An adult stories – Two Sugars: The Second Cup by Chris6160,Chris6160 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.”
“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…”
“Sugar baby,” Izzie said.
“I know, but the term seems so…gross. Anyway, he was with her for two years, and during that time she met, fell in love with, and got engaged to a guy. He was invited to their wedding, which I think is a little odd, honestly, but it didn’t sour anything.”
“That just seems…weird. I mean, I know you aren’t just paying for the sex but Syd and I…we aren’t just hanging around looking pretty. I mean, that conversation on Wednesday was intense.”
“It’s something both parties need to keep in mind,” Charles said, “This is business. I’m not trying to court you, and our relationship won’t progress beyond a certain point. You’ll probably never meet my son, for example, unless it’s by accident. You’re never going to introduce me to your parents. You aren’t going to have my child, and I’m not writing you into my will.”
“That seems kind of harsh,” Izzie said.
“It is, but like I said; it’s to protect us both. At the same time, you don’t have to worry about other hang-ups a relationship would bring. If you come out of this weekend really frustrated, for example, you can go back to campus and find a nice boy to work that out with. And as I said, if we aren’t intimate, I’m seeing Sydney tomorrow. But even if she doesn’t want to be intimate, I can find another woman and it doesn’t affect what we have. I know that’s bothering you; I can see it. This is why I don’t like to talk or think about it.”
Bartolo brought them small chocolate cake slices for dessert that tasted and felt like soft fudge with a frosting shell. Izzie swore she almost had an orgasm eating it, and that she’d probably need to do an extra day at the gym because of it.
Charles suggested they watch a movie after the tense day they’d had. He picked one featuring Robert Redford but when he looked baby-faced young. It held Izzie’s attention well enough but she found more of her focus on the position she was in; spooning with Charles with her as the little spoon.
They went to bed after the movie. Charles had pajama pants but no top on. She decided on a nightie with a thong. They weren’t particularly sexy, but it was hard to look modest in those. She wondered if it would get a reaction from Charles and he did smile when she walked in the room, but other than putting his arm around her and sliding it up under her breasts, he didn’t make any moves.
-=-=-=-=-=-
She woke up at 5:30. She didn’t know what jostled her, but she’d been dreaming again. Weeks ago, she’d dreamt of watching Charles and Syd fuck, and it had turned her on. That night, her dream had been of Charles with her, and Syd watching them, rubbing herself off as she watched the action. Charles had been taking her ass, too, and she was confused about how that had come through in the dream.
Waking up gave her a clue; she had to pee badly. Also, Charles was hard, and pressed up against her. Apparently her brain translated the rod between her cheeks and the pressure from her bladder into anal sex.
She slipped out of bed without disturbing him, at least she thought she did. When she got to the bathroom she smelled her own arousal; the dream had her worked up. She noticed he was down to the last sheet on the toilet paper, so she looked for a replacement in his bathroom. That’s when she found the drawer.
It had cases that held a few of the plugs like Sydney had worn. There were also several bottles of lube. Finally there were some boxes that screamed “drug store” from the packaging. She took one back to the toilet and skimmed it as she did her business.
It was an enema kit. Charles’s objection to her, you aren’t prepared, popped into her mind.
She was horny enough that she’d thought about rubbing one out after she peed. Now she had a different idea. She thought it was a little crazy, but she went for it anyway.
A while later, she came out of the bathroom. One hand she held facing up, making a little cup. She ignored the odd feeling of her ass sliding against itself. She gently pulled the covers back.
Charles was still obviously hard; his pajama pants were loose and without her blocking him, he tented them. She gently exposed his cock, which was above average size. She couldn’t remember if he’d been this hard when she’d been with him and Syd. She’d had two fingers in her ass just now putting in the lube and they’d felt huge. His cock was at least twice as thick.
She rubbed the lube cupped in her hand on his member gently and slowly. Somehow he stayed asleep. Then she slipped into bed.
She kept a hand on his cock as she backed up, until the tip split her cheeks. She aimed him toward her rear entrance and slid back. The cock felt huge. She expected it to maybe feel like a thick finger, but it was more just like a block with a spongy tip against her ass. The lube helped, but she would have to relax.
She thrust backwards shallowly, letting the tip bounce against her asshole. It pressed a little farther in each time. The sensation was interesting. There was tingling and a little bit of sting. Then she thrust more and the stinging increased to burning. She flinched off, then pushed herself back again.
“Isabella,” Charles said and she felt him pulling back.
Izzie reached around quickly and clamped her hand on his ass. She couldn’t actually stop him from moving, but it did stop him.
“Please,” she begged, “I want you.”
“You-”
“I was in the bathroom for a while,” she told him, hoping he’d pick up on the details. She smiled to herself when she felt his cock flex.
“Are-”
“Please Charles. I need your cock in me. I need your cock in my ass,” Izzie said.
She heard Charles exhale, then one of his hands settled on her hip. He started thrusting in quick, shallow thrusts, similar to what she’d been doing but faster. He went faster than she had, and her anal ring gave way to his rod. She let out a moan at the sensations; the burning increased but so did the tingling pressure of an invader in her ass.
There was a “pop” of sorts and the pain flared. She yelped and Charles stopped, but she held him there again. She realized his head had just gone past her ring, which amazed her because she thought half his cock was in her already. She let out a breath and said, “Keep going.”
“It helps if you bear down,” he said.
Izzie tried that and it did help him to slide in. Soon his cock pushed even deeper into her. It already felt like he was in her stomach. The burning was lessened as her ass adjusted to him, and now the rubbing and the excitement of her rear nerves were more present. There was also the pressure of being filled from behind.
Charles began really thrusting since he had the room. He still went deeper with each thrust, but Izzie felt real movement of his cock in and out of her ass.
This is it, Izzie thought, He’s fucking my ass now.
The idea of it increased her enjoyment; her accomplishment at meeting his sexual needs, the naughty nature of the act, and a bit of the sense of surrendering to him, letting him claim her. She let out another moan as these thoughts meshed with more sensations of him pushing into her ass.
A few more thrusts and then his hips hit her ass. She grunted as he bottomed out, absorbing the feeling of him fully thrust inside her. She reached around and brought his hand up to grab her breast. He cupped the small mound of flesh and caught her nipple in the folds of his palm. He pulled back and thrust again, slapping against her ass. Then again and again.
He build up to a steady pace, making his cock piston into her ass and out again, sending a burst of sensations up through her each time he bottomed out. It even tickled her clit a bit, and she could feel her juices leaking down and helping to lubricate his shaft. She thrust back as he came forward, the slapping of their bodies getting louder. She wanted it harder, wanted those impacts to tickle her nerves even more, and hopefully travel through to her clit. She used a hand to cover the breast Charles wasn’t using as a handhold and teased her other nipple.
Charles kept slamming into her rear for a while and then he stopped fully inside her. Izzie groaned at the feeling of being stuffed full again. She was a little frustrated that it was over, then she realized she wasn’t feeling the telltale flexing of a penis pumping cum into her. She was about to ask what was wrong when Charles’s hand left her breast and moved to her thigh. He pulled her leg back so her knee rested on his leg. She wondered briefly if this gave him more leverage or something.
Then his hand practically slapped down on her pussy and his thrusting continued.
She howled. The thrusts slammed into her like before, forcing her bowels open and scraping her nerves, but now the thrusting pushed her pussy along his hand, where he’d positioned his finger to drag over her clit. In no time she was helping this process, slamming her ass back against him until the impacts stung against her skin, then pushing forward to grind into his hand. He pressed even harder after he almost slipped out of her.
She came only a few thrusts later. The initial ass fucking had worked like foreplay for her clit; it was primed and ready to go off with only a little attention, and the new position provided it. She hugged herself and curled forward in the bed as her orgasm exploded. She felt Charles slowing.
“Don’t stop. Don’t fucking stop!” she begged, and he obliged.
He kept fucking her hard right through her orgasm. She’d trapped his hand with her thighs and she still got all the same sensations from his cock in her ass, but now they mingled with her orgasm, enhancing and extending it. When the orgasm died down she was curled almost in a fetal position, Charles still pumping away, the impacts on her body still grinding her pussy against his hand. She relaxed a bit, which let the impacts move her even more. Her pussy was a bit overstimulated but she didn’t care; the start of the whole encounter taught her to push through discomfort and pain if there was pleasure involved, and there was still pleasure.
She heard Charles grunting, and his breath was heavy enough to blow her hair around. He was getting winded, and after this long she thought he was either getting close or he’d never cum. Then she felt him get even wilder in the rough, frantic pattern guys on the verge sometimes had. His thrust suddenly got shallow and fast and then he dug his fingers into her hip as he slid in.
She felt his cock pulsing in her ass and knew she was getting his cum in her colon. She thought they were done, but Charles apparently didn’t want to leave her like that; as he came his fingers suddenly went crazy between her legs. Izzie wasn’t ready for it but she didn’t stop him. His fingers blurred over her clit, and the feeling of him still lodged in her ass, plus the mental satisfaction at bringing him off, let her ride that to another orgasm.
She gripped his wrist to stop him and he got the idea. Her second cum was calmer, waves of pleasure bringing shudders to her body rather than the explosion of ecstasy of her first one. She settled back into her lover as both of them came down from their sexual highs. Unable to resist being a little naughty, she also brought his fingers up and licked her juices off his fingers as her orgasm settled.
“Thank you my dear Isabella,” Charles whispered breathlessly.
“Any time Charles,” she said, “I mean it.”
He pulled her back to him in a comforting cuddle. She looked at the clock; between her prep and the actual act, they’d been at it for more than an hour. She hoped Charles slept in on Saturdays because she wanted to stay in bed.
As her head settled back against the pillow, her traitorous brain gave her an image to deal with. She was settled against Charles, his cock softening and slipping out of her ass, her own flavor from his fingers in her mouth, but she imagined Syd, lounging naked just in front of her, one leg cocked, her hand lazily stroking her own pussy, and one eyebrow raised; expecting…waiting.