Debbie's Cruelty

The two weeks that Tim had been working on his company's new marketing strategy had been exhausting, but made enjoyable by sharing the task with Debbie, the junior colleague who had been assigned to him as an assistant. Much of that enjoyment came from the fact that she was intelligent, quick, and efficient. But he was honest enough to admit to himself that it was also because she was such an attractive young woman.

He could admit that to himself, but he wouldn't have done so to anyone else, and most certainly not to Debbie herself. As her senior manager, some thirty years older, and married into the bargain, to have done so would have risked accusations of sexual harassment and even the possibility of losing his job and his wife.

So Tim didn't just keep very quiet about his feelings, he did all he could to make sure that he didn't give, or at least was not seen to give, any inappropriate looks to his twenty-four-year-old assistant. But it wasn't easy. Her tall, slender figure, her pretty face framed by the fairish hair that hung just below her shoulders, and her flashing white smile and sparkling brown eyes all made sure of that.

And then there was the way she dressed. Oh, it was perfectly professional. Long or midi-pencil skirts, which revealed nothing except for the shapeliness of her hips. White blouses that gave no sign of cleavage, but did show the outline of her smallish, perky breasts. He assumed she was too naïve to be aware of her effect on a middle-aged man, whose wife had long since lost interest in how she looked, let alone in having sex. And he assumed she must certainly be too naïve to know that he had a constant semi-erection when he was with her which, after a few hours, led his balls to ache unbearably until he was able to masturbate. Though even that was only a small and temporary, release.

As they came to the end of the second week of the project Tim was uncomfortably aware that, middle-aged as he might be, his feelings were rather like those of an adolescent. It wasn't just that he was sexually enthralled by Debbie, it was that he had what would have been called, were he still an adolescent, something like a crush on her. He was still just about enough in control of himself to keep it disguised from her, but that control was becoming harder to sustain with each day that passed. He both longed for and dreaded the end of the project, after which their daily interactions would cease and, he hoped, his infatuation would end.

Tim was entirely wrong about Debbie, though. She was actually very well aware of the effect she had on him, as she often had on men, and it amused her. No, more than that, it gave her a thrilling, intoxicating feeling of power. So she also knew that when she suggested that they spend a day at her flat, to work intensively on the final version of the report, Tim would be in a fever of imagination about what it might lead to. It gave her a cruel pleasure to know that he would have to try to conceal it. And it gave her an even crueller pleasure to anticipate how she might use her power.

When he arrived at her flat, early on Friday morning, Debbie offered Tim some coffee and invited him to sit down at the dining room table, where they could work on her laptop. She was wearing black knee-length boots, a fairly short black skirt with a slight slit up the side, and a tight white blouse. When she sat down, she knew very well that he immediately noticed that her skirt had ridden up her legs, exposing the lacy tops of her black stockings. For Debbie had dressed very carefully that morning, calculating and checking exactly the angles and the postures that would reduce her middle-aged senior colleague to a quivering wreck of frustration.

Tim tried desperately hard to concentrate on their work but could not help but glance surreptitiously from time to time at her legs and stockings. Debbie let that go on for half an hour or so, before affecting to notice for the first time.

"Are you looking at me in an inappropriate way?" she demanded sharply.

Horrified, Tim stammered an apology, and, having been confronted in this way, could think of nothing to say other than admit being distracted by her stocking tops

"Look," Debbie replied. "We are colleagues. I'm not wearing these for you. I'm wearing them for my boyfriend, who is coming round later. He's got a thing about seeing me in sexy underwear, and I like to please him, OK?"

Tim stammered some more apologies, but Debbie continued.

"You've my boyfriend, haven't you? At the Christmas Party. Have you got any idea what he'd do to you if I told him you had been perving at me?"

Tim could guess only too well. He had only met Jamal briefly, but his powerful physique was obvious, and the fact that he worked as a security guard at one of the city's most fashionable nightclubs suggested that he would be more than capable of making his displeasure known to a flabby middle-aged man like Tim.

"He'd destroy you," Debbie said simply. "Whilst I watched. Now can we get back to work, please?"

Tim tried to obey her, but before long his eyes were drawn again to her legs and, now, he realised that through her tight white blouse he could see the outlines of her lacy black bra, just as Debbie had intended him too, had he known it. Despite her warnings, he just could not stop himself from looking, especially where the buttons of her blouse parted to reveal the swell of her breasts.

"It seems you're willing to take the risk," Debbie said, smirking slightly. "Or perhaps you can't help it. I understand, of course. You're bound to feel lecherous when you see someone as sexy as me in front of you. Is that it?"

For the first time, Tim realised that this young woman was very far from naïve, and actually understood the effect she had on him. It emboldened him to let it all spill out. All the weeks he had been in a frenzy of lust for her, masturbating to the thought of her. The frustration. The anguish, The torment.

"I already knew all that," Debbie said, with devastating simplicity. "So what?"

"Please," said Tim, all pride gone. "Please, put me out of misery."

"Why should I?"

"Because I love you," he said recklessly.

"Oh, how sweet," Debbie said, in a bored voice. "But what about your wife? Carol, isn't it? And haven't you got a daughter about the same age as me? Amy, I think you told me her name was. What would she feel about all this?"

"I don't care," he said, in a pitch of such excitement that it was true. He didn't know where lust ended and love began. "I only care about you."

"Well, well," Debbie said coolly. "You have got yourself into a state, haven't you? Poor Tim. OK, I'm going to take pity on you. I think I will allow you to wank yourself in front of me. Go on, take your cock out and pay homage to my beauty."

He did not need any encouragement and stood up, took out his cock and began to masturbate. Debbie watched for a few moments.

"Don't you feel ashamed, jerking off in front of someone who is the same age as your daughter? Though I must admit it would be an incredible turn on if you were to tell me that you're imagining that I am her. Amy, I mean."

"I am," said Tim, overwhelmed by the idea that he might be able to excite Debbie by just saying a few words. "That's exactly what I'm doing. I'm imagining you are Amy!"

Debbie didn't make any comment, and just turned back to her laptop and continued to work, apparently indifferent. But, from time to time, she would issue a casual instruction for him to go faster, or slower, barely glancing at him to ensure his compliance. Then she ordered him to stop.

"You didn't think I was going to allow you to come, did you?" she asked, pretending to be puzzled. "I know you're dying to, aren't you? You think you're going to be allowed to jizz all over my sexy legs and stockings. But I don't think my boyfriend would permit you to do that, do you?"

"But you can't just leave me like this ...." Tim began.

"Can't? I can do what the hell I like! I didn't ask you to start leching over me" Debbie snapped coldly.

He apologised.

"Well," she said, a little more kindly. "I suppose there's no way you're going to be able to concentrate on work while you're in that state. You'd better come with me."

Debbie stood up and walked slowly to her bedroom. Tim followed, watching every move of her sleek, sexy body. She ordered him to lie down, and sat beside him on the bed. She took his penis in her hand and began to stroke it -- sometimes fast, sometimes slow. Sometimes she used just her finger and thumb, other times her whole hand; sometimes she gripped hard, other times barely touching him at all; sometimes she went up and down the whole length of his penis, other times just circled over and over the head. Tim could feel myself on the point of coming when she took her hand away altogether.

"I haven't decided whether I should let you come," she giggled. "That's up to me, isn't it? I own your cock now. Your rather little cock, I may say. I wonder how poor Carol makes do with that. But you don't care about her, do you? You said so. You only care about me. And I could give you the pleasure you're craving. Or I might just be cruel and leave you hanging on."

She started to touch Tim again, and again brought him to the point of orgasm before stopping once more.

"Hmm, you know, I realise that I was very thoughtless dressing this way. It was bound to get you over-excited. Perhaps I had better change."

So saying, Debbie got up from the bed and went over to her wardrobe. She took out an elegant A-line dress. Then she slowly unbuttoned her blouse and took off her skirt, standing before her manager just in her boots, black stockings and suspenders, panties and bra.

"Close your eyes," she said. "Only my boyfriend is allowed to see this."

Tim closed his eyes and heard the rustle of material. Shortly afterwards Debbie told him he could open them. She was sitting on the bed again, now wearing her dress. In her hand she held her black lacy bra.

"I don't need to wear a bra with this dress," she explained. "My cute little titties are very firm and I only wear a bra when I have something like that white blouse on, just in case lecherous old creeps like you get the wrong idea."

With that, she wrapped the bra around Tim's cock and began stroking him again, the material of it and her firm grip bringing him almost immediately to the point of orgasm again.

"Say please," she ordered.

"Please, Debbie, don't stop, make me come," he begged.

With a few skilful, sharp tugs she brought him to a shuddering orgasm, his spunk running over her bra and hand. As he was getting my breath back, Debbie dropped the bra on his penis and said:

"Now we had better get back to work. And please don't look at me in an inappropriate way again."

She stood up, tugged her dress into place and walked out of the room without a backward glance. Shortly afterwards, when he had recovered, Tim followed her. She was sitting at the table again, working at the laptop.

"Better now?" she asked, glancing up at him. "Well, I hope it was worth it. Because you know I'm going to have to tell my boyfriend about how you forced me to take pity on you, don't you? And I think he might just be a bit annoyed with you. Plus, of course, there are Carol and Amy, your wife and daughter. I mean, I know you don't care about anyone but me, you said so, but I have to consider their feelings, don't I?"

"Debbie, please ... can't we just forget this every happened?"

"Please, Debbie, this. Please, Debbie, that. How many things have you asked me to do today, just to please you, all the time telling me that you love me, and that you don't care about anything else but me. You can't just use me to satisfy your lechy little urges and then start bleating 'let's forget this ever happened'"

There was a tone of anger and menace in Debbie's voice, but also a sense of cool, controlled cruelty. She stared at Tim, holding his eyes in her hard gaze for several moments. Then she looked back at the laptop.

"Let's get this report finished, shall we?"

Somehow, Tim managed to force himself to concentrate on the report and, within a couple of hours it was ready to be submitted. With that done, he returned to what was uppermost in his mind.

"Look, Debbie," he began. "I really am sorry about before."

"Are you? Why? I thought you enjoyed it?

"Well, yes, of course I did. But I just mean, please don't tell anyone."

"So we're back to 'just forget it'?"

"Yes, if you want to put it that way. I mean, it's not as if either of us come out of it very well," Tim said, attempting to sound humorous.

"What do you mean? How do I 'come out of it' badly?"

"Well, you know. Jerking me off with your bra ...."

"Tim," Debbie said firmly. "You begged me. 'You can't leave me like this', were your exact words, if I recall. After you had begged to be allowed to masturbate to me, and told me you were imagining I was your daughter. So I took pity on you. How, exactly, do I come out of that badly?"

"So what are you going to do?" he asked, panic-stricken.

"I'll have to think about that, I suppose," Debbie replied casually.

Tim could think of no response to that and, reluctantly, left Debbie's flat. He didn't go home. Instead, he went to a pub and drank several large whiskies. They didn't suppress, but exacerbated, the growing feeling of dread. What had he done? How could he have been so stupid? How could Debbie now seem so very different from the innocent object of his adoration he had imagined until that day? And, more than anything, what was she going to do now, and what would happen as a result?

He didn't know it, but the answers to some of those questions were beginning back at Debbie's flat. After Tim had left, she did some internet searches and found some email addresses. Then, she licked her lips and, frowning with concentration, wrote two emails.

Debbie's first email was to Tim's wife.

Dear Carol

I'm really sorry to email you 'out of the blue' with what I know will be a difficult message to receive. You don't know me, but I work with your husband, Tim, as a junior assistant. The thing is, I'm a bit worried and confused by the way he's been behaving towards me. I really don't want to cause any trouble for him by reporting him to HR at work, or to cause any problems between you and him, but I feel as if someone needs to know, because I'm worried he is having some sort of breakdown. I'm only twenty-four, and I'm a bit out of my depth to be honest with you.

Basically, over the last few weeks I've noticed him looking at me a lot -- you know what I mean, looking down my top or up my skirt -- even though I don't think I've done anything to encourage him. He seems to have got very het up because he sometimes manages to get a glimpse of my undies. Maybe I'm a bit naïve, as I never had any idea what was going on his head.

Anyway, if that was all, I'd just have ignored it. I'm really not a troublemaker who runs around complaining just because a man has looked at me a bit inappropriately! The thing is, though, that today he manipulated me into letting him masturbate in front of me. I suppose I should have stopped him, but he seemed in such a state and I didn't know what else to do. He said he couldn't concentrate on his work and then he said a whole load of things about how he only cared about me, not you or his daughter (Amy, is it?). I'm sure he didn't mean it - he's probably just having a mid-life crisis or something.

After he'd finished, he suddenly told me to 'forget all about it', but it's not the kind of thing you can just forget, is it?

Please keep this to yourself. I honestly don't want him to get into trouble as he would lose his job if anyone found out about this. And I would hate if Amy found out, especially as I understand she is about the same age as me. Also, if my boyfriend ever found out, I don't know what he would do to Tim. But I'm a very honest person, and I don't like having to conceal things from my boyfriend. I'll try not to tell him happened today, but if Tim continues like this then I don't think I will be able to keep it from by boyfriend.

Anyway, I just feel so upset and confused that I had to tell somebody. I suppose I'm hoping we could somehow tackle the problem together. Could we talk or maybe meet?

Best regards

Debbie

Debbie's second email was to Tim's daughter.

Hi Amy

Sorry to write when you don't know me, especially as what I've got to say will weird you out. I work with your Dad, Tim, as a junior assistant, and lately he's been behaving a bit strangely. At first it was just lecherous looks. I guess that, like me, you're used to old guys in the office doing that. Men, eh!

The thing is, though, that today he pressured me into letting him jerk off in front of me. I realise I was stupid to let him, but he was very insistent. But, if it was 'just' that, I wouldn't be writing to you. The thing which really freaked me out was that he said that he was imagining that I was you -- apparently, we're the same age. I didn't know what to say. I mean the whole thing was totally freaky anyway, but when he said that I was lost for words. Then he just asked me to forget all about it, like I could do that!

I can't imagine what it will feel like for you to hear about this. But the fact is that I feel I have to tell someone. I could tell my BF, but he'd go mad and would probably kick the s*** out of your Dad. I don't like keeping secrets from him, though, as I am basically a very honest person, and I think trust is really important, so if anything like this happened again I think I'd have to tell him.

I really don't want to get your Dad into trouble. I mean, he'd lose his job if this came out, and your mum would go mad as well, and he's probably just having some kind of mid-life crisis or something.

To be honest, I guess I am hoping that you and I could somehow deal with this together, seeing as we're the same kind of age. Like maybe sit down with your Dad and try to work out what's behind it all?

Debbie x

After Debbie had sent both emails she smiled to herself. A thin, cruel, triumphant smile. Then, looking at her watch, she realised her boyfriend, Jamal, would be arriving soon.

She was still wearing the A-line dress, with no bra, but panties, suspenders and stockings underneath. The outfit she had worn when she jerked off Tim. It would be fine for Jamal, except that she was aware that she was soaking wet between her legs now, the result of her excitement about her power over Tim, and of her emerging ideas about how to exert that power over him and his family.

And she was aware that she wanted her boyfriend to have access to her hot, wet, fuck slit the moment he arrived. So Debbie removed her sodden knickers and went to her bedroom, knelt on the bed, and flipped her dress above her waist so that the moment Jamal walked in he would be able to take her.

She heard his key turn in the lock of the front door and she called to him. He entered the bedroom and saw her.

"Do me," Debbie urged. "Shove your cock into your nasty little cumslut girlfriend. Use me. Stretch me out."

She felt him enter her, with his whole length, and then he began to pound her. As he did, she heard the ping of a new email arriving on her phone and, shortly afterwards, another. Eventually, Jamal exploded, pulling out of her to spray his jizz on her belly, breasts and face. They lay together for a while, recovering. Then, Debbie looked at her phone.

Carol and Amy had both replied. Debbie, her conventional sexual desires now sated, turned her attention to the deeper, less conventional, and completely insatiable desires she had. To be cruel. To humiliate. To control.

To be continued