Emily needs to make a dirty video with a stranger in order to get into her new sorority. She finds a willing middle-aged man. As eager as he is to help her he has his own ideas about how to use the situation for his own benefit. (Part 1 of our three-part “Sorority Pledge Series”)
Mark looked out the window of the coffee shop, across the road, to the polo pitch where a few well-heeled participants galloped and practiced. Horses, they were everywhere out here. They were part of the fabric of life in this rich enclave just outside of the city.
Across from him sat a young woman 25 years his junior. Her name was Emily and she was spending far too much time distracted by her phone.
Mark was 45 and recently separated. He had joined an online dating app a few days before. Emily had contacted him just a few hours ago. He wasn’t particularly interested in younger women, but she was pretty, fresh, and more importantly, wanted to meet up today.
It was really the urgency that spurred him on. He felt he needed that in-person human contact and needed it now. An hour in the youthful energy of a young lady with few cares would do him some good.
He had no idea what to expect from this half-girl/half-woman. He had gotten enough information from her to be able to creep her online and confirm she was of age before he left to meet up with her. At least he wouldn’t have to worry about being arrested.
She certainly didn’t dress up for the meeting. She was sitting there in sweatpants and a baggy sweater that proclaimed the name of the local prestigious college on the front. Her reddish-blonde hair was put up in a long ponytail. Between her expensive shoes, flawless white skin, and the fact she lived in this enclave of the horsey set, he felt she probably came from the best of families.
“So you’re not some kind of creep are you?” She asked. Looking up from her phone momentarily.
“If I was, would I admit it?” Mark replied. He was a bit concerned that she was too trusting.
“Ha ha, I guess not,” she said nervously. Her phone pinged and she picked it up once again. Mark was getting annoyed, the entire conversation had been like this.
“Oh shit,” She said looking at the incoming text. “Fuck I’m falling way behind.”
“What is it?” Mark asked.
She looked up at him and he could see the fear in her eyes behind her false confidence. She was sizing Mark up for something and quite not sure if she’d regret it later.
“I need you to help me.” She said.
Here it comes, Mark thought. Some sort of scam.
“I hope you don’t mind,” she added. “It’s well… It’s Alpha Pi Phi.”
“A sorority?” Mark asked.
“Yes. It’s initiation. There’s a number of us. We have to go out and find a guy and take the dirtiest pictures or videos that we can. We arent’ allowed to use our boyfriends. The girls with the best photos get in the chapter. I thought it was a laugh and didn’t think anyone would actually do it, but it’s true. All the other girls have got something and we’re meeting in just over an hour. Would you mind helping me?”
A warm numbness spread down Mark’s spine as he took this in. Was this a put-on? The girl looked deadly serious. Her voice was remarkably casual.
“Sure. What kind of photos?”
“Whatever you can think of. I can blow you, you can fuck me. The dirtier the better. Maybe you have some ideas.”
Mark certainly did. He’d heard about these kinds of initiations, but never thought he’d be part of one, especially at his age. The whole idea of sororities and fraternities went against the grain of his internal culture. Why would you do humiliating things to yourself or others just to be part of an exclusive group of unlikeable people?
On the other hand, was he willing to take advantage of the situation and have his way with this spoiled and status-seeking little rich girl so that she could join her precious group? Absolutely.
He was a prop and was being used. He knew that. But he was also using the situation to get what he wanted. If she was going to casually fuck a stranger, Mark was going to make sure she got fucked. The idea of ravaging what was no doubt a tight little inexperienced pussy and fucking that inexperienced mouth had its satisfaction.
She pressed him about the time, so they got in his car and took off into the rolling hills. It was hard to take good photos in the car he said. Not enough room. In actuality, he wanted to take advantage of this opportunity as much as he could. The car just wouldn’t cut it.
As Mark drove, Emily told more of her story. Yes, she had a boyfriend of sorts, but he was still very much a boy. Awkward, shy, and more interested in throwing the football around with her than anything else. She’d had sex a few times, but it never lasted more than a few minutes before he came. And her boyfriend thought oral sex was gross so they’d never done it. My God, thought Mark, imagine not wanting those cute little lips around your cock. Some boys were so weird.
“I’m going to be honest Mark,” she said earnestly. “I need your help. I’m not very experienced. You’re going to help me right? We’re going to be really dirty and get those photos so I can get into Alpha Pi Phi?”
“Oh we certainly are,” said Mark.
“We need to be quick though. Where are we going?”
Mark pulled into a stretch of abandoned roadway that led off the two-lane highway to a now-closed gravel pit. About fifty yards down he stopped and they got out. The highway was still in the background.
“I need to be back at Jacob’s Park near the coffee shop by 3pm.” she said looking at her phone. ‘We’re not going to make it.”
Mark did the math, he’d only have about 15 minutes with her and would have to speed back. He’d use his time wisely.
“We’ll get you back in time. Get out.”
He watched as she got out of the car and noticed a large wet spot on her grey sweatpants between her legs. He looked down at the seat. Dampness was evident. This girl was certainly wet and ready to go. That would make things easier for time.
“Off with your clothes,” said Mark.
As he looked at her she was suddenly playing demure. Her hands crossed her body in an X as if she was shielding herself from his gaze
“Do I have to do it all the way?” What if I just pulled my pants down a little.
“I thought you wanted to win?”
“I do, but I don’t really know you and we’re outside and all.”
These spoiled brats thought Mark. All talk.
“What if you came with me to the meeting and told them we did something but that my camera didn’t work?”
Mark responded: “What if I told them the truth, that you copped out and are trying to lie to get in? I’m sure that will go over well.”
He crossed his arms and held his gaze firmly on hers.
A few seconds passed. They seemed like hours. The sun was beating down between the double line of trees on either side. The summer sound of birds and insects echoed from the long grass at the side of the road. Emily looked back at the highway. Yes, the car could be seen from the road but only for a few seconds.
Finally, Mark said, “Forget it, I’m leaving. Good luck explaining yourself.”
“No,” she shouted shrilly. Finally adding, ‘Help me!”
Mark spun around and grabbed her, yanking her bottoms down and spanking her young ass. He liked the sound, and it got her attention. He took both of her arms and raised them up quickly, then reached down to the bottom of her sweater and yanked it off as he heard her yelp.
“Shut up!” shouted Mark. “I’m going to do exactly what you need. If you want this done in time don’t argue with me.
She had no bra and her breasts bounced as the sweater came off. They suited her athletic frame and had small but very hard nipples that poked outwards.
Mark picked her up and sprawled her out on the hood of his car, yanking her sweatpants and lace panties from her ankles. He could feel their dampness in his hands.
Grabbing her camera, he did the first of her pledge videos. There she was, sprawled out totally naked on his car. He got her innocent-looking face, tanned body, and very white tan lines around her breasts and bikini area.
The area between her legs was so white and smooth and so incredibly wet, he paused the video for a moment and leaned over to taste her, driving his tongue into her and feeling the smoothness around his lips. As a matter of habit, he was about to tease her clit and then remembered this wasn’t about her pleasure at all. This was a job on a deadline.
He focused the camera on the area between her legs and took his sizeable cock out of his pants. Yes, he may have a Dad bod, but this dick was as solid and probably the biggest one she’d have in a while.
He paused his entry for a second to build up suspense. The look of his fat dick with its big purple head, about to violate this young, sweet, but ready womanhood was arousing in and of itself. He pushed in and slid slowly back and forth, while Emily gasped and moaned audibly. Then he pushed forward, totally inside her. It had been a long time since he’d been in a woman this tight and the pressure around his cock made him feel huge. He angled the camera slightly to show his balls pressed up firmly against her ass.
Emily was whimpering and obviously wasn’t used to it. He turned off the camera and slid out again.
“Did you get it?” Emily asked. “We need to go.”
“Not yet,” said Mark. “We’re going to make sure you win this. I told you I’d help you and I will.”
“Down on the road on your hands and knees.”
She got down and realized there were small bits of gravel. She complained and tried to get up, but Mark’s arm held her down.
“My knees hurt,” she said.
“I don’t care,” said Mark, as he spanked her young bubble ass. “You’ll thank me later.”
He picked up the phone and began recording a wide shot to show it was indeed Emily here on her hands and knees on this dirt and gravel road. He made sure to show her dangling breasts and then focused on her ass cheeks and pussy as he slid his hard cock inside again. She had already loosened up a little and he began to get into a rhythm. He reached over and grabbed her ponytail for leverage and started pounding her cheeks with his thighs. Tilting the camera up slightly he realized he could get the reflection of Emily being fucked on the side of the car.
The squeezing of her pussy was tremendous, which made him feel harder than he’d ever felt before. He was getting into watching the scene on the phone.
Here he was a middle-aged man, fucking this stranger young enough to be his daughter in the middle of the day, on the side of a road, and for what? So she could join some stupid sorority. A group of other well-heeled young women who had also been out fucking complete strangers. It was oddly appropriate, thought mark.m Emily would probably spend the next four years at College being chased by guys who had done equally stupid things to get into their own fraternities
But she wouldn’t belong to them. She’d be his. This was her first proper fucking and the circumstances were dirty, twisted, and dangerous. She’d remember it forever. What would she when she looked back on this as the years passed? After getting married, having kids, or being promoted to a responsible and prominent position in some important organization? Would she feel thrilled? Humiliated? Regretful? Perhaps all three. He’d have this moment over her for the rest of her life. And all the while she thought she was using HIM.
He became suddenly aware of the loudness around him, of the smacking of thigh against ass, and in particular Emily’s screams. He noticed the ache in his own thighs. It struck him that he had been fucking her much much harder than he realized.
He turned off the video and slowed down. He could probably give her an amazing orgasm, but there was no time for her pleasure.
Emily collapsed onto her ass and then put out her arm to push herself up to her feet. Mark pushed her back down again.
“But we have to go!” she shouted.
“In a minute,” said Mark. “This next video will guarantee you’ll get in. We only have one chance so do as I say now.”
Mark placed her phone on the back bumper and switched the camera to screen-side so he could see the framing. At this angle, you could see from Emily’s breasts up to the top of her head. Mark was standing in front of her. His upper body and face was out of the frame.
There was something about the contrast of the tanned, fit young athlete and his pasty white skin and softer body. But his cock was anything but soft. He had weeks of loneliness built up and that tight pussy had primed him perfectly.
“Suck me” he commanded. She paused and then did so. Mark grabbed her hair and forced himself into her mouth. The sorority girls wanted something dirty did they? He’d give it to them, including a running commentary.
“Look into the camera so they can see how much you want in this sorority. You’re letting a 45- year old man fuck your face in broad daylight on the side of the road. Look at your friends in the camera. Oh yeah stare right in there.”
Mark looked down. Emily was wide-eyed and her face had a level of both humiliation and surprise as she stared at the camera. What had she been expecting? he wondered. Probably not this. But he did promise to help her make the dirtiest video possible so that she could get in. He was going to be good to his word. He remembered the old adage ‘be careful what you wish for.”
He continued his commentary. “If you want in Emily you’re going to have to do exactly what I tell you. Okay. Do you understand?”
A loud gurgle came from Emily’s throat as Mark penetrated her mouth again and again.
“I’ve got a big fucking load coming soon. I want you to take it all and swallow it. I want your friends to know this is your first time. And you’re going to swallow the sperm of a man old enough to be your Dad. Yeah, keep sucking. That feels so good. Once you’ve swallowed I want you to look into the camera and tell them it was worth it to get into Alpha Pi Phi. “
His thrusts were getting faster and deeper as he continued his commentary.
“Every time you’re at a sorority party or even see those Greek letters, you’re going to think about being taken by me, taking my cock into your pussy, being facefucked on camera and swallowing my load. And it’s going to be a big one Emily. Here it comes. Tilt your head back, open your mouth and stick our your tongue.”
The cry from Mark’s orgasm filled the air as Emily felt the pungent cream, splatter on her tongue in thick spurts. It coated her mouth quickly and began to drip down out of the corners of her chin.
As Mark finished he looked quickly at his work. Her small tongue was coated and his sperm had settled inside of her mouth almost up to her teeth. It had been a while since he’d let loose and it showed.
Emily’s face was contorted in disgust, her eyes closed and squinting. She was beginning to let the sperm run down her face
Mark quickly leaned over and closed her mouth by pressing up lightly on her chin.
“Look at me. He said. She looked up into his eyes.
“Now swallow it!”
He tipped her head back and saw her adam’s apple move. She began to cough. Mark wondered if the thickness of the load had made it difficult to swallow. Emily’s hands started shaking in mock distress as she puckered her face. The taste of sperm was clearly not endearing to her. Her high-pitched moan suggested a girl being forced by her friends to eat a sour candy. It was a metaphor that was a bit too appropriate thought Mark.
“Now let your friends know it was worth it,” he said.
Reluctantly Emily leaned toward the phone camera. Hands still outstretched, stray cum trickling down her chin. She made a face, looked at the camera and said, ‘It was worth it. This is my commitment to Alpha Pi Phi.”
Mark reached out and touched her hair in a gentle manner and said, “Good Girl.”, then picked up the phone and switched the video off.
He helped Emily up off of her knees. She made a sound with her mouth like she was still trying to swallow then coughed.
Marked ignored it. “You’re sure to get into the sorority now. I told you I’d help you.”
“Yeah,” Emily countered. She was avoiding looking him in the eye. “We need to go.”
“We still have time to make it,” said Mark. Emily was looking around for her clothes. He watched her bend over to grab her sweater and got another view of her athletic ass and that fresh, smooth, and tight little pussy. He was already hard again. As he watched her climb into her sweatpants he said, “So, are you going to thank me?”
She looked up at him. His cum still drying on her face as she frowned. After a second she looked away and murmured “Thank you, Mark.”
Once inside, Mark put the vehicle in gear. Emily began coughing again and whined slightly as she breathed as if asking for sympathy. There was none from Mark. She’d gotten exactly what she wanted.
“Do you have any tissues Mark?” she asked. “I want to wipe my face.”
Mark indicated the glove box, but when she checked there was none to be had. She wiped her face with her grey school sweater. Appropriate, thought Mark. Starting your sorority out with cumstains on your sweater was probably a rite of passage.
Mark gunned the engine to get to the park on time. As they drove Emily opened up.
“Oh my God that was horrible,” she said. “Can we stop? I need a coke or something.”
“I can but it’s going to make us late. You don’t want to be late do you?”
Emily looked at the time on her phone and sighed. “Fuck…”
“That’s okay we’ll get you there,” said Mark supportively. He liked the idea of his aftertaste in her mouth for the rest of the afternoon.
For the next few minutes Emily scanned the videos on her phone. He looked over to see her expression. Her mouth was agape as she saw the results of what she’d just gone through.
“Hey,” said Mark. “You acted like a real porn star. You’re sure to get in.”
The realization that her entry into Alpha Pi Phi was now certain, seemed to soothe her. By the time they got to the park, her mood had shifted. Her energy returned and she was upbeat the moment she identified the van that contained her new friends. As Mark parked beside it, Emily made a request. Would he come with her? She thought it would improve her chances.
It seemed a dangerous thing to do, but Mark said yes. After all, he was still horny and was rather fascinated to meet the other well-bred girls who had just fucked strangers in order to fit-in to their new group.
The sliding door of the van opened and the sound of hysterical giggling could be heard from the three occupants. There was a tall, long-haired slightly older blonde with perfectly manicured nails named Jessica, there was also a chubby, but cute Latino girl named Felica and a buxom, but shy Mulato girl named Molly.
Emily quickly blurted out to everyone, “Hey guys, this is Mark – he was my date this afternoon.” adding. “Obviously, he’s NOT my boyfriend.”
Jessica laughed, “OMG, we thought you’d brought your Dad! We figured we were all busted!”
Mark blushed for a moment and then smiled. Yeah, he thought, I guess I am old enough to be your dad but I just fucked one of your friends.
Instead, he simply said, “So this is Alpha Pi Phi”
“Oh hardly,” said Jessica from the front seat. I’m the only member here, the three girls are pledges. We’ll have a bunch of other groups arriving here in the next half hour – then we’ll officially decide which pledges get in.”
This whole thing was perverted and twisted, thought Mark, but Jessica was treating it like it was the most natural thing in the world. He wondered what SHE herself had done to get into the club.
The back of the van had both rear and front-facing seats. Emily sat next to Mark, but across from him. Eye to eye was Molly. The innocent-looking Mullato girl with big dark eyes and long black hair was staring at him in the most uncomfortable way. She looked vaguely familiar but he couldn’t place her. He didn’t exactly know a lot of 20-year-old women.
For a moment Mark wondered just what the fuck he was doing there. The situation was already crazy enough. Why the hell did he get in the van? Then he took a breath and looked at the young women around him. They had all recently been on a journey similar to Emily’s and were about to show proof of their escapades. In many ways, it was every man’s dream. Why the hell shouldn’t he enjoy it?
“Okay, Ladies!” Jessica announced in the manner of a sports coach. “It’s time to turn in your phones and see what you’ve got. Molly, you’re going first.”
Molly kept her gaze on Mark, though he noticed her eyes took on a guilty look. She was hesitant at giving up the phone, Perhaps she was embarrassed at Mark seeing what she had done to get into the sorority.
“Come on Molly, give it up!”
Molly slowly opened her phone to the photos app and passed it to Jessica.
“This is SOOOO LAME!” she said, flipping through the photos. It’s just you standing next to some guy with his shirt off.
The Latina girl chimed in, recognizing the guy as Molly’s boyfriend. Jessica shook her head in disappointment and handed the phone back to its owner. Molly gave Mark one more glance before she looked away embarrassed.
“The rest of you better have a LOT more than that if you want to get into Alpha Pi Phi,” stressed the blonde. She called out Felicia’s name next and the chubby girl surrendered her phone. “I decided to do a video instead,” she announced.
Jessica pressed play and the inside of the van suddenly came alive with the sounds of furious sex, thigh smacked against cheeks and Felicia’s moans echoed through the vehicle. The phone got passed around.
“Oh my God is that your pool guy?” said Emily.
“Yep,” said Felicia, “And I’m taking it in the ass.”
Mark saw a streak of deep embarrassment suddenly cross Felicia’s face as she made eye contact with him. She had forgotten he was there. It was one thing to say and do these things with the girls, but having someone’s “Dad” there was another matter.
Mark was given the phone in turn and watched the video closely. They’d propped the camera up on the pool deck to get a clear view of Felicia’s face and ample body, large breasts swinging as she was smashed from behind by a pale young guy in a corporate logo polo shirt. The dude had taken the woven belt from his shorts and put it around Felica’s neck – riding her like one of the local horses.
It was then he thought of Felicia’s mother. What would she think of this scene? A 45-year-old man watching her well-mannered daughter get fucked by her pool guy. And how much was she paying for Felicia to get into this prestigious college? Did she know how high the price would ultimately be? Had her mom fucked her own stranger 20 years ago so that SHE could get into a sorority too?
He smiled and handed the phone back to her. “That’s pretty fucking hot!” he said.”You have gorgeous tits.”
Felicia flinched in embarrassment and then said quietly, “Thank you.”
Finally, it was Emily’s turn to show her videos. At first, it was the video of Marks’s cock slowly inching inside of her, and then the video of him furiously fucking the young pledge. Each time the girls watched, they looked up at Mark in a way he’d never experienced before. He wondered if it was the look women gave male strippers.
But it was the last video that caused the biggest stir. There were shrieks of surprise, “Oh my God he’s cumming in your mouth Emily!” then laughter as Emily coughed and sputtered. “How did it taste?” one girl asked.
“Well you can imagine,” Emily replied.
“OMG Girl, it’s running all down your face. Damn, he told you to swallow and you did!” said Felicia.
Jessica laughed and gave a thumbs up. “That was a fucking LOAD Mark.”
It was a weird but highly arousing feeling watching them react that way, but the best reaction of all came from Molly. When the phone was finally handed to her her eyes widened like saucers.
Ohhh my GAWDDDD. Oh my GAWWWD… that’s you?” she asked Mark as if there was any doubt.
Mark nodded and watched as she glanced from his face to the video and back again as if memorizing both. Her jaw was practically on her chest. “Oh my GAWWWD you actually came in her mouth and made her swallow it!!!!” It was like she couldn’t believe anyone had ever done that.
The comment made Mark reflect how dirty what he’d just done actually was. He started feeling hard again.
As the giggling and astonishment continued, he looked out the window and noticed a line of vans slowly snaking their way into the park. It was the rest of the sorority and now was his time to bid a hasty retreat. He quickly said goodbye, got back in his car, and high-tailed it out of the lot before the others officially arrived.
He thought of the girl’s parents and what they would think of him if they knew who he was and that he was involved in any way. After all, it was a small world and he had no idea who they were. Thankfully, his face wasn’t visible in any of the videos. He’d also been careful not to give Emily his phone number.
Once he got home he erased his dating profile, safe in the realization that no one could now trace him to the obscene event he’d just been a part of.
The next day at his office his phone rang.
“Ummm hello Mr.Lorimar?” said the voice. “This is Molly Rumsfeld, you know from yesterday in the van?”
His blood ran cold. He remembered the way she had stared at him while watching that last video. “Yes Molly,” he said trying to keep his composure. “How did you know my last name and where to reach me?”
“Oh, I met you before sir, a couple of years ago. You hosted the bring your kids to work day at your firm. I loved your presentation. You were so nice and handsome too so I remembered you. My mom worked with you before we moved.”
Mom? Mark’s mind raced. Rumsfeld. Yes, that face! It was Lillian’s daughter. Efficient, conservative Lillian. His heart pounded. What was this about?
“The reason I’m calling you Mr. Lorimar… well my assignment yesterday was kind of a disaster and they didn’t accept it. But Jessica’s my best friend and she said she’d give me a second chance. I don’t really know anyone else I can call and I had a kind of a crush on you back then. I know I can beat out Emily, I’m still a virgin so I have a very tight pussy, and I’m sure I can swallow all of your cum without flinching or coughing. Can you meet me at the same park this afternoon? Please? I need your help?”
(c) 2022 by R. Jay Moran sexystoriesforwomen.com
For more information on this series check out the essay Using Each Other.