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Babysitting Benny - Chapter 3

I've had a lot of people asking for Part III. Here it is, finally! Sorry for the long wait. I promise, Part IV will be up as well within the next few days. I hope it was worth the wait.

Chapter 3

Holly was finding it difficult to fall asleep after the long, uncomfortable drive home with Mr. Gregson. He didn't say a word to her except “goodnight”. In fact, she couldn't be sure if he had really found anything out at all. It just seemed strange that he wouldn't have mentioned it, or worse, called the police. Maybe she had imagined him whispering in her ear...either way, she was never going back to that house. Never.

Still, as she lay awake in her bed, she could still feel the warm tingling between her legs, still feel that hard little cock sliding up into her as she rode up and down on it. She knew she should be ashamed of herself for letting those things happen, but she wasn't. It felt right at the time and if she had the chance right now, she'd have Benny inside her every night, have his tongue slithering across her skin and his fingers exploring every inch of her body.

Well, that wasn't going to happen...not anymore.

2 months later

Holly and her boyfriend Jesse were spending their Saturday just hanging around the house. It was warming up outside and they were getting bored. They'd only begun having sex with each other a couple weeks ago but Jesse was too nervous about being caught while they were at Holly's parents' house, so they always had to find other things to do to take their minds off of it. Today, Holly suggested they take, Mig, her Australian Shepherd for a walk along the wooded path behind her house. It was a long trail running the entire length of her neighborhood, straight into the park in town.

They walked slowly, letting Mig sniff every little thing he came to. They weren't in any rush to get anywhere, just killing time since neither of them had any money to do anything exciting. Holly and Jesse passed several people along the way, a couple joggers, a family of four out on their bikes, another couple with their dog. They said hello to all of them and kept moving farther along the trail. They could hear kids laughing in the distance, nothing unusual. When they passed a break in the trees, Holly realized that they were in a spot that wasn't far from the Gregsons' home. When she saw the source of the laughter, her breath caught in her throat. It was Benny and a girl about his age. They were running towards her and Jesse, not yet noticing them.

Holly had tried to put her nights babysitting Benny in the back of her mind. She hadn't told a soul about what had happened and she hadn't seen the family since. But seeing the boy after all these weeks made her suddenly see the events so clearly in her mind, all in a fast instant-replay. Her legs began to tremble at the memory. It struck her that she never got that feeling when she was with Jesse – the butterflies in her stomach, the urgency, the need to just have him inside her. What was wrong with her? Too late to think about that now, Benny and his friend had seen them and were running straight for them.


“Hey Ben. How are you?” Holly replied.

“Good. I thought you must have moved away. I haven't seen you in a long time.” Holly noted the disappointment in the boy's voice.

“Oh, no...I've just been really busy with school and I had to give up babysitting for a while.” She hoped this might make him feel a little better. She didn't want him to think he had done anything wrong.

“Oh. That's ok. My new sitter's pretty cool. Her name's Amy.” Holly actually felt a tiny stab of jealousy at this news.

“Aw, that's good. I'm really glad you like her.” What else could she say without giving anything away?

“I liked you better. I wish you could come back. Maybe when school's out next summer...” His eyes looked up at her, hopeful.

“Yeah, maybe. I might be getting a job but we'll see.” She didn't want to fill him with a lot of hope as she knew full well she wouldn't be going back there. But by then, he might have forgotten all about her.

“This is my friend, Ashley. We go to the same school but she's older than me. Our moms are friends.” He had finally remembered that they weren't alone.

“Hi Ashley. This is my friend, Jesse. We go to school together too.” She introduced Jesse and after a bit of small talk, Jesse surprisingly suggested they have a game of hide and seek. He must be bored to want to play a silly kid's game with a couple ten year olds. He offered to count first and keep a hold of the dog. Everybody seemed up for it and when the countdown began, they all scattered.

After searching the woods for a few seconds, Holly spotted a large tree that had fallen over, way in the distance. She sprinted for it as quietly as she could manage. She hadn't noticed where the other two kids had headed, but she hunkered down and concentrated on Jesse's counting. It wasn't more than ten seconds later that Ben came round the corner of the tree and snuggled up to her.

“I couldn't find anyplace else to hide. Hope you don't mind” he said.

“ But we have to be quiet. Ok?” She was surprised that he had followed her here. For a young boy, he certainly wasn't shy.


“Ben, we have to be really quiet or Jesse will find us first.” she whispered.

“I don't care. I just wanted to talk to you alone. I really miss you. I wanna do stuff with you again. You know, like before.”

Wow, she had definitely not expected this. She would never have brought that up with him, afraid she might embarrass him.

“Benny, we can't talk about that here. What if someone heard us?”

“Well, when can we talk about it?” he pleaded.

Holly sighed.

“Ok, let's just play this with our friends for a little while longer and you and I can meet back here after supper, if you're allowed out that late. Is that ok?” What was she doing? Telling him to meet her...she was leading him on. She knew what he wanted and she shouldn't be encouraging him in any way. This had to be over between them. It wasn't right.

But she wanted to. She wanted to be alone with him and tell him that she cared about him a lot but they couldn't do those things together anymore. She had a boyfriend and Benny was too young. And she would tell him that. She didn't want to hurt him, but it was just the way things had to be.


Because it wasn't dark yet, Ben's mom told him he could go back outside for an hour after supper. He wasted no time running back to the spot Holly had agreed to meet him. And she was already there.

He was out of breath as he walked around the tree and sat down beside her.

She started to speak in a soft, sisterly voice...

“Benny, I know why you wanted to come back here and I don't think it's a good idea. We could get in a lot of trouble if we got caught doing the things we were doing.” She tried to sound very grown-up.

“But I'm not gonna tell anybody. Honest.”

He reached out and touched her leg. The shivers ran straight through her body.

“Can I kiss you? Please, Holly?” he begged.

“Benny, no. No kissing. No nothing. I just can't do it.” But God, she wanted to. She could already feel the wetness in her panties. She was aching for this boy to touch her and kiss her.

“Just one little kiss...pleeeease?” He smiled at her and it was just that easy to break her resolve.

She leaned over and met Benny's lips with her own. It was perfect. It made her skin tingle and her heart race. She moved her hand up to cup his face just as his tongue began to push against hers.

Ben moved a little closer and slid his arm around her waist, pulling her closer to him. He could feel her breasts pushing into his chest and his cock sprang up inside his shorts.

They kissed like this for what seemed like hours but could only have been a few minutes before they broke free of each other. The sound of branches snapping made them stop and survey the trees around them. They were soon satisfied that nobody was near and continued what they had started.

“Benny, it feels so good when you kiss me. You even remembered the way I showed you, with your tongue and everything.” It all came back to her in a wave, their hot young bodies crashing together, the sounds and smells, the unabashed need to feel his still-growing, but strong, capable cock inside her body.

“I remembered all the ways you showed me to use my tongue.” He laughed shyly. Holly couldn't believe how confident he was. The boys her own age weren't even brave enough to talk like this with girls. It just made her want him even more.

She couldn't control it, she dropped her hand onto Benny's leg and ran it up until it was resting on the stiff mound below the fabric. He let out a little gasp of air and wriggled beneath her touch, then relaxed and let her continue. She stroked him through his clothes until she could wait no more, and with both hands, she began to unsnap the button and pull down the fly. Ben moved up on to his knees so that she could pull his shorts down easily and watched her eagerly slip them off of him. It was only seconds after his erect penis sprang out of his underwear that Holly was bending down and taking his full length into her warm, wet mouth. She hummed around it, sucking and slurping, stroking the base and licking the head. Ben's body was shaking. She fondled his tight, round balls and gave them a small squeeze. He couldn't control himself, it felt so good, he just bucked into her face one more time and let go into her mouth. His semen was minimal but the sensation was overwhelming. He dropped back to the ground, his little dick still hard, and he just closed his eyes and sighed.

“Oh my God, I forgot how much I loved doing that to you. You fit perfectly in my mouth and you taste so good when you cum.” She was smiling and not even noticing that her hand had slipped into her own shorts. But Benny noticed. He recovered quickly and got back to his knees. He reached over and placed his hands over Holly's breasts and kissed her mouth at the same time.

As she absorbed the sensation of his thumbs rubbing her nipples, she moaned, broke the kiss and told Ben to stop so she could make herself completely naked for him. She told him to do whatever he wanted to her firm, young body. And he wasted no time.

Her nipples were as pink and pointed as ever, her skin so soft and white. She had a thin, pale strip of hair above the slit of her pussy and he wanted to lick her everywhere. He began with her pretty little tits, squeezing them while he sucked one nipple, then the other, back and forth until she was writhing beneath him. He removed one hand and slipped it between her legs, his finger parting the moist folds and immediately penetrating her. He pushed it high up into her over and over again, his lips still plucking at her puckered, now-red nipples.

Her wet little hole was so tight around his finger and he could feel her quivering from the inside. His prick was as stiff as a board again and he wanted to poke it into her. As if she could sense his readiness, Holly sat up, his finger still probing her and pushed him down onto his back. She mounted him like a pony and sank down onto him, his boner easing into her sweet, soft, teenage tunnel.

Where they were experimenting the last time, this time she bucked on top of his young body like a bull rider and he pulled and twisted her nipples, making her yelp and cry out. Ben looked down past his stomach to watch her engulfing him, to see her swollen lips hugging his juice-coated cock and her tiny little button-clit smashing down onto him. He loved the sound of her ass slapping against his legs and the sight of her tits bouncing over his face.

Every hair on Holly's body was standing on end when the familiar wave came over her and she threw her head back. Her cunt clamped down hard and tight to Ben's dick and she was shaken forcefully by the orgasm that she had waited so so long for but never thought she'd have again. As she was just beginning to fall across Ben's chest, he reached behind her, clutched the cheeks of her ass in his fists, thrust up inside her several more times and came into her with his own earth-rocking climax.

The pair lay spent and panting there in the woods until Holly rolled off and lay on her back in the damp leaves. They were both lost in their own thoughts...Holly, wondering if she would ever be able to go without this again. Ben, thinking of how he would be able to convince her to start babysitting him again.

He knew it was time that his mother would be expecting him home but he didn't want to interrupt this closeness he had found again with Holly. He snuggled up to her and she turned to look at him as his hand came across her waist. Their eyes met for an instant before he leaned in and took her nipple into his mouth. His hand moved up and casually teased the other. The kids lay like this for a long time, Ben nursing her soft breasts and Holly purring quietly underneath him.

Once again, it was time to split up and go to their separate homes before people came looking for them. Only this time, both seemed content in the knowledge that they would be together again very soon.


Over the next few days, the two managed to sneak away from their own friends and families and find a private place where they could have a quick fuck before anyone noticed they were gone. It was hard for them to have an extended time together because Ben was so much younger and rarely allowed to be on his own. Until one Saturday afternoon when Ashley was dropped off at his house for the day while their moms went shopping. They had taken the baby with them. Ben's dad was closed up in his office, working, and that gave Ben an idea.

He and Ashley had recently been having little show-and-tell sessions. He'd take out his dick and let her touch it. Then she would pull off her top and let him play with her boobs. He loved touching Holly's much more but he couldn't always be with her and Ashley was willing to play with him. She seemed curious and always eager when he brought it up. The first time he asked her if she wanted to lick him down there, she was hesitant, but he told her it's what boys and girls did all the time and it felt really good. She did it and she decided that it was fun and it made her body tingle and she liked the feeling. They promised never to tell on each other and played the game as often as they could.

Today, he and Ashley went out back and up into the treehouse and he told her what he and Holly did together. Her eyes were wide as she listened. She couldn't believe it. Holly was so much older and so pretty and she had a boyfriend. Ashley didn't recognize the other feeling she had upon hearing this news. Her first experience with actual jealousy.

After she questioned him for all the details, she asked him if he ever wanted to do those things with her too. Ben said yes, every time she licked his penis and made him hard he had wanted to put it inside her but he was scared to ask.

At this, Ashley began to take her clothes off and told Ben to do the same. He'd never seen her pussy before now and when he got a look at it, his pole sprang to immediate attention. Without thinking, he instantly reached out and began to stroke her between the legs. She jumped back at first, not expecting the contact. When she felt the goosebumps and the warm sensations, she relaxed a little, even spreading her legs apart a couple more inches.

“It's soft.” Ben told her.

“Does it feel the same as hers?” Ashley asked, shyly.

“Kind of. It doesn't have hair at the top like hers does. Let's lay down, wanna?” He suggested to his friend.

Ashley lay back on the sleeping bag that was a fixture of the treehouse and Ben lay beside her, leaning on one arm and quickly reaching for the small mound that was her preteen breast. He tweaked the nipple to erection, loving the way it puckered in front of his eyes. Her nipples were smaller than Holly's, and a little darker but they responded just the same when his mouth came down over one. As he suckled at one and then the other, Ashley's hand traveled down between them and grasped his probing cock. She closed her small hand around it and began to stroke it the way he had shown her. He moaned softly with her left rosebud still clamped inside his lips. He rocked gently into her fist, feeling the blood rushing up the shaft and into the head. His balls rose and fell as she glided her hand over him and he knew it wouldn't take a lot more for him to go off.

Ben reluctantly pulled his mouth off Ashley's tit and moved between her legs. He placed his hands on her knees and pushed them apart and watched her open up to him. As her lips spread, he could hear that she was already fairly wet down there. He was also surprised to see that her clit was larger than Holly's. It pointed out at him and begged him to come down and suck it.

Ashley lay very still. This was all new for her. But she wanted to feel the way Holly felt when Ben did these things to her. She watched Ben's finger trace a line straight down her smooth slit. When it crossed her clit, she shivered.

Ben licked his lips and crouched down into Ashley's crotch. With his fingers, he pulled her tiny lips apart and pressed his mouth against her. Another shiver from her but he didn't stop. First, he lapped at it in long, slow strokes, tasting her fully. The flavour wasn't quite as strong as Holly's but it was delicious just the same. He found her teeny virgin hole with his tongue and probed into it as his thumb gently rubbed her swelling clitty. Ashley's hips began to sway beneath him and he licked his way back up and replaced his thumb with his mouth. Her cunt lips were puffier than Holly's were and he couldn't resist sucking them too, loving the sound it made when he pulled off them.

Ashley responded by soaking his face in her juice. And he knew she was ready. Good thing too, because Ben's dick was beginning to ache for release. He repositioned himself over her and spread his body out against hers. She could feel how hard he was against her pelvis. Then his hand moved between them as he took a hold of his cock and guided it to her silky opening. His little ass cheeks clenched tightly as he pushed into her. Her hole was trying to resist him but he could feel it giving way, slowly. When he felt that he was in past the head, he thrust up inside her in one great heave. Ashley cried out and he clamped his hand down over her mouth and kept sliding into her. When he was as far as he could go, he stopped and just held her until she stopped crying and looked into his eyes. Gently, he pulled out of her and without waiting, again he dove inside. And though her body was trembling, Ashley was beginning to relax. She threw her arms around Ben's neck and he took this as a sign to keep going.

He pumped his young dick into her silken, hairless flesh over and over. Her legs spread out to the sides, bouncing off the floorboards as he bucked on top of her. He could feel his balls slapping into her skin and they got tighter and tighter and he knew he was going to lose it. He couldn't hold back the sounds in his throat and he moaned, ah, ah, ah, ahhh...and felt his load spewing out of him into his best friend. As he lay on top of her, his cock still twitching and draining inside her, he thought of Holly. He was emptied but he wanted to be with her again so badly.

To be continued

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