tagFirst TimeThree Weeks to Lose his Virginity Ch. 02

Three Weeks to Lose his Virginity Ch. 02


Spencer was desperate for school to finish.

His mum's friend Emma had been staying with him for the last week while his mum was on holiday.

He could barely remember Emma from his childhood and was amazed to find when he met her that she was a stunningly attractive lady in her late-twenties, a walking fantasy with dark eyes, a wide sexy mouth, perfect arse, long legs and huge firm breasts.

And not only that, she was seriously fond of him. So much so in fact that she'd resolved to make him happier by boosting his confidence in general and with girls in particular.

Like most of his male classmates, Spencer thought about little other than women. He spent as much of his time as possible watching porn and masturbating. But, in the real world, he wasn't brave enough to even talk to the girls in his class let alone ask one out on a date so he had no real chance of actually fulfilling any of his varied and intricate fantasies.

At least until Emma arrived.

She'd decided he needed a full makeover. She'd bought him new clothes and got him an expensive haircut. She'd found he had an unused set of weights and insisted he work out every day. She'd made sure he washed properly and kept his room reasonably tidy and clean. She made sure he ate healthily and generally looked after himself.

And there was no doubt he felt a lot better for it. Already he was fitter and stronger. His complexion had improved. He stood taller and felt a lot better about himself.

Although that might also be because of her methods to boost his confidence. When she'd masturbated him for the first time she'd explained that to her, giving him so much pleasure was worth a little manual effort on her part. And then when she began sucking his cock, she'd confessed that she'd been waiting for his sexual endurance to increase before doing so.

This morning he had almost missed his bus for school after it had taken Emma almost half an hour to make him come despite her best efforts with her mouth, breasts and hands.

"Well, I think we can safely say you've got some real stamina now, darling!" she'd said as he'd dressed hurriedly, having ejaculated down her throat. "I think we can maybe expand your education when you get home tonight. How would you like to see my pussy?"

In the end she'd had to physically push him out of the front door so he wouldn't be late for school.

So far, although she often walked around the house in nothing but a thong, she'd not let him touch or even see her pussy. Also, despite giving him snogs, handjobs, blowjobs and tit-wanks she hadn't allowed him to lick or suck her breasts at all, telling him she didn't want to be distracted from the task at hand. Which was why he was impatiently waiting now for his final lesson of the day to finish so he could get home and see his first real live cunt.

As soon as the bell rang, Spencer gathered his books and sprinted out into the corridor. Within two steps he ran straight into another student and sent her sprawling before landing heavily on top of her.

"I'm so sorry..." he started before realising he was looking down an immense valley of soft creamy bosom, only inches away from his face. He stopped dead with his mouth wide open.

After a few seconds, he heard from in front of him, "Um, hello. Are you having fun down there?"

"Oh, shit, I'm so sorry," a red-faced Spencer mumbled as he looked up into Suzy Simpson's clear blue eyes. He stood and helped her up. "I wasn't looking where I was going," he added before pausing to take a deep breath and trying to imagine what Emma would advise him to do in this situation.

He looked into her eyes with a confidence he didn't really feel and smiled, "Are you OK?"

"Yeah, I'm fine," she replied as he picked up her bag and bent to collect up his own books which were now strewn across the corridor.

"So anyway, Spencer," she said having adjusted her clothing. "Jenny and I were trying to work out when you're going to be on the TV," she said cryptically as he gathered them up.

Spencer looked up bemused. "What?"

"You look like you've been on some sort of makeover programme. Have you?" she asked with a smile.

"No!" he laughed. His heart beating he continued, "Why, do you think it's an improvement?"

She looked him up and down pointedly, "A lot better, I'd say." He hadn't realised just how lovely her eyes were.

They began to walk out of school.

Suzy cleared her throat. "A few of us are off to McDs if you want to, you know..."

"Oh, shit, sorry but I can't; I have to go," he stammered in confusion.

"Oh. OK," she said. "Going to see your girlfriend?" she added with a slight edge to her tone.

"Well, yes, kind of." Spencer almost ran from her as went to his bus-stop, in the opposite direction to McDonalds.

On the bus, he thought about what had just happened. The gorgeous Suzy Simpson had spoken to him! She'd even complimented him, he thought. And the most amazing thing of all was that she's invited him to hang out with her and her popular friends.

And, oh fuck, he'd completely screwed it up. Of course, he should have gone with her. And now she thought he had a girlfriend. Oh, shit, shit, shit, shit!

When he told Emma however about that had happened she was a lot more positive.

"So, it looks like the fish is interested in the bait at least," she laughed as she affectionately squeezed his crotch.

"But she probably hates me now," Spencer moaned.

"Oh, I'm not so sure. It's quite possible you've done exactly the right thing. She's now intrigued. She sounds like she's used to getting whatever she wants so I think playing it cool might just have piqued her interest. Why didn't you go with her, by the way? Were you a bit worried about her friends?"

"Er, no. It wasn't that. It's just that I was desperate to some and home and see your, you know, pussy," he said coming to a halt.

Emma laughed. "And are you still keen to see it?" she teased.

"Oh, fuck, yes, please!"

"OK. Except, there are a few rules first, young man," she said as she led him up to his bedroom.

She sat down on the bed. "Oh, I see you've already got a hard-on. Take you cock out and I'll give you a wank while we talk."

Emma discarded her jeans, top and bra so she was left in a tiny white g-string. By the time she came and sat beside him on the bed, Spencer was already naked, lying back on his pillows with his erection waving in the air. She cupped his balls with one hand while gracefully masturbating him with the other.

"Spencer, I know this might come as a bit of a disappointment to you but I'm not going to let you shag me, dear."

Spencer who had been dreaming of exactly that was thunderstruck. "But, but, I thought you said you were going to show me your pussy," he complained.

"Oh, darling, I am going to show it to you and I'm going to let you touch it and kiss it but I don't want to take your virginity."

Spencer was so upset that he stopped fondling her considerable breasts.

"Oh, Spencer, darling, don't look so disconsolate. I really do want to fuck you. It's just that your first time shouldn't be with me. It should be with a girl your own age like Suzy. I don't want you to look back and regret the way you popped your cherry."

"Emma, I can sincerely tell you that if I lost it to you then I would never ever regret it."

"Well then maybe I might regret it," she replied. "I've done things with you that I would never have considered with any other 18 year old. And that's because I have a real affection for you that originated from when you were just a boy. But I think taking your virginity would be a step too far. Remember I'm trying to set you up with real sexual confidence for life. I promise we will fuck one day and I promise I'll make it absolutely amazing for you. But not yet, my dear."

Spencer began to tweak her nipples while he considered what she said. Oddly, her slow methodical wanking helped his deliberation rather than hindered it.

"Emma, you are the by the far the most beautiful woman I have ever seen let alone met. Of course I want to fuck you but I'm so grateful to you for all you've done for me that I'll do whatever you want. But promise me one thing."

"What, love?"

"If I can lose my virginity to Suzy before you go that you'll let me have you."

Emma smiled at him. "Oh, Spencer. I really hope you nail her. Because I promise if you do I'll let you inside me like a shot!"

She lay down beside him and slid her tongue into her mouth. They kissed passionately before Emma moved down to gently suck his erection.

After a while, Emma came up for breath before continuing. "That's why I haven't let you see my cunt yet or even let you suck my nipples. You see you had to develop some restraint otherwise I feared you'd lose control and fuck me. And that I'd get so turned on that I'd let you. I trust you, Spencer. I know now that even if I become aroused you won't take advantage of me."

Spencer didn't say anything but maintained eye contact while he pulled her up and bent his head down to kiss her right breast. Encouraged by her moan, he began to lick and suck both of her tits, marvelling at the feel of her hard nipples against his tongue.

"Oh, yes, Spencer. That's lovely. Oh yes, yes, yes. That's it. Oh, a bit harder. And bite gently. That's it!"

For the next twenty minutes Emma, in between groans of delight, gave him advice on his technique until she couldn't take it any more.

"Fuck, Spencer. You're going to make a lot of women very happy with your tongue. I'm dripping wet, darling. See."

Spencer gasped as she stood up and slowly peeled her damp thong down exposing a narrow line of dark hair pointing down to the hidden delights of her pussy.

Emma lay down beside him and opened her legs. "Come on then, dear. Come and have a look."

Her pussy was beautiful. Spencer lay on the bed, his face inches from the long pink lips, glistening with her juices. The smell was surprisingly sweet and made him want to kiss her cunt which is exactly what he did.

"Oh, Emma. It's gorgeous!" he exclaimed in wonder, marvelling at the heady taste.

Emma laughed with pleasure until he slowly slid his finger up and down her gash, further working open her pussy lips. Gradually he inserted a finger inside, eliciting a deep moan of joy from her.

He slid his finger in and out a few times before moving up to her clit which he gently teased with the very tip of his index finger.

"Oh, fuck , yes, Spencer!"

He slid another finger back in and began to inexpertly but enthusiastically masturbate Emma until within just a few minutes, she tensed her entire body before screaming out an orgasm.

"Spencer, that was fucking fantastic, darling. I'm so turned on!" she exclaimed after she'd calmed down.

"Emma, can I lick you properly now?" Spencer asked, thrilled at giving pleasure back to Emma.

"Oh, if you must," she giggled as he took one lingering lick, starting at the pretty brown rosebud of her arsehole, slowly parting her wet pink lips with his eager tongue and ending at her excited red clitoris.

"Oh, that's it, Spencer. Hmmm, yes. Harder, harder. Don't stop, darling..."

Over the next hour Emma instructed Spencer on satisfying her with his fingers and tongue, coming repeatedly until eventually they finished off with a satisfying sixty-nine with Emma on top, desperately trying to keep his cock in her mouth while she orgasmed uncontrollably.

"Oh, Spencer," Emma sighed, "you are going to make a lot of girls very happy with that tongue of yours. You're a natural pussy-licker, darling. I really think the next few days are going to be a lot of fun!"


And they were.

Over the next week, Spencer spent as much time as possible with his face buried in Emma's pussy and his cock in her mouth. He learnt exactly how she liked him to gently lick her lips; he learnt that flicking his tongue over her clit drove her crazy; he learnt that sliding a finger into her arsehole and two into her cunt as if she were a bowling ball brought her to orgasm within seconds.

In short he learnt all about he could about her body, almost literally inside-out.

Not that there weren't a few difficult moments.

On more than one occasion he had found himself kneeling between Emma's legs, his pounding erection in hand, while she lay there, her legs apart, looking up at him with longing.

He knew that if he'd wanted to she would have welcomed inside her, desperate to be fucked. But he'd kept remembering his promise not to shag her, knowing that it would be fantastic but that the next day there was a good chance she wouldn't let him near her.

And there was no way he could possibly give this up. He didn't know what it would be like to slide his cock in and out of her wet pink pussy but surely it couldn't be as amazing as the feeling of her mouth on him, slurping like a suction pump. Could it?

In any case, every time he'd been close to giving in and thrusting his dick into her, he'd managed to hold back and distract himself with another delightful part of her body instead. And every time she'd thanked him passionately.

Apart from their marathon sessions in bed, Emma had also continued coaching him on how to interact with women in more mundane circumstances with a particular emphasis on the seduction of Suzy Simpson.

The day after he'd blown Suzy out, he had gone to school expecting her to give him the cold shoulder. And during the one lesson they'd shared that morning, she had indeed avoided eye contact.

But when he'd passed her in the corridor and given her a big assured smile, she'd looked startled but had smiled back at him which was an encouraging start.

That evening, as they ate a meal in front of the television in their underwear, Emma had advised him to approach Suzy the next day more directly which he'd reluctantly promised to do.

He hadn't seen her until the next afternoon and when he had he'd almost balked as she'd been talking to several of her equally glamorous friends in the senior common room. But, heart pounding, he'd remembered his promise and had walked straight up to her.

"Hi, Suzy. Can I have a quick word?" he'd asked with a confident grin.

Although Suzy's friends had looked at him in amazement, he'd just waited patiently despite wanting to run away. Sitting with her were Suzy's best friends Anna, a willowy redhead with freckles and startlingly green eyes, and Jenny, a tiny half-Chinese half-European girl with a doll-like face. Both were stunning and previously he would have been ridiculously anxious to be in their company.

"Oh, hi, Spencer. OK," Suzy had replied with a slight blush but, with a quick giggle for her friends, she had followed him over to another table. Spencer gave Anna and Jenny a friendly smile as he followed her over.

After a deep calming breath, Spencer had continued. "Suzy, I just wanted to apologise for running away so rudely the other day. I really would have loved to have spent some time with you but it's just that I'd promised to get home. You see my mum's away and one of her friends is staying and she was cooking for me; I didn't want to let her down," he'd dissembled.

"Oh, well, that's OK," Suzy had mumbled. "I mean it wasn't that important."

"Well to be honest, Suzy, if I'd thought I could have just called Emma and let her know I was going to be late. It's just that I was a bit flustered. I'm not used to talking to such a beautiful girl." Spencer had held his breath at this point. Emma's considered but risky strategy was to mix some disarming honesty with a little outrageous flattery.

Suzy had blushed charmingly. "Oh Spencer! I mean, thanks. That's OK."

Taking his chance, Spencer had ploughed on. "In fact I was wondering if I could make up for it by taking you out on Friday? How about going to see the latest Julia Roberts film?" Emma had advised that a chick flick would be the best bet.

"I, um, well, I don't know..." she'd replied.

"Unless you're doing anything else of course?" he'd carried on, trying to keep a note of desperation out of his voice.

"Well I was going to go and see it on Sunday with Anna and Jenny but I suppose..."

"Great! I'll meet you at the cinema at 8:00. I have to go now but I'm really looking forward to it." He'd given her another smile and then walked away to his next lesson, leaving her giggling once more with her friends.

When Spencer had told Emma all about the encounter, she'd been delighted. "Spencer! You did brilliantly. Sounds like you took control. Girls love that!" she'd told him as she'd prepared to give him a tit-wank.

"I couldn't believe it," he'd confessed as he played with her stiffening nipples. "It was a lot easier than I thought it would be. I really didn't think she'd say yes." He'd groaned as Emma flicked her tongue over his glans.

After a few minutes of oral ecstasy, Emma continued. "Darling, I know you see Suzy as a sophisticated young woman, experienced in the ways of love and sex but she's only eighteen. Yes, she may have had fucked a few boyfriends but you've had more sex in the last couple of weeks than she will ever have had. Remember darling, you're in charge! She'll love it!" she'd said firmly before adding, "Now let's see if you can cover my big boobies with your spunk!" Spencer moaned as Emma took him once more to heaven.

So all-in-all, Spencer had had a great week. Emma had continued his sexual education and Suzy had agreed to go out with him.

But as Friday had approached he'd begun to feel more and more nervous. Emma had done her best to calm him down using her body in various pleasingly distracting ways.

"Darling, you know what to do tonight. Just be yourself. You're a witty and charming boy. Stay calm and enjoy yourself. Don't expect too much. If you're lucky you might get a snog. Anything else would be a bonus," she'd counselled. "Oh, and I'll have a treat waiting for you tonight. Something a bit special we haven't tried before."

Despite Emma's intriguing promise, he got to the cinema twenty minutes early and nervously waited for Suzy, half-expecting her to stand him up. So he jumped when he heard her voice behind him.

"Hi, Spencer."

He turned and stopped dead. She looked gorgeous. Her blonde hair was carefully styled into a casual spikiness. Her smiling blue eyes were set off by perhaps a touch too much make-up but still sparkled like sapphires. She was wearing a light blue halter neck top that gave her a deep cleavage and barely constrained her substantial breasts, a low-cut dark blue cardigan, a white mini-skirt and high-heeled white boots.

"Shit, Suzy. You look stunning."

Suzy flashed him a heart-stopping smile. "Thanks, Spencer. You scrub up pretty well yourself."

"Oh, thanks," he replied. Emma had carefully chosen his outfit but he knew he wasn't anywhere near as attractive as Suzy.

"I've bought the tickets; shall we?" He offered her his arm. She took it with another dazzling smile and once more his heart skipped a beat.

The evening went well. The film, although not to his taste, had been romantic yet funny and Suzy had certainly seemed to really enjoy it.

Spencer had put his arm around her and she'd leant her head against his shoulder. Even though he was trying to play it cool he'd developed an uncomfortable erection, possibly because he couldn't help but recall the blowjob he'd got from Emma at this very screen.

Still, he'd managed to control himself and they had left together arm-in-arm laughing.

As they wandered aimlessly away from the cinema, Spencer turned to Suzy before asking "Would you like to go for a drink?"

Suzy considered briefly. "OK. I have to be home by midnight but maybe just a couple."

Spencer thanked his lucky stars before taking them to the wine bar Emma had suggested.

"Are you sure Spencer," Suzy asked. "It's really expensive in here."

"Of course, my treat," he'd promised grandly, silently thanking Emma for the 'totty allowance' she'd given him.

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