College or Cribs

Chapter 7
The Date

Chapter Description: Looks like Sherry remembered their date, even if it's no longer exactly a romantic evening.

College or Cribs

Chapter 7: The Date

Chris’s eyes fairly bugged out of his head. Sherry, his Sherry, was the babysitter?! He peered out through the bars. Same light brown hair flowing past her shoulders, same perky breasts, same hips and the barest hint of a tummy. Same brown eyes and bright smile. That was his Sherry alright. She was just as hot as he remembered her, wearing a well-worn GAP t-shirt, jeans and sneakers. And here he was in nothing but a t-shirt and sitting in a dirty diaper while he sucked his thumb.

Wait…what?

Chris popped his thumb out his mouth; a string of drool still connecting his thumb and his lips. When the hell had that happened? The longer and longer this day went on, it seemed, the more of Chris’s body went on auto-pilot. Speaking of auto-pilot, Chris’s penis was starting to stand up and stiffen at the sight of his girlfriend as blood rushed from one head to the other.

“We don’t need a babysitter,” Samantha protested. “Bri and me can take care of ourselves!”

“Sherry isn’t here to baby-sit you, she’s here to babysit Chris,” Roxanne patiently replied.

“We can take care of Chris, too,” Samantha retorted. “He’s easy to take care of.” Brianna nodded her agreement.

“Oh really?” Roxanne asked, “Does that mean you want to be responsible for feeding him?”

“Did it this morning,” Sammy answered. Bri elbowed her big sister in the arm. “With Bri’s help,” she added.

“Putting him down to bed?” Roxanne asked.

“I can do that, too.” Sammy crossed her arms.

“Change his diapers?” Roxanne cocked a knowing eyebrow. Brianna quickly backpedaled and shook her head no. Samantha stood stone still, and bit her lip, her cheeks beginning to blush. She didn’t say anything. Roxanne just stood with a self-satisfied smirk that only a parent can have when they’ve maintained dominance over their children.

“It’s not that your mom and dad don’t trust you,” Sherry spoke up breaking the tension. “It’s just that both of you are too young to drive and she doesn’t want you two to have to be responsible in a crisis situation.” Sammy tilted her head to the side, waiting for more. “In the highly unlikely event,” Sherry stressed, “that something bad happens, I’ll be able to drive to the hospital or call 911 and present whoever they send with proper identification. It’s an insurance thing, Sammy, you understand.”

Sammy shrugged her shoulders, and nodded. Apparently she did understand. She turned around to go back to her books.

“Can we have a hug before you go back to doing what you were doing?” Roxanne called out. Sammy turned around and gave each of her parents a hug before about facing once more.

“Bri, you too.” Doctor Cole said in a low reserved voice that brooked no argument. Brianna trudged over and gave each of her parents a bear hug. Doctor Cole let out and animated groan from the pressure, while Roxanne grunted a little bit in earnest.

“Our cell phone numbers are on the fridge and so is some pizza money for you and the girls.” Roxanne rattled off, “and Chris’s baby food is in the pantry. It’s the start of summer break so we don’t mind if the girls stay up late, but try and have Chris in bed by 8:00. He had a good bath yesterday and didn’t get too dirty, so you should be good as far as that’s concerned.”

Sherry nodded, as she walked over to the giant playpen where Chris was. Once again the pen mysteriously opened as she walked in, Chris still couldn’t tell where the latch was or where the gate was located. For all Chris could tell, Sherry might have walked in a different side of the playpen than Bri originally had.

Effortlessly, Sherry scooped her boyfriend up by the armpits, and Chris felt like he was sailing through the air till he found himself positioned easily on Sherry’s hip. One hand supported his back, while her other hand was under his bum, spreading the poop in his diaper around even more. While this had been too much to bear earlier in the day, Chris couldn’t help but feel aroused by this, and his penis became fully erect and hard. He resisted the urge to start dry humping Sherry right then and there.

Sherry carried Chris over to the door where his parents were waiting. His dad tousled Chris’s hair and said “Bye-bye champ. See you tomorrow,” and then gave an odd wink to his son…the kind of wink typically reserved for an older Chris going out on a date with Sherry. Then again, dad always was a card and a bit of a flirt and horn dog. Who’s to say Dr. Cole didn’t give similar “knock ‘em dead, killer” looks to an infant Chris when left with a babysitter the first time around.

“Be good for Sherry, sweetie,” Roxanne said, “Mommy loves you,” Roxanne leaned over and gave an exaggerated “mmmmwah” kiss right on Chris’s cheek. Simultaneously, Sherry did the same thing to Chris’s other cheek and Chris found himself sandwiched in the middle of two of the most beautiful women he had ever met. Chris’s whole body was a tingle. He shuddered involuntarily and squeezed Sherry’s midsection with his thighs.

If Sherry’s body hadn’t been blocking his own crotch, he would have been rubbing himself right now. Suffice it to say, the oversized Pamper was feeling a lot smaller at this moment in time. The second his parents were out the door, Chris’s hormonal instincts kicked in and he found himself groping his girlfriend’s chest. He instantly felt the soft padding of her bra and squeezed, feeling the firmness of her breasts, smaller than Roxanne’s but firmer. Maybe he was flattering himself, but he swore he felt her nipple harden as he grasped at her.

Sherry took her hand off of Chris’s back and gently removed his hand. Without looking at him she said “Uh-uh, I’m not mommy.”

“Oh, but you are!” a horny adult-babied Chris exclaimed, knowing it would only come out as gibberish to her. He then copped himself another feel, only to have his hand quickly removed, then blocked when he tried a third time.

“Boys,” Sherry muttered to herself as she shook her head softly, “they all want the same thing at any age.” Chris was about to attempt grope number 4, when he found himself hoisted up slightly, now being forced to lean over Sherry’s shoulder. He felt a slight gust of air on the crack of his ass as Sherry pulled back the waistband of his diaper and looked down inside. His girlfriend was checking his diaper and finding it poopy! How many of his masturbation fantasies had started off like this? A lot, that’s how many!

“Thought so…” Sherry said to herself, “Bri? Sammy?” she called out. “Would one of you mind calling Dominoes while I change Chris?”

“Okiedokiefinokie,” Chris’s youngest sister called out, headed towards the kitchen, cordless phone snapped up in hand along the way.

Chris found himself being carried toward what was now his nursery, a low moan escaping his lips as they crossed the threshold.

“I know, I know” Sherry cooed.

“You honestly have no idea, Sherry.” Chris whispered back through clenched teeth. He was so hard right now, but was on that threshold between sexual frustration and sexual elation. The point between being aroused and making your move or just giving up and feeling a sense of disappointment and disturbance as your stiffy became a softie.

He began to drool slightly as Sherry laid him down on the changing table- his changing table- and pulled the stomach strap across him so she could change his diaper-his poopy, poopy diaper. He almost couldn’t stand it. Any guilt he had felt this morning when Roxanne was changing him had completely disappeared. It was one thing to be aroused by your father’s wife, but your own girlfriend was completely fair game in the sexual fantasy department. Chris balled up his fists and brought them to his chest while he splayed his legs out and bent his knees a little, practically putting his diaper on display. His posture resembled a dog begging to have its tummy rubbed as much as a toddler ready to be changed.

The floorboards squeaked as an intruder entered the room. “Hey Sherry,” Samantha interrupted her big baby brother’s reverie. “Just making sure, thin crust pepperoni okay?”

“That’s fine,” Sherry nodded, as she bent over and grabbed baby wipes, baby powder, and a fresh diaper from underneath the table.

“Yeah, it’s fine, Sammy, see you later,” Chris called out hoping his little sister would leave the room before the good part started. But Sammy didn’t move. She just eyed Chris on the changing table, then looked to Sherry, then back to Chris, then back to Sherry again. She was waiting for something.

“Can I help?” Sammy blurted out. Chris and Sherry both answered at the exact same time. Unfortunately Sherry’s “Sure,” more than countered Chris’s “NO!” which probably sounded to their ears like “GAH!” Chris’s eyes widened as he realized he was about to be part of a demonstration for his little sister. She was going to be able to see his…his…he couldn’t even finish the thought.

“First thing’s first,” Sherry said, handing the diapering supplies over to Samantha. “I know he’s got a poopy diaper, but I don’t know if he’s wet it or not. This is super important for boys because they might accidentally pee on you in the middle of the change. So I like to even my odds by checking to see if they’re out of ammo.” Sammy listened intently. Chris just blushed. He sought comfort in the only way available to him. He started gently sucking his thumb to hide his embarrassment.

“Now, the stuff in diapers make them swell up like a sponge after they’ve been peed in,” Sherry went on, “so an easy way to check is to squeeze the front of their diaper and see if it squishes or crinkles. If it crinkles in the front, it’s dry, if it squishes its wet.” Chris bucked slightly as Sherry squeezed the front of his diaper, rubbing up against her hand. That wasn’t intentional, Chris swore…but he couldn’t help himself. If his erection had any chance of going away before, it had just lost that chance; little sister or not. Chris sucked a little harder on his thumb and blushed a little more.

“Another easy way to check is to stick two fingers in the leggings of the diaper and feel around a little.” Chris eeped a little as his girlfriend demonstrated the proper technique. The warmth of her hand so near his cock made him moan a little bit. His eyes looked towards his sister who was watching intently, making notes in her head like he took notes during college lectures. He felt so ashamed but couldn’t stop himself.

“It looks like he’s dry right now,” Sherry announced, “but we’re not out of the woods yet. A lot of babies prefer to poop in otherwise clean diapers. I can’t tell you how many times my mom changed my little brother’s wet diaper only to have him poop as soon as he was in a clean diaper-“

“-And vice versa?” Sammy finished the thought.

“Yup,” Sherry nodded. “And a lot of times, the feeling of fresh air hitting a boy’s penis will make him pee. So we’re gonna take some precautions. Okay?”

“Kay kay,” Sammy agreed.

“Here’s a trick my mom taught me for changing diapers,” Sherry said as she lifted Chris’s legs and still-diapered bum in the air. “Unfold that fresh diaper and slide it under.” While Sammy could have no doubt single handedly unfold a normal diaper, she had to put down the box of wipes and baby powder on the floor as she clumsily unfolded the oversized diaper and slid it under Chris’s bottom. Her nose wrinkled slightly from the smell as she got closer to the business end of Chris’s Pampers. Sherry glanced over and inspected Sammy’s work.

“You slid it in backwards,” Sherry giggled as she rotated the unfolded diaper around. “See the little tapes?” she pointed, “they’re the back of the diaper.” She finally eased Chris’s still dirty-diaper clad bottom down onto the new one. She quickly reached down between Chris’s legs and pulled the diaper up between them. “The part with Big Bird on it is the front of the diaper”, Sherry lectured, “it’s also kind of the target zone for where the tapes go.” Chris’s brow furrowed in distress. Were they going to double diaper him instead of changing him? A cocked eyebrow from Samantha seemed to ask the same thing. Sherry pulled the front of the diaper back down.

“Now that we’ve got the new diaper under him and ready to go, if he starts peeing, all we have to do is reach up and close the diaper. Got it?” Sherry asked. Sammy just nodded as she picked the box of baby wipes back up.

“Now we’ve got our setup, time for the icky part.” Sherry announced, as she un-taped the sides of Chris’s soiled diaper. She pulled the front of soiled diaper back and Chris once again found himself ass up in the air with his feet pointed towards the ceiling. “You can get a lot of the bulk out of the way by using the inside front of the old diaper,” Sherry instructed, and demonstrated. Chris eyes bulged as he felt the poop being wiped off him, his erection still not flagging even as he was naked in front of someone who’d had no business seeing him that way. Chris sucked his thumb even harder, building up a steady rhythm to soothe himself.

“Then you use the wipes,” Sherry said. Sammy looked a little surprised herself. “I mean the general ‘you’, sheesh” Sherry smirked, “You just hold the box and I’ll do the real dirty work.” Chris felt completely helpless as his butt was wiped by his girlfriend. He tried to close his eyes but each cold wipe to his cheeks only made his eyes pop back open. He could feel Sherry’s tender hands with each stroke. Chris feared he might suck out his thumbnail if this didn’t stop soon. His whole body was blushing red from embarrassment. Then it got worse.

“Um..” Sammy said, pointing with her eyes, “should we be worried, about…that?”

“What?” Sherry asked, still wiping her boyfriend’s bottom. Then her eyes followed Sammy’s to Chris’s bulging erection. “You mean his little pee-pee? Oh that’s no big deal.” Chris wanted to crawl into a hole and die right there. “That just means he likes this, don’t ya buddy?” she addressed Chris. “He doesn’t really know what it means. He can’t help it.” Tears started to form up in Chris’s eyes. Well, she was half right, anyways.

Never once did either girl take their eyes off of his nakedness. It was just too intense, too humiliating. Then he felt a cold wipe probe his groin, cock and balls. Chris practically screamed into his thumb. Even with the equivalent of a cold washcloth being dragged across his privates he couldn’t stop the rush of blood to his genitals, knowing that Sherry’s hand was less than a millimeter behind the wipe.

“Then you just ball the old diaper up, and use the tapes to keep it closed” Sherry continued her lesson, “and toss it away.” Sammy shrieked and dropped the wipes as a dirty diaper came flying into her arms. “Just throw it away. We’ll both wash our hands after this.” Sammy frantically complied and placed the soiled thing in the diaper genie next to the changing table. “Now hand me the baby powder.”

“This next part is optional but it helps with chafing and makes the baby smell better,” Sherry explained, “practically a must after a poopy diaper change.” With that Sherry liberally applied the powder to his diaper area and smoothed it with her hand, including a firm grab of his penis. Oh god. Chris could no longer breathe through his nose, and swore he could feel his pulse throb through his cock. “Then it’s just a matter of pulling the front of the diaper up between his legs,” she did so, “and taping it on.” Finally. Chris was practically hyperventilating now.

Out of nowhere, Sherry gave his padded crotch a firm pat and declared that he was “all done.” That did it. That was all it took. Chris writhed on the padded table, as hot cum erupted from his penis and spilled into the front of his new diaper. It came in short spasms and spurts, and Chris felt a glow of relief wash over him, followed immediately by a wash of guilt. Ewww…ewwww…what kind of freak was he? Almost immediately, his dick began to soften and become flaccid. He took his thumb out of his mouth now that it was over.

“Why is he squirming like that?” Samantha asked, obviously having noticed Chris’s orgasm.

“Oh he’s probably just a little antsy.” Sherry concluded, “it’s usually doesn’t take this long to change him, but I deliberately slowed down so I could show you.” Deflated, defeated, and mortified beyond belief, Chris went limp (in more ways than one) and allowed himself to be carried by Sherry out of the nursery and into the kitchen. He was barely aware of being strapped into his highchair and the feed tray being clicked into place.

Chris was absolutely lost in a labyrinth of thought as Sherry fed him spoonful after spoonful of pureed peas and mashed bananas. A line had been crossed in Chris’s mind, and he wasn’t sure if he liked it. Sure, he liked it; but he wasn’t sure if he liked that he liked it. There was definitely something sexual about his fetish, but the fact that it wasn’t at all sexual for the other participant, namely his girlfriend made him feel less like he had had a sexual encounter and more like he had just…well…jazzed in his pants. Damn, there was something wrong with him. The fact that Sammy, his kid sister, had watched the entire ordeal with rapt attention made him feel even worse.

Chris accepted the bottle of baby formula from Sherry’s outstretched hands, and suckled without comment. The creamy over sweet stuff rolled down his throat, and gave him enough of a sensation that he was at least able to get out of his own head for a minute. Sherry’s hands disappeared underneath the tray of the highchair and his pulse quickened as she slipped two fingers into his diaper. Damn his libido.

“Dry enough,” she declared. In short order, Chris found his mouth being wiped, the tray being removed, and him being taken out of his high chair and into Sherry’s arms. Some firm pats on his back made him belch involuntarily as Sherry paced with him on the kitchen’s linoleum floor. “That’s a good boy,” she praised after each burp. He was spent; done and didn’t even bother to look up as the new stimulus of a doorbell ringing intruded on him, followed immediately by calls of “I’ll get it,” from the girls.

“Thank you!” Sherry waved at the pizza delivery guy while Bri and Sammy in short order ran to the door, snatched the pizza out of the guy’s hands, smacked a fistful of cash down in his palm and then slammed the door shut.

“You guys wanna watch a movie on Netflix?” Sherry asked, toting her boyfriend over to the couch. Both children nodded enthusiastically as they put a box of pizza right on the coffee table and proceeded to dig in, no plates no napkins, no nothing.

Soon enough, Chris was sitting in Sherry’s lap, being cuddled on the couch while they all watched a PG-13 movie about children fighting to the death in a futuristic dystopia. “Hey, it’s Summer, and I won’t tell if you won’t,” Sherry made a promise to the elementary-schoolers.

“What ‘bout Chris?” Bri grunted the question.

“Oh he definitely won’t tell.” Sherry said not missing a beat. They all had a decent chuckle at that. Chris for his part felt too worn out and defeated to object or feel offended or much of anything other than vulnerable.

He eased into Sherry’s soft body, and she coddled him with one arm while gingerly eating pizza with the other. He turned his head to the side, watching the movie out of the corner of his eye while he used her breasts as a sort of pillow. This was a strange delight, he admitted to himself. Normally, she’d be leaning into him, and if anything she’d be in his lap. He’d be the big strong man protecting her from the world.

The sudden role reversal gave him a strange amount of comfort and security. He squirmed slightly to adjust from time to time, but Sherry didn’t seem to mind it. Maybe protection was something everybody wanted.

Then something caught Chris’s eye. Bri, her usual animated and greedy self, had taken the last, biggest piece of pizza out of the box; its contents overflowing with the cheese and grease of its departed brethren.

“I’m a baby bird.” She remarked as she tilted her head back, mouth opened wide and attempted to lower the piece of pizza down into her mouth like it was Boba Fett and she a Sarlacc pit. Plop! The cheese slid right off and now Briana’s face was coated with the stuff. She looked like Pizza the Hutt.

“Arg!” She yelled in frustration and embarrassment, wiping the cheese and pepperoni from her face and manically throwing it back into the box, a barren slice of bread and tomato sauce all that was left. “Tewey! Puh-tewey!” she cartoon emphasized each spit as she ran to the kitchen to get a napkin to wipe her face.

Chris giggled. Then he chuckled. Then he chortled. Then his body was shaking with laughter at the sight of his youngest sister, covered in meat and cheese and sauce. “I’m a less messy eater than you, Bri!” Chris called out as her footsteps echoed back from the kitchen.

Bri took it all in stride as she sat down next to Sherry, and gingerly, without much resistance from Sherry, pulled her brother into her lap. “So, you like laughing do ya?” Brianna whisper-growled.

Chris’s eyes widened. “Uh-oh,” he gulped.

“WELL WHO’S LAUGHING NOW?!” She maniacally yelled as she dug her pudgy talons into Chris’s ribs and began tickling him mercilessly. Chris shrieked with laughter as he futilely struggled against his now big sister’s onslaught. He grabbed her wrists and tried to pull them away from him as he laughed, but they might as well have been made of dwarf star matter for all the good he was doing.

He spazzed and writhed trying to get free, his head falling into Sherry’s lap while he was still being tortured.

“Help…me…” he gasped in between torturous guffaws. Sherry only chuckled and politely covered her mouth. “Help…me…” he begged, clenching his jaw. “HelpmebeforeI….I….” too late. Chris felt the splish splash of urine erupt out of him as he involuntarily flooded his diaper. His crotch became wet and warm and the diaper was quickly swelling up. Tears came to his eyes.

“Uh…oh”. Bri pronounced, stopping her tickling. Gross. She had felt it too. It made sense, he had been sitting in her lap.

“Lemme check,” Sherry blithely said as she patted Chris’s padded crotch. “Yup….wet.” Chris’s blush returned full force. He couldn’t even keep his pants dry when being tickled. He felt so helpless, so limited, so incompetent…so…babyish.

“I can change him!” Sammy piped up with a little too much excitement. Chris’s hands immediately shot down to his crotch. No way. Uh-uh. He shook his head emphatically. Not again.

“That’s alright,” Sherry said, as she scooped Chris up out of a horrified Bri’s lap. “I’ve got him. I think it’s about bedtime for him anyways.” Bri for her part had stopped tickling and had thrown her hands up into the air the moment Chris had wet himself, as if trying to distance herself as much as possible.

Chris found his thumb on autopilot going towards his mouth as he was carried

back to the nursery and laid down on his changing table. There was almost no sensuality in Chris’s mind as Sherry wiped and re-diapered him, this time into a much thicker night-time diaper. Now the Sesame Street characters on his crotch were all wearing pajamas and night caps and his legs were splayed even further apart than usual.

“Night-night, Chris.” Sherry whispered as she lowered Chris into the crib. His crib, he thought, suddenly rather grimly. She handed him the stuffed bear at the foot of the bed. “Here’s your Wubby to keep you company.” She kissed him on the forehead, and walked out of the nursery, closing the door behind her.

Chris, suddenly in a dour mood at tonight’s turn of events, glared at his teddy bear. Wubby, for his part, stared back, a slight smile stitched on his lips. “Hmmph,” Chris muttered, “too much dumb baby stuff. I didn’t even get any pizza.” In a tired tantrum, Chris threw his old childhood toy over the railing and out of the crib, before turning his head in the other direction and shutting his eyes.

In the darkness, Wubby’s black eyes suddenly became a mismatched pair of gems- one red and one blue. As sleep claimed Chris, the gems twinkled a bit.