babysitter

Three Weeks to Lose his Virginity

Chapter 1 by tid3i3ringer tid3i3ringer

John couldn't believe it.

His mum had won a holiday to Ibiza from a competition off the back of a box of cornflakes. First, she'd told him she wasn't going to take him, which wasn't such a huge shock. The prize was for two and of course she'd take her boyfriend, that arsehole Roger.

But then, instead of having three weeks on his own, she'd asked her old friend emma to come and stay to look after him! At the age of eighteen, he didn't need a bloody babysitter! And who the hell was this emma? He could barely remember her because she'd moved to Dubai with her family five years ago and Mum had stayed in touch with her by mail so he'd not seen her since.

Ironically, he did have some vague memories of emma babysitting him when he was a child, after his father had left them. Apparently she'd been a neighbour and got close to his mum despite their age difference; she was probably only five or so years older than him.

She was in the process of moving back to the UK having divorced her husband and it suited her to have a place to stay for a few weeks and, of course, it suited his mum to curtail any freedom he might have had while she was gone.

It's not like he would have had lots of wild parties. Frankly he didn't really have enough friends to have a party as such. But, like any other healthy eighteen year old boy, he'd been looking forward to having the run of the house. Going out whenever he wanted to. Drinking perhaps. And of course watching mountains of porn.

But now here he was, waiting at Waterloo station, for the person who was going to make the next three weeks hell rather than the potential heaven it could have been. He knew for a fact Mum had talked to emma about the long list of rules to which he had to adhere.

The only upside might be that he had an indistinct memory that emma had been a good-looking girl. Of course at eight, he'd not really understood such things, but, if she were still as hot as he thought she might be, at least he would be able to secretly ogle her while she was here.

"John, is that you?"

John turned to face his oppressor and stopped dead. And then he began to blush, as he did in the presence of any attractive woman. Or in this case in the presence of a very attractive woman indeed.

She was tall, almost as tall as him, with a wide knowing smile and big dark eyes. Her lipstick was a shocking red and she was wearing a blue fitted cardigan and jeans. Her shiny dark brown hair was shoulder-length and her figure was perfect: long lithe legs and, most exciting of all, breasts that were almost too large for her slender body.

Not that John was in any way fussy. As an eighteen year old virgin who had never even had a sniff of a snog, he couldn't afford to be. But he'd decided he was definitely a breast man. While masturbating he would always time his ejaculation to the sight of a big-bosomed centrefold or a busty porn star taking it at both ends.

Which explained why the sight of emma's slightly tanned and extremely impressive cleavage had instantly given him a hard-on. He desperately hoped she wouldn't notice.

"Hello, emma," he mumbled.

"John! Wow, I know it sounds stupid but you've really grown. Look at you!" emma replied happily. "Come here!" she smiled as she stepped forward for a hug.

John awkwardly allowed her hold him, trying to keep his crotch from pressing revealingly into her. Her hair smelt fresh and her breasts felt substantial and firm against his chest. With a slight groan at his loss of control, he stopped holding his hips back and allowed his erection to briefly push against her tummy.

She must have noticed but didn't react beyond a slight twitch of one of her eyebrows.

"I can't believe how much you've changed," she commented as he pulled her suitcase along en route to the taxi rank. "It only feels like yesterday when I was wrestling with you on your mum's sofa!"

The thought of wrestling with emma almost caused John to groan involuntarily again. But he felt embarrassed too. His mum always said what a gorgeous little boy he'd been, usually when she having a go at him for the way he now dressed or for not washing properly. He knew he didn't cut an attractive figure, slightly overweight with greasy black hair and a faceful of zits. He also dressed exclusively in dark heavy goth-like clothing but this was all a way of hiding from the real world and particularly from the very girls with whom he was sexually obsessed. He was sure emma would be remembering that handsome young boy and was disgusted by the ugly teenager he'd become.

Hence despite emma's friendliness, he was brusque, almost surly in his responses to her questions as they travelled home. By the time they got back to the house, he was utterly in love yet at the same time angry with her for being so nice to him. She had obviously sensed his mood as she had stopped trying to engage him in conversation.



At the house, he showed emma to his mum's bedroom which she'd be using for her stay.

"I know it's pretty early but I'm still jet lagged so I'm going to skip supper and go and have a bath and get to bed, John," she said. "You've got school tomorrow so please don't stay up too late," she added.

John could have kicked himself. He was going to spend three whole weeks, with the most gorgeous woman he'd ever met in his life and he'd already pissed her off by being a petulant twat.

He made his way downstairs to the kitchen to have something to eat before settling down in front of the TV, his erection still uncomfortable in his black jeans. He decided to wait until she was asleep before having a wank.

He could hear her moving around in the bathroom upstairs and rubbed his cock through his trousers at the thought of her having a bath. He imagined her big breasts floating in the foam; he imagined her towelling her gorgeous body dry; he imagined her rubbing moisturiser into her long sexy legs. Oh shit, she was so beautiful.

At last he heard the creaks of his mum's bed as she got in and, not long afterwards, the sound of her turning off the lamp.

He waited another few impatient minutes before slipping up to his room to get a porn DVD and an old pair of underpants to mop up any mess. On the way back down, he paused outside her bedroom door. Nothing. She was fast asleep.

Back in the living room, he turned on the TV and forwarded the DVD to his favourite scene where two stunning models give a blowjob to a ridiculously lucky photographer. He'd not realised it before but the girl on the left didn't look too dissimilar to emma. She had black hair but her body was just as lovely although her breasts were even larger, artificially so, he guessed.

At last he pulled out his cock and began to masturbate, imagining that he was getting a two-girl blowjob from emma and a pretty blonde, such as Suzy Simpson from his class.

He was just beginning to speed up, knowing he wouldn't be able to last much longer, when he got the shock of his life.

"John!"

He grabbed the underpants and covered himself reflexively as he turned to see emma standing behind the sofa wearing a white silky gown. She appeared more amused than horrified as she looked up from John's cock to see the blonde on screen swallow a huge penis like it was a lolly.

"Oh shit," he moaned, mortified at being caught and desperately trying to put his dick away. "I'm so sorry."

She smiled as she walked past him to go to the kitchen. "Don't worry!" she giggled. "You're a teenage boy. I'd be amazed if you weren't wanking at least once a day. Don't stop on my account! I only wanted a glass of water."

John didn't know what to do. He'd expected her to be upset. But she seemed to think it was funny. He was trying to remember whether he'd been murmuring her name when she'd walked in. Oh no, how embarrassing. What if she told his mum?

But she'd just looked at the porn like it was the latest Disney cartoon. And she'd actually encouraged him to continue having a wank.

She popped her head around the corner. "John would you like a beer?"

"What! Um, well, I'm not supposed to have one. They're Roger's," he replied in confusion, referring to his mum's boyfriend.

"Don't worry; we'll replace them before they get back." After his amazed pause, she added, "Well, would you like one?"

"Um, yeah, sure, I mean, yes please."

She popped back into the kitchen but was back almost immediately with two cans of beer.

"I think I'll have one too. Budge up then," she ordered as she sat down to his right.

As he took the beer, he realised the underpants were on the floor and his cock was still sticking out of his jeans. He was holding the DVD remote in his left hand and the can of beer in his right.

"I know your mum gave me a big list of things you can't do but, the way I see it, what she doesn't know won't bother her. I spent years looking after you and I've still got a big soft spot for you. I noticed you had a big hard spot for me at the station!" she said nodding at his hard penis.

What's next?

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