Man Disciplines Sissy Ch. 06

"Ray...?" I whined.

Then I felt a searing, harsh snap of pain down there, OH!, the sting was sudden and sharp and I must have jumped a couple of inches, even in my high heels.

I cried out, almost a scream, and drew in a fast, full breath and reached back, and looked back too, and saw the thin, dark-blue rubber band in his hand. It was stretched across Ray's left thumb and forefinger. I looked at Ray's face, and he had that flat, amused, masculine grin again, and part of it was probably because my eyes were wide with hurt and surprise. "Bend back over, and hold that slip up," he said. With a desperate little sob I gathered and lifted my slip again, and bent my waist, and felt emotion rise, the kind that makes the lip tremble, that brings the tears.

"Don't, please, ohhh, nooo," I said, but I knew what was coming. His fingers brushed my scrotum, and then snap! again, the rubber band snapping sharply against the back of my dangling scrotum.

"Owwww Daddy!" I moaned, and this time the sting made me bend almost double, and Ray steadied me until I recovered a little.

Later, thinking about it, I realized that the rubber band stung a lot more than last night's flicking fingernail, but this sharper sting went away quicker. There was more of an ache remaining after he flicked my scrotum hard with a fingernail, than this evening, with the hot slashing sting of the rubber band.

I whimpered and moaned, gathered myself, and I was afraid to look again, but when I did, Ray was sliding the thin, small rubber band over the head of his hard 7.5 inch cock.

"You'll be seeing Daddy soon enough, honey," Ray said, chuckling dryly. He pushed me forward a little, and stood up, holding his cock out. My pink panties, pulled partway down and bunched around my thighs, slid to my knees and I grabbed at them to keep them from falling all the way to my ankles.

"I need to sit a little higher, I think, honey," he said, and sat on the arm of the sofa. Grabbing my wrist, he pulled me close again, and I got a little confused, not sure what he was doing. He smacked my bottom again to get my attention. When I jumped and whined, he smacked it hard again, and then a third time, then moved me to where he wanted me, keeping me in front of him, positioning me by my hips.

"Pay attention, honey," he said. "Keep watching." He laughed because I was whimpering, as always, when I felt his firm hand, the shame it caused me.

Sitting on the sofa arm now, Ray hefted his penis, the chuckle still ringing in his voice as he spoke. "Does that look like, oh, about three inches, right about...there?" He held his cock up for me to see clearly. The thin little blue rubber band was just the right diameter to stretch comfortably around the shaft of Ray's penis, yet remain firmly where he put it. It made a clear line there, all the way around, a little more than a third of the way down the length of his whole cock. Above the rubber band, the helmet stood out, engorged, purplish pink. The pee slit in the middle of his turgid glans glistened with viscous moisture.

Ray was showing me his cock, but he was looking at my face. He had pulled me by my hips, putting me back where he wanted me. I was straddling his knees, but I turned my waist, to face him better. I looked at him. Our eyes linked. I looked down, where he was casually hefting his heavy, engorged cock, and a little shiver tremored through me. I took a couple deep breaths, but I hiccupped a little on the second one. He made me so nervous, so emotional, so unbalanced. "Yes. Yes, um, Ray," I said. My eyes drifted up to his face again, and he continued to stare at me, as if he expected me to elaborate, but it was all I could think of to say. I knew what the rubber band was for.

"I got it over at the conference reception, baby," he said. "Somehow, that seems appropriate, doesn't it? They had a little basket of them. Shirts, not rubber bands. One of the booths was giving out a stupid t-shirts, all rolled up, each one with three or four of these little rubber bands bundled around them, to make them compact."

My company was giving away, among other swag, t-shirts. I felt my face blushing hot and pink again.

"Yes, honey, your booth. That's where I got your cell number, too, that's how I called you, when I made you tell the taxi driver what a sissy you are." He chuckled.

Ray reached for my hips again. His hands grasped me, pulled me, and maneuvered me back into position.

I took a deep breath. "That's right, honey. Three inches. We needed something to mark it, measure it, on my hard cock... But, it--the rubber band--proved useful to get your attention too, didn't it hon?" His hands were on my bottom, but then he slid a thumb and finger right between my upper thighs and gave a quick little tweak to my scrotum, and I cried out, and twitched. Ray chuckled, and slid his hands to my bottom, then my hips and waist.

His grip was firm. He pulled, and I bent slightly at the waist again. His hands slid back from my hips and he was palming my bottom again, then he slid both hands lower, grasping my hips and my upper thighs. His palms and the balls of his thumbs hefted up under my ass, the lower parts of my ass cheeks, where my bottom hung firm, but a little bouncy too, the way his hands moved and groped, above my thighs. I felt the balls of his thumbs moving then, both of them on the bottom part of my ass, then sliding up and in, parting my cheeks, low, just above the tops of my thighs. All the air left my lungs as his thumbs probed upward, his hands firmly pushing my cheeks apart.

Somehow he managed to part my ass, tease my hole with his thumbs, and pull me back to him, all at the same time, toward his upright, erect penis, and I felt his cock slide there, between my cheeks, as he slid his thumbs back out of the way a little to let his shaft invade that space, and he grunted.

The knob of his penis slid up, occupying the crack of my ass. "Yes, honey," he said. "Are you ready for Ray's three inches?"

"No," I said, but it was merely a vocalization, a placeholder, an answer that meant something other than face value, an answer of wanting, of shame, of need. My back arched and my knees shook and my toes pigeoned submissively. More of a wait, than an actual no.

"Because you know what we need, don't you honey?" Ray said. "Go get it, Lance."

I froze, not because I didn't understand. It was because I understood exactly what he meant.

"Go on, honey," Ray said. When I still didn't move, he smacked my bottom, hard, with his right hand.

I jumped and whimpered, and took a step, trying to keep my balance. He spanked me again, just as hard.

"C'mon, honey," he growled. "Let's not dawdle. You still have to go upstairs in your pretty dress, to meet Daddy, and you know you really did annoy him earlier, remember?"

I felt my face flush, warm and red. "Yes, in the taxi," I murmured.

"Yes honey. Don't worry. We'll get you ready for daddy. Now get it." He smacked my ass again, and I jumped and darted away from his hand. I was kind of waddling a little as I walked, because my little panties were still down around my knees making me a little clumsy. I went right into the bathroom. I looked over my shoulder as I went, pulling my pink panties up far enough to stop waddling so much. I saw Ray handling his cock, hefting his scrotum, keeping himself hard.

When I came back, Ray said, simply, "Show me."

I held up the little, white plastic bottle. My hand shook a little.

"Yes. Good boy. You little sissy, you cockslut. You knew exactly what I meant." I stood next to him where he sprawled on the stuffed sofa arm, his pants and underpants around his knees, his hard cock still throbbing a few inches from where his right hand rested casually on his naked thigh.

The little plastic bottle was the hotel-size, complementary. With a fancy light-blue flower-petal top. Hand and Body Lotion.

I was taking deep breaths again. Ray nodded at me. I fumbled with the little bottle, twisted the top off, and squeezed about a half-dollar sized puddle of creamy, pearlescent lotion into my right hand.

"C'mon, baby," Ray said, with a very slow, very slight gesture with his hips. I slid my hand down onto the knob of his cock, and slowly spread my fingers, closing my creamy hand around his throbbing shaft and crown. He took the little bottle from my hand, looked at the label, lifted it to his nose and sniffed its scent.

"Oh yes, honey," Ray said, inhaling slowly, reacting to my hand lotioning his glans. His hips tightened again, moving subtly, rising to my hand. His cock was hard, warm, and I closed my thumb and fingers around its girth. I felt the ridges of his circumcised knob slide past my fingers into my palm as I spread the white lotion around. Ray was watching my hand. "Oh baby, that's good," he whispered. "But I guess maybe I shouldn't be surprised you'd be good at stroking cock. Being such a sissy, you probably don't get a lot of women, do you honey?"

I looked away, feeling the humiliation he intended. I couldn't answer him. I thought about the woman I'd been dating. I'd been hoping for romance, but I didn't want to face the obvious. Our dates were becoming, more and more, a friend-zone situation.

Ray saw it in my expression. He knew how to read despair in my face. His smile flattened, his chuckle rasped, further deepening my shame. "Yes, I know honey. You don't have to answer. It's kind of obvious. Women can tell, too. They know a sissy, sometimes even better than a man. They know what you are."

He handed me the lotion bottle again, and I paused lubricating his shaft and glans, and squeezed more lotion into my hand, and handed him back the bottle. He nodded, and I applied the lotion to his cock, which twitched and throbbed in my hand.

"Oh yes, baby. Just the top, baby, the head. Your three inches," he whispered. Keeping my touch light, I spread the white lotion on Ray's hard cock, on the crown and upper shaft, using only my fingers and thumb. Ray adjusted his position on the stuffed sofa arm, sliding his hips forward a little so that they hung over its front edge. When I closed my hand around his cock, and slid it down, under the slick lotion I could feel the tight little rubber band, marking the three-inch line.

"Okay hon," Ray said. "I think that's enough. Get like you were," With a little humming grunt of command and lust, he pushed my hand away from his penis. Ray grabbed both my hips again, moving me decisively, positioning me in front of him, and then his left hand yanked my panties a few inches further down. I had pulled them up so I could walk better, when I was getting the lotion. "C'mon, baby, bring me this ass," he said, reaching out and giving it a firm little smack. "Turn around and straddle my knees." I watched as he grasped his cock with his left hand, but he was careful to stay low on the shaft, below the rubber band, below the glistening lubrication. His thumb and forefinger circled the base of his cock, and he pointed it up, aiming it at my ass. "You know where this is going next, hon." I looked at him, saw the expression there, the lust, the want, the intent.

I turned around, my steps tight and careful in my high heels, constrained as well with my panties at half-mast where he had just yanked them down. I was shifting my weight, about to step over and around Ray's knees, to resume the position he wanted.

"Wait," he said. I stood poised, awkwardly still. My right palm and fingers were still streaked and splotched with Hand and Body Lotion, so my hand floated in the air; I didn't want to touch anything. Back behind me, Ray's hand, his right, reach between my thighs. I thought he was going to goose me again, but then my panties were moving.

He was pushing them down further, to my knees. "Let's get these off," he said. He pulled back on my panties, stretching the elastic, and I swayed a little, but took a small step back toward Ray and the sofa, and I felt my little pink panties slide down all the way to my ankles. I found myself wiping the lotion remaining on my right hand onto my own belly, so I wouldn't spoil any of my clothes with it. "Step out, hon," he said. In my white high-heel sandals I stepped out from my little pink panties, both feet. My left heel snagged a little in the bunched satin, but Ray leaned forward, gave another yank, and freed me from the panties entirely. He draped them over the edge of the middle cushion of the sofa. Then his hands were back on my hips, guiding me, a little forward, and I stepped around his knees, and he pulled me back where he wanted me.

"Bend your waist a little, princess" he said. I moaned and bent forward, and he pulled me backwards. I was balanced, my high heels helping shift my posture forward a little, and his thumbs pushed my ass cheeks again, opening me.

"Hold your ass, hon," he said. "Reach back and spread your cheeks." I did as I was told.

Ray took his left hand off my ass, and used it to grasp his cock, and point it, aim it. I could feel its knob slide right into the space between my bottom cheeks, and my hips twitched again and I moaned. "Right there," he said. "Mnn," he grunted, "Mnn hmmn." I felt it, felt the warm knobbed crown of it, slick with lotion, push right up against my crack. It slid up and down, finding the center, and Ray still had one hand on my right hip, and his hips gave a little thrust as he pulled me to him, then his other hand was back on my left hip and he was very gently, carefully pulling me to him, pulling my ass down onto his cock.

"Yes," he said. "Right there." And I felt the crown of his penis pushing. I was holding my cheeks open, and his hard cock, slick with lotion, pushed it's head slowly into my ass, spreading my anal ring open, stretching me, tight but warm, encircling the knob head of his cock, as he slowly pulled me back. I felt that slight release, when the shoulders of his knob popped in. Then he pushed slowly in, another inch or so, and stopped. He held me. He held very still.

"Three inches of hard, slick cock," Ray said. "But you know you want more, sissy," he said. He raised his hips then, and I watched, looking down past my own shoulder, and Ray, still holding both my hips with both his hands, flexed himself within his loins, a contraction that I felt more than saw. I actually felt him tighten himself then, a little kegel maneuver that fattened and swelled his erect penis up inside me, and I felt my ass's sleeve twitch in response, and I moaned.

Very slowly, while Ray grunted a slow, quiet moan, the crown of his penis, erect and pulsing with his little voluntary contractions, slid into me another inch, into my ass. It felt hot and hard at the same time, its surface soft and fleshy, but so stiff and rigid just inside, just beyond that warm layer of softness.

"Right, right...yes, hon, I'm talking to you, right...there!" Ray said softly while he paused his grunt of pleasure, to tell me this, this progress report.

He stopped completely, holding my hips, not twitching his cock, not letting me move either, his own knees and hips frozen at that spot. "Feel it? Your three inches of Ray's hard cock in your tight little sissy pussy, that's what you have right now."

Still holding my hips in that same spot, Ray rocked his knees slightly, and I could feel it now too. The rubber band. Its tight little ridge of rubber, surrounding his shaft and marking a precise portion of his penis, about an inch and a half below the crisp shoulders of his fleshy purple knob, his sensitive glans. Just like I could feel it, that loosening feeling when the shoulders of his lubricated knob popped inside me, now I could feel the rubber band rolling a little, giving slightly as he rocked, right there where his shaft held the round lips of my sphincter stretched open. The sensitive skin there felt the little blue rubber ring sliding and rolling slightly as he moved his cock. The elastic mostly stayed in place, it didn't slide down his shaft, but I could feel it roll and slide a little when the stretched elastic surrounding his penis pushed against the skin of my anus, and when he backed it out it rolled again a little. He gave another little grunt and slid that same half inch of his erect shaft back and forth, in and out of me.

"Feel that, hon?"

I stood, waist bent slightly, in my high heels, almost sitting in Ray's lap, but holding my cheeks apart for him, his cock pushed halfway into my ass. I moaned. Yes, I felt the rubber band, and his knob and shaft, moving inside me when he pushed and pulled.

But something was happening...in there. Something else. The knob of his cock was inside me, in my ass, and I felt something almost ticklish, even slightly irritating perhaps, where that plum-sized knob was sliding up against the inside of me, just barely touching, and stimulating the spongy gland positioned right ...there. A very sensitive spot. Was it just about three, or three and a half inches in, the swollen bulb of my prostate gland? When I felt that sensation, the tickle of his knob and ridges almost brushing that area, suddenly I stiffened, my whole body twitched and hardened like concrete for a moment, and then my hips shivered and my little cock rose, pushing out straight now, and still rising higher as it twitched. His cock had almost found my P-spot, and while the tight little rubber band rolled a little where it surrounded his shaft and rimmed my sphincter, I was getting a hard little erection, and yet his measured length wasn't quite reaching the magic button. Almost. Teasingly close, but not quite there.

"Ohhhh," I moaned, bending over there, my knees shaking slightly, my two hands holding my bottom cheeks, straddling Ray's upper thighs as he slowly pushed the head of his cock in and out of my ass. Each time as his cock slowly slid into me, when I felt that tight little rubber band that marked the top three inches of his manhood, I yearned for more, another half inch, to take me over the edge. And this time when I felt it, when I felt the urge and the desire, my knees twitched and I started to let my hips drop.

"No," Ray said, and he tightened his grip on me. I stiffened again, and felt him. With those three inches of cock inside me, and no more, no less, he held me firmly, while he slowly worked his own shaft back and forth, very deliberately. My breathing became rhythmic, with a little whining moan, as he twitched the head of his cock right there, just short of the nerve bundle a finger's length into my sissy tunnel, his big hands firmly holding me in place, letting the shoulder ridges below the glans of his hard cock tease me, just short, tantalizing yet holding back.

"Yes honey, look at yourself, needy little secret sissy, cock-hungry, and so wanting more," Ray said. "But not yet, baby," he said, and he gave my hips a little push. While he held me off, he eased his own hips down, and back. His cock slid out of my ass, with a little pop, more a feeling than a sound.

I straightened up, catching my breath, my bearings. I looked at him, at his throbbing penis, still pushing up, still hard, still glistening with fluids and lubrication, still with a thin blue elastic to measure off the top three inches of its girth.

Ray saw me looking at it, and he grinned, and reached for his cock, his grasp quick and manly. His fingers circled it, gave it a stroke and it seemed to grow a further half inch in that moment, the plum head striving to define itself at the top of the shaft, stretching that little length of softer skin just below the crown to its maximum.

"You'll get another inch, honey, in a little while, when it's Daddy's turn," he said. He looked at his watch. "And you'd better be getting ready, honey." He reached for the panties tossed onto the sofa next to him. He held them up, using both his hands to spread and fluff them open for me.