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Babysitting Benny - Chapter 2

Babysitting Benny – Chapter 2
Part two - Holly returns to the Gregson's home to babysit young Benny.


Standing in her sister's bedroom, Holly snuck her hand inside the tall dresser drawer and pulled out one of Jill's low-cut, silky lavender bras. She wanted to be prepared for her babysitting job tonight. As an afterthought, she reached back in and took out a matching see-through purple thong.

As she stood in front of her own mirror, wearing her older sister's naughty underwear, she was starting to become turned on by her own hardening, puffy nipples, her tight, round ass and the wettening slit forming between her teenage pussy lips. All she could thing about was lying back on her bed and rubbing her fingers through these panties and relieving herself of this desperate aching that she had been feeling since the last night at the Gregson's house.

She was still amazed that a ten year old boy could make her feel things that no high school guy ever had. She couldn't wait to get over there and take Benny into her arms, push him back across the living room coffee table and suck his rigid little cock until he cried. She remembered how it had been just a mouthful, but warm and pulsating, stiff and straight and exploding into her hot young mouth. Holly was salivating at the thought. She didn't know how she was going to contain her lust in front of Benny's parents tonight before they left her alone with him.

Only three more hours...three hours and she would spring on that sexy little boy and eat him alive. Oh God, seven o'clock couldn't come fast enough!


“Hello again Holly. Come in, come in. Grab a seat, Benny and Phil are in the backyard cleaning all the toys out of the pool.” Jenny Gregson sang as Holly walked into their home.

“I forgot that you had a pool. Must be nice on such hot days...” Holly said.

“You know, sweetheart, you're welcome to come join us anytime! I'm sure Benny would love to have someone to play around with.”

Blushing, Holly replied, “Um...yeah, maybe I will sometime.”

Holly moved over to the couch and Jenny sat down beside her with baby Josh in her arms. Before Holly could open her mouth to speak, Mrs. Gregson was unclasping her nursing bra and massaging her breast. Baby Josh was squirming on her lap and she brought him up and tilted his head toward her bulging pink nipple. His tiny baby lips clasped on and suckled, his eyes closing as he drank himself into a deep sleep. It was only minutes until he nodded off and Jenny pulled his still sucking mouth from her breast with a popping suction. Holly didn't say a word but she imagined herself now leaning over and taking one of those succulent nips into her own mouth and having Jenny reach up into her blouse, under her sister's silk bra, and rolling her teenage nipples between her fingers. Never had Holly felt aroused by a woman, especially a woman as old as her own mother.

As Jenny Gregson was tucking her breast back into her shirt, the boys entered the house through the patio door.

Benny smiled shyly towards her, tucking his head into his chest.

“So, are we ready to head out, Honey? Hey Holly, how are ya?” Phil asked his wife.

“Just let me tuck Joshy in and we'll go...”

“I'm fine, Mr. Gregson. I'm glad you asked me to come over again. Ben and I had a fun time. He's a great kid.” Don't push it Hol, she thought...

“Ha-ha, that he is...hey Ben, come say hello to Holly.”

“Hi Holly, “ Ben said while standing behind the sofa.

Holly had a thought.
“Ben, are you sick of swimming yet? Maybe we could jump in the pool for a while...It's still warm out. What do ya think?”

“Um...maybe. Is that okay Dad?” Ben seemed to be coming around, loosening up around her some.

“Sure buddy, just make sure you listen to Holly and stay in the shallow end.” Phil warned.

Jenny came down the stairs just then, purse in hand, and ushered Phil out the door once again. It was like a weight had been lifted from Holly's shoulders.

“So you wanna swim then?” Holly felt a little shy now too. She didn't want to hope that Ben would want a repeat performance of the last time, but she couldn't help herself. She wouldn't push him, just let things happen naturally.

Since Benny was still wearing his swimming trunks they had no need to wait. They headed back out the patio doors toward the pool.

She grabbed the baby monitor on her way outside so she would hear if Josh woke up.

“Did you bring a suit?” Ben asked her.

“Oh, shoot! I forgot about that...I guess I could just go in my underwear.”

“Oh...okay, I guess that's alright...I'm gonna get in on the slide Holly! Watch me!” Ben didn't seem to think there was anything unusual about Holly stripping out of her clothes. He seemed like a normal, uncorrupted little boy. Hmmph! Maybe he thought it was all a dream or maybe he just wanted to forget about everything.

Luckily, the Gregson's house was surrounded by a tall fence so Holly didn't worry about snooping neighbours. She slid seamlessly into the water and dove straight under as Ben swooped in from the slide. They played around in the shallow end, Ben diving around Holly's legs with his snorkel. Holly just waded around and watched. She loved the way his tiny bum floated above the surface. She just wanted to get her hands on it.

“Whoa!” She gulped as Ben's forehead banged into her crotch underwater. He stood straight up in front of her and looked at her as though he was just caught doing something bad. But his eyes were drawn from her face down to her tiny bra/swim top. The silk was clinging like a skin to her apple-sized breasts. Her nipples were poking at the fabric as the cool water had turned them hard as diamonds. Ben stood frozen, gazing longingly.
Holly began to feel a pressing sensation on her leg. She looked down to see Ben's rock-hard boner stretching away from his shorts. Yes! It WAS going to happen! This was what she had been waiting for.

She took him by the hands and placed them gently over the cups of her bra.

“Touch me Benny. I've waited all week for this. Have you been thinking about me?” She knew what she wanted his answer to be.

“I think so. But it was bad, what we did.” His lower lip was quivering...but so was his penis against her leg.

“Ben, it wasn't bad...because it made us feel so good. It felt good to you, right?”

“Yeah...” His thumb was moving over her tit as he spoke.

“Well, maybe we should do it again. Do you want to Ben?” Please, please let him want to.

She bent down and grasped his rod inside his trunks and stroked him slowly. He couldn't help but hump into her hand.

It took him only seconds to respond and he peeled back the cups of her bra and exposed her perfect nipples to the cool evening air. They were puckered and pointing toward Ben's face. He was just about the exact height, right in front of her chest. His tongue snaked out and licked across the surface of her left nipple. He fondled both tits and sucked back and forth between each. Holly tucked her hand into his waistband and cupped his balls into her fist, gently massaging them.

Holly remembered something then that she learned in school, that people are much lighter in the water.

“Ben, I want your penis inside me again. Remember how awesome that felt when I rode on top of you in your bed?”

“Yeah, I really liked that Holly.” He said through mouthfuls of breast.

“Back up against the side of the pool.” She lightly shoved him backwards.

She pulled his trunks down and exposed his rounded butt, his cock bobbing toward the water's surface. Ben pulled her into him and grabbed her ass, looping his thumbs into her panties. He rolled them off her tight body and moved his hands back up, kneading her ass cheeks, pulling them apart and squishing them back together. The sensation of the water moving in and out of her crack was driving Holly crazy. She told Ben to keep a hold of her ass and then she wrapped her suntanned legs around his waist.

Ben was amazed that he was able to hold Holly up. She was twice his size.

Holly held on to the young boy's neck with one hand and felt under the water for his prick. She guided it to her sweet spot and impaled her pussy onto it. They both inhaled sharply as Holly began to buck on Ben's lap. He kept squeezing her ass as he pulled and pushed her on and off his cock. Combined with the water, this was the most amazing thing he had ever felt. And this position was so perfect because her tiny tits bobbed in front of his face. Each time she came into him, he grabbed a nipple between his lips. When she was bucking outward, it would pop out of his mouth.
Ben was getting furiously excited and accidentally let his fingers enter the crack of her bum. Holly moaned loudly so Ben proceeded deeper. He felt her little bum hole with his finger and rubbed. She bounced madly onto his cock and threw her head back.

“Ben! Keep doing that! Press your finger into my bum!”

“Really? Do you want my finger all the way in?” He couldn't believe it. It sounded gross but it was feeling pretty good to him. The only problem was that he wanted to watch it go in.

“Yeah, I think I do...push it in...”

“It's hard to reach that far. Is there a better way?” he asked, even though he hated to stop Holly from fucking him in his parents' pool.

“Um...let me think. Um, okay...let's try it on the steps.” she offered, hopping off his legs and swimming to the nearest end of the pool.

“How about if I bend over, like this.” She bent over and her entire ass was in plain sight. Ben's eyes almost popped. He could see her pussy and her asshole at the same time and his boy-pole led him straight to both.

“This way, you can still put it in me and you can reach my back hole at the same time.” This was new to Holly. She had never heard of anyone doing anything like this, but just having Ben's finger brush her back there made her want to explore this further.

Ben leaned into her again, this time from behind. He grasped her cheeks and spread them wide open as Holly swayed with her elbows on the top step, her knees on the bottom.

He couldn't resist and bent his head into her bottom. He made a long swipe with his tongue from her clit to her virgin bum hole. She shivered beneath his breath. Neither could stand the anticipation any longer and Ben took hold of his arrow-straight penis and guided it into the hole it was becoming very familiar with. He rocked into her while he held tight to her buttocks, one in each hand. His little ass pumped frantically behind him.

“Do it now, Ben...put your finger in my bottom...” Holly pleaded.

Ben pulled her ass apart as far as he could with one hand and pointed his finger right at her opening. He wiggled it around the outside as Holly's knees almost buckled. His finger poked it's way inside, turning as it went. Slowly, the rhythm of his ass-poking began to mimic the rhythm of his frenzied fucking.

Holly wasn't moaning anymore but had begun to grunt and pant. She was actually being screwed in both her holes at the same time. It felt like two boys instead of just the one. This thought pushed her over the edge and she came, shuddering all around Ben's thrashing cock. At nearly the same time Ben stopped-up cold and she knew he was squirting into her tight cunny. His whole body went rigid and his finger stopped probing her. His little-man body collapsed onto her back and her knees finally gave way underneath her. They splashed down into the water and they watched a tiny trickle of boy-cum trickle into the pool.
As the two young lovers lay spent on the steps, the baby monitor began to crackle and they could hear Josh begin to whimper inside the house.

They quickly redressed and dried themselves off. Holly ran inside and up the stairs to make sure the baby was okay. Josh was laying face-up in his crib, eyes wide open, but not unhappy. She gently rubbed his belly and he drifted back to sleep.

When she returned downstairs, Ben was in his Pj’s and sitting on the floor in front of the TV, a bag of chips in his lap. Just like nothing had ever happened between them in the pool. Holly had to smile at his innocence.

They had been watching The Family Channel for an hour or so when Ben asked a question that shocked Holly.

“Holly, do you think I could fit my pee pee into your bum hole?”

Holy shit! She could not believe he was asking her this! How hot was this? Ben was ten, she was fifteen and he was wondering if he could fuck her in the ass. This just did not happen every day.

“We could try it, if you want. Do you feel like doing it tonight or do you want to wait until next time?” she asked, hoping.

Ben answered her by standing up, pulling down the front of his shorts and showing her his little bullet, ready and willing to go for it right now!

Since Holly's panties were soaked from the pool and she had stashed them in her purse, she only had to pull off her shorts and she was ready for him, then and there. She dropped to her knees and lay across the couch. Ben raced across the room and lined himself up with her as she spread her cheeks open and waited for his assault.

Ben pressed his penis up to her tight pucker but it wasn't going was so tight, too tight. He pressed his finger in instead and moved it all around. Holly rocked against him.

He finger-fucked her ass for a few minutes and when he pulled out of her he could tell that the opening had gotten a bit larger. Ben rubbed his prick in his hand, then he swiped it up into her pussy once or twice and without warning her, he plunged himself to the hilt into her waiting bum hole.

Holly's legs were like jelly and they bashed against the couch as Ben bumped his cock into her with the strength of a grown man. His balls slapped up into her cunny lips as he stretched her back end wide open.

Holly fingered her clit in fast circles. She could feel her orgasm building.

“Pump that little dick up into me Benny. Look at you, you're fucking my asshole. Does it feel good Benny, does my little asshole feel good around your stiff dick?” she panted.

Ben couldn't answer her...he could feel his spunk bubbling up from his balls. Then he blew! And he couldn't stop, his cum just kept spraying up into her. His fingers dug deep into her ass and he could feel her clench her muscles around his penis. Nothing could ever feel as good as this. Nothing.
When she was sure he was finished, Holly turned around and pulled Benny towards her. She kissed him full on the mouth and he kissed her back. She squeezed his butt and rubbed her tits into his chest as she leaned in and said, “I want you to be my boyfriend Ben. Will you be my boyfriend?”

He didn't even hesitate. “Yes.”

“We still can't ever tell anybody. It's gotta be a secret. Okay?” She had to stress this because he was still only a kid and could tell his parents or friends by accident.

“Okay Holly.”

“I love you Benny.”

“I love you too...”

“We'd better get you off to bed, for real this time,” she winked.


About a half hour later, the Gregson's returned home. Jenny went right upstairs to check on the boys after saying a quick goodnight to Holly.

Mr. Gregson waited until his wife had left the room, pulled out a twenty dollar bill and handed it to her. As Holly went to take it, he pulled it back slightly. He leaned in closer to her and whispered, “Ever heard of a nanny-cam?”

Holly froze. She looked into Paul Gregson's eyes with tears beginning to well.

He just smiled back at her and said, “Let me give you a ride home...”

To Be Continued...

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