Jeffrey's Adventures in Babysitting

Jeffrey's Adventures in Babysitting 1

By David

The author prefers not to display any email address. Please direct any feedback to [email protected] and it will be forwarded

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This story is intended for ADULTS ONLY. It contains explicit depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Jeffrey’s Adventures in Babysitting
by David

Chapter One – Friday Afternoon Delight

“Hello? Anybody home? It’s me-eeeeee ….”

Judith Martin stepped into the foyer and shut the door behind her. It had been a long week at work and she was glad to be home. Life was tough for a single mother with so many mouths to feed. Not that it wasn’t anything she couldn’t handle, but after that argument with her supervisor and the confusion over the Stapleton account, she looked forward to being away from the office for the weekend.

“Helloooo,” she called again. “Girls, I’m hoooo-ooome ….”

The weary woman set her purse and briefcase on the hall table and paused. The house was unusually quiet, especially for a school day. She was typically greeted by the chaos of childish shouting and arguing and crying. Ever since Evie went off to college the younger girls always seemed to be fussing and fighting, usually over the silliest, most trivial things. But not today. Today her home was silent, peaceful … almost too quiet.

And then she remembered. Oh yes … she had a new babysitter. How could she have forgotten? A mischievous smile curled her lips. Things had been quite different ever since the recent adjustments in the household routine. Quite different, indeed. She couldn’t help but chuckle to herself as she thought about how much life had changed in the past few days. She wondered what delightful surprises awaited her this afternoon.

“Hello?” she repeated as she headed toward the living room. “Anybody home?”

A quick look around revealed … nothing. Which was disturbing. Usually there was something out of order, a half-filled snack bowl, an abandoned school bag … a discarded doll. But no, nothing was there that shouldn’t and everything else was in its proper place.

Hmmm … they could be in the family room. Or maybe, just maybe, they were on the patio or perhaps in the back yard.

“Anita? Rita? Tina?” Judith sang out the girls’ names as she kicked off her high heels and picked them up. “What’s going on, guys? You’re being awful quiiiii-eeeeet ….”

“Jeffrey?”

“In here, Mrs. Martin,” a soft voice called from the back of the house. “We’re doing our homework.”

Judith’s eyes went wide with amazement as she walked into the family room. She almost burst out laughing, but she managed somehow to maintain her composure and act as though everything was normal, just as it should be. It was a struggle to keep her emotions in check, but she sucked in a deep breath, let it out and then enjoyed the sight before her with little more than a smirk to betray her amusement.

Lying on a bright pink blanket in the middle of the floor was a naked boy reading a book. Flat on his belly, his feet crossed behind him and his pale, adolescent body exposed to anyone who cared to look, thirteen year old Jeffrey Walton presented a charming if not comical sight; the idea of a naked boy in the Martin house was funny enough, but Jeffrey looked just absurd laying there in his birthday suit with his oversized horn-rimmed glasses and a colorful children’s storybook in his hands.

Oh my God, just look at that fat little butt, Judith thought to herself. How cute is that?

Try as she might, she just could not take her eyes off Jeffrey’s bare bottom; it wasn’t every day she saw a naked boy’s derriere, especially one so round and plump. She shook her head, then focused her attention instead on the blushing boy’s bespectacled face.

Well, he’s not completely naked. At least he’s wearing his glasses.

“Hello, Jeffrey,” the pretty woman sang in a smug, flirtatious manner. “I hope I’m not interrupting anything.”

Jeffrey glanced upward, a sheepish grin frozen on his round face. The poor boy looked like he was about to die of embarrassment.

“Um, hello Mrs. Martin. No m-ma’am … we’re just, you know … doing some homework. Everything’s fine … I guess.”

“Okay, if you say so.” The smiling woman gave him a little wink. “I had to ask. I’m not quite used to all of this peace and quiet.”

“Yes ma’am. I can understand that.”

Judith looked down at the mortified boy with some sympathy. And with good reason. Flanking him on either side – and adding to his precarious predicament – were her twin daughters, eight year old Rita Ann and Tina May. At the moment they had their faces pressed against their new babysitter's bare shoulders, apparently reading – or pretending to read – from the book in his hands. The sight was both bizarre and endearing. Knowing what she did about “the terrible twosome,” she could not wait to hear how they ended up in such a cozy position.

“Hello girls,” she said sweetly. “What’s the matter? Aren’t you going to say something nice to your mother?”

“Shhhh, Mommy! We’re reading!” fussed Rita.

Tina repeated her sister’s retort. “Yeah, Mommy! Shhhh, we’re reading!”

Unlike the naked lad between them, the two giggling girls were fully dressed in their usual after school attire, matching short shorts, matching sleeveless t-shirts and, of course, matching socks and sneakers. In keeping with their “twinness” they each had their bright red hair up in identical pigtails and bows; if it wasn’t for the slightly varied spattering of freckles on their faces even their own mother would have trouble telling them apart.

Suppressing a giggle, Judith cleared her throat. “So, is this for real? Are my dutiful daughters actually doing their homework? Good God, Jeffrey, how on earth did you get them to be so quiet?”

The naked boy pushed his thick rimmed glasses up his nose and brushed his hair from over his eyes. His plump, cupid's bow lips formed a perfect “O,” giving him a sensual, almost feminine appearance. Judith sighed. If his hair was just a little bit longer and he took off those silly glasses, he’d look just like a girl.

Isn’t that funny, she thought to herself. Take away a boy’s clothes, you never know what you’re going to get. Who’d have thought this one would be so adorable?

Jeffrey squirmed under the pretty woman’s scrutiny. He stammered as he spoke, which only enhanced the charm of his predicament.

“Well, um, Mrs. Martin … I, um … I told the girls that we ... we couldn't play any more games until they got all their stuff done. I … I remembered what you ... you said yesterday about their homework and, well … you know … I thought that maybe I could help.”

“Well, I am certainly impressed, Jeffrey. I’ve never seen them quite so intrigued with their reading.” The smiling woman nodded toward a third red-headed girl sprawled out on the sofa. “You’ve even got this little troublemaker to settle down with a book. That’s practically a miracle as far as I’m concerned!”

Eleven year old Anita Martin peered over the textbook that hid her face and snickered. “Oh, Mom, don’t be so dramatic! And don’t give Jeffrey so much credit. It’s not like you’ve never seen us doing homework before. He didn’t do anything special. We would have gotten around to doing it eventually.”

“Oh, I’m sure you would … at the last minute as usual,” Judith said sarcastically. “No, as far as I’m concerned Jeffrey is a magician. I come home after a long week at the office and instead of a lot of screaming and yelling, I find my three lovely little ladies all quietly getting along, doing their homework and being so proper and polite. This is your dear old mom's dream come true!”

The girls all giggled to hear their mother sounding so silly. The naked boy reacted by biting his lip and looking away bashfully.

Judith didn’t say anything for a few minutes. Instead, she quietly took a seat on the sofa next to Anita and took in the idyllic scene before her. The curious woman watched with some amusement as the twins gradually moved closer, practically hugging Jeffrey’s unclothed body, perhaps a bit too close for some people’s comfort; but she shrugged it off with little concern. A flush of redness filled the helpless boy’s round cheeks and crimson splotches could be seen across his neck and chest; the poor thing was obviously embarrassed to be trapped in such an awkward position, though he made no attempt to move or run away.

Not that he could have escaped if he tried, not with those two clinging to him like a pair of curious monkeys, Judith thought with amusement. It’s not like he has anywhere to go, come to think about it. I wonder where the girls hid his clothes this time? The poor child … I can only imagine what’s going through his mind right now.

She suddenly cleared her throat, startling the naked boy before her.

“I hope my little brats didn’t give you too much grief this afternoon, Jeffrey,” she said teasingly. “You let them take advantage of you way too much. I just don’t know how you put up with them as well as you do.”

Jeffrey grunted as the two girls suddenly climbed on his back and made themselves at home, sitting on him as if this was something they did all the time.

“Giddyup, horsey Jeffrey!” Rita ordered. “Come on, we want another ride!”

Yeah, horsey Jeffrey!” cried Tina. “Show Mommy what a good horsey you are! Giddyup!”

The beleaguered boy grunted again. “Not now, please. You’re supposed to be good now that your mom is here, remember?”

“We want another ride!” Tina yelled with commanding authority. She gave Jeffrey’s plump bottom a slap. “Giddyup, horsey Jeffrey, giddyup!”

“Rita! Tina!” Judith repressed the urge to laugh at the absurd sight. “Get off Jeffrey! He is not your personal play toy!”

“Yes he is, Mommy!” Rita squealed happily. “He is our play toy! He’s a big ol’ teddy bear!”

“Yeah, Mommy!” echoed Tina. “A bare butt teddy bear!”

The pretty woman laughed. “Now I’m confused. First Jeffrey’s a horsey, then you say he’s a teddy bear. Which is it, girls? He can’t be both.”

“Sure he can, Mommy!” Rita insisted. “Jeffrey is our slave boy! He does whatever we want whenever we want it! Isn’t that right, Jeffrey?”

The Martin girls all burst out laughing, including Anita from her perch on the sofa. Even Judith had to chuckle, just a little bit. Noticing Jeffrey’s face was bright red, she wondered if that was from embarrassment or the strain of the girls on his back. Or perhaps a little bit of both.

“No girls, Jeffrey’s your babysitter, not your personal slave boy,” the pretty woman playfully scolded. “And if I heard him right, you’re supposed to be doing your reading. Do you want me to send him home? No? Then get down and get back to your reading!”

Jeffrey sighed with relief as his passengers slid off his naked body. “Thanks Mrs. Martin. Sometimes they … you know … can be a handful ... I guess.”

As the girls resumed their previous positions Judith smiled down at the handsome – no, make that ‘pretty’ – boy and felt her heart race with excitement. What a wonderfully odd situation this had become! The helpless youth looked so ridiculous, but yet so delightful lying nude between her red-headed twins. Most mothers would have been horrified to have a naked teenaged boy anywhere near their children, but she knew her girls were perfectly safe; if anyone was in danger, she mused, it was poor Jeffrey!

She started to make a comment to that effect, but then she noticed something interesting; a ping-pong paddle laid amidst the schoolbooks and papers scattered on the blanket. Well, that certainly raised an eyebrow. She scanned the room and spotted the other paddle on the sofa next to her oldest child.

A thought occurred to her and she returned her gaze to the bashful boy's bare bottom and let her eyes linger over the soft, vulnerable skin for a moment or so. How did she miss this the first time? But yes, there it was – a definite red glow emanating from the otherwise pale flesh. More than what would have been produced by Tina’s playful blow just a moment earlier. No, this was from something more … serious. How interesting. She glanced at the teenager’s guilt-ridden face and shook her head as a comical image formed in her mind.

“So, Jeffrey, what exactly did you have to do to get our little angels to act so well-behaved?” she asked innocently. For some reason she could not stop herself from looking at the poor boy’s inflamed butt. “It wasn’t anything too demanding, I hope.”

The anxious youth clumsily pushed his glasses up his nose again. It was obvious that he was as uncomfortable answering her questions as he was lying on his belly, but he seemed resigned to maintaining his awkward position.

“Um, well … not really, I … I don’t guess,” he said with a regretful smile on his face. “I … I promised them if they got their reading done we … um, we might play a ... a game of some sorts.”

Judith nodded. “Soooo … a game of some sorts, huh? You’re going to play ping pong? Is that why the paddles are out? I thought we lost all the balls.”

Jeffrey’s eyes went wide with fear and at the same time the girls all began giggling like little maniacs. Even Anita was laughing, so hard, in fact, that she fell off the sofa.

“What’s so funny?” Judith asked. “Did I say something funny? Is it because I said ‘balls’?”

The cacophony of giggles reignited, this time so loud as to be ridiculous. The bewildered woman bit her lip in an attempt to avoid joining in the silliness while Jeffrey pulled his book over his head to hide his shame; she noted with some amusement how he clenched his bottom cheeks together as if to protect himself.

“Sorry, Mommy,” Anita finally replied once she caught her breath. “You’re right. We couldn’t find our … balls.”

“It turned out Jeffrey had them!” Rita squeaked.

“Jeffrey had what? The balls?” Judith blinked. “Oh. Okay, I get it.”

There was another wave of giggles, not quite as long as the first. It took a moment, but the oldest sibling quickly regained her composure and continued.

“Yeah, we didn’t have any ping pong balls,” Anita said gleefully. “But we didn’t let that stop us from having our fun!”

“Oh?” Judith raised a curious eyebrow. She switched her gaze from Jeffrey's red bottom to his shiny blue eyes peering from behind his book. She had to grin, he looked so adorable. “What kind of fun?”

“The best kind of fun!” Tina said with a sudden shout. “We played wrestling smackdown!” The pigtailed child began giggling so hard she could barely speak.

“Wrestling smackdown?”

“Yeah, wrestling smackdown!” Rita cried out before going into similar hysterics. “We wrestled Jeffrey and he got his bottom smacked down!”

“Yeah!” yelled Tina. “Smacked down hard!”

Judith glanced at the red bottom before her and stifled a laugh. “Jeffrey got his bottom smacked? Oh, you’re teasing me!” Not surprisingly, the naked boy still had his face hidden beneath his book.

“Oh he got it, all right!” Anita said. She got off the sofa and picked up her paddle and swung it around with enthusiasm. “He got it hard!”

All three girls cackled like crazy, which triggered their mother to join in the merriment. The pretty woman’s imagination caught fire as she pictured poor Jeffrey in a tussle with her crazy daughters and the errant ping pong paddles. The image of this naked teenaged boy getting a paddling at the hands her trio of little imps was so absurd, she joined in her daughter’s merry laughter. It took her a couple of minutes to calm herself down enough so she could talk to her new babysitter and find out what all had been going on.

“It sure sounds like you’ve had your share of fun this afternoon, little mister,” the happy woman said with as much dignity as she could muster. “That must have been quite an experience.”

Jeffrey set aside the storybook and looked up. He then sighed and rolled his eyes.

“They’ve been acting like that all afternoon, Mrs. Martin. They were a little wild when they got home from school, so we … well, they … wanted to wrestle some and it kinda got out of hand.” He squirmed a bit, then reached back and rubbed his aching posterior. “They can be pretty mean sometimes.”

Judith smiled. “I can only imagine. Do you want me to put some ice on your bottom for you?”

“Ice … on my …? Um, no thank you. It was no big deal.” The embarrassed boy seemed eager to change the subject. “Anyway, they um … got tired after a while. That’s when … well, I told them if they behaved and did their homework we could play something else. You know, something … well, not so rough. I suggested a board game, but Rita and Tina insisted on playing hide and go seek.”

“Hide and seek, hmm? That sounds like fun.” Judith smiled to see the blushing boy pause for a moment and bite his lip.

“Yeah, well, I, um, was kinda hoping you’d get here before it got that far.”

“Oh, really? And why is that?” the curious woman asked. “What’s wrong with hide and go seek?”

“Because we made him promise to go outside and play it with us!” interjected Tina. “And he said he’d do it, too, Mommy! He said if we did our reading he’d go outside and play hide and seek with us! He said he’d do it, but now that you’re here he’s trying to get out of it!”

“Yeah, we wanna go outside and play hide and seek!” Rita squealed. “And you’re still gonna do it, ain’t you Jeffrey? You’re gonna do it, ain’t you?”

“Yeah, you gotta do it, Jeffrey!” Tina teased. “Just ‘cause Mommy is home doesn’t mean you get out of it! You promised, remember? Remember? Say you’ll do it! Say you will!”

“Say you’ll do it!” the twins sang sassily. “Say you will! Say you will!”

“Yeah, he’ll do it, all right,” Anita said with an evil giggle. “Mom will make him. Won’t you, Mom? Make Jeffrey play hide and seek outside with us before he leaves! He promised and you always say you’re supposed to keep your promises! Please make him do it, please? PUH-LEEEEEEEEASSSSSE???!!!”

Judith looked down at the naked lad and saw his eyes were wide with fearful anticipation. She obviously knew what he wanted her to say, but a mischievous streak had awakened within her, telling her to do just the opposite. The smiling woman felt a thrill sweep over her body – tinged with just a touch of guilt – as she nodded her head in acquiescence to her daughters’ demand. Her heart raced with excitement as she watched the nude teenager’s face go pale in reaction to her decision.

“Well, I don’t know. If that’s what Jeffrey said, I don’t know why he wouldn’t follow through on his word ….”

“Mrs. Martin … that’s not … quite what … I meant,” the young lad croaked. “I really don’t want to go outside. Not like this. Not without any clothes on!”

“Did you make a promise or didn’t you?”

“I mean, yes ma’am, I did … promise that. I guess. But I didn’t think I’d really have to … you know … do it. I figured by the time you got home ….”

“Then there you have it,” Judith said. “Really, Jeffrey, you can’t go back on your word now, can you? I mean, really, what kind of babysitter would you be if you lie to the little ones and break your promises? That’s no way to win their trust, is it?”

Jeffrey sighed and dropped his head. “No ma’am. I mean … I guess … I guess so ….”

“What would your mother say? Hmm?”

The teenager bit his lip and rolled his eyes. “She’d … um … she’d make me do it. I guess.”

“You’re damned right she would!” The pretty woman gave him a bright smile. “Really, Jeffrey, I don’t see what the problem is. You made a promise. And it’s just a silly game. What will it hurt to play it?”

“But … I’m … I can’t … go outside naked. What if somebody sees me?”

“Oh, nobody’s going to see you. Our back yard is pretty big and the nearest neighbor is too far away to bother looking. And if they do, so what? You’re on our property minding your own business. Let them look all they want. You’ll be too busy having fun with the girls! And lord knows they already know what you look like without your clothes.”

There was a long silence. The room was eerily quiet; not even the girls were making a sound, no giggling, no whispering … nothing.

“Sooooo … I guess … I guess … you’re gonna make me …?”

Judith raised an eyebrow and looked down at the naked lad with her most serious “Mom Face.” “I’m not making you do anything. You’re the one who is making you do this. You did that when you made your promise. Seriously, Jeffrey. Promises are important. You need to keep them. Even if they are a little … embarrassing … sometimes.”

There was another long silence.

“Okay. I mean, yes ma’am. I’ll do it.”

The pretty woman gave a pretty laugh. “Great! Then you will play hide and seek with the girls before you leave, won’t you? Outside, just as you promised, right?”

“Yes ma’am. Out … outside … like I … I promised.”

Jeffrey’s blue eyes glistened. Were those tears? Judith felt a not-so-guilty thrill as she realized just how horrible she’d made him feel. The poor thing was actually crying. How adorable!

“You know, Jeffrey, you’ll be doing me a great favor if you go out and play with the girls for a while. Lord knows they need the exercise.”

“Yes ma’am.”

Judith grinned. “Oh, don’t be so pouty about it. This is all your fault in the first place, you know. The girls love you! They always get so excited when you’re here, so you really need to help me wear them down. Otherwise they’ll be driving me crazy all night.”

The naked lad sighed and bit his lip. “But … my mom … she’s expecting me home. I gotta eat supper and … you know … stuff.”

The pretty woman was quick to wave off his protest. “Oh, don’t you worry your pretty little head about that. I’m sure your mother won’t mind if you’re running late. I’ll tell you what … I’ll give her a call and tell her you’re staying to eat with us! Then you and the girls can play outside for a while and I’ll order a pizza. After supper you can help me settle them down and then you can go home. How does that sound?”

The teenager wiped his eyes on his arm and nodded. Once again Judith raised her eyebrow and gave him her prettiest smile. “You’ll be doing me a big favor.”

Jeffrey bit his lip again. “I guess so. I mean, yes ma’am.”

“Wonderful! I'm so glad you see it my way. Now, you take the girls out to play ….”

“Now, Mrs. Martin?” The blushing boy gave her a pleading look. “I … I mean … now?”

Judith gave the naked boy a sharp look. “Yes, now, Jeffrey. As in … NOW. Do you have a problem with that?”

The contrite boy bit his lip. “No ma’am. I’m sorry.”

“Good. As long as we understand one another. Now, as I was saying before I was so rudely interrupted, you take the girls out to play and I’ll phone your mom. I’ll make the call for some pizza in about an hour or so, okay? Okay!”

There was a cheer from the girls and all three of them suddenly swarmed the nude lad, grabbing his hands and prompting him to get to his feet. It was as though they’d been holding their breath for the past several minutes, waiting to see what would happen next. Now that they knew, they wasted no time in playing catch up.

“Come on, Jeffrey, let’s go outside!” the twins shouted with cruel delight. “Let’s go play hide and seek! Come on, let’s go! Let’s go now!”

“Yeah, let’s go play some games,” Anita said with an evil laugh as she gathered up the ping pong paddles. “Let’s go have some fun!”

Judith watched with amusement as the naked youth awkwardly climbed to his feet, exposing the front of his body, his bare belly and, of course, his penis and ballsack. To everyone’s surprise – well, except for Jeffrey, most likely – his penis was erect; standing straight up, almost parallel to his body, the slender pink appendage bounced about like a happy puppy dog’s tail. Judith saw it and the three girls saw it, too, and they looked up at their mother, waiting for her reaction. She couldn’t help but grin at her daughters; to the chagrin of the helpless boy all four Martin females burst out simultaneously in raucous, rude laughter.

“Well, lookie there! It appears that someone is ready to have a good time!” Judith noted with pleasure the look of distress on young Jeffrey’s face. “Just be careful and don’t touch it, girls. It might go off on you!”

“EWWW!!!” Anita cried out in giggly disgust. “Mom, that’s gross!”

“Yeah, that’s gross, Mommy!” echoed the twins.

The gleeful woman laughed. “You’re right. Those things are gross! Now go on, get out of here! You children go have fun! And don’t do anything I wouldn’t do!”

And with that Jeffrey Walton was led by the three Martin girls out the patio door and toward the back yard. The look on the naked lad’s face was one of complete and utter defeat.

“Hmmm … what fun,” Judith said aloud as she kicked off her high heels. “I bet none of the women at the office come home to a greeting like this ….”

As she headed upstairs to change her clothes Judith could hear shrieking and laughter coming from the back yard. Smiling to herself, she imagined what it would be like to be young again.

“I wonder what Jeffrey’s doing tomorrow?” she wondered as pulled out her phone. “It is Saturday, after all, and I could use an extra pair of hands around the house. Ah yes … that sounds like a grand idea ….”

To be continued …?

(End of File)