Chapter Forty-Nine

Clearly Doreen’s wealth was greater than Karl had realized.

They flew first class over the Pacific, Karl squirming nostalgically the whole way. Then he expected a high-rise hotel jammed with staff and guests amid a bustling tourist mecca. What they arrived at instead was small rental cottage on a secluded stretch of beach at the edge of a state park.

The sand was volcanic black, the small bar and fridge already stocked and the bed a circular, satin-sheeted wonder with a matching mirror set in the ceiling. The atmosphere was one of sybaritic eroticism and the location as private as one could ask for. Clearly romantic flings (or at least idyllic retreats) were another specialty of Nurse Drake. They settled in immediately and were cavorting naked in the turquoise water within minutes. Well down the coast rose the expected hotels, promising fine dining, shopping and nightlife when they wanted it. For the present they had everything they needed.

And so what Karl had dubbed their ‘reverse-honeymoon’ had begun. They swam in the tropical sea, snorkeled and spear-fished and sailed, soaked up the sun and too much top shelf booze. They shopped and danced and toured the islands and surrounding reefs and spent a good amount of time just sitting people-watching. They saw amazing sights and wildlife, ate fantastic meals, watched glorious sunsets together, had exhaustive sex (along with Karl’s unlimited tits) and gazed at the stars from an equally sparkly ebony beach afterwards. They did everything any loving couple celebrating their nuptials would do. It was perhaps perversely fitting of their relationship that for them this was coming at its presumed end.

It was all heaven on Earth, particularly to Karl, who’d never travelled at all. But finally the days began ticking down toward heartbreak once again. As the second week leaked away their lovemaking regained its almost frantic pitch. Their flirting grew more freighted.

It was assumed that their parting loomed, and in defense they kept up the chambermaid fantasy – or was Doreen maybe really considering it? Karl had wanted a little spice and uncertainty to the proceedings. Now he was tormented by this, caught between great sadness, foolish hope and a new and unexpected species of dread.

As was her wont Doreen refused to dwell on the negative. She wrung all the love and joy from each day that she could. Unable to completely forestall Karl’s growing sadness and desperation though, even increasingly infected by it, she chose the second-last day of their stay to resolve the uncertainty and reconcile themselves to the future. They had one final game to play, one more lesson to impart. While Karl was finishing in the shower she slipped out and locked up the cottage. No one must disturb them until she was ready.

She met her strapping young specimen stepping naked out of the bath. Wearing a nice white robe that came with the cottage, she wrapped his hair in a towel for him and sat him down on the commode. Perching above him on the vanity, she smiled down with just the right touch of gentle playfulness.

“Karl darling, these hints and offers of yours have gone far enough. We both know the part you’ve been pining to play in my life ever since that day I was cleaning the suite.”

Doreen took his hand.

“I’m sorry my love, but we can’t be mates and we can’t be lovers after this. You know that. We could live with the age difference; it’s even part of the appeal. But my career would interfere. There’s just no way around it. I have to be free to devote myself completely to each new case, without a jealous, cuckolded husband lurking around.

“Nor can I string things along with you indefinitely. It would be too upsetting for me and detrimental to you.

“So what does that leave? We kiss goodbye and never see each other again. We cry and move on, like people do everywhere when they have to. Or we play our kinky game to the finish.

“So let’s call today an audition. Let’s try living out that fantasy, and see how my little slut does as my guilty secret chambermaid. I think you might be surprised by what you find.”

Karl dropped his eyes. He shivered as a rill from his hair ran down his spine. Then the thought that after tomorrow he would never see Doreen again (unless he took to stalking her like a creep) overcame his recent unease. Why not play it out to the end, as she’d said?

“I guess I have been asking for this.”

“That you have, little slut. That you have. So, for your first taste of what it would be like living as my slave, we have this thrilling thing: seventeen dollars on EBay. Will that pay for a day’s fun, or be a lifelong torment? Only time will tell, I suppose…”

Doreen climbed off the vanity, opening a little box. Something silvery twinkled in her hand. Spreading Karl’s incapable-of-resisting legs, she actually locked a chastity device onto him, a small steel penis cage that the monster began raging futilely against at once.

“There: what’s a few months without coming when you can be a frustrated impotent forever? Just like the eunuch bed attendants of goddesses and empresses past. Of course they were castrated, so desire was minimized too. We want the opposite, don’t we my eternally deprived young sissy?”

She tickled the already swollen, protruding head of his trapped and straining mini-engorgement. Then she hung the small key on a charm bracelet she wore full of handcuff and shackle keys.

“Now then, my chambermaid for the day and maybe beyond, let’s get you all prettified and sissified. I want my little slut hot enough to fuck.”

Nurse Drake seated Karl with his back to the mirror.

She blow-dried and styled his hair. Using an electric curler, she gave him an explosion of slutty ringlets: true big hair in the late-eighties style. Then while Karl was wondering how long it would take for this to return to normal she started troweling on the makeup. When he fidgeted uncomfortably for the first time she cheerfully chided him.

“Hold still, little slut. I’m going to make you the hottest fuck in the state: Karla Jensen, Miss Sissy Teen Hawaii. I’ve been dreaming of this all year and I don’t want to screw it up. For every time you fidget, you will get five with the whip. That’s the first five. If you don’t want to explain to the stewardess why you can’t sit down, then obey your mistress and submit.”

Karl did his best. Still this wasn’t the old days when he had no choice. He was up to twenty-five lashes awaiting him by the time he was caked in cosmetics and had his toes and fingernails painted. She allowed him a single staggered look in the mirror, giggling delightedly and fondling his nipples while he gawped. Then she carefully fitted the ring-gag between his shiny, red-lacquered lips and buckled it up under his hair at the nape. After that she even more carefully blindfolded him with the eyeshade she’d brought along for sleeping on the plane. Taking his hand, she led him back into the bedroom for dressing.

Unable to see, Karl submitted docilely despite his growing discomfort as Doreen fitted a corset or girdle around his middle and tightened it until he was gasping. He felt the silk of the skimpy panties she pulled up his legs, and the way his caged genitals were slipped through a split in the crotch. When she slipped a finger after to rub his easily accessible sissy-pussy he gasped.

Stockings came next, clinging to his shaved legs in a way that made the monster rave in shameless if futile pain. These were clipped by frilly garters to his girdle or whatever, another illicit thrill he could admit to no one but his mistress. He earned another five lashes when she put the bra on him and slipped a pair of mangoes into the cups to simulate tits, but he couldn’t help himself; he just felt so sexy he had to squirm girlishly.

Finally she helped him into a very tight dress of some kind and a pair of hideously pinching shoes. Judging by the angle of his ankles these had extremely high heels, and he wondered how he was ever supposed to walk. Sitting on a chair pulled back into a corner, ‘Karla’ felt handcuffs snapped to his wrists in front and shackles locked about his ankles. Keys jingled as they were returned to his mistress’ wrist, and he devoutly prayed she wouldn’t get careless and lose any of those. A teasing hand reached under to pinch his protruding plum and then lightly ruffled his ringlets.

“Sit tight, my slutty little she-male. Mistress needs to make some work for you to do.”

Already having second thoughts despite the way his penis kept raving in its cage, Karl sat with his cuffed hands clasped demurely in his lap and listened to giggling and a growing ruckus as Doreen trashed their little cottage. Finally she returned to him.

Just as carefully removing the blindfold (it would be a crime to smudge those sparkly-shadowed eyes), Mistress Doreen reappeared. Now she was wearing a dominatrix outfit straight from his dungeon dreams: black leather open-cup brassiere with parabolas of chain draping her breasts and that matching harness about her waist, giant ivory already in place. Her boots were knee-high, with pointy toes and steel stiletto heels. She had her six-foot bullwhip coiled in one hand and a light of hilarity animating her gaze.

Karl looked down and saw another outfit from his dreams.

He was dressed as a sexy French maid all right. His heels were even higher than hers, the chain connecting his ankles barely a foot in length. As he burned and squirmed and wondered how he’d gotten into this, his chin and neck already slick with spit, Mistress nestled the lacy white headpiece into his curls. Then she seized his cuffed wrists and drew him tottering to his feet. Beyond her Karl saw that the cottage had been trashed indeed, garbage and spilled liquids all over the kitchen floor; clothes and cushions and sex toys strewn everywhere. Then his erstwhile lover reclaimed his attention by shaking out her whip.

“Let’s see, thirty, wasn’t it? Turn around, girl. Bend over and put your hands on the chair. Mistress needs to discipline you.”

Karl did as he was told, the old excitement rising if not quite so eagerly. He felt his flouncy little skirt flipped up and his panties pulled down. He could take thirty in his sleep.

That was what he thought at least. For some reason the pain seemed so much greater than before, or his masochism less up to the challenge. Perhaps it was the fact that his life no longer depended on it, or that he was no longer helpless and could escape if he chose, if only at great embarrassment. Whatever it was, the thrill of submission deserted him early on, and he was tested by those ten minutes or so as badly as hours with the cane. Then Mistress took advantage of his position to replay the dream that had healed him, taking him bent over with giant ivory so fiercely that it was atonement all over again. And of course his ‘audition’ was just beginning.

Karl spent all day hobbled and cuffed and ring-gagged, mincing around in his outlandish costume and painstakingly putting to rights what dervish Doreen had disarrayed in minutes.

It didn’t help that she was constantly interrupting him for sex or chastisement. He took giant ivory another half a dozen times and suffered every use of his sissy face in their repertoire – especially providing humbly kneeling toe and blow-jobs at whim. And whenever she wasn’t using him, or whipping or strapping or spanking him with her hairbrush, she spent her time ostentatiously masturbating.

Just listening to his person of worship screaming with release and calling out the names of a succession of phantom men was enough to torture Karl horribly with jealousy. It was bad enough knowing she was going to move on to other guys whether he was allowed to remain in her life or not. He didn’t want to think about that, much less listen to her simulate it. He couldn’t imagine being privy to any more than just this suggestion – or he didn’t dare to. Yet the worst, most appalling humiliations of all were still to come.

By the time Karl had finished his housework it was dinnertime.

All arousal had long been banished and he was increasingly miserable. He didn’t want to play anymore, and couldn’t believe he’d once fantasized about and even promised to spend his entire life this way. Still he made no protest, determined to play it out to the last. But even this resolve was tested when a knock came at the door.

Karl stood in the center of the main room, his cuffed hands bound above his head to a light fixture. His panties were around his agonizingly pinched and hobbled feet and his apron and detachable skirt stripped off to show his welts and caged penis. A bib of wetness spread from his lower lip all down the front of him, soaking the sexy uniform top stretched over his mangoes. Still carrying the whip she’d been using on him again, Doreen just smiled craftily and went to let whomever it was in, boots, chain-draped breasts, gigantic cock and all.

Too aghast to even consider the possibilities, Karl watched her stride to the door and open it. A guy about his own age was there carrying some cartons of take-out food. Doreen must have ordered out dinner, and here it was.

Though he was more outrageously humiliated than his worst experiences had ever hinted at upon seeing the appalled and derisive reaction of this peer of his, Karl couldn’t help but go limp in relief. He wasn’t sure what he’d feared, but this was just a deliveryman, and someone he’d surely never see again. Who cared what he thought? When the resident cougar didn’t seduce the guy right in front of him but flirtingly tipped him and then ushered him out again Karl was even more relieved. Relief of truly heavenly scope then arrived when Mistress Doreen set down the food and whip and lowered him to kneel beside her while she ate.

She removed the ring-gag and fed Karl a bite at time, both of them sharing mute, wistful acknowledgement of the thousand or more meals she’d fed him like this while he was helpless. Finally at the end the real Doreen breathed at him, and not the pitiless mistress.

“Yes darling, I’m going to miss that too. I’m elated that we healed you. But I loved having control over every morsel and drop to pass your lips. Speaking of which, I believe there’s one more part to this audition, one more duty my prospective slave promised to perform.”

Mistress stood and stripped off giant ivory at last. Karl mourned this. Seeing her striding around in that outfit, giant cock girded on and primed for dominance, was about the sole source of excitement left to him by now. But then she shoved back her chair, stepped forward and squatted, bringing her crotch down to seal against his mouth. Conditioned by duty, Karl poked out his tongue to penetrate her but Mistress stopped him.

“No girl, nothing so prosaic. This is where you live out another fantasy, yes? As I recall, serving as my helpless ashtray and human commode was to be an everlasting honor for my little slut. Are you ready to be baptized into the eternal service of your Goddess then? Spill not a drop of the nectar I offer and I will claim your cock-locked body and sissy soul forever!”

With only a second’s hesitation Karl lurched back away from her. Hand on the back of his head or no, Doreen let him go. She sat back down and smiled fondly at his abashment.

“Not cut out for slavery, are you darling?”

Face flaming, head whirling, Karl shook his head.

“No, ma’am. The lesson has been well and truly learned here. It was learned at least three hours ago in fact. Whatever I promised in my desperation and rapture, no matter what I owe you for housing me and loving me and healing me, I could never live that way.

“It’s odd,” Karl admitted. “A month ago I would have bathed joyously in your pee. I would have found a way to subsist on it and even love it. Not anymore.”

“I told you this would happen with your healing, darling. Your deep need to be demeaned and punished has passed. Now dominance and submission is returning to just a fun kink for you: a way to spice things up occasionally, but nothing to build your whole life around. At least not when you’re so young, freshly healed and with a world of possibilities ahead of you. Get out and live a little before you tie yourself too up in anything, that’s my advice.

“But now darling, my favorite and most rewarding patient ever, my most valued lover yet, we are reconciled with parting, are we not? As sad as it makes us, as much as we rue cruel fate, we accept that after tomorrow we will move on, taking our memories and the way we impacted each other’s lives so profoundly as our only solace.

“We will not seek each other out, or deliberately try to see one another. If our paths do cross, we smile and kiss over wonderful memories, we may even have a cup of coffee and catch up. But we resist the urge for further intimacy. We think back with pride and joy and love but we keep facing resolutely ahead. It’s the only way, my beloved boy.”

Even as she issued these orders Doreen was finally crying. Touched deeply by this rare weakening of her demeanor, Karl couldn’t help but join her. She took him cuffed and cross-dressed into her arms and they cried together, the sorrow they’d held at bay for so long overwhelming them at last.