Side Bet Bluff Ch. 06

"You've got another punishment coming, haven't you?" I asked.

"Oh!" squeaked Jaycee. Her head bent down a bit. "Yes, Master," she said.

I grabbed the sides of her panties and pulled them down her legs. Jaycee alternately raised her feet to allow their full removal.

"Bend over. Put yourself face down onto the bed," I ordered. "Spread your legs," I added. Jaycee moved her feet about a foot apart. "More." Now they were about two feet apart. "Good."

"I'm not sure I like being in this position without feeling your body beneath me," Jaycee admitted.

"Oh?" I responded. "How come? Why is this so different?"

"I liked that I could feel your excitement when you spanked me," Jaycee said. "I always pressed against you so that I could feel your cock along my left side."

So she needs to feel my cock, does she? I took off my pants and underwear in one motion; my cock springing forward, ready for its target. I knelt down and placed my hands on the back of Jaycee's ankles. Then I slowly slid them up the back of her legs, enjoying the feel and look of them encased in the unusually patterned thigh high stockings. When I came to her bare skin, I moved my hands out to the sides, stroking her upper thighs to the side, and then back. Jaycee widened her legs more, giving me greater access.

"What did you do to get this coming punishment?" I asked her as I moved my hands up to her bare ass.

"I teased Allison sexually after you told me not to," Jaycee answered, in a less than even voice. She really tensed up as I touched her behind. That's disappointing. I thought we had made such great progress.

"Do you think you deserve this punishment?" I asked her, and I moved my hands up her back, up over the grey camisole.

"I deserve anything my Master decides to give me," Jaycee said. Her words countering her body's tension.

"I like that answer, Jaycee," I said, leaning far forward to push my fingers through her hair. "In fact, this punishment is going to be a little different from the others. I don't want you to count this time. Because I'm not sure how many times I'm going to smack that wonderful ass of yours."

"Yes, Master," Jaycee said. She sounded a little pitiful, but I could tell she was still very turned on, in spite of her tension. I lined my cock up with her pussy and slowly pushed in.

"OH! SIR!" a surprised Jaycee emitted.

I eased out quickly, making for a very shallow stroke, then reversed course again. I kept my strokes shallow but ever so slowly deepening. I hadn't met any strong resistance so far and I wanted to keep it that way. Jaycee immediately relaxed into the bed and began groaning beneath me. She wasn't in much of a position to move with me since her legs were right up against the side of the bed. I pressed down on her lower back to keep her immobilized while I continued to fuck her.

After a couple minutes I still had only half my cock inside her. Jaycee would try to move backwards to force more of me into her but I wouldn't let her speed up this process. The tension in her butt and her stomach slowly returned as a result.

"Please, Sir, you're torturing me."

I smiled but didn't change my strategy. This was Jaycee's first time with doggy style and I didn't want to ruin it. I knew I could get deeper penetration than usual in this position and the one time the uptight and repressed Hannah had let me try it she had screamed bloody murder when I jammed it in too quickly and stabbed her cervix hard with my dick. With Jaycee, I was determined to go real slow, teasing her and slowly working her up. Maybe I could use this as a way of reinforcing my control over her. That is, so long as I kept control over myself.

Another minute and I was now three-quarters in. Jaycee was now whimpering beneath me.

"Please!" she screamed out. Her pussy was tightly clenching my dick. The effect on me was pronounced and I was in serious danger of getting overly stimulated. I pulled out completely and positioned myself to her side while still keeping weight on the small of her back to keep her in place.

[SMACK!] went my hand on her behind. I hadn't originally intended to spank her. I had thought I would be cute and 'spank' her with my entire body against her ass as I strongly pumped in and out of her. But I needed a break and the promise of a spank was a good excuse. I gave her two more hard swats, just because I could.

I took three deep breaths and then resumed my earlier position. Only I seemed to go in even further on my first stroke. I found my earlier rhythm quickly and within a few strokes felt myself pressing against her cervix. Jaycee groaned and arched her back strongly. That changed my angle slightly so that, although I was still rubbing on the same spot, now I was gliding along it while still going a little further inside. Jaycee held herself in that position for a good five or six strokes as my penetration became progressively easier. As soon as I was fully sheathed within her, she collapsed. My dick pressed tightly against her. I wasn't sure I could pull out. I felt momentarily trapped by her cunt.

"Gurghjiggl," Jaycee emitted.

I repositioned my hands on her ass cheeks for leverage and slowly pulled myself back. Jaycee instantly stiffened. Her hands clawed at the sheets. This new angle made the going slow as it felt like my dick was wanting to point straight up but was instead being forced horizontal by the shape of her pussy. As I got near to her entrance I worried about accidently popping out and slowed to a crawl to keep the tip inside.

When it was time for a new inward stroke, my hands gripped Jaycee's ass and I started pushing back in. Jaycee suddenly sank into the bed a little more. Confused, I looked down only to see that she had taken her feet up from the floor and her legs were shaking. I continued my inward progress and her legs started kicking the air to either side of me. I looked back to the bed and Jaycee had her arms suspended in the air with her hands as fists like she wanted to punch something but was holding herself back. As I got fully ensheathed, her back arched again and a little "Eep!" escaped from her mouth. Her hands and legs both dropped back down, hands to the mattress and feet awkwardly hitting the floor.

I pulled back again, a little quicker this time, using my grip on her behind to keep her in place. Jaycee again arched her back as she gurgled a noise that was part whimper, part groan. As I came to a halt just inside of her, she pounded the mattress with her right hand. I could also feel her legs vibrating on either side of me. As I reversed direction, moving much faster within her, I realized why she was acting this way. I was holding onto her ass, that beloved part of her that had produced such violent reactions against her former lovers. I guessed that while she had gotten used to one form of touching, i.e. spanking, I had never firmly gripped her like this before, and she was reacting against it but fighting to control it.

I was just going to have to give her something else to concentrate on. She was loose enough for me to pick up the pace, so I did. Still gripping her ass cheeks, I increased my tempo while maintaining the length of my strokes, the tip of my head pushing against the firm face of her cervix. I focused my eyes on Jaycee's cute little dimples where her behind met her back.

"Yes, yes," Jaycee murmured. My tempo continued to increase. Now the contact my hips made with Jaycee's rear became audible, thanks to the violence of our motions and the emergence of a light sheen of sweat. I was finally engaging in my intended 'punishment' of Jaycee, spanking her ass with my entire body.

Jaycee was slowly pushed further onto the bed by my thrusts, to the point where it was becoming difficult to maintain my hold. I let go of her ass cheeks, repositioned my hands on her hips, and dragged her back to the edge of the mattress. Jaycee moaned strongly as her stimulated nipples brushed against the sheets.

With this new handhold I had better leverage to really start ramming her, yet Jaycee seemed more relaxed. The tension in her frame was lessening. Ah yes, I was no longer engaging her phobia. I didn't want her sliding up the bed again, but I wanted to re-engage that tension. What to do? I had better think of something fast, because I wasn't going to be able to last much longer, not with Jaycee's pussy gripping my cock like it was. I reached up and placed a hand on her shoulder, but after a few strokes I couldn't tell any difference.

I pulled out, took a step back and commanded, "Jaycee, grab your ass cheeks!"

"Wh-What?" she asked, confused.

[SMACK!] I spanked. "Do it now. Grab your ass cheeks."

Jaycee reached back and placed her hands on her bottom.

"Now pull them apart. Let me fully see you."

Jaycee hesitated. I moved my hand back to give her another spank when her hands slowly began moving outwards. While her hands moved a few inches apart, they hadn't gone far enough for me to see anything.

"More," I commanded.

Jaycee whimpered again, but pulled her cheeks further apart, this time showing me her hidden and sensitive little star.

"Good girl," I said soothingly.

"Will, I'm not ready yet," she began but stopped when I placed my hands on top of hers, pulling them even wider. Now she was really stretched, with her pucker even slightly gaping open.

But I wasn't going to try anal with Jaycee tonight. I wanted to prep her first. This was merely to keep her off balance. Instead I lined back up with her pussy and slid in.

"Ohherrour," came from Jaycee. Was that a sigh or a moan?

I quickly returned to a fast pace while trying to maintain my hold on Jaycee's hand-covered rear. I wasn't all that successful, but the importance was keeping Jaycee both stimulated and feeling vulnerable. I kept at that as long as I could, but I didn't have a firm enough grip on her to really keep the pace I wanted.

"Keep yourself stretched," I told her and then removed my hands. I used my right hand to grab her waist and brought her more fully downward as I impaled her, penetrating her deeply and more quickly. I snaked my left hand underneath her from the left until I could feel her clit. It was an awkward position for me, forcing me to hunch over her, but I could still get full penetration and power. As I rubbed Jaycee's button, she went nuts. Her hips began bouncing up off the bed while her pussy vibrated with need. I desperately tried to maintain control, but it was a losing battle. As I could feel my orgasm approaching, I let go of Jaycee with my right hand and placed my thumb right up against her asshole. I used the palm of my right hand to hold her in place. Still rubbing Jaycee from below, I pushed all the way in and let loose.

"Hai-eek-ay," said Jaycee as her body locked in place, fully tensed while my cock surged within her.

As my orgasm concluded, my body went limp and I collapsed over Jaycee's back. I could still feel Jaycee's pussy trying to hold on to my dick as it slowly lost its rigidity. This provoked occasional reactions from my cock, which would spasm in an attempt to shoot some now non-existent cum further into her. Jaycee would jump in response to that, but her pussy would go right back to trying to milk and grip me. After a few minutes, I finally slipped out of her, though still gasping for breath while sprawled out over her back. My weight pressed her down but I still had plenty of contact with the bed as well.

Feeling the slickness of her skin, the movement of her lungs, and the occasional twitch and vibration of used muscles, I was struck at how different sex with Jaycee was from everyone else I'd been with. As I've mentioned earlier, I haven't had many lovers. My first serious girlfriend had been an on again, off again relationship where I had picked up some very bad habits. Those had complicated my two short relationships in college. My long relationship with Hannah hadn't really helped things much. Though one thing I had developed with Hannah was staying power. But I had always thought that was mostly from boredom.

When Hannah had been in the mood, she would insist on riding cowgirl, and would bring herself to a powerful orgasm, usually bringing me right along with her. But those times were few and far between. For the most part, Hannah thought that we should have sex at least once every five days. If it went beyond that, then she would get paranoid and think I wasn't interested in her any more or must be getting sex somewhere else. So she would instigate sex, but merely out of what she saw as a necessary act to keep me, rather than any romantic or even physical desire. I was then expected to get turned on and fuck her while she just lay there with her legs spread, patiently waiting for me to get myself off. A number of times with Hannah I had lost my erection before I had cum, simply from lack of stimulation. In the back of my head, I had always thought that if I were truly excited, then I would cum quickly.

Yet I was disproving that to myself each time I was with Jaycee. Sometimes I was very conscious of my body's attempt to cum to completion, and willed myself to hold off. I was now rather pleased with, well, everything about our lovemaking so far.

I had originally told Jaycee that I would need her to help me become a better lover, but instead things seemed to flow very naturally. Almost all of my actions were a direct result of the things I swore to change as a result of how I was with Hannah. That seemed to be working. Even being able to fully enter Jaycee during that first time together seemed like another serendipitous piece to the puzzle of how she and I just clicked. In fact, from Jaycee's perspective, it probably reinforced my being her master. I mean, I seemed to be able to give her pleasure while projecting an image of control over not only her but myself. Did that give her an excuse to acquiesce in this master/slave role-play we were doing? Or was her pleasure enhanced, or maybe even solely derived from that image of control? Just how much of this was physical and how much psychological? And could there be one without the other?

Ah, the questions that pop into my head when my body has shut down. Maybe I'd have a better perspective after a night of dreaming.

I slowly pulled myself up towards the head of the bed, giving Jaycee a kiss on her forehead along the way. I decided to forego the bathroom trip to clean myself. Sleep beckoned me. Even with Jaycee weighing down the covers on the lower half of the bed I managed to pull the sheets back enough to crawl under.

After a few minutes I heard Jaycee get up and use the bathroom. She came back with a warm washcloth and washed me down. I was so comfortable that I didn't even bother to open my eyes, though I think I sighed appreciatively.

"That was exactly what I needed," she softly whispered.

My consciousness faded into sleep.

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I'd like to thank Erik Thread and DisMan for taking the time to edit this chapter. Their expertise in grammar and proofreading vastly exceed my own. Any remaining errors were most likely left intentionally by me for stylistic reasons.