Mr. Bear Ch. 3

When fully erect, he was probably a good eight to nine inches in length and probably two inches in diameter at best, a little thin compared to others of that length, but definitely above the average six-inch/in and a half male, which made him nicely proportioned to his greater size. However, right after being foreskin-tortured, he had shrunk down to the smallest I think even he had ever seen himself get, maybe--*maybe*--three shrivelled little inches, still somewhat thick, but not nearly as thick as he could get. Within twenty seconds of having his tiny member swirled around the warm, wet, soft interior of my mouth, playing its limp state over and around the supple, gentle strength of my tongue, he had definitely surpassed the three inch mark.

Ten seconds after that, he was as large as I could maintain whole in my mouth without gagging, which was about four inches. As he outgrew what I could comfortably take without having to try and subdue my sensitive gag-reflex in an attempt to deep-throat him—something I simply couldn't do easily, even back in my old submissive days—I started bobbing my head toward and away from his balls, slipping my lips down and up his shaft in a rhythmic caress.

In apology for the shrivelling agony he had suffered, I made sure to play my tongue lightly but thoroughly over the upper side of his foreskin, around and over the spot where I had applied the clothespin, using the very soft, nearly textureless underside of my tongue. Occasionally I would stop bobbing my head long enough to suck on the head and foreskin region of his penis, making him groan and whimper with pleasure. When he had reached the full expansion of his erection, I started flicking my tongue sideways, curling it up around the head, then swirling it around under the ridge exposed by his soft, stretched-out foreskin, marking figure-eights with my tongue. Sweet tangy salt invaded my tastebuds as my ministrations caused beads of precum to seep out of the little hole at the tip.

Pulling him free of my mouth, I licked his shaft in broad, slow strokes of my tongue, then shifted lower and licked at his balls, coating his lightly haired scrotum with my saliva until each testicle could be sucked lightly into my mouth, just as I had sucked in his penis. That made him gasp and twitch, groaning deep in his broad chest at the pure pleasure of being orally balled.

Swallowing hard, I licked my way back up his shaft, resting my forearms firmly on his hips, one hand steadying his shaft while the other grasped it firmly at the base. When I was ready, I deliberately yawned. Swallowing hard again, I repeated the yawn, then did the pattern one more time, finishing off with a wide-mouthed yawn and a purse of my lips over his saliva-slick head—and sucked him into my throat. Not into my mouth; into my *throat*. Swallowing him breathlessly all the way to the fingers circling his base.

He shouted, bucking up, but I firmly pressed down with as much of my weight as I could manage, focusing hard on controlling my gag-reflex. When he finally stilled, I withdrew, gut tight in the effort to control the natural urge to gag. A glance up the length of his trembling body showed tears leaking down the sides of his face again, this time from a delerium of pleasure. Licking my lips, I swallowed-and-yawned twice, pursed my lips, and gulped him down my throat again.

He didn't buck up in surprise. He sobbed in pure bliss, gasping when I took my confining fingers away and tightened my lips around the very base of his shafted again. Twisting my head slightly, I rubbed his balls with my chin, then pulled off of him very, very slowly, sucking the entire time. By the time I reached non-gagging range, he was trembling, on the verge of cumming, so I reapplied the pressure of my forefinger and thumb to the base of his penis, reaching for the picnic basket. It was a bit of a stretch, and I had to release him from my mouth to grab the wicker box. Pulling it closer, I opened the lid and inserted my free hand, fumbling around through the contents until my questing fingers identified what I wanted.

Pulling the latest toy out, I deftly wrapped up his penis and scrotum in the penis leash, separating his balls to either side in the three-lobed figure-eight pattern the strap was designed for. Slipping the tongue of the leash through the tiny buckle, I pulled it just barely snug, then adjusted the lay of his balls in the straps, shifting the leather down a little lower on his shaft as I removed my other hand, and finally pulled the whole thing tight. He grunted, arching his head back, then rolled slightly onto his side so he could lift up his head and shoulders and look at me.

I flicked the tip of his dick with my fingernail "Bad Mr. Bear. I didn't *say* you could move. Ten demerits."

He shuddered and dropped back onto his handcuffed arms, panting heavily. A groan escaped his throat. I'd cut off the opportunity for the blood engorging his shaft to retreat, leaving him insistently erect. "I don't know how much more of this I can take…"

That reminded me of something. Something I'd forgotten, something important. Shame on me. I crawled up the length of his body, straddling his waist, deliberately brushing my groin and inner thighs against his enforced erection, making him groan again. When my head was level with his own, I leaned over him and smiled. "I forgot to give you your safe word, shame on me. For my mistake, as I am a fair Mistress, I will reduce your demerits by five, bringing your current tally to five demerits. I shouldn't have forgotten them, but then you shouldn't have let me forget. But since you are new to this life, I will explain them to you now.

"I have two safewords, actually. The first one is an actual word. 'Hold.' All you have to do is shout *Hold!*," I told him, putting enough gut-emphasis behind it that he blinked, "—and I will stop whatever we are doing. End it, remove all devices, cease everything, restore you to normal, the works. The other is a rhythm, and it's the old Morse Code SOS signal—three short, three long, and three short again; that one is yours to use should you be in a position where you cannot actually say the first safeword. Thump your head, snap your fingers, flex your dick, and I will cease all activities.

"If at any time I do something that makes you fear for your physical safety, you can use the safe word to stop me, and I will obey; that is my promise to you. But you have to promise that you will think long and hard, when I try to take you past a boundary—is it really physically harming you? Or is your fear of the unknown and the suffering of a little pain blocking my attempts to help you reach the true nirvana that awaits you? Remember those two. 'Hold', and SOS. Use them sparringly at best."

As he stared up at me, I bent down and kissed him. He responded with a moan, lifting his head up to deepen the contact. I treated him to some of the same talented tongue-action I had used on his shaft and balls, and found him treating me to a similar display of sexual interplay, with the same talented tongue that had licked the cream out of me. Dropping his head with a groan, he slowly opened the eyes he had closed. I smiled down at him. He knew how to kiss my mouth lips as well as he could kiss my pussy lips. What a talented little bear I had in my care!

"…Do you like what we have done so far, Mr. Bear?" I asked him softly, still smiling.

"God, yes!" His hips strained, brushing his cock against my bottom, playing with the hem of my short, royal blue slip-skirt. Frustrated that I wasn't quite long enough in the body for him to prod at my cunt, he groaned and begged. "Will you please fuck me, Mistress? I want to feel you cumming on me, fucking your brains out on my…on *your* penis," he corrected himself as I arched a brow. He squirmed under me, trying to inch himself high enough that he could give me a good, old-fasioned poke. My smile broadened.

"Your subservience pleases me. Two merits. That leaves you with three demerits to work off. I'll let you know something of the scale system I use," I added conversationally, hitching myself up along the floor even as he almost reached his intercourse goal. "It is harder to achieve merits than it is demerits; at least, in the beginning, when you're still learning how to submit yourself utterly to my will. But if you earn twenty merits, I will give you a blowjob that will cross your eyes and make you cum like a vacuum hose. If you earn fifty merits, I will strap your penis in a tight leash so you can't cum, and fuck my brains out, as you have invited me to do so, and then I will release you so you can orgasm. If you earn one hundred merits, with no demerits on your balance…then I will fuck *your* brains out. In fact, I will give you one night of pure, vanilla sex, in whatever ordinary, vanilla positions you desire."

He stared up at me at that, no longer squirming. Twice he blinked, then finally drew in a breath and asked, "And if I want to be Dominant one day, Mistress? For just an hour or two? How many merits will I need to earn for that?"

"None, for now," I had to disappoint him. "You have neither the training nor the discipline to be trusted with the toys of a Dom. I myself was a sub for two full years, and an apprentice for a year more, before I was completely free to assert my will upon the men and women who crossed my path."

"—Women?" he asked, blinking rapidly at the idea. "You…and another woman?"

I smiled wickedly down at him, bracing my crossed forearms on his chest. Oh, yeah, every guy's fantasy; two women going at it with all the lust and passion in them. How much more of an exhilarating taboo was it to think of two women in a D/s scenario, one sexually dominating the other? "Get that thought out of your head, my naughty little bear. *You* asked for sexual monogamy, remember? And I agreed to it. That means I don't get to go down on another woman, not even while you watch...unless our agreement changes at some point in the future. But since you're the one who asked for it, it's up to *you* to change the agreement, which at this point I do not think you will do, just yet."

With that, I pushed up from him, walked over to the sink, and spent a couple minutes writing down what we had just done. Leaving him handcuffed and penis leashed on the floor. When I was done, I turned around. He was still lying on his back, the small of his back arched up so that it took some of the pressure off the uncomfortable lump of the handcuffs, but his head was turned towards me, his eyes devouring everything about my royal blue clad curves. His penis, which looked fantastic in its tri-wrapped penis leash, twitched as his gaze played over my plump, curvaceous body.

"...You are so fucking sexy, Mistress."

I smiled at him, warmed by the sincere compliment. "Such sincerity gets you two more merits…but all compliments *must* be sincere to qualify," I cautioned him, strolling slowly his way, letting my low-heeled pumps clack deliberately against the tiles. "Lie on your side, my little bear. I have one more thing to introduce you to, before we call it a night."

He did as I asked, twisting onto his right side. Since his arms were bound behind his back, that made him tip towards his front, pressing his cheek against the cool tiles where his body had come fully off the towels. "Is it a punishment, or a reward, Mistress?"

"...Neither," I clarified softly. "It is merely an introduction. At some point, it may become a punishment; at others, will become a pleasure. For now, it is enough for you to know what it feels like, so that it will not shock you too deeply further on in our play."

Kneeling behind his thighs, I picked up the discarded anal probe. Reaching into the picnic basket, I found the tube of K-Y jelly and used it to coat the rounded tip and twig-like shaft. Replacing the tube, I turned to him, glad to see he hadn't looked behind his shoulder, which would have earned him a few more demerits than the one that lay on his tally now.

"This might be a little cold at first, but it is necessary for this experience to feel even remotely good," I warned him, and pried up his left asscheek, baring his puckered little anus. Adjusting my position for better leverage, I pushed against his tight little hole. His buttocks clenched instinctively against the cold intrusion. I squeezed his left cheek hard, not about to let this resistance of his go unthwarted. "Relax! You are going to feel this entering your ass outside the pleasure of a climax, and you will feel it entering you *now*"

With that, I shoved it in, despite his resistance. He gasped, and I let it stop just in past the outermost ring of his sphincter muscles, but not quite all the way into his rectum. Deliberately forcing him to feel it stretching his anus. Then I pushed it slowly, deliberately deeper, watching his flesh re-pucker partway again as the narrower shaft started disappearing into his depths. When it was in to the hilt, I stopped the probe.

"There. That wasn't so bad, was it?"

"…No, Mistress," honesty forced him to admit. Slowly, I pulled it all the way out again, and he moaned softly, pushing anally to help it get back out again.

"It just feels like you're having a good, satisfying shit, doesn't it?" I asked him lightly. "Except you're not doing any of the straining required for taking a dump." He grunted an assent, then grunted again when I pushed the probe back into his ass, once again all the way, nice and slow.

I pulled it out again, letting him feel every inch of natural resistance as it slid and popped back out, then pushed it back in just far enough that the rounded head popped past his sphincter muscles. Adjusting his legs so that they were a little more bent, giving me a little more maneuvering room, I grasped the hilt and gently swirled the probe. He groaned out loud, clearly enjoying it. I straightened the probe, and pushed it quickly in about two inches, making him gasp again. Neither pushing in fully nor withdrawing all the way, I then frigged his anus with the shaft, thrusting it in short, swift strokes that travelled both ways about an inch, inch and a half. Rubbing the branch-thin shaft against his sphincter muscles, and the ball-shaped head against his rectum. Twice I angled it towards his prostate, making him jump and twitch.

Finally, I drew it out so that the head rested in the vise of his sphincter muscles, and twisted the head back and forth. A quick shove in, a fast yank out, twice more in this fast of an attack, and I popped it out and left him breathing heavily as I placed the anal probe on the tiled floor.

"Onto your back."

Obedient, he rolled onto his bound arms, arching his belly upwards once more. Reaching down, I carefully freed the little tongue of the buckle on the penis leash, then flicked the straps off his penis and popped the head and about an inch or so more into my mouth, thoroughly tasting his precum-coated, hot, pointed mushroom of flesh. The tip of my tongue danced around the edges of the ridge defining his glans, scooping up every last sweet-sushi flavored drop. Apparently that was the next-to-last straw.

"Oh, god, I'm gonna cum…!"

With that, I withdrew my ministrations, releasing his shaft with a sucking pop. A groan of disbelief left his throat as I stood up over him, placing my hands on his hips, leaving his penis twitching without satisfaction.

"Please, Mistress—I've got to cum!"

It is another curiosity of men that, the more you leave them wanting, the more they'll want you more. Satiate a man, and he might move on, looking for fresher, greener pastures...but deny him the full package, and he'll stick around with the increasingly obsessive need to have it all. By denying him a second orgasm tonight, by leaving him in a state of extreme need, I was guaranteeing that he would keep wanting me. I was also taking the first steps to training him to cum on command, one of my favorite tricks. So rather than giving him relief, I instead stated firmly,

"Your last demerit shall be served out by your *not* cumming, tonight, Mr. Bear. You are not allowed to jack yourself off, or even to touch yourself. You will roll onto your side, and as soon as I have released you from the handcuffs, you will get up onto your knees, take the anal probe to the sink, wash it thoroughly while still on your knees, dry it off, and bring it back to me, all on your knees. Protesting will get you five demerits, as will delaying your task. Getting my notebook wet in the process will earn you twenty-five demerits. Now, roll onto your side."

Groaning in frustration, he did as I demanded, rolling onto his right shoulder again. Crouching, I dug in the basket for the handcuff key, and released his hands. As soon as he was free, he twisted and pushed onto his hands and knees, then sat back, rubbing at his wrists. He looked at me, a little doubtfully, then when I arched my brow, picked up the anal probe I had set on the floor and started shuffling across the tiles on his knees. While he was doing as commanded, I packed up my picnic basket, putting everything neatly back into its place. There were still several toys left in the basket that hadn't even seen the light of day, and more back home that I could incorporate into my plans. For that matter, if he had a weight room in this oversized house, the possibilities could be stretched out even further. What a wonderful evening this had become.

By the time he came shuffling back, I was seated in the chair again, my legs crossed daintly, my hands resting in my lap. Cool and composed, and completely in control. He stopped right in front of me and held out the anal probe, sitting back on his heels. "Your probe, Mistress, cleaned just as you asked."

"Has it been cleaned thoroughly?" I asked him lightly, and he nodded.

"Yes, Mistress."

"Then kiss it, to show your thanks for how gently it was applied today." He gave me an askance look, and I arched my brow. "You *said* it has been cleaned thoroughly. If this is so, then you should have no hesitations in kissing it, as I command."

"…Yes, Mistress." Bringing it to his lips, he saluted it. With three kisses, not just one. One for the rounded knob, one for the twig-thin shaft, and one for the hilt where my hand had grasped. Only then did he hold it out again. "Thank you for allowing me to know what this feels like, Mistress."

Oh, I was definitely keeping him. What a natural! Taking the probe from him, I tucked it into the basket. "Assume the position, Mr. Bear. I will be right back."

Obediently, he placed his hands behind his head. I started to rise, then sat back down again and nudged at his knees with the tip of my suede pumps, flashing a little of my pussy as I did so.

"Knees wider, Mr. Bear. Do not ever forget that when you are in the punishment position, your thighs are not allowed to touch my cock, nor the balls that hang from it."

"Yes, Mistress. My apologies, Mistress," he added, shuffling his knees further apart.

"That's five demerits for forgetting. Maintain the punishment position," I reminded him, rising and moving around his kneeling, vulnerable body. Striding to the sink, I checked the notebook lying open next to the sink, running my hand lightly and carefully over the pages. I was mildly surprised to find that not a single drop had been splashed onto it. Picking up the pen, I filled out the last of our session, and made the notation that he had five demerits unaccounted for. Closing the book, I slotted the pen into the wires piercing the spine, and returned to the edge of the tiled floor. Bending over, I tucked the notebook into the basket, pulled out the collar leash, then straightened. "Return the chair to its original position, Mr. Bear. You may walk to do so."

"Thank you, Mistress." Rising, he picked up the chair, moved it back beside the magnificent, oversized, four-poster bed, then returned to his original place, knelt, and resumed the punishment position without asking.