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Babysitting Benny - Chapter 4

Chapter 4

On Friday, right after school, Holly received a phone call. It was Mr. Gregson asking if she was free to babysit for the entire weekend while he and his wife attended a wedding out of state. Holly was dumbfounded. The Gregsons hadn't called in months. What could have prompted them to all-of-a-sudden ask her back? Of course, if anyone knew of Benny's power of persuasion, it was her.

She didn't detect any hesitation in Mr. Gregson's voice, so she told him she'd love to and she'd be there at six thirty.

Mrs. Gregson answered the door when she arrived and was smiling broadly.

“Come in Holly! My goodness, it's been a long time. I was so relieved you could do this for us. I know how busy you've been with school and really, we hated to have to ask, but Amy's got the flu and couldn't make it.” she explained.

“Oh, not a problem. I already wrote exams, so I'm not that busy at the moment. I'm happy to help and you know I love the kids.” She tried not to blush as she said this.

“And they love you too. Benny's been begging us to call you for ages. He misses his favourite babysitter.” Mrs. Gregson laughed.

“Hello Holly,” Mr. Gregson appeared from around the kitchen doorway.

“Hi Mr. Gregson,” Holly answered with a slight bow of her head, sensing the undertone in his voice.

“Well, I think we better get a move on, only a couple hours of daylight left. Holly, you know where everything is – emergency numbers on the fridge and the number where we're staying as well. Call anytime.” he informed her.

Just then, Benny entered the room, carrying his baby brother, Josh.


“Hey Ben. Look who's back!” Holly teased him.

“Cool. And you're staying all weekend, right?” he was exhilarated.

“Yep. You're going to be sick of me by Sunday.” Somehow, Holly doubted this.

“Ok kids, we're outta here. Ben, you behave now. Look after your brother, don't make Holly do all the work. We'll see you guys Sunday night. Love you, kiddo,” The Gregsons each bowed down and gave Ben and Josh kisses and hugs.

“Bye Mom, bye Dad, love you too.” Benny returned.

They watched the car pull out of the driveway and drive out of sight down the street.

“Oh my God, can you believe it, Holly? The WHOLE weekend!” Ben squealed.

“Take it easy. We still have Joshy to think about. But I know, I never imagined this happening, ever. I'm so happy you got them to have me back.” Holly replied.

“How do you know it was me?” Benny asked in the most innocent voice he could muster.

They both just looked at each other and Holly rolled her eyes and laughed.

For the next couple hours, the kids busied themselves by taking Josh for a walk in his stroller, cooking spaghetti and watching cartoons. Holly bathed the baby and around 8:45, had finally sang him to sleep and placed him in his crib. She crept quietly out of his nursery and closed the door. She could already feel the butterflies in her stomach, knowing that her night was just about to get started.

When she reached the bottom of the stairs, she could hear moaning coming from the living room. Bewildered, she took the last few steps until she saw where the noise was coming from. The television. It was the porno from the last night she was here. Benny had put it in the player and was now laying back on the couch, naked, slowly stroking his boner.


“What? I was horny.” he explained, matter-of-factly.

“I just didn't expect it, I guess.” Holly gave a little laugh.

“Do you want to suck me?” My God, he's so brazen about this now! Holly still couldn't get over how adult-like Benny was becoming, so bold and confident with his maturing sexuality. And the kid had no shame.

“MmHmm, I do,” She began stripping off her clothes, not wanting to waste even a second. Holly stood directly in front of Ben and unsnapped her bra, pulling it off her shoulders and releasing her bouncing B cups. Her perky little nipples pointed right at him. Next, she unzipped her shorts and slid them over her well-developed hips and let them fall in a bunch to the floor. She played with the elastic at the top of her panties, teasing Benny a little as he continued to jerk on his stiff, pink cock. Finally, not being able to stand it anymore, she pulled them off and knelt between the boy's legs.

“Look, it's wet at the top.” Ben moved his hand away to reveal to her the shining, slick head of his dick.

She bent down and licked the sticky stream of precum, savoring it and going back for more. Benny sighed and laid his head back on the couch cushion. Holly kissed and licked and teased his prick until it was as hard as it could ever be. She eventually covered it entirely with her mouth, sucking and pulling with her lips and tongue. She fondled his hairless balls with her fingers and he occasionally would rear up and hump into her face, so lost in the intensity of his building orgasm.

He knew he was very close to cumming, so he leaned up just a bit and watched her work her sloppy little mouth over him. He reached out both hands and twisted her nipples and she kept sucking. Sucking faster and faster now, he was so close. Just on the verge, he pulled his cock out and held it out, aimed at her face and told her to open her mouth. Holly did, and just in time for both of them to watch the pale white jets of spunk squirt out of him. It hit her in spurts, some on her cheek, some across the bridge of her nose and some even shooting right into the back of her throat. Finally, when he was spent, he released his tight grasp on his dick and relaxed. He then giggled at the sight of Holly, her face covered in splashes of his juice.

Holly stood up and crossed the room to grab a baby wipe and clean her face. Satisfied that she had given Benny a decent blow job, she now wanted her turn. She was feeling especially confident tonight, given that they were all alone and would remain so. Since Ben wasn't very hard just yet, she would have to give him a little incentive to fatten that dick up again, so he could give her the fucking she deserved.

On her way back to the couch, she bent and grabbed the sides of the coffee table, dragging it over with her. She placed it in front of the boy and walked to the end nearest him. Holly sat on the edge and began to tweak her nipples for him. She squeezed her boobs one by one then pushed them together, jiggled them a bit. Ben was speechless, rapt, mesmerized by the show, his penis already coming back to life. Holly continued to toy with him. She leaned ahead just a touch, offering a soft, supple nipple and pulling away. She pinched them and brushed her thumbs over them, letting them bounce back into place. They were becoming blushed and fat and begged for a warm, wet set of lips to latch on, but Holly resisted the urge to give in and let Benny suckle just yet.

She leaned back and lay prone on the table, placing her feet on either side and parting her thighs. Her trim, young pussy was visibly moist. The sweet, succulent lips protruding just a bit and her firm, erect clitoris beckoned to Ben. Holly slowly slid her palm down the length of her torso and rested it on her mound. She rubbed it provocatively and spread it open to him with her fingers. Ben was licking his lips and gently juggling his balls.

Holly brought her hand up to her mouth and wet her fingers. This time, when she reached between her legs, she inserted a finger and began to fuck herself with it. Her thumb stroked her clit as she pumped one, then two fingers into her wetness. The sights and sounds were driving Benny wild. He wasn't even touching his penis but it was twitching, yearning to replace those fingers. Holly's moaning was increasing, matching the speed of her bottom, which was grinding into the coffee table. The juice was lightly trickling out of her, rolling into her crack.

Ben simply didn't have it in him to let that sweet nectar go to waste. He jumped up from the sofa, knelt and bent over the table's edge and thrust his tongue inside the girl. Her entire body shook at this entry.

Ben held her thighs down and lapped at her perfect, delectable cunt. He licked her inside and out, his mouth venturing between the cheeks of her round, pliable ass, devouring the flavours of her. His tongue flickered all the way back up and his lips closed around her pointing clit. He pulled hard on it, stretching it away from her body and releasing it. With every slurping motion, Holly shuddered and groaned.

“Oh my fucking God, yes! Don't stop doing that, I'm gonna cum!” she declared.

Sensing the coming rush, Ben sucked and sucked and when she was right on the edge, he wedged three fingers inside her and felt the outpouring of heat and moisture and the rhythmic vibrations of her climax on his face. Her hips came all the way off the table and Holly rode the waves of pleasure, clamping down on Benny's fingers and mashing her groin into his mouth until she came back down to earth.

While Holly lay there, basking in the glow of her orgasm, Ben moved his body up and onto hers. His cock pressed firmly against her stomach, he latched onto her swollen left nipple and kneaded the other in his hand. Holly was so overcome with sensation, she swayed beneath him. She dragged her fingers through his hair and held him to her breast.

When the time felt right, Ben wiggled his body into position, still clamped to her chest and aimed his erection at her opening. She spread her legs wider, raised her feet into the air and awaited his penetration. The inside walls of her vagina were already so swollen and hot that she felt every inch of him when he pushed into her. Holly reached down and clutched his ass and pulled him in deeper. He thrust high up inside, in and out, the head of his dick stretching her each time he poked through.

His panting became shallow. His cock felt like it was growing harder and bigger with every second. His balls ached and begged for him to deposit their freshest load into this warm, loving hole.

“'s now!” he cried out at the very second his juice came and filled her. He continued his bucking and pumping until every drop was released into her and then he simply dropped down onto her flushed and heaving body.

After a moment, the kids got up from the table and moved to the sofa and just lay there, wrapped in each others' arms. Though they both knew they had another round in them, they decided there was plenty of time and decided to call it a night and go up to their separate rooms to sleep. Holly thought this was best, since by some twist of fate, the parents could unexpectedly arrive home in the night. She had to be careful.

The next day started early. Josh slept until seven but upon waking, demanded to be fed. Ben changed his diaper and dressed him for the day while Holly prepared his bottle. He was eating solid food now, but still had his milk with breakfast and at bedtime.

After everyone had eaten, they retreated to the backyard to play. It was sunny and hot and Ben felt like swimming. Since Holly had to watch the baby, she opted not to get in with him. She sat on the edge and kept an eye on him instead. Josh liked to have his feet dipped into the pool and watched while his big brother jumped off the side into the deep end.

This was how the morning was spent. Hanging around the house, playing, a little tv, some lunch. Around noon, Ben's Aunt Alex stopped by to see that they were making out alright. When she saw that Holly was doing well and very capable of this task, she said goodbye and left them on their own once again.

Josh went down for his nap around one o'clock. This gave Ben and Holly some free time and the two opted for a long, steamy shower in his parents' walk-in stall. When the temperature was just right, they ducked under the shower head, Benny standing behind Holly. His hands came up and played with her supple tits and she ground her ass into his hardness. With the mixture of soap and water, their bodies were slippery and Benny's cock disappeared between her butt cheeks. He loved the way it felt and he grasped her hips and humped and humped into her crease.

Holly didn't want Ben to give up his load this way and she turned, kissed him hard, driving her tongue into his mouth. His cock now poked into the v-shape between her legs and she reached down for it. Soapy and slick and hard as a rock, she rubbed him slowly. Ben enjoyed the sensation as he watched her wet tits dance in front of him.

She told him to lean into the spray and get all the soap off, then knelt onto the shower floor. Instead of using her mouth, she simply stroked his dick, inches from her face. Ben watched from above. He loved the way her fingers curved around him, held him just tight enough that her hand glided down his shaft. He loved seeing his bright cock head popping out of her fist. Holly could see his balls tightening and his stomach contracting and without a sound from above, Ben's erection spasmed three times before his liquid erupted out of him and splattered across Holly's chest. She shook the last of it out and licked the tip for good measure before smiling up at the satisfied boy.

Unexpectedly ripping them out of their euphoria, the doorbell.

“Shit!” Holly snapped.

“Who's that, I wonder?” Ben questioned her, as if she had a better idea of who it might be.

“It doesn't matter, quick, get dried off and get dressed!” She urged him.

Holly jumped from the shower, patted her hair with a towel, hastily dried her body and threw on some sweats.

She bounded down the stairs and was out of breath when she came to the door. Taking a second to relax, she opened it to see her boyfriend, Jesse, standing in front of her, a big smile on his face.

“Hey babe. I just called your house and your mom told me where you were. to ourselves for the night. Sweet!” Jesse leered.

“Well, no...I mean, yeah, I'm here for the weekend, but not alone. The kids are here. So...” she was thinking at warp speed about how to get rid of him. She enjoyed his company, of course, but this was a one-time opportunity for her and Benny. She didn't want to waste it.

“I know that. But they have to go to bed sometime, right?” He was not going to be easy to convince.

“Hmm, yeah.”

“Why are you wet?” Jesse finally noticed.

“Oh, um...we just got out of the pool. Benny and me.” Quick thinking.

At that moment, Benny wandered in, took one look at their visitor and became visibly put-out by his presence.

Shortly after Jesse's unexpected arrival, Josh woke from his nap, cranky and poopy. The spell was over again for now. And so the day went on, Jesse hanging around, waiting for the hours to pass so he could take advantage of this jackpot of privacy. Holly was still working out how to get rid of him. And Ben was reluctantly going with the flow, knowing there wasn't much he could do about it all.

Around four, they all walked to the park. Ben felt a little silly, playing around on the equipment like a little kid, even though he'd just repeatedly nailed his babysitter, but he went along with it. Holly and Jesse pushed Josh on the baby swing, much to the boy's delight. At least it put him in a better mood than he was in when he woke up.

Jesse suggested he and Ben play a little tether ball. After a few minutes, Ben actually seemed as though he was enjoying himself. They stayed for an hour or so, grabbing an ice cream for the walk back home.

After cleaning the baby's hands and face in the kitchen, Holly snapped him into his high chair and asked the guys what they wanted to do for dinner. Comically, and at the same time, they both declared, “Pizza”.

Jesse got the number from the take-out menu on the side of the fridge and called in the order. Since it was Saturday night, they were looking at an hour and a half wait on the delivery.

“Hey, why don't we go for a quick swim before it gets here?” Jesse offered.

“Ben? What do you think?” Holly asked.

“Yeah, I guess so. Sure.” Ben was actually having a better time than he thought he would with Jesse around. He really kind of liked him. Jesse didn't treat Benny like a kid or ignore him like a high school boy would normally do. And that was pretty cool in Ben's book.

This time, Holly decided she'd get in with them, since there were two older people to watch out for the kids, just in case. So, she got her tiny suit out of her bag and changed. She met the boys out back with the baby and joined them in the warm, clear water. Josh enjoyed it just as much as he had the first time today. Holly and Jesse took turns dunking his squirming little body into the water and he squealed with joy every time, splashing around with his hands.

To Holly's amazement, Ben crept up behind Jesse and swept a giant wave of water up the back of him. Laughing, Jesse spun around and dove after the retreating boy. The two of them were really hitting it off. That was a little pressure off her anyway.

She watched the two of them play-fighting with pool noodles, whacking each other across the backs and wrestling around as she and Josh sat on the pool steps in relative safety. They were all actually having a blast together. So the day wasn't a complete waste.

They knew the pizza would be arriving soon and they all got out and dried off. Once in the house, they broke off into separate rooms to change. Jesse and Ben met in the living room just as the doorbell was ringing. Holly came into the room and handed them some of the spending money Mr. Gregson had left for things such as this.

The boys brought the huge pizza box back to the kitchen so they could all eat together while Holly fed Josh at his high chair. Ben and her boyfriend continued their debate about their favourite baseball players and the best sci-fi characters of all time while Holly listened and tended to the baby.

Ben excused himself shortly after downing his third slice of pizza to go to the bathroom. Jesse took this opportunity to share something with Holly that had happened in the pool.

“He's pretty cool, Ben. I like him.” he said.

“Yeah, he's a good kid.” Holly agreed.

“I don't know about the kid part...” Jesse said, chuckling.

“What do you mean by that?” Holly asked.

“When we were wrestling around earlier, in the pool...” he brought his hand up to cover his grin, “ he pushed up against me and he had a wicked boner going on.”

“What?!” Holly gasped.

“For real, I swear. I could feel it on my leg, hard as a rock.” Jesse giggled like a kid.

“It was probably just because of the water. He was getting cold or something...” Holly offered back.

“Um, babe...the opposite usually happens when you're cold.” She knew this, but what else could she say?

“I'm sure it wasn't because you turned him on, you freak.” Holly laughed and tried to explain it away.

“Hehe, was a little freaky though.” Jesse smirked and took Holly by the waist. He pulled her tight to his chest and pressed his lips against hers. She kissed him back with equal passion and felt arousal seeping back into her body.

Ben walked in on them at just this moment.

To Holly's surprise, he only laughed and called them horndogs and a promptly asked them which DVD they wanted to watch.

Holly left the guys to it while she took Josh upstairs and got him ready for bed. The baby was visibly sleepy tonight after his long, play-filled day. She dressed him in his pj’s and snuggled up with him in the big, cozy glider and read him half a story before his eyelids drooped and he fell soundly asleep.

The rest of the evening passed quietly. Jesse and Ben had, of course, chosen Star Wars and were glued to the tv set during the entire movie, bantering back and forth over the best lines and the coolest weapons.

Ben had realized a long while ago that nothing would happen between himself and Holly tonight, not while Jesse was here, so when the film ended, he said goodnight and headed for his room. He knew he wouldn't be getting much sleep tonight, knowing that the two of them were downstairs, ready to rip each others' clothes off. He wanted to see Holly naked body so badly right now. His penis was jutting out inside his pajama bottoms and he ached for release. Guess he was on his own tonight....unless....

After enough time had passed that Holly and Jesse might assume he was asleep, Ben got out of bed and silently made his way down the stairs. He peeked around the corner into the living room and sure enough...the two teenagers were naked, on the floor, kissing. Holly was stroking Jesse's cock and Jesse was squishing the life out of Holly's tits under the dim background light of the television.

Ben knew they could barely see him here in the dark corner of the room, so he took the chance and pulled his engorged dick out of the front hole in his pants. He rubbed his shaft and head, moving occasionally down to his balls as he spied on his babysitter and her boyfriend getting it on. He knew Holly's curves by heart now and he imagined himself touching her, tasting all of her flavours. He watched as Jesse got up onto his knees and fed his cock into Holly's waiting mouth below him. She sucked him the same way she sucked Benny. Slow and deep with her hand around the base, moving it around and guiding the penis between her lips. Ben could hear the constant slurping as her mouth devoured him. He watched Jesse's ass clench as he gently rocked into her.

Without realizing it, Ben let out a short moan and froze when Jesse turned his head to look at him.

Caught in the act, Ben just stood there, his cock in hand, afraid of what Jesse might do now. But all the teenage boy did was smile at him. In fact, he kept watching Benny as he wove his fingers through Holly's hair and pulled her onto him a little harder.

Ben saw Jesse's gaze travel down his young body to his stiff little prick. The older boy watched intently as Ben pulled his own cock to the exact rhythm of Holly's sucking.

After a minute or two, Jesse motioned with a finger for Ben to come closer. Not knowing what was in store, the boy did just that. He came to stand beside Jesse, who then instructed Ben to kneel. Holly tried to protest but was met with deeper thrusts by Jesse.

Her boyfriend then took her hand and placed it on Ben's rigid pole. Giving in to this unexpected madness, Holly began to jerk the young boy while she continued to suck the older. Both boys were feasting their eyes on the girl's glowing body as they received their separate pleasures. They soon were both craving a taste of the taut, smooth skin beneath them and each came to lay on either side of her.

Jesse took a swollen nipple into his warm mouth while Ben parted her thighs and inched his hand between them. Holly closed her eyes and let the feelings take her over. She could never have imagined this perfect scenario. Two boys, years apart in age, but close in experience, coming together to make her body erupt with sensations beyond her belief.

She writhed under Ben's probing fingers and Jesse's suckling mouth. She wanted to beg one of them, both of them, to fill her up immediately with their hardness. Before she could, she felt Ben move down her body, into her open legs and press his lips into her heated, wet folds. His tongue darted out, flicking across her pussy lips, over her clit, and then inside her. He swiped it back and forth, drinking in her juices. Jesse smoothed his hand down over her stomach and laid a finger on her sensitive clitoris and began to dab it expertly as Ben ate away slightly further below.

Her insides were screaming, burning up, needing to let go...when Benny sensed this, he eased up, not wanting her to give in to it just yet. He was loving every second of her taste.

Before Ben knew what was happening, he felt a hand close around his cock. His eyes flew open and he saw that Jesse had inched closer to him and was now positioning himself near the boy's groin. Jesse gently rolled the boy onto his side, told him to keep licking and just go with it.

Only a second later, Ben's cock was being swallowed by the older boy and he didn't even have a chance to consider the rightness of it before the pure eroticism of it kicked in. Holly leaned up to watch the unbelievable spectacle of it all, Ben pleasuring her, Jesse pleasuring Ben...oh my God...she was going to explode from sensory overload.

And explode she did, releasing her deliciousness across Benny's tongue. She shuddered violently as the boy moaned against her pulsing lips.
Jesse had Ben's entire shaft in his mouth, bouncing his tongue off of it from the inside, squeezing and tugging on the boy's balls and Ben couldn't take a second more. He stiffened, grunted and blew his preteen spunk deep into the throat of the high school senior.

Jesse kept milking Ben's dick, draining it completely, savoring the foreign taste of it. His own cock was throbbing and he knew he had to find a nice, warm place for it soon.

He let Benny slip from his mouth and he deftly moved back to Holly's side. He took her by the waist, turned her over and pushed her onto her knees. He spread her legs apart and entered her, unapologetically, with a hard, forceful thrust. Holly's body was driven forward with the invasion but she had been craving this fullness for hours and now she was finally being served.

Before Ben could even think about becoming hard again, Jesse was already at his boiling point, pounding Holly's hot cunt like a piston. Ben just lay on his back and watched the older boy's face go from intense to almost hostile as his body slammed his babysitter and lover over and over, deeper and harder. He saw Jesse's fingers digging into Holly's ass and with one final, roaring plunge, Jesse clenched his jaw, growled and shot his pent-up seed into the girls tight, wet hole.

Exhausted, panting, sweating, the kids all collapsed in a heap together on the floor, their hot skin sticking pleasantly to each body part it came in contact with.

After a few minutes of reflection, Holly breathed a gigantic sigh...

“Um..did that just happen?” she laughed and the boys joined in.

To be continued....

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