The Babysitter
by Ashley
Copyright© 2022 by Ashley
Erotica Sex Story: Sixteen-year-old Chrissy takes a job babysitting for the Pierces's son Timmy. It turns out that little Timmy is actually fourteen... and he's not that little either.
Caution: This Erotica Sex Story contains strong sexual content, including mt/ft Coercion Consensual Drunk/Drugged Heterosexual Fiction Anal Sex Analingus Masturbation Oral Sex Babysitter .
Chrissy was sixteen. Her parents were reasonably generous but they would only buy her basic clothes for everyday wear. Anything special had to wait for birthdays and Christmas. She did receive an allowance which allowed her to save up for things but it was a slow process.
She was offered a babysitting job by friends of friends of her Mum, a Mister, and Missus Pierce. She gave them a ring and was a bit surprised when it was for a fourteen-year-old boy, but the money was good so she agreed to do it.
She turned up on the first night and the Pierces were waiting for her. They introduced themselves as Laura and Will and then called Timmy down. He was a cute little boy: only a little shorter than Chrissy, with short blonde hair and a really cheeky little grin on his lightly freckled face.
He was very polite when introduced to Chrissy but then went back up to his room.
His parents seemed really nice, and Laura showed her around.
“Help yourself to snacks and pop from the fridge,” she said as they went through the kitchen. “Timmy looks after himself mostly but we’re happier knowing that someone’s around to keep an eye on him.”
They went into the lounge.
“Feel free to watch what you want. We have Sky so we get most channels,” she told her and showed Chrissy where the remote was.
“Just pop your head around his door every now and again to check he’s OK,” Laura told her, and Chrissy nodded her agreement.
“We’re going to an awards presentation in the city and we should be back by about eleven. Make sure Timmy is in bed by nine-thirty and lights out by ten-thirty at the latest.”
“That’s fine,” Chrissy replied, thinking that they were a bit strict with the poor boy.
“These are both of our mobile numbers.” Laura continued, handing her a slip of paper. “You shouldn’t need them, but just in case.”
“OK,” said Chrissy, beginning to get a bit bored of her fussing. “you two have a lovely time.”
As soon as they’d left Timmy came down and found her scanning the channels on the TV.
“The good stuff is all the 900 channels” he suggested to her. Good grief, she thought, does he mean the adult channels?
“It’s protected, but the pin is 1710 - that’s Mum’s birthday - it wasn’t too hard to guess,” he said somewhat proudly, and sat down on the sofa next to her. Right next to her, so that his arm and leg were both touching hers.
“That’s fine but I think I’ll watch this,” she told him, settling on a chick flick that she kind of hoped might drive him back to his room.
“OK,” he replied seemingly happily, and annoyingly settled down to watch it with her.
He was a little too close for comfort and she tried to shuffle away a little but he kept moving with her until she was at the end of the sofa.
She got the distinct impression that he was spending as much time looking at her chest as he was at the film. She was wearing a not very revealing but quite tight T-shirt and had a sensible bra on underneath. It was quite cute that he found it so fascinating but that’s fourteen-year-old boys for you, she thought.
He was paying enough attention to the film to make sarky little comments now and again, some of which were actually quite funny and she was getting to quite like him.
“Can I make you a sandwich or something?” she asked him when the film finished.
“Sure, I could go for a cheese toasty.” He replied with his trademark cheeky grin. She raised an eyebrow at him but smiled back and headed to the kitchen.
When she came back there were two nearly naked girls making out on the screen and Timmy had his hand down the front of his jeans.
“Hands out of trousers and back on the girly film channel or no sandwich,” she said firmly. He looked a bit miffed but did as she said, As she handed him his sandwich she couldn’t help but notice the bulge in his jeans. It was big. Chrissy hadn’t seen a lot of cocks but she’d seen enough to know that it was big. No way a fourteen-year-old boy had one that size, she thought, he must’ve put a sock down there to wind her up.
They sat in silence eating their snacks. For what seemed a long time Chrissy resisted the urge to look at his groin but in the end, she gave in. Damn, if it was a sock then how come it had shrunk? He must have taken it out when she wasn’t looking. He must have, there was no other explanation. Was there?
Determined to know for sure, when she put her plate aside, she wriggled her bum on the sofa causing her knee-length skirt to ride up a bit. A couple more of those, at discrete intervals, and she was showing quite an expanse of thigh. Another glance over confirmed it - the bloody thing was huge! Well, maybe huge was overstating it, but it would be a very decent size on a full-grown man. On a fourteen-year-old boy it looked ... fuck, she had to admit to herself, it looked amazing.
Chrissy was getting a little hot under the collar and, if she was honest, a little hot between the legs too, when the house phone rang. She went to answer it and it was Laura.
“Sorry Chrissy, the whole thing’s running horribly late and Will’s been drinking. We could get a taxi and be back by about twelveish or ... I hate to ask, but is there any chance you could stay over?”
Chrissy thought about it for a while.
“We’d pay you double, and you can sleep in the spare room...”
Chrissy thought about it for a while longer.
“OK. We’ll pay you triple and you can help yourself to a few beers from the fridge.”
“Deal,” said Chrissy. Triple pay and some illicit drinking while she watched TV! “But I’ll need to check with my parents that it’s OK.”
“Thanks, Chrissy, you’re a lifesaver. Give us a ring if there’s a problem with your folks, otherwise, we’ll assume you’re set.”
Chrissy’s Mum was fine since she knew where she was and trusted her daughter.
Chrissy and Timmy watched some more TV while she drank two small bottles of beer and she finally persuaded him to go to bed at ten-fifteen.
At just after eleven, and after another two beers, she went up to check on him. She knocked on his door and, after a short pause, he said she could come in.
He was sitting up with the bedclothes up around his chest and he had a very red face. Chrissy laughed to herself and went over to tuck him in, which wasn’t necessary but seemed the thing to do.
“Aren’t you going to kiss me goodnight?” he asked with that cheeky grin. Chrissy was feeling a little tipsy by now and played along.
“OK. Shut your eyes and pucker up.” He did as he was asked and she bent over and kissed him on the top of the head.
“Awww.” He moaned.
Chrissy went to bed soon after and fell asleep pretty much straight away.
She had an intensely erotic dream. It started off with her last boyfriend, Dylan. Somehow her blouse and bra had disappeared and he was sucking on her nipples. It was lovely and it was making her very wet, which he soon found out because suddenly his fingers were inside her. She had let him finger her in the past but only outside her knickers. Now though she had no knickers on either and his fingers were stretching her so much it almost hurt. Almost, but the pain was somehow very, very nice.
Then, madly, Dylan morphed into Timmy and it was Timmy’s little fingers plunging in and out of her, and then it was Timmy’s mouth on her clitoris. In the dream, she just kept cumming and cumming as he expertly frigged her and sucked on her clit.
She woke up with her heart pounding, covered with sweat, and with her pussy drenched with her juices. She couldn’t believe how real it had felt. The orgasms she knew had been real - she could feel the faint aftershocks even now.
She peeled back the covers to see how much mess she’d made and was horrified to see blood mixed in with her vaginal secretions over her pussy and inner thighs. Fuck! she must have fingered herself and split her hymen a bit, she thought. But when she looked at her hands they were both clean and dry.
Luckily nothing had got onto the sheets and only a little on the T-shirt which was all she’d been sleeping in. She went to the bathroom to clean up, all the while trying to figure out what had happened to her. There only seemed to be one explanation, but she didn’t want to believe it.
There was a faint light under Timmy’s door but, when she peeked in, he seemed to be fast asleep.
The light was coming from a bedside lamp and she saw that he’d fallen asleep reading. She put the comic book to one side and then paused.
She wanted to see his hands, just to be sure, but they were under the covers. She’d just have a little peek. She lifted the corner but couldn’t quite see, so she lifted it a little higher.
His hands were around his erect penis, both of them! In his sleep, they moved along his shaft and the head emerged from the top fist. It was big and purple and shiny and Tina found herself licking her lips as she stared at it.
Her pussy, which she’d only just cleaned up, was wet again, and her hand unconsciously found its way there and fondled her slick lips.
She couldn’t believe that this small boy had such a massive member and she couldn’t tear her eyes away from it.
“What are Mummy and Daddy going to say when I tell them about this?” His voice was barely a whisper but it shocked her to the core.
“Er, we don’t have to tell them. Do we?” Chrissy replied hopefully.
“Well, that kind of depends, doesn’t it?” Timmy said with that cheeky grin that was now starting to get on Chrissy’s nerves. Oh God, she thought, what have I done?
“What did you have in mind?” she asked nervously.
“Well for a start it would seem fair to let me see what’s under that T-shirt.” Chrissy knew that she had very little choice and sighed deeply before taking hold of the bottom of the shirt and slowly drawing it up over her head.
When her head emerged Timmy had leaned forward in the bed and his eyes gleamed as he drank in the sight of her naked body.
“Wow!” he said softly. “you’re so, so pretty!” His gaze was boring into her sex and Chrissy was tempted to cover herself up but if this was the price of his silence she’d just have to pay it.
He was stroking his gorgeous cock as his eyes roamed slowly over her body and it was turning her on like crazy. Her nipples were hard and aching and she had a mad desire to fondle them for him, a desire she was unable to resist. His eyes lit up when he saw her caressing her little B-cup breasts and she shivered at the look of lust in his eyes.
Then it was her sex that was calling out to be touched and she ran a finger along her crease dipping slightly into the wetness there. What was it about this boy that had this effect on her? she wondered. Apart from the obvious, of course.
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