Spencer 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 ten 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 ten 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.
“Spencer, is that you?”
Spencer 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 Spencer 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.
“Spencer! 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.
Spencer 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 Spencer 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, Spencer,” she said. “You’ve got school tomorrow so please don’t stay up too late,” she added.
Spencer 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.
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 Spencer’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.”
Spencer 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. “Spencer 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.
“Oh, I’m so sorry…” he began.
“Don’t worry; it’s really flattering that I had that effect on you! I know I must seem like an old lady to you but I’d like to be your friend, Spencer.”
“Oh, no Emma. You’re the most gorgeous woman ever!” he replied vehemently.
“Really? What about all the pretty young things at your school? Aren’t they much more beautiful than me?” she teased.
“Oh, no. Really, I’ve never met anyone as beautiful as you.”
“Spencer, you’re a gentleman. That’s a lovely thing to say. Thanks,” she said.
After a pause she added, “Go on then, keep going, you’re missing a good bit,” gesturing to the screen on which the man was now fucking his dark-haired co-star up her arse while the blonde lay underneath them licking his balls.
His cock twitched. Breathing heavily he moved his hand towards it before realising he was still holding the beer.
“Here,” Emma said, “Let me do that for you.”
He held out the beer for her but she just laughed. “No, silly. Not that. This,” she added as her cool right hand gently clasped his hot aching erection.
“Ohhhh,” Spencer moaned in disbelief as she began to slowly and gently masturbate him. He noticed that the varnish on her perfectly manicured nails matched her lipstick.
“Maybe I should take that beer after all,” Emma suggested as he almost dropped it. “Don’t worry I won’t stop!” she said as she took it from him.
“Oh, Emma,” Spencer murmured inarticulately.
“You know it’s funny,” she said. “The number of times I saw your cock when you were a boy in the bath or while you were getting changed. I never thought that one day I’d be wanking it and that it would grow into such a big one.”
“Really?” Spencer was surprised.
“Oh, yes, darling. You’re not small at all. I’ve seen a lot of cocks and yours is one of the biggest.”
“Wow, thanks!” he exclaimed.
“Pay attention to the screen. Look, that blonde one’s licking his cock again, after it’s been up the other one’s bum as well. What a dirty slut!”
Listening to Emma talk so explicitly, Spencer desperately bucked his hips trying to get her to move her hand faster but she let go of him.
“Ah, ah, ah!” she warned musically. “Slow down, lover.” Bewitched, he nodded and she started again.
“So which one do you prefer – the blonde or the dark one, Spencer?”
“The dark one,” he replied as they watched her lick her colleague’s pussy.
“Why her? Isn’t the blonde one prettier?” Her voice was honeyed and smooth. And highly seductive.
“I love her boobs,” he grunted in reply.
“Oh, you like big boobs then? Even unnatural ones like hers? They wouldn’t feel very nice, I think.” Emma was smiling her worldly smile again.
“I don’t know. I’ve never touched anyone’s boobs. They just look so lovely,” he was almost hysterical in his need to come now but Emma just kept slowly stroking him, keeping him expertly on the edge of orgasm.
“Really? You’ve never touched breasts before? You poor thing.” She licked her lips. “Would you like to touch mine?”
Spencer hadn’t realised he could be any more excited than he already was. But as he nodded wordlessly and Emma let go of his cock to unhurriedly open her gown from the waist up, he began to understand just how much further there was to go.
He watched entranced as, first, the light brown slopes of her upper breasts came into view. Then, she carefully pulled down her gown until the very tops of her chocolate brown aureoles peeped over the white silk.
Finally he moaned with lust as she pulled it open all the way exposing her stiff dark nipples and the weighty underside of her large yet firm breasts. They were golden and lightly tanned like her face.
“You can touch them, Spencer,” Emma breathed as she reached out to masturbate him again.
He reached out and allowed her bullet-hard nipples to touch the palms of his hands teasingly before grabbing hold of her boobs and squeezing powerfully.
“Spencer! I know you’re excited, sweetie, but more gently please,” she exclaimed. “Yes that’s better, there’s no hurry you’ve got plenty of time over the next few weeks to touch them,” she added as he began to more tenderly fondle her considerable bosom.
“They’re so soft but at the same time so firm, I mean they don’t sag at all,” he expressed in wonder.
“Thank you, Spencer.”
“No really, thank you, Emma. I mean I can’t believe you’re giving me a handjob!”
“It’s fine, darling. You can’t walk around with an erection all the time. It can’t be very comfortable and I’m sure it’s not good for you to repress all that sexual tension. Do you get hard when you’re talking to the girls at school?” Emma asked.
“Sometimes,” he nodded. “Although I hardly ever talk to any girls. Please, Emma, can I come now?”
“Be patient, lover,” she gently chided although she did start to speed up her hand perhaps realising that he wasn’t going to explode immediately. “I’ll make you a deal, Spencer. Over the next few weeks I’ll do my best to help you become more confident with girls with the aim of maybe finding a girl at school who could do this for you.”
“Oh, Emma. That would be great,” he said. “But you’ll do this again for me? Please?” he added, secretly thinking that the odds were low that anyone else would ever do this.
“Spencer, I promise that I’ll give you relief if you have an erection in my presence. After all, it really isn’t a hassle for me to just move my hand up and down on your cock for a few minutes while you play with my tits. And how could I not do it when it gives you so much pleasure,” she said fondly. “But I’m serious about getting you into shape to find someone else to do this for you. I’m only here for three weeks and I’d hate for you to go without after I’m gone.”
“OK, OK, anything you want. Please just a little quicker – I’m so close,” he pleaded.
“You have to promise to do everything I say though. Promise?”
“Yes, oh, yes. I promise. I promise,” he shrieked.
“OK then. You can come on my boobs.” And with that Emma knelt in front of him and began to masturbate him properly for the first time while her left hand cupped his heavy testicles.
Within seconds he began repeatedly shooting strings of sticky cum all over her considerable boobs, while shouting in pleasure.
“Gosh, Spencer!” Emma exclaimed. “What a lot of spunk. My poor boobs are absolutely covered. I think I might need another bath.”
Spencer collapsed back on the sofa, marvelling at what had just happened. Surely this must be a dream? Things like this just didn’t happen to boys like him.
The next morning Spencer woke, as he did most mornings, with an erection. He began to masturbate languorously before stopping wide-eyed, recalling the previous evening. Had it been a dream? Had he really come over Emma’s breasts the night before?
He remembered walking upstairs with her, unable to take his eyes from her spunky tits, while she insisted that they go to their separate bedrooms despite his begging her to masturbate him again.
If it hadn’t been a dream then he also remembered her promising to ‘sort him out’ in the morning before he went to school. In which case…
He jumped out of bed in excitement, his cock poking out through his pyjama fly.
There was a knock on the door and Emma walked in, already dressed in t-shirt and jeans. “Come on, you’re going to be late,” she said as she pulled open the curtains.
As light flooded the room, Spencer realised that if it had just been a dream then it probably wasn’t a great idea to be standing open-mouthed in the middle of his room with his cock sticking out.
But by this time Emma had already turned around and seen his erection.
“Well, I suppose that’s no surprise,” she said as she grabbed hold of his cock and led back him to the bed. “OK, I’m going to do you quickly now because I want you to have a shower before you go to school and we haven’t got much time,” she added as she began to toss him off again. “But I really want you to learn to control yourself so, when you do manage to find yourself a girl, you can show her a good time. Is that OK?”
“Oh, fuck, yes, Emma!” he gasped as her hand sped up and down his dick. He reached out and began manhandling her breasts through her t-shirt and bra.
“And I mean what I said about the shower. You won’t get a girl if you’re not clean. You really do whiff a bit. Although that’s no surprise. It smells disgusting in here too. While you’re at school, I’ll clean your room.”
“Oh, shit, that feels so good, Emma. Um, about the room…” he began.
“Don’t worry. I’ll treat your porn sensitively,” she added, smiling at his concerned expression.
He slid his hand under her t-shirt to continue pawing at her breasts.
“Careful, dear. That bra is delicate and expensive. I need to teach you to be a bit more gentle as well as patient, I think.” Her hand began to blur on his cock as she increased her pace once again.
“Here it comes!” Emma declared as, with a triumphant groan, Spencer came copiously over her hands and over his bedding.
After making sure he was fully drained, Emma added, “Right go and have that shower, darling. I’ll find some half-decent clothes for you to wear.”
Spencer was fantasising about Emma. He was imagining her licking and sucking his cock, hungrily begging for him to come in her mouth. The thought of those soft red lips sliding up and down his rigid pole and those dark perceptive eyes, gazing up at him while she smiled around a mouthful of his cock, had him rock hard again.
Which, he realised as the school bell rang, was a bit of a problem as he was in a class and everyone around him was leaving.
Emma had dressed him very differently in a white t-shirt and blue jeans and he’d already had a few comments at school today, all of them surprisingly positive. She’d also promised to take him shopping for more clothes as well as a proper haircut that weekend. She’d also tantalisingly hinted that, if he were clean, she might consider using more than her hands on him that evening; hence the flavour of his fantasy today.
He smiled once more at the thought of her hot sucking mouth. He heard a giggle and realised he was staring at Suzy Simpson and that she was smiling back, although he couldn’t tell whether she was laughing at him or whether she was being uncharacteristically friendly.
Suzy was stunning, with a statuesque and curvaceous figure, a surprisingly sweet pretty face and spiky blonde hair. She was popular with everyone at school, slightly rebellious but still academically able and the favourite object of Spencer’s fantasies before Emma had arrived. And she’d had several boyfriends and was rumoured to have gone all the way with them.
Suzy and two of her friends walked away, still giggling, with a few glances back over their shoulders. He realised they weren’t just looking at his face and worked out that the lump in his trousers was more than obvious.
Three Weeks to Lose his Virginity Ch. 01
Spencer couldn’t believe it.