Babysitter and boy learn some new things together.
Holly usually wasn't allowed to babysit on school nights, but the Gregsons were friends of her parents. They weren't going to be out late and she had her homework finished, so her mom said yes. All she would be doing tonight anyway was talking to her friends on Messenger and painting her nails, might as well make a little money. The Gregsons only had two kids, Benny, the older boy and Josh was just a baby – he'd be asleep by the time she got there. Should be an easy night – home by 11.
Mr. Gregson answered the door and took Holly's coat.
“Jenny'll be down in a minute, she's just feeding the baby and we'll be out of your hair. We're only going to a friend's for dinner and a game, the number's on the fridge.”
Jenny called from upstairs, “Phil, show her around the kitchen!”
“Let's go check out the cupboards, Holly...got lots of junk food for you guys. Not too much for Benny before bed or he'll drive you crazy.”
Mr. Gregson wasn't lying about the junk food...it was pretty awesome. Her own parents were health food nuts, so this was gonna be great!
While Phil was showing her where they kept the soda, Benny ran in to the kitchen with his little boxer shorts and a t-shirt on.
“Hi Benny, do you remember me? I'm Holly.”
“Yeah, I remember you...you babysat me when mom and dad went to your house, a long time ago.”
“It wasn't that long ago, but you've sure gotten big!” Holly exclaimed. “How old are you now?”
Ben had a huge smile on his face, “I'm ten! How old are you?”
“I just turned fifteen. I go to the high school now.”
Jenny came running down the stairs just then and ushered Phil out into the hall.
“We'd better run, Sweetie, it took a little longer to get Joshy off to sleep and then I had to change my shirt.” Jenny said with a bit of a blush.
I knew she breastfed him, so she must've meant that she leaked onto her other shirt. Holly had never seen Jenny actually breastfeed Josh, but she thought it was cool. It didn't bother her like it did some people. It's a natural thing!
So, the Gregsons finally left, blowing kisses and spouting off phone numbers and bedtime instructions behind them.
Holly took Benny by the hand and said, “Let's go raid the fridge!”
“Yeah!” Ben shouted and danced into the kitchen.
They loaded up their arms with popcorn, sodas and ice cream sandwiches and made way for the living room sofa. Holly popped in a recorded tape that said Night at the Museum and jumped back down to the couch.
Benny laughed his ass off for the next hour and a half. This was one of Holly's favourite movies too. After the movie ended the tape kept rolling until the sequel started playing. Holly decided that since it was only 8 o'clock, Ben could stay up a little longer. They settled in a little deeper, the snacks long since devoured.
Ben rested his head on Holly's shoulder and seemed to be nodding off when the tape in the old VCR went screwy. It was snow for about three minutes and then something else came on. It was a man and woman in a pool, they were naked and kissing. Holly let out a gasp and went to get up when she felt Benny stirring beside her.
“What's this?” he asked
“Um...I don't know, I'm gonna shut it off,” Holly declared
“That man is sucking her boobies like Joshy does to Mom...”
“Oh...um...I guess he is.” Holly was at a loss for words.
They both just sat on the edge of the couch and watched, even though Holly knew she should be shielding Ben from the TV.
“Her boobies don't look like my moms though...” Ben kinda muttered.
“Every girls' look a little different, Benny,” Holly clarified.
“What do your look like, Holly?”
“Ben!!” Holly screeched.
“They look a lot smaller than my mom's”
“Well, that's because they are! And mine aren't filled with milk...” Holly blushed.
“They aren't? I thought they all had milk in them...”
“No, not unless you have a baby first,” Holly said.
“Will you let me see yours?” Ben asked with a straight face.
“Ben, you're only ten, you shouldn't ask me that!” Holly told him, a little shiver going down her belly.
“Just for a second...I want to see them. Please Holly...”
Holly thought about this for a second. What was the big deal? He was only a kid and so was she and it wasn't like there was much there to look at anyway.
“Fine, but only for a second and you can't tell ANYONE!”
Holly began unbuttoning her blouse and Benny sat quietly beside her, never taking his eyes off her chest.
She opened her blouse and showed him her pink flowered training bra. He told her he liked the way her boobies looked in it. They were all pushed up and kinda pointy.
She slipped her shirt off of her shoulders and sat there in only her bra. She reached up slowly and started to peel down one bra strap. She pulled it down until her soft, puffy nipple came into view. Another tingle went through her belly and she shivered.
“Can I touch it,” Ben asked softly.
“Um...Okay, but only for a sec.” Holly quickly exhaled the breath she had been holding in. Even though Benny was only ten, she felt excitement coursing through her. He couldn't know what he was doing to her. She barely had a clue herself, having only kissed a boy once at the winter formal last year.
The people on TV were now lying on the pool deck and the woman had the man's penis in her mouth. She was moving her lips up and down and the man was moaning. This was the first time Holly had ever seen man's penis, and it made her feel embarrassed.
Her eyes were pulled from the screen when she felt Ben's little hand stroking her breast. He was moving his palm back and forth like he was petting a puppy. A little breath escaped from Holly's lips when his thumb brushed over her nipple. She felt it stiffen and swell. She had never felt anything like this before and she liked it.
“Ben, keep doing that with your thumb...rub it over my nipple.” She couldn't help herself now.
While Ben was happy to keep flicking her tiny pink bud, Holly pulled on the other bra strap until her left breast popped into appearance. Benny wasted no time taking it into his other hand and giving it a squeeze. Both her nipples were now standing hard and reddening under his touch.
“Ben...maybe you should lick one...like the girl in the movie...would that be okay?” Holly asked with trepidation. She didn't want to make him do something he didn't want to do.
“Milk won't come out, will it? He asked her.
“No, I told you, you have to have a baby for it to do that...”
“Okay then, I want to.” Ben said, leaning in closer to the teenage babysitter's exposed breasts.
Benny flicked his tongue over her right nipple and them clamped his lips around it. He sucked like he had seen his baby brother do to his mother so many times.
Holly sighed and dropped her head back onto the couch. God, it felt so good. It can't be right for them to be doing this, but she just couldn't bring herself to pluck him off her tits.
She sat back up and watched him as he pinched her left nipple between his fingers and listened to the soft slurping going on on the other side. She couldn't believe how hard they were, like right after she got out of the swimming pool. She pushed her hand through Ben's hair and pulled him in closer. He pulled his lips off her right breast with a popping sound and looked up into her face with a big smile.
“That's really fun, Holly...I like the way your thingies feel on my tongue.” He was so proud of himself.
“It feels really good for me too, Ben...do you want to suck the other one now?” She had to have him sucking her titty, he couldn’t stop now.
He relocated his head and sucked her left nipple into his wet mouth...he sucked harder this time and flicked his tongue around it. Holly told him to straddle her lap so he could have access to both at the same time. When he put his legs on either side of hers and climbed up, Holly noticed a tiny tent forming in the front of Ben's shorts. He didn't seem to notice as he suckled away on her puckered nipples, one after the other, popping and slurping and groaning while his fingers massaged and pulled.
“Ben, do you feel funny?” she asked.
“Um...what do you mean?
“Like, kinda tingly or like you have butterflies in your stomach?” Holly thought that might be how he was feeling because that's exactly what she was feeling.
“Yeah...kind of like that...and my pee pee hurts a bit.” Benny said, squirmy gently on Holly's lap.
“Maybe your shorts are too tight Ben...do you think you should take your pee pee out and see if that helps?” What was she doing!? This was not right, but she desperately wanted to see his penis, especially since it was getting stiff.
“Okay...I'm gonna pull it out my pee hole in my shorts.”
He leaned back on her lap, and with her little titties bobbing in front of his face, he stuck two fingers into the hole and came out with his stiff little prick, poking straight out and his pert pink balls resting on top of the cloth opening.
They both stared down at it, Holly unbelieving the size of the head at the end of it. She didn't know a lot about boys' parts, but the knob of this boy's cock looked unusually big for his age. The rest of it was about the right size for his body. She really like the way it shined a bright pink and almost danced on its own around her belly-button.
Ben reached down and wrapped his right hand around it like he was going to pee. He let out a little sigh and then let go.
Holly was intrigued. She wanted to touch it herself. She couldn't imagine what it felt like, but she wanted to.
“Ben...can I touch it? Does it hurt?” She asked him, shyly.
“You can touch it Holly...it doesn't hurt at all anymore. I think my shorts WERE too tight. Look how hard and bouncy it is...!” he said with a tap on the top of his dick.
Holly slowly reached out and brushed her fingers along the shaft of her little charge's stiffy. He gave a little shudder and repositioned his hands on Holly's breasts, tweaking her nips in small half-circles.
She moved her hand up over the bulbous tip and back down the shaft.
“Does this feel OK?”
“Yep, it feels really good...you can rub it harder too. I do that sometimes. It feels awesome.”
Just then, Holly remember the TV and while the couple were now screwing their brains out, she remember what the woman had been doing to the man earlier.
“Ben, do you think that I could lick it. The woman in the video did and the man seemed to really like it. Would you like me to try that?” Please say yes, she thought!
“If you want to...” he said, not wanting to abandon her pretty tits so soon.
“OK then, you get off me and sit on the couch...I'll get between your legs on the floor like she did.” Holly was getting excited now...what was she doing?!
As she knelt in front of him on the floor, he opened his legs and pulled his t-shirt up higher, giving them both a great view of his beautiful prick. Ben took a hold of it and pointed it at Holly's face.
“Suck it Holly...I want you to suck it...” He was really into this, thought Holly. Guess she was feeling bad about this for no reason.
Holly's tongue came out and began a slow journey up the entire length of his shaft. She licked twice more before taking the whole rounded tip into her mouth. It was so soft and smooth as she motioned her lips up and down, up and down. Ben wiggled underneath her and put his hand on the back of her head. This caused an electric current through Holly and she moved faster and faster, her tongue never stopping, her lips never slowing.
She took hold of one of her own tits and pinched the pointed nipple so hard, she gasped. Ben was now writhing on the couch, little moans escaping his mouth. He reached down and grasped her other nipple, twisting and pulling on it, wishing it were between his lips.
Suddenly, Ben gave a quick shudder and Holly felt a miniscule spray of hot fluid shoot into her throat. She was not prepared for this and gave a little cough. It tasted a bit salty and had a stinging effect. She hardly noticed as she, herself was writhing back and forth, Ben stretching her nips and pulling her closer to him. He leaned down and sucked one into his mouth. She pushed her chest into his face and then pulled back swiftly, making her nipple pop out from between Ben's lips. She replaced it with the other and just as quickly removed it to the sound of suction.
Neither babysitter nor boy knew what to do next. So, they did what anyone did to learn more...research. They fast-forwarded through some video until they came upon the next couple. Only the man was naked so far and he was kissing her with his hand inside her panties.
“What's he doing?” Ben asked sincerely.
“I'm not sure, but it looks like she likes it...”
The man in the video moved the woman's panties to one side and revealed a trimmed and wet pussy.
Both kids gasped. Neither had seen anything like this before...well, Holly had seen her own but she barely had any hair there and she'd never seen it up close.
“Should I touch you there?” Ben wanted to know.
“Do you want to? It looks kinda yucky.” Holly was getting shy again, after all they had done so far.
“I think I want to...I've never seen a girl's pee pee before.” Ben was more enthusiastic than Holly would've thought.
Holly then stood up in front of Ben's beautiful little body, his penis still poking through his boxers, and still erect. She stepped out of her shorts and felt down the front of her own panties.
“They're a little wet...I think I might have peed a bit.” She gave a little laugh.
Benny sat forward almost directly in front of Holly's crotch. He inhaled as Holly bent and pulled her panties off. She stood back up and moved her legs slightly apart. Ben quickly snaked out a finger and touched her just above her clit.
“It is wet.”
He began rubbing slowly as his finger lodged deeper into her shallow slit.
“Benny, it feels good...keep rubbing it...”
Ben rubbed and rubbed until Holly couldn't take it...she pulled back and leaned onto the coffee table, spreading her legs to either side.
“Get between my legs like I did to you.”
Ben knelt down and leaned in...he could smell her sweetness and see the glistening opening before his eyes. He had no idea why, but he wanted to poke something into that little hole. Without even asking, he pushed his pointer finger inside her and she let out a small cry. He pulled out and plunged it in again, this time a little deeper. He just caught sight of the video again and did as the man was now doing. Ben bent in closer and flicked his tongue across the wet plain. Holly's legs began quivering as Ben rolled his tongue up and back across her clit and into her moist valley. He loved the way it tasted, a little salty and something else, something soapy, like she'd just gotten out of the bath. His first two fingers entered her while he kept up a quickening pace with his roaming tongue. Holly was jerking violently underneath him now and he had to keep moving his head to keep up with her. She was panting and groaning, thrashing and pulling his head into her.
“Ben! Lick me harder...don't stop licking me! Ben!”
Benny sucked her clit in between his lips and pulled on it just like he did her nipple and he liked it just as much, maybe more. His little boner was aching below him and he stroked it under the table with his free hand. All of a sudden, Holly's legs clamped onto the sides of his head and she bucked up into his mouth. With one last suck of her teeny clit, she cried out and ground his head into her pussy.
Neither had any idea what just happened.
After a couple minutes of silence and Ben gently lapping at Holly's mound, she sat up and held out a breast for Ben to suckle onto. He gladly took it in and feasted for a long while. Holly was still shivering and her legs felt like jelly.
On the TV in front of them, they watched the woman riding on top of the man, his penis buried in her pussy. He bucked into her from below and she screamed and scratched at his chest while he squashed her tits beneath his huge hands.
Holly and Ben both became a little embarrassed and stood up to dress quietly. She informed Ben that they had better get him up to bed after they got rid of their incriminating evidence in the VCR.
Ben ambled up the stairs and into the bathroom to brush his teeth, Holly right behind him. As he washed up, Holly checked on little Josh, still peacefully asleep in his crib.
After closing Josh's door, Holly found Ben laying on his bed on top of his covers.
“Ben, you know we can't tell anybody what we just did. They would be so mad at both of us.” She warned.
“I know. I'm not going to tell anyone, not even my dad. I promise.”
“Thanks Benny. It's also kind of embarrassing...I wouldn't want anyone to ever find out.”
“Okay Holly. And I'm really glad you came over. I think you're my favourite babysitter.” Ben confessed.
“I'll bet I am! No wonder!” Holly was still flattered.
She leaned in to give him a goodnight hug and he wrapped his arms tight around her. She then felt something pressing into her side. When she looked down to identify it, she realized that Ben's penis was poking up into his shorts again.
Ben immediately grabbed onto it and tried to push it down.
“Don't do that, Ben. You'll hurt yourself.” Holly admonished.
“What should I do? I don't want my mom or dad to see it...” Ben was almost in tears. Holly then remembered how young he really was. The things he had just done to her had made her forget that for a minute.
“Well...maybe if you rub it a bit it might go down. Want me to leave you alone for a while?” she asked kindly.
“No Holly...you have to do it.”
“Ben, your parents could come home at any minute. I can't be caught doing that to you. They'd kill me.”
“Please Holly...please. Hurry, before they see it sticking up.” He was starting to panic.
“Alright, but quick.”
Holly knelt on the bed and bent her head down onto Ben's stiff little pole. She sucked it in and took it all the way to the back of her throat. Ben's hand then snaked around her bum into the leg of her shorts and she felt his fingers probing her pussy again. She had to make him stop but just couldn't. It felt too good...too good.
He pumped two fingers in and out of her aching, virgin hole while she bobbed on his pulsing cock. When she couldn't stand it anymore, she got up off the bed, peeled off her shorts and panties in one swipe and told Ben she was going to try something she just saw on the video. If it hurt him, all he had to do was tell her to stop.
Holly knelt back onto the bed and swung her right leg across Ben's legs. She reached down and grasped his ten-year-old rod in her hand and guided it to the place where his fingers had just been. She hovered above him for a second and then slowly lowered herself onto his ruler-straight pole. She pushed down as Benny responded and pushed slowly upward. They both moaned collectively and Holly began to bounce gently at first, then could not stop herself from ramming her ass down into his legs.
Ben felt up her body and snatched Holly's tits once again, squeezing her teenage buds, twisting them and circling them with his thumbs. Holly panted above him as he rose to meet her pussy with his thrusting from below. He could feel his tiny balls slapping into her ass. She ground her dripping cunny into his pelvis and her clit was electrified.
Lights shining into the upstairs window alerted them to the Gregsons' arrival home. They just could not stop. Holly rode as hard as she could and Ben plucked at her nipples, telling her not to stop.
“I won't...I won't stop....Benny...Oh my God, Benny...Oh god, Oh God.....Ohh....”
She came with a shuddering violence onto his beautiful boy cock at the same time that Ben shot his marginal sperm up into her belly.
They could not savour the effects of their fucking as they heard a key in the lock downstairs.
Holly jumped up and pulled on her clothing, Ben tucked his prick back into his shorts and pulled the covers up over himself.
Holly blew him a kiss from the doorway as she met Ben's parents on the stairs. She hoped they wouldn't notice that she was somewhat out of breath.
“Hey Holly...how did things go?” asked Mr. Gregson.
“Oh, really good...I think Ben just had a little nightmare. I just checked in on him and he seems to be okay.” Holly covered her ass well.
“Oh good, I'm so glad they didn't give you any trouble...” Mrs. Gregson sighed.
“Nope...no trouble at all. I really love Ben...he's such a good kid. Really good.” Holly sang.
“Well then....can we possibly ask you to do it again on Saturday night?” Mr Gregson asked sheepishly.
“The Mrs. and I were invited to a Valentine dance at the armoury.”
“Of course...I'd really love to. Like...7 O'clock??”
“On the dot. Thanks Kiddo...we'll see ya Saturday then.” Mr Gregson slipped her a twenty and Holly slipped outside and down the block to her house with a dreamy smile on her face.