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The Arrangement (Jaycob x EtherealElvenPrincess) (NSFW images)

Her arching back almost drove him deeper into her, and he had to be careful not to accidentally break his little OnlyFans model. He could, indeed, tell that she wasn't used to anything or anybody of his size using her this way, but he resolved to train her properly once he was done. The feeling of control, from feeling her submit to him earlier to feeling her try to accomodate him now, was heady. He let out a low groan, withdrawing from her, giving her less experienced hole a break.

"Good girl, Princess. I love how tight you are, but we might need to train you a little before you're ready for that." He gave her a tight smile; a part of him had wanted to simply pin her down and take her, but he was in control. "Besides, I don't know if I'm ready to cum again just yet..."

He patted her ass, not hard enough to sting, but enough to watch it bounce. He enjoyed it enough to do it twice.

"Why don't we wash up a bit and you can put on a nice outfit, your pick, you can even use that one again, and you can ride me?"
 
Hearing his voice not only complement her but treat her sweetly made her calm down a little and relax but even so he cannot fitfully inside her not right now. If he attempted what he wanted to do he would’ve easily broken her in this very instant.

Nick patted her ass and she whimpered feeling him still inside but muttered a tiny squeak of a yes but he mentioned getting cleaned up she could use a bath right now I really hot one. Nick patted her ass as she whimpered feeling him still inside but muttered a tiny squeak of a yes when he mentioned getting cleaned up she could use a bath right now a really hot one.

Perhaps her sugar daddy was hoping to take one together and maybe she did too because she could use a massage right now and she was already feeling sore and then it had just begun. They could do so many things in a full night but they didn’t have to rush it since he agreed to stay over they could take their sweet time exploring each other’s bodies.
 
She agreed, not that he’d expected otherwise. She was a mess of his cum, from her cheeks down to her tits, and of her own, down her thighs and ass. She had been pretty thoroughly fucked, too, in every hole. Nick expected the was tired and a little sore - he could use a short break, himself.

He got off the bed, extending his hand, palm up, for her to take.

“Why don’t we take a shower first? Then we can settle into the bath with our bodies nice and clean. Since you’ve been such a good girl for me, I’ll even give you a massage. They don’t have any oil here, but they have lotion and that’ll do just fine.”

He looked at the bed. It was, by now, an absolute fiasco.

“Do you want me to call to have our sheets changed? And probably some more sent up?”

The latter question was intended to imply to her that she wasn’t done just yet.
 
“A bath sounds really nice right now. I think I’m a little hungry too.” Sara admitted but she wasn’t going to admit that she was feeling sore. Not yet anyways. Taking his hand as it helped her stand up on wobbly legs like a young doe.

Sara turned to the bed and chuckled at the sight. “This good girl desires new sheets, a massage and food. I’ll take that offered massage since it’s your fault I’m now this sore.” his wobbly bedmate told him as she couldn’t hide the chuckle she let escape. “I’m sure this won’t be the last time they’ll ge changing our sheets this evening.” she hinted at later activities.
 
“I’ll ask for extra sheets, then.” Nick’s tone was happy. He certainly seemed to feel that his money was well spent on his sugar baby.

He stopped the video and walked her to the bathroom, enjoying watching her wobble and knowing it was the result of their actions. Her orgasm had left him wanting to see more, to push her to cum over and over until she couldn’t any more.

But time enough for that later.

“Let me know what you want and I’ll have it delivered - if it isn’t available from the hotel restaurant, I’ll order out. In the meantime, why don’t you get started? I’ll take the sheets off of the bed for now, then I can get the door when the food arrives. If you’d like, we can get more wine, too.”
 
The video was completely forgotten as she would slowly make her way to the bathroom. “what do toy usually get? Don’t think of me as weird if I say I’d be happy with pizza and French fries. Ohh even Chinese food would be good. Wine?” Sara asked with a chuckle. “I won’t say no but are you trying to get me drunk?” she teased removing her cosplay and leaving it at the door. “I’d like wine but what about beer? I’m okay with beer or even cocktails. I’m more hungry tough so surprise me. I’m gonna get cleaned up. Join me when you finish.” she said getting ready for another hot bath.
 
The flood of words was flirty, but not particularly informative. He didn’t want to hurt his sexy idol’s feelings by guessing wrong. Still, he shrugged, she’d offered him two perfectly serviceable options. He was a bit surprised, though - he’d expected her to take full advantage of the offer and try to burn a hole in his wallet.

He went to the phone and ordered from the restaurant downstairs - he got a surf’n’turf, filet mignon and lobster, to share and a pizza with a side of fries. Despite her teasing concern, it wasn’t something he thought to be strange. Additionally, he asked for four bottles of whatever beer the server recommended. Not being a beer drinker himself, he decided not to run any major risks. Last, but far from least, he requested a new set of sheets as well as a spare.

Finally, he stripped the sheets off of the bed and left them on a pile outside of the door, hanging the “Do Not Disturb” sign from the handle. With that complete, he went to go join his new sugar baby.
 
Sara wasn’t picky and most sugar babies would’ve ordered the most expensive but she went with comfort food. For her she stuck with something simple that no place would mess up. She did have her expensive favorites but this hotel was new and she didn’t know if she’d like it.

Despite what she did on camera she was pretty down to earth. Simple foods and things made her happy. When he decided to join her she was already lounging in the bath but she added a mountain of pink bubbles. “So sugar daddy what did you get us?” she asked as she took the chance not to splash him but nope bubbles at him.
 
Nick eased into the water, groaning as the heat relaxed his muscles.

“Two dishes, both to share. I took your suggestion of a pizza with a side of fries; I went half cheese, half pepperoni, just to be safe. I also got us steak and lobster. It’s a surf’n’turf, usually just for one person, but with the pizza I hope it’ll be enough. I also got us four beers, but the guy at the desk is gonna surprise us with what kind.”

He slid over to her, putting a hand on her thigh. “I still owe you a massage, though. If you tell me where you’re sore, I’ll do my best for you.”
 
Giving Nick a happy nod but also a smile since he went fancy and classic. “Next time I’ll ask for fruits. Strawberries and pineapples and maybe bananas and chocolate. Maybe before they close the kitchen get whipped cream and flavored syrups just for fun.” Sara said as she scooted over to be closer to Nick with his hand on her wet thigh. “My shoulders could use a good rub.” she suggested before thinking about what to talk about. “Would it be rude to ask if I’m your first sugar baby or what number am I on your list when you asked me to be yours.”
 
Nick leaned his head back and laughed. He was no stranger to the insecurity of pretty girls, but it was always surprising to him. She was gorgeous - how could she not know she was the first on his list?

“I’ve never had a sugar baby before,” he confessed, “and you are the first girl I’ve ever asked.”

He grinned, motioning for her to turn so that he could massage her shoulders.

“Turn around or sit in my lap, I’ll start working on your shoulders. In a few minutes I’ll get up so that I can use my elbows and forearms.”

Nick decided to continue the conversation, taking it a different direction.

“My turn on questions! Since we’re getting personal: what’s a sex fantasy that you’ve never shared with anybody?”
 
“I was honestly expecting for you to say I was the seventh or eighth only fans girl you’ve asked.” Sara said as it took her a moment to turn around and get comfortable in the hot water.

She snickered when he asked her about a sexual fantasy that she never shared but instead of answering she decided to play coy and say “You have not unlocked that feature yet sir. If I just told you things where would the fun be in it? I’m going to make you work of you want that kind of information especially after I let you slide that sexy sword of yours in me without a swimsuit on. “ she snickered.
 
“Wooooow.” Nick drew the syllable out teasingly. He wasn’t upset by her answer. He’d even expected it.

“Alright, alright. I’ll pick an easier question: did you bring any toys in that magic bag of yours?”

He put his hands on her shoulders, grabbing the trapezius - the muscle at the top of her back, between the neck and arms - and began kneading it gently. He just squeezed it, pulled gently, and let go, working the muscle and warming it up for deeper massage.
 
“No. Just costumes. I was here for work not sex. I wasn’t expecting to be asked to be someone’s sugar baby or expecting to get laid today.” she was honest and really didn’t expect this to even happen!

“Mmm. That feels nice. My turn. Do you always tell your girls you want to cum in them. That’s fair game considering I let you.” she said leaned back into his massaging. “if toy answer maybe I’ll tell you something secret about myself if you are a good boy. Unless you want to play truth or dare once drinks get her.” Sara said giving him options.
 
Nick began using his thumbs to press into the muscle near the neck before sliding to the shoulders. He applied pressure from behind, lifting it slightly, rather than straight down. The strokes were broad, but a bit firmer than the compressions and squeezes he'd been doing earlier.

"Absolutely not. Usually we have a condom, or I'll pull out. You're just so sexy, though, and I thought you'd be a little turned on knowing how badly I wanted you." He paused to lean in, kissed her behind the ear, and continued. "Keep your secret, Princess, Truth or Dare sounds like a great game."

It would be a fun and natural progression back into sexual activities, and putting her at ease could only be good for him.
 
Sara let out a deep moan with how good his massage felt on her shoulders. She was so soft and her skin was silky smooth. As she was getting her massage she was not expecting Nick to answer her question but he did. When he said keep her secrets she let out the most adorable chuckle and leaned back into his rubbing. “Let’s Play then the question is who goes first maybe I’ll be nice and let you go first though I do have a feeling you seem like a dare guy.” she thought she figured him out especially since he was the one who mentioned cunming inside her. Figuring he picked out first seemed like something he do.
 
Her moan was nice - not quite the whimpers, squeaks, and gasps that she gave during sex, but definitely a genuine expression of appreciation. He repositioned his hands, moving to the shoulder blades. His fingers ran around her lats, while his thumbs ran through the muscle between the shoulder blades themselves and her spine. He moved his thumbs outwards, continuing to use broad, deep strokes to break down any tension that he found.

"I'll tell you what. For my first two turns, I won't use any Dares. You can give some to me, though..." He winked. "I'm sure I won't mind."
 
That moan of satisfaction and relaxation. Nick felt so good massaging her shoulders. Leaning back she let herself melt into him. Hearing his offer cost her to giggle cutely but not with agreement. “ do you really trust me with giving you dares?” Sara asked and she lied her head back and let her soft hair rub against his chest. “ The question now is who goes first. I can give you a few dares but I don’t want you to think badly of me if I do.” with the answer probably made Nick wonder what was on her mind.
 
Nick raised an eyebrow, not that she could see it. He kept his voice carefully level, but there was a hint of excitement. She'd been a perfectly submissive little sex kitten for most of the night, but now she was almost challenging him. It was a teasing, playful sort of pushback, not a genuine bid for control, and he decided he'd flex a little. It would be best, he decided, if he didn't cede too much in the way of leadership.

"I think I'll go first, since you have nothing to worry about."

Her position had made the massage difficult, so he transferred his hands to her upper arms. He alternated firm squeezes and gentle caresses, encouraging blood flow and loosening the muscles.

"Do you want to wait for the food to arrive, or should I ask you a question now? I think it was my turn, anyways."
 
He could not see that he raised an eyebrow but she was curious to his silence. Sara was not challenging him but she was being playful kitten toying with a mouse.

“ how about one question now before food and one after and then maybe you can massage my front side.” what did she mean by that possibly he got the touch her lovely supple breast but she wasn’t going to outright say that. She let next mind think and wonder what exactly she meant
 
"I suppose that's fair."

He took a second to marshal his thoughts.

"Have you- How did you feel about being filmed, especially with the footage we got?"

Nick had to catch himself - he'd almost asked if she'd ever done anything like that on camera before, but that wasn't really what he wanted to know. She was already talking about changing where he could massage, and he took a moment to use the bubbles to wash himself. His cock was already hard again, and it felt good to rub soap over it, to clean himself thoroughly. He felt like a fresh man, almost like the night had just started.
 
When he asked that question she had to be honest. “I don’t know. I’ve never been filmed like that before. It scares me honestly. That could bite me in the ass in the future. I’m usually the one who controls my photos and other images so as fun as it is on paper it scares me that you could possibly harm me with that in the future. Maybe we should make a contract for it.” as beautiful as sara was she was a smart woman who worried about the risks there. “My turn. Truth. Do you film all the woman you’ve been with?” she wanted to ask if yes did you keep the footage but she was holding off on that until later.
 
Nick smiled.

“Believe it or not, my beautiful princess, I actually picked that habit up from a woman. I have filmed some one nighters with women who consent to it, but I filmed you because I knew I’d want to remember the night and watch it every so often. You’re just too gorgeous to pass up.”

He stretched, snaking his arms around her midsection in a hug. The man gave her a little squeeze, leaning his head against hers happily.

“Alright, my question. Do you want to watch our videos once we’re done?”
 
His answer wasn’t creepy luckily but she still worried. Sex tapes could make or break a person. More like break a woman so she was always cautious. His question made her blush as he snaked his arms around her helping her lay back as she relaxed. “Maybe once. I’m used to myself in photos as you know maybe dance videos or tik tok but this…it’s new. I don’t know how I’ll react watching myself like that….” Sara spoke honestly but he knew she had shy tendencies.
 
Nick liked feeling her relax on his chest. He sighed happily, giving her another small squeeze while she answered. The blush was almost audible, but maybe it was because the man knew how shy she could be. It was so cute how she switched from eager sex doll to shy and innocent.

“I’ll tell you what, Princess. Why don’t you pick the part you watch? Which one would you want to see?” He tapped a finger on her stomach lightly. “You could see yourself on your back, or facing the camera, or getting a facial.”

His words were teasing and, even though his words were certainly bold, they weren’t pushy. She would be able to tell that he wanted it, but that he would recover from her saying no.
 
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