Two Sugars

She walked over normally, not prancing or pushing anything out. When she got to the lounger she wasn't sure what to do though. Her eyes looked back at Syd. She'd worked her mouth more than halfway down Charles's cock now and used her hand to cover the rest while she pushed her head down on it. She hadn't sped up either; she was arousing him, not getting him off.

She glanced back at Charles and saw his eyes riveted on her backside. She couldn't help smiling, and she turned a little to give him a better view. He obviously wanted to touch it, and she moved closer and nodded to him. She felt his slightly calloused fingers gently stroke the curve of one cheek.

"I've been told I have a pretty good ass," she said teasingly.

"You were lied to," Charles said, "you have an exquisite ass."

He fully groped one cheek and let out a moan. Izzie wanted to think it was from her and not Syd's blowjob but she couldn't be sure. Her gaze went back to her roommate. Her breasts were mesmerizing as they flattened and swung with her bobbing as they hit his thighs. Then Charles stuck his other hand out to her. Syd's mouth popped off his cock and she grabbed the bottle. Izzie thought it might have been sunscreen until the clear liquid came out of the top and pooled in her hand. She handed it back to him and then stood.

She walked around and stood over his chest, bending down to grip his cock again and spread the lube all over it. She was close enough Izzie could see the wetness flowing from her open pussy and smell the arousal that had long since overtaken the scent of chlorine. She watched Charles drizzle lube on her ass and Syd flinched as it touched and then flowed down between her cheeks. Then Charles's hand came up. He slid it along her pussy, past her taint, then paused at the jewel. He hooked a finger under the jewel and tugged.

It slid out a little and then something spread her asshole. He pulled for a bit and then let it go. He did it again and got a moan out of Syd. Then again, and he pulled it farther before letting it go, getting more of a moan from her roommate. Then he looked at Izzie.

Izzie paused, wondering exactly how far she wanted to go. His hand was still on her ass, but she'd had guys touch her at the beach while she wore a bikini. She was naked, but she felt kind of hot that this rich guy was turned on by her even though he had her model-quality roommate. But playing with Syd's ass? Was that a step too far?

Charles didn't wait for her long. She imagined after Syd's attention he was very worked up. He hooked two fingers around the jewel and slowly pulled it out. Syd's asshole looked angry and red at being stretched so wide before it shrank down as the teardrop-shaped bulb came out. Charles didn't waste time and shoved a glistening finger in the closing hole. Syd moaned out a gain and Izzie saw her breasts heaving from her heavy breaths. He moved his hand from Izzie's ass and brought it up to Syd's pussy.

As first one, then two fingers plunged into her ass, his other hand rubbed between her lips, clearly finding her clit and giving it as much attention as he could.

"Ohhhh yes, yes, yes, please!" Syd panted. Izzie saw her legs shaking and realized she was rapidly on her way to an orgasm. She'd stopped massaging Charles's cock and braced herself on his thigh. Then one arm started flailing behind her. Izzie reached out instinctively and caught it. She felt Syd's muscles tense and tremble through her strong grip, then Syd let out a wail and bucked. Charles caught her ass and Izzie held her hand as she came.

Syd was still panting as she turned around and shifted her stance. She looked all ready to ride him in cowgirl, but Izzie knew it wasn't going to be the usual way. Charles had one hand on his cock and the other back on Izzie's ass, a sensation she liked more and more. Syd lowered herself slowly, her hands spreading her ass cheeks. Izzie expected there to be a pause at contact, but apparently Syd was very experienced. She watched Charles's cock hit the lubed hole and it spread open for him.

Syd let out a long, low groan as his tool spread her backdoor open. There was a little twitch as his head passed her ring, but otherwise she didn't stop until he was halfway in. Izzie gaped at it, and at the smile on Syd's face. She loved this, apparently. After a moment's pause, she rocked up and down on him, working him in deeper and deeper until what seemed like only seconds later, she slammed home and her ass rested on his hips. Syd looked at both of them with a naughty grin.

"You feel so good in my ass," she purred to Charles.

"And your ass feels divine," he replied.

Syd wriggled a bit on his cock without moving up, then she looked at Izzie, "This feels so amazing."

"You...look hot," Izzie said. It was the first thing that came to mind, but she wasn't lying. The sight turned her on. She could feel wetness on her upper thighs, and she didn't think it was from the pool water anymore. She'd been fighting to keep from groping or fingering herself during the whole display.

"Do you know how he started me out?" Syd asked. Izzie shook her head and Syd said, "Rimming. You ever had someone lick your ass?"

"No," Izzie said. She felt like she should have been more revolted by the idea, but after watching Syd's reactions to everything Charles did to her ass, she was less sure.

"Do it. Charles? Do you want to eat my roommate's luscious ass?" Syd asked.

"Syd-"

"Isabella's rear is amazing to look at. I can only imagine its flavor," Charles said. His voice now sounded as deep and smooth as the liquor he drank.

"Syd I don't-"

"I can see how wet you are," Syd told her as she started shifting on Charles's cock, "You want to play with yourself. You want an orgasm. Let him help. Let...us help."

She felt Charles's hand pushing, and she didn't fight him. He moved her over, and she stepped over the chair. It was narrower than she thought. Syd was right in front of her, looking up with a smile and hunger in her eyes, when she didn't close them from some particularly nice sensation from Charles's cock.

Izzie felt his hands on both her cheeks now, and then cold air as he pulled them apart. She felt like she should stop him, or stop all of this, but Syd was right; she was worked up and horny. She wanted to cum.

The first touch of Charles's tongue was a shock. She'd never felt a tongue on her asshole before. It felt strange, but the poking and licking around her hole got better. His tongue slipped down to her taint and even the bottom of her pussy as well. Nerves she didn't know she had lit up at his touch. She arched her back more to stick her ass out at him.

Soon his tongue wasn't just licking; it poked. It pressed between her cheeks and worked her hole open. At first she clenched against it, but that felt even better. Then he caught her unprepared and went in farther. The shock of the penetration shot through her and sent tingles to her clit. She moaned out in spite of herself.

"Yeah, that's it," Syd said, "Let it happen. Charles knows exactly what to do with a girl's ass."

Izzie began to agree. She clenched only a little now, and more to get the sensations against her ring than to force him out. Soon his tongue had free access to her asshole, pushing in and out, imitating what his cock was doing to Syd.

Syd bounced more and Izzie saw that Charles was thrusting actively now. Syd groaned and her face looked heavenly. Then Izzie had to close her eyes and groan herself as Charles's fingers went to work on her pussy. One slid into her sex while the other slipped up and over her clit. He matched his rhythm to his tongue action.

Izzie panted from the attention and went to grab her breast, but her hand hit hair. Then she felt a mouth on her nipple. She looked down and saw Syd leaned forward, sucking on her tit. She could also see down Syd's back as Charles's balls slapped against her roommate's ass. Syd moaned into Izzie's tit and the vibrations only enhanced the feelings.

Izzie knew she was close and wanted to warn someone about it, but she was too overwhelmed. Then Charles added a flick to one of his finger passes and it was all over. Izzie shrieked and her legs shook like an earthquake. She felt hands on her ass and shoulders as Charles and Syd kept her from falling. They pushed her gently to the side and she settled on the ground on all fours as the pulses and throbs from her orgasm overtook her.

Then she looked up as she heard a loud grunt and moan. Without her as a distraction, Charles got to the business of thoroughly fucking Syd's ass. His hips were a blur and her tits flew wildly as he slammed into her.

"Yes, yes, fuck my ass, fill me up with your cum. Yes! Yes!"

The last "yes" was high and Syd thought she came again as her head shook back and forth and she braced herself on his shoulders. Charles didn't slow, but he only thrust a little while longer before he let out a loud grunt and abruptly stopped. They both stayed still for a bit, breathing heavy and looking at nothing.

Syd recovered first. She leaned forward and whispered something to Charles that Izzie couldn't make out. They went back and forth for a little bit and Izzie was about to let the sounds of their voices lull her to sleep when Syd put a hand on her arm.

"Come on," she said, "I'll take you to the shower."

The shower was huge, with multiple showerheads. Both of them used it together and never had to touch each other, nor trade off to get water. Izzie was thankful for that; she still wasn't sure what to make of what had happened outside.

"It was just sex, Izzie," Syd said after a while, "I'm not gonna ask you out on a date or expect you to call me."

Izzie looked at Syd confused until her roommate broke down laughing. Somehow that was enough to break the tension and they both finished their shower giggling, even spending a little time splashing each other.

-=-=-=-=-=-

Izzie woke up the next morning with the sun shining through the window. She'd slept in one of Charles's many guest rooms. Thankfully no one had asked her to share his bed. She still wasn't sure what she would have said.

Almost as soon as she woke, there was a light knock on her door. Syd came in wearing a light pink bathrobe. Her shapely legs stuck out from under it, and Izzie strongly suspected it was the only thing she wore. Of course, Izzie herself was naked in the bed. She pulled the sheets up for modesty as Syd sat on the edge.

"Charles says breakfast will be ready soon. He's taking me to a show. I'd invite you too but it was sold out a long time ago and we only have two seats."

"That's okay," Izzie said, "I should get back. I...this was nice, but it was a lot."

"Well, I'm gonna give you more," Syd said.

Izzie tensed, but nodded.

"Charles is paying me two thousand a month right now," she said. Izzie felt a bit of a shock at that, though she wasn't sure what shocked her exactly.

"He wants to offer you the same thing," Syd continued.

"For...what?" Izzie asked.

"You'd have to discuss the details with him. And I mean that; do not agree to anything without talking to him, in a neutral site, for real. I like him, but this is still business."

"Syd..."

"Oh come on," Syd said, "I saw that orgasm. You like this as much as I do."

"Yeah, it was wild and fun but...I mean doing what you do? And besides I don't want to screw you out of your hustle here," Izzie said.

"Well...that's the other part," Syd said, looking a bit nervous herself now.

"What is?" Izzie asked.

Syd sucked in a breath, then said, "He'll add another thousand each if we agree to do more stuff like last night."

"You mean...you me and him? Together?" Izzie said.

"Yeah," Syd answered.

"And us...?"

"He said whatever we're comfortable with. Or not. He says he's paying for the threesome. Why, am I so ugly you wouldn't fuck me for a thousand a month?"

Izzie felt a little annoyed. "Fine," she said. She grabbed her phone and flipped the sheets off, then spread her legs at Syd, "Say the word and I'll venmo you a grand to eat me out. Right now."

Syd paled and looked away. "You're right, I'm sorry it's...Yeah, okay, I'm not a lesbian either. I don't even know if I'm bi at all.

"You sucked my tits, remember?" Izzie said.

"Yeah, yeah, fair, okay, I was out of line" Syd admitted as she stood, "I shouldn't be pressuring you. And we both know I'm a little obsessed with the money. Like I said, just think about it. If you want to be with Charles too it won't impact me. We can...talk about the other thing. Don't make the decision today. Breakfast in 15 or so. Don't worry about showering; I didn't either."

"Syd," Izzie said before her roommate disappeared.

"Yeah?"

"It...it felt nice. I didn't mind. But it's..."

"A lot, I know. If it helps, it took me the whole winter break to figure out if I was going to say yes to Charles. I'm glad I did."

Syd left. Izzie sat on the bed, her phone in her hand. Without thinking, she brought up her bank app. The transaction history only showed her balance up above $500 near her birthday and at the beginning of semesters when the cash for books from her student loans came through. Charles would give her four times that every month. More, if she agreed to the threesome plan. Would they be able to do platonic threesomes? Would she and Syd keep their hands off each other? And then there was anal. Could she handle that? Did she want to?

Izzie sat thinking for a long, long time.