Side Bet Bluff

Part 4 – Sunday Afternoon

Fifty minutes later I was walking into the women's section at our mall's biggest department store with my computer bag over my shoulder and one of my three pound contract binders loading me down. Jaycee had two bags from just one other store and was wrapping up a transaction for a dress here. It looked black. Good, at least she got the minimum. I just shook my head in disgust as I walked up to her.

"What? What's wrong?" she asked.

"I bet you haven't made a dent in spending my winnings, have you?" I asked.

"Hey, I'm good," she replied as she handed me back my credit card. "I've gotten two outfits and a dress for less than two hundred."

"If I was married to you, I'd be overjoyed," I deadpanned. "Come with me," I ordered, and led her back out into the mall.

"Will? What's going on?"

"Jaycee, let me give you my general philosophy on shopping," I answered.

"You have a general philosophy on... of course. You know, Will, you really picked the right profession."

"You will attend to me diligently as I instruct you on life's lessons," I said haughtily.

"Yes, master," Jaycee said coquettishly. Ooh, I just loved it when she said that. It sent tingles down my spine.

"If one can afford it, one should always buy quality, focusing on clothing or items that never go out of style. Make your purchases last. Not only do you develop the reputation of someone with refined tastes, but it is actually more cost effective in the long run."

"Ok," Jaycee replied doubtfully. "How is spending twice as much money on an item more cost effective?"

"It is if it lasts three times as long," I answered.

"Well, then what's the matter with my black dress?" asked Jaycee. "It's lasted me a good while."

"No it hasn't, because it looks old. It no longer looks black but more of a darkish grey, and it hasn't faded evenly either. If that dress had been made of qualify fabrics, then you'd still easily be able to wear it out to a nice dinner without embarrassing your date."

"And what if you can't afford silk and satin and the hot new fashion label?"

"Then make do with the bare necessities, and go without until you can save enough to buy quality."

I led her into the really nice department store.

"Will, you're going to blow all your winnings in fifteen minutes here," she warned.

"Don't you worry about it, this isn't even our last stop." I led Jaycee around until I spotted a saleswoman in her forties who looked like she was both professional and refined. It's a hard combination to pull off. I walked over and introduced myself to her. "Hello, I'm Will Jennings."

"Pleased to meet you, Mr. Jennings. My name is Rebecca Thornton."

"Hello, Rebecca. This young woman behind me is Jaycee Wade. She is in need of a number of outfits that are sadly lacking from her wardrobe. I was wondering if I could impose on you to help her for the next half hour or so?"

"I'd be delighted Mr. Jennings. And what types of outfits did you have in mind?"

"Jaycee needs two outfits for the office. Not a suit, but a nice professional looking blouse and either slacks or a skirt. She'll need an outfit for a cocktail party, and another for an elegant dinner on the town."

"Of course. I'm sure I can take care of that for you."

"Oh," I added. "And a new pair of nice jeans and a couple of tasteful sweaters she can lounge around in instead of her old college sweatshirt."

"Anything else?" she prodded. "Shoes? Belts?"

"Definitely, whatever is necessary to complete the outfit."

"And price range?"

"Don't go running for the most expensive items in the store, but other than that ... the emphasis is putting together the outfits that Jaycee will look best in."

"I think I understand," she assured.

"Jaycee, just give me a call when it's time to pay the bill. I'll be in the coffee shop trying to get a little work in." Jaycee looked at me completely shell-shocked.

After I was five steps beyond her, Jaycee called out, "Will, wait!" She ran up to me and quietly said, "Will, you don't have to spend all this money on me. I'm already yours for the week, remember?"

"I know, darling," I returned. "I'm doing this for the both of us. I'm buying you things because I like buying you things. But also because now that I've got you for a week, I plan on showing you off to everyone I know. And if I'm going to make every guy in the world jealous, well, you've got to dress the part."

Jaycee giggled, but said "that's nice Will, but there's no way I can pay you back for a purchase of this size."

"I don't want you to," I answered. "Now go back there, do everything that Rebecca tells you to do, trust her judgment when it comes to how good you look, there's a reason I picked her out. And don't look at a single price tag. That's an order."

Jaycee smiled at me and gave me a smooth as silk "yes, master." Ok, this time the tingles weren't in my spine. She then pressed up against me and gave me a sultry kiss, right there in the middle of the store. After she broke it, she gave me one last smile, turned around, and walked away with an extra swing in her hips. To think last night I implied I'd take one night of a blathering Susan over a week of this woman? I must have been out of my mind.

On my way out, I stopped by the men's department for a couple dress shirts and neckties. My favorite sales lady Ruth hooked me up. When I was growing up poor, I never would have imagined that I'd have a job where I went through so many dress shirts and ties in a year, least of all be on the first name basis of a salesperson who kept me in good supply.

It was at least forty-five minutes before Jaycee called me to come back. They weren't by the cash register but back in one of the dressing areas. It had a seat all ready for me before an elevated platform surrounded by mirrors. They had arranged a fashion show for me. I would have preferred to just pay and go, but I recognized this was part of showing my appreciation to Rebecca for her selections. And by the comments Rebecca was making to Jaycee, it was obvious that she viewed Jaycee as a project and was trying to teach Jaycee not only how to dress like an impressive yet refined woman, but how to act as one. I hoped it didn't stick. Jaycee had a lot of rough edges, and that was part of her charm.

At one point while Jaycee was in a dressing room changing outfits, Rebecca turned her attentions on me.

"Miss Wade informed me of the nature of your relationship," she stated.

"I'm not surprised," I admitted. "Jaycee tells everyone everything."

"You don't seem embarrassed by it," she said, seeming astounded.

"Embarrassed about what? Jaycee's lack of a filter or the nature of our relationship? Either one, no, I'm not embarrassed at all."

"I guess you two are a good fit, then. Miss Wade admitted to me that she found the whole experience rather liberating."

"Oh, yeah?" I asked, with a broad smile forming on my face.

"Yes, even when you were ... punishing her."

"Ah, yes. Well, Jaycee has a bit of a phobia that her punishment is designed to overcome."

"Do tell," implored Rebecca.

Too late, Jaycee came out of the dressing room with her final outfit. A light blue blouse that could be worn under a suit just as well with jeans, and a grey pencil skirt with matching light blue pinstripes. To complete the outfit were dark blue shoes with a two inch heel that looked professional yet feminine.

"This outfit costs more than my last paycheck," Jaycee muttered to herself as she got up on the platform.

I looked at her sternly. "I thought I ordered you not to look at a price tag."

Jaycee gasped and turned towards me. Then scrunched her eyes together in frustration and clinched her hands into fists.

"Assume the position," I ordered.

"What? ... Here?"

"If you want to avoid public punishments, then you need to be extra careful not to break any rules in public. Now, how many spanks do you get?"

"Ummm, five?" Jaycee asked, still not moving from the stand while placing her hands behind her in a protective position. "Will, please, not here. Can't we do them at home?"

"I'll let you choose, your regular amount here, or double at home."

"Mr. Jennings," Rebecca said strongly. "You cannot possibly take your hand to this woman. Not here, not for so meaningless a transgression," she sputtered.

"It wasn't a meaningless transgression. I only give orders that I want obeyed. And are you going to force Jaycee into taking the greater punishment by preventing me from attending to her now?"

"I ...," began Rebecca. "You ..."

I turned back to Jaycee. "Jaycee, that outfit looks very nice. Now slip the skirt off and hand it to Rebecca, then assume the position."

And Jaycee slowly, meekly, maybe even nervously, did just that. She unhooked, unzipped, then removed the skirt, folding it neatly before handing it to Rebecca. Did she fold everything? She then came over next to me, and folded herself over my lap. I pulled up the ends of the blouse and pushed them up her back a bit, then pulled down her silky black panties.

"Where did these come from?" I asked, holding the underwear in my hand. I didn't think Jaycee had changed at her old apartment.

Jaycee looked back at what I was referring to. "They're being added to the bill," she admitted.

"Nice," I commented. "Count them out for me, my darling Jaycee."

[SMACK!] I wasn't going easy on her.

"Ugh," Jaycee grunted. Out of the corner of my eye I could see Rebecca jump. She was still facing us. "One," Jaycee said softly.

[SMACK!]

"Ermph" In between spanks I was softly touching Jaycee's ass, as had become my habit. It was such a beautiful ass. "Two"

[SMACK!]

"Ah!" Jaycee said softly, then took a big breath. "Three."

[SMACK!]

"OH!" Jaycee cried out. But she kept the same pace with her counting. "Four." That last four sounded odd, like it was in stereo. Now that was interesting.

[SMACK!]

"FIVE!" Jaycee all but screamed.

I stood Jaycee up, and she pulled her panties back into position. I grabbed her left arm and turned her to me. Then gently placed my left hand on her cheek and gave her a kiss on the lips. She had tears in her eyes, but she wasn't crying.

I turned her towards Rebecca, who was standing with her right hand over her chest in a classic "oh my!" expression right out of old movies. "Thank Rebecca for allowing you to receive your punishment here," I instructed.

"Thank you Rebecca," Jaycee said, while rubbing her bottom. "I don't think I could have handled ten."

I then walked Jaycee back to her dressing room. "Now take all the clothes that we're getting and hand them to Rebecca to ring up for us."

Jaycee nodded as Rebecca, hearing us, followed us to the dressing room door. Jaycee re-opened the door, wearing just her black panties and a matching strapless bra, with everything else on hangers. Rebecca took them, gave us one long look, then turned and walked away.

"Will, I'm sorry," Jaycee began. "I'll never disobey another order, ever."

"Good," I said, "that's the primary point of the punishment." And I gave her another kiss, one which she returned in a manner that was somehow both sweet and passionate. I pushed her back into the dressing room, and hearing the door close automatically behind us, broke the kiss and pushed her panties down past her hips, whereupon they fell to the floor.

Jaycee looked at me with eyebrows raised as I repositioned us with my back to the bench. I unbelted, unbuttoned, and unzipped my pants, pulled them down to my knees, then sat back onto the bench. My cock pointed straight up, a missile on its launching pad.

"Oh," Jaycee said, eyeing my dick. "Spanking me created a different primary point."

Without another word, Jaycee straddled me, took hold of my dick, positioned it at her entrance, and slowly lowered herself onto me. I slid in easily, as Jaycee was already soaked. Since I was sitting, Jaycee set the pace, raising up and lowering herself back down, each time taking a little more of me. But this wasn't a slow build-up. We were ready, and we wanted to get off. Within seconds I was sucking on her neck and grabbing her hair. We tried to keep it quiet, but the wet sounds of our bodies slapping against each other permeated the area.

She leaned back to give me access to her breasts, and I dove in with gusto, licking, sucking and nipping at them. She then leaned back further, threw her head back, ground herself fully down on me and screamed, "MASTER!!!"

That did it for me. I pulled her hips to me as strongly as I could, then unloaded into her. I pulsed with Jaycee, and she shook above me, our combined vibrations adding to our sensual sensations.

Before we could finish calming down, Jaycee pulled herself upright and looked me straight in the face. She didn't say anything, just looked at me. Next thing I knew we were kissing, passionately and wetly.

I hated to end it, but we were still in a semi-public area. I pulled back and pushed slightly on Jaycee's hips, letting her know through touch that she needed to get up. As she did, we "disengaged" from each other, leading to both of us giving a little moan. We followed that up with grins at each other. It seemed we were perfectly in synch, thinking and feeling the very same things.

I pulled my pants up, tucked my shirt in, buttoned, and was ready to go. Jaycee, not so much.

"I'll be paying for your clothes. Why don't you go get cleaned up?"

Jaycee nodded. "Thanks. And Will? You weren't the only one turned on by my punishment."

I laughed and headed out towards the shopping area. It suddenly struck me that I didn't know who Jaycee meant with that last comment, herself or Rebecca?

As I emerged from the dressing area, Rebecca was taking down a large ribbon from next to the door. She glanced at me, and quietly led me to the register.

"I take it you approved of everything I selected for your young paramour?" Rebecca finally asked, though she couldn't bring herself to look at me for more than a fleeting moment.

"Everything looked fantastic on Jaycee, I'm very pleased."

"Very good, Mr. Jennings," she answered.

"I'm a little surprised that no one else entered the dressing room while we were back there. I know the store doesn't appear to be very busy, but ..."

"There's a way that us salespeople signal to each other for privacy when we have a special client."

"In that case, Rebecca, I'm even more pleased. Thank you for everything."

"My pleasure, Mr. Jennings."

I eyed a purse, a wallet, two belts, and four boxes of shoes to go along with all of the outfits, plus the empty packaging for the underwear that I guessed Jaycee would be wearing out of the store.

Rebecca saw me eyeing everything and said, "Miss Wade tried to resist me adding most of these items, and she was successful in declining the winter overcoat, saying that .. that ... purple ... thing ... more than sufficed."

I could tell what Rebecca was doing, but it was definitely working. "Why don't you include the overcoat."

"Excellent sir. In that case, your total purchase comes to ..." Ok, I'm not going to give you that piece of info. I don't want you dropping dead from a heart attack at your computer.

After I got everything squared away, Jaycee re-joined us. Good, I needed her to carry at least half of this stuff.

"Well, it was very interesting meeting you both. You two make me wish I was young again," Rebecca pined.

"Oh now Rebecca, you're only as old as you feel," I told her. Jaycee smiled and nodded in agreement.

"As I said, you two make wish I was young again."

"I think you were feeling very young just a little while ago," laughed Jaycee. And with that we walked back into the mall, leaving a blushing Rebecca behind.

We swung by the car to drop all of Jaycee's clothes off before hitting the final store. And I know it's cliché, but I did much the same thing at the mall's lingerie shop. Hey, I told Jaycee I was going to make her get some.

I instructed Jaycee to look around while I went in search of an able professional. It seemed like the store had hired only teenagers from the local high school and I was starting to despair when out from the back came a woman probably in her thirties. She was wearing a form hugging short, black skirt with matching jacket, patterned black hose, hair pulled back, and fashionable eyeglasses.

She introduced herself as Bethany. I pointed out Jaycee, and then explained what I wanted. She had good follow-up questions.

"Colors you prefer?"

"Black and white predominantly, and I like solid colors, not mixes or patterns. I'm not a big fan of all this red, but maybe one outfit wouldn't be bad. An occasional alternative color could signal a fun, playful night. But absolutely, positively no animal prints."

"Materials?"

"I'm not a fan of a lot of lace. Other than that, I don't really have a preference."

"Ok, now most important – style. Do you prefer classy, flashy, or trashy?"

"There's a reason I picked you out instead of going to any of the teeny-boppers. Classy. Mostly classy. I'm a bit of a traditionalist when it comes to lingerie."

"I could have predicted that, though with the distaste for lace I couldn't be sure. Ok, I think I understand. And I've got the number of outfits. So, is that the only limit, or do you want to set an overall price limit?

"No price limit. The limited number of items should hold you two back enough. And don't let her buy things that you don't think I'll like. Not even if she tries to use her own credit card. Ok?"

I signaled Jaycee over, introduced them, and explained to her that I didn't want a fashion show this time. She was going to have to show everything to me one outfit a night for the rest of the week. Jaycee seemed to like that idea. I handed her my credit card once again, then already shifting back into my work mindset went next door to yet another coffee shop. I swear there were more of them in this mall than department stores.

"Here's your credit card back," Jaycee said, while leaning over my table with what looked like six pink bags in her hands.

"Thank you," I said putting it back in my wallet and stealing a glance at my watch. I don't know how it's possible, but Jaycee took almost as much time buying lingerie as she spent with Rebecca.

"Can I ask you a question?" Jaycee asked.

"You can ask me anything. Of course, rule number three about absolute honesty doesn't apply to me, but I strive to speak truthfully."

She hesitated a bit, like she was working up the courage. "How come you said this morning that you and Hannah broke up after three years together because you couldn't afford to spend any money on her, and now you're spending gobs of money on me after only one day?"

I finished packing my things up and directed Jaycee back towards the car.

"It wasn't that I would never be able to spend money on Hannah," I explained. "It's that I didn't have the money to spend on her at that particular time. I've got more money to spend these days."

"But," Jaycee protested, "you said you invested money, and everyone's lost their shirt in the stock market this year. Plus, you said that your firm could start laying people off. You should be saving your money instead of wasting it on me."

I stopped walking, turned to her, and kissed her. "That's very sweet, Jaycee. You're just going to have to believe me when I say I can afford this. And spending it on you is not a waste."

"Well," she began nervously. "I'm just thinking that maybe you're one of those nice guys you were warning me about. You know, who spends more money on me than they can afford in the hopes to get into my panties."

"I'm already getting into your panties," I reminded her, turning her to start walking again.

"Right, so if you're not hoping for that, maybe you're hoping for something else?"