The Perils of Penelope

Stephen checked his watch. Fifteen minutes to the end of the working day. He began his usual 'home time' ritual by closing down his computer and then moved to put away the long lists of cash flow forecasts and bank statements. The business was doing well, but it could be doing better. One more big client and things would definitely be looking good. That wasn't his department though. His organised mind ran, quite simply, to organising. He did not have the flair and gut instinct required to create and sell their services. Those skills and responsibilities belonged to Penelope.

A tentative knock on the door interrupted his thoughts. Speak of the devil and there she was. All designer clothed and power dressed. Penelope had the classic look of those top-drawer 'girls in pearls' but she was driven by more than a desire to go grouse shooting on Daddy's estate. There was something different about her, something that got the clients going, something that, because he didn't possess it himself, Stephen could never quite give a name. Whatever it was, young Penelope had it; and that, most of the time, was the secret of their success.

"Stephen," She said, her voice unusually gentle. "The Johnstone file. Could you review it for me?"

He looked up, directly into her blue eyes, noting the slight flush to her cheeks. She was a capable woman. It was not often that she asked for his help. He checked his watch once more. The gym could wait. "Leave it here." He replied. "Come back at six and we'll go over it." Then he watched her as she placed the file on his desk, her eyes unable to meet his.

Half an hour later he knew all he needed to know about the Johnstone case. This was a company that was clearly in the market for their services; that would just as clearly have benefited from them, Yet Penelope had somehow overdone the selling. Johnstone's initial enthusiasm had turned to indifference; whatever technique she had used had been the wrong one. It happened sometimes; those who are blessed with flair and creativity can occasionally overdo it, turning a money making chance into no chance at all.

At six precisely Penelope knocked on the door once more. Stephen motioned her in and took one last look at the file before closing it with a snap. There was no other chair in his room so she could only stand in front of his desk with her hands clasping somewhat nervously in front of her. Taking his time Stephen looked her up and down, taking in the soft curves of her body encased in the armour of her city suit. Normally he would have been more subtle in his appreciation of her, but they both knew that with this case Penelope had made a mistake. Consequently he felt free to take a few liberties.

"You flirted with him didn't you." He said. It was not a question. Flirting was Penelope's favoured selling technique. She nodded.

"Say it." Said Stephen.

Penelope looked at the floor. "I flirted with him. The man from Johnstone's," she looked up at him, defiant, "but, he liked it, and it was only flirting!"

"I'm guessing," Stephen interrupted, "but I bet he liked it when he was on his own. It was only when you flirted in front of his secretary that he changed his mind."

Penelope looked down again and then up at him once more. She was always surprised when he saw through her wily ways. She operated on a quick, instinctive level. His strengths were more thoughtful.

"How did you know?" She asked.

"You should have checked their headed paper and the company search I had done more carefully. His secretary is actually his common law wife; and she owns just as much of that company as he does."

"Oh." Said Penelope.

"Yes." He replied. "Oh." Stephen was enjoying the power he had over her. He knew she was used to getting her own way. Next he let the silence work on her; allowing the foolishness of her error to hit home. She was only ever this vulnerable when she was in the wrong.

"I'm sorry," She said. "It won't happen again."

"I'm going to make sure of that. You of all people should know how important it is to pick up a client like the Johnstone Company." Penelope had her eyes firmly fixed on the floor. Stephen looked her up and down once more. He sighed, "I'm going to have to spank you, Penelope."

"That's outrageous!" She cried; then she noticed the serious set to his jaw. Penelope quickly thought it might be better to plead. "No, please, not that.."

Stephen was firm, as he knew he had to be. "Penelope. You know why you are here. You know you deserve it. If you argue it'll just be a harder, and longer, ordeal."

She paused, caught between her instinct to rebel and her knowledge that she was in the wrong. Stephen believed that it was at moments like these that she was at her most beautiful. "Look." She said, "I made a stupid mistake. I'll do anything to make amends; but, please, don't spank me."

"You decide, Penelope." He replied. "I can go to the board with this or I can tan your backside." He paused, then added, "Anyway, you say you'll do anything to make amends. So you'll certainly be able to put up with the minor inconvenience of having to stand for the rest of the afternoon."

It only took her a few moments to make her choice. Penelope nodded, then her hands fell to her sides as she waited for his next instruction.

"Say it."

Stephen's words brought an increased blush to her face. Eventually, Penelope forced the words out, saying, in a small voice, "Please Stephen, I deserve to be spanked."

Stephen spoke slowly and clearly, knowing that each word would work it's different magic on them both. "Undo your hair" He said. "Lift your skirt up to your waist. Take your knickers down to your knees. Bend over my desk." He paused. Penelope's blue eyes were burning into him. "Do it in that order, and do it now."

He loved to watch her; and she had discovered that she loved being watched. Somehow his firm tone and watchful eyes pushed the right buttons. She wanted to provoke him. In moments she was tossing her long hair loose from it's coiffure. Then, with legs slightly apart, her delicate fingers took the hem of her knee length, pleated skirt and raised it up, above her stocking tops and past her flimsy, high cut knickers. With one hand she held it at waist height.

Stephen ran his tongue over dry lips, tasting his own anticipation. He could sense that it was matched by the young woman in front of him. As his eyes roamed over what she had freshly revealed he felt the familiar stiffening of his flesh. He was charmed by her charms, bewitched by her chemistry. She usually dictated the way things should go, so, it was hard to set the pace himself.

"Don't think that such a blatant display will make it any easier for you." He said. "Take that excuse for a pair of knickers down. Now." He sounded firm, harsh even; but they both heard the catch in his voice. She was getting to him. He resolved to take it out on her pert buttocks.

There were two sides to it for Penelope. On one hand there was the rush of blood to her loins that she was experiencing as she posed provocatively for him. On the other there was a certain sense of shame at what she was doing; a rush of blood to her head if you like. The two feelings combined to create a strong emotional brew; it was always surprising, but she liked it.

It rose to a crescendo when she was removing her knickers. When her carefully trimmed curls came into view, as his cool eyes feasted on the sight of her swelling mound she became acutely aware of her own power.

She leant forward onto his desk, her eyes on his, then flicking to his lips, and then quickly to the squirming bulge in his trousers.

"Are you ready?" He asked.

"Yes." She replied, thinking, in more ways than one.

She was surprised though, when he kissed her. He had never kissed her before. His tongue was warm and wet; pleasantly roaming inside her mouth; her own tongue pressed against his, tasting what was to come.

Then he thrust his hands down the loose neck of her top, his fingers somehow finding the stiff buds of her nipples straight away. He squeezed gently, allowing them to stiffen further, and then squeezed again. Penelope's pussy throbbed in response and she groaned into his mouth. Abruptly Stephen stood up, bringing his own stiffness to within inches of her open mouth. She watched as he began to unbelt his trousers, surprised at how much she wanted to mouth his fleshy pole. So near, she thought.

So near and then so far, because Stephen moved away, around the desk. The next thing she felt was his cool hands on the curved flesh of her bum cheeks. Cold fear replaced hot anticipation in her heart. He was going to spank her. Oh God, he was going to spank her with his belt.

Stephen swished the leather belt through the air, once, and then twice. The third time he cracked it down hard onto the cheeks of Penelope's arse. Then because he liked the way she yelped, he did it again.

Two red stripes criss crossed her otherwise alabaster cheeks. She had cried out both times but she'd also held her position. He was pleased. Stephen caressed her soft flesh feeling the cool and the warmth of each stripe. His fingers strayed further and he heard Penelope sigh as they found her wet pussy. He lingered there, touching her, teasing her. She rocked back against his hand, hungry.

Two more swift cracks of the belt assailed her sweet posterior. Penelope's hands gripped the desk top. White knuckled she licked her lips. She didn't know how many she would have to face. She hoped he would stop when she was ready. Already the heat from her abused backside was throbbing, and the different heat of her wet cunt was mingling with it; changing the pain and being changed by the pain. She heard the belt fall to the floor, felt one, and then two of his fingers slip inside her. There's nothing like the sensation of being filled, she thought. Slowly In and slowly out; in and out; his rhythm equal to the hot throbbing.

Then he used his hand in a different way, spanking lightly on to her flesh. Her skin began to get that crimson glow. Now, only one hand supported her body on the desk. The other had stolen between her legs and was gently circling the hard nub of her desire.

Stephen watched her fingertips rubbing around her clitoris and became acutely aware of his own desire. He channelled it though, spanking her harder, making her gasp with the delicious pain. He stood behind her, and before long was pressing himself against her while still spanking her reddened flesh.

In turn Penelope ground her hips back at him; slipping her fingers back, groping for, and finding, his hard cock. Stephen stepped away from her questing fingers. Slowly he unzipped himself, enjoying the sudden freedom. He placed the head of his thickness at her entrance, rubbing her with it, making it wet, teasing them both. Penelope gasped, "Fuck me, please, fuck me."

He slid his length gently into her, relishing the joy of pushing himself inside her velvety wetness. Then he tried to recapture the feeling and thrust again, and again. His hands rested on her hot flesh. Once more, to the rhythm of his own cock thrusts, he began to spank her.

Punishment and penetration, pleasure and pain; waves of both washed over the unfortunate Penelope. Mind you she wasn't complaining. Her fingers nestled between her thighs once more, circling and pressing wherever a little extra sensation was needed. She loved the feel of him inside her, thrusting, faster now, deeper. She loved the feel of his hands on her burning cheeks even more. That was what she needed. She'd known it the first time she'd seen his hands. They were delicate, fine boned and yet big enough. His touch was the gentlest and firmest that she'd known.

"Yes." She said, and ground her hips back at him, wanting him further inside.

"Yes." He replied, reaching forward to grab her hair, so that he could pull himself in deeper. He looked down once more, saw his bigness entering her, felt himself inside her, knew that he couldn't hold it.

Hot sperm jetted into her wetness. His coming pulsed inside her, pushing her own body into a screamed orgasm.

"Fuck me!" She said. "Fuck the naughty girl!"

It was too much. Papers flew and a telephone hit the floor. Stephen and Penelope collapsed onto the desk, laughing, gasping, released at last. For a moment they held each other, then, slowly, reluctantly, he had to let her go.

It hadn't been easy working for a woman; not at first. Not if you were like Stephen. Then, after a while, he'd seen just how good she was. Let's face it he decided, she's paying my wages. Which means I'd better give her all the help I can. Penelope didn't make many mistakes; maybe two or three in a year. The first time that she'd asked him to correct her behaviour he hadn't been too sure about it. She'd really had to plead with him. Of course, these days it was a labour of love.