Side Bet Bluff Ch. 02

Part II -- Late Saturday Night (Jan 17)

The cold of the night's air was quite a shock exiting Aaron's condo.

"Wait, wait," called Hannah, who came running out the door. "Your coat!" And she hurried over to Jaycee with a purple coat outstretched in front of her.

Jaycee, who had been squeezing her arms around her naked self and had already started shivering, looked over to me. I nodded and she quickly shoved her arms in and zipped up. The jacket was long enough to cover the upper half of her ass, barely hiding all the naughty bits.

Just then Tim came out of the house. "Aw, man!" he complained at seeing the covered Jaycee.

Jaycee turned to me and said, "Hannah rode over with me" and nodded towards her old, beat up, rusting red pick-up truck. The damn thing looked like it could fall apart any minute.

"Fine. Give her your keys. You won't need them until tomorrow at the earliest."

"Oh no," said Hannah, who suddenly clutched Jaycee's arm. "She can drop me off at our place first. She shouldn't be without a way to leave you if she wants."

What bullshit. Undoubtedly this was their plan to get Jaycee away from me, whereupon Jaycee would back out of the deal.

"The clock has already started," I declared. "So she has to do what I say. Jaycee, give Hannah your keys, and get your pretty little behind into the passenger seat of my car. Either that, or me and Tim will forcibly put you into my trunk."

"I like that second option," said Tim. "Let's go with that."

Jaycee held her keys out to Hannah. Hannah was surprised ... then she looked pissed.

"Fine," spat Hannah. "Take the little strumpet. She's not welcome in my home any more anyway." And with that she grabbed the keys out of Jaycee's hand and stormed off to the truck.

"Dude," added Tim. "How did you put up with that bitch for all those years. She kicked the crap out of my leg earlier."

Hmm. Maybe that's where my wanting women to remove their shoes came from.

"Even if she showed up in my bed naked I'd kick her out," Tim continued. "And yet you willingly fucked that bitch for how many years?"

"Goodnight Tim. Thanks for your money," I called out as I walked towards my sedan.

"Not my money, I came out even," Tim said, looking at Jaycee's bouncing bottom as she rushed to the other side of the car, hurrying to get out of the cold. Apparently he'd forgotten about his hundred dollar re-buy that was sitting comfortably in my wallet.

Very shortly Jaycee and I were seated, belted, and on our way to my apartment building downtown. I turned the car seat heater on to warm Jaycee's derriere, and she gave me a small smile.

"Well, now that you've got me, what are you going to do with me?" asked Jaycee.

"What am I not going to do with you," I laughed.

I was silent a moment, and unfortunately had a bout with my conscience. I had been playing the asshole inside the apartment, but that wasn't the real me in any way, shape, or form.

"Ok, now that you brought it up, I need to tell you that of course slavery is illegal, and that if you are going to do whatever I say, it will be purely voluntary. Even my punishing you, if I ever do, is done with your consent, and that you can walk away at any time."

And here's where she tells me to just drive her back to her place.

"How can I walk away when you said you'd ignore whenever I told you 'no'?" she asked.

"That's a good point."

After a moment's silence, Jaycee said "I should thank you for telling me that. I mean, I know you're a good guy and would never really hurt me."

"Right," I answered.

"Though," Jaycee continued, "you really have a killer instinct. I guess it makes sense considering your job and all, but I've never even seen that side of you before, let alone been on the receiving end of it."

We were silent for a bit. I wasn't sure what to say at this point.

"Umm ...," Jaycee stammered. "When you take my ass, I might freak out. You know that about me, right? I mean, I've been thinking about it lately, kinda. Just thinking about what it would be like, you know? And yet when you try I might just flip out and start hitting and kicking you or something."

"You're serious," I said in amazement.

"Of course I'm ... you didn't think I was? Then what the fuck am I doing here buck naked in your car, Billy?"

"Sorry. I guess I thought that when push came to shove, you would flip out and run from my apartment at something approaching the speed of light."

"Well, the thought had crossed my mind," admitted Jaycee. "But we made an agreement, and I don't go back on my word. Besides, I decided a while ago that if I was ever going to do something really kinky and naughty it would be with you. I trust you, and like I said, I know you wouldn't do anything to hurt me."

She really was serious. It took me a bit to let that sink in. I had been so sure she was bluffing just to get me out of the room. Now it looked like I was going to have Jaycee at my beck and call for a whole week. Oh, the possibilities.

"While I appreciate you saying that, and believe me I think that's one heck of a compliment," I replied. "I also see it as a potential problem, because if we do this then I do want to start with some ground rules, and I want to be able to punish you if you don't follow them. Otherwise, we're missing the point of this entire role-play."

"Then don't worry about it," Jaycee said. "I'll try to follow your rules and will submit to any punishment you think is appropriate."

"Even if you ..."

"I trust you," she interrupted.

Huh. That's a hell of a lot of trust. A lot more than Hannah ever gave me, that's for sure. Ain't that a kick in the head.

"Well then," I said with my demeanor changing. "You will follow these rules or you will be punished." I tried to give her my best serious face.

"Rule number one, you will not call me 'Bill', or 'Billy', or 'Willie', or 'B.J.'."

These were her nicknames for me that she used to tease me. Check that, more like belittle me.

"You can only call me 'Will', or 'William' or 'Sir'. I liked it when you called me 'Sir'."

"When did I do that?" she asked.

"When you presented me with your clothes, which I may never let you wear in my sight ever again."

"Rule number two," I continued, "and you should really like this one, I want you to have as many orgasms as you can with me. Do not hold back."

"Oh really?"

"Not that you would ever fake one, but don't. I want you to have as many real orgasms as you can."

"I'll give it my best shot," she smiled. "So, you're going to punish me if you catch me faking an orgasm?"

"Absolutely. That has to be one of the biggest insults to a man's ego ever devised. Alright, rule number three is I want to be able to give you those wonderful orgasms. So even though you have to do what I tell you, you also have to tell me what is working and what isn't. Just don't give me orders. But ask nicely and there's a good chance I'll give it to you."

"I'm not sure what I was expecting, but this wasn't it," Jaycee said, "I guess I shouldn't be too surprised. You've always been a sweetie. There's a reason I said I trusted you."

I arched my eyebrow at her. "Don't read too much into it. I'm still doing it for my own benefit. I was stuck doing the same things with no variation for so many years that I've forgotten how to be a good lover. You're going to have to tell me what you like a lot."

"Also," I added, "Just because you ask me to do something doesn't mean I'm actually going to do it. If I want X and you want Y, I'm still going to do X."

"Yes, sir. Of course, sir."

"Hmmm. Sarcasm may be as punishable as outright rejection of an order. Depending on my mood, of course."

"Oh, of course," her smirk now plastered on her face.

"Actually, I'm going to expand that tell me order to a 'you have to be truthful about everything I ask' order."

Jaycee stopped smiling.

"That sounds dangerous," she said.

"Maybe so, but let's make that official regardless," I ordered. "So tell me, why did Hannah say you weren't welcome at her place any more?"

Jaycee grimaced. "Oh that. Well, I'd rather not say."

"You tell me that right after I order you to be honest? Spread your legs."

"What?" Jaycee asked, confused at the sudden change in topic.

"You heard me. Besides, I think the seat warmer has worked long enough to make this a pleasant experience for me."

Jaycee spread her legs wide just as we came up to a red stoplight. I leaned over and squeezed my hand down between the seat and her crotch. Jaycee actually scooted forward and lifted her hips slightly to help with access. That was awfully nice of her. I stroked her pussy lips from bottom to top several times, feeling her sparse hair on my knuckles and collecting a small amount of moisture on my finger tips. I could see the stoplight cycle was scrolling through rather quickly so I dipped my middle finger just inside of her and then returned to my normal driving position.

"So again, what did Hannah mean by what she said?"

"If that was supposed to be my punishment for not telling you," said Jaycee, "then I'm never going to tell you anything."

Grinning, I replied "no, that was a small taste of how nice we can make tonight, but only if you're nice to me. So come on. Spill it. And this is your last warning for the entire week. I really don't want to have an argument with you every time I ask you to do something or answer a question. Every other time you don't do immediately as I say, I'll turn your cute bottom red with my hand."

Jaycee paused for a few seconds and then opened up. "I'm behind on the rent, like, a lot."

"Don't say 'like'," I said reflexively.

Jaycee sighed. "Ok. I'm behind on rent. I owe Hannah over a thousand bucks."

I whistled in appreciation of the amount. "So what were you doing betting, and losing, three hundred and fifty dollars tonight?" I asked.

"Trying to sucker you guys out of my rent money, that's what," she answered.

"Yeah, that blew up in your face."

Jaycee nodded. "I got really cocky. I wanted to start in a huge hole, try to get one of you guys to have the biggest pile, then I'd get both Hannah's and Susan's pots, challenge you to an all or nothing bet, and walk away with everything. ... Oops."

A light bulb went on in my head. "That wasn't your money you lost tonight."

Jaycee hung her head, still with her legs spread on the seat. "No. I convinced Susan to spot our stake. Hannah wasn't having any of it. She was furious I wanted to borrow more money from her when I already owed her so much. Susan's been wanting to move out of her parents' house, and Hannah is done with having me as a roommate. So I'm having to move out anyway."

"With Susan taking your place," I added.

"Right. I could have probably still camped out on the couch for a week or two. At least I could have until I decided to go with you. ... Hannah will never forgive me for that," she added.

"So instead of winning enough money to keep your place, you now owe two of your best friends a lot of money and you're homeless," I concluded.

"Yeah, well, it's only money," sighed Jaycee.

I guess that response was typical of her care-free outlook, but it was also damn irresponsible. I knew that she was better friends with Susan than with Hannah. Why I have no idea since I thought Susan was one of the more annoying people I've met. But tonight, not only had Jaycee lost Hannah as a friend forever, it had to put a severe strain on Susan's friendship as well.

"So why are you behind on rent?" I asked. "As a physical therapist, you should be able to pick up extra shifts and high paying part-time work anytime you want."

"That may have been true a year ago. Heck, maybe even six months ago. But the economy the way it is, that's just not the case any more."

"What? That doesn't make any sense. There's always a need for health care, especially with the population getting older all the time," I reasoned.

"Well, I wasn't actually a full-time worker at the hospital. I liked my freedom, and I didn't see the need for benefits, so I was working just two or three days a week at contract rates," Jaycee responded.

I knew a little bit about this from being with Hannah for so long. Hannah and Jaycee were friends and roomies from grad school, and worked in the same field. Working contract paid you twice as much on an hourly basis (and that was a good chunk of money) but gave you neither benefits nor security. Luckily, almost all hospitals and other health care facilities are permanently understaffed, so there's always a demand for contract workers.

"So what changed? How did the economy hit health care?" I asked.

"Not health care, health care workers," Jaycee explained. "Do you know what kinds of guys are most therapists married to? Plumbers, electricians, guys who work in the housing industry. When the market dried up, all those guys were laid off or had their hours cut way back. So all their wives who had only been working on reduced hours suddenly started demanding full-time work and overtime. And they are all more senior than me, so I'm left holding the short end of the stick."

"That sucks. And you had some kind of side business?" I prompted.

"That very few of my clients want to spend money on now since it's a luxury that they can no longer afford."

"You've always been very secretive about that." Jaycee remained silent. "Us guys sometimes joked that you must have been a high priced escort."

Jaycee laughed at that. "And to think I was embarrassed to tell you. If I had known you guys thought that then I would have spilled the beans a long time ago. No, I'm a masseuse."

Hot damn! My week just got even better!

"Wait a minute! You used to get me to sneak you back massages behind Hannah's back, and you're a damn masseuse?!?"

I tore my eyes away from the road to peak over at Jaycee's side of the car. She was biting her lip and nodding her head.

"Damn. If I wasn't so committed to being fair and only punishing you for things you do wrong starting tonight, I'd give you a good spanking for that just on principal," I laughed.

"You're not going to spank me really hard, are you Will?" asked Jaycee.

"So long as you're good, you need never find out," I answered.

I pulled the car into my parking garage, remotely opened the security gate, and found my reserved spot. We kept up the conversation as we walked inside.

"So where do you play poker?" I asked. "You have to play regularly."

"Online. Maybe two to three nights a week," she responded.

"Jaycee, you didn't learn how to give that fake tell by playing online. Those tricks don't work when no one can see you."

"Oh that," Jaycee giggled. "I learned how to play poker in college. I dated this boy who had a regular game with his frat brothers and he used to humor me. When he got tired of answering my questions, or realized he didn't know the answers, he bought me a few books. Then when I turned twenty-one I used to hit the riverboat casinos back home. That was before I came out here for grad school. How about you? Do you play online? You're good enough to do well there."

"Thanks, that's sweet of you to say, but I'm not really. Besides, I don't trust those sites. Once I took a day and drove out to the Indian reservation casino a few hours west of here. But really I've just been content to play in our friendly weekly game."

We came up to the security desk. The guard on duty tonight was Paul, a gentlemanly ex-cop in his late fifties. He took one look at Jaycee wearing nothing but her too short winter coat and raised his eyebrows at me, as I was obviously carrying Jaycee's still folded up clothes.

"Paul, this is Jaycee. I got her in a poker game tonight and it's going to take me at least a week to figure out what to do with her. So you'd better give her a guest pass." Jaycee just smiled at Paul and batted her eyelashes at him a few times.

"Sure thing Mr. Jennings, though won't that mean she can leave whenever she wants? I'd be happy to swat her back into the elevator for you if she ever tries to escape," offered Paul.

Jaycee's mouth dropped in faux surprise. She could tell we were joking around. Paul was actually getting things organized to create Jaycee's guest pass.

"That's awfully nice of you to offer, Paul. But if Jaycee wants to escape she's more than welcome to. I've spent a few nights at her place over the years and she snores like a hibernating bear that's allergic to winter. When I said I got her in a poker game, I didn't mean I won her as a prize. I had to take her with me 'cause I lost!"

Jaycee turned and punched me in the arm for that comment. "Asshole!" she said, but she was smiling.

Paul shook his head and then pointed at a piece of red tape on the floor. "Miss Jaycee, if you would just stand there I'll take your photo for the guest pass and then you two can get upstairs and warm up. You just remember to give this back to me when you're done. I've got to keep track of every one."

Jaycee and I went up to my apartment on the twelfth floor, as I walked in I turned up the heat to make things more comfortable for Jaycee, hung my coat up, placed her clothes in the top of the coat closet, and then held my hand out for her coat. She slowly slid the zipper down the front and wiggled slightly side to side as she peeled the two sides back and slid the sleeves down her arms. That was very well done.

I took her coat, hung it up, then turned back to her. She was posing like a bashful tease. She had her right hip jutted out to the side, allowing her to squeeze her thighs together with one leg slightly in front of the other. Meanwhile, her right arm was imperfectly crossed across her chest, hiding her right breast but falling under her left. Her left hand was holding the end of a strand of hair to her mouth and her head was tilted down slightly so she could look up to me through her eyelashes. I soaked up the sight of her so that I could remember this moment for a long, long time.

I smiled at her, and then crooked my finger at her in a come hither. She smiled, dropped her arms and slowly walked to me. I put my hands around her face and kissed her, just wetting our lips with each other's. Then we kissed again, and again, and then opened our mouths to accept the other fully. Damn, she was a good kisser. My hands fell to her back and I pulled her tightly into me as we kept kissing. Her hands gripped the front of my shirt and pulled me towards her. My left hand then moved from the small of her back down to her butt. It was surprisingly cold, and Jaycee jumped back when I touched it. That reflex again. Well, the only way to break her of that was to get her used to my touching her there.

"Sorry," mumbled Jaycee.

"Come with me," I ordered. I returned my hand to the small of her back and led her through the living room and down the hall past the guest room and guest bath to the master bedroom.

I made a beeline for the bed and then quickly grabbed Jaycee, sat at the edge and forcibly maneuvered Jaycee face down over my lap with her beautifully, bouncy bottom as her highest point and the blood rushing to her head as it dangled near the floor.

"Will!" she screeched.

I placed my left hand firmly on her back to hold her down and gently rested my right hand on her butt.

"This is the position you'll end up when you're bad," I told Jaycee. I started rubbing her behind gently. "The first time you're bad, I'll only give you one spank," and I tapped her butt once. "Since it might take you a bit to learn to follow my orders, I won't want to get a sore hand. But the second time, I'll give you two spanks," and I gave her another two little taps, then went back to rubbing her. "I'm sure you can figure out the pattern from there."

Jaycee was shaking, and I was pretty sure it wasn't shivering from the cold.