Chapter 1

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Mult, Consensual, Romantic, BiSexual, Heterosexual, Fiction, Spanking, Anal Sex, Masturbation, .

Desc: Sex Story: Chapter 1 - This is a semi-autobiographical telling of the daydreams I have of winning the Lottery. Names have been changed, but if you know who I am in the real world, you'll know who I speak of. Places are actually places in Salt Lake City. As I said, these are my daydreams.

Nick sat back and contemplated the changes in his life. He was 46 years old, and was three weeks short of an anniversary. Almost a year ago, he'd been working in a small grocery just west of Salt Lake City. The pay hadn't been bad, but then, he'd been with this family business for twenty-five years. But there was no hope of advancement, just another thirty years of boredom and idiots to look forward to.

Then his life changed, with a huge Powerball payout. Everyone told him "Take the lump sum, man! Think of all you can do with it!"

But he'd often dreamed about what he'd do if the Goddess smiled on him that way, and a lump payment wasn't in his plans. He didn't plan to take the money and screw up his life. With yearly payments, if he fucked up, the next year he would straighten it out. Nope, for the next 30 years, his finances were secure. Even at his greediest, he didn't think he could spend $2,000,000 (post-IRS) in a year more than once or twice. He'd even given his employer thirty days notice. Those had been a loonngg thirty days!

This last year, he did come close to spending it all. First, he'd taken over his family's mortgages, one on his parent's condo, another one in the same area for his younger sister, then the houses of his older sister and his younger brother.

For himself, he'd signed a one-year lease on a nice 4-bedroom place, with an option to buy at the end of the lease. Because he didn't know where he really wanted to make his home yet, the lease was a good choice. He knew he wanted big water, and a small yacht, or a nice fishing boat, something ocean-worthy, but that one man could handle without too much difficulty. Maybe Washington, Oregon, maybe Northern Cali. Or maybe New England. Hell, maybe Hawaii!

Next came seven new cars, two SUVs, and a pickup truck. His family was definitely sharing his good fortune. After that, he'd taken some time to travel. New York, Pennsylvania, Virginia. Met good friends he knew only from the Internet. Spent days with two of them, and learned cyber- and phone- sex had just whetted their appetites. Then Washington and California, meeting more friends. Down to Texas, enjoying the company of the Grove, and spending some time in touch with the Goddess.

He loved to fly. It occurred to him on the way home from Texas, as he watched a flight attendant try to deal with more stupid people, he had the money to actually do something more than sit and watch. He'd learn to fly, maybe get his brother Carl and his nephew Luke to learn too. He was sure there would be times a co-pilot would be needed, why not someone he liked a lot?

But now, he needed to do something about his social skills. True, he'd seduced two women he'd never physically met before, but he'd been interacting virtually for a year with Dani, and probably seven years with Lily. They couldn't be considered new acquaintances. He needed help with face-to-face social events. Ok, he admitted to himself, he needed help with dating.

He'd never considered himself to be good looking, although once in a while he could see a trace of something a woman might find attractive. Usually if he took off his glasses and stepped back from the mirror enough that his face was blurred. He was 5' 9", and 272 pounds. His hair was a medium brown, with a good scattering of gray, especially around the temples. But it was nice and full, and the gray, hell, he figured he'd earned it all.

Then another thought struck him, something he'd read in a Yahoo forum a few years ago. Someone had been discussing the advantages of escorts over prostitutes, if he remembered right. Something about escorts in the role of teacher, not necessarily in sex, but in social interaction. True, the point of the discussion had been about young men, just beginning adulthood. But it might work for an old dude. Maybe someone to take to the Symphony, the ballet, charity fundraisers. Maybe someone to teach him how NOT to dance like a spastic elephant. He laughed at himself, 'Yeah, like that was possible'.

He thought some more, then called his bank to double check his balances. Next deposit was scheduled for twenty-one days from now. One of the first things he'd done, before even flying to Boise to collect his winnings, was open two more checking accounts. The first one was for expenses, such as home purchases and rent, and new car purchases. The second was for charity. He'd decided that after family was taken care of, he'd help others who needed it. But he only gave to recognized, organized charities. Oh, and he contributed to the Democrats.

He laughed to himself when he remembered, less than a week after turning in the winning ticket, the Bishop and Stake President of the area he lived in had shown up at his door, encouraging him to do the 'right thing' and pay his full tithe. Nick had tried to be polite, but it was hard, and he'd asked why he should begin such a practice when he hadn't been to church in 29 years? Nah, he figured the LDS church had plenty of available cash. He did contribute heavily to Catholic charities, though. Maybe he was being spiteful? He didn't care.

The third account was his 'Do as I will' account. He'd decided to budget himself $10,000 a week. He bought food, toys (his new computer and home furnishings) and what he thought of as 'fun'; movies, music, books and travel. He'd also used the leftovers from each week's budget to purchase nearly $100,000 worth of stocks, bonds and mutual funds. Right now, the balance of the three accounts still totaled $158,000. More than enough to start a makeover.

He needed to get into shape. His old job had kept him moving probably 40 of the 48 hours he was scheduled, and probably kept him from getting even bigger than he was. Time to join a gym, and maybe Weight-Watchers again. Then he looked in the newspaper classifieds. Yup, under "Entertainment", escort services competed with phone-sex lines and exotic dancers.

He made a few phone calls and sat back with a sigh, dissatisfied. That was a bust. All they had really offered were prostitutes. He already had two very nice young women that he visited regularly, and he'd been flying to one of the Nevada brothels every couple of months. No, sex wasn't what he was looking for in this case. Then he thought about it some more. Did he know anyone who might have used such a service? Nope. Hmm, maybe Carl would. His brother Carl was a mortgage banker, and his company did a fair amount of business with out of town clients. But did he want to involve his brother? He considered this for a moment.

He was single, and didn't have to answer to anyone. His parents were cool, as were his siblings; and he wasn't going to go out of his way to embarrass them. He wasn't a public figure, per se, and didn't really give a damn about anyone's opinion besides his immediate family. He picked up the phone and called Carl's cell phone.

"Hey Carl, what's up?"

"Hey Nick, not much, Steve has a cold and is making Gina nuts. You know how she reacts to every whine and whimper."

Gina was Carl's significant other, and Steven was their four-year-old son. Nick adored both of them. "Carl, got a weird question for you. Do you know anything about Escort services? Not prostitutes or dancers or whatever, but that actually provide women to attend social occasions?"

A short silence followed the question, and Nick thought he might have offended his brother.

"Umm, sorry, you're right, definitely a weird question. Ok, can I ask you some questions, without twisting your shorts? I assume you want someone attractive, but probably fairly sharp and well read. No bubbleheads, right?"

"You said you weren't looking for prostitutes, but I suspect you'd be willing to 'negotiate' for special services, if she appealed strongly to you. I mean, if you just wanted to get laid, I know you, you'd have asked me for that. Never mind, I've noticed your little trips to Vegas. Nuff said."

"No comment," Nick answered, but Carl heard amused confirmation in his older brother's tone.

"Alright, tell me what you are looking for: Companionship, obviously. What else?"

"I want someone to increase my social skills. Teach me to dance, what to wear. You've seen my wardrobe; tee shirts and jeans, with a pair of sneakers. Some one that I could date, you know, 'Dinner and a movie', the Symphony, a concert, hell, maybe the ballet. Someone to take me clubbing, after she teaches me to dance. She'd have to have an eclectic taste in music, though. You know my radio's always set on 107.5. I like classical though too. Hell, I like trance and electronica! With the right girl, I'd even try line-dancing. Oh, and she can't be a vegetarian or major health-food freak. I'll be damned if I can't spend my money on good food. Hmm, maybe she could teach me to be a better cook, too. Oh, and moderate to liberal in politics," remembering the invitation he'd received to a Democratic fund-raiser coming up in about six weeks.

Carl's laughter filled the phone. "Ok, does this have to be all rolled into one girl?"

Nick thought about that. "Actually, no. I don't mind having a dozen women seeking my company." Carl laughed out loud at that. "Have some thoughts?"

"A couple, actually. Let me make some calls. Oh, when's the next flight class?"

"Saturday at 11:30. I'll pick you and Luke up in the morning. You know, the more research I do though, the more I think we should take the jet course too. Some of the older jets are cheaper than a big turbo-prop."

"Well, if you didn't want to seat twenty people..." Carl chuckled.

"Yeah, and who do I leave home? Gina and Luke's girlfriend? Yeah, that would make me damn popular!" The fact was, even without Luke and his sister Sarah's dates, there were still ten bodies in his immediate family. And he kind of liked the thought of flying everyone to new and different places.

"Yeah, yeah, you just know if you don't terrorize us all together, you'll never get the next victims. Anyway, I'll check on this, ask around, and let you know as soon as I can. See you Saturday!"

"Ciao bro, kiss Gina and Steve for me!"

Friday morning, he went down to the garage and climbed into his dark green 2004 Jaguar. It was one of the most expensive car he'd ever owned, and was more fun to drive than any of the cars he'd test-driven, with the exception of the Audi convertible parked beside it. If the weather had cooperated, though, he'd have taken the Audi.

He popped his iPod into the deck and drove downtown to the appointment his brother had arranged. As he pulled up to the entryway of the Hilton, a valet dashed up to open the door. Collecting the player, he told the young man, "I'll only be a couple of hours. Don't go too far with it." He laughed at the man's expression. Here was a brand new, $60,000 car, being driven by a guy in worn jeans, a sloppy tee, and sneakers that were hardly new.

He took the elevator to the 8th floor, and knocked on the door to the room Carl had given him.

Another young man opened the door. "Are you a policeman, or a member of any law enforcement agency?" he asked immediately. Nick shook his head no. "May I see your ID, please?" Nick opened his wallet and pulled out his driver's license and state ID card. The young man studied them for a moment, then handed them back. "Thank you, sir." He held his hand low, and Nick slid a standard sized envelope into it. "Please come in."

As Nick stepped in, the young man stepped out and shut the door behind him. Nick looked around the nicely appointed suite, noting the closed door to his left. Within a minute of the door to the suite closing, he heard a phone ring behind the closed door, and not 20 seconds later the door opened. He was actually glad of their caution. It reassured him that he was dealing with intelligent folk. But the woman that stepped through the door took him by surprise.

She was about his age, mid 40's. She moved with grace and poise, her shoulder length red hair framing a very fine face. Her eyes were a green that he almost suspected were contacts, if the scattering of freckles across her cheeks hadn't indicated her hair color was probably natural. She was also quite short. The top of her head barely reached the bottom of his sternum when she stopped before him and offered her hand. "How do you do, Nick. I'm Cyan"

Nick took the proffered hand and bowed slightly to this enchanting creature. "Charmed, Cyan. Shall we sit?"

Cyan gave a delightful smile and bounced easily onto the couch like a little girl, then turned to face him when he sat, as she'd indicated, at the other end. She wore a loose ankle length skirt of brilliant blue, and a simple white blouse, and sat with one ankle tucked underneath her.

"You know, you aren't like most of my clients," she began. "Usually, when someone contacts me, they have a simple request. A certain type of woman, for a specific purpose. Fairly straightforward. And I don't think I've ever had as many pre-contacts before I spoke to the client. But with you, I heard from a very good client, asking if I was interested in what might be a major project. I was intrigued, especially when he couldn't offer more details, but was very firm in his assertion it wasn't some game. Then another client, asking if I was willing to speak with a friend about this same project."

"Then your brother Carl. I think it shocked him to his toes to find out whom he was speaking to. We've known each other for years; he's helped me purchase three homes so far. He told me about you and your, shall we say, 'windfall'. I'm going to assume you're serious; I know you can get laid for a lot less than you'll pay my ladies. Normally our fee begins at three hundred dollars an hour, but I see a great deal of potential, so the fee will be semi-negotiable. You'll pre-pay a rate of 200 hundred dollars per hour, with payment based on the expected length of the occasion. The ladies will bill you with a discreet note for additional amounts, depending on their requirements and choice. Agreed?"

Nick thought about it. It wasn't what he'd expected, but then he hadn't been sure what to expect, either. "I agree, Cyan."

"Good!" She hopped off the couch and took his hand, pulling to his feet. "One of the reasons I chose to meet here is that we are within walking distance of some very good clothing stores. I'm going to be your fashionista." She grinned and looked him up and down. "You do need some serious help!" With that, she put his arm around her shoulder and led him on the 'Quest to Make Nick Fashionable!'

Personally, Nick was surprised at how much fashion sense he actually possessed. Cyan would take him into a store, where heads would turn to look at the mismatched pair, the very short, sleek redhead and the taller, much heavier man. Then she'd tell him to go pick out a half-dozen outfits. "Don't worry about size. I know people who can make anything that you like, look good on you. We're looking for your personal taste here, what you think looks good."

When they'd finished in the sixth store, she told him, "Ok, I can see some of your previous problem. Your choices are good. But without some adjustments, most of them wouldn't work for you. But that's easy to work out. Carl tells me you're looking for a health club to join. Is that right?"

He nodded, and told her of his wandering from gym to spa, and frustration that the people he'd spoken to had presented a façade of support that he suspected would disappear as soon as he signed a contract.

"You're mostly right. So here, go to this club," she handed him a card for one of the health clubs he'd visited, with a woman's name and a photo of an attractive brunette with her hair in a functional ponytail. "Tell Connie Cyan sent you. She'll help you put together a real program to get in shape, and be there to encourage you. She's not one to abandon someone willing to work. She'll also be your companion occasionally, if you continue to use our service."

"Now, lets go get you groomed. You'll be amazed what the right haircut will do for you." She turned him to study his face, then reached up and lightly squeezed his left ear lobe, feeling the scar inside it. "I thought I saw a pierce mark there. Do you have a problem re-doing it?"

"Not at all. I did it the first time while I was in New Orleans, sort of a memorial for a great time. I wasn't ready for a tattoo, and didn't have the time for the ones I think about.

"Ok. I'll go pick out something for your ear. Do you prefer gemstones or dangles?"

Nick grinned. "Find me a nice dark red ruby. Maybe it's time to resurrect my inner vampire."

Cyan looked at him curiously, then nodded. "Any plans for tonight?"

"No. Probably curl up with a good book."

"Come back to the hotel tonight before 10. I'll have something ready for you to wear. Bring eight hundred for your escort, and plan to spend the night wandering clubs, so bring another hundred or so for drinks and cover charges. Lydia will make you dance, so be ready. But I promise, you will have a good time, even if you don't drink."

Nick looked at her in surprise. "Carl told me, when I was asking him about your likes and dislikes. One of the reasons I didn't offer you a drink back in the room, I didn't have any bottled water or soda. And Lydia doesn't smoke either, so she'll be avoiding the clubs that tend to get smoky. You'll have fun!"

He'd nodded, a bit surprised. And was very surprised again when he looked in the mirror at his new simple, no maintenance cut. 'OK, Cyan was right, this does look good.'

"Hold still a sec," He was surprised when Cyan took his ear in her hands. "Let's see if I can get this in without hurting you, or if we'll need to go get you re-pierced."

His ear stung for a moment, then he felt her twisting the back onto the stud she'd installed. "Perfect," she said with satisfaction. It did look good; the stone was almost blood red, about a half carat in size.

They walked back to the Hilton, and she squeezed his hand. "Now, go home, get a nap, and have a high protein dinner. You're gonna get some exercise tonight!"

The same valet brought around the Jag. "A little more than two hours," he laughed as he took the tip Nick gave him. Nick glanced down at the dashboard clock, and realized he'd been with Cyan nearly five hours. 'Hope she doesn't charge a bonus rate for extended hours.' Then he realized he held a piece of paper. It was a bill for an additional 300, written on the back of the receipt for the stud, and asking him to include it with Lydia's fee. Honestly, he'd be more than happy to pay it.

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