Cougar Files: The Self-Esteem Rape

Judy took a deep breath at her front door. She was more nervous than she had ever been in her life. What she was about to do felt so wrong. It felt dirty. It felt naughty. It was the most exciting thing she had ever done in her life. Today was Judy's birthday and she had just turned forty. She officially felt old.

About a month before, Judy started thinking about what she was going to do for her birthday. In all likelihood, she thought, her co-workers would bring in cake to the office. There would be an extra long lunch break for everyone, and a few of her closer friends might give her a gift. Then she would come home to be ignored by her teenage kids and cook them dinner without so much as a thank you. After that, she would probably watch some shitty reality show on TV. Then she would go crawl into her empty bed and use her vibrator while thinking about her boss's twenty two year old son, Simon. Yep. She was in for another disappointing day.

However, Judy decided that she would change all of that. Who was to say that she couldn't go out and have some fun? So, she called her ex-husband and asked him to take the kids on her birthday. After several minutes of debating, he begrudgingly agreed. Her kids didn't really seem to care that they wouldn't see her on her birthday. Fuck it, thought Judy, they like their father and that whore that he's banging more than they like me anyways.

Next, Judy went out and bought a new outfit. She hadn't gone out in a long time, and she wanted all new clothes to look good in. She bought a new black dress that was skimpier than anything in her closet. She loved the way it showed off her legs without making her hips look too wide. Also, it pushed her tits together and showed off her cleavage while making them look nice and perky. Then she bought a new pair of high heels to match her dress and a new set of silver earrings. She spent a little more than she probably should have, but she wanted to look good.

Judy had always been attractive, but she was self-conscious about her age. Her ass had grown a bit larger, and her breasts weren't as perky as they once were. Her concern over her age was nonsense though. She was incredibly attractive. She didn't know it, but her son's friends constantly teased him about his MILF mother and her daughter was going through a rebellious phase because she didn't think she was as pretty as her mom. Judy had a whopping pair of d-cups that had managed to maintain their gorgeous shape over the years, amazingly losing only a bit of their perkiness, and a very sensual body that craned necks when she walked by. Her hair was a bright, shining blonde, and her eyes were light blue. But, when she looked in the mirror, all she could see was the things that hadn't stayed so firm over the years and all of the junk that was now in her trunk. However, Judy truly was still a hottie; not even just for a mother of two.

When she got home from shopping, Judy had put on all of her new clothes and stood in front of the mirror. Even she had to admit that she looked pretty damn good. It was the perfect self-esteem booster that she needed.

So, she had the whole night away from the kids and a new outfit all set to go out on the town. But, it wasn't enough. There was something still missing. In fact, it had been missing for a long time. The thing that Judy really longed for was the touch of a man.... That's putting it a little too softly. No point in dancing around it. Judy wanted some cock. It had been so long since she had been properly fucked. The last time she had gotten some dick was seven months earlier when she had drunkenly slept with somebody she had met at her office Christmas party. That wasn't exactly the best memory either. It wasn't until afterwards, while she was pulling her panties back up inside of the janitor's closet, that she had found out the guy was married to one of her co-workers. Her vibrator had put in extra overtime since then. Sometimes she felt like she should modify her monthly spending budget to account for all the D-cell batteries she went through.

She was definitely due for a good fucking. However, the thought of trying to pick up a guy at a bar just drove Judy crazy. Sure, she wouldn't mind bringing a guy home. That wasn't the issue. In fact, she really wanted to do that. The issue was Judy's self-confidence. She wanted a young stud to take home and ravage like a cougar, but, if she went to a bar, there would be all of those perky little twenty-something girls around her to compete with.

While she considered this, a wicked thought suddenly came to her. Lately, her imagination had been growing more and more. She had started fantasizing about sex and playing out fantasies while masturbating. She found that she had dark desires that were just now beginning to come out, no longer being suppressed in her mind.

It started of innocently enough. She had started by spanking herself while using her vibrator, imagining a large, masculine man holding her down. Occasionally, when the kids were at their father's, she would walk around the house naked, sometimes even venturing out into the back yard when it grew dark. She started watching pornography where women were tied up and told what to do. While watching these, Judy had discovered that she was submissive. However, even she didn't know how much, until she discovered that she had a rape fantasy.

Naturally, she was a little shocked to discover it. She almost felt some form of guilt, finding sexual arousal in such an act. Judy wouldn't have necessarily identified herself as a feminist, but she had always thought of rape as appalling at least. But, as she lie awake at night, fighting off the urge to touch herself, she found her thoughts unwittingly shifting. She imagined what it would be like to have a man force himself on her, overpowering her with his strength and having his way with her. She couldn't help breathing harder just thinking about it.

Judy wanted one thing for her birthday -- a nice cock. She also wanted to fulfill one of her darkest fantasies. And so, she decided that she was going to get raped. Not the real thing, of course. She didn't want to end up dead behind a dumpster or anything. But, she had looked into rape fantasy online and found that there were a surprising amount of women who were into it. The idea of a simulation rape made Judy bite her lip with desire.

She did some more exploring online and found a website where people post erotic personal ads. It seemed like a better idea than going on craigslist, so Judy made an account and posted an ad: "Mature woman looking for man to fulfill rape fantasy." Her ad wasn't even up for an hour before her inbox was filled with responses from men. About ninety percent of them could be thrown out right away. It was pretty clear that she shouldn't respond to them. After a couple of days of sifting through emails though, she finally found one that seemed alright. His name was Alex. He had a profile on the site and Judy checked it out. According to his profile, he was twenty-five, 6'1", with brown hair, and an athletic body. He even sent her a couple of custom pictures to prove he was who he said he was. Judy liked what she saw. Getting a response from someone so much younger than her was more than she could have asked for.

They exchanged a few emails, Judy told him the details about her fantasy, and a time was set. Judy was nervous about not really knowing the guy, but that also turned her on, knowing she was going to get fucked by a stranger. It was a reckless decision, but that was the point, right? She wanted her fake rape to be as real as possible.

Now, back to Judy standing at her front door. It was the night of her birthday. She was wearing her new outfit and she looked great. She wasn't even self-conscious about how she looked, but she was extremely nervous. How she looked wasn't the most important thing at that moment. The most important thing to Judy just then was a single thought going through her mind. If she stepped out the door, she would be raped by a stranger that night. Judy took a deep breath and held it. She opened her door, stepped outside, and locked it behind her. She smiled at this new adventurous side of herself.

She walked over to the cab she had called for earlier and climbed inside. She felt herself grow brighter as she realized the cab driver was trying to look at her tits with his rear view mirror. She was meeting a few of her friends downtown at a club. They were all around her age and mothers as well. It may have been Judy's birthday, but the night was an excuse for all of them to dress sexy and drink cocktails like they used to do in college. But, none of them were planning anything as.... ambitious as Judy had planned for the night.

At the club, all of the women were having a great time. None of them got to go out to night clubs as much as they used to, and they were taking full advantage of their night of freedom. The evening was full of drinking and dancing. At one point, Judy was dancing with a boy young enough to be her son. He made it painfully obvious that he was into her. Her girlfriends, knowing she hadn't dated anyone in over a year, tried their best to get her to go home with him.

"Who cares if he's a cougar hunter," said Judy's friend Heather. "Let him hunt you, and then devour him!" All of the women laughed.

Judy considered it, but then lied and said she would feel weird having sex with someone so young. Truthfully, she felt quite the opposite, but she didn't want to ruin her plans for later. It did feel good to be hit on by someone so young though.

Several hours and many drinks later, the women started to leave. One by one, they got into cabs and were whisked away back to their dull suburban lives. Judy hugged all of her friends goodbye.

"Happy birthday, Judy," said her friend Bonnie. "Sorry we couldn't get you laid tonight," she joked. The women, drunk on daiquiris, all started laughing.

"Well, you never know," said Judy. "I could always run into someone on the way home." Again, the women laughed. Judy smiled. If only they knew how right she was. Judy got into the cab and checked her watch. She had only ten minutes to spare. The cab zipped off and Judy abruptly told him to stop after only three blocks.

"Right here? You sure?" asked the cab driver. They were right next to the park. Judy took another deep breath to clear her head.

"Yes. I'm sure," she said. She paid the cab and walked into the park. It was dark and Judy was fairly certain that the park had been closed since 11:00. This was where she had told Alex to meet her. She didn't know exactly where he would be, but she told him to be somewhere in the park. She was going to walk around and, at some point, he was going to pop out of the bushes and grab her. Not knowing when or where it was going to happen added a sense of realism to the whole thing that excited Judy.

So, she began walking down a path. The park was fairly large. She had chosen it specifically because there were many trees and bushes to hide behind. At first, she had considered having Alex meet her at the club and rape her out back in the alley. But, the park seemed more secluded.

Judy's high heels clicked on the pavement beneath her with each step. Her ass swung temptingly back and forth, wrapped tightly in her black dress. Her large breasts bounced ever so slightly. It was a cool summer night with a slight breeze that cut through Judy's skimpy outfit, making her nipples harden slightly. Braless, her nipples pressed out against her dress. If it were lighter out, anyone would have noticed. She felt so exposed in the cool night air. She was vulnerable, out on her own wearing such a suggestive dress. At one point she passed by a group of teenage boys. They whistled at her and she could hear them saying some raunchy things as she passed.

She continued to walk around, her anticipation increasing exponentially. She felt herself beginning to grow wet between her legs just thinking about what she was doing. She had told Alex to be rough with her. She wanted a proper fucking. Just in case though, they had established a safe word, "ginger." Judy didn't expect to have to use it. Her pussy was craving a hard pounding and the drinks she had earlier only served to emphasize this.

Judy had just passed a large tree and was looking at some buildings off in the distance. She was completely caught off guard when she felt a man's arms wrap around her. One arm was around her waist and the other arm's hand was tight around her mouth. Judy yelped in surprise, but it was muffled by the man's hand.

"Don't even think about screaming," said a harsh voice in Judy's ear. Then, very forcefully, he dragged her off of the walking path and past some thick bushes. Judy tripped over her heels several times as the man moved her.

The man's left hand stayed tight over her mouth as he grabbed a handful of Judy's soft tits with his right.

"Oooooh," said the man in an almost taunting tone. "Looks like this dumb bitch has got some fat titties." He squeezed hard and pressed his crotch against Judy's ass. "What the fuck is someone like you doing walking around alone dressed like that?"

Judy said something in a pleading tone, but it was muffled beneath the man's hand.

"Damn, you really must be one stupid bitch. Don't you know there are bad men out here?" The man ran his hand all over Judy's body, squeezing a bit here, slapping a bit there. Judy tried to look back at the man, but couldn't see much. He was wearing a dark sweatshirt with the hood up. She could see the corner of a small tattoo on the hand over her mouth though. He seemed shorter than she had expected. He was strong though. A few times, Judy strained against his hold only to be forced back.

The man grabbed Judy's ass and gave one cheek a shake.

"You know what's going to happen now?" asked the man. Judy said nothing. The man tightened his grip and raised his voice. "I said, do you know what's going to happen now?" Judy shook her head no. The man laughed. He moved his mouth right up to Judy's ear and said, "I'm going to put you down on the ground. Then I'm going to take out my fat cock, and I'm going to fuck you with it." Judy strained against the man's arms and screamed into his hand. She may have been screaming no, but she had never been more excited in her life. Just hearing the man talk to her like that was sending shivers through her body. She had to hand it to Alex. He was really making everything seem real. He must have done a lot of role playing before.

"You're not going to scream anymore," continued the man. "If you do, I'm going to hurt you. Is that understood?" Judy nodded her head. "Good. I'm going to take my hand off of your mouth now. If you even think about screaming, I'll knock the wind out of you and the hand will go back. I have no problem fucking you with my hand over your mouth."

The man slowly removed his hand and Judy gasped for air. She whimpered a little, muttering a few soft pleas. This wasn't her first time role playing either. The man ignored her pleas. He reached down and put his hand up Judy's dress. He fished around, trying to find her panties so he could pull them down. All he got was a handful of Judy's soft ass though.

"No bra and no panties," said the man. "Bitch, I think you're just asking for it." The man then reached down the front of Judy's dress and pulled out her left tit then the right. Her large jugs spilled out easily, exposed to the night air. Then the man forced Judy down onto the ground, laying her flat on her stomach. He kept her pinned down with his body. With fierce haste, he hiked up Judy's dress, exposing her bare ass. Judy heard him make a hungry "mmmm" sound as he stared down at her vulnerable butt. Judy felt him doing something with his hands and then felt something large land on her left ass cheek. Her eyes widened as she realized it was his cock. It was massive. She could tell he was already hard as his cock rubbed against her ass cheeks.

Judy was thoroughly enjoying this, but the man had no patience. He lined up his giant prick with Judy's pussy and roughly forced it in. Judy was soaking wet by this point and her pussy stretched around the invading cock, swallowing it whole. But, the force of the man's initial thrust had been so violent and surprising to Judy. She yelped loudly, raising her head and instinctively trying to move away from the painful thrust. The man's hand caught the back of her head and forced her down into the ground again, smashing her entire upper body down. Her exposed tits and the side of her face were grinding into the grass and dirt beneath her. Judy had asked for rough and she was going to get it.

The man wasted no time before he started thrusting into Judy. Quick, violent strokes rocked Judy's pussy as the man selfishly took his pleasure.

"Oh God," cried Judy quietly. "Please. Please no."

"Shut the fuck up, bitch. Just be lucky your dumb cunt is so wet tonight."

The man continued pounding into Judy. Her body shook with each thrust, rubbing against the ground. She could feel her ass shake as it took the brunt of the man's force. She loved the feeling. Judy was a successful business woman and a mother of two. But, tonight, she was just a dirty hole for some stranger to fuck.

"Oh, fuck yeah," said the man. "Fuck yeah. Take my dick you stupid bitch." The man wasn't pacing himself at all, looking to get off quickly rather than take his time. "Jesus, you're so fucking wet," he said, legitimately surprised. "If I didn't know any better, I'd say you really did want this." Then he quickly stopped and slid his cock out of Judy's pussy. His veins bulged, echoing his primal desire.

"Let's see what else you want," said the man in an evil tone. He spit into his hand and Judy felt him wipe it into the crack of her ass, spreading it around her asshole. Judy felt a sudden sense of panic as she realized what the man intended. She waited to see if she was right though. No need to spoil the moment if she was wrong.

It wasn't as though Judy was a complete stranger to anal sex. When her marriage had begun to sour, she had let her husband fuck her ass many times thinking it would spice things up. But, that had been over five years ago, and the man holding her down had a much larger cock than her ex. The man lined his cock up with Judy's asshole.

"No. No no no no," said Judy. "No. Not in my ass. Don't!" She had gotten a little too loud in her protests and the man's hand quickly clasped around her mouth, muffling her pleas.

"You'll shut the fuck up if you know what's good for you," said the man, and he thrust into Judy's ass. Judy's eyes shot wide open as a few inches suddenly burst their way through her puckered asshole. The sudden pain from the unanticipated cock shot through her body and she struggled beneath the man truly trying to get away. She tried to scream "Ginger! Ginger!" into the man's hand, but it was muffled and inaudible.

The man continued to slide inside of her ass, and Judy felt as though her insides were shifting to accommodate the huge prick. Luckily, the man's cock was very slick from Judy's gushing snatch. Without that and the saliva lubing her ass, it would have been much worse. Even so, it was still fairly painful, yet Judy felt a strange pleasure in being used like this. She stopped trying to yell ginger and concentrated on relaxing her asshole. Her eyes welled up a bit, but she didn't cry.

The man was only halfway inside. He started thrusting in and out quickly with no regard for Judy's comfort. He hadn't been fucking her ass for very long before he stopped abruptly. Judy felt his body tense and he reached down to grip his cock in his hand.

"Oh shit," he said. "I'm gonna cum." The man pulled out of Judy's ass and quickly stuffed himself back into her pussy, immediately pounding away at her slick hole after he had just been halfway up her ass. Holy shit, thought Judy, is he really planning on cumming in my pussy? She screamed into the man's hand and tried to wriggle away. But, the man was too strong, and the feeling of her pussy getting slammed hard was just too much pleasure for Judy to deny. She felt her body begin to tense up. She was going to cum soon. She was going to cum while a stranger raped her!