Two Sugars: A Last Cup

They'd rearranged their contract. Instead of the schedule of dates, for the first two years of medical school she lived in his house, driving her car to classes she couldn't do online, and eventually to her residency. Oddly, despite providing her with room and board, he increased her pay, and demanded less of her attention. She later discovered he'd also covered a large portion of her school bills.

When she graduated, she'd bought him a graduation present; a colleague of hers in medical school who had a few dozen pictures of her 36E, 28, 38 body with long red hair available online for paying customers. For a thousand dollars, she'd come with Isabella back to Charles's house for dinner, and then they'd recreated the threesome they once had with Syd. It hadn't involved the maid outfit, but it had involved both Isabella and Charles pounding cocks into her holes at the same time. Later she'd run into the classmate in the cafeteria of a hospital and she'd exhaustedly admitted to Isabella that she'd be willing to go again free of charge if only Bartolo would make her another meal.

After medical school, Isabella had pointed out to him that she wasn't a young college co-ed anymore, and she'd understand if he wanted to "find a better investment." He'd refused. She tried to argue, but Charles had dropped another bit of philosophy on her.

"If you point out to someone that you're taking advantage of them, and they still agree to it, don't keep trying to change their mind."

-=-=-=-=-=-

Being careful of the IV lines and monitors he was hooked up to, Isabella slid onto the bed. It was closer to a double, so there was room. She stretched her body out along his and nestled her head into his shoulder. They talked for a long time, catching up on what they'd done. She told him about Javier's traditional but sweet proposal several months ago, and how their long relationship was making both their families anxious. She claimed they were both in the middle of battling their families and trying to keep the guest list under 150. They'd originally hoped for under 100, but that had been a nonstarter.

She did most of the talking. She always had. Charles didn't have a lot going on before, when they'd just been "sugars." Now, he might have stories, but many of them would be of pain, misery, and challenges he faced trying to keep his failing body functional.

"I'm sorry," Isabella said after a long time silent, "I shouldn't have left."

"You needed to be on your own. You needed to cut your last safety string," he said.

"It was stupid. You're the best father I ever had."

He chuckled, which turned into coughing she had to help him through, but he still smiled afterward and said, "I don't know that I'm comfortable with that description given everything we've done."

"Haven't you heard? Incest porn is all the rage now. Every other girl is either getting asked to call their partner 'daddy' or they're doing it on their own," Isabella said.

"Never been my thing. I felt dirty enough getting girls less than half my age to come to my house," he said.

"The girls never minded," Isabella said to him, "I've never known what I am to you, but I guess...you're the best man I've ever met."

"Don't let Javier hear you say that," he said.

"Javier knows. Like you said, he's not dumb. You have a huge part of my heart Charles. You always will. If he can't deal with that, then he needs to take this back," she said, flashing her fingers in front of them and making the diamond sparkle.

"You owe him the whole story. Otherwise you're negotiating in bad faith," Charles said.

"I know that. I was going to tell him a month ago. Then I got your letter."

Charles started shaking. Isabella looked up in alarm, but then she saw he was sobbing. In relief. She let him cry, then he gripped her hand as tight as he could.

"I...I hoped when you came here...but I couldn't be sure. I've thought of going to Canada for the past year, but my son...I love him, but he has me tied up in a legal battle about my cognition. I can't travel on my own like this."

"I know, Charles," Isabella said.

They spent a while just silently snuggling together, broken only by a bathroom break that Isabella took. After some time, Charles spoke.

"Isabella?"

"Yes?"

"What did you do?" Charles asked.

"What do you mean?" Isabella asked.

"You know what I mean," Charles said.

"Do you mean the hard cock that's pressing into my thigh now? I assumed it was remembering all the good times we've had together," she said.

"I'm a sixty-seven year old cancer patient with ALS," Charles said, "Do you know what it takes for me to get it up nowadays?"

"Apparently, it takes one hundred milligrams of sildenafil, administered by IV," Isabella said.

"Why did you give me Viagra?" he said.

"Because you taught me that if someone wants something from you, you make sure you get compensated for it. So here's my deal."

Isabella pulled the blankets down out of the way. Charles didn't have pants on; it interfered with a lot of things that needed to happen with him. The medical problems he had hadn't diminished his cock at all, at least not once someone got it hard. She straddled him, her knees on either side of his thighs, and stripped off her medical coat.

Underneath, she had nothing on.

"If you want me to do this for you, you're going to fuck my ass. You're going to keep fucking my ass until I'm satisfied."

"But-"

"Javier doesn't like anal. And you know there was at least a year where I was fucking both of you, so don't give me any shit about cheating. I want a nice, deep, hard ass fucking before I probably have to give it up. And no one knows how to treat my ass better."

"I...don't know if I can," he said.

"Well you'd better find a way," she said, "Find that last bit of energy, that final push, and give it to me. Because if you don't, that special chemo bag I brought with me is getting poured into your swimming pool."

"Even after the work you went through?" he said.

"I win either way, Charles," she said, briefly choking back a tear.

There was a long pause, both of them looking at the other with desperation in their eyes.

"Get the lube," he said.

She actually had to go all the way back to his original bedroom to find some. When she did, she wondered if it was the same bottle she'd used last time they'd fucked. Fortunately, if so, it didn't go bad.

She came to the bed and coated his cock. Unlike almost every other time they'd fucked, she got onto her knees facing him. Her tits hadn't grown very much even though she'd gained some weight. She took his hands and planted them over her chest, his palms on her nipples. Then she reached back and found his lubed shaft. She aimed him and slowly settled back. The tip parted her actual ass cheeks easily enough, but then hit her sphincter. She'd worn a plug to his house and only just removed it, but it wasn't an easy entry. She bounced her ass on his cock, the tip slowly pushing its way in. Her ring spread around his head as her body bounced atop him.

She let out a gasp as her ring pushed down and past his head. Once past the ridge, she slid the rest of the way slowly but surely. Isabella closed her eyes and absorbed the feeling of having a cock in her ass for the first time in almost two years. The burning, tingling, and pressure were just like she remembered, as was the feel of Charles's cock. She settled down onto his hips when he bottomed out and wriggled her hip a little, slightly stirring her bowels with his penis.

She started fucking him then, squeezing as she rose and bearing down on her descent. Charles's eyes were closed and his mouth open as she rode him. She didn't know for sure, but it was possible he'd been celibate for the two years they'd been apart. Of course, ALS and cancer treatments weren't known for increasing libido.

She imagined two years of built up cum inside him and suddenly wanted it all. She slid her hand down to her pussy and rubbed. The idea of getting him off and the feeling of getting fucked sent her over the edge with her first orgasm. She rode through it, letting the continued pressure of his cock stimulate her through the aftershocks. Her pussy dripped juice down onto Charles's cock, helping keep him lubed and sliding inside her. His hands started squeezing her tits and the pressure on her breasts, as well as her nipples getting pinched in the folds of his palms, sent more pleasure and jolts through her body.

After a few minutes she saw him looking intently into her eyes. She slowed.

"Let me see it," he said quietly, already sounding winded.

She knew what he meant. Without coming off of him, she spun, feeling his cock twisting in her ass. When she'd completely reversed her cowgirl stance, she resumed her pumping. She moved slower; she had seen at least one ED case of a man's penis being fractured from his woman being too aggressive in this position. She made sure not to push too fast or too hard, just enjoying the slower, smooth glide of his cock into her ass.

His hands, now free of her breasts, settled on her rear and kneaded her cheeks, grabbing and groping the curves of soft flesh. She moaned at his attentions. They weren't very stimulating physically, but the mental rush of having a man worship her ass again added mental fuel to her smoldering sexual fire.

Eventually his hands rose, and she felt his fingertips tugging. She slowly let herself lean back. Her shoulders rested just beneath his.

"Is this okay for you?" she asked.

"I don't care," he said, "Please, keep going."

She used her abs and thighs to fuck now. The angle was better, so she went faster, and his cock went deeper.

"Your Isabella is fucking your cock with her ass, Charles," she stage whispered to him. She brought her hand up and circled his head, rubbing her fingertips on the baldness of his scalp. She felt tears again at the loss of his nicely coiffed salt-and-pepper hair that she used to run her fingers through. And the loss of strength that meant she was doing all the work of fucking him, and he was now too weak to slam his hips into her ass as he once did.

She rammed herself down instead. In the back of her mind she worried about breaking or dislocating his hip, but he could tell.

"Do it. Fuck me Isabella. I want it," he said.

She twitched her hips in a frenzy. Her ass slapped against his skin. She felt stinging from the impacts. The muscles in her thighs and abs burned. Charles managed to slip his arm around, and his fingers found her bare cleft. He slipped his middle finger in and it grazed her clit as she thrust up and down. She moaned and grunted with each piston move, and Charles gasped and groaned.

"Oh fuck, oh fuck, oh FUUUCK MEE!" she shouted as her orgasm hit. It radiated out from her ass, her pussy seeming like an afterthought as the shocks of pleasure rippled through. She twitched and moaned.

Then she felt it. As her ass clenched through the throes of her cum, she felt the pulsing of Charles's cock. She'd done it; she fucked him to orgasm, and his cock was unloading his built-up spunk in her ass. She squeezed his cock with her sphincter a few more times, imagining she forced more of his juice out.

She heard his breathing slowing after a while, and she rolled, his limp cock slipping out from between her cheeks. His hand reached out and held her arm as she sat up. She looked at him and he had tears in his eyes.

"It was perfect," he said, "your ass...let it be perfect. Don't make me live without it."

Isabella suddenly had to clamp down on a massive sob that wanted to burst from her chest. "I...I promise, Charles."

"My wonderful Isabella," he said softly as his eyes closed and his head settled.

Isabella went into the master bathroom, where she'd stashed her go bag. She pulled on panties with a pad attached a little farther back than normal, yoga pants, and a long-sleeve shirt, then put her coat back on over it. She grabbed two pouches and went back to the game room, now the infirmary.

Using the key she'd found at the makeshift nurses' station, she unlocked the refrigerator. She replaced the next saline pouch stored there. Then she replaced the one remaining pouch with yellow-tinted liquid and biohazard and poison warnings printed prominently on it.

When the nurse came back, she said, "We talked for a long time; I probably kept him up too late."

"Oh don't worry about it," the sweet, older woman said, "Nobody ever visits him, he seems so sad and lonely. I'm glad you could drop by."

"Anyway, his saline will probably need changing in an hour or so, and it looks like just one chemo bag left?"

"Yeah, we're getting more in tomorrow. Poor guy. They've got him on an aggressive regimen but if he wants a chance of beating that cancer it's the only way," the nurse said.

"Right," Isabella agreed, tears in her eyes.

"Don't worry honey, you'll be able to visit him again, I'm sure," the nurse said, patting her hand.

Isabella held it together until she got outside and into her car. Then she spent ten minutes wailing and leaking tears onto her steering wheel, looking up at the corner of the house where Charles lay.

The fentanyl she'd mixed into the saline bag ensured he'd sleep well past sunrise the next morning. It also helped that he'd been prescribed it a few weeks ago when he'd had trouble sleeping after chemo.

The chemo bag she'd left had fifteen times his usual dose of two of the more dangerous drugs in his regimen.

For the rest of Charles's life, he wouldn't have to deal with anything except the memory of having sex with Isabella's delicious ass. She wished there was any other way, but she kept replaying the "lesson" he'd given her when they were fighting about her being his caretaker.

"There are times when someone makes a demand, and your only choices are to meet the demand or change the relationship forever. Do not rush those decisions, and make sure you can live with the consequences."

Isabella decided to meet the demand. And she could live with it; she might have finally made up for all the money and wisdom he gave her over the years.