“Careful,” Thomas cautioned as the tips of his fingers glided over the bottom of Honey’s fuzzy breast, forcing her to stifle her giggles.

The green mare sucked in a breath to settle her nerves. She wore her full maid uniform, but the front had been lowered to allow her breasts to spill out. In her left hand she rotated an apple taken from the kitchens. The idea was to hold onto it for as long as possible without crushing the poor, innocent, scrumptious fruit; all while playing a friendly game of checkers with Moonlight. The task proved especially daunting when, every so often, her teacher would tease her nipple with a surprise pinch.

Several taps came from the board as Moonlight advanced her red piece to the other end. “King me.”

Honey sighed and flipped the piece over for Moonlight. “Yer good,” she said without resentment and advanced her own black king piece, taking one of Moonlight’s.

“And you’re getting better,” Moonlight replied, taking her turn and prepping her next assault. “Each game you last longer and longer. You’re building quite the tolerance.”

“Nnngh!” Honey sealed her lips, muffling her moan as Thomas gave her nipple an especially hard pinch. “It ain’t easy, but we Apples know how to endure.”

“I’m being paid to do this,” Thomas deadpanned as the mares regarded him. “This isn’t in the job description, but I’m on the clock, so that means I’m being paid to be a distraction by pinching a mare’s nipples while my girlfriend watches.”

Moonlight shared a look of confusion with her opponent. “And? It sounded like you had something more to say.”

“That’s just it,” Thomas said with an uncertain laugh. “I really feel like I should, but I think I’m learning to endure, too.”

Moonlight leaned over to the side and grinned at Thomas. “At least your body’s not becoming numb,” she tittered.

Thomas followed his unicorn’s gaze and reflexively shot his hand to cover his loincloth sealed crotch, earning further giggles from both mares. He glowered at them both for laughing at his expense. “Oh haha. Very funny.”

Moonlight grinned appreciatively at Thomas’ sarcasm. It was the tone he used when he was playing along and wasn’t hurt. Since moving in together, the unicorn had gotten much better at reading her stallion’s emotions. She could usually pick up on when he was being down on himself, but thankfully his really low moods had become few and far between.

“Well Ah certainly think it’s funny,” Honey stated as she made her move. “Ah can kinda get the whole nudity ‘n’ sex thing ‘n’ not wantin’ ta share that with strangers, but she’s yer herd mate for Faust’s sake. It ain’t like ya got anything she hasn’t already seen before.”

Frowning, Thomas gave Honey’s nipple an especially long and hard pinch. “I grew up all my life like this, and conditioned responses take a little bit to grow out of,” he argued.

“Besides, I like that he wears clothes most of the time.” Moonlight made her move. “I think it adds a dash of mystery, like there’s something worth hiding. On top of that, being one of the few who gets to see it makes me feel rather privileged. Your move.”

Honey hummed in frustration as she surveyed the board. Moonlight had backed her into a corner and left her with few pieces to work with. It looked like the end was, once again, nigh.

“What about that piece there,” Thomas pointed to the far right corner where a lone black king stood, waiting to be taken out by Moonlight’s superior numbers before the final charge.

“What about it?” Honey did not hide her disappointment, defeat evident in her tone. “There’s nowhere I can move. The edge of the board is to the top and right, so I can’t advance, and there’s a solid line in back so I can’t retreat. That little guy’s just sittin there waiting ta be taken.”

“What about to the left?”

“Hey. No cheating!” Moonlight countered.

“Sorry, Moon, but I am technically on her side at the moment. That alright?” he asked, cupping the bottom of Honey’s breast as he studied his mare’s expression. Moonlight’s bemusement lingered only a second longer before she made a relenting huff.

“Fine,” Moonlight conceded. It made sense to let Honey know that Thomas was on her side, that she could trust him, not to mention she was probably in need of a good morale boost by now. “If you think it’ll help, I’ll let you be a team.”

Honey’s elated smile grew as she looked again at Thomas’ recommended direction. Moonlight’s pieces had been aligned just so, such that she was internally kicking herself for not seeing it earlier. Eagerly, she took hold of the piece she’d written off as a goner and sent it advancing to the left, taking out five of Moonlight’s pieces. “Hot dawg!” she exclaimed, only for her fingers to grip around the red fruit and send juice flying out in all directions. “… oops.”

Thomas smiled flatly as he pulled back. Being so close, he had taken the brunt of the mess as clumps of apple and juice ran down his face and chest. He wasn’t wearing a shirt, so at least he didn’t have to worry about getting his clothes sticky.

“Ah am so sorry!” Honey stood from her chair, her bare, sticky breasts bouncing from the sudden movement. “Ah… uh…” After a brief moment of panic, the mare rushed off to the bathroom and retrieved a towel. After quickly wiping herself down, she proceeded to dab all across Thomas’ frame as she continued to murmur a steady stream of apologies.

“Relax, Honey,” Moonlight reassured as she stifled her laughter. “A little apple juice isn’t going to make him melt.” She leaned forward and propped her chin up on her hand and elbow as she watched. Despite her words, Honey was still frantic as she dabbed across Thomas’ body. He resisted, for all that was worth against the earth mare’s might. Moonlight gave another chuckle when she spied the reluctant acceptance on Thomas’ face. It was cute.

Finally the task was done, and Honey stepped back to examine her handiwork. “Sorry again. Ah’ll do better next time. Promise.”

Thomas ran his hands over where the juice had been, relieved that his body wasn’t sticky. When a faint whiff touched his nostrils, he held his arm against his face and inhaled deeply. “And now I smell like apples.”

“See? It ain’t all bad,” Honey pointed out uncertainly. She still looked nervous, and that was upsetting her teacher.

“Moonlight.”

“Yes, Thomas.”

“What’s that thing you do when I start to get down on myself?”

“Varies,” she answered nonchalantly, knowing where this was going. “My personal favorites are the hug and firm slap to the plot.”

“Right.” Thomas nodded. He gave Honey a look and earned a grimace of anticipation. She knew where this was going, too. The crack of flesh on flesh set the mare’s cheeks rippling as she yelped. Before she could respond, Thomas grabbed her by the elbows and sat her back down in the chair from earlier. Her herding impulses had kicked in, compelling her to go along with the one in highest authority. Now on eye level, he lunged for the mare and wrapped his arms around her neck.

“T-Thomas?” Honey asked timidly.

“Honey,” Thomas replied into her furred neck. “If I find out you were just pretending to be upset to trick me into a hug…” He paused to let her imagination run. “… I’ll be very upset that you didn’t just ask for one directly.”

Smiling, Honey reached around the human and pulled him close, her bare breasts squishing against his chest. “Where’s the fun in that?” she asked. “Hugs are better when they’re earned.”

Moonlight also smiled. “With all due respect, I’m afraid I must disagree. Hugs should be given freely, not earned.”

“Maybe, but Ah still think it’s more fun this way,” Honey said as she nuzzled into Thomas’ shoulder.

Eventually Thomas retrieved a spare apple and they resumed the game. Despite her comeback, Honey still lost, but managed to keep the apple intact.

**********

Meanwhile, in the sex dungeon, Silver had tied Surprise down to a table with her head down, arms out, and ass high in the air. Tonight’s weapon of choice was a long wooden stick with a feather attached at one end and a paddle at the other. Its name was Spanky. She spun the stick in her hands as she walked around the table, smiling menacingly as her subject’s eyes followed her teacher’s every move.

“I honestly don’t know why I bother,” Silver commented disinterestedly as she fiddled with Spanky. She wore thigh high boots and a red and black corset that allowed her nipples and vulva to poke free. Her gloves were a shiny black leather and her mane had been tied back in a bun. “Night after night we train, but I don’t think you’ve lost even an ounce of fat.” She idly stroked Spanky’s feather across Surprise’s cutie mark, earning a muffled whimper from the gagged mare.

“Nnnngh!”

Silver grabbed a handful of Surprise’s red marked rump, the student’s butt flesh spilling over as the teacher sank her fingers in deep. “Honestly, what am I going to do with you?” She blew softly against the large white cheeks, earning a muffled squeal from their owner.

“Nnngh!” This moan sounded more pleading than the last, almost apologetic.

Feeling playful, Silver held up the feathered end of Spanky and began gently tickling an inch away from the white mare’s clit. As Surprise squirmed, Silver nuzzled the mare’s plump cheek affectionately, continuing to blow on her puckered anus.

The bat mare grinned sadistically as the pegasus writhed under her expert touch. “How does it feel?” Surprise’s moan sounded more urgent now, a testament to Silver’s work. As dom, she’d made great progress in learning to make the sub beg for it, to demand that the dom take control and guide the sub to bliss.

Surprise began grunting urgently, surprising Silver by gesturing with her head to the far wall. The bat followed her line of sight and beheld the clock.

“Is it that time already?” Silver smiled in disappointment as she suddenly thrust two fingers into Surprise’s snatch, pistoning in and out of her with a sloppy haste. “Sorry, sweetie,” she purred. “I lost track of time, so I’m afraid I can’t tease you like I’d planned to. I guess we both still need a bit more training,” she tittered. “Still, it’d be terribly cruel of me to end our session without finishing you off first,” she consoled. Surprise screamed into her gag, her buns jiggling with anxious need, until finally she sprayed her juices all over Silver’s hand. At last Silver began undoing Surprise’s bonds. “My, how time does fly.”

“It sure does,” Surprise chirped happily when her gag had been removed, neither panting nor showing any other sign that she’d recently climaxed. “But I’m sorry I’m not losing the weight. I really am trying, honest. I’ve gone on diets before, but my body’s just always managed to retain its squishability.” Her words sounded surprisingly sincere, like she really was remorseful for disappointing her trainer.

“It’s quite alright,” Silver reassured as she tenderly, appreciatively ran her fingers over the mare’s rump. “To be honest, the thing is growing on me.” To Silver’s surprise she felt a tiny tremor reverberate from the pegasi’s bottom, which she suspected might have been some expression of gratitude. Not wanting to dwell on the matter, the bat quickly undid the remaining bonds and helped her clean up. From there she pulled the maid uniform from the rack and hurried Surprise out, just in time to be face to face with Honey. The two mares greeted warmly with soft kisses to the cheek, as had become their custom, before walking past one another.

The group had established a routine of alternation. Thomas and Silver would teach Honey and Surprise in the mornings, respectively, and then switch in the afternoons. Moonlight stuck by Thomas, but would occasionally go with Silver if the bat agreed to lessons that could be carried out simultaneously in the same room. The unicorn was still a guard, after all, and refused to shirk from her duties to her stallion.

Honey surveyed the room, particularly the table where the lingering stain of Surprise’s juices still stood out, before she spied Silver and whistled. “Somepony looks mighty frightenin’ tonight.”

“Really?” Silver grinned and spun around for Honey’s viewing pleasure. “You don’t think it’s too much?” She’d committed herself to perfecting the act and every detail within it. Honey’s critique was as welcomed as any other.

“Shoot, filly.” Honey approached and tenderly ran her hands down the smaller mare’s bodice. “Ah might have ta start thinkin’ o’ getting one of these mahself.”

“That’s very thoughtful of you to say.” Silver smirked at seeing the way Honey’s hard nipples made themselves seen through the fabric, imagining what Thomas and Moonlight had done to earn such a reaction. “However, I hope you’re not expecting to butter up your teacher out of the night’s lesson.”

Honey stared flatly down at the bat. “Ya do realize there’s more than one way ta take that, right?”

“As soon as the words left my lips, yes,” Silver acknowledged with a firm nod and pleased smile. “Feel free to strip. We can begin as soon as you are ready.”

Honey nodded and quickly stripped out of her uniform, setting it on a clothes hanger so it wouldn’t get wrinkled. From there she followed Silver’s directions to tie herself onto the same table as Surprise. This left Silver to tie the last binds, leaving Honey belly up, arms out, and knees pulled tightly against her torso in such a way as to present her ass for ready use.

“This just feels so weird,” Honey giggled nervously as she tested her binds.

“Being on your back?” Silver asked idly as she retrieved Spanky. “You never tried different positions with Jona or any other mare?”

“E’nope,” Honey replied anxiously as she eyed the stick tapping away in her mistress’ hands.

“Hmm. Has Thomas not introduced you to his and Moonlight’s book? Surely you must have been expecting this by now?”

Honey averted her gaze. “They… read a little ta me.” She gulped audibly and shuddered. “It was… interesting.”

Silver cleared her throat.

“Mi’lady!” Honey corrected, remembering the rules.

Silver nodded her approval as she began to slowly circle around the bound mare. “Tell me, then. How are you enjoying your stay at the castle, so far.”

Honey was breathing heavily as her eyes followed the smaller mare around her. “V-very much so, mi’lady. Everypony’s been awful friendly.” A crack from Spanky in its owners hands jostled Honey’s thoughts. “Th-the food’s the best Ah had in ages, ‘n’ Ah’m not butterin’ ya up when Ah say the work ain’t bad either, Mi’lady.”

Silver licked her lips as she eyed the green mare’s body and ran a hand sensually down her thigh. “Lovely,” she purred. “And Thomas? How are his lessons fairing?”

“He’s been real sweet ta me, Mi’lady,” Honey groaned as she felt Silver’s fingers nearing her sex. “Him ‘n’ Moonlight both have been pretty patient with mah lessons. Ah almost never break the apple, anymooooore!” Honey cried out as she felt Silver’s hand begin brushing her sex.

“Hmm. Lovely,” Silver cooed as she played with her new toy.

**********

Surprise entered Luna’s chambers with a strut, pretending not to notice her audience as her hips swayed in the way she knew held universal appeal to both mares and stallions. Spotting a bit of lint in the carpet, she turned her back to her audience and bent over to pick it up. It took all her willpower to keep her tail modestly in place. After all, she might have been a bit on the lewd side, compared to most ponies, for applying for the highest position in the field of prostitution, but there was still an etiquette to be observed.

“Oh my god!” Thomas said in horror as he came up behind Surprise. He reached out, but dared not set his hands upon the mare’s rump, his eyes darting from red mark to red mark. “D-does it hurt?”

Surprise was momentarily perplexed by this question until it dawned on her how her plot must look. She straightened and faced Thomas with her usual perky smile. “No worries, little buddy. Silver and I were just playing.”

“Yeah but…” he gestured impotently at her now concealed backside. “That looks like it really hurt.”

“Yeah, but I’m a member of the Cloudsdale city guard!” Surprise set her hands on her hips and struck a pose befitting a statue. “We learn to fight through the pain, to do whatever it takes to complete the mission. And if it makes Silver happy to play a little rough with my butt, then that’s exactly what she’s gonna do!”

Thomas face-palmed. “You do know you’re allowed to refuse an order if you want, right?”

“Sure do,” Surprise answered with a chipper grin. “It’s real nice that you’re worried for me, but don’t get your undies in a twist. I know my limits,” she reassured. “If I’m not comfortable, I’ll say stop.”

“I know,” Thomas sighed in defeat. “You’re an adult and I should trust your judgement.”

“My stallion’s a real softy,” Moonlight commented affectionately.

Surprise’s face scrunched in puzzlement. “You think so?” She reached out and began pinching along Thomas’ arm. He pulled back on impulse, but decided to let her do as she wanted. “Hmm. There’s a bit of give, but he’s actually toning up pretty nicely.”

Thomas beamed at the compliment. “Thanks for noticing.”

“Now if you want softies,” Surprise yanked her top down, allowing her breasts to pop free. “Try these on for size.”

Thomas blinked in momentary surprise at the brazen display, but just smiled and shook his head in dismissal. He patted Surprise’s shoulder and resolved to learn not to let his guard down around this mare. “Just so I know what I’m working with, what’d you and Silver do tonight?”

“Well, first she tied me up. She doesn’t do that often, but I can tell she really likes it. Then she spanked me for a little bit before she started touching me with Spanky. I told you about Spanky, right?”

Thomas nodded as he fixed the mare with a neutral expression. It still seemed so weird how anyone could stay on full happy mode for so long. Logic demanded that even emotions needed to take breaks.

Surprise went into gratuitous detail of everything Silver did to her. Thomas tried to stop her, but she’d gotten into the spirit of storytelling and was talking a mile a minute. When she finished, she didn’t bother recovering her breath, but Thomas certainly felt exhausted.

“Moonlight,” Thomas gasped breathlessly. “What was tonight’s lesson?”

Moonlight also looked winded, but much less so than Thomas. “As a reward for last time, I think we agreed to let Surprise pick what she wanted to do.”

“Yay me!” Surprise pressed her wrists together and applauded rapidly, bouncing giddily as her pudge bobbed within her clothes. She came to a quick halt and donned a thoughtful expression, making her teachers grow anxious as they waited to hear her decision.

“Got it!” Surprise exclaimed, startling the others as she disappeared and reappeared across the room in front of Moonlight and set her hands on the mare’s shoulders. “I know what I want!” she declared as she bore down on the nervous unicorn with a manic grin.

(Some time later)

“Left hand blue,” Thomas informed.

“Hold on,” Surprise strained to say as she contorted her body to reach the desired spot. Her fingers grazed across Thomas’ inner thighs, causing him to shudder and her to giggle, until finally she found her destination. “Got it!”

They were all naked, as per Surprise’s instruction. She said it would be more fun this way. To Thomas’ relief, and a bit of secret disappointment, the white mare spent very little time staring at his alien anatomy before their game began. Aside from occasional brushes, many of which Thomas felt were a little too suspicious to be accidental, there was nothing overtly sexual about their game. It was all good, (relatively) clean fun between three friends.

The game ended with, to the shock of no one, Surprise as the victor. There was just no stopping her determination and, at times, unnatural flexibility. Afterwards, the three retired to the bed to rest.

“That was pretty good,” Surprise purred contentedly as she leaned against the pillows and caressed the human lying over her belly. “Hmm. You’re so warm.”

Thomas shuddered as he felt her fingers tease along his sides, deliberately avoiding any of his ticklish spots. He looked over to the unicorn beside them and smiled. “This is alright, right?”

Moonlight chuckled happily as she watched the pegasus stroke her stallion. “I’m happy you’re so concerned about me, but it’s really alright,” she assured. “You’re my stud of a stallion. It makes me happy to watch you make other mares happy.”

Watching his beloved, Thomas groaned as he felt Surprise’s tender fingers glide up his inner thigh and tantalizingly close to his groin.

Moonlight giggled at his reaction. “I also love watching you make those cute faces.”

“Well then,” Thomas sighed, “I guess there’s only one thing to do.” Without further warning, the spry little human lunged for the orange mare and jabbed his fingers beneath her armpits.

“Aaaah-haha!” Moonlight cried out as her body reflexively balled up to protect itself. “No fair!” She pushed Thomas away as best she could, only to give out another cry when Surprise joined in the assault.

Not too much to say about this chapter. It’s just a nice, calm look at what our characters are going to be doing with most of their time for the next few days. Surprise’s happy-go-lucky attitude is helping her take to things rather quickly, but Honey still has a few reservations. Thankfully the mares’ peers are a kind, patient, friendly lot, here to do what they can to help.

However, given the heavy emphasis on interpersonal connections over rigorous routines in this job, expect things to change up quite quickly.