Debbie's Cruelty

Author's note: This story only really makes sense if you read Part 1 in full.

Summary of Part 1:

Tim, 54, a senior manager, becomes sexually and emotionally infatuated with his assistant, Debbie, 24. He doesn't realise that she is deliberately cockteasing him with revealing glimpses of her sexy underwear. Whilst working with him at her flat, she challenges him about looking at her inappropriately, protesting that she is only wearing sexy underwear for her boyfriend, Jamal, 34. Tim reveals that he has become obsessed with her, and loves her. She agrees to allow him to masturbate in front of her, and as he does so she persuades him to say that he is imagining that she is his daughter, Amy, 24. Subsequently, Debbie masturbates Tim to orgasm.

By now, it is clear to Tim that Debbie is not the innocent young woman he had assumed, but is highly manipulative, so he is terrified when she starts talking about telling his wife, Carol, 47, as well as Jamal and Amy, what has happened. He leaves her flat and gets drunk. Meanwhile, Debbie emails both Carol and Amy, giving highly selective and misleading accounts of what has happened, and implying that she is an innocent young woman who is merely concerned that Tim is having a mid-life crisis. She then has passionate sex with Jamal, during which Carol and Amy reply to her emails. Part 2 begins with her reading those replies.

Warning: Part 2 of this story includes a scene of a sexualized nature involving a father and his 24-year-old daughter.

Section 1: Carol and Amy reply to Debbie's emails

Debbie opened the replies to the emails she had sent. The first one was from Tim's wife, Carol:

Dear Debbie

I wish I could say that I was surprised to receive this, or that I don't believe you. But I'm afraid that neither is the case. It is all too familiar. Apart from anything else, my husband has a fetish about women's underwear, so it doesn't surprise me that he has been trying to get glimpses of yours, and getting into a state when he does so. You mentioned our daughter Amy, and, if you can believe such a thing, I actually once caught him kissing and sniffing her knickers whilst he masturbated. I never guessed when I married him that he was a pervert.

So I'm just sorry that you have had this experience, and I do appreciate you saying you won't report it at work. I would be happy to meet you to discuss all this, and I think it would be a good idea to do so. When would be a good time for you?

Kind regards

Carol

Debbie then turned to Amy's reply:

Debbie

I don't know who you are but you are a liar and must be sick in the head. My dad would never have said that about me and I am going to tell him what you wrote. If it is true that you work for him then he will get you sacked.

I don't ever want to hear from you again.

Amy

Debbie pondered these messages, and then replied to Carol's, arranging to meet her at a café in town tomorrow, Saturday, morning.

Section 2: Amy talks to her father

As Tim left the pub on Friday evening, worse the wear for the whisky he had drunk, his phone rang and he saw that the caller was his daughter, Amy. The moment he answered she launched into a tearful tirade.

"Dad, I've just had a weird, horrible email from someone calling herself 'Debbie'. I just can't believe it. She actually said -- I can hardly tell you -- but she said that you had, well, 'jerked off' in front of her and that you said you were imagining that she was me. She says she works for you? Is that true? I told her that you would sack her when you found out."

"Oh, God, Amy, why did you say that? What have you done?"

"But, dad, she's telling disgusting lies about you."

Tim remained silent.

"Dad?" said Amy, suddenly alarmed. "It is a lie, isn't it? It must be."

"Oh, Amy, of course it's a lie. Well, I mean I wasn't really thinking about you, but she tricked me into saying that I was."

"What? What do you mean? How could anyone trick you into saying something like that?"

"It's hard to explain, sorry, I've had a few drinks, but I promise I didn't really mean it."

"That makes no sense at all. It's just... sick, it's disgusting. How could you possibly say something like that about me, about your daughter?"

"Amy, I..." Tim began, but she had cut the call. Realizing that if Debbie had contacted Amy, she would surely have contacted his wife, Carol, he decided not to go home, but to check into a hotel, where he fell asleep in a drunken stupor.

After Amy ended the conversation with her father, she sat for a long time, shaking and crying. Then she wrote another email.

Debbie

I've just spoken to my dad, and it seems there is more to this than I thought. I can't get my head round it. Can we meet?

Amy

Debbie replied almost immediately, and arranged to meet Amy the following afternoon. As she wrote, a cruel smile played on her lips.

Once the reply was written, Debbie went to her wardrobe, selected a pale green satin slip, and returned to her bed. Jamal had fallen asleep, but began to stir when she grasped his thick, heavy cock in her hand and soon he was awake and ready. She climbed on to the twelve inches of his erection, hitched the slip around her waist, and began to ride him.

Section 3: Debbie and Carol meet

The following morning, after Jamal had left, Debbie showered and prepared to meet Carol. She dressed casually, in jeans and a sweater, and without make-up, intending to dispel any idea that she had provoked Tim's behavior. Even so, she had a certain stylish elegance, but mixed with a sense of youthful innocence.

Carol arrived on time. Although in Tim's mind she had ceased to take an interest in her appearance, this wasn't really true. It was true that she didn't do so in the way that he meant, which was to dress in sexy underwear and provocative clothes. But she kept herself in good shape at the gym, so that, although she was forty-seven, her body was still firm, and the sunbed ensured that she had a good even tan. Weekly visits to the hairdresser kept her dark brown hair neatly styled. As for clothes, she dressed carefully and smartly and, that morning, was wearing a short-sleeved red dress, cut square across her bust, showing just the hint of her cleavage.

In short, as Debbie immediately saw, she was a well-dressed, well-preserved, attractive middle-aged woman. It also soon became clear that she was both sensible and unhappy, for she talked quite openly about Tim and her marriage to him. She began by apologizing again for what her husband had done to Debbie the previous day. He hadn't come home that night, presumably from guilt, or fear that Debbie had contacted her, so she hadn't had a chance to confront him. And she re-iterated that his behaviour sounded as if it all grew out for the fetish that he had about women's underwear.

"I think so, too," agreed Debbie. "Because apart from what I already told you in my email, about how over the last few weeks he has been perving at my undies, yesterday he was going on and on about my stocking tops and how he could see the outline of my bra through my blouse. It was after that when he started masturbating in front of me. I was so shocked."

"It's pathetic, really," Carol responded. "He thinks I don't know that he pores over my lingerie catalogues, like a schoolboy, and of course looks at pictures online. He gets off on all kinds of underwear, but his absolute obsession is basques and corsets. He used to constantly pester me to wear them, but of course I refused."

"Do you mind if I ask why? I mean, why you refused?" asked Debbie, responding to the other woman's openness. "I mean, you've got a great figure, if you don't mind me saying so."

"That's sweet of you," Carol smiled. "It's not so bad. Not quite as sleek as yours, but better than plenty of women my age, including my daughter I may say. But, well, to be very honest with you, by the time he started asking, I'd long ago given up on him sexually. The fact is that -- well, you've seen it, so you know -- the fact is that his dick is just too small to satisfy me, and he only lasts a few minutes, into the bargain. So why should I dress up for him, just for a couple of minutes of totally unsatisfying sex? And, more recently, since I found him sniffing at Amy's knickers I've just felt, well, almost contempt for him, at least in a sexual sense. So we don't do it any more anyway."

"Did you tell Amy about what he did?"

"No, but do you know, I've often thought that I should. She -- you haven't met her, have you?"

"No," said Debbie truthfully.

"Well, she has a very starry-eyed view of her father and she always takes his side against me, so I can't help thinking it would do her some good to know just what sort of man he really is. To be honest, though, I have very little to do with her nowadays, even though she still lives in the town. She isn't the kind of daughter I hoped for, and more than Tim is the kind of husband I wanted."

"But you stay with him?" asked Debbie curiously.

"Oh, well," Carol replied, "I was brought up to think that marriage is for life, and he's a good provider. I really don't want to go through all the upheaval of a divorce and ending up in some horrid little bedsit. And at my age, having had a child, sex isn't really the be all and all. Though I must admit I do get frustrated. I'm not old, and I still have, you know, needs, so sometimes I wonder how long I can continue like this. Especially after what he has done to you."

"Stop me if I'm being too intrusive, but have you ever had affairs? I mean, if you and Tim aren't having sex any more...?"

"I don't mind you asking. To be honest, it's good to have someone to talk to about all this. Yes, I've thought of an affair -- fantasised about it, too, about finding a lover who is well-endowed and virile, everything Tim isn't -- but how would I meet such a man? I'm stuck. It's pathetic, isn't it?"

"It really isn't, Carol," said Debbie, and she meant it. She genuinely liked the older woman, and sympathized with her. Debbie, as she knew only too well, was a cruel, manipulative, and heartless person. But she was not just that. She was also capable of kindness and empathy.

"Well, anyway, there it I," said Carol. "Now you know the whole sorry story. All I can do now is promise you that I'll give Tim a good talking to and make sure he never bothers you again. I wouldn't blame you if you reported him to your company but, selfishly, I'd be so grateful if you didn't. I don't know what we'd do if he lost his job at his age."

"Oh, I'm not intending to do that. But, you know, I do think there is a better way of dealing with this, better for both of us -- you and me, I mean," said Debbie.

And then Debbie explained her plan. Carol listened in astonishment at first, and then a slow smile came to her lips. When they had fully discussed it, Carol agreed that she would wait in a bar near to Debbie's flat from about 7pm that evening, and would come round as soon as Debbie texted her.

The two women briefly hugged and kissed each other's cheeks before going to their respective homes. When Debbie got back to her flat, she had a long phone call with Jamal.

Section 4: Debbie and Amy meet

Debbie had taken a perverse satisfaction in arranging to meet Amy in exactly the same coffee shop where she had met Carol that morning, even arriving early enough in the afternoon to ensure it was the same table.

But Amy was a very different person to her cool, composed, and endearing mother, as was immediately obvious when she rushed in, red-faced and perspiring. Debbie quickly appraised this girl who, although she was the same age, had none of Debbie's poise or sexual allure. Her hair was greasy and her face was spotty. She was overweight and, whereas Debbie's jeans hugged her slender legs and thighs, Amy's were shapeless and hung slackly around her bulging stomach. And Amy's over-sized tee-shirt clung sweatily to her breasts which, whilst very large, were obviously droopy and slightly different shapes to one another.

"Cow's udders," thought Debbie, contemptuously.

Immediately, Debbie felt the desire to bully this lump of a girl, exactly as she had bullied so many similar girls throughout her life. But she knew she had to contain that desire for the time being.

Without preamble, Amy launched into a long account of how upset she was, which only increased Debbie's contempt for her artlessness and lack of sophistication.

"Dad said you tricked him. You tricked him into saying that horrible thing," she gabbled.

"You mean, saying that he was imagining I was you when he jerked off in front of me?" Debbie asked calmly. "But how could I possibly 'trick' him into saying that?"

"I don't know," Amy muttered.

"Look, Amy," Debbie said. "We're on the same side. I know you love your dad, and I, well, I certainly don't want to make trouble for him. If I did, I'd simply report him to HR in my company. It just seems as if he has problems. For a start, he's got a thing about looking at girl's underwear. But that's not so unusual, is it?"

"Isn't it?"

"Ah, come on, Amy. You're not telling me that men have never tried to look up your skirt or down your blouse? With those great big knockers of yours?"

"Knockers? What do you mean?"

"I mean your breasts, Amy. Surely you must know that men get turned on by girls' breasts? Haven't you ever had men staring at them?" Debbie asked, trying to hide her irritation.

"No. I don't think so. I don't know."

"Well, maybe they don't with you," said Debbie, now unable entirely to conceal her contempt for the other girl. "But they certainly do it to me."

"Not my dad, though. I don't believe it."

"Oh, Amy, get real. Your dad is a man, isn't he? And, what's more, your mum has told me that she once caught him wanking to your knickers. She didn't tell you, of course, but it's true."

To prove it, Debbie took out her phone and showed Amy the email Carol had written.

Amy looked horrified.

"I just can't take this in," she said eventually. "I don't know what to do."

"OK, well I'll tell you what I think," said Debbie. "I think your dad has just got a bit confused. Got his wires crossed, so to speak, and you can help him. I mean, you love him, right? You don't think he's a bad man, and you want to help him. He fancies me, and because I'm the same age as you, he has kind of mixed the two of us together. I'm sure that's all it is."

"Yes, but what has that got to do with him -- him sniffing my knickers whilst he masturbates? God, that is just so gross, even to think of. But that's not him confusing you and me, is it?"

"No, I guess not. But who knows? I can't be the only woman he's perved at in the office. Perhaps he got all worked up leching at some girl at work and then pretended your knickers belonged to her? Men are weird. Believe me, I know," Debbie responded.

"Really? Are you saying that it's normal?"

"Maybe not normal, but more common than you probably think. I bet plenty of men fiddle around with their daughter's undies on the sly. But, anyway, that's not really the point, is it? The real issue is him saying that he was imagining that I was you when he masturbated in front of me. So here's what we do. We meet him together, talk it all out, and uncross the wires. What do you think?"

"I -- I don't know. It all seems so weird. Are you sure that would work?"

"Trust me," said Debbie. "Not to be rude, but I have the impression that I understand men a bit better than you. Your dad's just having a bit of a mid-life crisis, and you can help him. You want to help him, don't you?"

"Yes," said Amy. "Yes, I really do. And of course you must be right, he's just got confused because of his age. It's like you said, he's having a mid-life crisis. You're right, I don't really know much about men and sex and stuff, but I do know that they have these mid-life crises. It's just his hormones, isn't it?"

"That's it. But you mustn't tell your mum about this. Not yet, anyway. Wait until it's all over and then decide what to tell her."

"OK, thanks. I wouldn't talk to her, anyway. She's always down on dad. Thanks, Debbie, I can tell you're a really thoughtful person. I'm so sorry that when I got your first email I replied so rudely."

"Oh, don't worry about that," Debbie said, inwardly wanting to punch the girl for her stupidity, as well as for her dismissive attitude to Carol. "I totally understand. But the important thing now is that we're going to make everything ok again. Girls together, right?"

"Girls together," said Amy, smiling weakly, unaware of the utter contempt Debbie felt for her as she did so.

After that, Debbie explained to Amy what she planned to do to 'uncross Tim's wires'. Amy was shocked at first, but as the conversation went on, she fell more and more under Debbie's spell. Although they were the same age, Amy could not help but recognize the other woman's far greater sophistication and, before long, she started to show an almost fawning admiration towards her. Debbie noticed, of course, and her contempt for the lumpy girl grew even greater, but she kept it well-hidden.

The conversation ended with Amy agreeing to be at Debbie's flat shortly before 6pm that evening. Once she had left, Debbie took out her phone and wrote a text to Tim.

"Hi Tim. Listen I think things have got a little out of hand. We ought to talk. Please come to my flat at 6pm this evening. Debbie xx"

She thought the kisses were a nice touch.

Her phone pinged.

"You told Amy. How could you do that?"

"I was upset. Sorry. I will put everything right this evening. Please come xx"

"OK"

Section 5: Debbie humiliates Tim and Amy

When Debbie opened the door of her flat to Tim he could not help, despite his anger towards her, feeling a thrill of lust. She was stunningly dressed in a lacy black basque, its thin straps a contrast to the luscious skin of her bare shoulders, and the cups of its bodice presenting her breasts like two ripe, juicy apples. Below its cinched-in waist, the basque gave way to suspender straps to which were attached black stockings, and over which Debbie wore black lacy panties. With her hair elegantly tied back and her face carefully made-up she looked, almost literally, stunning.

Almost immediately, Tim began to feel the stirrings of an erection but, when he entered the sitting room, he was shocked to see that his daughter Amy was there, sitting on the sofa, still dressed in her shapeless jeans and tee-shirt.

"What is she doing here?" he asked Debbie

"Dad, I have to be here," Amy explained. "Debbie and I have had a really good talk and she's going to help you to get over this."

"Tim, come and stand here, looking at Amy," Debbie said in a friendly voice.

She went and stood behind him, pressing her body close against his back, so that he could feel her breasts squeezed against him. She reached her arms around him, allowing one hand to stroke his chest and the other to move downwards, between his legs, feeling his erection through his trousers and encouraging him to hardness with the skilled, deft movement of her fingers.

"Now then, Tim," she cooed seductively. "Who is it you really desire? Who do you lust after? Who is it that makes your cock hard and hot and sticky? Is it me, or is it your daughter?"

"You, Debbie. Of course it's you," he replied hoarsely.

"But are you sure?" she pressed him. "What if Amy were to show you her undies? Wouldn't that get you going? Let's find out, shall we?"

That was the cue for Amy, as she had agreed earlier with Debbie, to stand up and remove her jeans and tee-shirt, returning to sprawl on the sofa in her bra and knickers. Debbie moved to sit beside her.

"Take your cock out, Tim, and start wanking," Debbie ordered.

Tim felt appalled at doing this in front of his daughter, but he was in state of such excitement that he obeyed. Besides, bizarre as it seemed, he thought he understood was Debbie was trying to do, and how he might redeem himself, in Amy's eyes, from the awful thing he had said about her yesterday. Debbie's next words seemed to confirm that.