A Holiday Arrangement

2024 © Smuttyandfun All Rights Reserved

This one is for the Winter Holiday 2024 Contest.

Everyone in this story is over the age of eighteen.

And I hope you all have a wonderful holiday!

"You can do this," Alyssa kept chanting to herself. Determined to get it over with, she forced herself to keep walking until she found herself stepping into the bustling lobby of the luxurious Grande Essex Hotel.

She felt a little awestruck as she took it all in, it was just so beautiful. With the enormous glittering Christmas tree all lit up in the center of the lobby, pretty multicolored poinsettias scattered around the room, and adorable little toy elves peeking out from every corner.

Since she hadn't bothered to decorate her tiny apartment just for herself, she would have loved to have taken a moment to wander around to take a closer look and maybe get a few pictures. Even just of the tree with the shiny red model train circling around it, overflowing with miniature Christmas presents, with a tiny toy mouse in a red Santa hat waving from the caboose. She noticed all the children seemed to be enjoying it, the way their faces were lighting up as they watched it go around, all of them pointing and excitedly giggling as the mouse waved.

But of course, she knew what she doing, she was stalling. No matter what awaited her, she knew she had to get upstairs.

Drawing in a long deep breath, she walked over to the elevators and stepped inside the one that a smiling young man in a smart looking hotel uniform was holding open for her.

Once she got in, she was so nervous her hand was shaking as she reached out to push the button for the penthouse.

Not that she had any plans, since she lived alone, but it still felt strange to be doing something like this, especially on Christmas Eve. But with her being off school for the holidays, and the man she was about to meet having a few days off with his office closed till the new year, it was the only time they could arrange it.

When the door slid open on the top floor, she poked her head out, and cautiously looked up and down the long, plushily carpeted hallway. She was feeling so nervous about what was going to happen, she was almost tempted to chicken out and push the button to send the thing back to the ground floor.

But of course, her conscience took over, and she reminded herself again, that a promise was a promise, which meant she had no choice. She had to follow through with it and meet the man who was waiting for her.

And she really needed the money, considering her entire future was depending on it.

As she wandered down the hallway looking for his room, she told herself that people had sex every day. Considering how many billions of people there were in the world, she imagined there were probably at least a million of them going at it right now. And soon, if things went to plan, they would make it a million and two.

When she finally found his room, she stopped and stared at the door for a minute, trying to imagine what was going to happen once she stepped inside. But knowing she couldn't stand there forever, she got up the nerve to reach out and quietly knock, not even aware that she was holding her breath.

With no idea what he'd look like, she let out a little gasp when a tall, surprisingly handsome man wearing a hint of a smile, pulled open the door.

For a moment she just stood staring into his eyes, wondering what she should say. Though she decided it probably wasn't a good idea to start things off by blurting,

"Hi. I'm the virgin you asked for."

Deciding he had better get her out of the hallway, he pulled the door open wide, flashed her a welcoming smile and said, "Please, come in."

Taking a peek around him into the well-appointed living area, decorated with pretty groupings of bright red poinsettias, she was glad he had chosen a suite for their encounter, so at least she wouldn't have to deal with looking at the bed right away.

She could feel her palms sweating and her breasts beginning to tingle, as he stood in front of her, while she stared at him feeling a little breathless.

Which wasn't surprising, because he just looked so handsome and sophisticated, like a rich guy out of a movie, in his dark suit and tie, crisp white shirt and perfectly polished shoes, with a distinguished touch of gray at his temples. And considering how much he was willing to pay to be her first sexual encounter, she imagined he was probably doing

way

more than okay. Which she hoped meant that he'd keep up his end of the bargain and pay her what he'd promised.

"So, what's your name?" he asked, leading her into the sitting area.

Clearing her throat, she replied, "Um, Sapphire?" She had noticed a bright blue bottle of Sapphire gin when she'd walked past the bar downstairs, and thought it sounded kind of interesting and exotic.

With a sceptical arch of his eyebrow, he looked at her, with a hint of amusement lighting up his blue eyes. "Surely that can't be your real name." At least he hoped not, because it sounded like the perfect name for a stripper.

She winced and admitted, "No, it's not."

"Well, if it's okay with you, then I think I'll call you Ann. And you can call me John."

Glad that he seemed reasonable, she managed to muster a smile. "Okay, John."

"I haven't eaten yet, and I was just about to order some dinner, if you'd care to join me. I thought since it's Christmas Eve we should have something festive, like turkey, if that's okay with you."

"Um, sure, sounds good." No idea how this whole thing worked, she was surprised he was offering to feed her first. And turkey dinner sounded really good, since she'd mostly been surviving on noodles, just to save money on food.

With the hotel phone in hand, before he ordered, he looked at her and asked, "Anything you don't like, Ann?"

"No." She shook her head. "I'll eat almost anything."

He smiled, looking pleased. "Good."

As she listened to him talking to the kitchen, she thought it was kind of sweet that he offered to have dinner with her before they got down to business. Especially considering what she was here for -- and it sure as heck wasn't to make small talk or share a meal.

Once he'd hung up the phone, he let his gaze slide over her. And she thought he seemed to like what he was seeing, judging from the way he was smiling, even giving her a flash of his dimples. Before he broke into her thoughts and said, "So, tell me a little about yourself, Ann."

Not sure how much she should share, since it wasn't exactly a date, just an arrangement that they'd agreed upon after connecting online, she decided she might as well be honest. "Right now, I'm in medical school, and I'm hoping to specialize in oncology, since I lost my mother to cancer."

"I'm sorry to hear that."

Just thinking of her mom had her struggling to keep the emotion out of her voice, as she took a breath and continued. "Being an accountant, she'd planned ahead and left more than enough for my education. But unfortunately my step-father took every cent, sold the house and left me with almost nothing." She looked into his eyes, hoping he could understand her motivation. "Which is why I'm here with you, so that I can finish school."

He didn't say anything at first, just nodded, like he was mulling it over. Then he met her gaze. "You know you could take him to court to try and get your inheritance back."

Though he knew he could offer to help her, he wasn't too sure if he should get involved, considering what he had going on in his own life.

"Well, unfortunately lawyers cost money. Which is something I don't have a lot of right now. Or I wouldn't be here," she admitted with a shrug.

"No, I guess not."

There was a rap on the door, ending their conversation when he got up to let the server bring in their dinner.

After he'd tipped him, John came back and set down their plates. Then he pulled out his cell phone and put on a song from his play list, and smiled across the table at her. "Thought we could enjoy a little music with our dinner."

"Oh, this is nice," she said. "Who is it?"

"Marvin Gaye."

She smirked when Marvin's mellow voice rang out,

"And when I get that feelin'

I want sexual healin'"

For a moment they coyly smiled at each other, listening to the sultry lyrics, while they enjoyed a perfect Christmas dinner of roast turkey, mashed potatoes, stuffing, cranberry sauce, and tender crisp veggies with a very tasty gravy.

While she was wondering if the song was his way of letting her know that this was more than just a tryst for him, and might be something he felt he actually needed.

Still, she thought it was sweet that he was going out of his way to help her relax, when he got up and poured them both some chilled white wine to go with their dinner. While also taking a moment to breathe her in, she noticed, when he hovered over her hair, inhaling the floral scent of her shampoo, making her smile.

After they'd finished their dinner with all the fixings, along with a decadent selection of Christmas cookies and chocolate dipped strawberries with whipped cream for dessert, he sat back twirling his wine glass in his hand, studying her.

"You're very pretty," he remarked, enjoying the way she blushed. "I've always had a thing for redheads, though I think blondes are quite sexy, too. And you've got the most amazing color of hair I've ever seen."

"I'm a strawberry blonde, so I'm not quite a redhead and not exactly blonde."

"Well, I think you're very attractive. And I love the little dusting of freckles on your cheeks, too." She was the perfect mix of sexy and sweet, which was exactly what he was hoping for.

If he was only going to do this once, he wanted to be with someone sweet and innocent, who hadn't yet been jaded by life. He'd had his fill of hard-nosed professional women, who often dictated what they wanted in bed. So, finding someone like her was pretty refreshing.

After what he'd said, he laughed at the way she rolled her eyes, since he knew most women didn't think much of having freckles. Though he wondered where else she might have them, since he already knew he'd love to trace them with his tongue.

For a while they sat and talked about all different kinds of things, which both of them seemed to enjoy, especially once he got her laughing.

"You've uh... got a dab of whipped cream on the end of your nose, John," she said, touching the ends of hers, so he'd know where it was.

He picked up the napkin, wiped it off, and pointed at her. "And it looks like you've got a touch on your bottom lip."

Lashing out her tongue, she kept licking around her lips, till she noticed the gleam in his eye, and realized he was joking.

"You're a real tease, aren't you?" she said, chuckling.

"I admit, I love to laugh. And it's nice to see you laughing, too."

She reached for her wine, glad now that they'd shared dinner. And, as his eyes met hers, she noticed they seemed to grow darker, the longer they stared.

Until a loud crack of thunder booming overhead, had them flinching and turning their attention to the rain pelting against the windows.

"Sounds like it's really starting to storm out there. Did you drive here, Ann?"

"No, I took the bus. Unfortunately, I had to sell my car so I could pay my rent."

"Aw, that's too bad. But don't worry, I'll send you home in a cab, so you won't get stuck in the rain. It's supposed to get really cold later, and change to snow, so you'll be better off not having to walk from the bus."

"Thank you," she said, smiling into his eyes, realizing that he was actually a pretty nice guy, despite the fact he'd basically hired her for sex. Which she was still having a hard time wrapping her head around, since she'd never done anything so crazy.

He'd gotten her so relaxed and they'd gotten so comfortable with each other that she'd almost forgotten why she was there. Until he reminded her when he jolted her back to reality when he said, "I'm sure you've been wondering why I was looking for a virgin."

Wincing a little, she nodded. "Yeah, I was curious."

"I should probably mention that I've never done anything like this before. But circumstances being what they are, I decided that I'd love to experience a few things that I've never had the pleasure of enjoying. Being with a woman who has never been intimate with anyone else, would be a first for me. I've also never had sex without protection. And I would really love to come inside you, just to know what it would feel like to be skin to skin when I climax, even if it's only this once."

While she was trying to absorb what he was saying, he pulled a card out of his pocket and pushed it across the table. "As you can see from the testing I've had done, I'm clean." He raised an eyebrow. "And I'm assuming that you're using birth control, and there's no risk of you getting pregnant?"

She quickly nodded. "I'm on the patch. And the doctor said it's about 99% effective, so I'm protected."

"Good." He broke into a smile. "Though I have to confess, I've always fantasized about getting a woman pregnant. Which is another reason I'd like to take you bareback, so I can still imagine that it could happen."

"Oh, okay," she said, not sure what else to say, once he'd laid it all out like that.

Noticing she looked a little uncertain, he gave her an encouraging smile. "Hey, don't look so scared. You don't have to worry. I'm not into anything overly kinky, and I'm not planning on tying you up or anything like that. I just hoped you'd be okay with acting out these few little fantasies with me. It's sort of a bucket list of things I'd always wanted to try, but never had the opportunity to explore."

"So, you're not married?"

"No." He shook his head, heaving a sigh. "I've just never met the right woman. And to be honest, until lately, I've always worked too many hours to keep a relationship alive. Which is one of the reasons I wanted to do this, since I may never get another chance."

She studied him for a moment wondering why he'd say that. "Well, you can't be that old. And I'm sure you could still meet someone. I mean, you're a good-looking man, and you obviously keep yourself in shape. And you're kind of fun too," she said with a grin.

Though flattered, he thought he should be honest with her. "Well, I just turned fifty last month. Which I'm guessing probably makes me about twice your age. And since I've just passed the half-century mark, I've decided I might be a little too old to think about setting up house with anyone anymore."

Now that she knew where he was coming from, she felt kind of sorry for him. He might be wealthy and successful, but if he was living his life alone, having given up on the idea of ever finding a mate, she could sort of understand why he'd want to act out these last few fantasies that he'd never got a chance to experience.

When he stood, picked up his phone and put on another song, she smiled at the familiar sound of Nat King Cole's sultry baritone filling the air with the classic Christmas lyrics, "Chestnuts roasting on an open fire..."

But the spell was quickly broken when he pointed toward the other room, and said, "Well, I guess we should retire to the bedroom."

Her legs felt a little shaky, but once she got to her feet, determined to go through with it, she put one foot in front of the other and led the way into the other room. The room with the bed.

Though he managed to put her at ease when she felt him coming up behind her, gently stroking a hand across her back and pressing a kiss to the top of her head.

He was being so gentle and careful with her, that she realized she could have wound up with someone terrible who would probably already have had his way with her by now. And more than likely, none too gently.

There would have been no dinner, no conversation, just slam bam, thank you, ma'am. Then he would have shown her the door.

At least he was kind and being sensitive about what she was surrendering, even if it was a rather strange transaction.

Then he surprised her when he gently took hold of her shoulders, turned her around, and heaved a heavy sigh as he gazed into her big innocent green eyes. "As much as I want to, I don't know if I can do this. So, if you want to back out, I'll understand. And don't worry, I'll still pay you what we agreed to. So, if you want to leave, you're free to go."

"Wait, what?" She couldn't understand what had happened to make him change his mind.

"Ann, I'm trying to tell you that you don't have to do this, if you don't want to. And you'll still get your money."

"But that's not fair to you. I mean, I'm nervous, because obviously I've never done anything like this before. But I was always taught that a promise is a promise. So, I think we should get our clothes off, get in bed and, you know..."

He smiled, surprised that he was giving her an out, and she wasn't flying out the door, racing for the elevator. Instead, she was telling him that she was willing to follow through with it, and do what she had promised. Softly touching his lips to forehead, he murmured, "You know, you're very sweet. And you have no idea what this means to me."

"Actually, I think I do." Smiling into his eyes, she surprised him when she pushed up on her toes, circled her arms around his neck, touched her lips to his, and kissed him.

Groaning, he wrapped her in his arms. And for a moment he lost himself, savoring the feel of her warm soft lips, as he slipped his tongue inside and revelled in the delectable sensation of exploring the depths of her sexy mouth.

Just sharing a kiss was getting him so hard, he could hardly wait to discover how incredible it would feel to actually lose himself in her sweet little body.

Still, just to be sure, he pulled back, cradled her face in his hands, and asked one last time, "So, you're sure about this?"

"Yes." She smiled. "I am."

Considering how charming he was, and how much fun he was to be with, she decided that she actually liked the idea that he would be her first. Especially since he'd been so kind and careful with her, when she knew he didn't have to be.

Still trying to try wrap her head around what she was about to do, she reminded herself that she knew lots of girls who slept around, and didn't think anything of having a one-night stand. And obviously this wouldn't be much different.

Except for the fact that he was paying her for the privilege, by helping her stay in school.

She quivered as the most arousing little shiver raced up her spine when he slid her dress up over her back and softly groaned at the feel of squeezing her backside in his hands as he kneaded her tingling flesh.

"Should I be taking off my clothes?" she asked, already feeling a little breathless.

Smiling into her eyes, he shook his head. "No. I would love to have the pleasure of stripping you bare."

"And should I be doing the same for you?"

"If you'd like to, sure."

Curious to know what he'd look like out of his clothes, she grinned, and reached up and started loosening his tie.

She noticed his eyes had turned to a very dark shade of blue and his breathing was getting kind of choppy, as she unbuttoned his shirt and let her fingers trail down over his slightly furry chest and his nice firm abs, before daring to unfasten his belt and unbutton his pants.

When she went to pull down his zipper, he put his hand over hers and looked into her eyes. "Ann, before we go any further, I really want to thank you for doing this, for finding the courage to come here tonight and share yourself with me. And I want you to know that I'll never forget this night we've spent together."

Pressing a kiss to his chest, she whispered, "Neither will I."

Once she'd pushed his pants down around his ankles, her eyes popped at the sight of him in his tighty-whities when she saw the huge erection bulging across the fabric, with the tip already so wet it was soaking right through.