Chestnut and Apples

Chapters

The Secret
A Night at the Castle
A Deal with the Princess
Elegance and Speed
Bold and Shy
Bouncy

The Secret

Author's Note

This story can probably stand on its own, but reading the prequel is probably best. Enjoy!

The Secret

Applejack rushed around as she grabbed the last few things she’d need before heading off to dinner at Twilight’s. She slipped into the bathroom and raised her tail. A quick glance showed that there was no traces left of her earlier fun that her friends would notice easily, although she was still a little wet. She patted herself down and decided it would be enough. She’d be late if she tried to do any deeper cleaning anyway, and the bat pony’s long tongue seemed like it had gone deep enough to clean out any mess. She put thoughts of the afternoon of fun away as she tightened her coat and went out into the snow.

A thick group of dark clouds had covered the sunset, so it was already looking pretty dark. A chill wind hinted that a winter storm might be blowing in later. If it was bad enough, she’d just have to spend the night at Twilight’s, but she wouldn’t mind another sleepover there. It’d be like old times, back when Twilight lived in the library.

Applejack’s reminiscing made the trek into town go by in a blur, and she found herself at the castle all too soon. She tucked her tail in tight and gave a loud knock. Spike pushed open the door.

“Come on in, Applejack. You’re the second one to arrive. Well, actually the third, but Pinkie forgot something or maybe she just couldn’t carry all her games here in one trip. She’ll be back. Brr! Let’s get in by the fire.”

Spike shivered and scampered ahead after the door was shut. Applejack shook off any snow stuck to her hooves before stepping inside. On the far side of the main hall, Twilight, Starlight, and Rarity were chatting. They paused and waved to Applejack. She hung up her coat on the little stand by the door and walked over.

“Nice job on the fire,” Applejack said. “I can’t imagine what it takes to keep this big ole castle warm.”

“Twilight likes to experiment with insulation spells,” Starlight said. “Not a bad choice, although I think the first one you tried was perfectly fine.”

“But it’s not! It’s a matter of fine tuning for heat loss and ventilation, and…” Twilight went on, but Applejack didn’t really pay any more attention.

Rarity gave her a look she couldn’t quite read and motioned for her to sit next to her. It was quite warm by the fire, and there didn’t seem to be any places where the cold wind was getting into the castle, so Twilight’s spell must have been doing its job.

“Oh, Twilight, let’s talk about something more interesting than those little differences in spells,” Rarity said. “How are things out at the farm lately? Surely there isn’t much work to do with all the snow. What have you been up to with all that time?”

“Mostly relaxing and keeping Big Mac and Apple Bloom out of trouble. Nothing too unusual.” Applejack chuckled nervously.

Rarity raised an eyebrow. “Are you sure that’s all?” She seemed like she was about to ask or say something more, but a knock on the door interrupted her.

Spike jumped up and ran over to open it. A chill breeze blasted inside for just a moment as Pinkie and Fluttershy stepped into the room. Spike was about to shut the door, but a colorful blur zipped through.

“Totally not late!” Rainbow Dash shouted as her wet hooves skidded across the floor. She stopped before crashing into anyone or anything. She stretched out her wings and smiled.

“That was quite an entrance,” Rarity said.

Twilight pulled out a list. “Yes, but let’s not get behind. Everything should be ready for dinner now. Oh, I need to get the oat rolls out of the oven right away!”

Twilight vanished in a flash of magic, and Spike led them to the dining room. Rarity sat next to Applejack. She leaned in and whispered. “You’ve always been bad at hiding the truth. But I promise I’ll let you share your little adventure when you’re ready. Besides, we have to protect the innocence of Spike.”

Applejack blushed. “I doubt having Starlight around has helped preserve that.”

Starlight looked over with her ears held high. “Did I hear my name?”

Rarity unfolded her napkin and smiled. “Well, we did mention you. But it’s the sort of conversation that’s best had once any little dragons are in bed.”

Starlight looked over at Spike, who was currently busy helping Twilight bring in trays of the food. “You always were a sucker for any drama or juicy stories about me and Trixie. I’m sure I’ll have plenty to tell once it’s late enough, and maybe after I have a little to drink.”

Twilight finished setting all the dishes on the table. “Well, girls, I didn’t cross reference recipes from a dozen cookbooks for nothing. Let’s eat!”

Applejack could forget about Rarity for the moment with such amazing food in front of her. A basket of oat rolls was passed around, and some honey and butter was waiting on the table in nice little dishes. Twilight seemed to be trying hard to be fancier now that she was a princess, but it felt nice to eat elegantly for a change. She could appreciate all the effort it took to make things look this nice, even if she was fine with simpler things.

After the rolls went around, Twilight served them all a nice carrot and squash soup with a garnish of thin apple slices and parsley. As they ate, they made small talk about the weather and how nice it was to take things easy since the cold weather made it hard to do much. Soon, the main course was served. Twilight had made a nice pasta with a creamy alfredo sauce with a side of asparagus. Dessert was a peach cobbler. It was good, but Applejack thought it would never be as good as apple cobbler.

The night went by quickly. They left the dishes for the morning and went off to play some games. They played a complicated one based on Daring Do’s adventures that was a favorite of Rainbow Dash and Spike. Starlight pulled off some clever tricks and managed to win. After that, they tried a few more until Spike went to bed. That was when Starlight brought out the wine and cards.

Starlight poured them each a glass. “Well, girls. You know the rules. If you win a hand, you get to ask somepony else to tell a secret.”

Those hadn’t always been the rules, but they had learned the hard way that debts, gambling, and friendship don’t always mix, so they had switched from actually betting anything to the current rules.

Starlight dealt the cards while Applejack took the first sip of the wine. Starlight always favored the stronger, older vintages. That usually meant they’d all be a little tipsy once they started spilling their secrets. Applejack looked at her hand. It wasn’t bad, but it wasn’t great either. She’d just have to play it straight and hope it was enough, and she was terrible at bluffing anyway. She swapped out a few of her cards and things were looking a little better.

Fluttershy laid down her cards. “Um… I fold.”

Rainbow Dash had a worried look. She never folded because she didn’t want to be a “quitter,” but that usually bit her in the flank unless she got a great hand. Nopony else folded, so they all laid down their cards.

Applejack had two pairs. Rainbow Dash only had one. Fluttershy didn’t really have anything, and neither did Twilight or Starlight. Rarity looked over the cards and grinned.

“Full house, darlings. Now, who here has a juicy secret that I should ask about?”

She looked over at Applejack. It should have been impossible for Rarity to know about what happened earlier that day, but Applejack could somehow feel she was going to ask about it.

“Applejack, let’s hear about your little secret from today. I heard you had a special visitor.”

Rarity laughed and sipped her wine but didn’t break eye contact. Applejack rubbed her front legs together as she tried to think of what to say. The rules were the rules, and she wouldn’t lie.

“Fine. I’ll tell ya about that, but how in the hay did you know about it?”

“We all-” Pinkie began to talk, but Rarity used her magic to shut Pinkie’s mouth.

“Pinkie, we can’t give away secrets for free. If she wants to get that out of me, she’ll have to win a round.”

“Wait, Pinkie knows too? Do you all know something I don’t?” Applejack looked around. From the looks on their faces, all or most of them were in on whatever this was. She’d get to the bottom of this, but first she had to do as Rarity had asked. She told very brief version of what had happened earlier with the bat pony stallion. She had to include some of the more embarrassing details of what happened between her and Chester when Rarity asked for them. By the time she was done telling about it, everyone looked a bit flustered except Rainbow Dash, who just looked eager.

“There, ya happy?”

“That will do,” Rarity said.

Applejack had thought they’d be more surprised. She hadn’t been with any stallion before. She had just done a little experimenting with Rainbow Dash from time to time or Rarity once or twice. At these little late night parties, she had learned all the details of her friends intimate encounters. She had always secretly wanted to have her own to share. It was starting to feel good now that she actually had one. But what she most wanted was to figure out how they all knew.

Applejack pounded a hoof on the table. “Deal the next hand.”

She was feeling lucky, or maybe she was just feeling that it would only be fair if luck let her win. She took her cards and looked them over. Two princesses. That was a great start. She traded in her other three cards and got one more princess card. Nobody folded this time. She prayed that nopony had a full house. Her friends revealed their hands, and Applejack had the winning one. Her three princesses beat their pairs or two pairs.

“Okay, this one’s for you, Rarity. How’d you know about Chester?”

“Oh, that’s hardly a secret. We paid him to visit you. The only thing we weren’t sure about is how it would go, but he told us all about it. In fact, he got here long before you did. Chestnut, you can come out now.”

Chester seemed to appear from nowhere as he stepped out of the shadows. His light brown coat and black mane were unmistakable. Applejack was sure this was him. He winked at her. She blushed even as she eyed his lean body with a sudden longing.

“Good evening ladies. Mind if I join in the fun?”

He poured a glass of wine and took a smooth but long sip as he sat on the couch. He stretched out in a very sensual way that had to be deliberate. He sat with his legs spread just enough to offer peek at what was between them. Applejack tried not to stare.

“You’ve fulfilled the contract, Mr. Chestnut,” Twilight said. “But we don’t mind if you want to stick around for tonight, especially Applejack. I’ve never seen her stare like that.”

Chester got up and sat next to Applejack. She hesitated a moment before giving in and snuggling against his warmth. He put a wing around her back.

“She is a very special pony. After getting to know her, I’d please her any day for free.”

Applejack breathed a sigh of relief. She had been worrying that he had only done what he did for the money. She looked at all her friends.

“So, you paid him to visit me? Or was the sex a part of that contract?”

Rainbow Dash blushed then spoke. “We left that up to him. We just paid him to provide you a little company in winter. We all knew how pent up you were last year, so we guessed something might happen.”

“I need to stick around anyway,” Chester said. “Things happened so fast, and we didn’t exactly use any protection.”

Applejack’s ears folded down. She hadn’t thought of that. She frowned a little. She had always wanted foals of her own, but it had always been something to think about in the future.

“There are some spells we can use to check,” Twilight said.

“Oh, let’s do it!” Pinkie shouted. “I can’t wait to plan the wedding, and baby shower, and-”

Twilight put a wing over Pinkie’s face. “Keep it down. We don’t want to wake Spike.” She turned back to Applejack. “Is this something you want to find out?”

“Yes. The sooner I know, the better. I’m sure granny won’t be happy with how it all happened, but I’ll need to fix things up at home if I’m… expecting.”

“Lay down then. This will only take a moment.”

Applejack stretched out along the couch. She laid her head in Chester’s lap. The smell of the stallion was oddly comforting. Twilight’s horn glowed, and she slowly lowered it until the tip touched Applejack’s belly. A tingle of magic transferred from the horn to her. It rushed through her then went back to where the horn had touched her. A little glowing symbol appeared.

“What’s that mean?” Applejack asked. She held her breath and waited for Twilight’s answer.

“If all goes well, you can expect a colt in about a year. Congratulations!”

Twilight gave Applejack a big hug. All her friends and Chester joined in. Applejack felt tears coming. She wiped them away and kept smiling. No matter what changes this would bring, she had her friends and Chester to help. But she’d really have to spend more time with the cute bat pony to really get to know him.

“This is great! Should I be planning a wedding first? Or the ‘Congratulations! It’s a foal’ party?” Pinkie asked.

“Probably the second one. Chester and me will have to figure a few things out first.”

“I guess I’ll need to find a new line of work. I don’t think you’ll want me providing mares with company as my job anymore, well except you. You’ll have me all the time.”

Applejack snuggled against the fluffy bat pony. “I can think of plenty of fun ways to use those skills of yours, though.”

He gave her a kiss. She rubbed his belly until her hoof bumped into the tip of his cock. He was already a little aroused. When they stopped, all of Applejack’s friends were still watching and smiling.

“I think the storm’s gotten worse, so you all better stay the night,” Twilight said. “You two can have the biggest guest room. And Chestnut, promise me that you’ll let her get at least a little sleep. Luna mentioned how bat ponies can go all night.”

Chester nuzzled Applejack and helped her up. “Luna would know that better than anypony.” He chuckled as he led Applejack away to the bedroom.

A Night at the Castle

Chester stretched out on the bed. After learning just what sort of work he did, Applejack had to admit that he did look perfect. He was all lean muscle and fluffy enough to look soft and cute while still looking strong. He stretched his wings and legs out, giving Applejack plenty of eye candy as he teased her. He rolled to the side just enough to have his partially aroused cock press into the bed enough to show it off while leaving Applejack wanting more.

Applejack was surprised to feel her clit winking already. She shook her head. She really did want Chester, but she also wanted to be sure of some things first.

“Chester, you’re looking mighty fine, but I have a few questions for you.”

Applejack slid into the bed next to him. He gave her a quick kiss and placed a wing in a spot on the back of her neck that made her entire spine tingle.

“I’m not surprised. I didn’t expect things to turn out this way when your friends paid me.”

Applejack nuzzled against his chest, and he wrapped his wings around her. She raised her head and looked into his eyes that sparkled in the dim light.

“Have you worked long as the sort of stallion that provides certain company for mares?”

“Not really. A bit less than a year. I worked as one of Luna’s guards first, but I wasn’t the best at keeping naughty thoughts out of my mind when I was bored at my post. Luna noticed and suggested I try something else, although she was surprised when I chose to do this.”

“So, out of all the mares, why did you decide to stay with me? It’s not just because of the foal, is it?”

“That would be enough. As a guard, I learned that honor and duty are important. You are the first where I forgot to take the proper safeguards, but when I saw just how strong you were back when we first met in the barn, I knew you’d be more special than any other mare.”

He rubbed a hoof along her back and gave her ear a teasing nibble. She pressed up against him and sighed. She breathed in his scent and pulled him down for a long kiss.

“Chester… I guess we’ll figure things out. You do seem honest, and that’s always the best place to start. Now let’s do what my friends actually think we’re doing.”

Applejack gasped as his wing slid down to rub her flanks. She could feel the warmth of his shaft against her belly. She smiled and nuzzled noses with him. She rolled him over and pressed him into the bed as she continued to grind against him.

“That’s the what I like to see. Now why don’t you show me more of what I saw back in the barn? I won’t go easy on you this time. I’m not tied up after all.”

He distracted her with a kiss and rolled on top. He lowered himself enough to slide his shaft against her wet folds. Applejack grinned and tried to flip him back over, but he snuck in his wings and tickled her belly. She laughed and couldn’t find the strength to roll him back over. Her laughs turned to a needy moan as he thrust inside her with one smooth thrust.

“Looks like you win this round. Can I make one request? Take me like the rough stallion I know you are.”

Applejack slid off his tip and rolled onto her belly with her rear held high. Chester kissed the back of her neck and licked her ear slowly as he put one hoof around her barrel then the other. He cuddled against her for one moment as he lined their hips up before thrusting hard against her. She felt every inch of him slide in and moaned loud enough that her friends might have heard.

He thrust again and she bit the pillow as her first climax hit. She could feel her clit winking as her fluids dripped down onto the bed below her. Chester seemed to notice how tight she was around him and focused on rolling his hips slowly against hers. His medial ring pressed against her sensitive clit and she could feel the base of his cock stretching her to her limits. As her body stopped trembling, he gripped her tighter.

“Ready for even more fun?”

He bit onto her mane and started thrusting hard and fast. Her hips and his met as he drove deep with each motion. The bed shook back and forth as he kept going until finally his hooves slid down lower, brushing against her teats as he brought himself flush against her. He grunted and he came hard. He pressed against her as his fluids filled her until they were dripping down her legs.

The two of them slumped down onto the bed. They were short on breath, but he rolled to the side just enough to pull her face to his in a quick kiss.

“Chester, I don’t think I’ve said it properly, but I love you.”

“I love you, too, Applejack.”

He nuzzled a ticklish spot on her neck and she laughed softly. She moaned as her little movement let her feel just how deep he still was inside her. He slowly pulled back, and she felt wet mess fall onto the bed underneath her. She rolled to her side and gave him a tight hug. After a few more kisses, they both smiled.

“So, do you think your friends heard any of that?”

“I’m sure some of them couldn’t resist listening in.”

“We could always go show off if they’re still awake.”

“Now that’s something that would surprise them, but I’m just happy having you to myself.”

He laughed and wrapped a wing around her back. She wasn’t quite as tired as after a good day of hard work, but all this fun had worn her out. She couldn’t resist snuggling against his fluffy chest, and she fell asleep as he slowly stroked her back.

Starlight blushed as she looked at her wet hoof. Rainbow Dash had suggested a little spell to spy on the happy couple, but she hadn’t expected something so wild from the down-to-earth Applejack. Rainbow Dash quickly rubbed herself until she cried out and made a little mess on the couch.

Rarity was also there, but she had been a little less obvious about pleasuring herself. She slowly got up.

“That was quite the show. Now I think I should go take care of a few things in private.”

Starlight smirked as she saw just how wet Rarity was under her tail. Twilight and Fluttershy had both become too flustered at different points in watching and had excused themselves already. Pinkie Pie had been more open, just like Rainbow Dash, but she hadn’t really held back. She was sitting in post-climax bliss as she stretched out across the other couch.

Starlight thought about following Rarity, but Twilight returned to the room before she could gather the energy to get up. Twilight blushed as she looked over Starlight. They hadn’t quite gone to the intimate level of friendship lessons yet, even if Starlight wouldn’t have minded.

“Um… so… it’s over, right?” Twilight said. “What do you think? Wasn’t it a good idea to find a nice stallion for Applejack?”

Starlight shrugged. “I guess. They seem a good match, but it does feel a little forced. Still, I guess Applejack is going to do this the traditional way. She does know that you could just do another spell to stop the pregnancy, right?”

“She’d get upset if I even mentioned it, but she knows.”

“I guess she would be the type of pony to think a little late magical intervention to be wrong.”

Twilight nodded. “She’s very traditional. So is her family.”

“That’s not going to make it easy to introduce Chester to them.”

“If she needs help with that, we can step in.” Twilight glanced around. “Ugh, Rainbow! Pinkie Pie! Do you know how many cleaning spells I’ll need to cast to get that out?”

Rainbow Dash pushed her hooves together in a lewd gesture and winked at Twilight.

“We could always make it messier.”

“I… uh… well… maybe not on the couch…”

Pinkie Pie’s ears perked up. “Oh, is Twilight finally ready for some fun?”

Starlight smiled. It seemed like everypony was in the mood to do things beyond the ordinary tonight, so it was going to be a night they’d all remember.

A Deal with the Princess

Author's Note

Sorry for the long delay. I tried a slower slice of life continuation of this story, but I just couldn't find any ideas that really excited me. Instead, I decided to go for the quick and more lewd ending to wrap it up. I should be releasing chapters more regularly now that I have them all sorted out.

A Deal with the Princess

Applejack wore herself out early that night. Chester nuzzled against her. He was a little tired after their fun, but after sitting quietly, he was feeling energetic again. It was the night after all, and that’s when he was most awake. He gave Applejack one more kiss and decided he’d go clean up and look for something to eat. He always felt hungry after mounting a cute mare.

He turned on the shower and hummed softly. He moaned softly as the warm water flowed over his still sensitive cock. It was enough to make him stiffen again, but he paid that no mind as he finished up and dried off.

He slipped quietly through the dark bedroom and out into the hall. His shut the door without making a sound. In the distance, it sounded like some of AJ’s friends were still awake. It was the same direction as the kitchen, so he decided he might as well go see what was happening.

As he got closer, he heard quiet moans that sounded like a mare having fun. He pushed open the door just enough to peek inside the sitting room and could see a pink mane bobbing up and down above the back of the couch in a slow rhythm that matched the moans. He pushed the door open the rest of the way.

“Hello, mares. Am I interrupting anything?”

Chester looked around. The couches, pillows, and blankets were a mess, and so were all the lovely mares inside the room. His cock throbbed as their scents hit him. He blushed but kept looking with a grin.

Twilight stood up and tried to smooth her ruffled feathers and mane with a bit of magic. She looked him over. Her eyes lingered on what was hanging beneath him.

“Chester? I thought you’d still be doing stuff with AJ.”

Chester laughed. “She’s the type to go to bed early, especially after all we did.”

Pinkie Pie finished up whatever she had been doing on the couch. A blushing Rainbow Dash sat up a moment later. Twilight looked at them then back to Chester.

“If she’s not using you… maybe we could…”

The princess blushed in a way that made Chester want to grab her and mount her right there, but he held back as he thought over what he had told Applejack.

“I’ll probably be leaving my current work behind now that I’ll be getting married.”

“But you aren’t married just yet. And I have an idea. Applejack and her family could really use the money. And tonight you’d have the chance to really earn it. Plus a big bonus for secrecy and the change to our current contract.”

Chester grinned and took a step toward Twilight and let his wing brush against hers. He whispered into her ear.

“I’m listening.”

She whispered a number into his ear and his eyes went wide. Twilight took a step back.

“We… used some magic to watch you and AJ. That’s why we’re all so wound up tonight. Me and the girls could use a little something to help us with that. Could you handle us all, one after another? We’d make it more than worth it.”

Chester was dripping on the floor at the thought of it. He nibbled Twilight’s ear and she gasped.

“That’s a lot of mares to please, but I am one of the best. Would you be first?”

“I am a princess. I do have things I need to get to in the morning, but I have a little time now. I prefer a little privacy. Come with me.”

Twilight’s brushed a feather along his chin as she strode past and walked down the hall. Her tail was lifted high and gave Chester a perfect view of just how ready she was. A droplet glistened on her winking clit before dripping slowly to the floor. Her cute purple opening was moist and ready but still looked tight. By the time he thought to look up, they were already in Twilight’s bedroom.

“Just a few spells to start. Let’s see… how did the stallion stopper spell go? Ah, I remember.”

Twilight’s horn glowed and a purple glow surrounded Chester’s balls. The warm almost tickling feel of magic surrounded them before vanishing a few moments later.

“What was that?”

“A little safeguard against any of us getting foals for tonight. Much better than a condom, don’t you think? But… I shouldn’t let magic distract me from you. I’ve honestly… never found a cute stallion to try things with before even if I… studied how it would feel like with magic and some toys.”

Twilight blushed deeply. She looked adorable and vulnerable like this instead of like the commanding princess she was supposed to be. Chester nuzzled her and smiled. He kissed her and hugged her tight against him as he walked the two of them to the edge of Twilight’s bed. He fluttered his wings to slow their fall. He landed just as he planned. His shaft was pressed against Twilight’s slick folds.

“A real stallion is always so much better. I’m surprised you don’t have your pick of the stallions around here.”

Twilight rubbed against him and gasped. She pulled him down against her and slid his shaft against her vulva and clit.

“Ah, you naughty bat. If I did that, they’d start saying I’m the princess of friendship with benefits.”

He nibbled at the edge of her wing and she moaned loudly. He kissed her while slowly pressing her forward and teasing her opening with each inch of his cock.

“Sounds like you’d have a lot more fun with that title.”

She pulled him in for a kiss. Her horn glowed and he felt a ring of magic take hold of his tip and angle it down. Twilight gasped and broke the kiss as he slid into her. She trembled as his tip stretched her. He resisted the urge to thrust. It was too fun to tease her.

“Are you going to let me do all the work? I know you’re holding back.”

Her horn glowed again. Her magic prodded at his puckered hole. He moaned as it pushed deeper and rubbed against just the right spot.

“Oh… it’s getting hard to hold back with that.”

He nipped at her ear. She let out a cute little squeak right as he wrapped his hooves tightly around her and thrust in hard and fast. He was rewarded with a long, loud moan as she eagerly grinded against the middle of his cock and pushed it in even further. She was tight. She cried out as her climax hit. Her body squeezed him even tighter.

It felt good to take control from a princess. He thrust quickly, pushing in all the way while he bent a wing down to rub Twilight’s slick clit. She pulled him closer and bit down on his mane to muffle her moans as her body eagerly milked his shaft. Twilight was panting as he circled his wingtip over her nub. He was getting close himself. Her magic had gone wild and was vibrating inside him. It seemed to amplify his pleasure, so he thrust in one last time and let loose.

When the bliss finally cleared, Twilight was looking up at him. He could feel the fluids running down his shaft as they dripped from her folds. She reached up and stroked his cheek with a hoof before giving him a slow kiss. She pulled back and massaged his wings.

“Ahh… Applejack’s lucky to have you. I can see why Luna recommended you now. I learned a lot from you.”

“I’m always happy to teach a princess a thing or two.”

“Oh, you. But there’s a few needy mares out there waiting for you. I’ll cast some spells to make sure AJ or Spike won’t wake up to see any of this. Now go and please everypony as much as you pleased me.”

Elegance and Speed

Chester stepped out into the sitting room. His shaft was still wet and dripping from his fun with Twilight as it swayed at half-mast below his belly. It sounded like Twilight’s friends were eager for his attention, so he didn’t take any time to clean off. Rainbow Dash threw another log on the fire as he approached. She looked up at him with a smile.

“There’s our stud. Starlight gave us a little peek into how things went with Twilight. I have a few ideas that might make this a little faster for those of us who are less shy.”

A large cushion had been placed in the middle of the room. Rarity sat on top of it and fluttered her eyes and gave him the look. She knew how to use the little expressions that said a lot. She motioned to him as she swayed her silky smooth tail just enough to give him the slightest hints at what was beneath.

“While Rainbow gets ready, why don’t you start with me? Be a darling and show me what a proper courtesan can do. I’m sure you learned how to make this graceful.”

Chester smiled. She reminded him of many of the richer clients back in Canterlot, but she had a certain authenticity that they lacked. He straightened his stance, giving her a good look at his cock beneath him as he stood close to her.

“Such a refined mare deserves the best. How may I serve you tonight?”

She laughed softly as he bowed.

“Why don’t show a lady the proper attention? I could use a little massage to loosen things up.”

Rarity stretched out her body. She was so smooth and glossy. Her tail lifted, showing her tight, wet opening. Her clit winked, and Chester’s pre dripped onto the floor. He leaned down and rubbed her back slowly. She moaned and arched her back. Her tail flicked against his tip, but she held him back when he tried to lean in.

“Wait until I’m ready. Ahh… you really do know how to use those hooves. Keep going, but a little higher.”

Chester massaged and stroked the beautiful unicorn. His worked his way up to her shoulders. As he leaned in, she pressed her flanks up against him, pinning his shaft up against his belly. She moaned as the massage continued, but she kept rubbing against him in just the right ways to tease him. His shaft was flaring when he finally paused. Rarity smiled back at him.

“You’re nice and ready now. Time to give you what you’ve been waiting for. And looks like Rainbow Dash is ready to join in.”

Rarity leaned forward and leaned into a pillow while lifting her flanks into the air and pressing back until she was grinding against Chester’s tip. He had to grab her around the waist to steady himself as she slid his entire length in. He felt something behind him and a set of hooves squeezed his haunches as he felt something slick and hard poke at his hole.

He looked back. Rainbow Dash had a feisty smile. He didn’t have a good angle to see all of it, but she seemed to have some double-ended strap-on. She bit his mane to steady herself and thrust in deep. Chester moaned as the the fake shaft filled him.

“Been wanting to do this for a while,” Rainbow Dash said. “It feels good to play the part of the stallion.”

Rainbow Dash held him tight and started thrusting wildly with the toy. She moaned as the other end of it pressed against her each time she took Chester.

“Don’t get distracted by her,” Rarity said. “A professional should be able to keep going even with some sexy distractions.”

Chester tried to match Rainbow Dash’s rhythm, but she was going too fast. Each time he thrust into Rarity’s soft and inviting folds, Rainbow Dash would thrust twice into his tight hole. The toy kept hitting just the right spots, and he was slick with pre as his flared tip slid in and out of Rarity.

“Mmm… nothing could distract me from such an elegant mare like you.”

He leaned in and nibbled playfully on Rarity’s ear before planting a series of soft kisses. He slipped a hoof lower and circled it around, rubbing it over her firm nipples and her sensitive clit. She pushed back hungrily against his cock as her climax hit. He could feel it ripple through her body as her folds milked his shaft.

“Ah… Chester… harder! Oh! Don’t stop!”

“Ahh… almost there!” Rainbow Dash said.

Rainbow Dash was getting close, but that wasn’t slowing her down. Chester timed his motions in tune with Rainbow Dash’s. The force of her thrusts drove his own shaft deeper and deeper until he let out a skree as his tip flared and his seed filled Rarity.

Rainbow Dash kept pumping her hips against his, causing his seed to shoot out harder and in greater amounts than normal. She bit his mane and made one last series of thrusts before finally stopping. Chester could feel her warm fluids running down the toy as she panted and gasped.

The three of them stayed like that for a few moments as they all caught their breath. Rainbow Dash pulled out first. She gave Chester’s flanks a quick squeeze and rubbed his balls.

“Thanks for letting me practice on you,” Rainbow Dash said. “Maybe I could use this to surprise Soren or Quibble… ahh… I’d better clean up and get to bed. Gotta go practice in the morning.”

She walked off with the huge toy still hanging down beneath her. Chester kissed Rarity’s cheek and pulled out gently before helping her up.

“I hope that was everything you hoped it would be,” Chester said.

“Oh… darling… that was just what I wanted. It’ll be hard to be pleased with my usual choices after having you.”

She pulled him in for one more kiss before trying to tidy up her mane and tail with a bit of magic. She blushed as their combined fluids started dripping down her leg. She hurried off to go clean up.

Chester rolled onto his back and stretched out on top of the cushion in the middle of the room. He spent shaft was slick and messy, but he hardly cared. The air felt cold on it, but he displayed it proudly. The three mares left in the room all looked him over with slightly different expressions.

Fluttershy was sitting on the couch and blushing. She looked away when he tried to look into her eyes. Pinkie Pie was looking messy. She was stretched out and looked as if she had been rubbing herself with her hoof while watching. Starlight was over by a table on the other side of the room, but her smile said that she had been planning and waiting patiently.

“Here, eat and drink these,” Starlight said. “They’ll have you back up and ready for the last few rounds of fun.”

She levitated a glowing white potion and a plate of sliced mango over to him. He downed the potion. It tingled and fizzed as he drank it down, but it wasn’t a bad taste. It was sort of milky and sweet. As he downed it, he could feel a gentle heat in his shaft as it hardened to full size in a moment. The potion left him feeling hungry, so he quickly downed the sliced mango. He usually liked to savor the fruit, but he was feeling a different sort of hunger even more strongly.

“Mmm… thank you,” he said. “Now which of you mares wants to go next?”

Bold and Shy

Starlight snuggled up with Chester on the bed. She stroked his belly and shaft and smiled. Chester turned his head and could smell the arousing scent or Fluttershy nearby. She sat back with her legs spread to either side of Chester’s face.

“Fluttershy would have waited all night if I didn’t invite her to join me,” Starlight said. “And now you get both of us.”

“But when’s it my turn?” Pinkie asked.

“You go last,” Starlight answered. “We all remember what happened last time we let you go first during a party. You wore the stallion out because you wanted to make sure he had all the fun he could possibly have. Anyway, you just watch.”

“You’ll all get a turn,” Chester said. “And let’s hope we saved the best for last. For now, I have two lovely mares to please.”

Chester leaned his head back and to the side and laid it in Fluttershy’s lap.

“If you want more than my tongue to please you, just let me know,” he said.

“Oh, umm… that’s enough for me.”

Fluttershy blushed deeply. Chester nuzzled her thighs and nipped them softly with his fangs. Fluttershy gasped. Her cute little pink clit winked at Chester, and he leaned in to suck on it. Fluttershy’s wings spread wide, and she moaned. Chester pressed his face in to nuzzle and lick her. His tongue caressed her then slid down over her soft folds before pressing deeper.

“Alright, time for my own fun,” Starlight said as her horn glowed.

Chester could feel the magic on his cock and flanks. Starlight sat on his belly, facing away from him. She bent forward and her magic pulled his tip up against her tight folds before pushing it deeper. The magic moved his body in the perfect rhythm and after one more tingle of magic, his tip began to vibrate. Starlight’s magic took control, and Chester was definitely enjoying the ride as his body moved with its trained perfection without any effort on his part. Starlight moaned as she rode his thick cock.

He turned his attention back to Fluttershy. He could taste her sweet flavor as his tongue plunged deep into her folds. He swirled it around until he found the spot that made her tremble. He pressed it harder and was rewarded with a loud moan. Her folds tightened around his tongue. He kept going until he had to pull back up for a breath of air. He sucked her clit before pushing his muzzle between her slick folds and licking over the spot one more time. Fluttershy arched her back and cried out before a spray of her fluids drenched Chester’s face. He teased her a few more times until she was trembling and gasping.

Fluttershy pressed her hooves into his chest and pressed down against Chester’s mouth. She grinded hard against his lips and tongue. Her wings quivered and stuck straight out as her warm mess dripped over Chester’s face. He swirled his tongue around. She cried out and then leaned back.

Chester had to take a deep breath. He missed the warmth and scent of Fluttershy on his face, but he needed to catch his breath. He looked at Starlight and his eyes widened. She was levitating herself up and down, riding his shaft in all sorts of ways that wouldn’t have normally been possible.

She winked at him and her magic flashed. The vibration in his tip went even faster. Chester’s shaft was throbbing. He arched his back and let out a loud skree. Without the soundproofing spells, it would have woke up the surrounding blocks of Ponyville.

Chester couldn’t hold back, and Starlight seemed to know it. She slipped down until his entire shaft was buried deep inside. Chester grabbed her waist and pushed his balls against her as shot after shot of cum filled the mare. He kept thrusting and grinding until his body could take no more. After what seemed like forever, he finally was finished. He could feel the warmth of his cum filling Starlight and dripping onto his lap. He nibbled Starlight’s flank playfully before giving her a kiss.

She bent to the side to return the kiss before slowly standing up. The faint glow of magic surrounded her opening until she rolled onto her back and let it go. She blushed as the slick mess started to drip onto her tail.

“That was quite the noise you made,” Starlight said. She stroked Chester’s wings slowly.

“Mmm… you really didn’t go easy on me with all that magic. I’ve never seen a mare put all those spells together quite like that. And how was it for you, Fluttershy?”

“That was great! Umm… I better go clean up. Thank you for such a wonderful time.”

Fluttershy covered herself with her tail and slipped quickly out of the room.

Starlight rubbed the mess around with a hoof. She circled it around her clit then rubbed hard until she moaned and sprayed the bed.

“Be a good boy and help clean this up.”

Chester obeyed the command. Starlight was really getting into this, and that’s what he liked to see. She trembled as he licked her out before sucking on her slick folds. When he was done, she pulled him up and shared a messy kiss with him.

“Mmm… as smooth as the bat it came from. Ah… I guess we shouldn’t leave Pinkie waiting much longer. You two have fun.”

Starlight patted his cheek and went to go clean up.

Bouncy

Chester looked over to where Pinkie Pie had been. He wasn’t sure what he was seeing at first. A bunch of ropes were tied around the room. He finally spotted Pinkie Pie, and she was hanging upside down. She waved at him and motioned for him to join her. Chester flapped his wings until he was next to her then wrapped his tail around the rope so he could hang next to her.

Pinkie Pie smiled. “I thought it would be fun to do this like bats do!”

“We don’t actually do it upside down.” Chester chuckled. “But I like the idea. It might be a little harder, but if that’s what you want, I aim to please.”

“That’s usually my job.”

Pinkie Pie booped him on the nose and laughed before doing the same to his shaft.

“Such a messy stallion. I think you need a little cleaning up first.”

She licked off her hoof then untied something. The rope holding her steady slipped away, leaving a set of thinner ropes holding the pink mare. The ropes stretched a little and Pinkie Pie went lower before bouncing back up. She gave Chester’s shaft a huge lick as she moved up and down.

“Bungee cords? I like it. Ahh…”

Chester moaned as her tongue slid up and down his shaft. The mess from before was slurped up in moments. Pinkie seemed more practiced at this than he would have guessed. Her tongue kept teasing him until he was dripping, but she made sure not even a drop got to the ground.

Pinkie swung a little and bumped his face with her loose, wet pussy. He wasn’t ready the first time, but he gave her a lick the second time. They swayed back and forth in the air, licking each other until both were wet and panting.

“Hug me close,” Pinkie Pie said. “And we’ll get the real party started.”

Pinkie reached out. Chester wrapped his hooves around her. She bounced up and down, still upside down. As she bounced, she slid his shaft along her thighs. After a few moments of teasing, she held him closer and let his tip slide and press along her slick, warm folds. She pulled down a little more and drove half his shaft in as she bounced back up.

“Pinkie… ah…”

“That’s what I like to hear.”

The bungee cord kept her bouncing and drove his shaft in deeper with each motion. Pinkie Pie had the movement down just right so his tip would just barely slide out of her before back in with a wet noise as she moaned happily.

Pinkie handed him a bungee cord. “Tie this on, and we’ll have twice as much fun.”

He wrapped it around his middle while Pinkie Pie rode his shaft upside down a few times. She was making it hard to focus on the knots, but he finally got them done. He loosened the grip his tail had on the other rope and fluttered his wings to get a little bounce. He was rewarded with the tight, wet folds sliding over his shaft in a way that made him gasp.

“Let’s try a little more motion,” he said.

He flapped his wings until they were both upright then held them steady to let them slowly fall. Pinkie held him just enough to keep his tip from popping out of her. She hilted his entire shaft with a loud giggle as they reached the bottom of the rope. The cords snapped them back up, but the small differences made Chester and Pinkie slide up and down. The movements weren’t the expected back and forth of his usual thrusts, and it was driving Chester wild. His shaft throbbed, but they weren’t going fast enough to build up to his climax just yet.

Pinkie Pie gave him a kiss. “More.”

They spun, swayed, and bounced in the air. Pinkie surprised him by grabbing the stretchy cords and using them to bounce quickly on his shaft. He fluttered his wings and moaned as her tight warmth rubbed all over his cock. She pulled herself forward and squeezed tight as his flared tip pressed inside her. She pressed a hoof down against her belly, giving his tip an even tighter squeeze as they rapidly bounced up and down.

Chester couldn’t hold back. He buried his face in Pinkie’s soft mane and filled her with shot after shot of cum. They were still upside down, so nothing spilled out. Pinkie pressed her hoof against her little nub before her body clamped down and trembled as she climaxed. They slowly bounced less and less and they pressed against each other until the haze of bliss slowly ended.

Pinkie laughed and patted her slightly larger belly. “I’ll have to do it like a bat would more often.”

He hugged her with his wings. They snuggled in the air for a long time until Pinkie finally had him pull out. She undid his rope first, and he helped her get safely to the ground as he untied her.

“That was fun, and possibly the most unique way I’ve had sex in a while. Thank you, Pinkie.”

“It takes a real stud to please a whole castle full of mares. But you better clean up and go back to Applejack. She gets up really early. And just maybe… she’ll share you with us sometime. But whatever happens, make her smile. That’s what matters most.”

Author's Note

Okay, that's a wrap for this story. I tried to take it more in a slice of life direction with Applejack and her family slowly accepting Chester, but I wasn't finding any ideas there that were actually very fun. I stalled on writing the story a bit.

I came back to it later and decided I'd wrap it up in an easier way with a bit of fun for every pony. I hope you all enjoyed that choice.

I was also a little bad about editing and putting up the chapters, so sorry for the long breaks. I do have some good ideas of something fun to work on next, so I hope you'll continue to enjoy my stories. Thanks for reading!