Two Hedgehogs and a Fox: An Ageplay Story

by milesprower06

Dress Up

Tails grimaced as he forced himself to swallow the third bite of mashed prunes that Sonic shoveled into his mouth, then stuck his tongue out momentarily as he scraped it against his front teeth to remove the remnants.

"Don't give me that now, they're good for you." The hedgehog chastised him. Tails smirked as another bite was scooped into the spoon. Sonic seemed to like teasing him and putting him through the not-so-pleasant parts of infancy, but the fox had to admit that it was part of the experience.

He was a bit wet, and the rule was that if he wasn't completely dry at bedtime, he'd be changed into a fresh diaper, and Amy already let Sonic know that it was his turn to do the bedtime routine, which meant bath, change, bottle, and bed.

"So what are you gonna be doing when I'm with mommy tomorrow?" Tails asked as he swallowed the next bite of prunes.

"Probably go for a nice long run, been a few days since I've done that. Not that taking care of you hasn't been super fun, but it'll be nice to get back into what I usually do to relax." Sonic told him. After a few more bites, the bowl was scraped clean, and he quickly took it to the sink, rinsed it out, and picked Tails up out of his high chair, carrying him up to the second floor, and into the bathroom, where he untaped the fox's damp diaper and got him into a tub of warm water.

Tails still very much enjoyed the bathing process, loving how clean and fluffy he felt at the end of it each night.

"What about you? Has mommy told you if she's got anything planned for the two of you?" Sonic asked as he drizzled shampoo onto the top of Tails' head in between his ears, before beginning to work it in.

"Nope. Maybe she wants to play it by ear, or maybe she has a surprise." Tails replied as the soap began to get sudsy, and Sonic worked his way down to his chest, stomach, back, tails, and diaper area.

"Well, if she does have any surprises in store, she certainly hasn't told me. Maybe she thinks I'd spoil it. Or maybe it'll be a nice relaxing day at home, where she gets some one on one practice in. Who knows?"

After a quick rinsing, Sonic grabbed the air dryer, and got his best friend dried off and brushed, before taking his hand and walking him back to the nursery. Amy was already in their bedroom, but it appeared she had taken the time to prepare a bottle of breastmilk, which was currently sitting on the right arm of the rocking chair next to the crib. Grabbing him under his arms, Sonic lifted Tails up onto the changing table, and grabbed a fresh diaper, unfolding it, and slid it under him, getting it fastened around his tails.

"And I don't think you really got a chance to get this taken care of today either, buddy," Sonic said, noting Tails' growing erection. Following Amy's example, he grabbed the bottle of baby lotion, got a small amount on his palm, and went about helping his pal with achieving release to get a good night's sleep.

Being the first time Sonic had helped with this, Tails blushed lightly, and took note of how the hedgehog certainly knew was he was doing, deftly moving up and down with his fingers, working in the lotion, and also teasing his head and tip with his thumb at just the right moments.

"Yep, you've been pent up all day. Time to let it all out..." Sonic told him, sounding like this was just part of a nightly diaper change that an adult infant would need to sleep soundly.

In a way, it was.

Try as he might to make it last longer, the fox's libido wasn't having it, and after a few moments of thrusting, Tails let out a gasp.

"Ah! Daddy!" He said, keeping as quiet as possible as the first rope of white seed burst from his tip. Sonic had already angled his shaft, and it, and the following five bursts spilled out onto his fresh diaper. When he was down to a dribble, he let go, and grabbed the baby powder from the shelf, giving his groin and bum a liberal sprinkling, and also dusted the cum-covered inside of his diaper. Before taping it up, Sonic walked over to get the bottle Amy had set on the rocking chair, and gave it to Tails, who immediately began to nurse from the rubber nipple as the hedgehog grabbed the cleaned chastity cage from the shelf. Now that he had shrunk back down, Sonic carefully got Tails' shaft comfortably placed in the confines of the cage, and got it closed and locked, before bringing the front of the diaper up, smoothed the front against his stomach, and got the tapes tightly and securely fastened, double checking the leg guards to make sure they were properly in place. By the time he went to the closet and came back with his footed pajamas, the fox was half done with the bottle.

"Alright, just a quick little break so we can get this on you." Sonic said, taking the bottle from his lips, and setting it to the side as he sat Tails up and got his bare feet tugged into the leg holes, bringing it up his stomach and chest, and then got his arms in, before getting the velcro hole fastened around his tails, and zipped it up the chest to his neck, being careful not to get any fut caught in the zipper. Tails hopped down from the changing table onto the floor, and walked to the crib, climbing inside. Post-orgasm clarity or not, he really liked how his diaper gave off a muffled crinkle underneath the pajamas.

Once he was situated in the crib, Sonic knelt next to the open bars and returned the half-empty bottle to his lips, softly petting his head as he finished the contents.

"Didn't think it was possible, but we've managed to make you even cuter, buddy." Sonic told him, getting a bashful smile from around the nipple. With a final bubbly gulp from the bottle followed by air squeezing through the nipple, Sonic took it from him once again, and leaned forward.

"Sweet dreams, pal. See you in a day." Sonic said, kissing him on the forehead before raising the bars. Tails let out a big yawn before he had gotten to the door and shut off the light, leaving the door open just a crack. He heard the very faint running of water from the kitchen sink as Sonic rinsed out the bottle, and didn't even stay awake long enough to hear him come back up the stairs to retire for the night.

Tails slowly came to, as the slowly rotating emeralds on the mobile above him came into focus in the dim illumination of the night light. He sat up, wondering what time it was. There wasn't a clock anywhere in the room, but judging by the blackness outside his window, it was nowhere close to sunrise yet.

All he knew was that there was a slowly increasing urgency in his bowels. His rhythm of answering nature's call didn't usually involve getting up in the middle of the night, but he was assuming that yesterday's enema threw said rhythm out of sync. It didn't feel nearly as urgent as he had felt mere minutes after yesterday morning's treatment, but it was also something he wasn't keen on repeating, so he didn't want to hold this through the night and have it result in more cramping.

Amy did say she wanted at least one messy diaper every 24 hours anyway, and that meant that if he didn't do it now, he would have to do it first thing in the morning to avoid another enema on the changing table.

Sitting up and facing the bars, Tails got onto his knees and then up to his feet, bending down into a squatting position. He focused, but not too hard, and slowly pushed, his tails curving up to his back.

It wasn't nearly as massive as yesterday had been, but what it was, was hot. Almost too hot at first, but as it met the resistance of his securely fastened diaper and began to spread out, it quickly lost its immediate heat and became a slightly cooler, lukewarm mush. Two short pushes was all it took, and again, it wasn't nearly as alarming or big as yesterday's enema-induced load had been. But he still blushed furiously, knowing that this was his first unassisted messy diaper, and he now stood against the bars wondering what to do now. Did he go towards the baby monitor, get their attention? Do a mock cry into it?

No, he quickly decided against that. Either they would discover it in the middle of the night if and when they checked on him, or first thing in the morning. It had already spread around considerably as the diaper was held closely to his fur by his snug pajamas, and it spread even more as he sat back down on the mattress, causing him to shudder, but he didn't want to think about it too much and have an erection painfully press up against his chastity cage. Taking a deep breath as he laid back down on his pillow, the stench had already reached his nose, and it made him feel positively infantile, as he took another breath, and slowly closed his eyes, descending once more into sleep.

"Alright, have fun today, sweetheart." Amy told Sonic at the front door, giving him a quick kiss as he stepped outside.

"You do the same, hun." Sonic said with a wink, and he was off in a flash.

Sipping at her fresh cup of coffee, Amy closed the front door and headed up the stairs, turning left to the nursery. She opened the door, and she hadn't even stepped onto the room's carpet before the smell hit her like a brick wall, and her nose instinctively scrunched up in response.

"Uh oh, do we have a stinky fox this morning? I had a feeling that's what Sonic was going for when he gave you that bowl of prunes for dinner last night." Amy said, stepping into the nursery, as Tails woke up with a stretch. She came up to the crib, lowered the bars, and picked the fox up, taking him over to the changing table and began removing his pajamas, before laying him down, and untaping his diaper.

"What a good boy, I'm so proud of you for doing it on your own." Amy told him as she opened it up and looked at the contents inside before grabbing the pack of wipes. Tails' cheeks flushed red at the praise, seeing as how everyone of his role-playing age would be complimented for getting closer to potty training, not reversing it.

The first thing she did was unlock and remove the chastity cage, and set it aside for cleaning, before using the damp front of the diaper to wipe off as much of the smeared mess off of his fur as she could, before pulling out several wipes and used them one by one to clean off his diaper area, depositing the wadded up used wipes into the opened diaper between his legs. Once he was sufficiently clean, she pulled the diaper out from under him and rolled it up, throwing it away into the diaper pail next to her, and deduced that the wipes had done a good enough job to not warrant a short spray-down in the tub after every messy diaper that he had.

She grabbed a fresh diaper from the shelves below, and before unfolding it, used it to fan the fur of his groin, slightly moist from all the wipes she had just used. It was satisfactorily dry after a few moments, and she unfolded the diaper and slid it under, fastening the back around his tails, and quickly getting him and the diaper powdered, before bringing it up and taping it closed.

She certainly noticed how changes were becoming easier and quicker.

"Alright, little one. Time for breakfast." Amy told him, picking him up and taking him over to the rocking chair, giving him what was by now a routine breastfeeding. After that, she stood him on his country road play mat.

"Alright, it's just you and me today, Tails. What would you like to do?" Amy asked him, standing in front of him, waiting to hear what he had to say.

"You didn't have anything planned?" Tails asked.

"Nope, apart from seeing how I do from one-on-one time. Anything you'd like to do? Any more fantasies you'd like to get closer to?" The hedgehog asked.

"Well..." Tails began, unsure if he wanted to say what had started to come to his mind.

"It's alright if you need time to think about it, hun." She told him.

The fox then had an epiphany; why was he being so hesitant. Here he was, having been babied by his two best friends for the past two days. If anyone was going to understand this request, it would be them.

"Could... Could I try on some of your dresses?" He asked, his face becoming the most delightful shade of red.

Amy's eyes widened for just a moment, but her face didn't turn to a look of shock or disgust. She quickly composed herself, and gave him a soft smile, before offering him her hand. Once he grabbed it, she silently walked him out of the nursery, down the hall, and over to the bedroom she shared with Sonic. Walking past the bed, she brought him into the darkness of the walk-in closet, before releasing his hand, and flipped the light switch.

"What would you like to try on?" She asked, as if he was a customer in a store's clothing section.

The poor fox was nearly quivering as he looked at his options. There was of course several copies of Amy's signature red dress. He looked past those, and the first thing to catch his eye was a light turquoise skirt. Amy's closet was impeccably sorted, and right below that was a pair of matching sandals. On the rack above, was a brown belt, and a white blouse with a pink flower pinned on the right shoulder. One by one, he took the hangers off of the racks and turned back towards Amy.

"You sure you're okay with this?" Tails asked, his nervousness absolutely apparent.

Amy gave him another reassuring smile.

"Sweetheart, you remember that book I told you about? About the various kinks and fetishes? Remember when I said that ageplay was just five pages among other fringe kinks? Well, cross-dressing was an entire chapter. It's hardly fringe, and much, much more common. I don't know why you're so nervous. I've been changing your diapers for two days now." She teased.

It was enough to get a smile out of him as she helped him remove the articles of clothing from their respective hangers. He gently tugged on the blouse first, and it came down to cover the top quarter of his diaper. After that, Amy helped him step into the skirt, pulling up and got it around the blouse before feeding in the belt through the loops. Lastly he stepped into the sandals, before Amy led him over to the full length mirror, and his cheeks lit up when he saw himself, and he couldn't help but smile.

"What do you think?" Tails asked Amy, who was standing behind him, watching as he admired his reflection.

"What do I think? Honestly I'm pretty jealous right now."

"Jealous? How come?" The fox asked.

"Because it's pretty darn easy for you to look cute in pretty much anything, clearly." Amy said, motioning to his current outfit.

He gave a little twirl, watching himself in the mirror.

"Hmm..." Amy began to think. She stepped up behind him, and lifted the back of his skirt. "Well... This skirt certainly makes diaper checks easier, so... Do you want to spend the day as my little girl?"

Tails felt a shiver go up his spine as his good friend immediately offered to fulfill a new fantasy.

"Am... Mommy... I don't know what to say." He admitted.

"You don't need to say anything, Tails. I wish you wouldn't think of this week as a chore on our part. I promise you, we're enjoying this just as much as you are," The hedgehog reassured him. "So, what do you say?"

Tails couldn't nod fast enough, and then took both sides of the skirt in his fingertips, and gave a short curtsy.

"Thank you, mommy. Thank you so much."