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To Sir with Love - Part 3, The Challenge

YourPebbles

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Suddenly, my head and back arched violently. What the fuck was that?? Holy shit… cold! Cold!! I cried out, knowing I was deeply excited, but it sounded like I was in terrible pain as the icy water dripped down on me from above. My brain could not decipher fast enough between pleasure and pain. Everything became a bur. I sensed him untying my hands, and then in what seemed only an instant, he was behind me, lifting my shoulders and torso so that I was kneeling upright now.

With one arm wrapped around my waist, his other hand found my lips with an ice cube. I licked it, as my mouth desperately needed moisture. His mouth was close, just behind my right ear, and as he allowed me to suck the cube in and out as he held it, I could hear the rhythm of his breath change ever so slightly and I knew it pleased him to watch. He was the total opposite of me. Always cool, calm, composed, and in control. And I was clearly a hot, trembling, verbal mess. But I knew he liked it. He liked that he could reduce me to a puddle of cum in no time, and sometimes with just a word. But at this moment, I was loving knowing that I was exciting him so much.

And as if being cued, I felt his rock-hard cock press against my buttocks. I hadn’t realized he had removed his boxer shorts, but this discovery delighted me so much. It must almost be time for us to have sex. Yippee! I couldn’t wait for him to penetrate me, to make me cum over and over again all night. I started to reach a hand back to touch him, but he firmly said, “No, Pebbles. You do not have permission to touch me.” Dejected, I fantasized about touching him, sucking him. My pelvis started to rock and thrust, and as I was lost in thought, I hadn’t realized that the ice cube had disintegrated and I was now starting to suck Jay’s fingers. I heard a soft moan from behind my ear, and then he pulled his hand away sharply.

I whimpered, “Sorry, Sir,” only to feel a sharp squeeze on one nipple, and an icy cold sensation on the other. As he traced another ice cube around my breasts and up my center, from my jawline down to my pubic bone, drips of icy water clustered on and trickled down through my neatly trimmed bush. One drop rolled down my clit and my back arched and I gasped loudly, and instinctively thrust my backside hard against his organ. He pushed me away and forcefully bent me back over the bench. And with no warning, he thrust his cock into me and his balls slapped hard into my clit. I was in heaven - for a second. Then as quickly as it went in, he pulled it out.

Mother fucker!! How could he? How dare he??

Then I got it, I understood. This was my real punishment. Orgasm control.

The only solace I took was in the tiny bit of audible sound that finally came out of him as he pulled out, or as he tried to pull out. My pussy was so primed and ready, that the second he went in, it grabbed him so tightly, it actually required a little effort on his part to pull back out. I was sure that with one more thrust, both of us would have been cumming.

And I must have been dead on with his need for release, because he stood up and asked teasingly, and maybe with the slightest hint of aggression, “Are you still thirsty, Pebbles?” He pulled me up to kneeling again as I answered, “Yes, Sir.” I heard the clinking of more ice and suddenly my lips were being traced with another ice cube. Although this time, every time I tried to suck it in, he pulled it away, teasing me. Then, I felt something warm and wet on my lips. A smile spread across my face as I realized what it was. He tickled my lips, cheeks and jaw with the tip of his dick, still wet with me. I licked my juices off my lips and off him, happy knowing I tasted good for him (should his mouth ever find my pussy!!). Then he gently cradled my head in one hand, and with the other, guided his throbbing penis into my mouth.

He was not expecting me to cum again right then, but I think he underestimated how turned on it made me to orally satisfy my man. I got off on it, and this time would be no exception. I felt badly though, as I couldn’t quite blow him right while I was breathless mid-orgasm. I tried to regain my senses quickly so I could please him the way he wanted to be pleased, the way he needed to be pleased, the way he deserved to be pleased.

Finally I was back, and I redirected my attention to him, to his penis. My wet lips wrapped around it, and I took him deep into my throat. Since my hands were free, I could support myself on the bench and keep myself in a solid position, and just push myself up and down to move my lips along his stiffened shaft. I grabbed and tugged at his balls, and since I was not scolded for using my hands, I continued that play. My tongue was in heaven! It especially liked finding the rim of his cock-head and giving it a flick ever time they came together. I could hear his breath increasing, his grip tightening on the back of my head, and I knew it would not be much longer.

Just before he came, however, he pinched my nipple so hard. I took that as his giving me permission to cum again. And so I did, at the same time he did. And although I was gasping for air, I held my lips tight around him till every drop was out of him, then I sucked it all down like I was dying of thirst. “Ummm, thank you Sir," I said, pleased to know I had given him a taste of what he'd been giving to me this whole session. He offered me a sigh of relief, and I desperately wanted to see if he was smiling.

As if he could read my mind, the blindfold came off. And it pleased me so much to see my Sir looking down at me with a sweet smile and a look of satisfaction in his eyes. "That's my Pebbles," he said, lightly stroking my cheek. He unbound the rest of me from the bench, brought me back to the bed, and laid me down face up this time. He looked at my red knees and kissed them so gently, yet seductively, that I instantly started craving his mouth.

“Kiss,” I whispered. Jay looked up at me.

“Really, Pebbles? (Lick) You really want me (lick) to stop doing (lick) what I’m doing right now?” he asked as he licked, higher and higher up my thighs, maintaining eye contact with me the entire time.

I flinched and convulsed as he added his fingers, dragging them up my leg. And even though I was free of restraints, I kept my arms out wide and I spread my legs apart further for him. He knew what I wanted. But would he give it to me?

And just as before, without warning, his mouth pounced on my pussy. I screamed loudly, my back arched, and my thighs closed in around him. My hands desperately grabbed at the bedding pulling it off from the corners of the bed.

“Fuck!” I cried out loudly, not caring if there were people in the neighboring rooms that could hear me. I let out my howls and screams of pleasure without a care. I did not care who heard me, I did not care about anything except what was happening between my legs at the moment.

And then again, he stopped.

“No, no, no, no, no, no, no!!” I begged. “Please! Please! I need you so bad. Please, please don’t stop, please! I beg you.” I felt like I was about to cry again. Although, this time for a completely different reason.

He smiled an evil grin, and I watched him reach and grab something from behind him. He moved away from me now, standing, not showing me what he was holding, but deep down I knew. My suspicions were confirmed when he ordered me to open my mouth.

“Kiss, kiss!” I cried out, pleading with him.

He ignored me as he had done earlier, not going along with my childish game, and repeated, “Open your mouth, Pebbles.”

I was desperate. “But you promised, Sir.”

And being the good Dom that he was, he knelt over me, looked deeply into my eyes, then kissed me hard. My eyes closed and rolled back in their sockets. Not because I was cumming, but because his kiss took me to some far away land. Somewhere safe again. I kept my eyes closed… and opened my mouth.

“Good girl, Pebbles,” he said, and rewarded me with one more kiss on my forehead as he gently strapped the ball gag to me. I tried to get used to it, but I didn’t care for it. Jay had told me before that he thought I would grow to like it, because it would make me more appreciative of the times I was allowed to use my mouth. (I just think he didn’t want management knocking on the door...)

“Now Pebbles”, he started, “I told you that you could not come without my permission. You did not do so well with that request, and I have gone easy on your punishment since this is your first time and you are still learning. But we will try this again, a little differently. You are to NOT STOP cumming unless I tell you to.”

I opened my eyes, in shock. What? Was that even possible? I tried to protest, but all that came out of me was some muffled, jumbled-up, illegible words. Feeling helpless, I tried to psych myself up. You can do this, you can cum easily… look how many times you’ve already cum? You’ve been capable of having multiple orgasms since you were a little girl. AND, you can bring yourself to orgasm through meditation. I took a deep breath, as deep as I could anyway around a gag in my mouth, and started feeling a little more confident in the challenge presented to me. Cumming had never been an issue for me, I decided.

But at someone else’s command? I gulped hard.

I noticed Jay had positioned some of his favorite tickle-torture toys around me, within his grasp, and was holding something else in his hands. He pinched one of my nipples hard, and a muffled scream gurgled past my gag. Then he did the same to the other, and when he got them nice and erect, he clamped each one. There was a chain running between the two clamps, which he yanked on firmly. It hurt a bit, but mostly sent electrical impulses coursing through my body, making my womanhood pulsate.

Once he had things as he wanted - toys positioned, nipples clamped, my body positioned with arms out and legs splayed open like a butterfly - he said, “You may start cumming when I tell you, and then you may not stop until I tell you. Got it, Pebbles? Oh, and don’t move."

Wait, what?? That was not part of the deal! “Unfair!” I tried to scream out, but it was useless. He sat at my side, perfectly positioned between my upper and lower body. With his lower hand, he grabbed the small vibrating tool that had inflicted so much tortuous tickling on my feet just a short while earlier. With his other hand, he grabbed a scalp massager with all its many sensory points, all at different lengths. I tried to show my approval at how well he had been paying attention over the past eight months.

He pressed the ON button, and held the tool in the crease of my pelvis. My legs flapped inward, but I somehow managed to pull them back out fairly quickly, not wanting to fail my Sir again. Then he started to run the scalp massager all over my upper torso, from my fingertips down to my bikini area, but never crossing the bikini line. Every once in a while, the scalp massager would hook the chain and give my nipples a good tug. I was in ecstasy with the bombardment of sensations raining down upon me.

And then he moved the tool to my clit, and I heard him whisper, “Now, Pebbles. Now you may cum and don’t stop until you are told.”

The command in his voice combined with the vibrations on my clit made that request a non-issue. I climaxed hard, and I think everyone in the hotel would have heard it had I not been gagged. He moved the tool in small circles around my clit, occasionally gracing over it, occasionally pressing hard onto it, and sometimes moving it down my thighs, which he realized quickly, I was helpless at keeping still any time he touched them. So the little fucker decided to focus exclusively there, taking the scalp massager with him.

He left the vibrator on my clit, as he grabbed one leg and extended it out, then straddled it to keep it still. Holding my calf firm between his legs, he ran the scalp massager up and down my right thigh. My body convulsed. This was too much. I felt drool starting to drip down my chin as I came again. And just as I started to regain my breath, he grabbed the tool, and reached it back behind him and found a crevice between my right toes. I bucked so hard I almost lifted him right up off me. I thought I could handle this, but this was something I had never experienced before. This was too much. Orgasm after orgasm Jay gave me as he had quickly moved over to repeat the same torture to the left leg. “Kiss, Kiss!” I tried yelling, but no one could have understood anything coming out of my mouth in that moment, gagged or not.

Then that sneaky bastard, that magnificent sneaky bastard, while my eyes were clenched tight mid orgasm, he thrust two fingers into me and stroked my g-spot. My back arched and I was suddenly aware that the sheets were all gathered around me, balled up in my fists. As wet and slippery as I was, he could not remove his fingers. My pussy grabbed him like a vice grip. This is what I wanted all night. Penetration. He had fucked with my mind long enough. It was time to for real fuck me!

Seeing as he was stuck there for the time being, he put his mouth on my clit again and sucked it in unison with my hips bucking up into him. When he felt me about to come again, he yanked my nipple chain. And again I came, and it was a big one. As on the bench, my body stiffened and I stopped breathing for what seemed like an eternity. And I think he knew, I could take no more.

“You may stop now, Pebbles.”

I released a sigh of relief. As my body slowly softened again, he was able to wiggle his fingers out of me. He rested his head on my tummy for a moment, kissing it softly. Then he crawled up me to remove the nipple clamps and ball gag. As he unfastened them, I was aware that I was a hot, drippy, drooly mess. I was sure my hair was a rat's nest, and my mascara was down my face, but I didn’t care. I had successfully pleased my Sir.

To be continued...

Jay's Version:
http://www.ticklingforum.com/showthread.php?317344-My-Pebbles-(M-F)
Part 1:
http://www.ticklingforum.com/showthread.php?317378-To-Sir-with-Love-Part-1-The-Backstory
Part 2:
http://www.ticklingforum.com/showthread.php?317381-To-Sir-with-Love-Part-2-Establishing-Trust
Part 4:
http://www.ticklingforum.com/showthread.php?317399-To-Sir-with-Love-Part-4-The-Conclusion
 
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Oh man, do I love part 3 of this story. There was hardly any tickling in this chapter, but it's my favorite one so far. You know how I think and what makes me tick....so much of what I love about a session is captured in here. I might have to print this out and use it as blueprint.
 
Hmmm... we will have to discuss your favorite parts then. You've got me all curious now...
 
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