Side Bet Bluff Ch. 08

Part 8 -- Tuesday Afternoon

Later that afternoon I took Jaycee to my gym. I have difficultly staying motivated to work out during the winter months as I hate running on a treadmill. I'd much rather be out at a park or riding a bike on one of several nature trails around the city. But as much as I hated running on a treadmill, I hated breathing in freezing cold air while exercising even more. At least the gym had televisions where I could catch up on the day's news, which today was dominated by the new president's inauguration.

Unlike most of the women in the gym, Jaycee wore just a regular t-shirt and shorts instead of the matching, cutesy workout outfits designed primarily to capture people's attention. Even though a wardrobe designed to attract a man's eye on the right body shape will always be appreciated, Jaycee's lack of pretention had its own special charm. Jaycee had this odd, loping gait when she ran that I found humorous. I think the expression "you run like a girl" may have originated by watching Jaycee. You'd think being a physical therapist she'd have analyzed and corrected her gait, but no. It looked completely unnatural. Yet she threw herself into it with no thought to how she may look to others.

After exercising, we cleaned up and I took Jaycee out for dinner at one of my favorite casual restaurants. Our conversation focused on the day's events. Jaycee announced that she had lined up two appointments with massage clients for the next day to keep her occupied while Karen and I would be meeting Beck. One of my best friends had called earlier in the day, saying that he and his wife Siri were going to be in town with Beck, and wanted to schedule a Friday lunch with our favorite business school professor. I found myself telling Jaycee about him.

Billy and I knew each other from high school. He was off-the-charts brilliant. That may sound like hyperbole, but really I doubt an IQ test could come close to accurately measuring his intelligence. I first met him by sitting next to him in our Advanced Placement Computer Science class. For the first three weeks of the year I thought I was failing that course. Only then did I realize that by trying to keep up with Billy, I was actually way ahead of everyone else. Even though he was a year younger, he and I became fast friends. It was then I started going by 'Will' instead of 'Billy' as I got tired of both of us responding whenever someone called our name.

He went off to one of the Ivy League schools for college while I stayed local, attending the cheap, state-supported school. But we ended up at the same grad school. My joint degree program had me do the first year of law school, then the first year of business school, followed by a mixture of classes from the two schools the last two years. So even though Billy had been a year behind me in high school, he joined me for the first year of business classes.

By luck, we had been placed in the same section and instantly formed the leadership of the single most dominant competition team the b-school had ever seen. His analytical brilliance combined with my persuasive arguing and presentation skills proved nearly unstoppable. We destroyed everyone in our path. All but for one loss, which is a story I'll leave for another time.

Billy had offers lined up from all the top investment banks well before he graduated. He joined the most prestigious and highest paying firm up in New York City and met Steven Beck there. All of a year later, Beck spun his division off to form his hedge fund and took Billy with him. I met Beck at Billy's wedding, and was surprised to discover that my biggest competition in our fantasy football league was twice my age and ten thousand times my net worth.

"So that's the secret?" Jaycee asked me.

"What secret?" I replied.

"I asked yesterday how you got Beck as a client and you hushed up. And the answer is, through one of Beck's employees who is your best friend from high school. I was expecting something scandalous, like you had a sex tape featuring him or something."

I had to laugh at that. "You've been listening to Susan too much with all of her talk about celebrities and their sex lives. I guess I was embarrassed to admit I met him through a fantasy football league."

"Hey, whatever works," quipped Jaycee. "So you really think he's going to make you a job offer?"

"It certainly sounds that way, though I'm just hopeful I'll still be able to do some work for him down here. He's a hard person to say 'no' to, though. Thwarting his wishes while still staying on his good side takes a lot of effort. He's used to getting his way."

"You've had to 'thwart' him before?" Jaycee asked.

"A couple times when he wanted to do something that was barred by a law or regulation," I explained. "It happens with every business client."

Our conversation continued regarding my job situation. Jaycee expertly pulled information out of me with leading questions and a focused interest on my answers.

I had managed to get a little over twenty potential clients on the phone today, and left phone messages or emails with roughly another ten. I'd count myself lucky if I could get work from more than a handful of them. It was tricky trying to get them to commit to me while being vague about what resources I'd have at my disposal to use for their benefit. I couldn't tell them I'd be staying with the firm but in New York City, because I couldn't make that call yet. I couldn't tell them whether I would or would not be working with Glenda.

For most of these clients, the best I could get from them was a promise not to commit to anyone else until I made a decision. All except Premolex Manufacturing, who hinted strongly that I could join them as in-house counsel if I wanted. Karen had recommended that call when I was starting to get discouraged, knowing it would boost my ego and pep me right up.

Included in those figures were the five clients that I had found on my own over the past two years, including Beck. I just needed to get signed letters from them saying that I was going to be their legal representative from this point forward in order to get all of their files back from the firm. It was merely a formality, but an urgently necessary one.

Four other newly laid off associates called me during the day, just checking in and looking for the latest gossip. I was surprised at how little they knew, both about what was going on and concerning their own future. All four put on a confident front, explaining how they were going to be just fine, how they had plenty in the bank just in case of a rainy day, how the firm had been stupid to lay everyone off and that other firms were going to be pounding down their doors to hire them. Yeah, right. It was easy for me to agree with them. After all, their lies were my truth, and I was confident that I'd have gainful employment again soon. But I wasn't as confident about them.

I paused momentarily to consider Jaycee's situation. Here she was wallowing in debt, with no steady work and really no prospects for a job until the economy turned around. Yet her unique attributes were immensely valuable. Jaycee's uncanny ability to get people to open up to her and tell them their secrets would be worth her weight in gold to a litigator. Heck, to a corporate attorney used to doing deals as well — any bit of extra information gleaned from those on the opposite side of the negotiating table could save millions.

Could I really be thinking of offering Jaycee a job? I shook my head and refocused on the conversation. I needed to think about my own job prospects first and foremost. And I'd actually done enough thinking about that today already. Now it was time for some fun.

We made a stop on the way home at a Pleasure Palace store, a rather successful local retail chain that sells costumes, games, and sex aids.

"What are we doing here?" Jaycee asked.

"I've been thinking about what taking your ass is going to entail, and I think we may need some extra help for when we do the deed," I answered.

"Oh, like tying me down to the bed so I don't start punching and screaming?" Jaycee suggested.

"No, though that sounds like a good idea," I laughed. "I was thinking along the lines of prepping your ass for me."

"Really? How would you do that?"

"I don't know," I admitted.

"You don't?"

"No, I've never actually had anal sex. I don't know everything," I admitted.

"You don't?" Jaycee said, in what sounded like a revelation. "I guess I've been operating under the assumption that you did."

"Did what? Know everything?" I asked.

Jaycee gave me an abashed smirk and nodded affirmatively. I just laughed.

As we walked inside, there were two women behind the checkout counters in the middle of the well-lit store. A collection of outfits clad on mannequins were displayed on all four walls, including a prominent window display to intrigue passing drivers. A series of display cases and shelves filled in the remaining floor space, mostly taken up with videos and magazines. I'd only been in a store like this once before, on a lark with Hannah and another couple. This wasn't some dark and dingy store for the perverse underbelly of society. Instead, this was a tribute to how pornography and sexual adventurism had gone mainstream.

The younger of the two women gave us the once over. "Can I help you two find something?" she asked.

"I think we'll just look around at first," I replied.

Jaycee jumped in loudly with, "Are you sure, Master? Why not just ask what they have here to help prepare my ass for you?"

I just had to sigh at her pronouncement. I should have predicted Jaycee's natural propensity to try and shock people would rear its head as soon as we stepped into this store.

The saleswoman turned to her co-worker. "Marie, these are for you."

Marie looked to be in her early 30s, displayed a Rubenesque figure, and had a heavy Southern accent. It turned out that Marie called herself a 'submissive', and had been with her Master for six years. She was very helpful in suggesting a range of toys and devices to help us explore this new channel for our sexuality. She also figured out very quickly that we were neophytes.

"You do have a safe word, right?" Marie asked.

"A safe word? What's that?" I returned.

"Oh goodness, you two are just jumpin' into the pond without knowin' if you can swim, ain'tya? The first thing y'all should do when you get home is get online and start readin'. Actually, there are several books we sell here that you should take a look at, too, but I'll write down some websites for y'all to check out as well. But pick out a word right quick that will be easy to remember but won't come up reg'lar in conversation, or bedroom play neither for that matter. And then if you, William, ever do anything that Jaycee here really don't like, then she calls out the word and you stop."

"Isn't that cheating?" asked Jaycee.

"Oh no, Sugar," Marie said vehemently, "no matter how similar your beliefs and kinks are to your Master's, there's always going to be some things he wants which you don't, and some things you want that he don't. So the safe word is your security blanket. It's there for when that situation pops up. And remember, you need to always be 'safe, sane, and consensual.'"

"Ok, but ... , I mean, ... take anal sex," Jaycee explained.

"Yes, please," interrupted Marie.

Jaycee bit her lip and looked chagrined.

"Oh, look at you all flusterated," added Marie. "I'm sorry, girl, do go on. What were you fixin' to say?"

I don't think I'd ever seen Jaycee so 'flusterated.' I liked that word. Maybe I could incorporate it somehow into my next legal memo.

"I'm really scared of it. Anal sex that is," explained Jaycee. "I mean, petrified. But I want to do it. And more importantly, I promised Will that we'd do it. But if you gave me a word like that, I'd say it every time Will even touched my butt. I just know I would."

"Well, baby girl, you can either up the stakes for saying the safe word, or just make an exception for that situation. Like me, for instance. There's some things I never do, that's a hard limit. Some things I sometimes do, that's a soft limit. And some things I'll always do. So if my Master ever tries to go past one of my hard limits, then we're through. But on the other end, if I ever try to get out of something I've agreed to always do by usin' my safeword, then Master will just ignore it. Of course, neither of us would ever do that to each other, but it's good to tell you. It's only on the soft limits that the safe word applies. See? You talk it through beforehand so that there's no mistake. So for you and anal sex you could say 'You are allowed to do this and ignore the safe word, but not anything more.' And have a backup too. Sometimes my Master likes to gag me. Obviously I can't say 'radishes' in such a situation."

"Radishes?" I asked.

"Sure. They're red, which means stop. And neither me or Master likes 'em, so that's another reason. And because we don't like 'em, we never have 'em 'round the house, so there's no chance to accidentally say that word. See? You got to think it through. And when I'm gagged, he's very careful not to try anything new, or he'll give me a gesture to do instead. One time, when we were brand spankin' new at this, I was tryin' to do the gesture but we hadn't practiced it aforehand, and he weren't gettin' it. I was shakin' so hard, he thought I was havin' the biggest orgasm of my life, so he kept strappin' me harder and harder. Since that weren't workin', I started tappin' S-O-S out in Morse code against the headboard with the side of my handcuff. It took him a couple minutes before he finally got it figured."

"Yikes," Jaycee said.

"Yah," agreed Marie. "Master was so upset with hisself. That's the awfullest he done ever felt," she said looking very pointedly at me. "So that's the 'safe' part of safe, sane, and consensual. Be careful. 'Cause accidents in this area really hurt."

"Communication is always a good thing," I added.

"Exactly," Marie agreed. "Communication is always a good thing. And the most important thing is figure out and do what makes sense for you. The books and the websites are there to give you ideas, and to explain some things to y'all. Just remember, there's no right way or wrong way to learn this lifestyle. Just don't bite off more than you can chew. You have to take small steps and figure out what you like and what you don't. But if it don't feel right, then don't do it. And who cares what anyone else thinks. This is as personal as it gets."

"So Jaycee, you care what anyone else thinks?" I asked.

"Never," she replied. "Speaking of which, I've been eyeing that black leather straight jacket with the boob cut-out over there. If I was wearing that then there's no way I could accidentally hit you by flailing about when you take my ass. That looks a lot more comfortable than tying my arms behind me with a necktie. Marie, do you think that would fit me?"

"That one yonder? Let's go try it out."

I wandered off on my own to do some browsing, and picked out a few items for purchase. I spent a good amount of time comparing the various forms of lubrication. I hadn't considered that there would be lube designed specifically for anal sex, though their labeling made a compelling case for it. Marie checked in on me a couple times and was very helpful with suggestions and even shared some ideas with me. Unfortunately she informed me that the straight jacket wasn't a good fit for Jaycee. Too bad.

I found Jaycee looking at some of the books Marie had recommended. She seemed especially fascinated by a chapter on whipping.

"That's quite a leap from our present activities, don't you think?" I asked.

Jaycee jumped. "Oh, Will. You startled me." She looked a little embarrassed at being caught reading the book. "Sorry."

"Why 'sorry'? Is it interesting?"

"I hate to say it, but yeah, kinda. I'm fascinated by the anatomical knowledge being displayed in this book. There are a lot of similarities to gate control theory here in the focus on pressure points and the subsequent release of tension."

"Gate control theory?" I asked.

"Think of it as one of the theories behind massage," Jaycee answered, "only here the purpose is to actually activate pain sensors instead of inhibit them."

"You think you'd be into that kind of thing?" I asked, with today's spanking session and Jaycee's assuredly still red bottom on my mind.

Jaycee took a few moments to think before answering. "Before this week, I would have automatically said 'no'. Now?" She shrugged. "I don't know. I do find it fascinating, though."

"Perhaps that's all of your training influencing you?" I suggested.

"Perhaps," she agreed. "I am engaging the material in this book on a more intellectual level than emotional."

"So grab a couple books on the subject and we'll add it to the bill," I urged.

"Oh, gosh, Will, I'm forcing you to spend another small fortune here, aren't I? Can I pay for my share?"

"With what?" I asked. "Your last fifty bucks? No. Everything's on me."

"Hmmm, well then it would seem a waste if we're just going to buy all this stuff and only use it through the end of the week," she hinted.

"You mean," I stalled, trying to decide if I wanted her for more than the one week. Part of the excitement of this week was having the fixed time limit on it. Extending it into an open-ended relationship certainly had its obvious attractions, but also increased my responsibilities and would likely lead to us falling into routine and eventual monotony.

Jaycee grinned at me and gave me a little shrug of her shoulders, and a little twinkle in her eye.

"Really?" I asked with all kinds of loaded meaning.

Jaycee lowered her head and looked up at me through her eyelashes. Her grin slowly widened into a small smile and she batted those eyelashes at me. I wish I had more time to think about this. Best to leave myself open to the possibility.

"Hmmm, well, we'll see," I said, taking her by the arm and leading her towards Marie at the check-out counter. "That all depends on how good you are at following my commands for the rest of the week. You may not be worth the effort."

"Hey!" Jaycee said in mock outrage.

Marie rang up our purchase including books, padded handcuffs, butt plugs and dildos, a large black feather, two types of vibrators, a blindfold, lubricant, an inexpensive collar and leash set, a light bondage set specifically designed for a four-poster bed, and a large rectangular wooden paddle. Jaycee eyed that last item warily.

"Will, why are you buying that?" she asked with a tone of warning in her voice.

"If you continue to be a bad girl, I'm going to hurt my hand on your bottom," I answered. "And we can't have that, now can we?"

Jaycee didn't take her eyes off the paddle until it was safely ensconced in the plastic bag and hidden from her view. I asked Marie if they had a book that dealt with the more in-depth technical aspects of whipping. She actually added two websites to her list for us instead. She also grabbed a bunch more lube than what I brought up to the counter.

"Use it. Use a lot," she instructed. Ok, point made.

For as much help Marie had been, I hadn't spent nearly enough money to properly compensate her for the value we had received. I gave her a fifty as a tip.

"What's this for?" Marie asked.

"Your helpful advice; a valuable service should be paid for." Marie shrugged her shoulders, folded the bill and tucked it into her bra.

As we left the store I overheard Marie's co-worker say, "Damn, maybe I need to get into this bondage stuff if it pays that well."

"Ok, so about a safe word," I brought up as I drove Jaycee back to my apartment.

"We don't need one," Jaycee answered.