Catching the signal from one of her friends, Angela brushed her skirt, took a deep breath and walked towards where he was sitting. Their first day of work experience, at barely 16, and she was playing out some stupid dare from a girl in the same class. Here she was in an all-grown-up office on Monday morning, dressed primly in a short black pencil skirt that was a little too tight across her blossoming hips and a meant-to-be white school shirt in place of a blouse. Faint ink stains on the cuffs. Shirts and blouses weren’t really her thing. At least she’d had the sense to wear a white t-shirt bra, instead of the neon lacy numbers she usually favoured, even if her perky breasts did feel solemnly squashed beneath this humourless attire.
“I can get any man I want,” she’d boasted proudly on the Friday before. A statement which seemed full of teenage conviction, without any evidence to support this outlandish claim. She’d not even had sex yet, though many girls in her year had claimed they had. She wasn’t sure if they were being entirely truthful or if it was all part of the showing off thing that happened at school. Janie had told her that it was messy and hot, and that you didn’t feel all that good afterwards, and that sometimes it hurt but you weren’t meant to say anything because that meant you were some moany old hag that no boy would ever want to be with. It all sounded very unappealing if she were entirely honest with herself; why she had to blurt out some wild harlot claim just to enjoy the fleeting glance from Claire, looking over her with a wondering expression that was in part approving of this attitude and in part disbelieving scorn, she had no idea.
All of this rushed through her mind in the couple of moments it took to somewhat successfully hobble over to where the manager of the office was sat. An imposing figure, he had a face that was a little too good-looking for a man of his age, in her opinion. Men were meant to get fat and ugly when they were old, weren’t they? He must be at least… 40. Hmm. His navy blue suit was cut through with a faint white pinstripe, his hand pressed to his temple, as he stared at his screen in concentration, revealing a light coloured shirt beneath and a sparkling cuff link. Very smart.
“Ahem,” she muttered, timidly. Were all office workers so boring? She didn’t know how she would ever stand such a dreary job involving connections between piled high reams of paper and insistently bright screens.
He must not have heard her. Very aware that Claire, who was on this work experience with her, was watching, she put out her fingers to lightly brush his arm. He nearly shot out of his skin.
“I’m very sorry, sir, but I think there’s a problem with my machine. It’s not booting up properly.”
“Very well, I’ll come over in a second to have a look for you.”
His eyes seemed to linger on hers a moment longer than they strictly should, then they reconnected with his boring screen once again.
Relieved the first communication was over, she all but ran back to the group of desks where Claire was trying and failing to look like she was concentrating on her work.
“So? Is that your great plan then? That was pathetic,” hissed Claire, ducking her head behind the screen looking every inch the rebellious schoolgirl.
“Give me time, I know what I’m doing.” She hoped she looked and sounded more convincing than she felt. Feeling resentful towards Claire, who she couldn’t even really describe as a friend, and nervous in her new surroundings, she was almost lost in her sullen thoughts when she felt a hand come to rest on her shoulder.
“So, what’s going on here then?”
She almost fainted.
She turned her face up to where Boss stood over her, looking at her with what she knew he imagined to be a kindly face, but instead it was coming off as a “why are you girls in my office interrupting my workflow, I regret ever agreeing to take on work experience kids” kinda face.
“Sorry, sir, it just won’t turn on,” she replied, hoping she was expressing a more apologetic face than she felt. He seemed to realise her ploy though, as his eyes took on a softened look with the realisation.
“I see. It would help if you pressed the power button, silly girl.”
“Ahh… ok thanks. I’m not very good with computers.”
“It’s not a problem. How about we go over some of the basics at the end of the day?”
He was pretty openly appraising her now, his eyes seeming to wish they had x-ray vision as they gazed at her chest, then lower down, to the curve of her ass on the chair.
He strode off, in that way men in authority do, and she snuck a peek at her friend. As was to be expected, Claire was struggling to disguise her incandescent envy.
5pm took an absolute age to roll around. How did people put up with working so long in the day! The last five minutes of the day felt like an hour, and Boss had retired behind the door of his office at the end of the room sometime mid afternoon.
Claire said her goodbyes, her eyes conveying her curiosity about what was going to happen as well as some dim hope that all would be recollected to her in the morning. Angela stood, brushed her skirt again as she was prone to do when nervous, and tried to prepare herself for the long walk over to a mysterious adventure. She hoped. She thought she hoped.
What was she even doing!
She was at the Boss’ office door now; she didn’t remember beginning to walk over. Well there was no point shying away now, she’d come this far. She raised her hand, but just as she was about to knock, the door swung open.
“Come in, I’ve been waiting for you.”
Eyes to the floor and flushed red, she shuffled inside the office. It was clear that this was a Boss’ office; a large desk stood in pride of place overseeing matters and one wall was stacked full with folders and binders and everything that was ever office-like in the history of the world. Her head turned slowly upwards as she found herself before the imposing desk, and Boss walked around her to sit in his throne. Well, that’s what it seemed like in her head, anyway. Sumptuously padded leather with velvet covered arm rests. The contrast in materials made something about her ache, but she wasn’t quite sure what.
There he sat, and steepled his fingers, in that way that office bosses have a habit of doing. Perhaps it gives them thinking time, or it’s to ward off attackers. Her mind was quite evidently refusing to admit the reality of the situation here.
“You’re a pretty girl. I know you’ve been looking over at me today. Someone discovering their naughty side, are we?”
Oh god. He’d noticed then. It was true, she’d developed something of an obsession with his handsome (but still old) face even in the short space of today. Something about the fact he was so much older than her. Perhaps he could teach her how to enjoy things. Things she wasn’t sure she’d enjoy otherwise. Things she didn’t know much about.
“Um, yes sir. I think you’re quite handsome.”
He laughed then; a full on laugh, the loudness of which was shocking in the small room empty but for the pair of them, alone after hours. She tried out a smile; it felt ok so she kept it there.
“For my age, you mean? Yes, I suppose I am quite a bit older than you. I’ve always had a thing for younger girls though. You’re so… eager to please. Supple and flexible. Willing to learn the right ways to behave.”
The right ways? What did he possibly mean by that?
It couldn’t have been entirely accidental that his eyes then roamed from her face, to something to the side of the desk. She glanced to where his eyes now rested, and found a simple umbrella stand. Well what was so weird about that?
Wait. They’re not umbrellas.
The slim wooden hooks and sticks looked like the old fashioned canes she’d seen in a few films. She suddenly felt a chill come over her and her eyes shot back to his, where she found him waiting for her to realise, with amusement dancing over his face.
“Don’t be scared. I’m not going to hurt you. Not in a bad way, anyway. You’ll enjoy it. I promise.”
What should she do? She had the feeling that he could be trusted, and that if she asked right now, she would be allowed to go.
But then, she would have no tales to tell. She wouldn’t have learned anything. Was this ‘the basics’? She doubted it, but then if she was going to learn something, she’d learn it properly for once in her life. The calm, in control, older man in front of her was proving much more motivational than the stuffy teachers at school. Something about him told her she needed this. She needed it now.
“Ok. What do you want to do?”
Ball in his court. He caught it, and played on.
“I want you to take all your clothes off, fold them neatly, and put them on the desk.”
The deep breath she took was barely a respite from the near fainting. Could she do this? She was into it now; she had to.
Slowly she unbuttoned her school shirt and slipped it off, on to the floor. Goosebumps rose on her arms and over her pale chest, new womanly territory which was yet to be explored by other fingers than her own. She left the white, smooth cup bra on for a little longer, uselessly protecting her modesty which was soon to be ripped away. Reaching around her back, she found the skirt zip and tugged at it, then shuffled it downwards until it lay in a pool of material about her ankles. She stepped out of it, and out of the black low heels she’d worn all day.
Standing in her white bra, non-matching grey knickers and tan colour tights, she didn’t feel quite so attractive. She felt every bit the young, inexperienced girl she was. Only she could have given the come-on to an older guy while wearing the most unsexy underwear ever. She’d never expected to get this far, though.
She dared glance up at him, and his expression was mercilessly serious. He looked at her face, then; seeing her look at him. He didn’t even give a reassuring smile, just arrogantly expected her to continue. He let his glance drift from her eyes, back to roaming over her young body. Enjoying the show.
She rolled off her tights. She took the opportunity, while still in underwear at least, to fold up her clothes as neatly as possible. Never a forte of hers. She didn’t want to disappoint this man, who was willing to spend his time teaching her the way. Something about him made her want to obey, to do the right thing. Whatever he said was the right thing.
The moment was finally there, and the atmosphere was tangible. It felt like every eye in the world was on her in that moment, even though there was only the two of them there in his office and she had willingly given agreement of this to take place.
Unhooking her bra she let it fall from her arms to the floor; she bent over somewhat to give yet another useless attempt at modesty while at the same time hooking her thumbs into the sides of her knickers and pulling them downwards. Tearing away the final layer of innocence.
She gathered up these last few items and placed them atop her ‘neatly’ folded pile, then stood upright with them in front of her, ready to proffer them to Boss.
He was pleased, she could just tell. She’d done as he’d asked. There hadn’t even been a verbalised punishment for failure, it had only been a request. Perhaps she was a natural harlot after all.
“Good girl. Put them on the desk in front of you.”
It may have been her imagination but even in the fading light she thought the bulge at the front of his trousers was larger than just previously. She felt a tinge of pride that it might be because of her. Because of her body. And her obedience.
She placed the pile on the table, topped with her bra, tights and knickers, which were not as bone-dry as they might have been. He got up then, and walked around to where she stood, awkwardly trying not to shield herself from his eyes with her arms.
“Now. We’ll play a few games. You must trust me, though.
It’s like exercise. It’s all for your own good, although you might struggle at times.
You will put your legs apart for me, and you will place your head on your pile of clothes on the desk, and you will put your wrists behind your back, and hold yourself in that position. Do you understand?”
Grateful to be able to put her face against anything, she hurried to get into the right stance. Her breasts dangled on the edge of the desk when her face was pressed sideways on the clothes pile, and she felt her thigh muscles being stretched as she parted her legs, keeping them straight, but with her wrists behind her back, as he’d requested.
She felt the wood against the inside of her leg, first. Not high up, to start with; near her ankle. Stroking upwards, over her inner calf, then up over the soft inner area of her thigh. Her natural instinct was to close her legs, wondering where this touch may lead. Knowing where it would lead, if he wanted to.
He skipped that area for now, moving from one thigh over to the other, stroking her inner thigh on the opposite leg, then down again over calf and teasing her skin.
Her goosebumps had goosebumps at this point.
She needed something, but again wasn’t sure what. Sensations running through her were all completely new, although not as distasteful as she’d worried they might. Something about this man taking control was turning her on to insane levels, and he’d barely touched her with the tip of a wooden cane.
He stood behind her then, she saw his shadow approach nearer. Felt the material from the growing bulge at the front of his trousers, coupled with cool leather and metal from his belt, brush over her bare ass.
“You will probably find this next bit difficult, so I am going to help you.”
He took both her slim wrists in one of his large hands, pinning her hands to the small of her back. Moving away, to the side, he lifted something in his other hand, and brought down the cane in a strike to her bottom that lifted her head from the table and elicited an angry squeal.
“You’re not to say anything, unless that something is ‘Thank you Sir’,” he remarked, overly casual about matters. There was that arrogance again, shining through strongly. Wetness pooled at the apex of her thighs, threatening to make their escape.
“Thank you… Sir?” her questioning tone would no doubt have raised his eyebrow, and he lifted his hand again to strike, after first ensuring he retained a firm grip on both of her wrists.
She wriggled to move away from the oncoming blow, but it was of no use. He’d done this many times before, and the strike landed barely an inch from the first, by the feel of it.
She couldn’t help it; the squeal made its way into the room before she had time to think beyond the pain.
“What did I just say?”
“Thank you, Sir…” she mumbled sullenly, tears in the corner of her eyes. If they fell, they would add to the wetness in her knickers beneath her cheek. She caught the scent of herself from the day, and it only served to highlight her humiliation and predicament. A wanton slut. That’s what she was. It was good that her lesson was also her punishment.
Five more strikes, then he finally let her wrists go. She made as if to stand upright, the sudden freedom of movement giving her confidence, but he moved as quickly as a snake with a hand over the back of her neck keeping her pinned to the desk. Her ass felt like it was actually on fire. Not just metaphorically, but literally. She’d had to thank him after each one, while being certain the welts would last her for months if not years. That’s how it felt, in any case.
When he was certain she wouldn’t try to move again, he moved his hand from the mystifyingly comforting grip on her neck. He trailed his fingers down her spine, as if daring her body to respond after that unspoken warning. She didn’t take up the challenge. Her ass had had enough, for now.
He didn’t agree, and let his fingers roam over the hotness from her freshly caned cheeks, revelling in her piteous moans and the small wriggles she dared elicit.
“You did very well. Those were only warm up strokes, but they were enough for a new one like you. Good girl.”
That phrase unlatched the gate, and her drops of moisture made their bid for freedom at the tops of her thighs. Glistening, slippery girl-juice coated her soft inner thigh now, and when his fingers delved lower down and inbetween, she was found out. Caught.
“You slutty little bitch. I thought you were new to this, but you’re nothing but a slut!”
“No, Sir, I promise… I haven’t done anything, I mean… not like this… well – not like anything!”
He laughed at her worry, and in that instant she knew he’d been mocking her.
“It seems a shame to waste such an ardent desire. I don’t mean just yours, either.”
A slight clank of metal, and a gentle swish… was a that a belt being unbuckled? He stood behind her, and he knew he didn’t have to hold her in place for this part. He did, however, move her wrists from her back so her arms lay by her sides on the desk. Unzipping himself, he freed his large erection which, unbeknownst to her, had been threatening to cause bad business decisions all day.
A light brush of something hot, against her wet place, a place only her fingers had travelled before, dancing their dance to her secret fantasies. Not even in her fantasies had she imagined a scene as hot as this after-hours adventure.
As he slid himself into her virgin pussy up to the hilt, releasing pent-up frustration in a very audible sigh, she was filled with delicious sensations that made her question everything anyone had ever told her about sex.
Of course it was the sex. Glorious, new sex. But something else, too.
Perhaps it was the age difference. Perhaps it was the warm up.
Perhaps it was the fact she’d enjoy wiping that smug smile off Claire’s face in the morning.
– Cara Sutra