Side Bet Bluff Ch. 04

"Like what?" I asked her.

"Are you hoping I'll become a serious girlfriend?"

I stopped dead in my tracks. "No."

"You sure?"

"Ok, I'll admit that I've had a crush on you for a long time, and that if somehow this crazy roleplay turns into some kind of serious relationship ... I don't know, but we'll just have to see what happens. But that's not why I'm spending money on you. ... Jaycee, I've been living well within my means for a long time now. I'm making excellent money. I can actually afford to pay off my student loans right now but with them at such a low interest rate why should I? For the first time in my life I want to splurge a little and try to make this such a great week that I'll be remembering it years from now. In spite of Hannah's best efforts, I still think that's possible. Now I appreciate you worrying about me, and about all the money I'm spending on you. It's very sweet, but probably more an indication of how you're perceiving my actions through the lens of your own financial situation."

Jaycee looked thoughtful. "You may have something there."

"Alright. Then let's put this behind us once and for all. Don't worry about anything this week. I officially declare this a worry-free week. Anything I do for you ... or to you ... is with the intention of giving both of us pleasure. Hopefully a lot of pleasure. And there's more than just sex to do that, too."

Jaycee smiled. "Ok, I'll try to put aside any worries."

"Good," I said. "I know real life has and will continue to intrude upon us, but I want your normal carefree, roll with it, attitude. After all, 'it's only money', right?"

"Right," Jaycee laughed.

"Good, now there's one more stop to make before we head home."

"Another one?!? Criminy, what now?"

"Criminy? Who says 'criminy' any more? Besides, that sounds like you worrying," I warned.

"Ok, ok. Please, sir, could you deign to tell little old me what might our next destination be?" Jaycee said playfully.

"Cute. We're going to ... the grocery store!"

Jaycee cracked up. "Good! I used the last of your eggs this morning."

We got in the car and headed out, going over a list of dishes that Jaycee said she could cook. The way she had slimmed down since the summer, I had my doubts. Grocery shopping took another hour. This had become pretty ridiculous. What I had intended to be a two hour excursion had become a seven hour epic. The sun had long since gone down, and I still had several hours of work I needed to do tonight. And once again I was reminded why one should never go grocery shopping while hungry. I was surprised my credit card company wasn't putting a block on my card from all of the atypically large activity.

It took us three trips from my parking garage to the lobby to bring in all of our stuff. Paul was working the security desk again and gave us a cart for everything so we didn't have to go all the way up to my apartment first before getting the other rounds. All I had to do was send the cart back down in the elevator once we were done.

I gave Jaycee the closet and the chest of drawers in the guest bedroom for her clothes, though she insisted in surrounding the second sink in my master bath with all of her make-up and toiletries.

"Ok, you can finish that up later," I told her. "I'm starving."

"Yes, sir. Just let me change out of yesterday's clothes and I'll be right out."

I set myself back up at the dining table (if you could call it that – it fit the area, but I lived in an apartment, so it was pretty small). I had decided to let Jaycee have the guest bedroom as her private area, so my desk in there was off limits. Hopefully I could get my work done in another couple hours, though the intermittent nature of my work today hadn't made me very efficient. And I was worried how much time I should actually charge to the clients.

Jaycee walked out of the hall wearing a deep purple camisole that tightly hugged her torso, showcasing the rigid bumps of her nipples. She also had on a tight, matching, deep purple boy short, and a loose, untied robe of the same material and color. Her legs and feet were bare.

All thoughts of asset-backed securities and derivatives disappeared. She came to stand before me with her head tilted down but a grin on her face. I made a circling motion with my finger and she smiled, then slowly turned for me. When her back was to me I stopped her, and reached down as far as I could. I started just above the knee and slowly slid my hands up the backs of her legs, up under the robe, and onto her tightly enclosed butt. Jaycee twitched slightly, which was quite an improvement for just twenty-four hours. I put my hands on her hips and had her complete the turn to face me. I then continued my hands upward path over her encased stomach and up to her breasts. I didn't know what this material was made of, but I liked it, and I could only imagine it was incredibly comfortable. I rubbed my hands lightly over her breasts but didn't linger, continuing up her chest to her bare neck. I then pulled her to me and gave her a firm kiss, one that I hoped promised much more pleasure later this evening.

"Do you approve?" Jaycee asked, after finally pulling back.

"Very much so," I nodded.

"Good. I spent the longest time fighting with Bethany over this outfit. She kept telling me that you wouldn't like it."

I smiled at her. "I'm glad you won."

Jaycee nodded. "Ok, I'll get started on dinner. I didn't realize how hungry I was until I looked at the clock. How did we stay out that late?" I assumed that question was rhetorical, and went back to work.

Thirty minutes later I had to break for a scrumptious beef stroganoff and a side salad. Jaycee said it was low fat, but I certainly couldn't tell.

She tried to make dinner conversation by asking what I was working on. After two attempts to beg off I gave in and tried to explain it to her. I don't think I went more than thirty seconds before her eyes glazed over. I had warned her.

Jaycee cleared the plates while I went back to work, telling her I should be done in about an hour. God damn all asshole managers and their power trips. I could be spending great quality time with Jaycee right then instead of doing work. And tomorrow, I wouldn't have any work to do in the afternoon, but would probably be dragged into a stupid meeting that shouldn't have been called in the first place to be lectured at on something I didn't do.

A little over an hour later as I was wrapping up, I noticed I was almost sweating. That was odd. Yes, it was definitely warmer in here. Jaycee came out from down the hall, with the purple robe tied tightly around her. As I looked closer at her I didn't think the matching lingerie was being worn underneath.

She asked "All done?" I nodded. "Good, because I want to show you how much I appreciate what you did for me today."

"Sounds good to me," I agreed happily.

Jaycee led me into the guest bedroom where she had removed the blankets and laid down her portable massage table on top of the sheeted mattress. Covering it were a number of towels, along with a really heavy looking blanket made of an odd material. She had started some soft classical music playing and her massage oils were arrayed on the nightstand.

"Sir, if you'd please disrobe and get under the blanket, I'll begin your massage shortly."

I've had just a few massages in my day. Normally when the masseuse says that, they leave for a few minutes to give you some privacy. Jaycee just stood there looking at me expectantly. I gave her a smile and a wink, then began to disrobe. Jaycee took each article of clothing from me with hangers at the ready. When I was naked, I awkwardly maneuvered myself up onto the bed and table but under the blanket. It was an odd set-up. But soon I had my face sticking down into the hole for it, except instead of staring at the floor below I was looking at the mattress about a foot away.

I could hear Jaycee remove her own robe, then walk around to grab her oil bottles.

"Just relax," she murmured. "Remember, this is a worry-free week. And I'm here to give you pleasure and attend to your every need."

She was good. She was very good. I don't understand how she could have lost clients. I think I'd give up a lot of things before I gave up a regular Jaycee massage. She spent time massaging my back, my neck, my arms, my butt, my legs, and my feet. Then she turned me over, and did my front. She massaged everything but my hair and my prick. And her avoidance of that was more than a little frustrating because while my body was flopping around like a bowl of jello, my cock was hard and raring to go.

I don't know how long it lasted. It seemed to both go on forever and yet was over in the blink of an eye.

When she stopped stroking me she said, "just take your time and relax. Only get up when you feel ok to do so."

My eyes remained closed and I floated along. Even my dick started to relax. Only a little, though. After awhile I thought I was ready to see what else we could do this evening. I opened my eyes slowly and saw some movement out of the corner of my eye. A naked Jaycee was sitting in a chair by the bed fingering herself while tugging on one of her nipples. My cock sprang back to full life so fast it looked like a catapult launching. I sat up and got off the massage table.

"Thank God," Jaycee spluttered. She lunged at the bed and shoved the table off the other side. She then grabbed me and maneuvered me so that I was again lying on my back, this time on the mattress. She threw her right leg over me, raised up on her knees, grabbed my cock, and pointed it to her. After spending all of a few seconds adjusting, "OORUMPH!" she exhaled as she impaled herself on me.

Jaycee began frantically riding me. She seemed desperate to get off. While I, as a result of my massage, had almost entered a zen-like state. I was completely calm and relaxed, except for the cock that Jaycee was riding for all she was worth. I rubbed her thighs for awhile, then her sides, and finally her breasts. Jaycee groaned when I did that, and soon positioned her tits within easy reach of my mouth. I granted her request and began sucking. She made an open mouth groan and really started grinding herself down onto me.

"Oh Will, Oh Will, Oh Will," she chanted, while grabbing me by the hair. "I'm gonna, I'm gonna, I'm gonna ... CUM!" I nibbled and bit her nipples while she shook above me. All too soon she collapsed, with me getting my head away and over her right shoulder quickly before it got stuck beneath her.

"That was so good," Jaycee mumbled. Now her body felt like a boneless mass on top of me.

I slowly stroked my fingertips up and down her back, then up and down her thighs which were still bent up towards me and hugging my sides, then back to long strokes on her back. As Jaycee relaxed, my strength was slowly returning. I started giving her little kisses on her shoulder and neck, while my strokes on her back got a little faster and firmer.

"MMmmm, that's nice," Jaycee murmured.

Jaycee had just used me as a masturbation toy. Now it was time I returned the favor. I put my right hand on the back of her head and placed the rest of that arm across her upper back, pressing her down to me. With my left hand I lengthened my last stroke on her back all the way down to her ass and then pressed firmly down there as well.

"MMmmrrmmm," Jaycee groaned in approval.

I bent my knees until I could place my feet flat on the mattress. Then pushed against it as leverage to thrust my hips upward, penetrating my cock further into the relaxing Jaycee.

"Oh! You're still hard? Oh! ... Oh!" she cried. I worked to control my pace. It felt like I could last a while.

"Will, I ... Ugh! ... I ... Umrph! ... Oh! ... Ple ... MmMm ...PLEEeeeEEEeeeEASE! ..."

My torso being all slicked up from the massage oil meant that Jaycee moved up and down over me incredibly easily. My chest was practically a frictionless surface.

"WILL!!! ... OH!!! ... PLEASE!!! ... OH!!! ..."

I tightened my grip in her hair and sucked on her neck. "RRRUUUU!!! ..." she called.

After a few minutes I could feel Jaycee's pussy contracting. I was glad to feel she was taking rule number two to heart. Another minute later I increased the pace slightly. Jaycee had stopped groaning with every thrust, but she was gasping for breath in time to my movements.

I increased my pace again.

"OOOHHHHHH COME IN ME!!!" Jaycee yelled. And I felt her pussy convulse again.

"Who does this body belong to?" I asked her into her ear.

"OOHHH!!!"

"Huh? Who does this body belong to?" I repeated.

"YOU! WILL! YOU!"

"And I can take my pleasure from it?" I asked, still keeping the rhythm of my thrusts.

"YES! TAKE IT! USE IT!"

I moved my left hand on her ass down a little bit, and touched the pucker of her asshole with the pad of my middle finger.

"And who does this ass belong to?" I asked.

"AEIEOH!" she screamed, and reflexively tried to jump up. I had too strong a grip on her upper body for it to go anywhere, but she got her ass about two to three inches up in the air, which was great. She just gave me more room for my long strokes, which I took advantage of.

Jaycee let out a loud and long moan. I was really letting her have it now. I had great leverage to move my full length out until just the head was in, then send my cock crashing back into her until it was fully sheathed and pressing against her cervix.

"Who owns this ass?" I asked again into her ear.

"MY MASTERRRRRRR!!!" she yelled out.

"And who is your master?" I asked.

"YOU! WILLIAM! MASTER!" Jaycee cried.

I removed my hand from her ass, but she stayed in place, still letting me pound away from underneath her. I reached to the nightstand with my left hand for one of her massage oil bottles, grabbing one that had the flip top still up. I upended it, and squeezed some of the slippery liquid down into the crease between her butt cheeks. Knowing I couldn't control my movement enough to replace the bottle on the stand, I just tossed it off the side of the bed. I moved my left middle finger again into that tight crevice, slicking my digit as it went. Making sure I spread the rest of my hand across the middle of her behind, I pressed the middle finger up against her asshole, and then through.

"OOOOOHHHHHHHHHHHHHHHHH!!!!!!!!!!!!!!!!" she screamed, while clenching her ass and trying to buck me off. I held her down firmly, trying to maintain the rhythm of my movement, and patiently waited for her to unclench. After about fifteen seconds she did, and I quickly pushed my finger further inside before she tightened back up. All the while I was still fucking her pussy at a steady and strong pace.

"WILL? WILL? WILL?!?" she cried.

"SShhhh!!!" I soothed. "You're doing great. Relax."

"Huh! Huh! Huh!" she grunted, then unclenched again. My oiled finger burrowed even further inside, and this time her clenches came in spurts. Within seconds I got my finger buried past the second knuckle. While Jaycee's ass was loosening, her shoulders and torso were as stiff as a board. I gave her neck a little bite, then slowly pulled my finger almost all the way out. Her ass was tight, but the massage oil was doing its trick. I quickly set up a counter-rhythm, pushing my finger in as my cock pulled out, then vice versa. I was getting close too. Those feelings of bliss were slowly building.

"Hrur! Hrur! Hrur! Hrur! Hrur!" She gritted out between clinched teeth in time to the double-thrusts. She suddenly thrust her stomach down onto me while all the tension in her shoulders released and she gasped a breath.

"SO FULL!" she wailed. "I'VE NEVER ... NEVER ... OOOOHHHHHH!!!!!!!"

I was steaming home, building the pace up even further. Jaycee was now moving with the rhythm, her body naturally flowing in an undulating pattern that pressed against my body in time to both penetrations. I shifted my hand on the back of Jaycee's head to grab a bunch of her hair. I used it to turn her face to me and jammed my tongue as far down her throat as I could get it. She kissed me back, but couldn't concentrate much on it. She was back to an irregular grunting, this time with a high pitched and staccato keening.

The pressure built and built. The time had come. I released her from my kiss and moved her head to the side. I whispered into her ear "MINE!" then bit her neck, all while shoving my hips skyward, penetrating her pussy fully. I was also pressing down hard with my left hand on her ass and pushing my middle finger as far inside as I could. And I screamed into the delicate and smooth skin that enveloped my teeth.

Jaycee came with me.

That really doesn't sell it properly.

Jaycee violently convulsed on top of me. Her whole body clenched, squeezing both my cock and finger. But the only sound she made was a quick, incredibly high pitched squeak.

My cum shot up like my dick was a fire hose. Though I doubt I had much cum after the last twenty four hours, my dick didn't seem to care. My ass squeezed a strong pulse to help send my cum on its way. With each contraction my dick spasmed inside of Jaycee and her pussy rippled all around. This went on, and on. Ten contractions? Fifteen? Twenty? I have no idea. Longer than it seemed possible. Far longer than my balls could adequately supply sperm to support. And Jaycee stayed clenched and rippling throughout.

When my hips collapsed back onto the mattress, the air just whooshed out of my lungs. Jaycee stopped holding her breath and started sucking in huge lungfuls of air. Her sphincter pushed my finger out of her ass just as easy as you please. My heart was racing, I couldn't get enough oxygen to say a word, and my muscles felt like I had just run a marathon.

Orgasms are so bizarre. One minute I felt like I was an athletic machine, then just seconds later I was so wrung out I didn't have the energy to lift a finger. A chainsaw wielding mass murderer could have burst into the room at that moment and I'd have just stared dully at him.

Jaycee moved slightly off of me to my right, allowing air to rush in between our sticky, sweaty bodies. As we gasped for breath, Jaycee turned her head towards my face, and placed her hands on me. She looked at me wonderingly, and kept changing where she put her hands, one minute on my chest, the next my cheek, then my shoulder.

"Are you for real?" she whispered in between breaths.

I guess I had enough energy for a smile. That was it, though, as I proceeded to close my eyes and lull my head back.

Slowly ... very, very slowly, our breathing returned to normal.

"I can't ... believe ..." Jaycee started, "I'm going to take another shower today."

"HA!" I laughed. "Yes, I definitely need that."

But we didn't take a shower. Instead, I filled my garden tub, and we both soaked away all the physical manifestations of our lovemaking. From there we got under the covers of my bed, ready for sleep. All throughout we didn't go more than a minute without maintaining physical contact. I don't know if it was a need to touch each other, or a desire. Not a sexual desire, but something more than just a mere transient want. We barely spoke to each other. We didn't need to. Something special had happened. And neither of us wanted to talk of mundane things that would detract from what we had experienced and were still feeling.

When we were in bed, I lay on my right side, Jaycee on her left. We were facing each other, but somehow we found a comfortable position where our arms and legs were intertwined. Our faces were just an inch apart, and we could gaze at each other, and feel our breath caress the other's lips. All I had to do was move my head the smallest amount to kiss her, which I did several times.

When I was drifting off to sleep, the last thing I heard was Jaycee whisper, "Yours."