Shared Fantasies Ch. 05


Damn it, I had indeed outsmarted myself. I was positive the last thing she would have chosen would be mouth. Jess was one step ahead of me, as usual!

"Relax, I'll be back in a while," she said as she sauntered out of the room.

The entire time she was gone I concentrated on trying to figure out which of the three to choose the next time. I knew I was outthinking myself, and that I was probably better off just picking one at random, but I couldn't help it.

It seemed like forever before she returned, but knowing Jessie I'm sure it had been exactly one hour.

"Ready to try again?" she asked, way to cheerfully for my mood.

"Yes!" I replied, preying that my ordeal was about to end.

She picked up the pad and wrote and then looked at me, "Well, what's your pick this time?"

"Pussy!" I said confidently. I assumed I figured how she would think this through.

"You really want to cum inside me, don't you?" she said with a big grin.

"Okay, let's see if you're right this time."

This second time she was far more brutal than the first. The first time she'd just given me a slow but steady fuck until I was very near the edge. The second time she was much more creative. She started by taking my cock in her hand and sliding just the tip back and forth the length of her slit. She kept that up quite a while. It was a very maddening sensation, but did little to bring my closer to orgasm.

Next she used my cock as if it were a dildo. She flicked it back and forth and rubbed it against her clit, giving herself some very good stimulation while denying me much at all. Finally she slowly lowered herself onto my pole until all of me was buried inside her.

"Mmm, you are certainly big and hard" she said dreamily. It was obvious that her early actions had her climbing toward another orgasm much more than she had done to me yet. At first she was performing the same torturously slow, steady fucking she'd done before, but after just a little bit of that and while I was still far from cumming, she lowered herself all the way down on me and started just rocking back and forth. I immediately realized she was rubbing her clit against my pubic bone and giving herself some very intense stimulation while giving me very little yet again.

"Mmm, God that feels good. Oh yeah, this is going to work much better!" she moaned, her eyes starting to turn glassy.

She'd discovered a way that she could get off on my cock, which I know she loves, without having to really pay much attention to keep me from going over the edge. She'd stop the rocking and start the slow pumping again every few minutes until I'd get close, but not dangerously so and then she'd go back to grinding her clit on my bone.

It took about four cycles of this before she exploded in a shuddering orgasm. The feeling of her pussy pulsing and spasming around my dick was extremely frustrating as you can imagine. As soon as her orgasm passed she began the slow fucking again.

Able to concentrate more fully, she pushed me much closer before stopping. While she let me back off a little she would squeeze her cunt muscles as hard as she could, causing my cock to twitch violently inside her. She sat up each time she did this so she could reach behind her and massage my balls too.

"Jessie, PLEASE, for God's sake I can't take any more! PLEASE! I REALLY CAN'T STAND ANY MORE!" I was begging non-stop. I really had reached my limit and felt I was about to croak or something.

"Okay, you finally ready?" she whispered gently right in my ear.

"GOD YES, PLEASE!" I shouted.

"Cum baby, cum hard!" she whispered again as she started to pump my cock in and out of her slippery love box. She was going at a nice steady pace, not slow like before.

I raced toward orgasm. My arms and legs straining against the restraints as my whole body tensed in anticipation.

I felt my balls start to contract and my cock swell in the final seconds. So did Jess and as she did she lifted her hips enough so my cock once again slapped down on my stomach and just lay there twitching and jerking, but not cumming!

"NOOO! YOU CAN'T! OH GOD NO!" I really was screaming.

She just looked down at me a chuckled, "I bet you actually thought you were going to get to cum at last, huh?"

"Oh God Jess, PLEASE! I really, really can't stand any more. Please make me cum now!" I begged.

"You know Jack, I think you're telling the truth. I really don't think you can take any more either!" she said evenly.

"Oh God, thank you, thank you!" I said with obvious joy and relief that this was coming to an end at last. At that instant I really wondered why in the HELL I had ever gotten myself into such a mess.

Then Jessie dropped a bombshell, "BUT, what you said you wanted was, and I quote, 'do it over and over until you can't stand any more, then do it some more anyway.' And since you are finally at the point where you can't stand any more I now have to do it some more anyway, right?"

"OH GOD NO Jess! I never imagined it would be like this, please!" I begged some more.

"I seem to remember telling you exactly that, but you said this was what you wanted anyway. Remember you told me you wanted me be to be a merciless cock teasing bitch," she said in a deadly serious manner.

Of course, as always, Jessie remembered exactly what I'd said with perfect accuracy. I realized I'd set myself up to be totally fucked and now that was exactly what Jess was going to do.

"In fact, since your fantasy includes more teasing after you can't stand it, I can't let you cum until you receive quite a bit more teasing. With the luck you're having so far today it probably wouldn't matter anyway, but you don't get another chance to guess correctly until I've given you at least three more teasing sessions. Heck, maybe I'll just keep teasing you all day and never let you cum," she said in way to cheerier a manner for my liking.

"But Jess, you can't! You promised to make me cum today!" I implored, my confidence that Jessie wouldn't break her promise wavering.

She laughed at that, "Oh no I didn't. That's what you asked me to promise, but you didn't listen carefully enough when I made the promise. I said 'I promise that I won't make you cum before tomorrow, which meant today, under any circumstances. But I left out the part you asked me to include about definitely making you cum today. I've already fulfilled my promise and I still don't have to let you cum. So you better be real nice to me!"

I thought hard! I honestly couldn't remember exactly what Jess had promised, but I was sure that she now felt she had the choice of making me wait another day or even longer before letting me cum. I was devastated.

"Now rest for a while, I'll be back soon." And with that she left the room.

I realized that Jessie had somehow rigged my guessing earlier in the day. I didn't know how, but it was clear that she had never intended to let me cum yet. She'd been planning all along to keep teasing me even after I really couldn't take any more. It was obvious to both of us that I'd reached that point. That she was going to continue to drive me wild for God knew how long was unthinkable to me. The possibility that she wasn't going to let me cum at all that day had just become very real to me. I thought I might actually cry.

'A while' turned out to be rather short. It wasn't long at all before Jess was back kneeling between my legs, and toying with my cock. She rotated through her entire bag of tricks almost non-stop for a very long time. I'm positive that marathon session must have lasted at least two hours. When she did have to stop to keep me from cumming, she employed her ball massaging techniques, except of course during the occasional break to sit on my face and have me lick her to yet another orgasm!

Near the end of that particular session she engaged in some heavy verbal teasing too, which she seemed to enjoy immensely as well.

Things like, "God Jack, your balls are unbelievably swollen and the veins on your cock look like they are about to burst. I don't know how you can stand this. You must need to cum so bad by now I can't imagine what it's like!"

And then with a giggle she added, "But you aren't going to for a long, long time"

Her good nature and giggling as she said these things made it all the worse.

I began to feel like I really was slowly loosing my mind. The ache was indeed extreme. My cock was so sensitive that her touches felt electric. She'd become so skillful that I constantly felt like my orgasm was just a second or two away and any further stimulation whatsoever would push me over the edge, but still she kept me from that final achievement.

It was well into the afternoon when Jessie finally gave me a rest. I was emotionally drained and physically in desperate need of being drained, if you know what I mean! Jess was giving me way, way more than I'd bargained for and I was absolutely regretting having gone through with my fantasy, just as she had predicted.

I think I must have dozed off again because I had no sense of how long Jessie had been gone when I realized she was in the room again.

I knew I really, really couldn't stand any more.

I started to beg in earnest, "PLEASE Jess, no more! PLEASE! I really can't stand any more; I can't take any more. You have to stop teasing me like this and let me cum, PLEASE; I'm really begging you! PLEASE!"

She looked at me and a grin spread across her face, "Oh sure you can! You do need to cum very, very badly I know, but you can take some more teasing first. Just like you fantasized about all this time. Here let me show you!"

And with that she crawled up onto the bed and started to suck and lick my cock and balls. She was doing it excruciatingly soft and slow; still it took only seconds before I was right at the edge yet again.

"NO! God no! PLEASE MAKE ME CUM!" I yelled.

"Mmmh mmh" she moaned around my cock as she shook her head just a little from side to side.

The sensation of her vocalization was amazing and nearly put me over the edge. It was clear, however that she didn't intend for that to happen.

She went on giving me the lightest, most teasing blowjob I'd ever experienced, making it last for a long time. Finally I was at the point where any more stimulation would have me spurting. My balls tightened and my cock started to spasm. I was thrusting my hips as much as I could, which wasn't much. I knew she was just an instant away from stopping again.

However to my amazement she didn't stop. She just kept up that very light licking and sucking. It was too much, my whole body started to shake as the first shot of cum erupted from the tip of my cock. Just as it started Jess began sucking hard and fast, her head bobbing up and down quickly, her lips wrapped tight around my shaft. She took me deep in her throat until her lips were at the very base of my cock and then slid them up the shaft until just the head was still in her mouth. Back and forth she made the trip as rapidly as she could. She was sucking and swallowing for all she was worth too!

Shot after shot of my jizz kept spewing from my cock. My body continued to shake violently. Jess just kept at it while I experienced the most massive and intense orgasm of my entire life. She tried valiantly to swallow every drop, but it was simply impossible. The volume was far too great and some was running out the corners of her mouth.

It seemed as if I would go on shooting cum forever. I don't know how long it was before she stopped as I lapsed into a daze at some point. Nor do I know how long it took before I regained my senses, but when I did I looked up to a huge smile on that gorgeous face and saw cum running down her chin and dripping onto her luscious tits.

Once I was more or less recovered Jess quickly released my restraints and lay down next to me, wrapping her arms around me. I was too wasted to even move.

After a while Jessie started to stroke my cock again. It was not the teasing kind of strokes she'd been giving it for the past couple of days, but rather the kind intended to get me hard and ready to fuck. Somewhat to my surprise she was getting a response much sooner than would normally be the case given how recently I had cum, but things were still a long way from normal.

It wasn't long before I was ready and Jessie wasted no time climbing on top and slipping my cock in her very wet snatch. Her on top is a position we both enjoy greatly, but for some reason one we just don't do all that often. She began a nice steady pace, rocking her pelvis in a way that stimulates the head of my cock more than when I'm on top.

The sensation of Jess fucking me was quite intense, given how sensitive my cock was from the treatment it had received. Intense, but wonderful! And again in much less time than normal after such a recent orgasm, I was right on the verge. Jess sensed this and increased the pace while contracting her cunt muscles at the same time. That did it and I blasted off for the second time. She dept it up until my balls were thoroughly drained and my cock was mostly soft. It wasn't as intense as the orgasm her earlier blow job had produced, but it was still about a 9.9 on a scale of 10.

We just cuddled for a while and I dozed off again. I was physically and emotionally exhausted after the ordeal that had started on Friday night. Really it started over a week earlier I realized.

When we woke we took a shower together and played around a bit, but it was only that. No more cumming.

After a light, and quiet dinner we went off to bed. I licked Jess to a serious orgasm while she sucked and toyed with my cock, but not enough to bring me off. She wanted a 'real' lovemaking sessions she said. And that's exactly what she got. Not the wild animal sex of earlier in the day, but slow and tender and intimate. We were both quite satisfied afterwards.

Only then did we discuss my fantasy. She asked if it was what I wanted and I admitted she'd been right. It had been what I asked for, but turned out to be far more than I wanted. I acknowledged she had not gone beyond what I'd described, but again admitted it was much more intense than I could possibly have anticipated. We both commented on how when I did finally cum it was the most violent and intense orgasm ever.

Jessie acknowledged that she had enjoyed it far more than she ever dreamed.

Jessie asked me if I was sorry we'd done it. I had to reflect for a moment, but said I wasn't, because I would always have wondered if we hadn't.

She also asked if I wanted to repeat my fantasy ever. I thought even longer on that one, but in the end said "Maybe someday I might considerate, but no time soon, that's for sure."

Our conversation wound up with her asking if she got to choose the next fantasy we acted out. Of course I said yes, that was our original deal that we'd alternate picking what it would be.

At that point we kissed and hugged and snuggled down to go to sleep.

I was just nodding off when Jess whispered in my ear, "Jack, what if my fantasy was to repeat this weekend?"

I just groaned by way of response, but I could tell she was serious. I was also surprised to feel a bit of a twitch in my crotch!

The End

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