Rylie’s Proposal

"I just wanna get fucked!" Erica blurted.

Riley choked and struggled not to spit out her drink.

"No, not just fucked, I wanna get used!" Her roommate gesticulated drunkenly, spilling her drink on the kitchen floor. "I want a guy to look at me like all he can think about is bending me over, and, and, like, pulling my hair, and screwing the shit out of me! You know what I mean?"

"Yeah," Rylie laughed. "I know what you mean."

She had come home to find Erica in tears on the couch. She'd been laid off, and had no idea how she was going to find the money for tuition and rent. Rylie got them some drinks, and did her best to reassure her that things would work out somehow. She'd only intended to help her relax a bit, but had apparently overdone it and landed in drunken confession territory.

Rylie liked Erica. She was a good roommate. Easy to get along with. Always paid her bills on time, and did her share of the chores.

However, if pushed, Rylie might have admitted that she thought Erica was just a bit uptight. She dressed conservatively. She didn't smoke weed. She preferred studying to partying. She'd never once brought home a random guy from the club. Or from anywhere, for that matter.

Which made her aggressive pantomiming and declaration that she wanted someone to "fuck every hole until she couldn't walk straight" a bit shocking.

"Erica, I've never seen this side of you," Rylie chuckled.

"Oh, my older brothers are fuck-ups, so I've always been under all this pressure to be the perfect good girl and graduate and do a good job and not ruin my life by getting pregnant or doing drugs or ever having any fun ever." The words gushed out of her like a burst dam.

"You know, I think you might need some food," Rylie said, putting a pot on the stove to make some noodles.

"No, what I need is to get wrecked by a big fucking cock." She heaved a sigh and drained what was left of her drink.

Rylie nodded understandingly, and replaced her glass with water.

"I'm so jealous of you, Ry. You do what you want, how you want. And who you want! I always meant to ask you to help me with guys, but there were finals and work and stuff. And now I'm gonna have to go back home and live with my mom and get some shitty retail job, and, and, and..." She trailed off, sniffling and blinking away tears.

"Hey now, no more of that," Rylie said, giving her a quick hug while fetching sauce from the fridge. "No one's moving home. I told you, we'll figure something out. Then we'll go dancing, and I'd love to be your wingwoman."

"There's nothing to figure out, it's too much money," she gestured dismissively. "Just promise me you'll get me laid before I leave. Like, proper laid."

Rylie bit her lip as she stirred the sauce into the noodles. She wasn't sure if what she was about to say was a good idea or not. Despite Erica's proclamations, it might be a bridge too far for her.

"Erica, you're not a virgin, are you?"

"No! I've done it before. It's just, you know, been a while. And the guys I have been with? They were sweet and caring and, um..."

"Kinda boring?"

"Yes!"

"Okay." She took a deep breath. "What if I could solve both of your problems at the same time?"

"What are you talking about?"

"You remember my friend Max?"

"The fuckboy?" Erica responded, then clapped her hand over her mouth, horrified at what she'd said.

"It's alright," Rylie laughed, "he is a fuckboy. Total trust fund kid with no idea how the real world works, and an overinflated ego."

"So why do you hang out with him?"

"He's fun." Rylie shrugged, dividing the noodles into two bowls. "He likes to party, and loves being the center of attention. We get into the cool clubs, go to wild places, and meet outrageous people."

Erica took the offered bowl and started eating. Rylie sat down across from her.

"And, there is one other reason." She hesitated long enough for Erica to look up from her noodles. "Sometimes... he pays me."

"Why does he..." Erica frowned, then opened her eyes wide in realization.

"It's not what you think," Rylie blurted. "He just pays me to act like his girlfriend."

"Do you have sex with him?"

"No! Well, kinda?" Rylie blushed. "I only go down on him." Confessing this to Erica was more awkward than she'd expected. "I told him if he wanted to pay to fuck someone, he could go find a proper escort."

Erica raised an eyebrow.

"Look, the point is, Max has more money than sense. Early on, he made it clear he likes spending time with me, and would be willing to pay me enough to make up for any work I'd miss if he wants to go party for a weekend or whatever. And then some. We have fun together, and I make some extra cash at the same time."

"And the sex?" To Rylie's relief, Erica sounded more curious than horrified.

"When we get back to wherever we're staying, he likes to watch me masturbate."

"Then you give him head?"

"Yeah. I don't mind after I'm turned on."

"Huh." Rylie considered this for a moment. "Wait, you said you had a way to solve my problems, then you brought up Max?"

"I know, I know, just hear me out! You want to get properly fucked, right? Well, for all his flaws, Max actually has a pretty nice cock. He's clean, he's always respected my boundaries, and I know he's interested in you."

"He is?" Erica seemed more shocked by this revelation than anything else.

"Oh yeah. He's told me before that you could join us anytime. I assumed you wouldn't be interested in that kind of thing."

"Um, how much money are we talking about?"

"Enough to cover your tuition and a few months of rent."

"Holy shit, really?"

"Really," Rylie nodded. "What do you think?"

"Fuck it." Erica grinned. "Two birds with one stone. And I won't have to move home with Mom! Call Max, tell him I'm in."

A Few Days Later

"Where is he?" Erica asked again, pacing back and forth. "I thought you said he'd be here at lunch? It's almost three!"

"He said, 'around lunch,'" Rylie answered from the couch. "Max has never been on time to anything in his life."

When Rylie had called Max and explained the situation, he'd enthusiastically agreed, and said he'd pick them up on Friday. Now it was Friday, and Erica was a ball of nerves.

"Are you sure this isn't too short on me?" She fretted, tugging at the hem of the skirt she'd borrowed.

"It's not, but even if it was, the whole point is to get you 'properly fucked,' remember?"

Erica grimaced, hearing her own words quoted back to her. Rylie stood up and squeezed her shoulders.

"E, are you sure you're still into this? It's not too late for me to call Max and tell him to fuck off."

"No, no, I mean, it's fine, I just hate waiting."

As if on cue, there was a knock at the door. Rylie gave Erica a quick hug, and let Max in.

"Ladies! Sorry I'm late, I had lunch with some cryptocurrency guys, and they would not stop talking. You know how it is. How ya doing, Rylie?" He gave them both a quick hug, then dropped onto the couch, exhaling noisily. "Whew! Alright, Erica, come here, sit with me. Let's chat."

She glanced at Rylie, who nodded, then sat down next to Max. Rylie leaned against the wall, curious to see how Max would handle this.

"I was fucking stoked when Rylie told me what you're looking for. You couldn't have known it, but your timing was perfect. I've been sitting on something kinda special, waiting for the right opportunity, and babe, I think it's for you. Here's the deal. I've got this pill I ordered from a Russian catalog. A buddy tried it, said it's like hurricane-force Viagra. This little beauty is supposed to let me fuck like a goddamn stallion all day and night."

Erica blushed, but didn't stop him.

"Now, you know that Rylie and I have an arrangement. We usually just do a bit of partying, a bit of dancing, then she gives me head. We keep it kinda softcore. Girlfriend experience, you know? I throw her a bit of walking-around money because I was tired of her saying she couldn't go out because she had to work. So now she can have a good time with me, no worries. And that's great, I love it, but like you, I am craving that next-level experience. I wanna rock it hardcore, have a day that we're both gonna remember when we're old and gray, you feel me?"

She nodded, as if this was a perfectly reasonable thing to say.

"Cool cool cool. Rylie told me you were looking for a good time, but I get that this is probably gonna be outside your comfort zone. Now, I don't want you to think I'm paying you to do anything you don't want to do. I'm gonna push your limits, sure, but what I'm spending my money on is an experience, one that I think we're both gonna savor."

"Plus," Rylie interjected, "I'll be there the whole time to make sure you're okay. If it's too much at any point, you just let me know."

"Right," Max nodded emphatically. "So, here's my dream, and I think this magic pill's gonna make it happen for us. We're gonna go out, we're gonna have a good time. We're gonna dance, we're gonna party, and I'm gonna fuck you every hour on the hour."

"Every hour?" Erica hesitated.

"Every hour," Max nodded, glancing at his watch. "For twelve hours. So what's it gonna be, babe? Are you in or out?"

"Um," She slowly nodded her head. "Yeah. Yeah, I'm in. Let's do it."

"Whoo! That's great fucking news, 'cause I took the pill on the drive over here, that short skirt of yours is driving me crazy, and I'm already hard as a motherfucker!" He looked at his watch, and held up one finger. "Okay, the clock staaarts... now!" A timer chimed, and he quickly unbuttoned his pants to free his cock. True to his word, it looked almost painfully erect.

"Oh!" Erica gasped.

"Come on, babe, we'll start slow. For now, just go down on me." He rubbed her shoulder encouragingly, pulling her closer as his cock twitched.

She glanced at Rylie, clearly a bit hesitant to do it in front of her. Rylie gave her a wink and a thumbs-up.

"Oh yeah," Max groaned, closing his eyes as she lowered her head and wrapped her lips around him. "This pill's got me really goddamn sensitive!"

Rylie bit her lip, fascinated by the sight of her uptight roommate bobbing her head in Max's lap.

"Jesus, your mouth is so hot! It feels amazing!" Erica made a surprised sound as Max put his hand on the back of her neck, encouraging her to go lower. "Keep going! I'm not gonna last long."

Rylie was surprised at how aroused she felt from the sight of Max using Erica's mouth for his pleasure.

"Oh fuck! Fuck yeah," Max grunted as Erica slurped loudly around his cock. "I'm getting close!"

He opened his eyes and looked straight at Rylie as he pushed harder on the back of Erica's head. She didn't protest, just moaned in response and swallowed him deeper.

"Your throat," Max gasped, as Rylie squirmed in sympathy, "so fucking tight!" Erica's lips finally reached the base of his cock, making him groan loudly. "Fuck! I'm gonna cum!"

Erica gripped the edge of the couch cushion tightly as Max started shaking. He grunted with each spasm, still holding her head down as he shot his load into her throat. She moaned, eyes watering, trying to swallow everything.

At last, he gasped and let go, collapsing back and panting. Erica popped up immediately, coughing and choking, wiping his cum from her lips. She looked at Rylie with surprise.

"You okay?" Rylie mouthed.

Erica nodded, tears running down her cheek, but grinning widely.

"Holy shit," Max crowed as he buttoned up his pants. "This is gonna be sick! Okay, ladies, we got a flight to catch. Tonight, I'm taking you to my buddy's club in LA. Grab your stuff, real quick-like. Rylie, bring that little red number I bought you last month? Erica, we got just enough time to go buy you something sexy to wear."

"Seriously?" Rylie asked. "You've got twelve hours, and you want to spend a bunch of them on a plane?"

"It'll all balance out with the time zone change," Max shrugged, unconcerned. "Hustle up!"

4 P.M.

An hour later, Rylie was sitting with Max on the bench outside a changing room. Erica was inside trying on a handful of dresses. The saleswoman had been a bit rude until Max had flashed his credit card. Suddenly, she'd been more than willing to help Erica, who seemed a bit overwhelmed by the fancy shop, pick out a few things.

"How's this one? Is it too much?" Erica pulled back the curtain a bit timidly. She'd had to remove her bra, and the loose purple fabric plunged daringly from her shoulders, exposing quite a bit of pale skin.

"Whoo!" Rylie grinned. "Your tits look great. Can you dance in it?"

Erica hesitated, then lifted her arms to sway to an imaginary beat. The dress barely clung to her curves, and started to shift away from her breasts. She squealed and pulled it back into place.

"It's good." Max nodded appreciatively. "Do you like this one or the green one better?"

"Um," she considered, "I think the green one would be better for dancing?"

"Done deal." He nodded, glancing at his watch. "But, uh, don't take that one off just yet." He stood up and put an arm around her waist, pulling her into the changing room. As the timer beeped again, he winked at Rylie and closed the curtain.

Erica squealed in mock protest. The saleswoman looked up at the noise and narrowed her eyes when she noticed Max was missing. Rylie shrugged in a "what are you gonna do" kind of way. The saleswoman sighed and busied herself with neatening the already well-organized displays.

Rylie grinned and turned her attention to the curtain. It wasn't quite closed all the way, and from where she sat, she could see a narrow view of Erica and Max's reflections in the mirror. Erica had dropped to her knees, allowing the dress to fall down her arms, exposing her breasts, which she was pushing together around Max's cock. He was whispering something while thrusting urgently into her cleavage.

She looked flushed, with a mixture of arousal and concern on her face, no doubt worried they'd get caught. Max clearly didn't care about anything except the way her tits felt around his shaft.

Rylie crossed her legs, once again surprised at how erotic she found the sight of them together.

Erica was awkwardly leaning forward, trying to lick the tip of his cock at the peak of each thrust. Max grimaced as her tongue teased him and said something Rylie couldn't hear. Erica looked up at him, eyes wide, as he shoved her back against the wall and fucked against her chest harder.

Abruptly, he stiffened, and Erica let out a surprised sound as thick white cum splattered her chest. It shot across her collarbone and fell across her breasts. She eagerly leaned down to wrap her lips around him, sucking and swallowing the last of his climax as his spunk dripped down her nipples onto the purple fabric.

He stepped backward, and walked calmly, if a little winded, from the dressing room. The saleswoman frowned and pretended not to notice him buttoning his pants as he approached the counter.

"She'll take the green one," he announced. "And the purple one, too. We, uh, spilled something on it."

5 P.M.

Max drove like a bat out of hell to get them to the private jet terminal at the airport in time for their flight.

"Not like they'd leave without us," Max laughed dismissively, "but I got a schedule to keep."

The plane was small but luxurious. The cabin had just four seats, all facing each other, more than like recliners than airliner seats. The flight attendant got them all seated, and disappeared into a small galley area as the plane took off. After reaching altitude, she reappeared with glasses of champagne.

Rylie sat across from Max and Erica, sipping her drink and curious to see what Max would do at the top of the hour. Erica seemed intrigued as well, but Max just grinned and made small talk until the timer on his watch went off.

"Erica," he grinned, obviously pleased with himself. "Want to join the mile-high club?"

"What, you mean in there?" She shot a hesitant look toward the restroom door.

"No, babe, right here."

"Here?" Erica looked apprehensive. "What if the flight attendant comes back?"

"She won't. Passengers on flights like this value their privacy."

"Um," she hesitated, shooting a nervous glance at Rylie. "Okay. Yeah. Uh, how do you want to..."

"I want you to come ride my cock." Without waiting, he lowered his pants to around his ankles. His cock jutted upward, already hard and eagerly twitching.

"Oh!" Erica grinned and reached under her skirt to slip off her panties, then moved to straddle him in the oversized seat.

Rylie bit her lip as she watched Erica wiggle her hips, imagining the way she was positioning Max at her entrance.

Max grinned as Erica slowly lowered herself, one hand on his shoulder, the other between her legs. Her skirt was draped over them, blocking Rylie's view, but she could tell the moment he filled her from the way Erica shivered.

Slowly, she started moving on top of him, lifting and lowering herself. She gasped every time he slid home. From behind, Rylie couldn't see her expression, but the tilt of her head and the way she squirmed told her everything she needed to know.

After a few minutes of slow, sensual build-up, Max's hands appeared on her waist.

"This is nice and all, but I want you to ride me!"

Erica squealed as he pushed her forcefully down onto him. He squeezed her hips tightly, tugging her up and slamming her down over and over. She cried out every time he thrust upward to meet her.

"Yeah, like that," he groaned, "fuck me hard!"

"Oh my god!" Erica moaned.

Rylie squirmed. The cabin smelled like sex, and hearing the wet sounds of their fucking was almost more erotic than if she could see Max's cock plowing into Erica.

"Fuck!" Max grunted. "Your pussy! Feels so good!"

"Yes!" Erica cried over and over. "Yes, yes, yes..."

"I'm gonna fuck this pussy all night long!"

"Yes, fuck me," she moaned. "Use me! Oh god, use me!"

"I'm cumming!" He groaned, slamming her down one last time and holding her in place with white knuckles.

"Ah!" She grasped the headrest of his seat as he shuddered between her thighs.

After a long minute, he let her go. She quickly got to her feet and ran to the bathroom, hand between her legs.

"Holy shit," he grinned, lazily stroking his cock, which glistened with Erica's juices. "This is fucking incredible. I gotta get more of these pills."

Rylie didn't say anything. Her jeans suddenly seemed very tight.

6 P.M.

A few glasses of champagne later, Erica was laughing as Rylie and Max shared a story about a night clubbing when Max's timer went off again.

Erica set her glass aside and looked expectantly at Max, who was already unbuttoning his pants. As before, his cock sprang forth, erect and ready to go.

Once again, he had Erica sit in his lap and ride him, gripping her hips tightly and fucking her against him until she was moaning with every thrust.

Rylie watched, and hoped it wasn't obvious how turned on she was. She hadn't really considered what effect it would have on her to watch them fuck over and over again.

Erica seemed overwhelmed, wordlessly groaning and gasping as he took full advantage of her body. Rylie hoped the experience was living up to her fantasy.

Max stared lustily at Erica's bouncing tits, not caring at all that Rylie was there. If anything, it seemed to excite him to have an audience.

At last, he came inside her again, cursing triumphantly the entire time. Erica threw her head back and gasped at the sensation, before climbing shakily to her feet and stumbling to the restroom.

This time, Rylie followed her, slipping into the tiny room with her.

Erica looked surprised, but quickly sat on the toilet to wipe up the cum leaking out of her.