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, 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 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, your 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 it’s 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.
“Can I see your arse?” he said pleadingly. “Please?” His eyes looked like a puppy dog that wants the sausage on your fork, and she couldn’t resist him. She turned around and heard him gasp.
Chrissy gave it a while and then looked over her shoulder. Timmy was now wanking earnestly with his eyes fixed on her bum. He was muttering ‘beautiful’ under his breath over and over as he did.
She watched the little boy masturbating his big cock and all she could think about was how it would feel in her pussy. She knew that she should put a stop to this now … but her vagina was clenching madly at the sight of it … her pussy needed it.
She turned around and moved right next to the bed so that her sex was inches from Timmy’s head.
“Show me your hands Timmy.” she told him firmly. He dragged his eyes from her groin and looked up at her face. Suddenly he looked guilty as hell.
“Show me your hands or the T-shirt goes back on and I take my chances with your parents.”
Reluctantly he showed them to her. They were mostly clean but there was some red staining under some of the nails.
“You little bugger, you were fingering me while I was asleep, weren’t you?”
“It’s not my fault,” he pleaded. “you’re just so beautiful.” It was a good line and it softened her anger just a little.
“To be fair you seemed to enjoy it. A lot!” he added. “Sorry about the blood though.” He did actually manage to look sorry … and he was right about her enjoying it … and he was still rubbing at his cock which still looked lovely.
“You like my ass, don’t you Timmy?” she asked him.
“Fuck yes.” he replied, and the grin was more lecherous than cheeky now.
“Language Timothy.” she chided before laying down on her front on his bed. “You’ve got ten minutes. Make it count young man.”
She knew it was stupid, and she knew she was probably still a little tipsy from the beer, and she was definitely much more than a little horny. She made herself feel a little better by telling herself that if she didn’t do this he could pretty much ruin her life.
He wasted no time filling his little hands with the cheeks of her arse and she felt her willpower melting away with each soft caress.
Then began to kiss her, working his way slowly down her spine, all the time fondling her trembling, flawless skin.
Surely this little boy couldn’t be going to lick her there?
When he reached her bottom he lavished kisses all over one trembling arse cheek and then the other which gave her goosebumps all over and made her pussy tingle wildly.
Then she felt it. A small hand on each buttock, gently separating them. Her heart was pounding in anticipation as she felt his breath on her previously unmolested little rosebud.
When he licked her crevice, either side of her puckered hole, she was beside herself and wriggled her ass, trying to get him to lick her there, but he continued to tease her for long minutes.
Where did he learn this stuff? she wondered, as he drove her almost crazy with desire.
Then he stopped. She could feel her asshole opening and closing, winking at him, in time with her pussy clenching, as she knew that this schoolboy was seeing her at her most aroused and utterly vulnerable.
And then he kissed it, and she couldn’t help the squeal of delight that escaped her lips.
Chrissy had never played with herself back there and the sensations were a revelation. It was so exquisite that she found herself raising her ass into the air and spreading her legs lewdly to allow him full access to her sensitive little asshole.
His tongue on her ass felt so unutterably gorgeous she found herself whimpering and her eyes welled up with tears of joy.
With his hands free he was able to use them on her drenching pussy and his clever little fingers and his tongue drove her rapidly to a mind-blowing orgasm. She was still reeling from the aftershocks of that when the bed dipped as he knelt behind her and then she felt him place the tip his cock on her still quivering asshole.
Her first reaction was fear, but his tongue had felt so very, very nice, maybe … but would it even fit?
He rubbed himself up and down the crack in her ass, tantalizing her little hole and it felt wonderful. Then something warm and wet dripped into the crack of her ass and realized that he had dribbled on her! Now his glans rubbing on her anus felt lovely beyond words and she pushed back against it, wanting more than anything to feel it inside her.
“Are you sure?” he asked softly, which she thought it was incredibly sweet of him under the circumstances.
“Just be gentle Timmy.” she replied, and pushed back harder. At first it wouldn’t go in, but then she realized that she was bracing herself. When she made an effort to relax just the tip slid in and she gasped aloud at the weird but undeniably lovely sensation.
Timmy was gentle with her and he only fucked her ass with the smallest movements but she was so tight that the friction made it feel incredible to both of them.
Chrissy was nearly cumming and reached between her legs to tease her clit, and that pushed her over the edge. The spasms in her pussy and her ass were so strong that Timmy’s cock was forced right out. He fell across her back and held her quivering body tight while he kissed the back of her neck softly and his cock slid between the cheeks of her ass, inducing further little shocks of pleasure in her.
But amazingly Timmy hadn’t cum yet and Chrissy squealed again as he pushed his teenage erection back into her asshole. It was much easier the second time, and his strokes were deliciously longer and deeper.
She slipped a finger into her vagina and could feel his cock through the thin wall separating her two holes. She felt so incredibly full in a way she never had before but realized that she had always somehow craved.
She was almost overcome with joy when she felt another orgasm begin to build inside her. Then lights washed across the curtains and, soon after, there was the sound of car doors slamming.
“Oh God Timmy, they’re back. You’ve got to stop.” she cried. But there was no stopping him now. He was fucking her like a jack-rabbit, pounding her tight asshole mercilessly and despite herself she loved it, crying out, urging him on.
His pounding forced her face down on the bed and suddenly it was as if his cock was rubbing directly on her clit, only from the back! The orgasm hit her like a explosion and the whole of her body quivered and shook, completely out of control. She heard Timmy groan as her asshole clamped down on his cock time and again, milking the cum from him in great spurts that flooded her ass and felt absolutely delicious.
When he’d finished she wanted nothing more than to just lie in his arms and be held, but she forced herself to jump out of bed. She kissed him briefly on the lips and then scampered back to her room, pausing only to pick up her T-shirt on the way.
She jumped into bed and covered her nakedness with only seconds to spare before she saw the light from the hall through an opening crack in the door.
She prayed with all her heart that they wouldn’t come any closer because they would surely smell the scent of sex which was all over her.
“Come on, she’s asleep.” She heard Laura whisper, and her pounding heart eased a little as the door closed.
She lay in bed exhilarated, a little ashamed, but most of all thrilled at the most wonderful sex of her young life.
They had come so close to getting caught! The repercussions on her life if they had been scared the shit out of poor Chrissy and she resolved that she couldn’t let it happen again.
On the other hand the way it had ended seemed … wrong somehow. She waited until she was sure the Pierces must be asleep and then crept back to Timmy’s room.
He was asleep and she bent over and kissed him softly on the lips. He awoke and smiled up at her, and then he put his arms around her neck and the kisses became more urgent.
She slipped into the bed and they hugged and kissed for long, blissful minutes until she could see his eyelids drooping.
“Goodnight sweet boy, and thank you.” she whispered softly to him and, after a final kiss, she snuck back to her own room.
She lay in her bed and knew she could easily get addicted to young Timmy and his wonderful penis. No, she resolved, she would have to be strong and make her excuses.
Then an idea came into her mind that was so delicious she would just have to do it. Pamela Archer at school. She who thought she was so much better than everybody else and had never let a single boy even kiss her, to the best of Chrissy’s knowledge anyway.
In the morning Chrissy was up early, showered and dressed in the previous day’s clothes, and drinking a glass of juice when the family came down.
“Hi Chrissy. We decided to come home after all, as you can see, well obviously.” Laura said brightly. “Was everything OK?”
“Yes,” Chrissy replied. “we had a lot of fun didn’t we Timmy.” Timmy’s grin was so wide she was a bit surprised that the top of his head didn’t fall off.
“We sure did.” he said happily.
“Can we call on your services again?” she asked Chrissy.
“I’m not sure he needs a babysitter any more.” she told them with a slightly shaky voice. “He’s a big boy now.”
“That’s funny,” said Timmy’s mom. “The last babysitter said exactly the same thing.”
“Oh, is that right?” Chrissy said, trying not to smile.
“But we would prefer for someone to be with him.”
“I’m going to be a bit busy but there’s this very nice girl at school called Pamela Archer, I’ll give you her number. I’m sure she’ll be interested.”
“Thanks Chrissy, that’s very kind of you.” Laura said, and I copied the number from my phone to hers.
“Is it OK is I say goodbye to Timmy?” I asked her. She nodded and I put my arm around his shoulders and drew him a little distance away.
“I have to know Timmy,” I asked him when were were out of earshot. “how did you learn all those … things that you did to me?”
“You’re not my first babysitter,” he told her with a twinkle in his eye. “A lot of them have been very … helpful. But you’re my favourite.” His cheeky grin was back and she couldn’t help but smile. I just bet they have. she thought.
She checked Laura wasn’t looking and gave him a little kiss on the lips.
“I’m sure you’ll just love Pamela Timmy.” she said, and stroked his arm fondly.
I really must remember to look him up in a couple of years, she thought to herself as she walked gingerly away – her bottom was still a little sore.
