An adult stories – Two Sugars by Chris6160,Chris6160 As readers of my other stories know, I usually do a good amount of character build-up before getting to the action. This story is no exception.
I always appreciate comments and feedback, so please leave some if you’re so inclined.
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“Come on, Syd; we share everything. You can’t keep all the tea to yourself on this one!” Isabella pleaded.
“It’s kind of what I’m paid for, Izzie,” Syd said while scrolling through her phone on her bed in their shared dorm, “I had to sign a little piece of paper and everything. Actually, it was a huge piece of paper, with a lawyer’s name at the top.”
Izzie rolled her eyes. “Oh come on Syd, you know that just means you can’t go to TMZ or hop on TikTok and spill. It’s just me, Isabella Rocha, best damn roommate anyone could hope for and hot piece of ass.”
“Modest too,” Syd quipped.
“Bet your ass,” Izzie replied, “Come on, when have I screwed you over?”
“Well you were supposed to deliver on that bottle of Fireball for the Halloween party-”
“I told you, my brother got a flat. Totally not on me!” Izzie insisted.
“Then you forgot to leave your keys for me when you went home for Thanksgiving and I had that job interview,” Syd said.
“Did I not hook you up with Damian Morgan? Did he not fuck you into next week? Because I’ve got complaints from the rooms next door and a really vivid memory of you waddling out of the bathroom bow-legged that afternoon.”
“I was not bow-legged,” Syd insisted.
“You were squirming like something itched your pussy good, and it was attached to the star running back. Who I hooked you up with right before homecoming?” Izzie said.
“Fine, whatever,” Syd relented, “but this is different. This isn’t college co-ed shit. This is like, legit legal real-life stuff. I do not want to fuck this up.”
“Fine, whatever,” Izzie echoed in a slightly bitchy tone and went back to her tablet, trying to read the virtual textbook for her chem class.
She’d been deathly curious about Syd’s side hustle for the past month. At the beginning of sophomore year, both of them had their hearts set on rushing a sorority on campus that had promptly evaporated under hazing and sexual harassment scandals the school couldn’t ignore. Izzie had been a bit disappointed but Syd had been devastated, almost to the point of tears. When she asked, Syd explained the sorority had a strong financial network and got students favorable rates for student loans and grants, and the member dues were way less than housing and book costs.
Izzie had never thought about that, but Sydney was always focused on money. It had actually annoyed Izzie when they were first assigned as roommates freshman year; here was this white girl with an hourglass figure, shiny brunette hair, straight white teeth and a pair of lawyers for parents and she was panicking about money? Meanwhile Izzie was the third child of her single mom, and only made it into college thanks to a few financial aid packages and a damn fine essay. She’s resigned herself to the idea that the rest of her life was going to be working her ass off as a nurse and never paying off her student loans until some boyfriend knocked her up and left her in the lurch like her mom. It was family tradition, almost, and this college gig was just her last vacation before she’d have to own up to it. She wanted to live it up in the last four years of fun she figured she’d have, and this bitch was cramping her style.
After a blowup fueled by too much alcohol, bad timing, and boy troubles, Izzie got the real tea on her roommate. Her parents were both lawyers, but her younger brother was the darling, so most of Syd’s mother’s attention and money went to him. Meanwhile her father was better at office politics than legal arguments, and he’d picked the wrong side in a dustup at his firm. His train on the partner track had been derailed and her mother had started questioning why, if she was the one making all the money, she was putting up with him at all, especially with all the rumors about how he chose his personal assistants. By the semester break that year, Syd was trying to figure out how to schedule Christmas at two separate houses.
Izzie tried to convert Syd to her “four-year last hurrah” outlook but she’d only been partially successful. She thought she’d made a breakthrough when Syd agreed to rush the sorority with her, and only found out about the financial motivations after it fell apart. Syd had been frantically job hunting all throughout their first semester but never landed anything solid. The whole time her stress level had been going through the roof.
Then she came back after winter break completely different. The first couple weeks she’d seemed a little nervous, but then she relaxed more. She also disappeared on weekends and at least two nights a week, only telling Izzie she had to work.
Izzie sort of stumbled onto the truth by accident. She’d snagged herself a boyfriend after homecoming and they’d kept it going pretty strong. Izzie caught some feelings even, so she went nuclear when, three weeks after coming home from break, she found out he’d reconnected with a high school flame over break and had been stringing Izzie along.
Izzie’s frustrations had been both emotional and physical and a week after the breakup she’d broken her “substitute boyfriend” by forgetting to seal the battery properly and using it in the shower. Syd had found Izzie digging through her drawers wrapped in a towel.
“What are you doing?” she’d asked.
“Looking for your fucking vibrator,” Izzie had snapped back.
“What the fuck Izzie?”
“It’s not like you’re using it. You’re getting good dick on the regular now. Yeah, I know. I don’t know who he is but I’ve never seen a woman look as well fucked as you when you come back from-oh holy shit!”
Somehow before that moment Izzie had never connected Syd’s satisfied, well-fucked look with the times she “left for work.” Suddenly really embarrassed, Izzie had immediately rushed back to the shower. Two days of awkward exchanges followed. Finally Izzie decided it had to stop and had told Syd that she didn’t judge and was supportive, but if she was escorting she should be careful, because her mother had told her a lot of stories.
Then Syd had told her the real story.
“It’s called sugar-babying,” she’d said, “It’s just one guy. I go on a few dates with him a week. Then one overnight over the weekend. Just him and me. No clients, no pimp, nothing like that.”
“But-”
“Izzie I’m not really supposed to talk about details. But I’m okay,” Syd had insisted.
Over the next couple of weeks Izzie realized Syd was more than okay. She was more relaxed than Izzie could remember ever seeing her, and she thought only part of that was from the regular sex she must be getting. She also acquired some new things Izzie couldn’t help but notice, like a brand new Apple watch and some blouses with brands like French Connection and Reiss. Also, the couple of times she’d caught Syd changing before or after work, her underwear was always colorful, lacy, and often included a garter belt.
She’d switched from worrying about her roommate to teasing her quite a bit about her excursions, frequently greeting her on her returns from trips by inquiring about what positions they’d tried, or if she had to fake it that night.
Tonight, she’d tried a different approach to sate her curiosity, promising no more teasing and an honest, non-judgemental approach if Syd would just let clue her into some details.
“If you’re so curious you could always try it yourself, you know,” Syd finally said after silence reigned in the dorm for a few minutes.
“Yeah, okay,” Izzie scoffed.
“What?” Syd asked.
“Look at you, Syd, then look at me,” Izzie said.
“You look fine,” Syd insisted.
“Sure,” Izzie scoffed again, “My frizzy-haired, snaggle-toothed face and flat chest are what all the guys want to pay top dollar for.”
Syd rolled her eyes. “For fuck’s sake Izzie you wear a b-cup. That’s not nothing. And you’re the only one that thinks your tooth is even noticeable. People only see it because you point it out. You’ve got a natural all-over tan by default, your eyes may as well be hypnotic with that golden brown mix you’ve got, and people would literally worship your ass if you let them. Trust me, you look fine. Weren’t you the one calling yourself a hot piece of ass a second ago?”
Izzie actually felt herself blush at her roommate’s praise. She’d never heard Syd say any of those things before, and especially not with the voice and look Syd gave her. There was a bit of an awkward pause again when Izzie thought Syd would look away, but her face was almost pleading, as if she was desperate for Izzie to believe her.
“Well still,” Izzie finally said to break the tension, “I don’t think it would happen. And after what that asshole did, I don’t think I could stand the idea of being a side piece.”
Syd rolled her eyes that time, and Izzie felt a little hurt. Having successfully killed the conversation, both of them went back to their own thing.
When Izzie got up to get ready for bed, Syd said, “I’m not, you know.”
“What?” Izzie asked.
“I’m not a side piece,” Syd said quietly, “I couldn’t do that either.”
Izzie’s eyes went wide and she made to ask more questions but Syd shook her head and said, “Shit, I shouldn’t have said that. Look, it’s really not what you’re thinking, Izzie. Just…leave it at that.”
Izzie didn’t know what to do with that, so she just walked to the bathroom.
-=-=-=-=-=-
Despite the awkwardness of their conversation that night, or maybe because of it, Izzie couldn’t get the reality of Syd’s job out of her head. Every day she would wake up or start drifting off to sleep and think of things she wanted to ask Syd about her experiences.
At first she just blurted out the questions, but usually Syd brushed her off the same way, or suggested she just look online somewhere where people who were curious asked. But Izzie wasn’t interested in that. She didn’t want to know what some random stranger’s experiences were; she wanted to know what Syd, specifically, was doing.
Izzie wasn’t dense, and she could tell she was annoying Syd after a few days, so she kept her questions to herself. When Syd left that Saturday morning, Izzie found herself saying, “I hope you have a good time.”
Syd turned around and smiled at her. “I will,” she said.
Izzie couldn’t explain why she was suddenly obsessed with Syd’s job. She wondered if it was some sort of weird rebound thing. It had certainly taken her mind off of her ex, though it didn’t do anything for the other kind of frustration.
Her replacement vibrator had finally come in, and she decided to put it to use right then. As the contoured plastic split her folds and wet her sex, she found her mind conjuring images of Syd in lingerie, with a man standing behind her, clearly pounding away. That image stuck in her head as she pushed herself to an oddly intense and satisfying orgasm.
She wasn’t sure what to make of her fantasizing. She wasn’t secretly in love with Syd, she was pretty sure. You weren’t fantasizing about fucking her, she thought to herself, you were fantasizing about her fucking another guy. Her other guy.
As she always did, Izzie didn’t dwell on the problem; she just pushed it to the back of her mind and ignored it, burying herself in studying, random videos, and hanging out with other friends. By the time Syd got back from “work”, Izzie had almost forgotten about it.
Of course, then Izzie came back to their dorm Tuesday after her afternoon class and saw Syd bent over her drawers in a black lace corset and garter, stockings not on yet, the little string of her thong barely hiding anything. She looked away quickly. And averted her gaze until Syd had her little black dress on for her date. Then Izzie delayed going to the campus dining hall in favor of a session in her bed with the vibrator. Again, her mind was full of Syd, but still in lingerie and fucking her mystery lover. Izzie wondered if she was a voyeur now, but she didn’t feel any particular compulsion to try following Syd, or even to try catching someone else having sex. The next night she could clearly hear Pat in the room next door getting some, but she just had a fleeting thought that she was happy for them and went back to what she was doing.
She vowed to herself she wasn’t going to jill off again on Thursday, Syd’s other “work night,” but her method of distracting herself was to look more into the whole sugar baby thing. Unfortunately after the first one or two entries she found everything else seemed to be stories about a “friend of a friend I heard of,” and most of them had posted anonymously. Izzie got it, for sure; she could only imagine the kinds of DMs those women would get telling the internet they’re basically a high-end prostitute. And even if that wasn’t totally correct based on the descriptions, most people on the internet wouldn’t bother making that kind of distinction.
Syd was late coming back that night. Izzie had planned on waiting up for her, but at some point her body got the better of her and she dropped off. She was a little surprised to find herself nicely tucked in the next morning.
Then Syd asked her if she was around for dinner Friday night. Izzie made a sarcastic quip about her dating life but Syd ignored it and said, “Good. We need to talk about something,” before rushing off to her morning class.
Unfortunately, Izzy couldn’t push that worry to the back of her mind like everything else; she was sure it was some sort of “roommate breakup” situation. Maybe she had found a co-op or something and was moving into an apartment next year? Was she moving in with her sugar daddy full time now? Or maybe she’d just gotten tired of the awkwardness that seemed to be growing and wanted to get another roommate. Then she wondered if Izzie was going to ask her to move into an apartment. She checked her finances and for the first time in a while really looked at the long term picture. She had $250 to her name, which was more than she usually had if she was honest with herself; breaking up with her boyfriend had done wonders for her savings. But she was pulling in maybe $60 a week from her on-campus job, and she had no prospects. There was no way she’d be able to afford anything other than the dorms going forward; her student loans didn’t cover off-campus apartments.
Because of her worrying, Izzie was a bit down when she met Syd for dinner, to the point where Syd opened the conversation with, “What’s wrong?”
“Just…are you sticking around the rest of the semester?” Izzie asked.
“What?” Syd asked.
“I mean…you’re moving out, right? That’s what you wanted to talk about? That we won’t be roommates anymore?” Izzie said.
“Oh God Izzie that’s not it at all. Sit down, have some food,” Syd insisted.
Izzie was a bit relieved, though she still had a bit of worry because now she wasn’t sure at all what Syd wanted to discuss. After getting her food and eating for a bit, chatting about nothing with Syd, she finally got down to it.
“So, look, I know you’re still kind of obsessed with this sugar baby thing, and I’ve been shutting you down,” Syd said. Her voice was clear but quiet, but Izzie still cast a paranoid glance around the dining hall to make sure there weren’t people listening.
“Syd, it’s fine, I’m okay with it. I shouldn’t have pushed and I’m sorry,” Izzie said, “And I’m only a bit curious you know, I’m not, like, obsessed or anything.”
Syd smirked. “I saw your tablet last night. You’d been scrolling around about it for a couple hours at least,” she said teasingly.
Izzie blushed. “Well it’s sort of like your secret life. I guess I’m a little curious,” she admitted.
“How curious?” Syd asked.
“Why?” Izzie replied.
Syd took a deep breath and paused for a second, then said, “I talked to Charles.”
“He’s your…?” Izzie left the question unfinished but Syd nodded.
“If you want, you can come with me this Saturday. There’s no expectation,” she quickly added as she saw Izzie’s eyes widen and mouth open to say something, “Charles says it would just be me inviting a friend over for part of the day. This is still my job, though, Izzie and at some point, well…I have to do my job.”
“So, um, is he gonna ring a bell or something and that’s when I go?” Izzie asked.
Syd looked at her annoyed until Izzie giggled, which set Syd off. “I don’t know,” Syd finally admitted, “he said if you showed up he’d play it by ear.”
Izzie felt a little thrill, but then she paused and looked at Syd accusingly. “What exactly did you tell him about me?” she asked.
Syd shrugged. “I just told him you’d been curious about what I do,” she insisted. After Izzie glared at her for a bit, she admitted, “I may have…talked you up a bit to him.”
“So, you’re pimping me out?”
“No!” Syd insisted, “Izzie, seriously, I did not tell him you were going to do anything. You can wear a burqa when we go if you don’t want him looking or whatever; I swear we’ll all be perfectly fine. But you can’t fool me; you want to know what my job’s like. He’s kind of curious to meet my roommate, and he says he feels guilty taking me away from my busy college life, and he feels like this is letting me keep some of it.”
“And what are you getting out of this?” Izzie asked.
Syd shrugged. “I mean, he’s not totally wrong; I wouldn’t mind having you around rather than puttering around in his house by myself.”
There was a long silence after that as they both finished their meals. Finally Syd looked at her phone and said, “I have to get to study group. Look, think about it. If you want to go, just tell me tomorrow morning. And I promise, there’s no strings attached here.”
-=-=-=-=-=-
Syd usually left around 10:00 on Saturdays. Izzie rarely slept past that, especially since she broke up with her boyfriend, and this Saturday was no different; her eyes popped open at around 8:50.
She stayed perfectly still, just watching as Syd got out of bed and headed off to the bathroom. She saw the few glances Syd cast her way, her expression questioning (possibly longing). Izzie went back and forth in her head a bunch of times while her roommate primped and prepared to leave. She wasn’t dressing up like her weeknight trips, she came back from the shower in a purple tanga and bra combination with lace edges, and then slipped on tight yoga pants that showed off her legs and ass.
By 9:45 Syd was mostly put together, just touching up her eyeliner. Izzie still hadn’t moved from the bed. Syd looked at her for a long moment through the mirror.
“Fine, fuck it,” Izzie said suddenly.
She threw off her covers and dashed into the bathroom, taking a lukewarm shower at best. She’d lost the time to do anything effective with her hair before even getting up, so she just pulled it back into a ponytail that at least wouldn’t leave her head looking like a mop after a lightning strike.
She got back to the room and froze with indecision. She looked at her closet and bureau while standing, clutching a towel. Syd came up to her.
“I don’t know what to wear,” Izzie admitted.
“Wear what you want.”
“Shouldn’t I wear what he would want?” Izzie asked.
“It’s not your job. You’re the guest. You’re just my roommate, come for a hang out,” Izzie reminded her, “Besides, if he wants me to wear something he has to buy it for me.”
They both giggled at that. Izzie put on some black slacks that she knew showed off her ass well and a basic tank shirt with built-in support so she didn’t have to bother with a bra. It was only after walking down the hallway with Syd she realized the shirt was one she bought for dates with her ex.
The car waiting to pick them up was no basic Uber. It was sleek and black and she could use the chrome on it do to her makeup. She literally slid across the leather seats when she got in and had a full window and climate control console in the back. The car set off as soon as Syd was settled.
The ride was about 45 minutes, moving away from the college and the city surrounding it into more of a suburban area, though one with a lot of trees and wide lawns that almost made it look rural. They pulled up to a house that seemed a bit out of place with the environment. From her perspective Izzie thought the house was shaped like an “L” and looked like it was up on stilts to keep the main building off the ground. Most of the walls were white, and what wasn’t white was glass or steel. The bottom floor seemed to be all glass, in fact; she could see inside to a small living room type setup with a couple of futons and lounge chairs that looked like they could be pulled out next to the in-ground pool settled in the corner made by the house. The car pulled into a driveway that ran on the opposite side, ending in a garage that was connected to the house, but not the glass part of the bottom floor.
Syd got out and Izzie followed her after a moment. Syd thanked the driver and then Izzie stopped in a bit of panic when the car pulled away. Syd came over to her.
“It’s okay. We’re not stuck here. You can leave any time,” she said.
“No, no, I’m fine,” Izzie said, forcibly calming herself again.
Syd walked over to a set of double doors in the glass and punched in a code on the keypad. A loud “thunk” sounded and then she pulled the door open for Izzie to enter. Then she followed Syd to one of the staircases leading up.
Inside the white, glass, and metal theme continued, though wood was added to the mix with some of the furniture, and black for some of the appliances and the kitchen countertops.
“Charles?” Syd called out.
“Ahh welcome my beautiful Sydney.”
Izzie turned toward the voice. It was deep and almost overdone, like an old radio announcer, and Izzie found it oddly attractive. The owner of the voice was a tall man in slacks and a button-down shirt with a light sweater over it. It should have looked like the outfit of an old grandpa, but the man wearing them only had lines on his face, not wrinkles, a full head of hair (though it was greying), and he walked confidently upright, not hunched over or hesitant. Despite that he had kind eyes and a warm smile, something the lines suggested was common for him.
Syd stepped forward with a smile and he grasped her hands, pulling her close and planting a kiss on her cheek. Then he turned to Izzie.
“And you must be Izzie. Am I right in guessing that’s short for Isabella?” he asked.
“Yes,” Izzie said with a blush. The way he’d said it he put a slight roll on the ‘l’s at the end of her name, but not the same way her abuela did with her accent. The way he said it got a definite reaction out of her.
“Would you be upset if I called you that instead?” he asked, “I find the quick nicknames everyone prefers to be harsh. I like to take my time, especially when it’s more pleasant to do so, and ‘Isabella’ sounds so much better to me.”
“That’s…fine,” Izzie said, thinking that it sounded more than okay to her too. She glanced at Syd (or should she say Sydney?) and her roommate had a slightly smug expression on.
“Would like a quick tour of the house?” he asked.
“That would be great,” Izzie agreed.
He took her around the main floor. It was mostly open plan, with no distinction between the kitchen, living room, or dining room except for the furniture present on the floors. A few walls provided some barriers, but there were no real doors or anything blocking off most of the rooms. Then a hallway led to a bathroom she thought was bigger than their dorm, as well as a library and a home office of sorts. She paused in the library at a framed, painted picture of a young man hung on the wall. He looked about her age, and the resemblance to Charles was unmistakable.
“Your son?” Izzie asked.
“Yes, only child of my first wife. Just about the only good thing to come out of that marriage,” Charles said.
“First wife?” Izzie asked.
“Izzie,” Syd said warningly.
“It’s fine, Sydney my dear,” Charles said, “Yes, my first wife was with me for ten years. Young Lucas showed up after the first year. I admit I may have been working too hard in those days, but I wanted to make sure they wanted for nothing. Maybe it would have worked out if we’d talked, but she wanted to sleep with her personal trainer instead. And then the foreman of the construction crew putting an addition on the old house.”
Izzie winced and glanced over to see an “I told you so” look on Syd’s face she wasn’t sure was warranted.
“I tried again after Lucas turned fifteen. He’d come under my custody by then as his mother wasn’t able to hold a job very well and had taken to bouncing from boyfriend to boyfriend, some of them rather sketchy. He was actually the one that said I should try again. Of course he’d just got his first girlfriend and couldn’t understand why I wouldn’t be chasing after girls when I could afford to do things like take them out on dates, with my own car, and even have privacy to do dirty things to them.”
Izzie couldn’t help but giggle as Charles told the last parts in a mock whisper imitating the attitude of sex-curious and naïve boys.
“Priscilla was definitely a bit of a wildcat in bed. By then I was successful, and she certainly didn’t mind the toys I came with.”
Izzie couldn’t help raising her eyebrows and giving Charles a teasing look. She was astonished when he noticed and actually blushed.
“Not…um…not what I was talking about,” he stammered, “I meant the nice cars and dinners and…well anyway, she got me hooked and had me buying her a ring in only 9 months. Lucas, of course, had been dumped by his first girlfriend by then and was dead set against it, convinced the entire gender was nothing but conniving backstabbers out to make men miserable.”
There was a significant pause then and in a low voice Charles said, “Maybe I should have listened to him.”
“Her too?” Izzie asked.
Charles shrugged. “The first problem was that she wasn’t particularly kind to Lucas after we married. They’d been cordial before, but as soon as the reception was over, it seemed, she turned on him. Still, I stuck it out for three years. Then she got pregnant. I’d told her I wouldn’t mind another child; I was in my late thirties then. I helped her through it just like I had for Lucas’s mom, and was there for the delivery. The only other time I can remember hearing a whole medical staff go quiet at once was when a patient unexpectantly died.”
“You lost the baby?” Izzie asked.
“The baby was half black. Priscilla’s family is from Poland, Sweden, and Germany,” Charles explained, “That was literally the last time I saw her. She had her lawyer handle the divorce through trading papers. It was only after it was done that Lucas confessed to me part of the reason they fought so much is because Priscilla had called him during her bachelorette party and asked him to come pick her up, then spent the ride home trying to get into his pants and go to a hotel room.”
“I’m…I’m sorry,” Izzie said after a while, not really sure what to say.
Charles shrugged. “It happens. But perhaps you can see why I opted for the arrangement I have with my dear Sydney here.”
At that he moved over and slid a hand around Syd, who leaned into him, then jumped a bit as he clearly goosed her ass. She playfully slapped his shoulder, then accepted a kiss from him. This one was a little more intense than his greeting had been, but not a blatant makeout session either. Izzie found herself mesmerized by the display anyway, especially as Charles’s hand never left Syd’s ass, and actually began kneading it a little as the kiss lingered.
He pulled away though and walked back over to Izzie. For a weird moment Izzie thought he was about to try kissing her, too, but he merely said, “I did want to discuss expectations here. As you know there is a business element to my relationship with Sydney, though I don’t like to focus on that if I can help it. My point is, you can hang around as long as you like, but I am going to want her to myself at times. Honestly I don’t mind you hanging around, but if you interfere or start trying to actively undermine me I will ask you to leave.”
His voice and tone were still pleasant, but Izzie could tell from his expression he was dead serious.
“I..I think I’m okay. If you tell me to go off somewhere I get it,” Izzie said, “I’ll probably head back in an hour anyway.”
“You can, but I would love for you to stay for dinner,” Charles said, “Bartolo is a wonderful cook and I so rarely get to share his creations with anyone else. And, if I may be blunt, you would be improving my view of anything going on.”
He let that comment linger and after giving Syd another quick kiss he disappeared into his office.
“Come on; I’ll show you the game room,” Syd said.
-=-=-=-=-=-
The game room was stuck in one of the corners where it could overlook the pool. It also had a small deck outside with a stairway down there. Izzie was a little freaked out at first because the last two feet of the floor on the pool side were transparent so it was easier to see. Syd assured her it wouldn’t crack.
The game room itself would have qualified for a man cave except for it being on the second floor with all the windows. It had a flatscreen that looked taller than she was and definitely wider. The largest sectional sofa she’d ever seen formed a “C” around it, and she saw various game consoles and their controllers tucked on a shelf beneath it. On the next wall over there was a full bar with shelves of drinks on par with any restaurant’s layout. In the middle of the room was a pool table, a generic round table with 8 chairs, and one of those stand-up shuffleboard tables.
“I think Charles said there are tops somewhere you can put on the pool table and turn it into a ping-pong table, but I’ve never seen that,” Syd said, “You want a drink?”
“Um,” Izzie paused but Syd rolled her eyes.
“Charles doesn’t care. And no, this is not me pregaming so I can face what happens later. I genuinely like Charles. When we go on dates I’m usually sober. I mean, I have to be; I can’t order wine at a restaurant, can I?”
“Even if you’re there with him?” Izzie challenged as she accepted the wine Syd poured.
“He’s well off but he’s not, like, ‘fuck you’ rich. He has to make reservations and wait for tables just like most people. Except the restaurants we go to aren’t where most people go,” Syd admitted, “Come on, let’s shoot some pool.
Neither girl was a shark, but both of them knew the rules for 8-ball and had at least played a few times. Very few. The girls ended up giggling over the easy shots they missed and celebrating every sunk ball like the winning shot in a tournament.
At one point Charles came in and poured himself a drink, then paused to watch them. Syd took her time with her next shot and sunk it, and then lined up another one, always facing away from Charles. She also wiggled and posed herself a bit when she bent to shoot. After Charles left, Izzie raised an eyebrow at her. Syd shrugged.
“Charles is a bit of an ass man,” she said.
The girls put away three hours or so in the room between the tables and the gaming systems, then Charles invited them to eat. Bartolo looked Latino and conversed with Charles in Spanish. The food was some sort of casserole, Izzie thought, but it tasted divine. It stayed together on her fork but seemed to melt in her mouth and the flavors were amazing. She complimented him probably too much when he appeared. She was a little disappointed about the lack of dessert, but then she saw a glance between Syd and Charles and realized dessert was probably something very different.
They’d had another glass of wine with dinner, but the mood shift sobered her up. When Charles walked away, Syd came over to her.
“Time for me to leave?” she asked.
“Well…you don’t have to, but if you stay you’re going to see some things. Charles is still pretty active. Half the time when we’re together we aren’t in bed.”
Izzie stood thinking and was ready to ask for an Uber when Syd added, “I’d like it if you stayed.”
“Why?” Izzie asked bluntly. She almost took it back but Syd was already answering.
“Because I like hanging out with you. And Charles and I both think you’re hot.”
Izzie’s mouth dropped open and Syd blushed.
“Shit, I may have had too much wine. Look, I told you before, you’re pretty. I’m not coming on to you. But having you around would be a thrill for Charles, and I want you to really understand what’s happening here, and that I’m not…you know…forcing myself to do anything. I’m not making any fucking sense but would you stay? Please?”
“Sure,” Izzie said. She didn’t think she’d be able to unpack all that without a lot more time, but her hesitancy about staying got muted in the face of Syd’s pleading.
Syd came forward and hugged her hard. “Thank you so much, I know it’ll be fun,” she said. She pulled back and then looked at Izzie with a suddenly mischievous smile.
“You want to go for a swim?”
“I didn’t bring a suit,” Izzie reminded her.
“Neither did I,” Syd replied.
Izzie felt her heart leap into her throat. She felt scared and excited at the same time.
“He-”
“Charles will be around,” Syd said.
It was a warning and a dare. Izzie blew out a breath.
“Fuck it,” she said and ran for the game room with a nervous giggle.
Izzie stripped off her clothes as fast as she could and jumped in the water. She got a bit of a shock but it was more from the wetness than the cold; the pool must have been heated. She heard another splash and saw Syd surfacing behind her with a wide grin.
Izzie hadn’t been skinny dipping since she was a kid and being naked was only bad because her mom told her it was. Whether it was the taboo nature of what was going on, the wine, or both, the whole experience was very sensual. The water passing over areas she usually kept covered stimulated her in ways she didn’t expect. She wasn’t going to get off swimming naked, but the water seemed to provide a never-ending caress of her sensitive bits.
As they dove and frolicked in the water, Izzie found herself swimming behind Syd and she had to stop. Syd was as naked as she, but there was an unmistakable flash of something not skin-colored as Izzie looked. They surfaced and Izzie said, “Syd, something you want to tell me?”
“What?” Syd asked innocently. Izzie just fixed her with a pointed stare until she saw her roommate blush a bit, then shrug with a smile.
“So when you said he was an ass man…?” Izzie prompted.
Sydney just shrugged and winked, still smiling.
It was another sobering moment for Izzie, but it didn’t stop her enjoying the water.
As promised, Charles did join them, though he didn’t get in the water. He came out of the house with a glass in his hand, amber liquor filling the bottom quarter, and a deep maroon robe with silk, or at least silk-like, trimming on the edges. He sat in one of the lounge chairs near the inner corner of the pool and simply watched the girls swim and frolic. Izzie worried at first about how much Charles could see, but soon she stopped thinking about it.
She was a little surprised when she felt Syd’s arms around her and the press of the girl’s breasts against her back. They’d mostly avoided touching each other for their swim. Combined with the water’s effect on her, the touch was oddly stimulating.
“I’m getting out of the water for a little bit,” she whispered in Izzie’s ear, “you can keep swimming. But you might think about coming out too.”
Izzie barely moved when Syd swam away. Her eyes locked on her roommate as she swam to the stairs near Charles. She rose from the water slowly, water sluicing off her curves. She walked up the stairs like a Bond girl emerging from the water, except no Bond movie had ever dared show as much skin as Syd was. Nor would they have showed the little blue jewel visible between Syd’s ass cheeks
She glanced over at Charles and saw a slight smile on his face, but it was matched by an eager hunger in his eyes.
Syd slowly sauntered over to him. She gathered her hair up in her hands and wrung it out, as she walked, which had the side effect of lifting and pushing her boobs out, her upward tilting nipples poking out even more. Then she let her hair go and shook her head, spreading the dark tresses out around her.
She got to Charles’s lounger and immediately crawled onto it from the bottom. From Izzie’s perspective, she could see everything; Syd’s ass had spread a bit, exposing the jewel even more, and her pussy lips poked back through her thighs. Syd shaved completely. Charles, meanwhile, watched as she trailed her breasts on his legs, her heart-shaped ass poking in the air over her head.
Charles pulled his robe open, exposing his nude body and his hardening cock. Izzie drifted over to the side of the pool for a better look. Charles was in decent shape for his age. A little paunch around his stomach and no cut muscles, but she saw hints of muscles on his arms and legs. His chest and stomach were covered with silver hair as were his legs. Syd settled herself on top of him, trapping his cock against his stomach as she flattened her body against him and kissed him.
His hands cupped her ass immediately as they devoured each other’s mouths. Izzie saw his hands dig into the soft flesh and squeeze her cheeks together, the jewel between them dancing around. Syd wriggled her body on top of him and Izzie could only imagine how it felt with her rubbing her breasts against his hairy chest.
Soon enough their makeout session ended and Syd slid back down his body. Izzie couldn’t take her eyes off her roommate’s sex, now swollen with arousal and seeming wetter than when she’d gotten out of the pool. She was sure it had been grinding against Charles’s cock and she wondered if some of the moisture down there was his precum. She stopped with her thighs on his knees and shifted back and forth a bit. Izzie could see her breasts sitting near his hips and she bet his shaft was nestled between her C-cups. He groaned at the sensation and she saw his hips twitch a bit.
A tit fuck wasn’t the order of the day, however. Syd slid down farther until his cock popped up in front of her. It didn’t seem massive from Izzie’s perspective, but it was big enough to get the job done, she guessed. Syd licked up the underside while cradling it in her hand. Her other hand disappeared between his legs and Izzie wondered if she was fondling his balls. Or maybe even playing with his ass the way he clearly intended to play with hers.
After several licks and some kisses to the head, Syd’s mouth opened and she inhaled him. At first her mouth only covered the head and stopped just below the edge, but then she bobbed up and down, sliding slightly farther each time.
Izzie noticed her arm getting tired. That was when she realized she was holding herself up by one arm, and the other had drifted between her legs. She pulled it away, ashamed, but then she wondered why. She was watching live, in-person porn. Was this all that different from when she masturbated to the thought of Syd getting fucked the other day.
You know it is, some part of her mind prodded. She was forced to agree. Syd had been in lingerie in her dream; she didn’t have a full view of her dripping, bald pussy or her large, swinging breasts.
She got another shock when she saw Charles looking at her. His eyes were half open, obviously enjoying Syd’s attention. He didn’t seem angry; she wasn’t quite sure what his look was.
“Do you want a closer look?” he asked.
Izzie paused. Obviously his question wasn’t just for her benefit. He’d get an up-close look at her naked body while getting a blowjob.
Would it really matter, though?
She pushed herself up, not bothering with the stairs. Her smaller breasts got framed between her arms as she brought a knee up and hauled herself out of the pool, spreading her legs nice and wide for balance and probably giving Charles a clear view of her pussy. She hadn’t shaved in a while so her bush was definitely covering some things, but she hadn’t been letting it run wild for years either.
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.