Chapter 1
Trenderhoof trotted along the path towards Fluttershy’s cottage, intent on writing a ‘Where Are They Now’ article about the shy pegasus’ old modeling career. Many had been shocked with how she had given up her fame so quickly after attaining it, so he was determined to get to the bottom of it.
The townsponies told me she should be home at this time… he thought, stopping briefly to itch a scratch on the inside of his leg. I’ll breeze through this like I always do, get the story I need, and then head back home on the last train out of Ponyville. Trenderhoof looked up at the sky and noted that the sun was already falling. He knew he didn’t have that much time left, so he was going to have to make things quick.
As Fluttershy’s cottage came into view past a clump of bushes, he quickened his pace a bit, for he did not want to be caught in Ponyville without a place to stay. The only hotel in the town was already at max capacity with some ponies on vacation from Trottingham, so his only choice was to leave on the last train out or he’d be stuck in a jam.
He crossed the small bridge and made his way up to Fluttershy’s front door. As he raised his hoof to knock, he heard singing coming from behind the house. His ears flicking every which way to pinpoint where the sounds were coming from, Trenderhoof walked around the side of the cottage, his ears flicked forward. Walking around the corner, his ears were graced by one of the softest and sweetest voices that he’d ever heard, and that was saying something.
His jaw hanging open, he mindlessly walked forward on autopilot. The beautiful voice was coming from behind a small fence, hidden by a few trees.
“H–hello?” he stuttered, mentally kicking himself in the flank for sounding so weak. The voice immediately disappeared. “It’s me, Trenderhoof. I was that pony who wrote the article about the event that your friend, Rarity…” He walked through a small gate in the fence, a small shiver running down his spine as he uttered her name. “ran the last time I was in town.” At that, he walked around the last tree, letting his gaze fall upon the one with the beautiful voice. She was hiding behind her mane, something that puzzled him for a brief moment.
“Oh! Yes, I remember you,” Fluttershy said, looking up at him. Shaking her mane from her face, she trotted up to shake his hoof. “How do you do?”
“Quite well, thank you,” Trenderhoof said, looking past Fluttershy. A bunch of different animals all sat behind her, staring at him. “Uh… what’s up with all of those animals?”
“I take care of them!” Fluttershy said with a nervous, yet friendly smile. “It’s what I like to do in my spare time. I find that it’s really rewarding!” She glanced over her shoulder and smiled warmly at the large group of forest critters before turning back to face him. “Just say hi! They’re really friendly!”
They don’t look too friendly… He locked eyes with a bear that sat behind the rest of the group. He couldn’t tell if he was giving him the stink-eye or if he was just checking him out. He chuckled nervously and gave them a shaky wave. “Um… hello?” All at once, they all hurried over to him, chirping happily as they surrounded him. A few bunnies nuzzled his fore legs, a pair of blue jays landed on his back, and a couple of young beavers stood on their hind legs, reaching up for his neck as if they were asking to be held.
Slightly startled by the sudden change of attitude, Trenderhoof tried to take a step back but tripped over his legs, making him fall flat on his side. That gave the furry critters the perfect opportunity they needed. He felt so many little claws poke him all over, making him close his eyes and freeze up. Seconds passed as he felt more little pricks and pokes, and then he heard that wondrous voice again.
“Aw, you look so cute!” he heard Fluttershy say. Is she talking about me? In any case, I wasn’t expecting her to say that… Cracking an eye open, Trenderhoof looked up and found the birds sitting between his ears. He gently shook his head, making them take flight, then looked over his shoulder. The beavers were sitting right next to each other on his side and the bunnies were all snuggling with each other right on his cutie mark. “Heh, that is kinda cute,” he said, letting a little smile slip on his face.
“See? I told you they’re friendly!” Fluttershy said. “I was just about to feed them. Want to help?”
“Sure, I don’t see why not,” Trenderhoof replied, using a hoof to gently push the animals off of him.
His original task forgotten, he and Fluttershy fed each animal. He thought the task would have taken him only a few minutes, but he soon lost track of time. An hour later, as the sun sunk below the horizon, his heart skipped a beat as he realized his mistake.
“Um, hey, Fluttershy…” he started lamely, prancing in place. “Do you know what time it is?”
“Not off the top of my head, no, but I have a clock inside,” she said, dropping the sack of birdseed she held in her hoof. “Give me a second and I’ll go check for you.” Fluttershy trotted past him then stopped. She looked back at him and asked, “Oh, did you want something to drink? I really appreciate your help, by the way.”
“No thanks, I’m good for now. It’s just kinda important that I know what time it is.” Trenderhoof glanced at the setting sun. “I just need to be outta here before the last train leaves. Oh! And that reminds me… when you get back I want to ask you some questions.”
“Okay, just, um… give me a few moments,” Fluttershy nodded once and turned around, resuming her trot to her house.
Trenderhoof watched her walk away, his stomach twisting itself into knots over his nervousness. As the yellow pegasus neared her house, he couldn’t help but notice the alluring sway of her flank. He knew it wasn’t proper or polite to stare at another pony’s privates, but he couldn’t look away either.
The door slammed shut behind her, blocking his view. Damn… he thought, rolling his eyes. As he waited, he fantasized about bedding that sweet mare. Trenderhoof felt his dick twitch in his sheath as it started to grow, so he bit his tongue as hard as he could, focusing on the pain to try and keep himself from popping a boner in front of all the animals.
“It’s a little after eight!” Fluttershy said from behind him, making him jump. He’d been so focused on trying to keep his boner down that he didn’t hear her approach.
“After eight?! Crap, I missed the last train out!” Trenderhoof stomped the ground with his right hoof. He shook his head and snorted, staring off into the Everfree Forest until he felt a soft hoof touch his shoulder, making him look around.
“You don’t have a place to stay?” Fluttershy asked, cocking her head to the side. Trenderhoof shook his head. “Why don’t you stay with me tonight? It’s the least I could do to pay you back for helping me take care of the adult animals. I can make you dinner if you agree to help me with all the baby animals inside. I must warn you though, they can get a little rowdy, and there are a lot of them.”
Trenderhoof’s eyebrows shot up. She just invited me inside her house? To stay the night? I might just get this interview after all! “Sure, I wouldn’t mind helping you out some more,” he said, laying as much charm into his voice as he could.
“Thats, um… I’d appreciate it. It’d be so nice to get some extra help around here, if only for a night!” Fluttershy said, a friendly smile on her face. She nodded back towards her house. “Come on in, I can make us some potato soup before we get to work.”
Trenderhoof nodded and followed Fluttershy into her cottage. Like before, his eyes never left her sexy little flank except for the brief moment that Fluttershy glanced over her shoulder. Their eyes met and they both looked away, each blushing.
“Just pick whichever seat you want,” Fluttershy said, pointing at a small table in the corner. “I’ll put the soup on, and then we can take care of the little ones in a bit.”
Trenderhoof heard little chirps and whines coming from somewhere down the hallway. “Am I correct in guessing that you have them in some room?”
“Mhm,” Fluttershy said. “They like to stay inside one of the smaller rooms I have during the cold nights.”
“That makes sense. I mean, who would want to freeze their flank off when somepony as nice as you would take them in and take care of them?”
“Exactly.” Fluttershy poured the pot of soup into two bowls, then carried them over to the table. They ate their meals quickly and washed the dishes. “You ready to earn your keep?” she asked. Before he could respond, she turned around and trotted out of the kitchen.
Did she just say what I think she said? he thought, frozen in place. His heart beat fast, thumping away in his chest. He was only broken from his thoughts when Fluttershy poked her head back around the corner.
“Hey, you coming?” she asked.
“Y-yeah!” Trenderhoof stuttered, throwing a fake smile on his face as he trotted towards her. “After you!” He snuck another look at Fluttershy, and much to his amazement, he actually managed to get a full view of her marehood.
“They’re just through here,” Fluttershy said, her hoof resting on the door’s handle. “Why don’t you go and grab some supplies from the closet? It’s the door across from this one.” At that, Fluttershy opened the door and walked inside, leaving Trenderhoof standing alone in the hallway.
“What kind of supplies do you need?” Trenderhoof asked, poking his head through the door.
“Oh, just food and stuff. I have a few bags I need you to grab.” Fluttershy bent down and lowered her head to the floor so that she could whisper to a baby bunny snuggling with its mother.
Trenderhoof’s eyes went wide as he stared at the sight. If he didn’t know better, he would have sworn that Fluttershy was presenting herself to him. He didn’t want to say anything about it though, for the chance of losing a place to stay the night was pretty high if he said the wrong thing. So, instead of pushing the issue, he tore his gaze away from the enticing sight and grabbed the bags of supplies that Fluttershy wanted him to get. After setting them down next to her, he asked, “Hey, do we need anything else?”
“Actually, yeah, we do.” Fluttershy flapped her wings a couple of times and landed next to him, touching down with minimal noise. “We need to get some more diapers from the diaper room; the ones in the bags won’t be enough.”
“Alright then,” Trenderhoof said, following Fluttershy as she led him further down the hall and through an open door. What he saw made him stop in his tracks. She sure wasn’t lying… Diapers of all sizes lay neatly across the room. Shelves lined the walls, diapers neatly stacked next to each other on them. They ranged from sizes that would fit baby mice to ones that looked like you could fit a full-grown bear in them.
Fluttershy walked across the room and opened a cabinet near the floor. “Now I know I put them somewhere in here last week…” she muttered as she poked her head inside, once again unknowingly assuming the stance of a mare in heat who wanted to be mounted. Stop, man! Look anywhere but her ass! He clenched his eyes shut and tried to look away, but found that he could not.
This time, Trenderhoof couldn’t stop his boner from growing. He tried everything he could to stop it, but nothing worked. To make things worse, Fluttershy started swaying her hips back and forth as she rummaged around in the cabinet, making him grow harder and harder. He was at least at half-mast now; if he moved to touch it to see how hard it was, it would only serve to make him harder from the stimulation.
“Ah, found it!” Fluttershy said, carefully extricating herself from the cabinet with a few small packages of diapers.
Trenderhoof’s heart plummeted into his stomach. He tried to turn away, hoping that Fluttershy wouldn’t see his now rock-hard boner poking against his stomach. Things moved in slow motion as she turned around, and he followed her gaze right to his dick.
Fluttershy’s eyes went wide at the sight and she dropped the diapers. “Um, I– I–” Her eyes darted all over the place until it settled on an adult pony-sized diaper. “Here!” she squeaked out, holding the diaper in her hoof as she looked away out of respect.
Trenderhoof grabbed it without a second thought. He hurriedly yanked it up his hind legs, threaded his tail through the hole in the back, and used his magic to apply the tapes, making sure that they stuck in place. “Okay, we’re all good n–now,” he said in a shaky voice.
“You’re covered up?” Fluttershy asked, blushing furiously.
“Y–yeah, I am.” Trenderhoof sat down and scratched the back of his neck with a nervous chuckle. He wiggled his butt on the ground, noting that the thickness of the diaper made the hard, wooden floor much more comfortable to sit on. On top of that, the warmth of the diaper and the sounds of the the crinkly plastic made him relax a bit. “Huh…”
“Wha… what is it?”
“This actually feels really nice…” Trenderhoof said softly to himself, poking the front of his diaper, which just barely covered up his erect dick.
“What does?”
“The diaper. It feels, I don’t know… This is kinda embarrassing, but this is actually really comfortable!”
“It… it is?” Fluttershy asked curiously, cocking her head to the side. She glanced at the bulge in his crotch then looked away, blushing furiously.
“Yeah! You should try one on,” Trenderhoof said, using his magic to levitate one in front of her. “That looks to be about your size, right?”
“I– I think so,” Fluttershy whispered, her eyes locked on the diaper hovering in place.
“Would it be easier for you if i put it on for you?” Trenderhoof asked, his voice quivering with hesitant fear. He locked eyes with Fluttershy, holding her gaze with a hopeful expression, a gentle smile on his face.
He was relieved when Fluttershy smiled back at him. “I’d… I’d like that,” she said. “Do you want me to lay down on something?”
“Only if you want to.” Trenderhoof waited for Fluttershy to lay on her back, then approached her. He cocked an eyebrow at her covering her marehood with her tail and chuckled. “You know you’re gonna have to let go sooner or later, right?” Fluttershy silently nodded back at him. After a couple of moments, she let her tail go, revealing her moist marehood to him. He didn’t say anything about it, and instead went about diapering her up.
“There we go,” Trenderhoof said. “How’s it feel?”
Fluttershy looked up over her belly and poked the front of the diaper, marveling at how soft it was. “You were right about it being soft…” she said, her voice full of wonder. She rubbed the front of the diaper right where her marehood would be, making her left hind leg kick on its own. Pulling the diaper tighter up against her, she started massaging the front of it again, letting out an unintentional soft moan. “It does feel a bit weird though, being back in diapers,” she said, still rubbing the front of her diaper.
“Does, um… masturbating into it feel good? Judging from the sounds you’re making, it sure sounds like it,” Trenderhoof said with a nervous chuckle, praying that he hadn’t gone too far.
“Eep!” Fluttershy yanked her hoof away from her crotch, where a tiny rip in the plastic was quite apparent. They both looked at each other’s crotch, then locked eyes with each other, breathlessly waiting for the other to speak first.
Trenderhoof took the lead by doing the most daring thing he’d ever done before. He quickly closed the distance between them and planted his lips on Fluttershy’s, surprising the frightened mare. He felt her tense up then relax a few moments later, and as the need for air built up, he broke the kiss, a strand of saliva connecting their mouths.
“I– I couldn’t he–help myself,” Trenderhoof stuttered, rubbing his leg with a hoof. “You were just so cute, and I thought we had a thing going, and–” He
“Want to take things upstairs?” Fluttershy asked, her voice quivering.
Trenderhoof’s ears flicked forward. “Come again?” he asked, unable to believe his ears and his luck.
“Do you, um… want to take things upstairs?” Fluttershy grabbed a new diaper and put it on herself, then stuffed a few more inside of an empty bag.
“Celestia knows I’d love to, Fluttershy, but first I need you to tell me where the bathroom is at.” Trenderhoof started fidgeting. “I’ve been holding it in since dinner.” He felt his bladder twinge as the pressure grew a little bit worse. His dick softened a little, for the pressure in his bladder was taking his mind off of all of the arousing thoughts and ideas flowing through his mind.
Fluttershy giggled and pointed at his crotch. “Hehe, you’re wearing it!” She covered her growing smile with a hoof and stared at him, wondering if he’d actually use the diaper for its original purpose. “You’re wearing a diaper, you know. Might as well get some use out of it!”
“But, I… er, oh, alright,” Trenderhoof said with a sigh. He forced himself to relax and imagined himself standing in front of a toilet. Moments later, he heard a faint hissing come from inside the diaper he was wearing. His eyes shot open as his bladder quickly emptied itself into the diaper. Thankfully, the diaper absorbed it all and didn’t leak a single drop. In fact, Trenderhoof was sure that he could have given it a few more wettings without a problem.
After a quick change, the two of them trotted upstairs, Fluttershy wet and Trenderhoof as hard as a rock.
“I’m going to freshen up really quick,” Fluttershy said, her cheeks flushed red. “I’ll be just a moment.” She trotted into the bathroom and closed the door behind her.
“Alright then.” Trenderhoof glanced about the cozy little room. A large dresser and bed took up most of the space in the room, leaving just enough space for a pony to walk around without bumping into things.
As he waited, Trenderhoof sat down, his dick comfortably encased by the diaper. It felt so warm and soft, making him send a hoof downwards. He rubbed the front of it, back and forth until he felt a bead of precum escape from his tip, only to be absorbed by the diaper. Hehe, there won’t be a mess because of these diapers! We won’t have to clean the sheets or anything! At that moment, Fluttershy opened the bathroom door slowly, making his head snap up.
“Enjoying yourself?” Fluttershy asked coyly as she trotted up to him. After planting a little kiss on his cheek, she whispered, “Let’s do it under the sheets…”
That got Trenderhoof’s attention quick. His dick held snugly by the diaper, he walked up to the bed and used his magic to pull the sheets back, allowing Fluttershy to slide in first. Once she was in place, he slid in next to her then pulled the sheets over them.
“So, um… what did you have in mind?” Trenderhoof asked, laying a hesitant hoof over Fluttershy’s side.
“I– I don’t know,” Fluttershy whispered back, pulling the sheets tighter. “This is kinda my first time…”
Trenderhoof chuckled, drawing an inquisitive look from Fluttershy. “Don’t worry, it’s my first time, too. I just never imagined that the first time I had sex would be while I wore a diaper with a really beautiful mare.”
“Aw, you don’t mean that…” Fluttershy blushed and looked away.
“I do…” Trenderhoof said softly, leaning in. He pulled Fluttershy into a small kiss, and a few moments later, Fluttershy was on top of him, grinding her diaper against his. He felt her’s squish against his, and it felt warm to the touch. He felt his dick part her lower lips ever so slightly as they spread as much as they could around the surface of his dick.
“Getting a little excited, huh?” he asked with a smile. Fluttershy’s lips were only a few inches away from his, so he lit his horn and used his magic to gently guide her lips to his. They made out for a brief minute, and just when he was about to use a little tongue, Fluttershy broke the kiss.
“I want you inside of me,” she whispered into his ear. “Just please be gentle…”
“Okay…” Trenderhoof whispered back. Letting go of Fluttershy for a moment, he pushed the front of his diaper down, freeing his dick from the comfy confines of his diaper. It lightly smacked the front of Fluttershy’s soft, crinkly white diaper, making him bite back a soft moan. Lighting his horn once more, he gently pulled Fluttershy’s diaper to the side and lined himself up. “My my my… somepony is really excited down here,” he said, placing his hooves on Fluttershy’s padded rump.
Trenderhoof gently pushed down with his hooves while pushing up with his hips, slowly but surely working himself inside Fluttershy. Her wetness provided more than enough lubrication for him to gain entry without any problem at all. Right before his head was about to slip inside, he paused. “Ready?” he asked, just to be sure.
Fluttershy didn’t respond right away. Instead, she lay down on his chest and tucked her head under his chin. “Okay…” she whispered. “I”m ready…”
“Alright, here we go…” Trenderhoof whispered back. He felt her quiver a little bit, so he wrapped his hooves around Fluttershy and rubbed her back reassuringly as he slowly pushed himself inside her. As soon as the head popped inside her, she gasped softly, making him stop. “Does it hurt?”
“Kinda, but in a good way…” Fluttershy nuzzled his neck. “Keep going, stud. Oh, and one more thing…” She lifted her head to his ear. “Finish inside me…”
“You got it,” Trenderhoof said, sinking the rest of his shaft into Fluttershy’s pussy, making her moan and tremble in his grasp. Her pussy clenched down on his rod tightly, nearly making him cum on the spot. He held himself back though, biting down on his cheek to force himself from focusing on the pleasure too much.
Once Fluttershy had laid her head back in the crook of his neck, he pulled himself out then thrust himself back in a little harder than before, working himself all the way back in. After the first few thrusts, Fluttershy started rocking her hips in time with his thrusts, pushing him near the edge. Each thrust made a couple drops of Fluttershy’s arousal slip down his shaft to be absorbed by his diaper, making it start to swell and warm up, a fact that he instantly took note of.
As he neared the point of no return, he slowed his pace to a more tender one. “I’m so close,” he breathed into Fluttershy’s ear, wincing as he felt her pussy clamp down on his dick.
“Sa– oh… right there…” Fluttershy moaned as the tip of his dick grazed her G-spot. “Same here…” She planted her lips on his, then made a small trail of kisses down his face and neck. “I want you to rub my clit through the diaper, Trend… Fuck me so hard I’ll walk funny for days…”
Trenderhoof grinned. Building back up to a feverish pace, he had Fluttershy moaning within his embrace with each and every thrust within seconds. As they both neared the edge of no return, Trenderhoof lit his horn and focused his magic on Fluttershy’s clitoris, making her feel a plethora of sucking, rubbing, and flicking motions all at once.
“Oh, Trenderaaahah!” Fluttershy cried out as she came. Her body tensed up as her mind was wracked by wave after wave of pleasure.
Trenderhoof held on for as long as he could. Her pussy clenched down harder than ever before, making his head flare up. A moment later, his balls twitched and sent his load deep inside her, pumping her full of his hot seed. His flared head made it so that none of it seeped out of her, and as they rode out their respective orgasms, Trenderhoof used his magic to pull Fluttershy’s head up into a kiss. Fluttershy was especially forceful, sending her tongue into his mouth as he shot a few more weak shots into her.
The two of them slumped down, resting against the other. Trenderhoof’s softening dick was still inside Fluttershy, keeping his cum deep inside of her pussy. As Fluttershy panted, he slowly pulled himself out of her and pulled her diaper back into place right before his cum slipped out of her and onto the sheets. “I want you to push it out,” he whispered with a sly grin, slowly massaging Fluttershy’s pussy through the diaper. He felt Fluttershy nod against his neck, then he felt her tense up as she pushed. “Thaaaaat’s a good girl… Filling your crinkly diaper with cum…” he said, nibbling on the tip of Fluttershy’s ears, still rubbing her through the diaper. Trenderhoof pushed his softening length back inside of his warm diaper, smiling as his sensitive tip rubbed against the area where it had soaked up Fluttershy’s arousal as they had fucked.
“You know, I think I just want to go to bed…” Fluttershy whispered as she slipped off of his stomach. “Wanna cuddle?” she asked, pressing her back up against his side.
Heh, why ask if you’re going to do it anyways? Trenderhoof thought with a chuckle as he wrapped a hoof around Fluttershy. “You know it, ‘shy,” he whispered, making himself comfortable. "But what about the babies downstairs?"
"Oh, most of them were already asleep when we went to check on them. I left some food in the room for them, so they'll be fine till morning," Fluttershy said with a loud yawn. She snuggled closer to him, pressing her padded rear into his crotch.
"Oh, alright then." He fluffed a pillow for his head then tucked the sheets in around him with a content sigh, and before he knew it, Fluttershy was already asleep in his embrace.
Aw crap, I didn’t get that interview… Laying a small kiss in between Fluttershy’s ears, Trenderhoof lay his head over hers and closed his eyes. Hehe, maybe I’ll be able to ‘interview her’ when we go for another round in the morning….