Two Sugars: The Second Cup

"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.