wittlesissybaby
Season's Greetings
Published: December 21st 2022, 5:04:24 pm
“How’s your diaper? Is it nice and wet yet?”
Drew kept tugging on his ruffled skirt, but no matter how much he tried, he couldn’t get it to cover the poofy pampers underneath.
Penny smirked as she leaned over to peek at the indicator line. “Well it’s nice and blue, but the crotch isn’t as yellow as I would like, do you need more to drink?”
Before Drew could say anything, the nipple of the baby bottle was pressed into his mouth. He whimpered and tried to protest, but her stern look reminded him of the threat she’d made earlier: if you so much as hesitate for a second in there, I will pull that diaper down and blister your behind in front of everyone!
Drew continued suckling the milk from the bottle, sparing a glance behind him at the couple in their tacky sweaters. Drew and Penny had been waiting for over an hour. Their appointment was supposed to be at 2:30. Or, at least, that’s what Penny had told him…
After he’d finished his bottle, Penny lifted his skirt so she could watch his diaper swell while he “went tinkle”. She laughed when he was done, patting his soggy crotch.
Drew tensed a bit. He had spent the last 6 weeks in chastity. Out of nowhere, Penny decided to unlock him before getting him dressed this morning.
His uncaged cock grew almost instantly at her teasing touch. He glanced behind him again, humiliated at how hard he was in his pissy pampers.
“Mr. and Mrs. Schaefer?” A lady with a clipboard called, “we’re ready for—oh!” Her pen and jaw fell to the floor. She stood there aghast for several awkward seconds before finally collecting herself and clearing her throat. “Umm..you’ll uh..be in room 3 with Amanda.”
Amanda was busy setting up the camera when they came in. She gave a quick glance and smile at first, then did a triple take as her jaw came off its hinges.
“Uh…hel-lo there!” She sputtered, fumbling behind the light stands as she awkwardly tried to act professional. She shook Penny’s hand, unsure of how to greet the other. “Who’s umm…who’s this…little…guy?”
“This is baby Drew!!” Penny answered for him, nudging Drew forward.
“Hi Drew,” Amanda said, visibly uncomfortable but trying to make the best of it, “I like your…outfit…”
She kept noticeably glancing at Drew’s droopy diaper. Drew, seeing this, tried to tug down his skirt again, to no avail.
“So…” Amanda said, trying to move things along, “what will we be shooting for today?”
“Christmas Cards.” Penny replied with a wicked grin.
Amanda blinked, a bit shell-shocked, but continued on. “Both of you? Or just…”
“Just her.”
Amanda nodded, checking her clipboard, “okay, well I see you got the Premium Package, that will be 100 shots. You requested that you wanted the ‘Baby Girl Nursery’ background, is that correct? Or do you want something a little more…Christmasy?”
“No, that will be just fine, thanks.”
“Okay, well, just give me a couple more minutes to get ready and then we can begin.”
Penny smiled and turned to Drew, fixing his bonnett.
Drew was in tears, “Penny, p-please don’t make me do this!!”
“What?” Penny asked, feigning ignorance, “I thought you liked taking pictures?? You certainly had no problem doing it for those floozies you met on Kik! You even sent dirty pictures of you in diapers and dresses to men! So I'm sure this will be a walk in the park for you!”
“Honey, please!” Drew stomped his feet adamantly, “How many times do I have to tell you? I’m really sorry!”
Penny just smiled as she put the big bib around his neck that she embroidered with “On the Naughty List”.
“Oh don’t worry,” she said with a wink, “you will be.”
She straightened out his dress, ignoring his pathetic pleas while Amanda changed the curtain for the background.
“Alright,” she said, “I think I'm ready for you.”
Penny grinned again and immediately started arranging Drew into various poses.
“Criss-cross applesauce!”
“Now spread your legs so we can see your pissy pamper!”
“Hands and knees like you’re crawling. No not that way, turn around so your diaper is showing, then look back at the camera!”
Flash! Flash! Flash!
Drew’s eyes were watering, and not just from the lights stinging his retinas.
“Why don’t you suck your thumb?” She asked, but it wasn’t Penny, it was Amanda. She seemed to be coming around on the idea, getting more into it. Penny smiled like she’d just made a new friend.
Drew did nothing at first, like he wasn’t sure if he should take orders from Amanda. But Penny gave him an admonished look.
Not wanting to upset her further and have his humiliation intensified by receiving a spanking in front of the photographer, Drew reluctantly put his thumb in his mouth and started sucking.
Now that Amanda had control, she was putting him in all sorts of other positions, having him make faces, giving him props like rattles and blocks to hold and “play” with.
Flash! Flash! Flash!
“He looks pouty in all of these…” Amanda frowned at the screen on her camera. “Do we want him smiling?”
Penny shrugged, “I guess so. He has to look like he enjoys it right?” She said, then made a wall with her hand and whispered “which he definitely does” so only Amanda could see it.
Amanda giggled. Penny grabbed a stuffed bear from the prop bin and held it up behind the camera. She shook it back and forth so that the bells around the collar rang.
“Wook here wittle Drewbie!!” She called condescendingly, “smile for the camwwaa!!”
If anything, it only made Drew more moody. He crossed his arms and his little face turned red from being patronized.
“Awww!! What’s the matturr??” Penny cooed, stepping in front of the camera and putting her hands on her knees. “Is somewon upset?? You need Mommy to make it better??”
Penny reached between Drew’s legs and gently squeezed his squishy diaper. She immediately felt his little dick spring to attention. Before she knew it there was a little tent growing. Penny ran her fingers over it ever so gently, watching the pleasure and desire for release wash over him.
“If you be a good girl, Mommy will let you make cummies. Only good girls get to cum in their diapers, understand??”
Drew nodded frivolously, biting his bottom lip and lifting his hips in an attempt to follow Penny’s retreating hand.
Penny smiled victoriously. “That’s what I thought!” She said, standing and walking back behind the camera. She picked up the bear again, “alright, now…let’s see some smiles!!”
******
“Bounce baby! Bounce!”
Drew was revolted as he plopped up and down on his dirty diaper. Penny must have slipped something in that bottle. He tried to maintain a smile, but he was still blushing from having to do a ‘squatty potty” into his pampers in front of Amanda. Her nose was still turned up at the smell, but she seemed satisfied with the pictures she was getting of Drew’s mushy tushy.
“I think I've gotten just about all I can get,” Amanda announced. “But you still have 20 shots left…”
Penny smiled, looking at the bear again.
“I think somewon’s earned a chance to make a number 3 in their diaper…” she said, stepping forward. Penny could see Drew’s ears perk up, even beneath his bonnett.
As she leaned over, Drew involuntarily stuck his hips out, giving her free access to the crotch of his diaper, which was already pointy in the front again.
Penny giggled, tickling the front just to get him breathy and antsy. Her eyes were watering from the smell, but she kept her poise and handed him the bear.
“Here you go, sweetie!” She said, standing back up and walking behind the camera once more.
Drew looked perplexed, like she’d just handed him a Rubik’s cube. He had no idea what he was supposed to do with it. He looked back at Penny.
Flash!
“Sorry,” Amanda chuckled, “I just had to capture that dumbfounded look on his face.”
The girls both laughed, but finally Penny controlled herself, “Awww! Do I need to spell it out for your dumb wittle baby bwain?” She teased, “you’re gonna take Mr. Teddy,, and you’re going to rub against him like you used to do with Mommy. Before you went off to be a wittle snooty sending nudies!”
Drew’s bottom lip quivered. He didn’t want to subject himself to any more humiliation, and he certainly didn’t want it to be documented. But he also didn’t want to pass up his first chance at cumming in a long while.
He put the bear between his legs, pinched them together, pressed it into his dirty diaper, and started gyrating his hips.
Flash!
He managed to wriggle his cock into the right spot so he could at least get some stimulation. He had to press the bear in harder to feel anything through both types of padding.
Flash!
He humped harder. So hard the stupid bells around its neck started jingling, the girls’ laughter rang too.
Flash! Flash!
“Aww!! Look at his wittle face!!”
Drew was grunting now. He figured out that the best method was to put the bear on the floor and drive his hips into it. His diaper felt cold and icky, but he was too horny for it to stop him.
Flash!
He was getting close. The girls must have sensed it too.
“Tell us what you’re about to do in your diaper, sweetheart!” Penny called.
“I’m gonna cum!!” Drew cried. He pressed on, despite how much he cringed at how pathetic his voice pitched. Apparently it wasn’t pathetic enough though.
“Is that how we’re supposed to talk?”
“I’m gonna make cummies in my diapurr” Drew corrected, “I’m gonna make cummmies in my diapurrrr!!!”
Flash! Flash! Flash!
Drew spasmed on the floor, feeling a renewed, gooey warmth spread into his diaper. The relief washed over him. He sat up for the first time, and smiled.
Flash!
******
“Not her, please not her!”
Drew found himself saying that to almost everyone Penny suggested.
He’d just scribbled down the name and address for three of his friends from college, now she had him writing out the name of one of his ex-girlfriends.
“Let’s be honest, I'm sure she had her suspicions about you being a pampered, panty sissy. I did since about 2 months into our relationship. Did you ask her to peg you too?”
Drew’s tears blotted the envelope as he wrote out the names and addresses of all his friends, coworkers, acquaintances, and extended family. The slightest hesitation resulted in another week added to his chastity sentence.
The taste of envelope adhesive lingered on his tongue, but not as much as Penny’s new boyfriend’s cum did last night. Drew was thankful she didn’t include those pictures into the collage of other photos that were taken by Amanda.
He glanced at the Christmas card again as it was stuffed in the envelope. “Baby Drew’s First Christmas” it read, followed by a short description Penny made him write about how much he’s longed to dress like a baby girl and use his diapers. There was also a link to more photos written in red and green font.
“Last one,” Penny said, handing him the final envelope. Drew was relieved, until he turned it over to find the address she’d already written out for him.
The color drained from his face, a fresh batch of tears ran down his cheeks.
“No! Please! NO!” Drew cried. “Not my parents! I can’t! They’ll kill me!”
Penny placed a consoling hand on Drew’s skirt, as if that would make him feel any better. “Shhh dear, it’s okay. They need to know. This is who you are. This is what you’ve always wanted!”
“But they’ll never understand!” Drew exclaimed, “they’re super conservative! They go to church every Sunday! They’ll kill me!”
“Of course they won’t, honey.” Penny cooed, “you’re their baby boy! Now you just have to let them know you want to be a baby girl…”
Drew was distraught, his hands were shaking, so he decided to throw down the pen and cross his arms to keep them still.
“Are you gonna throw a tantrum?” Penny asked, crooking an eyebrow, “Do I need to add a week to your sentence?”
“You can add a whole year as far as I’m concerned,” Drew said as firmly as he could muster, “I’m not doing it.”
Penny just smiled. “Fine. A year it is.” She said simply, gathering up the envelopes so she could drop them off at the Post Office.
On her way out the door, she turned back to make one more snide comment, “I’m sure your sisters will definitely keep this a secret.”
THE END.
Happy Holidays, Everyone!!