Two Sugars: The Second Cup

This is the second story in a series: "Two Sugars" is the first if that hasn't been picked up by the site. I tried to make the story stand on its own a little, so there are some explanatory paragraphs that will be redundant if you read the first story.

I appreciated all the feedback and comments the first installment got. Hopefully this story will be as well received.

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Isabella sat on her bed in just panties and a T-shirt, trying to read a very dense legal document for the first time in her life.

She'd probably seen dozens of documents like this. Maybe hundreds; she didn't know how many apps she had on her phone, but a lot of them had some document like this where she flicked through it until she saw the "I agree" button, if scrolling through was even required.

Both people who knew about this document had told her to actually read it, and the intensity of their warnings had made her follow their advice.

It was the last day of spring break. Last year on this day, she'd already been out of the dorm by noon, cruising around the welcome back barbecues at the Greek houses with more open guest policies, then transitioning to the raging parties as the sun went down. She'd woken up with a hangover and done the walk of shame in someone else's oversized shirt because she couldn't find any of her clothes. The guy had come back to retrieve his shirt the next night and did her a number of sexual favors to get it back.

This time around, it was 4:00pm and she hadn't left the dorm since lunch. Her stomach rumbled loudly to remind her of that fact, but she just sucked down some more water to trick her body into thinking she'd eaten something. Then her body countered by reminding her she'd been pulling that trick for half an hour and now she had to pee.

Izzie groaned and went to the bathroom, her head swimming with "whereby"s, "persuant"s, and "signatory"s. She'd looked through so many "legal jargon for dummies" pages she felt like she should at least have a clue but a lot of things in this document were unique, and most of those sites helped out with more common arrangements.

She hadn't found one that covered sugar baby contracts yet.

There were a lot of sites with contract templates. Unfortunately Charles had gotten his contract custom-made (Izzie really wanted to know what that talk with the lawyer had been like).

She was only looking at it because of what had happened last month. Her roommate, Sydney (Syd between them) had gotten a job at the beginning of the semester. Izzie hadn't known anything about it until she figured out it involved Syd having sex. After her curiosity and pestering got overwhelming, Syd had broken down and let Izzie in on the secret; she was a sugar baby. Her sugar daddy was a man named Charles. Charles was older, maybe late 40s or early 50s, owned a huge modern house with an in-ground pool, bought her expensive clothes, took her to fancy restaurants, had his personal chef make her meals when she was over, and, occasionally, fucked her in the ass. Sometimes he licked her there too.

The way Syd had let Izzie in on the secret was by inviting her over to Charles' place with his permission, which is when she got an up-close and personal experience of what Sydney did with Charles. She'd also given in and gotten her ass rimmed by the man while she was face to face with her naked roommate as she bounced her rear end on Charles's cock.

After all that, Syd told her Charles wanted to offer her a contract like Syd's. It was worth $2,000 a month just to do the same things Syd did. But if she'd agree to be with Syd and him on the weekends, there was an extra grand in it for her.

All of that was in the contract, though any hint that they were having sex was left out. Izzie got that without having to look it up; if he'd said anything like "I will pay this woman two grand to come to my house and let me fuck her ass on the regular" that was prostitution, which meant either the contract wasn't legit or it was illegal for being prostitution.

She got back to the room and had barely settled back onto her bed when the door opened. Izzie smiled as her roommate came in.

Syd had a classically beautiful body; pale skin and brown eyes with C-cup breasts and a wide ass and hips that gave her an hourglass shape. She'd been letting her hair grow, and the black, slightly wavy tresses now reached down to about where her bra strap would be. Izzie knew from the experience at Charles's that her nipples pointed a little upward and were so pale the areolae were almost indistinguishable from her skin, her pussy was shaved bare, and her inner lips poked out between her labia.

Syd paused and Izzie blushed and looked away at her questioning glare. Izzie always felt like her body wasn't as attractive, mostly because her chest was only a 32B and her hair was brown and frizzy enough it looked like you could use it to scrape food off pans. And the 32B was a stretch; there was a lot of air between the tops of her bra cups and her chest. If she went and got herself measured, she'd probably come up an A. She also had a crooked front tooth that bothered her to no end and meant every picture she was in she kept her lips together. Her own bush was controlled, but only enough that it didn't poke through her underwear or swimsuits. Her Latino heritage gave her tanned skin that darkened with the sun, which some people (including Syd) said was an asset. The two features she would allow were good on her were her eyes, which were hazel with almost golden edges and flecks in them, and her ass. She had a heart-shaped backside that you could bounce a quarter off of (something proven by several other co-eds in the past two years).

And now she was figuring out if she wanted to use her moneymaker for...actually making money.

"Hi Syd, welcome back, how was your break?" Syd prompted her.

Izzie blushed as she realized she'd been staring but not actually looking at her roommate. "Sorry," she said and just held up the tablet.

"Is that?..."

"Yeah," Izzie said, "I've been trying to read it like you said. This is not Dr. Seuss, and there isn't a lot of stuff online to help. No way I can afford to have another lawyer look over it, if I could even get up the nerve."

"Look, Izzie, I'm sorry but if one of my parents looked over it there's too much risk they'd find out-"

"Yeah, yeah, I know, you told me over break. How was the trip with your Mom anyway?" I asked.

"Pointless waste of money," Syd griped more viciously than Izzie expected, "She claimed she wanted to spend time with me but she doted on my brother for the whole trip like she always does. He got a sunburn after the first day and you'd thought he developed skin cancer. Mom dropped two hundred dollars on creams and ointments for him, and cancelled our dinner reservation after my brother didn't feel well enough to go. I ended up getting wings at the hotel bar that night. There was a guy there who seemed interested, I thought about bringing him up to our room just so I could tell my mother that I found my own entertainment since she was so busy."

Izzie laughed. "You totally should have," she said.

"How was your break?" Syd asked.

Izzie shrugged, her smile fading. "I just stayed here. Mom told me she and her new boyfriend were going on a road trip the first weekend in his car, which was a two-seater, and then Mom had night shifts the whole week. That would have meant tiptoeing around the house until one in the afternoon every day and then getting told to run errands for my abuela and my aunts."

"I'm sorry," Syd said as she sat on her own bed.

There was semi-awkward silence as Syd unpacked some things from her case and stole glances at Izzie looking at the contract.

"So you think you're going to do it?" Syd finally asked.

"I guess," Izzie said.

"Charles deserves more than 'I guess'," Syd said.

"What, are you sweet on him?" Izzie shot back and then started as Syd blushed. "Syd, seriously?"

Syd shrugged. "He's a nice guy, Izzie. He has that old fashioned charm going on and of course he buys me all these presents and stuff. Frankly the orgasms don't suck either, not gonna lie. And yeah, I kind of care about him. He's like...the ideal version of a sweet uncle with a bit of a dirty side."

"That must be a rich family thing," Izzie said, "None of my uncles are sweet. Most of 'em are loud and fat, and they smell."

"Come on, Izzie, you've never had a fantasy about a nice older guy being all gentle and kind, maybe randomly picking you up for a night on the town that's not parties and clubs, and then later...you thank him for it?" Syd asked.

"It's not really my speed, Syd," Izzie said.

Syd sighed. "Well you might want to think harder about that contract then. He's not paying you to be a hooker, Izzie. He wants company. One of your date nights is alone, right?" she asked.

"Yeah, Wednesday," Izzie said.

"Right, well, he doesn't want you to just hang on his arm and stay silent through dinner until he can get you alone for a quickie. He wants to talk to you, learn about you, maybe help you out with some life stuff. If you just go into it and act all impatient and timid waiting for him to get around to the sex it's not going to work for either of you," Syd insisted.

Izzie sat for a while looking at the contract without reading any of it. "I don't think I can...like...catch feelings for him, Syd."

Syd shrugged again. "So maybe you two are more like friends with benefits. My point is just that the personal connection has to be there. I know you weren't totally turned off by him when you visited, even before things got hot. Focus on that maybe."

Izzie sighed and dug back into the contract.

-=-=-=-=-=-

After spending Sunday getting nowhere with her feelings or her legal interpretation, Izzie did what she usually did with her problems; tried to forget about them and distract herself. Fortunately with more than half of her new classes starting up Monday she had a lot to keep her mind off of it.

That lasted until Tuesday afternoon. Izzie came back from the gym and found Syd standing in their room wearing garters, thigh-highs, and a thong. She saw a black bra strap and when Syd turned to look she saw that the cups of the bra were mostly transparent lace.

They didn't say anything at first; they both knew what and who Syd was dressing up for.

Izzie sat on her bed and played on her phone, but she kept glancing up at Syd as she worked on her makeup.

"He's going to ask, you know," Syd finally said.

"About what?" Izzie said stubbornly.

"What you're going to do," Syd replied.

"Isn't that between me and him?" Izzie said.

"Izzie, if you don't-"

"Yes."

"What?" Syd said, turning to look at her roommate.

"I'm...I'm going to do it. At least I want to meet with him and talk about...about everything. I don't know if I can give him what you do, like the lovey-dovey stuff. And if that's a dealbreaker we need to figure that out," Izzie said.

"That's great," Syd said, "I'm sure he'll like it."

There was another pause while Syd finished her makeup. When she stood to go to her dresser, Izzie said, "Syd, what about us?"

Syd froze. "What do you mean?" she asked.

"The extra thousand. Threesomes," Izzie reminded her.

Syd let out a long sigh without turning around, her hands stuck on the handles of the drawer she was about to pull open. Then she took a breath, turned around, and walked over to Izzie. Izzie watched her approach intently until her roommate stood right next to her bed.

"Stand up, face me," Syd said. Izzie did what she said, though a bit slowly.

Syd took a breath again, then quickly undid her bra, tossed it on the bed, then bent over and took off her thong.

"Syd!" Izzie exclaimed as her roommate stood back up.

"Now you," Syd said.

"What?"

"Take off your clothes," Syd said. When Izzie went to say something, she added, "Please, Izzie, just...trust me. Strip."

Izzie hesitantly took off her pants and shirt. She hadn't put a bra back on after the gym but her panties had to come down with her pants.

They faced each other, Syd in lingerie and Izzie totally nude. Syd spoke first.

"How do you feel?" she asked.

"What do you mean?" Izzie asked.

"Just answer," Syd insisted.

"I'm...a little weirded out. Kind of cold. Confused, definitely," Izzie said.

"But you're not disgusted? You don't want to run away?" Syd asked.

"I guess not," Izzie said.

"Okay. Touch my breasts," Syd said.

"What!?"

"Feel me up. Grope me. Do it slow, like you always want guys to do and they never get it right," Syd said.

"Syd, I'm not-"

"Please just do it, Izzie. I'm not trying to make it weird," Syd said.

"Way, way too late for that fam," Izzie said, but she moved her hands.

She tried to keep in mind what Syd said. Honestly Izzie just wished guys would pay any attention to her breasts; her partners tended to give them a quick once over and seeing she didn't have much there except little cones with dark brown nipples, they moved on to more interesting things below her waist. She reached her hands up and cupped Syd's whole globes. They fit in her hands almost perfectly, and she gently squeezed them to feel them deform. There was more weight to them than her own and she found herself fascinated lifting and moving them around, since she couldn't do it with her own. She felt Syd's nipples harden at her attentions.

"Okay," Syd said, sounding a little breathier than before, "Now how did you feel about that?"

"Um...it was fine," Izzie said, "Maybe...kind of fun?"

"Fun?" Syd asked with raised eyebrows.

"Well, I don't have boobs like yours. I've never really felt any like that," Izzie admitted.

"Now I'll do you," Syd said.

Izzie would have covered her chest but Syd moved fast; her hands were on Izzie's chest immediately. She tried to copy what Izzie had done, but there wasn't enough of Izzie's breasts to fill her hands. Instead she pushed against Izzie's chest, using her hand to shift the tit flesh around. Izzie had to admit it felt nice, and after a moment she found herself wishing Syd would focus more on the nipples. Syd's hands pulled away.

"Okay," Syd said, taking a few more breaths, "ready?"

"For wha-whoa!"

Syd stepped forward and pressed her body against Izzie's. Their stomachs and chests pressed together and their legs intertwined a bit. Izzie felt the odd but stimulating sensation of Syd's breasts covering her own, and their nipples touched. Then Syd's hands were on her ass, gripping the cheeks.

"Grab my ass," Syd said.

Izzie tentatively reached back and grabbed the cheeks of Syd's ass. Syd's ass was a little smaller compared to her chest, and was wide without pushing out that much. Still, there was a lot of cushion to grab. It was firmer than Syd's tits, but still soft and grabbable. Izzie kneaded it a bit while trying to process the feelings of what Syd was doing to her own backside.

"God your ass feels...it's so firm, but soft too," Syd said almost in a whisper.

Izzie looked up. Their faces were close; she could feel Syd's breath. She looked down at her lips. Syd had put on light pink lipstick. It was still neutral, so it looked natural, but it was lighter than her natural lips. Izzie glanced up and saw Syd looking at her intently.

"Let's kiss," she said.

Izzie didn't object, but she let Syd take the lead. Her roommates lips pressed against hers. They felt like lips, but they were also different. Softer, certainly. More hesitant than anyone else she kissed. But also slower, more gentle in the approach. Their lips moved and pressed but there was no hunger, no hurrying to open or move on to something else. When they pulled apart their lips stuck a bit before coming away.

Syd stepped back and Izzie felt like it was twice as cold without the contact from Syd's body.

"There," Syd said.

"There what?" Izzie asked, and her own voice sounded a little breathy to her ears.

"That...that's probably what Charles would want. Some touching, us hugging, maybe some kissing," Syd said.

"Nothing more?" Izzie asked.

"Did you want to do more?" Syd asked.

"No," Izzie said, and she thought that was the truth, "but when I was there..."

"What?" Syd asked.

"You sucked on my nipples," Izzie reminded her.

Syd looked away with a bit of a blush and didn't say anything for a moment. "I...I was caught up in the moment. I'll try to control myself better. I need to get going."

Syd put her underwear back on and got her dress out. She put it on and grabbed her purse.

"Syd," Izzie said as she headed for the door. Syd paused and looked back. "I...I didn't mind that. I mean, I wasn't, like into it but...it didn't gross me out."

Syd smiled. "So maybe kissing me a little and feeling me up is worth an extra thousand then?" she suggested.

Izzie nodded and Syd walked out the door. Izzie sat and thought for a while though; she wasn't totally sure if she'd been talking about what they just did, or the nipple play from when she'd been at Charles's.

-=-=-=-=-=-

Izzie fidgeted in her seat in the conference room.

The room was in a hotel in the city near her college. It had been Charles's idea; the hotel had a restaurant in it that he told her was good, and he wanted a neutral but private location where they could discuss the contract and their potential arrangement.

It also has hotel rooms with beds in them Izzie couldn't help thinking. She knew Syd had told her not to fixate on the sex but Izzie couldn't help it.

Charles wasn't late, but she'd been early because she was worried about finding the room in the hotel. The fact that it was around the corner from the reception desk in a hallway that led to the ballrooms they used for wedding receptions or proms made her feel embarrassed and out of place. She'd at least worn nice clothes; black buttoned slacks that were a bit stretchy and hugged her ass well, and a light orange blouse. She'd tamed her hair a bit; it was still Frizzy but it fell rather than "poofing" out all around her head.

The man himself walked in a few minutes before six, their time to meet. He wore a polo shirt and dark blue jeans with comfy-looking shoes. He smiled when he saw her, but then it faltered.

"Isabella, are you all right?" he asked. He didn't have an accent that she could recognize, but when he said her full name he rolled the "l"s at the end a bit. That and his deeper voice hit her in her core and gave her an odd thrill.

"I'm...I'm sorry," Izzie said, though she wasn't sure what she was apologizing for.

Charles pulled a chair over and sat facing her on the same side of the table, though he was still far enough away that he couldn't reach her with his hands. "Tell me what's wrong," he said.

"This isn't worth it for you. Not with me," Izzie said.

"Did Sydney tell you that?" Charles asked, his tone dangerous.

"No!" Izzie said immediately, suddenly scared for her roommate, "She just...she told me some more stuff about this and...I just don't get it. I mean, I'm not worth $2,000 if we're not having sex, am I?"

Izzie was embarrassed all over again as she felt a tear leak down her cheeks.

"Oh Isabella," Charles said. He reached out a hand to her and she put her hand in his. He pulled her a little closer and rubbed the back of her hand with his thumb. It felt nice.

"I don't know who has told you you aren't worth it. Maybe it was your young friends back in your school days, maybe it was society. Maybe even your relatives or your parents. They're wrong. You are worth every penny and much more," Charles said.

"Is this where you tell me I can do whatever I want to if I put my mind to it?" Izzie asked.

"No," Charles said, "because I don't really believe that. Not everyone can do everything. I will say that I did not suggest this merely because I'm an old man who wants sex. Sydney has told me many fascinating stories about you. It's clear the two of you are very different people. I want to know you, have you as a friend and a companion as often as you'll allow it. I'll admit I like the company of young women more than any other group. I don't really get along with most men in general; I don't share enough interests with them. Older women are either obsessed with their children and their legacy or they're so independent that they just want a casual friend where sex is on the table."