Two Sugars: The Second Cup

"That can't be true with everyone," Izzie said.

Charles shrugged. "Probably not. But I also don't want to spend my time looking. I have money, I can pay to keep company with who I prefer to. I want to spend time with vibrant young women. You're energetic, you have a fresh outlook on life, I'm in a position where I might be able to guide or advise you, and many of you have a kindly, motherly instinct that sometimes comes out for me. Also, I'll freely admit I like the view, and what I have with Sydney is amazingly satisfying for me. I assume it is for her, too, or she's putting on an Oscar-worthy performance for me. How successful do you think I'd be if I tried to get the attention of someone like you or Sydney just by casually meeting them?"

Izzie had to nod in agreement. If Charles approached her at a bar she would have nothing but negative assumptions about him and wouldn't give him a chance.

"But...you have Sydney already," Izzie said.

"I do. You're not Sydney. And I don't just mean you look different. Sydney is very passive, very conservative with her life. She likes security, she doesn't naturally take risks. She's also a people-pleaser; she hates making other people uncomfortable. You're more of a free spirit. You don't dwell on things. That time at my house, if the positions had been reversed, Sydney never would have gotten out of that pool. She probably wouldn't have stayed for the skinny dipping, honestly."

"She did surprise me then," Izzie admitted.

"She was comfortable in that space; she knew all the parameters. And she was probably enjoying having the upper hand on you for once," Charles said.

They sat in silence for a while longer, Izzie considering what Charles said, Charles still holding her hand with a concerned expression.

"Would it help if we took sex off the table?" he asked quietly.

Izzie's mouth dropped open. "But...that's-"

"Not the point of this," Charles said, "I told you, I want to spend time with you. If it really will help you, think of it this way; I can get as much sex as I want whenever I want. Sure, Sydney is willing to sleep with me, but I've got money. If I want a threesome I can hire two girls to do that for me. I have connections, too; I can call some people up and they'll take me to bars or clubs where women will sleep with me just because I'm rich enough to get into them. Sex is not my concern. Being able to spend time with you is."

Izzie couldn't help saying, "But you still like these pants," and twisting a bit so her ass was more visible.

Charles smirked, "I'm not going to complain about them, no."

Izzie was shocked at how much his talking had calmed her down. She wasn't pushing her concerns to the back of her mind like usual; he was helping her process them.

"Would you like to talk some more?" Charles asked.

"Yeah, I think I would," Izzie said.

"Would you like to get some dinner while we do?" Charles asked, holding out his hand with a knowing smile.

-=-=-=-=-=-

Izzie curled up in her bed, hugging her body pillow tightly and enjoying the "snuggled" feel of it and her weighted blanket.

"Hey, you okay?" came from the other side of the room.

"Shit, sorry, I didn't mean to wake you," Izzie said.

"You didn't; I was reading," Syd replied, briefly holding up a tablet.

"Waiting up for me?" Izzie teased.

"Maybe a little," Syd admitted, "So how did it go?"

Izzie smiled to herself. "Per the terms of my contract, I'm not allowed to discuss details."

Both girls collapsed into giggles.

-=-=-=-=-=-

Izzie's arrangement with Charles was actually kind of intense compared to Syd's. Syd had dates with him Tuesday and Thursday night and then overnighted Saturday. As they'd discussed the contract over dinner (where Izzie found it a lot less stressful) Izzie had agreed to a date Wednesday, a "double date" on Thursday with Syd, and then overnighting on Friday. Charles had worried that Izzie would get "overwhelmed and sick of him" but Izzie actually preferred the prospect of having "Charles time" and then free time.

Syd had seemed disappointed and Izzie guessed she was hoping for the extra thousand that would have come from threesomes. Even though she didn't ask, Izzie explained it a bit.

"I can't even sleep with him right now Syd, I just...can't handle that. I'm sorry."

"No, no, I'm sorry, I...it's not my place to say anything. And I definitely can't dictate how you spend your time with him," Syd said.

"Syd, if this is a problem for you-"

"It's not," Syd insisted, though Izzie wasn't sure she believed it.

They agreed to start up the week after their "negotiation" meeting. Oddly Izzie found herself getting giddily excited at the prospect of their first date. Syd either got over whatever concerns she had or just got caught up in Izzie's excitement as they tore through Izzie's wardrobe wearing t-shirts and pajama pants, spending an hour trying on pieces of outfits.

The date itself wasn't that big of a deal, but at the same time it was. Izzie had legitimately never been on a date like it, even last time she was out with Charles. He escorted her everywhere and always touched her somehow; a hand on her elbow or the small of her back, or her arm tucked into his elbow.

She didn't remember where they'd eaten, but the food had been amazing. She spent the whole time talking about herself, and she unloaded a lot more than she had with any of her other dates. She actually stopped herself in the middle and wondered aloud why she was telling him everything about her family and home life.

"Because I don't matter," Charles said.

"What do you mean?" Izzie asked.

"You know I'm not going to walk out on you. I'm a sure thing. Even if in the back of your mind you think I'm just biding my time until we can get into bed, you know I won't get scared off by what you tell me. And you've clearly wanted to tell someone about all of that stuff."

There was a lull in the conversation then as Izzie thought about what he said. He pressed her to continue with a story she'd started and she hesitated at first, but soon she was rambling on again. By the end of the night she had a tear in her eye as she admitted she was just waiting for someone to knock her up and to end up like her mother: not keeping a boyfriend for any length of time, handing off her kid to her relatives when she couldn't get away from whatever job or jobs she held down to get her kid to adulthood.

Charles didn't say much after that, but he held her hand in a comforting fashion, and as they left the restaurant, she was tucked under his arm. She stayed snuggled up to him like that the whole ride back to campus. She didn't move immediately when the car stopped, but Charles didn't prod her to leave. She turned to look at him and saw him just smiling down at her slightly with a caring smile.

She reached up slowly and pulled his head to hers, giving him a heartfelt kiss. Their lips met and it was a pleasant, comforting feeling, being kissed back while wrapped in his arms.

"Thank you," she said.

Charles nodded and said, "My pleasure," and Izzie believed him.

-=-=-=-=-=-

The double-date was the complete opposite. The two girls regaled Charles with stories from campus. Syd admitted she did this with Charles a lot, but they rehashed some of the same stories she'd already told him because Izzie had to "correct" some details. They spent most of the night laughing at the retellings and the arguments over what "really happened," such as the unresolved debate over who had finally lost Izzie's favorite thong after it ended up in Syd's bed after a one-night stand their freshman year. Charles had walked out of the restaurant with the girls under each arm, all of them with full smiles.

Izzie was a little less excited about the overnight the next night. The pressure of Charles's bed couldn't be avoided. After the week of anticipation and the last two nights with him, Izzie's perspective had changed. She wasn't desperate to jump him, but she'd found herself imagining a scenario where she stood at Charles's pool table and he came up behind her, pulling off her nightgown and kissing her neck while his hands slid up to cup her breasts, and she found she wasn't put off by the idea. It even made her a little wet.

The car dropped her off at his house and her heart was beating. She fumbled typing in the code for the door lock. Charles met her as she came in. He took one look at her and pulled her in for a hug. She was tense for a bit, but he held her there and she eventually relaxed and just enjoyed the embrace.

"I'm not going to ask you for anything physical this visit," he said.

"That doesn't seem fair," she replied.

"We talked about this. I want your company, not your body. Being crass about it, even if I got frustrated with you being here all day, Sydney will be here tomorrow to take care of it," Charles said.

Izzie was a little surprised she didn't have a jealous reaction to that. She was actually kind of happy her roommate would get some attention; she was always more relaxed after she'd had sex with Charles.

He told her he actually had some work to do and a meeting that afternoon, so she should make herself comfortable, maybe get some of her schoolwork done. Most of her assignments were posted online, so Izzie took the opportunity to do that.

Two hours later she was done with all the work she could do and found Charles in his office. It was a little more old fashioned than the rest of his house, with a lot of polished wood furniture, including his desk, and a plush carpet. He had a modern executive chair instead of an old-fashioned looking one with maroon leather and gold rivets. He was in profile from the door, with a bookshelf behind him and windows to his left. He was hunched over, typing something.

Izzie felt an odd stirring as she looked at him. She walked over and stood behind the chair. The back was tall enough that she couldn't see over it, but she reached around and rubbed his shoulders. He stopped typing and froze for a moment, but then leaned back into it.

"Your hands are strong," he said.

"Rock climbing as my gym elective this semester," Izzie said, "My forearms hurt for a week."

"It feels nice," he said.

"It feels better in a bath," Izzie said.

She surprised herself a bit when she said that and she felt him tense up. She kept rubbing though. He didn't say anything while she did, but he did relax again. He actually settled back into his chair and Izzie thought he might be drifting off, so she stopped. She walked around and saw his eyes were drooping but he wasn't asleep. She leaned forward and gently kissed him.

"I'm going to have a swim in your pool," she said.

"I put your bag in the guest room," he told her.

"Don't need it," she said.

She felt a thrill as she walked out of the room. She was a little shocked that she'd gone from "nervous about a hug" to "actively seducing him" in only a few hours, but it felt right.

She walked out to the in-ground pool and left her clothes on one of the loungers. Naked, she dove in. the water was cooler than last time; she guessed either Sydney or Charles had turned on some heaters during their previous visit knowing Sydney would use the pool. She didn't mind; it literally cooled her down some and let her think about what she was doing.

There may have been a little bit of competition after Charles mentioned taking care of business with Sydney if she wasn't available. She thought Sydney was prettier than she was, and part of her did want to prove she could get Charles's attention just as well. She also felt like there was an imbalance in their relationship right now. Not only was he paying her, letting her stay at his house, and feeding her, she'd also unloaded a bunch of clueless college and family drama on him unprompted. She wanted to give a little back.

She swam around, enjoying the sensualness of the water running over her body. She'd felt this last time; the water moving over parts usually covered added a thrill and extra stimulation to the experience.

She didn't know how long she'd been swimming, but her fingers were a little pruney when Charles came out. She was a little disappointed he wasn't in a robe like when he'd come out with Sydney, but his gaze was still fixated on her. He didn't sit in a lounger, but he stood near one. Izzie swam over to the steps and walked out, not trying to cover anything. Her nipples crinkled from the cold and her hair stuck to her back.

She walked straight over to him and stood in front of him, invading his personal space. She was willing, but she still wanted him to make the first move; she wanted him to want her, to take the last step.

He slowly cupped her face in his hands and then kissed her. It was slow but intense. His lips moved against hers. His tongue probed and licked at her lips, but it wasn't desperate for forceful. Izzie was impressed by his control and restraint. Most of the guys she knew wouldn't have let her even get to them if she walked up naked; they would have run over and grabbed her.

It was a major turn-on.

She was a lot more aggressive with her tongue as their mouths opened. They swirled and explored for a while before finally pulling back. She was panting. He breathed deeply.

He gently pulled her over to the lounger. With gentle guiding he got her to kneel on all fours, facing away from the pool. He went behind her and she felt his hands on her ass, the fingertips tracing down.

Charles was an ass man, and he'd complimented hers the first time he saw it up close. Now he thoroughly explored it. His hands cupped and traced it, he squeezed to feel the play of the flesh and muscles. He moved the cheeks around, giving her a deep long crack as he pushed them together, then exposing her rosebud as he pulled them apart. His mouth got involved in the exploration too. Licks, kisses, and teeth dragging on her backside joined the touching and groping of his hands.

Izzie had gotten lots of compliments on her ass, and many of her partners made sure to grab, hold, and even spank it. She'd never had anyone worship it like Charles was doing. It was turning her on even more.

Then his mouth started circling. He licked and kissed around, spiraling inward, and she knew what the center was. Soon enough his flattened tongue swiped over her crinkled hole. Then again, and again. He'd done this to her before, during the threesome, but he hadn't taken the time he was now. His first lick made her flinch. He kept up until they were mere twitches, responses to the nerves being excited by his tongue.

When his tongue probed her hole, she moaned. The pointed tip writhed around as if tracing the folds. Izzie found herself pushing back. Charles intuited her desire.

His tongue pushed against her hole. It took some doing, but she let him in. His muscle pushed around the edges, lighting up her nerves. She clenched those muscles and the ones in her pussy, amazed again at how erotic the sensation was.

She would have let him do that for hours, but he had another goal in mind. She felt his fingers slip between her folds and slide into her. She was soaked and his two fingers weren't unusually large, so they slipped in without a problem. He'd kept one finger outside and that slid up and grazed her clit. A louder moan came out of her then.

He set to his goal then; his tongue probing her ass while his fingers plundered her sex, one always outside sliding along and rubbing her clit. She felt her juice leaking out of her pussy and onto his hands. He pulled back for air at one point and her cheeks came together. She put her face down on the lounger and reached back, spreading herself in a silent plea for him to resume eating her ass. He obliged a second later, pushing his tongue even deeper into her back hole.

Her orgasm hit her like a shot. It seemed like she was just enjoying the pleasure and then it suddenly spiked. She jerked forward and almost fell off the lounger. Charles held her as she shuddered through the orgasm, hugging herself and arching her back. The squeezing of her cheeks and thighs together seemed to excite all the same nerves Charles worked on. She felt pleasurable aftershocks for some time.

She also felt a bulge in his pants.

She turned her head and kissed him again, not even pausing when she remembered where his tongue had been. Her hands slipped down to his pants.

He stopped her. Izzie looked up at him, confused.

"I don't mind. I want to," she said.

"I know, Izzie. I do too, but you aren't prepared," Charles said.

Izzie raised an eyebrow. "I've done this a few times, Charles. If you thought I was a virgin-"

"No, no, that's not what I meant," Charles said, "What I do with Sydney...It's not a preference, it's a precaution."

"You mean anal? How is that a precaution?" Izzie asked.

"I don't like condoms. I also don't want more children," Charles said.

"I'm on the pill," Izzie offered.

"I just don't want to take the chance," Charles explained, "I know it's silly, but I have a lot of hangups about sex. I'm only really comfortable with anal."

"Not even a blowjob?" Izzie suggested.

Charles shook his head, looking down at the ground. Izzie realized she'd not only killed the mood but probably had embarrassed Charles. She moved over and hugged him. She was still nude but she didn't try to make it erotic; she just wrapped her arms around him from behind and leaned on his shoulder, pressing against him until she felt him relax a bit. She leaned up and kissed him on the cheek.

"You made me feel wonderful," she whispered to him. That seemed to reassure him enough to reduce the tension.

They both managed to avoid making it awkward after that, and by the time they sat down to dinner, courtesy of Charles's amazing cook Bartolo, they were chatting away comfortably. It wasn't the deep, intimate baring of souls from their last dinner. Charles instead picked up on some of the story threads from their double-date with Syd, and he dove into the more practical concerns around each of them. Izzie found herself surprised at the interpersonal situations Charles figured out just from the one-sided stories he'd heard. When she pointed that out, he shrugged.

"People are people. There are patterns, as much as some people hate being labeled and pigeon-holed. I do it with Sydney all the time. I've been on her case for a while about Stuart," he said.

Izzie recalled a guy in their class who had some success in the school's track and field program. One of their friends Carla was on the team, and they'd been to a few parties with that crowd, as well as hanging out at Carla's dorm, where a lot of the track team dropped in and out. As she thought about it, she realized Stuart had been there most of the time.

"You think he's after her?" Izzie asked.

"Definitely," Charles said, "You know he literally carried her on his back to your dorm that time when your quad flooded?"

"Wow," Izzie said, remembering the period where a full foot of standing water flooded part of the campus. If you didn't want to wade through it, getting from one side to the other was a full half mile walk because of the placement of buildings and the water. "And she didn't clue into that?"

Charles shook his head. "She just thought he was being nice."

"Well, he probably didn't mind those C-cups pressed up against him the whole time either," Izzie said.

"Maybe. But based on the other stories she's told, I'd bet money he's sweet on her. I've told her to ask him out a few times, but she insists I don't know what I'm talking about," Charles said.

That shocked Izzie. "Wait...you told her to ask him out. Like, recently?" she asked.

"Yeah," Charles confirmed.

"But...what about..." Izzie wasn't sure how to phrase the question.

"Izzie you read the contract. As long as you keep me informed of the fact that you have another partner I don't have an issue with it. I don't like to focus on it, but this is a business arrangement. You aren't supposed to put the rest of your life on hold for me. Another guy I know was with his..."