deep breath through her nose and shutting her eyes in fear, Sugar pushed forward as quickly as she could. One inch, two inches, three, all slid passed her lips. The tip of Mac's cock quickly bumped into the back of her throat. Sugar Belle immediately pulled back, but was stopped after about an inch. She opened her eyes, seeing Cheerilee comfortingly smiling back at her, one of her hooves on the back of her head, preventing her from extracting Mac's gargantuan girth from her maw.

"Can you breathe?" Cheerilee asked, rubbing the back of the unicorn's head. Sugar Belle nodded, tears forming in her eyes. "Good," the earth mare replied. "I think I've figured out your problem: you're reckless. You put little thought into how you are going to get the penis into your throat and just try to force it in. When you feel yourself choking, you panic, and attempt to immediately remove it. You've got to take things slowly. Take a pause when you start choking, then keep going. When you're ready, keep going."

Sugar Belle took another deep breath, steeling herself for what she was about to do. She shut her eyes and pushed forward, this time at a much slower pace. She passed the point where she had failed last time, smiling a little around her husband's cock, as she did. She took another two inches, before the familiar feeling of too much meat in her throat started to take over. Another inch and a half was too much and she pulled back, losing an inch of progress. This time, Cheerilee wasn't there to keep her from removing too much of Big Mac's penis. Sugar opened her eyes, noticing that the fuchsia mare was gone.

A lick along the unicorn's puffy pussy answered the question as to where her teacher had gone. "You're doing great," Cheerilee said, giving another lick. "I'll be right here, if you need me." Sugar Belle moaned as Cheerilee dove back in, her wide tongue tracing up and down the earth mare's juicy slit, gently spreading the delicate lips, and teasing the swollen clit.

Sugar Belle took a moment to enjoy Cheerilee's expert mouth, before returning her focus to the task at hand. She cautiously pushed forward, regaining her lost inch, and steadily continuing onward. Another inch went down her throat when she began to choke, again. She didn't pull away, this time, opting to instead keep all of it in her mouth as she gagged, letting her throat grow accustomed to its guest.

Two more inches were swallowed, before Sugar Belle found herself pulling back, losing three. However, this time it wasn't because she was having difficulty taking Mac's cock. No, this time it was began she was caught off guard by Cheerilee's tongue probing against her ass. "Mmphm!" Sugar grunted, indignantly, lightly kick in Cheerilee's directions.

Big Macintosh chuckled. "Maybe a little warnin' next time, Lee?"

"I'm sorry," Cheerilee replied, sheepishly. "It was just so hard to resist getting a little taste when something so delicious was right there. How's it going, by the way?"

"Mmphm mmm," Sugar Belle grumbled, regaining her lost length.

"Well, you're certainly doing a lot better than before," Cheerilee praised, giving Sugar's tight asshole another lick. "You're almost halfway there. Keep it up!"

"Mmhmm," Sugar Belle replied as Cheerilee's tongue returned to her anus. Another inch passed her lips. The medial ring soon followed, along with another inch.

Big Mac patted his wife's head, affectionately. "You're doing good, honey," he said, as even more of his cock made its way down her throat. Sugar Belle hummed along his dick, the gentle vibrations stimulating him, further.

Meanwhile, Cheerilee hungrily licked Sugar Belle's asshole like it was the most delicious thing in the world. Her tongue pushed as deep as she could into the unicorn's tight plot, wiggling around in an effort to help her friend feel more relaxed. The poor mare may have felt inadequate at her inability to blow her husband as well as some of the other mares in town, and Cheerilee was doing everything she could to make her feel better about herself. From the look of things, she was already doing much, much better than she had been, and it was only a matter of time before she was rewarded with a hefty serving of her husband's love.

Cheerilee raised a hoof and began rubbing the other mare's winking sex, catching her clit and playfully teasing it. She split her focus between Sugar's tight tailhole and her rapidly pulsing pussy, which was leaking like a faucet at this point. Come on, Cheerilee thought, concentrating all of her efforts on the mare before her. Almost there!

"WAAHAAHAA!" Sugar Belle screamed around Big Mac's meat as her orgasm crashed over her. Her plothole tightened around Cheerilee's tongue while her pussy made a wet mess of the other mare's hoof. This was what Cheerilee had been waiting for. As the unicorn was distracted with her intense climax, Cheerilee shoved her head forward in a single, swift motion, forcing the remaining six inches down her throat. Big Macintosh's entire cock was now lodged safely in her throat, a feat no other mare had accomplished, before. Sugar Belle stared, wide eyed at her husband's hips, unable to believe what she had just done. She would have cheered, had her throat not been currently occupied by the biggest dick in Ponyville.

Cheerilee moved around, giving Sugar Belle a congratulatory kiss on the cheek. "Good job, Sugar!" she cheered, giving her friend another kiss, and rubbing the throbbing bulge in her throat. "Don't forget, you still aren't done, yet."

"Mphmm!" Sugar Belle agreed, moving her head back, slightly, then pushing forward, once again. Now that she had proven that she could handle the entire cock, now she had to finish what she started. She found a steady rhythm she could comfortably keep, always keeping most of Mac's impressive length buried deep inside her esophagus, and only occasionally gagging on it.

Big Mac hissed through his teeth, pumping his hips ever so slightly. "Cumming?" Cheerilee asked, looking up at him.

"Eeyup," he answered, right as the first wave erupted from his cock.

The first wave flowed directly down to Sugar Belle's stomach. Not satisfied with merely swallowing, she pulled back, wanting to taste her husband's delicious seed. The second wave splashed against the back of her throat, catching her off guard. She gagged, causing the remainder of Mac's cock to slide out of her mouth as she coughed up cum. The third wave blasted her in the face, preventing her from opening her eyes.

The fourth wave never came, however. Curious as to where her treat had disappeared to, Sugar Belle wiped away some of the slime covering her eyes, only to see Cheeriilee's mouth locked tip around Mac's tip, eagerly swallowing the rest of his load.

With a satisfied sigh, Macintosh pulled his softening tool from Cheerilee's mouth, the last of his cum drooling from the tip. Cheerilee turned to Sugar Belle, her cheeks bulging with cum. Without a word, Sugar Belle leaned forward, catching the other mare's lips in a kiss. Cheerilee opened her mouth just wide enough to allow some seed to spill out into the rightful owner's mouth.

The two mares continued their kiss, long after all of the jizz had been swallowed, before finally breaking apart. "I'm so proud of you!" Cheerilee beamed.

"M-me too," Sugar Belle panted. "I wasn't sure if I had what it took."

"Sure did help that ya had the best teacher in Ponyville to guide you," Big Mac said, kissing his wife on top of her head. "Would ya like t' join us for dinner?" he asked, turning to the mare in question.

"Of course, I would," Cheerilee replied. "Maybe afterwards, Sugar Belle could help me with my anal."

"It would be my pleasure," Sugar Belle said, as the three of them stood up, and began packing up the stall to go home.

Look out, Pinkie Pie; there's going to be a new Ponyville Cocksucking Champion, this year.


Author's Note

Sugar Belle placed second in this year's Cocksucking Championship, being beaten only by Sunburst.

Next Chapter