Emperor Jack #02

The third contestant was one my lobbyists, Monika. A natural blonde from the coast that had once been called California, she was a dream come to life. Hot body, great tan, blonde hair—natural, which she made sure everyone knew by keeping the tiniest thatch of pubic hair above her slit rather than shaving totally bare like most of the girls did (following my personal preference). She had been numero uno before Shana arrived, and she had some advantages. How should I put this... I bet if I were making a porno, what she could do would look better on film than Shana. But with Shana, it was more than just physical (although it was most definitely physical too). Monika was jealous; I'm sure almost all of my advisors would have picked Monika ahead of Shana if they had to choose one. But, because I'm a redhead guy, Monika found herself second fiddle, and was none to happy about it, I can tell you. She never showed any of that around me, of course, but I heard, both directly and indirectly, about some of the snarfy, bitchy things she said in their living quarters, especially to Shana. I'd plowed her furrow many times, and it always pleased me. Did I want to try someone new, or go back to an old standard? As Monika rolled around on the floor, showing me those tight, triathlete cheeks, I was leaning towards choosing her.

Monika ended, and went off to the side to join the others. "Is that everyone?" I asked.

"Actually, no. There's one more... special contestant," Chuck said vaguely.

I looked around; no one else seemed to be forthcoming. That's when Shana stepped out from behind my throne and walked to the center of the floor.

"Shana?" I said in shock. Shana bent slightly, pulled her bikini bottom up, and slapped her cheek, demonstrating its firmness. "You said you didn't want anything for your birthday, my Lord, but I knew there was one thing you didn't already have, that I could give you..."

"Shana... are you sure?" I was excited like a schoolboy getting his hand into a pair of panties for the first time. She didn't say anything, but untied the strings on either side of her bikini bottom. When they fell away, they revealed that she was already wearing a metal butt plug, stretching her ass so it could learn to accommodate a dick. Mine.

I wiggled my finger for her to come to me. She came towards me, untying her top; it got caught momentarily in her long red hair as she approached. I was so engrossed in watching, I didn't even notice the staff engaged in a flurry of activity--the losing contestants discreetly exited, a large mat/mattress kind of thing was laid out on the floor a few feet away, and Chuck threw a pillow that had appeared as if by magic at my feet. Shana knelt on the pillow, finding a tent pitched in my lap. She untied the string of my suit. I had to half-stand for her to be able to pull it off, as the waistband kept getting caught on my erection but she got it off. I sat down and closed my eyes, sighing in pleasure as I felt her gentle lips encircle me, swallow me, and felt her tongue caressing me. Reflexively I reached down, my hands knowing exactly where her breasts would be, her nipples already excited in anticipation of my fingers' return.

I just sat there for a while, engaged in an activity that was a daily occurrence and yet never felt boring or repetitive: Shana sucking my cock with that special attentiveness that was her trademark, while I gently stroked and played with her breasts. She could easily bring me off if she chose to this way, just by slowly picking up the pace--she often did so, in fact, on days that I was particularly tired. Tonight, however, I was to shoot my wad in an entirely different location, so she carefully kept it slow.

I let go of her nipples, caught her wrists gently, and pulled her up onto my lap. This was another common position I never tired of--sitting on my throne, Shana would balance herself on my cock and fuck herself on me. All the while I played this little game where I tried to catch the tender pink nipples with my tongue as the bobbed by, a task that became harder as Shana would increasingly bend over backwards, using my penis to stimulate her clit. Most times this would eventually bring us both to orgasm, but this was not like most times. Shana didn't bend backwards, she put her hands on my shoulders and stayed upright. She pussy-fucked me for a short time, then she half-collapsed forward onto me and kissed me deeply. I never kissed my other partners because they felt like strangers when kissing, but not Shana--she felt like the special lover she was. But she kissed me hard, and then whispered into my ear, "My Lord... if I have won the contest, I would like to receive my prize now."

Inches away from each other, our eyes met. Her eyes showed a little trepidation, but it was also clear that she was determined to do this and her resolve to succeed was determined to override any fears she may still have been feeling. I smiled softly.

Shana lifted herself off of me. She pulled my shorts off of my ankles where they had fallen. A jar of lube had been placed on the floor by my throne; Shana knew where it would be and retrieved it. She then carefully slathered my penis with the slippery stuff; even her fingers made my dick feel like heaven. Satisfied, she stood up, taking the jar with her, and stepped over toward the mat. She knelt on all fours, then reached behind her and gingerly pulled the plug out of her ass. I watched for a moment, then stood and moved toward the mat myself. She grabbed a generous dollop of lube and began to slather her butthole with it, pressing two finger into her rectum to grease every surface she could think of. It was far more than was needed, but it told me she was still concerned about how this might go.

Rather than take up my position at her backside right away, I first straddled her right leg between mine, partly at her back and partly at her side. I gently lifted her lovely red hair and slid it so that it cascaded over her left shoulder. This bared the side of her neck, which was my target. I knew she liked it when I kissed her there, and that is what I did. Lovingly, I left soft kisses on her neck, while with my right hand fondling the nearer nipple. She raised her head, making it easier for me to find her neck, but I could hear in her breath that she found the attentions pleasurable.

Still working the nipple, I moved my kisses down towards the shoulder. At the same time, my other hand found her engorged clitoris and began to stroke it. I didn't need to see her face to recognize her response; her eyes were closed as she enjoyed the sensations of my attention. This was my aim--I hoped to invade her final frontier while her attention was focused elsewhere, on her own pleasure, so that she might avoid tensing in fear. I touched the inside of her thigh gently for a moment; she responded by spreading her legs farther apart. Then I resumed stroking her clitoris, tweaking the tender nipple with my other hand all the while.

Her ass looked up at me, a hidden treasure now revealed and ripe for the taking, glistening in the dew of the lube. I was hard as a iron spike. I rubbed her clit harder and harder, getting her more and more wet. Then I surreptitiously slipped my hand from her nipple, along her side, and gently down her back. Then, quickly, I grabbed my stuff, pointed it at the smiling eye, and pushed against it. There was so much lube, and Shana was relaxed from focusing on her clit, that I was able to slide in on the first try.

Shana jerked with surprise as she felt her anus penetrated. She tensed up, squeezing my erection hard. I expected this; continuing to work her clit, I leaned forward and whispered directly into her ear. "Relax, darling. It is done... I trust it did not hurt?" She shook her head. "And it will not hurt if you can stay relaxed. Focus. Focus on what your body feels..." to accentuate the point, I grasped her nipple again as well. I could feel her relaxing as she focused on the familiar pleasures rather than the unfamiliar penetration. I felt the sphincter loosen, and with inner glee I, for the first time, was able to fuck my beloved Shana's ass.

It didn't take long for Shana to realize that she had been worrying for nothing. It felt odd perhaps, but with proper lube and preparation it was not painful to be reamed. I was able to pick up the pace without any difficulty. I saw her arch her back, quickly learning how to position herself to maximize penetration while minimizing discomfort. I kept working her clit for a while, but at some point I realized I'd been doing so longer than I'd ever had to without bringing her to orgasm. She was relaxed enough to fuck, but I realized she might not be relaxed enough to cum. With a tinge of disappointment, I put my hands on her waist to increase my control over her hips and concentrated on fucking that ass.

I looked at the back of Shana's head, watched her arch her back. At long last, I was buttfucking her. But... I found myself missing the ability to look at her lovely face, lock in on her green eyes. I wondered what expression her face wore...

I decided to push my luck. I pulled my dick out of her has. Shana spun her head around to see what was amiss. I was on it like a flash, kissing her. I hear her breath heave as we kissed. Then I gently guided lovely Shana onto her back. She looked up at me slightly confused. "Please grab you ankles and hold them high, my beloved," I whispered. Blinking once, she did as she was told. Still hovering over her, I slid my torso around to hers. I kissed her, but with my left hand I guided my dick towards her back. Feeling with my tip, I felt where the beginning of the gentle curve of her cheeks began, finding the cleft between them. Then I slid slightly north, feeling for the cavity I had just vacated. I quickly found a hole, still distended but tightening. I pressed against it, and with that successfully re-entered her rectum.

I put my hands down by Shana's lovely head, hovering closely over her. Her hands gravitated towards my sides. With open-minded surprise, she received me in her rear while facing me. Perhaps she had not considered it possible. Stroking her ass, I bent to kiss her. Still stroking, I rose up again, on one hand, and let the other return to her clit. Understanding now the geometry, Shana pulled her thighs up towards her shoulders, lifting her hips that I could fuck her bottom. My fingers felt her slit dripping with arousal. I glanced down... ahhh.

What wonderfulness.

I loved to look at Shana's pink pussy, loved to eat it, loved to fuck it--but of course, could only do one at a time. But now, I could admire her delicate sex while in mid-fuck. It was wonderful, and I was entranced. I rose up slightly that I could see better. The delicate lips, wet with dew, angry pink with excitement, enticed me. Fucking her ass harder without realizing it, I used my fingers to gently pry the lips open. Like a hidden treasure, her inner sanctum revealed itself to me, a lovely jewel that called to me even as I plowed the dark passage. It was a mental, sexual overload: feeling her tight ass, thrusting, and now admiring her beckoning sex. Like a man racing up the last flight of stairs after a long climb, my excitement burst from high to off the charts. Enthralled by the simultaneous vision and sensation of sex, I exploded into orgasm, catching even myself by surprise. I was frozen, incapacitated momentarily, as with indescribable ecstasy I ejaculated wave after wave of pleasure, feeling almost as though my nuts themselves had been shot into the void. It was in all likelihood the most memorable climax I shall ever encounter.

When my senses returned, Shana was peering up at me. Her eyes spoke partly of pleasure and partly of satisfaction, but what made them so wonderful is that when they looked they saw only me. I had been married and divorced once, long ago, but I could not recall ever feeling so much like someone loved me. "I love you Shana," I breathed. She could not hide the look of happiness my words brought her. "I love you too... Jack..." She always said my name distinctly, as if it were difficult to pronounce. Perhaps it was just so rare that it was safe to call me by my given name, not Your Majesty, Your Highness, or My Lord. Our lips longed for each other, and the rest of the world melted away in our kiss.

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I was so grateful for my birthday, I spent an hour before meeting with the Europan and Brittanic delegations hearing a request from every girl that had performed for me, whether I or one of my staff had fucked them or not. Giving each of them a chance to make a million or two Terran dollars was the least I could do for the great day I had received. Shana, however, going last, refused to take advantage. "It was for your birthday, your Imperial Highness. It would be wrong to attach an advertisement to what was freely given." I half-smiled; dearest Shana. She was unlike any of the others in so many ways--although to be fair, she probably had a hundred million more in the bank than any of the others from her previous work, and would earn more before the day was out. As I regarded here, she shyly ran her fingers through her hair, pulling it back off of her left ear. When she lowered her hand, my smile grew broadly. There, along with the white and the blue, shimmered in her ear a brand-new brown earring.