Later that night...

Eleanor woke up in the middle of the night and stared at Simon's ceiling. After their shower, he'd told her to stay the night with him, and she'd said "yes, daddy" without a second thought. A man twice her age, whom she'd just met tonight - and not only did she let him fuck her roughly, not only did she let him take her virginity, but she was staying the night with him without hesitation.

And as she mused about it all, she felt herself getting hard again.

It was impressive how he made her feel safe and taken care of, even while he was fingering her ass in the nightclub or pinning her to the bed or bruising her ass. Maybe this could be a thing. If he wanted. Eleanor rolled onto her side, snuggling up against Simon's chest, and went back to sleep.

Sun streamed in through Simon's windows, and Eleanor awoke with a smile. Everything about last night seemed surreal - not because she was too drunk to remember clearly, but because it didn't seem like it could truly be real. But she saw Simon sleeping next to her, and saw the massive bedroom they were in - it was real.

And she was horny again. Her ass was a little sore from losing her virginity, but she was sure she could go again. Simon was still sleeping but, well...she could incentivize him to wake up.

Eleanor slunk down under the covers and got onto her hands and knees. Simon's cock was there in front of her, pretty and hard. Her mouth watered a little as she looked it over. She took hold of it and slowly sunk her mouth down onto it, trying to see how deep she could take it on her first try.

She started sucking and bobbing, happily slurping and making no attempt to be subtle or quiet. Simon started reacting quickly...first quiet moans, then shifting...then he lifted the covers and looked down at Eleanor.

"Morning daddy," she said with a smile, then went back to work. He watched her quietly for a while with a small smile on his face, and she did her best to maintain eye contact.

"You know," he said after a couple of minutes, "you're pretty good at that for someone who was a virgin until last night."

Eleanor blushed. "Thank you, daddy." She pushed her head down on his cock one last time, as deep as she could go, until she gagged. "I woke up horny. Can I ride you?"

He laughed. "Aren't you an industrious one? Well hold on a second. Let's talk." Eleanor immediately got anxious, but Simon pulled her into his lap, his wet cock pressing against her butt, and that helped her feel less like she was about to be rejected.

With his arms around her, Simon started. "Now, I don't make a habit of fucking someone repeatedly unless we have some sort of...agreement or relationship. I'm not monogamous, by any means, but I like for me and my sexual partners to have an understanding. So I'd like to know what you want out of this."

Eleanor was rapt. She was not expecting this conversation.

"Of course, if you want to just fuck, then say goodbye, that's totally fine. A one night - and morning - thing. No problem. But if you want this to be a regular thing, I'd like to know now so we don't disappoint one another. We should get on the same page."

She hadn't been thinking that far ahead. She was just horny. But now that he brought it up, the idea of fucking once more then finding someone else, hoping they'd fuck her as good as he had, didn't sound as much fun as getting his dick again and again. "What do you mean by...a regular thing?"

"Well, I mean coming to an agreement about what we want from each other. I don't want a girlfriend...I'd prefer that to be a woman closer to my own age, with experiences more similar to mine. But a different kind of arrangement..." He trailed off, but Eleanor's undivided attention motivated him to continue. "Well, Eleanor, I'm a rich man. You're a young woman. Going to college, right?" She nodded. "You have needs, and so do I. I'd love to be able to dress you in pretty things, shower you with attention, make you feel good. And in exchange, you'd come when called, accompany me to parties every now and again, let me show you off...that sort of thing. And of course, we'd fuck."

Eleanor was rock hard. "You mean like...a sugar daddy?"

Simon smiled. "I do. You've already been calling me daddy, after all."

Eleanor blushed. "Kat said I should try that. She said you liked it. Turns out...I do too."

Simon laughed. "I can tell. I like hearing you say it. So what do you think?"

"You would...pay for things?"

"That's right. Any time we're together, I'd pay for what we're doing. I'd buy you clothes. I'd send a car to pick you up. You'd be spoiled."

"I...I like the sound of that." Eleanor pondered for a moment. "And I'd just owe you like...some of my time?"

"More or less. I'd ask you to accompany me to things. I'd ask for photos. I'd show you off to my friends. I wouldn't want to stress you out, though - if you share your school schedule with me, I would make sure you have plenty of time for class and school work. And your own friends, of course."

"O-okay." Eleanor was stunned. This was...amazing. He liked HER enough to...want to buy her things? He wanted to show her off? Her chest was flushed. Her nipples were hard. She wondered if he'd ask her to fuck his friends. She wondered if she'd say yes.

She probably would.

"Okay, daddy. Yeah, I like the sound of that. Let's do it."

He took her chin in his hand and kissed her. "Wonderful. Good girl. Now that that's decided, yes you can ride me."

Eleanor got right to work.