She’s a Mad, Mad MILF

Jennifer Romaine was deep in the midst of a life crisis.

She had dumped her skeezy boyfriend, Mike Willis, two weeks ago. Jennifer initiated the breakup, despite Mike’s brooding good looks, not just because she felt he was lacking in direction and ambition, but also because he was getting significantly creepier by the day.

He had lost his sales job, which could happen to anyone, but he didn’t seem to care in the slightest. He had no plans or ambition. He wasn’t even trying to find anything else. All he cared about were video games, beer, football, hockey, and his lame, immature friends.

And pornography. That, of course, was the creepy bit.

The case against Mike was open and shut:

He had borrowed money, significant money, from Jennifer to pay his bills and seemed to have no intention of repaying it.

He always had time and money to go out and drink beer with his jerky friends, but he always balked at doing anything that would cost money with her.

Her thirty-sixth birthday came and went absolutely unnoticed. When she finally called Mike on this, he ran out to and bought her a hot pink vinyl bustier with black trim.

But the biggest red flag was the fact that his collection of pornographic films and magazines was growing at an alarming rate. Not that Jennifer was a prude, in fact she would watch movies with him from time to time in an effort to share intimacy and to spice things up between them, but she felt like it was getting out of control. His requests in the bedroom were getting stranger and more extreme: props, role playing, urination. She walked in on him masturbating more and more often. He was going through lube at an alarming rate.

His affinity for pornography was definitely becoming a cause for concern. But it wasn’t until Jennifer discovered that Mike had secretly recorded the two of them having sex that she felt he had irrevocably crossed over into the land of slime and sleaze and wanted to permanently end her association with him.

She had  only accidentally discovered she was being taped when she walked out of the shower one morning to find him kneeling in front of the television, dick in hand. She rolled her eyes and was prepared to just write the incident off as another example of his...eccentricity... when she noticed it was an image of herself on the television on all fours wearing the ball gag in her mouth that Mike had come home with one evening and insisted they she try.

Needless to say, she was appalled. There was much wailing and crying. Electronics and other breakables were tossed about his apartment and smashed to pieces. She made Mike give her the DVD and watched him delete the file from his computer. Then she told him it was over, that she never wanted to see him again.

That was all bad enough, but what happened next is what really caused Jennifer’s crisis.

Jennifer got an email from a friend of hers with a movie attachment. She double clicked on it and found herself watching her and Mike having intercourse. Apparently, there were other copies of other sex tapes featuring the two of them that Mike had not erased.

She screamed.

After the initial shock had passed, she called her friend and asked her where she got the video.

“You know Paul, that guy I work with that you met at happy hour a couple of weeks ago?” Jennifer said yes, she did remember Paul. “He found it on a website.”

“WHAT website?”

There was a pause. “He said a friend forwarded it to him...um...that it was on a site called ... um ... well ... hotmilf.com.”

“WHAT?!?!”

Jennifer was speechless. She didn’t know what to say. She was mortified.

“But I’m only 36. I AM NOT A MILF!!!” she screamed into the phone and hung up on her friend.

She immediately went to www.hotmilf.com.  She found three videos featuring her and Mike in the act.

She guzzled down a bottle of red wine, took an Ambien, and fell asleep on the couch, crying and angry.

The next morning, she got up and checked her email. Other people had seen the videos of her (or told her they had “friends” who had seen videos of her) on other sites: www.kinkymatures.com, www.cougarsden.com. The worst: www.dirtysoccermoms.com.

She called in sick to work. She thought she detected an odd tone coming from her boss, and she wondered if he had stumbled upon any of this ...; she had always suspected him of being a pervert.

People were disgusting.

Jennifer was absolutely, thoroughly mortified. Humiliated. She didn’t know what made her angrier, the awful violation of her privacy or the fact that she was being classified by numerous smut outlets across the Internet as an older woman.

The double standard was also infuriating. If a 36 year old man was recorded having sex, would he be featured on manthers.com or dirtyoldmen.com? She didn’t think so. What woman would tape her boyfriend having sex without his knowledge or consent?  That would never happen.

Men, she decided once and for all, were pigs.

Jennifer silently weighed her options. She knew what she ought to do was call the police. She should have that asshole thrown into jail where he could be gang sodomized by a group of hardened convicts. She wanted him to feel the same kind of shame and humiliation she was feeling, the same kind of violation.

But she was too embarrassed to call the police. She didn’t want anyone else to see these videos. She didn’t want to have to sit across a desk from some police MAN and explain what had happened. He would want to see the videos. He would judge her and think she was a whore. He would probably want to take her in back and strip search her.

Jennifer was seething. She wanted revenge. She wanted to put him on display doing something so humiliating, so vulgar, that it would make what happened to her look like just another ordinary breakup. She wanted him to learn, once and for all, not to mess with her.

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Mike Willis was drinking with his friends at a bar called the Kitty Kat Club on the west side. The bar was famed for, among other things, the short skirts and ample chests of the wait staff.

Mike, who was on his seventh Budweiser, was particularly enamored with a petite brunette waitress wearing knee high socks and pig tails. He had been ogling her all evening, making remarks every time she passed by their table. The waitress, who was sadly used to this sort of behavior from the “gentlemen” patrons, smiled and took it in stride, though she secretly loathed him.

Then Mike noticed a statuesque blond at the bar. She was stunning. Long blond hair, tiny waist, enormous breasts. She was looking straight at him.

Mike looked down at his beer. He waited a few seconds, then looked up again. She was staring at him. She smiled.

Mike raised his eyebrows as if to ask “who, me?” Ever so slightly the woman’s sultry lips puckered.

Cha-ching.

Mike got up and walked to the bar. He was standing right beside her. She was taller than he had thought at first, close to six feet. She smelled like lilacs.

“Can I buy you a drink?” he asked coolly.

“Of course you can,” the woman replied. She had a sexy, husky voice. That fantastic smiled beamed forth from her gorgeous face.

“What would you like?”

“Gin and tonic with lemon,” she told him.

Mike flagged down the barkeep. He ordered a gin and tonic with lemon and another Budweiser for himself.

“So what’s your name?” he asked as he slid her drink across the bar to her.

“Samantha,” she purred. “What’s yours?”

“Mike,” he replied staring at her breasts beneath her sweater.

“What do you do, Mike?” She took the straw deliberately between her lips and took a long sip from her drink.

It took a moment for the question to travel from Mike’s ears to his brain. Then, as if woken from a dream, he replied with a rehearsed response. “I used to sell industrial semiconductors, but I got tired of that racket. There’s a lot of money, but it’s real competitive. Lots of overseas travel. Not a lot of time for life, ya know? Right now I’m at liberty,” he smiled. “Taking some time to enjoy life.”

“That sounds fascinating,” Samantha told him with a little wiggle that made her chest bounce.

“Not really,” he replied then took a pull off the long-neck bottle of beer, never taking his eyes from Samantha’s chest. He had been through this spiel a hundred times with a hundred different chicks. He felt like he had never done it more smoothly than right then.

“I think I’d like to get into something totally different,” Mike told her. “Maybe advertising.” He was almost ready for another beer. “What about you?” he asked. “What do you do?”

“As little as possible,” she said. Then she batted her long eyelashes at him.

There was a pause

“Do you wanna get out of here, Samantha?”

“I thought you’d never ask,” she said.

“My place or yours?”

“Definitely my place,” she purred. “It’s just around the corner.”

Cha-ching.

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Mike awoke with a splitting headache. It was pitch black. He didn’t know where he was. He was confused. He was also sore. His back hurt. His throat felt impossibly dry, like he’d been eating steel wool. What the fuck was that in his mouth? What was going on. He couldn’t move his arms or legs. He was restrained, his ankles and wrists tied down. His head was restrained and he was lying chin-down on something cold and hard.

What the hell was going on?

He started to struggle. He was panicking. 

The lights came on. They were blindingly bright. Mike blinked, trying to adjust. He was almost instantly aware that he wasn’t alone. He detected perfume that smelled like ... lilacs? Then he remembered Samantha.

“Good morning, Sleeping Beauty,” she said. She was sitting in chair across the room from him beside a large flat screen television. The television was switched off.

What the fuck?! he wanted to say. But there was something stuffed in his mouth restricting his speech. He was angry and terrified at the same time.

“I’m so glad you could come here tonight,” she said with a smile. “I’m really going to enjoy this.”

Mike was trying desperately to understand what was going on. He remembered getting in a taxi with Samantha. He remembered fooling around in the cab. He remembered fooling around in the elevator up to her apartment. He remembered fooling around on her couch and drinking wine.

The wine.

He had been drugged. He knew it instantly. That’s why he didn’t remember. That’s why he felt so hung over with the headache and the soreness.

What the fuck was going on? He started to struggle against his bonds again, and to mumble through the gag. “You fucking bitch!” he was trying to say, but no intelligible sound could be heard.

“Easy, boy,” purred Samantha. “You’re going to need your strength.”

He was beginning to become more aware of his surroundings. He was in a brightly lit room, strapped down to what felt like a metal table. The only things visible to him were Samantha, her chair, and the television she was sitting beside. There was nothing else. What the fuck was he wearing? Something unfamiliar...he couldn’t tell. There was something around his face ... a wig?

Jesus Christ.

“I’m going to step outside for a minute, beautiful,” Samantha said seductively. “There’s something you need to see and I think it’s best that you’re alone.”

Samantha flipped on the television. Then she blew Mike a kiss, winked, and walked out of his field of vision. He heard a door open then close.

“Hello Mike,” said a familiar voice.

Jennifer’s face was staring back at him from the television.

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So here we are at last.

I’ve been preparing for this moment for the past four months. Planning out every little detail, working with every breath since that awful day that I found out what you did to me.

It’s bad enough that you taped us having sex, you horrible, disgusting little pervert. It’s bad enough that you did it without my knowledge and that you then chose to expose me, publicly, in such a thoroughly humiliating way. All that is bad enough.

But how could you post it on those awful websites, you disgusting little shit? You knew I had just celebrated a birthday, and that I was feeling particularly sensitive, that society makes single women over 30 feel like there’s something wrong with us if we’re not married and raising kids, so you chose to lash out in the most hurtful way you could imagine.

That just goes to show what a disgusting little parasite you really are.

But I guess what hurts more than anything is that I trusted you, Mike. I trusted you and you violated that trust in the worst, most disgusting way your little brain could muster. I feel so stupid and angry with myself. But that doesn’t compare with the anger I feel toward you. I’ll never forgive you and I’ll never trust another man again. Ever. You took that from me and now it’s dead. There’s no going back.

But you crossed the wrong woman, Michael.

I know, having been with you as long as I was, what you’re insecure about. I know what your demons are. I know all your macho bullshit posing, your obsession with sex and cock and pussy, I know, deep down, what it’s all about. It’s a classic case of overcompensation.

You’re insecure about your manhood, Mike, aren’t you? Aren’t you? You feel like you always have to prove what a big man you are to everyone. You feel like by fucking women, by humiliating them, by spending your time looking at pornography that that makes you a man.

But really you feel scared. You feel unsure of yourself. You feel like people are going to think that you’re not manly, in that stereotypical, bullshit 1950s way. That’s your ultimate fear. You worry that people are going to question your manhood and your sexuality.

I’m going to parade your demons in front of you and hurt you with them worse than you’ve ever been hurt.

Mike heard the door open behind him. A man walked in and sat down in the chair beside the television screen. He was thin, with tightly cropped blond hair and delicate features.

Then Mike smelled it. Lilacs.

And he knew this was Samantha. That Samantha was, in fact, Sam.

You’ve already met my friend, Sam. He helped me put this whole thing together. Sam’s an amazing guy. He’s also filthy rich, extremely well-connected, and very, very powerful. Sam helps people with their problems, but he doesn’t come cheap. I sold my condo to pay for Sam’s services. And it was worth every penny.

Sam smiled at Mike and winked. He still had those long eyelashes. Mike felt the heat rising in his cheeks.

When I first explained to Sam what you had done to me, his advice was to think up the most awful revenge I could imagine and then pay him to carry it out. I asked him how we’d possibly get away with it. He explained to me that if you have the right dirt on the right person, if you can apply the right kind of pressure, you can get away with anything.

Sam pulled a remote control out of his jacket pocket and the image on the screen froze.

“Here’s what’s going to happen, Mike,” said Sam crossing his one leg over the other as he sat calmly. “I’ve got undeniable evidence that you were the one who posted the videos of Jennifer to those websites. So you can go to jail for that and we can sue your ass off to boot. But that’s not what we’re going to do unless you force our hand.”

Sam hit the remote again. Jennifer’s face went back into motion.

Every time you meet a woman, I want you to wonder if she knows. If she’s seen this. Every time you go home with a woman I want you to think, ‘Dear god, is this woman going to do something awful with me? Can I trust this person?’

I’m taking your dignity from you, Mike. And, hopefully, in the process, I’m going to do to you what you did to me. I’m going to make it impossible for you to ever trust anyone of the opposite sex ever again.

The door opened once again. Mike could feel other people—plural—entering the room, but he couldn’t see any of them because of how he was restrained. Mike could see Sam stand, saw him take something else out of his pocket, and place it on top of the television. He connected a cable from the television to this object. Mike then saw a blinking red light emanating from the object, and suddenly the image of Jennifer on the television was replaced by an altogether different, disturbing image.

Mike saw himself strapped face down on the metal table. The wig Mike had felt around his face and on his head was a long black woman’s wig. Mike could plainly recognize his own face under the wig, with a ball gag in mouth. Only it wasn’t an ordinary ball gag. It was shaped like a red apple.

He was also wearing what he could tell was a dress, with big puffy shoulders and a high, white collar. As the seven dwarves closed into the picture around him, he realized in horror that he was dressed as Snow White.

“We know how much you like video tape, Mike, so we’re capturing this for posterity. And if you go to the police, or anyone else, this tape is going to be all over the Internet faster than you can say, ‘happily ever after.’ Got it?

Mike got it all right.

One of the dwarves hiked up Mike’s dress.

“Alright boys,” said Sam. “You can begin.”

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