Two Sugars: Triple Shot

Thank you to everyone who's been rating and commenting on these stories. I appreciate all the feedback.

I didn't number these chapters and I'm hoping they'll list in order on the site, but in case you're coming to this one first, this is the third in a continuing series that started with my story "Two Sugars" and continues in "Two Sugars: The Second Cup." I tried to add some clarifying bits to the story here, but it will probably help understanding if you read the first two parts.

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Four weeks passed and they were some of the best Isabella could remember. Her new gig as a sugar baby to the man Charles had worked out better than she hoped, especially because it started with her odd curiosity about her roommate Sydney's same arrangement. After tagging along during a visit and sort of stumbling into a threesome with Syd and Charles, he'd offered her the same gig. She hesitated on it for a long time before giving in when Charles assured her he wasn't after sex as his main objective. Then his genuine interest and concern for her had broken through and she opened herself up to the possibility. She had to adjust her expectations when Charles revealed his own hang-ups, namely he only engaged in anal sex with women. But after pushing past that, she enjoyed herself quite a bit.

She felt a little guilty about it, then wondered why. She spent some time in self-reflection, unpacking a lot of assumptions she had about sex work. Because even Charles admitted that's what it was; sex wasn't guaranteed, and some sugar daddies legitimately didn't want it, but the assumption of a lot of people going into it was that sex was included unless one party or the other opted out. Syd still didn't agree with that take, and they'd had a big debate about it during one of their double dates.

Charles kept surprising her too. His interest in her life and his attention to her needs never waned, and he really didn't focus on having sex with her. After the first time it was two weeks before it happened again with them. Then two weeks ago she and Syd had a lot of work to finish on a lab; despite her being in the nursing program and Syd majoring in business, they were both in the same Biology class (her because she'd put it off and Syd because she needed a science credit). Charles had offered his house and Bartolo's cooking instead of their usual double-date. He also helped them hook up a laptop to his screen in the game room. Organizing their notes had been a lot easier with fifteen square feet of screen space to work with, and Bartolo's food was delicious as usual. The idea that he'd give up his date to help them with school amazed Izzie, and she mentioned it to Syd as they finished up that evening.

"Makes me want to reward him," Syd said with a teasing smile.

The smile didn't quite reach her eyes though. Her eyes were pleading.

When Charles invited her to be another one of his sugar babies, he'd also added the stipulation that he'd give each girl an extra thousand dollars if they'd be willing to do threesomes with him. He didn't expect the girls to fully lez out (Izzie's phrasing; she literally couldn't imagine those words coming out of Charles with his old fashioned and precise phrasing like an old-school radio announcer). A little contact between them, some breast fondling, or maybe a kiss would be enough to excite him, and then he'd probably take one of their asses while the other girl took care of herself.

Izzie wasn't sure about it. Syd, on the other hand, definitely was. It had annoyed Izzie at first because she thought Syd was a bit of a hypocrite; she spent all this time talking up how she wasn't with Charles for the money and she legitimately cared about him, but she was pestering Izzie about the threesome because it meant an extra grand a month. She never called Syd out on that, though, because she'd become less sure about Syd's motivation.

"You want to rock, paper, scissors for it?" Izzie had joked. She saw the intensity drop from her roommate's expression, but the playfulness remained. Syd was the one who ended up finding Charles in his house while Izzie wrapped up their work and shut everything down. She also teased them a bit when both of them were red-faced and embarrassed as they left the house that night.

That wasn't the only time she'd gotten a look like that from Syd though.

With the secret no longer between them, they'd made a bit of a game out of their date nights. They'd chat about outfits, debate styles based on where Charles was taking them, and of course discuss how slutty their look should be. Izzie had five new outfits from labels like Dolce, Prada, and Saint Laurent now. Charles spoiled them but he wasn't careless; the pieces he'd gotten Izzie mostly went with each other, so she could mix and match the clothes to create a few different looks.

She also now owned three garter belts with thigh-highs and bras to match.

The fun sleepover/pre-date vibe sometimes got interrupted, though. A few times Izzie had gotten to their dorm and found Syd topless in her garters and a thong, holding up clothes for her to debate. She'd hold them to the side so her round C-cup breasts were fully visible. Then Izzie would make a choice and she'd turn around and bend at the waist, showing off her wide ass that wasn't at all covered by the thong.

Then whenever Syd helped her with her clothing, Izzie sometimes noticed Syd's hands lingering on her skin, or Syd pressing up against her when she didn't really need to. And Syd brought up the threesome discussion at least once a week, always with the excuse that she "just wanted to make sure you haven't changed your mind."

Tuesday that week was rough for Izzie. She'd messed up in one of her nursing classes and one of the other students had gone off on her, telling her if she made the same mistake in real life she could kill someone and said she should be tossed out of the program. The professor had put the student in her place, but it rattled Izzie. Oddly, she wished she could talk to Charles about it, but Tuesday was Syd's night.

She got back to the dorm and Syd stood next to her bed naked. She had her towel up rubbing her hair, her arms' position lifting her breasts up and thrusting them out. She faced the door, too, so the smooth shaven mound of her pussy was fully visible.

"Fuck, Syd, put something on, will you?" Izzie said, looking away.

"Isn't that what you're here to help me with?" Syd replied.

"Yeah but do you have to flash all your goods at me?" Izzie said.

"I'm sorry if it bothers you," Syd said, "I just thought...I mean you've seen me-"

"Yes, Syd, okay, we both fucked Charles. We were together. I saw you naked, you saw me. You bring up that fucking thousand dollar bonus every fucking week, I can't really forget any of that, can I?" Izzie snapped.

Izzie had spat most of that without looking at her roommate. When she finally turned after sitting on her bed, Syd was in her corner of the room, frantically pulling things out of her dresser. She'd moved her towel so it fully covered her. After a few minutes Syd turned back and almost ran to their door, grabbing her purse and only quickly glancing at Izzie on her way by.

"Syd, I'm sorry, wait-" Izzie tried to say but she was cut off by their door slamming. She guessed Syd changed in the bathroom and then left for her date. She was asleep before Syd returned that night.

When she woke the next morning, Syd was sitting in her bed, looking across at Izzie. Her face looked pained.

"I'm sorry I yelled, Syd," Izzie said immediately, sitting up in her own bed.

Syd didn't do anything for a few minutes, then she took a deep breath.

"I, um, talked to Charles. He helped me through some stuff. I kind of ruined dinner, honestly. Make sure you two have fun tonight, okay?" she said.

"Yeah, okay," Izzie replied.

Syd hadn't looked at Izzie while she talked, but then she met Izzie's eyes. Izzie was a little shocked by the intensity of her look.

"I...need to explain," she said.

"Look, you don't owe me anything, I was out of line-"

"No," Syd cut her off, "I want to clear this up."

"Okay," Izzie said after a moment.

"I'm not trying to get the extra thousand dollars. Charles...he told me last night that if I really needed or wanted it, he'd give it to me. That sort of...woke me up," Syd said.

"About what?" Izzie asked, now feeling very nervous.

"I really liked being with you and Charles. I...I really want to do it again. And a big part of that is you. I liked watching you. I liked...I like touching you. I think you're really pretty."

There was a long stretch of silence after Syd stopped talking.

"Syd...are you telling me you're into me?" Izzie asked.

"I don't know how to explain it," Syd said, looking away and seeming frustrated.

"Well...I mean if you're in love with me-"

"No, see, that's what's so...fucked up about this," Syd said.

"Syd, you aren't making sense here," Izzie said.

Syd blew out a frustrated breath and buried her face in her hands. Izzie felt a pang of sympathy for her roommate. She got up and moved over to Syd's bed. She climbed on and sat next to her, hugging her around the shoulders.

"Syd, just tell me. No judgement, no drama, I promise."

Syd looked up and took another deep breath.

"I liked the threesome. I haven't been able to get it out of my head. I keep thinking about what I could have done...what we could have done. I know I mentioned the thousand dollars a lot because...I mean, how am I supposed to say 'hey, so you wanna fuck? But not as lovers?' At the same time I feel like I got a free sample of a really good meal and I want to order the whole thing."

"So...You want to fuck me, but you don't want me as your girlfriend or anything?" Izzie asked after a moment.

"I told you it was fucked up," Syd said.

"A little bit, yeah," Izzie said, but her own mind was in turmoil.

Could she really hold it against her roommate when Izzie's own mind had been bothering her the same way? She'd had sex with Charles six times total. It was almost a given when she slept over with him on Fridays now. They'd also surprised each other a week ago by suddenly feeling really horny after their meal date and just going at it in a dark corner of a park. After the park incident she'd had a near panic attack afterward wondering if anyone saw her or the area was clean, then laughing about her paranoia when Charles calmed her down. But after every other tryst she'd had a thought or even a sort of vision like her first time with him. She'd imagine Syd sitting there naked, or she'd replay their encounter but add Syd in as a third player. Usually Syd was an added piece of scenery; laying across from her in bed while she was taken, or her body wrapped around Charles from behind as he thrust into Izzie's ass. One night earlier in the week Izzie had been taking care of herself, and the mental image she had was Syd hovering over her, getting her ass plowed by Charles as Izzie pleasured herself beneath them.

She suddenly looked over as if she forgot where she was. Syd was still in bed, hugging her knees refusing to look at Izzie. Izzie realized she was being a bitch.

"I...may have had some thoughts about you too," Izzie admitted.

Syd looked up at her hopefully.

"I don't think they're the same," Izzie said, "but after I'm with Charles, sometimes...I wonder what it would be like with you there."

Syd's expression lessened but didn't leave. She started running her hand down Izzie's leg, from her knee to her ankle over her pajama bottoms. It was casual and comfortable but given their discussion Izzie wondered if there was subtext.

After a while of sitting together in silence, letting their words hang there, Syd said, "So..."

"I'm not there yet, Syd. I don't know if I'll ever be ready to make it more than an idle fantasy. Especially because if we go there, Charles would sort of expect it."

"I don't think Charles is like that," Syd insisted, "If we're uncomfortable-"

"Syd, it's business. If Charles pays us the extra thousand dollars, he's paying for both of us together, with him, having sex. Maybe we don't go down on each other but we couldn't ignore each other either. I don't think he'd appreciate 'oh that was just a one-time thing' from us. And I'm sorry but right now, in my head, doing it for the money is the only way I can see myself agreeing. I just...I can't handle any other justification for it. I'm sorry."

"Well...like I said, it's not all about the money for me," Syd replied, sounding a little sad.

"I know. Again, I'm sorry I threw that in your face. It was bitchy and mean."

"Doesn't really solve our problem though, does it?" Syd pointed out.

"Right?" Izzie agreed.

-=-=-=-=-=-

The next week in the dorm there was tension. It wasn't the sexual tension of wondering how and if you would get together. Neither was it the eggshell tension of two people on the verge of tearing into each other in anger. It was more like when a sibling has a lover the other doesn't approve of. They were fine to talk to each other and hang out, but any time either of them had a date with Charles it got awkward.

The playful dress-up sessions were gone. Now when one of them got dressed, the other sat on their bed studiously ignoring them, or they left the room altogether. Their double date was a near disaster; they spent nearly half of it awkwardly avoiding looking at each other, until Charles offered to end it early and they both realized they needed to step up their game. Izzie couldn't help feeling like that was another incident where sugar babying was more like sex work. She didn't really want to sit and have dinner with Charles and Syd, but that's what Charles was paying for. She only hoped she'd been a good enough actress.

Friday night she overdid it. Later on she realized she was trying to make up for the double-date. She wore a short dress she used to go clubbing in her freshman year and didn't bother with undergarments. She sat in Charles's lap for dinner and let the hem of her dress ride up so her bare ass was on his legs. When it was clear she would be feeding him the marinated beef roast and vegetables by hand, he gave up reaching around her and simply rested his hands, one on her thigh, the other on her ass. By halfway through the meal his hand had slid up her legs to her pussy. Every time she fed him a morsel, he fed Izzie her own juice on his finger.

Bartolo was a devious genius as well. He'd noticed what was going on and for dessert he brought out what he called a "keto chocolate mousse" portioned out on twelve individual spoons. Izzie fed Charles the first two. But then Charles pulled her dress down, exposing her hardened nipples. He looked at them expectantly. Izzie got the hint and smeared a spoonful of the dessert on her nipples and breasts, both licked and sucked clean by Charles right after.

Then Charles took charge. He pushed her up and bent her over the table. He quickly but gently removed the butt plug in Izzie's rear. Then he moved and she felt coolness on her asshole. First it was creamy, then she felt the hard coolness of metal. He deposited two spoonfuls there, then his mouth and tongue went to work. He licked vigorously, finding every scrap of dessert on her rear, then pressing his tongue into her asshole in case he missed some. He searched deep with his tongue for that.

Izzie squirmed and moaned through the experience. She was well used to taking pleasure from her ass by then, and the way he'd bent her over put the rounded edge of the table on her pubic bone, letting her grind her clit against it.

She moaned loudly when he stood and pressed his cock against her ass. She reached back and felt the slick, wet residue of the dessert on her backside as she pulled her cheeks apart for him, bearing down to let him in. He hilted in her ass and she grunted, her eyes stinging; the plug and the rimjob, along with some leftover mousse, had lubed her up a bit, probably some of his precum too, but he still more or less went in dry. The burning pain and stinging tingles slowly morphed over into pleasure, especially as his thrusts forced her into the table and on the edge where her clit ground into it.

She'd worked him up into a frenzy, it seemed; he used quick, hard thrusts into her ass, gripping her hips with his fingers hard enough for her to feel his trimmed nails digging in. The shudders and slaps added to the grinding on her clit and the friction of her nipples on the tablecloth. She groaned out and encouraged him to fuck her hard.

Charles thrust even harder and she cried out in shock at the brutal pounding until she suddenly felt him shudder and almost collapse on top of her. His cock pulsed in her ass, filling her up with his cum. The feeling washed over her and she might have had a small orgasm, but it wasn't a full climax like she usually got. She still felt accomplished at getting him to be that frantic, though.

"You need to go wash up," he said.

"I can help you finish dessert," she replied.

"No, I mean...you should wash yourself out. Some of that mousse probably got inside you. You don't want an infection or anything."

Izzie felt a flush of warmth that Charles was that considerate. She pulled herself together as well as she could and headed off for the bathroom.

They watched another old movie in the game room afterward, her in a nightie and panties at his request. She was snuggled up to him but there was no play between them; the hand that was draped over her most of the film didn't even make a move for her breast, though it was practically right under the palm.

"Isabella?" he said as the movie finished, "Is there a problem with me seeing both of you at once?"

Izzie tensed. Charles noticed immediately.

"Izzie, I'm not trying to blame you. I want to understand what's happening. I do like both of you. Obviously there's friction now. If seeing both of you at once is causing that, I want to do what I can to fix it."

Izzie shrank away a bit, not wanting to meet Charles's gaze.

Charles sighed. "Izzie...I'm not going to do anything right away, but last night was awkward. And today you aren't you. I really liked what you did at dinner; it was very erotic. But I could tell you were overcompensating. I told you before; I didn't want this arrangement so I could have sex with you. Now if it's very personal and you two are going to work it out on your own that's fine, but to be blunt, I'm not getting what I paid for if this keeps up."

"It's the threesome," Izzie blurted out, as if some traitorous part of her brain bypassed her major thinking and took over her mouth. She tried to move past it but Charles was relentless, forcing her to deny different conclusions he made until she broke down and explained the whole discussion she'd had with Syd. Afterward, he sat and thought for a while.

"So you don't want to have a threesome with her?" Charles asked.

"I...I don't know. No? But I've had these thoughts..."

"Are you someone who has one-night stands?" Charles asked.

"I mean...I have but usually because I found a hot guy at a party. I've never gone out to a club or a bar and come home with a guy I just met."

"Well, not that I don't appreciate you being selective about your partners, but it would have made this easier," Charles mused.

"How?"

"You could go out and sleep with someone you'd want to be with just based on your own preference, without our whole arrangement in the mix. Then you could figure out if you still would want Syd involved," Charles said.

"I'm pretty sure I wouldn't, but...I mean I'm doing all this anyway, and I didn't hate the threesome a few months ago..."

She felt Charles straighten up, and when she looked he had a slight smile on. "I have a proposition for you," he said.