Emily's Story Pt. 01

As Emily was ruminating, Tom's frustration was threatening to get the better of him. 'If you prefer, we can forget about any of this,' he said, 'pretend we never had this conversation and I'll see your Dad when he eventually gets back later on tonight.'

'No,' said Emily. Tom's warning was clear. 'I don't want that.'

'Well.'

'It just...'

'You think it's wrong to be naked in front of another person.' He finished her sentence for her.

'That's what Mum and Dad tell me,' said Emily. 'I've never had my clothes off in front of a boy in real life before, let alone a grown man,' she said. She brushed away her hair. 'I'm a good person. I try not to do wrong things.'

'Well I don't think taking your clothes off is such a bad thing to do,' Tom countered. 'In any case, you're doing it to help out your Dad. Does that still make it wrong?'

'I'm not sure,' said Emily. 'It probably does make a difference...' she paused and there was a look of uncertainty in her face, '...and I guess I did say I would do anything,' she finished.

'You did.'

Emily took a deep breath, gathering herself. 'It's just that I didn't think it would be this,' she said.

'I guess not,' said Tom. But he sensed they were getting there now. She had said she was willing to do anything on her Dad's behalf and he'd believed her. It seemed more than likely to him now that she would make good on that. He just needed to be patient. But it would be worth waiting for. She was a good looking girl.

Emily looked out in to the middle distance. 'So let me get this straight first,' she said, 'before I go ahead with any picture.'

'I won't go back on my word, if that's what you're concerned about,' Tom reassured her. 'If you do what I'm asking and keep it secret then I'll let Dennis stay on at the company.'

'Ok,' said Emily. 'So this is what you're going to ask for - you want me to be your girlfriend and in return you'll let Dad keep his job.'

Tom replied in the affirmative. 'But it will be a little different to a normal boyfriend and girlfriend, you see, because we won't tell anybody about it,' he said. 'It's going to be our little secret.'

'I've never had a real boyfriend before,' said Emily. 'What will it be like?'

Tom found her innocence completely intoxicating. He told her she would just have to find out for herself.

'Ok,' said Emily finally. It felt to Tom as if the ice had finally melted.

'Ok,' he said. 'So now we need to take this picture.'

'I know,' said Emily. 'Just give me a minute to close all the curtains.'

At last it looked like it was going to happen. Tom felt his heart thumping and his pulse racing. He wiped sweaty palms on his trouser legs.

Emily got up to shut the living room curtains. It was dark outside and the indoor lights were on brightly so for anybody passing by they would have had a clear view in to the scene being played out in that living room in outer London. Emily went around the room taking great care to ensure there were no cracks left between the drawn curtains. At one moment she thought she could see a funny sort of movement outside a neighbour's house. But when she looked again the night was completely still.

'You promise not to show anyone else this picture?' said Emily, turning back to face Tom.

'Of course,' said Tom.

She stood nervously in the centre of the living room and looked around herself to check again that the curtains were tightly shut.

'And you promise that this is going to mean Dad will keep his job?'

Tom nodded.

Emily paused and took a deep breath. 'I've never taken my clothes off like this before,' she said. 'You have to promise not to laugh.'

Tom grinned in spite of himself. 'Ok, I promise,' he said, and he waited.

'Ok,' said Emily. 'Here goes then...'

She took a final deep breath and then lifted her top upwards over her tummy and above her bra (blue with white spots) and Tom watched as she stretched her arms upwards to pull the material over her head. She let it fall to the floor beside her and brought her hands up to straighten out her hair. Then she looked nervously at Tom but could read nothing into his expression.

'These too?' she asked, slipping her thumbs inside the waist band of her jeans.

Tom indicated for her to go on so she undid the button and unzipped the fly on her trousers. She had to perform quite a wriggle to ease out of them. The denim hugged her hips snugly. Once the jeans were around her thighs she could slide them down more easily. She stood up straight to kick them off her feet, wearing a simple pair of pale-blue panties.

'There,' said Emily, and she hugged herself self-consciously. Tom fished his iphone out of his trouser pocket. 'Nobody sees this except you,' Emily reminded him.

Tom gestured that he agreed and then loaded up his iphone's camera. He lined up Emily on the screen and waited. She obliged by letting her hands drop to her sides. The way she was standing looked kind of awkward. She seemed unsure whether to look at the camera or turn her face away. She ended up staring vacantly into space which gave her eyes a dreamy quality. Tom took the picture.

'Not bad,' he mumbled to himself as he surveyed the result. 'You know, you're a very pretty girl, Emily.'

Emily blushed and smiled in spite of herself as Tom's eyes flicked from the picture on his iphone to the much better sight of the real thing in front of him. But Emily was already reaching to pick up her jeans and put them back on.

'Wait,' said Tom.

'But you've taken the picture now,' she said.

'I'm not sure this will do though.'

'Why not?' Emily asked.

'Well, this picture could have been taken yourself and sent to me,' said Tom. 'I don't think that's enough for what we need.' He could see Emily about to interject but pressed on with his point. 'I know you think this is embarrassing enough but I don't. A picture like this could have gotten into my hands by accident even. If I ever have to show anyone this photo you could still deny any knowledge of having met me.'

'But you said you weren't going to show anyone,' said Emily, disconcerted. 'You promised.'

'Don't worry, I'm not actually going to. I'll keep my promise provided you keep yours. That's how this works,' he explained. Emily nodded to show that she understood. But there was a look of doubt on her face still.

'But you don't think this picture is good enough? I don't know what you mean,' she said.

'I need to know that I have a picture of you that is so incriminating that you'd never want to reveal our secret,' Tom explained, 'and I'm not sure this one is good enough for that.'

'Yes,' said Emily, 'but even if I take off my underwear and you take another one it wouldn't prove anything more.'

'That's true,' said Tom. 'So I think what we need,' he said carefully 'is a picture of you in a position where it is clear that you're with a man.'

'Oh,' said Emily, sounding apprehensive.

'But it's going to involve me having to get undressed too,' said Tom.

'Really?' Emily stroked her hair nervously.

'Why? Don't you want me to?' Tom asked. Emily thought about this.

'Well... it's not so much that I don't want you to,' she said. Inadvertently, her fantasy with Mr Harris popped in to her mind again. She licked her lips. Her mouth felt dry. 'It's just that I'm not sure it's right,' she explained.

'But I think it's only fair since I've made you take off your clothes that I should do the same,' said Tom.

Emily felt herself becoming breathless. This situation was rapidly escalating out of control.

'But isn't that rather naughty?' she said.

'Hmm...' Tom mumbled thoughtfully. 'I guess so,' he said and there was a glint in his eyes as he added, 'but sometimes naughty things are fun to do.'

Emily was shocked at his hedonism. 'I'm still not sure,' she said quietly but Tom had started unbuttoning his white shirt with one hand. His other still held the iphone.

Realising that any further protests would be futile Emily looked away out of embarrassment. She reassured herself with the thought that if it was going to help her Dad then surely it was worth doing these things. Besides, somewhere in the back of her mind that little voice she so often quashed was beginning to speak up to her, telling her how she had always been so curious about a man's body. What was happening to her now was just like her fantasies about Mr Harris. Isn't that something she had always desired? There was a funny taste in the back of her throat.

Tom's shirt lay open and he stood up to slip off his shoes.

'Oh I don't know about this,' said Emily. She was struggling to get the words out now because her mouth was so dry. Tom moved on to unbuckle his belt.

'So you've never seen a man naked before?' he asked.

'No,' said Emily, shaking her head, 'not in real life.'

'Well, you can look,' said Tom. He paused for a moment. 'Now's your chance to see.'

'But I'm embarrassed,' Emily admitted and she had indeed turned scarlet.

'Oh come on, Emily,' Tom coaxed. 'You know you want to.'

The annoying thing was that Tom's voice seemed to be echoing the little voice in her head that was saying exactly the same things.

'Haven't you ever wondered what a man looks like?' Tom asked. Emily shrugged.

'Perhaps sometimes,' she conceded as Tom unbuttoned and unzipped himself. He dropped his trousers and underwear in one motion, revealing himself. Emily was still trying to avert her gaze but now she couldn't help herself and she turned to look at him. Whether she turned to look out of curiosity, or fascination or some other inexplicable motivation, she couldn't be sure. Her eyes immediately fell upon his manhood, semi-erect and much larger than she'd imagined it would be. At first she thought it looked surprisingly silly and yet there it was - that little voice in the back of her head telling her how much she liked it - and it was right.

Her gaze travelled upwards over a body, framed in that crisp white shirt, that appeared firm and mature. Where her own body was full of soft curves, his was surprisingly lean and hard-edged. He looked good, there was no way of getting around that fact. She had to admit to herself that as far as new experiences went, seeing a man in the flesh for the first time wasn't a bad one.

'So what I want you to do is to take hold of me in your hand,' Tom explained. Emily felt herself jolted awake by his instruction. She'd gone in to a reverie taking in his appearance.

'Take hold of your hand?' she said.

'No,' said Tom, shaking his head. He looked pointedly down at himself.

'What? Take hold of... ' Emily didn't finish the sentence but she was looking at Tom's groin, knowing what he had meant.

'That's right,' said Tom. 'Don't tell me you're not curious to know what it feels like to hold?'

'B-but...' Emily stammered, 'but I'm not supposed to.'

'Who says so?'

'My parents told me not to get involved with boys until I'm married.'

'Then you're going to leave me disappointed?' Emily thought for a moment. She could tell this was a veiled threat. Leave this man disappointed and he would go back on his agreement not to fire her Dad from his job.

'No, I'll do it,' she agreed. She surprised even herself with her resolve.

'Good,' said Tom. He breathed out, relieved. He had worried for a moment that it might all fall apart just then when it seemed that things were about to get really good. But Emily still seemed to be on board with this little adventure of theirs.

'But why do you need me too?' she asked.

'You'll see...' said Tom, simply.

She took a couple of steps closer to him. The voice in her head told her she was doing the right thing, that she wanted to touch him anyway so it would be silly to refuse. The voice was growing more prominent as the evening escalated. More and more Emily found she was listening out for it and heeding its advice.

'Ok,' she said.

She took one more step closer so that she was right up in front of him, within reach of his manhood, and she tentatively stretched out her hand towards him. He was growing larger all the time. The size he appeared to be reaching was astonishing. Emily of course had never seen an erection in the flesh before. As her fingers gently closed around him she was immediately taken by how hard he was in her hand. Sure she had seen images of a man's nakedness but in real life it was something else. She never would have imagined a body part undertaking such a transformation -- from the rubbery thing that had dangled between his legs and which she had thought a little silly not long before to this rock hard pylon which she now held tentatively in her right hand. It was an intimidating thing to look at, even more intimidating to hold.

'Mmm, that's good,' said Tom. 'It feels nice to have you holding me.'

'Does it?' Emily blushed. Her eyes flicked up to his face and she could tell that he wasn't lying. There was an expression of pleasure there.

'How does it feel?' Tom asked.

'Hard,' said Emily, 'and big.' Tom smiled.

'Good.'

Tom now brought up his iphone camera again and directed the view down over his front, eyeing up the live image on the phone's screen.

'You need to kneel down,' said Tom, 'so that I can get your face in the picture.'

'Oh, so that's what you were meaning,' said Emily. She hesitated. 'This can never be allowed to be seen by my parents,' she warned, 'or anyone.'

'Don't worry,' said Tom. 'I'll keep it safe.'

She kept hold of his erect cock and knelt down on the floor in front of him as he had instructed. He was a tall man and on her knees the top of her head only came up to his navel.

'I can't believe I'm doing this,' she remarked. 'This is so naughty.'

'Now, look up,' said Tom.

Emily did as he instructed and turned her pretty green eyes upwards to look at the camera. She was breathless and there was a slightly scared look about her. Tom took the picture. It was perfect -- the view from his height enabled him to see down her cleavage as she knelt with her shy little face hiding behind his erection.

'Good,' he said. Emily let go of him and hugged herself timidly, waiting to be told what was in store for her next. For she sensed this wasn't over yet.

Tom sat down and kicked away his trousers from around his ankles. He was entirely naked apart from his white shirt. Emily remained kneeling on the floor in her bra and panties. She was mesmerised by the sight of him and his body.

'You won't show anyone that picture, will you?' she repeated nervously.

'No,' said Tom. 'Not unless you tell anybody about us.'

'I won't. I promise.'

'Good. Then we have an agreement.' Tom reached for his beer and swallowed several mouthfuls. It seemed Emily was content to await her next instruction. She had her arms folded across her front in a protective way.

'So, is that it now?' Emily asked. 'Can I put some clothes back on?'

'Not yet,' said Tom. He paused and shifted his position on the armchair. 'You asked earlier if I wanted you to be my girlfriend.'

'Yes? Is that what you want?'

'Kind of,' he said, 'but not exactly.' He paused thoughtfully. 'I'm looking for something a bit more...' he searched around for the right expression '...grown-up.' There was a mischievous smirk on his face. 'I want us to have a bit of fun together.'

Emily's face was blank but her mind was working feverishly. She felt as if she had realised all along where this was likely to be going. But now she'd backed herself into a corner. It wasn't really an option to pull out now. Maybe that's the way she'd wanted it - to leave herself with no alternative but to go ahead.

'You're going to ask me to be naughty, aren't you?'

'I suppose you could put it like that, yes,' said Tom.

'I knew it,' Emily said. She sighed and despite the warmth of the room she seemed to tremble a little. 'Look, I'm really not so sure about this, you know,' she said.

Tom let out a deep breath and frowned at her. If the game was up now he would be so disappointed. Things had seemed to be on track. But in that moment she looked as hesitant as ever. 'Don't tell me you're going to quit on me now Emily,' he said.

'I didn't say I was quitting,' she said. 'I'm just not sure, that's all. I mean, I'm a virgin. This is a big deal for me.'

Tom paused for a while and thought. How could he talk her into this? The situation was on a knife edge. He felt as if the longer it took the more his chances were reducing. He began with a different strategy.

'Do you ever masturbate?' he asked. Emily blushed.

'Why do you want to know that?' she asked.

'Just tell me.'

'Um... sometimes, I suppose,' she admitted, before adding 'I know it's wrong and I'm not supposed to.'

'Not everybody would say that masturbating is wrong,' said Tom.

'Perhaps,' agreed Emily. 'But for Catholics it is wrong.'

Tom paused. He looked around the room thinking. Then he looked at the young girl sat kneeling before him. 'Have you ever given yourself an orgasm?' he asked. 'You do know what an orgasm is?' he added.

'Yes, of course I do,' said Emily. 'But no, I don't think I've ever had one,' she said. 'I guess I've probably come close a few times but never quite managed it.' Tom thought about this for a moment and then shrugged.

'Do you know much about a man's orgasm?'

'I know what happens, if that's what you mean.'

Tom nodded. 'Do you think you could manage to make a man have an orgasm?' he asked.

'I don't know,' Emily said. 'I mean, I wouldn't know how to. I wouldn't know what to do.'

'Perhaps I could show you,' Tom suggested.

There was a protracted silence. The question lingered in the air. Emily's mind was whirling. 'Is that what you want?' she asked. Tom nodded.

Her face was indecipherable as she thought about this. That little voice was not so little anymore and it was making itself heard quite clearly now. It was uncanny how closely this scene was playing out to her own previous sexual fantasies. An older man, attractive and confident, someone with experience, someone who knew what they were doing -- this was so often what she had imagined in her private fantasies and this was exactly the sort of man she had in front of her now. Learning about her sexuality with someone strong and masterful, having him teach her and instruct her in what to do, this was just what she had been looking for, wasn't it?

But these fantasies of hers - that was all they were - fantasies. They were safer when they weren't real. She wasn't sure she was ready for the real thing just yet. But then, was she really going to turn back now and let her Dad lose his job? That would be the consequence of denying him now. Besides, she'd come so far. There was no other choice really.

'We've come this far I suppose,' she said at last with a big breath.

Tom realised he had been holding his breath and gripping the armchair with his fingers. He relaxed a little.

As she thought about what was in store for her what Emily was beginning to realise was that part of her enjoyed the idea of finding out how to bring pleasure to a man - and not just any man. This man was the boss of his Dad's company. He was rich, powerful and successful. But more than that he was attractive. He had probably been with many girls and surely all of them would have been older and more experienced than her. Yet now he wanted to be with her. Emily had to concede that she found his desire for her exciting.

'So what do you want me to do first?' she asked as she shuffled closer to Tom.

'I take it you know what a blowjob is?' Tom assumed.

Hearing him say that word sent a chill through Emily from top to bottom -- a feeling of anticipation mingled with intense trepidation.

'Yes, of course,' said Emily. 'At least I have an idea of what's involved.' She hesitated. 'But of course I've never done anything like it.' She shivered. Was it cold or was it just the nerves? Or excitement perhaps? 'I'm not sure I'd be any good,' she said.