[TF/TG] Max's Long Night (Patreon)

Personal Touch Tier Reward for DeSaJo

Max heads to a brothel to spend the evening forgetting his woes but soon finds himself unexpectedly recruited by the mysterious Madam who runs it.

~

Max refreshed his screen for what felt like the hundredth time. His dating profile had been live for weeks now and still not a single message. There was no denying his pride was bruised; sure, he wasn’t the best looking guy on the market but he was far from the ugliest. His eyes looked over his profile picture; he’d expected the baldness to be a turn off for some of the more superficial ladies out there but his red beard was neatly trimmed and with that soft smile he looked warm and approachable. He’d expected one or two hits at least, surely that was not too much to ask.

With a sigh, he rubbed a hand against his rough cheek. He knew from experience that spending the night staring at this screen would do nothing to improve his mood. He’d gone into this endeavour cautiously optimistic but that had long since faded; there was something about passing thirty while still perpetually single that just made his whole life feel that bit greyer. Especially when it felt like his colleagues were announcing an engagement every other month. He wasn’t even asking for that, he just wanted somebody to come home to so he could stop relying so much on his own right hand.

He glanced out the window, gaze drawn to the bright glow of neon a few blocks away. He was too old for the red-light district really but a man can only take so much rejection. Fuck it, he wanted a distraction dammit and he was sick to death of the porn saved on his computer. Grabbing his coat, he flipped up the hood and set out into the night.

~

It had been years since Max last ventured here; in his late twenties he’d sworn off whores in favour of finding a ‘proper’ woman whose affection he did not need to pay for by the hour. Even so, there was something almost comforting about the street with its lewd signs and half dressed women in the windows, there was no judgment from his fellow passers-by either, they were all here for the same thing after all. The names changed but every establishment was pretty much the same, he was going to simply pick one at random when a flash of red caught his eye.

A surprisingly subtle sign of black and red wood hung above an ornate doorway style to look almost medieval; The Velvet Cage. The building was made from dark bricks with thick iron bars across the windows in line with the name, the door opened and an older woman in a black dress stepped out. A madam, is the appropriate term Max supposed, a mature beauty of dark skin and soft brown curls with the most impressive cat eye mascara he had ever seen.

“Hello, dear.” She purred, “Why don’t you come on in? I do believe you’d be a good fit for our establishment.”

Max mentally shrugged, this place was as good as any he supposed, at least they had good customer service and a cool theme going on. He approached and to his surprise the madam reached out with pointed nails and rested them beneath his chin.

“What a handsome beard.” She cooed, “Such a beautiful shade of red…”

“Thanks.” She was likely just trying to butter him up but he blushed all the same.

“Come on in darling, I know just the woman for you.”

You couldn’t fault her people skills, that’s for sure. Max followed her in, desire and anticipation slowly building as he stepped onto the plush carpet of the foyer. The room was heavily scented with flowers and spice, it instantly relaxed him and he quickly signed the register without a second glance. Later, he would realise that she never asked for any payment.

“Max, what a beautiful name.” The madam cooed, “My name is Madam Nightshade, I think my girl Tabitha would be an excellent fit for what you are after.”

Max opened his mouth to retort her, he hadn’t even mentioned what his tastes were but found the words stopped dead in his throat. A woman appeared as if by magic from behind a silken curtain door, she was exquisite. Honey coloured hair, vivid blue eyes and sun kissed skin were only the beginnings of her beauty, Max found his jaw dropping as he beheld those pouted pink lips especially, her outfit was so unlike most whores, who favoured tight leather and skimpy bras. Instead, she wore a loose, flowing blue skirt and matching bralette, she looked almost like some sort of mermaid. The comparison continued as she stepped forward to greet him with a demure smile, long skirt almost totally concealed her legs and giving the illusion of gliding across the floor.

“Tabitha, this is Max.” Madame Nightshade began, “I want him to have your very best treatment, understand?”

For a moment the blonde looked startled as some sort of silent exchange passed between the two women but then she quickly regaining her composure.

“Very best.” She nodded, “I understand, ma’am. Come Max, let me take care of you.”

Fuck it, he didn’t care if this was all an act, it felt nice having a hot woman speak to him like this. He felt his cock twitch in anticipation, he just hoped he could at least last a decent amount of time; it had been a while, the last thing he needed was to cum in his pants like a teenager. Tabitha rested one soft hand on his chest, the other taking up his own and giving it a gentle squeeze before leading him through the curtain to a dimly lit hall lined with doors not unlike a hotel. They each had a golden plate emblazoned with a name at their centre, when they reached the one labelled ‘Tabitha’ she smiled and nudged it open with her hip.

The room was far more opulent and comfy than most whore houses, with a generously sized bed shrouded by silk hangings. Tabitha led him to it, gently indicating he sit at the foot while she stood over him.

“What sort of girl do you want me to be tonight, Max?” She asked, almost sweetly, and he felt a nervous lump form in his throat as his cock began to harden staring at those soft pink lips.

“I’m uh, not sure, any recommendations?” God, that was so lame.

“I’ve had a lot of practice being all sorts of girls.” Tabitha giggled, “But I think you’ll like the loving girlfriend experience.”

She lowered herself, half crawling into his lap as she said it, her bust flush against his chest.

“That sounds good.” He whispered a moment before their lips finally touched.

Her mouth was silky and warm against his, lips and tongue pliable, yielding to him without question. It had been such a long time and yet he found himself navigating the experience expertly if Tabitha’s contented moans were anything to go by. Those soft fingers ran through his beard, nails gently scraping against the skin beneath and sending a pleasant tingling across his face. He couldn’t help but groan in gratification, it had been such a long time since he’d done anything like this.

Tabitha made herself at home in his lap, legs curling around his back, pushing her groin up against his hard cock. Even through his trousers he could feel the warmth of her as that long skirt bunched at her hips, a subtle glance down revealed she wasn’t wearing any underwear. He bought his hands up to rest against her bare back. Fingers running along the curve of her spine from shoulder blades to the roundness of her ass. Max enjoyed the way his touch made her shiver. Her body was magnificent, feeling it against his own filled him with both desire and a little bit of jealousy which he quickly buried.

Tabitha began to unbutton his shirt, slipping out of his lap slightly in order to kiss at each new inch of skin she revealed before gently pushing it off his shoulders. Her touch was almost reverent, she showed no signs of haste, in fact, she seemed to be savouring the experience just as much as he was. She gave him a warm smile, stepping back far enough to wiggle her wide hips free of her skirt which pooled on the floor and was instantly forgotten. He could see genuine wetness glistening between her legs and his hardon became almost painful. She returned to him, gently pushing him back to lie down as she removed his belt and divested him of his trousers as well.

He sighed in relief as his erection was finally freed from confinement, already dripping with precum. The foreplay had been soft and teasing, almost like they were genuine lovers but he was beginning to feel the lust take hold in his mind. Seeing her wet pussy fully on display as she crawled back up his body to continue their kiss was almost too much to take. He could feel her hovering above him, juices occasionally dripping down against his bare skin. He groaned, kissing her passionately and laying a hand across the curve of her ass to guide her down upon him. His eyes and mouth opened wide with shock and pleasure as she slowly sank down his shaft. Tight heat slowly engulfing his cock and squeezing it tight until she was flush against him, his tip pressing up against the deepest part of her and she moaned.

Gently, Tabitha began to rock her hips and he revelled in the tightness that surrounded him, he could almost cum from this alone. A breathy, desperate sound escaped Tabitha’s mouth as she began to rise up before descending again, keeping the movements shallow at first before slowly drawing away more and more with each subsequent thrust. Max couldn’t help but buck his hips up into her, causing her whole body to jerk and writhe. He could see the genuine pleasure on her face and it fed his own, the fact that he could give her such feelings made him feel more powerful than he ever had.

He could feel orgasm building within him but he tried to keep it at bay, he didn’t want this to be over yet. The pleasure radiated out from his cock and slowly began to fill his entire body, everywhere Tabitha touched seemed to radiate it. She leaned back, bracing herself on his legs and arching her back so that her breasts bounced with each thrust. He watched them rise and fall as she moaned before slowly lowering his gaze to her pussy. Watching her ride him, his cock disappearing into her tight folds at an increasing pace as they both raced to the edge. It was too much; he felt his balls tighten and he threw his head back as his cock pulsed and he came. He could feel that warm seed spilling out of him and flooding her as she came around him, squeezing his shaft so hard it almost felt as though he were being sucked dry.

He flopped back against the bed, exhausted and still reeling from the strongest orgasm he’d ever experienced. Tabitha leaned back over him, still holding his softening cock within her as she took a small object from her silken bra and placed it in her mouth. Before he could ask what it was she had leaned back over him, placing those soft pink lips against his own and forcing her tongue inside. He felt something small and smooth, some sort of pill perhaps, pass between them before she withdrew, a hand against his neck.

“Shhhh, swallow.” She whispered, massaging his throat so that he couldn’t help but comply.

“What did you just give me?” He balked.

“A gift, from our Madam.” Tabitha replied, finally dismounting him with a shudder.

She got up and headed for the door, he sat up to demand further answers but the words turned to a pained groan as his guts seemed to twist. Max wrapped an arm around his stomach as the twisting continued, stumbling forward only to find Tabitha had taken his clothes with her when she left. A wave of dizziness passed through him and Max felt himself fall to his knees, had she drugged him? A strange feeling, like pins and needles began to itch at the skin on his face. He bought a hand up to scratch at the skin and was immediately shocked to find less than he was used to. Placing his palm flat against his cheek he was shocked to feel the hair of his beard moving, actually regressing back into his skin! That same tingling appeared atop his head and when he moved the hand to meet it, he found the opposite was happening, long strands of soft hair were sprouting from his skull! What the hell did she give him?

Panic building, he stumbled back to his feet, rushing for the door only to find it locked. He pounded at it, yelling for answers but nobody answered his calls. He kept going, bashing his fist against the hard wood only to freeze when he realised his hand looked…smaller. He took a step back, taking in the delicate features that were slowly replacing his own. The fingers were dainty and smooth, not a trace of reddish hair to be seen. His breath was coming in short bursts now as his alarm grew, he pulled his now dainty hands against his chest in an effort to slow his racing heart but instead found yet another shock.

His chest was soft, slightly swollen and far more sensitive than he was used to. With trepidation he looked down, finding two small rapidly expanding mounds where the flat plane of his chest had once been. He knew what he was looking at but it didn’t make any sense! Breasts, round and heavy, were swelling to life. His chest hair gone and instead two pink, pert nipples were proudly poking forward. He grabbed handfuls of the new boobflesh, half expecting it to not be real but it was, he could feel the skin yield to his touch.

Everywhere was changing; his lips were plumping, eyelashes growing and most noticeable of all, outside the breasts, was his ass. It too was inflating, creamy skin becoming round with his widening hips to form a beautiful peach shaped ass that jiggled with each movement he made. He placed his hands upon it, feeling that delicate curve and marvelling that it belonged to him.

By now his hair had finally stopped growing, those long, luscious red waves reaching just past his shoulders which were now sloped and lady-like. His panic abated somewhat, being replaced with bewildered fascination as he twisted and turned trying to take in each new detail of this form. His creamy skin was tinged pink in places and a beautiful red mound of curly hair sat between his legs. He was just about to reach a finger down to part said hair when the door finally reopened and he jumped in shock as Madam Nightshade appeared with a warm, almost victorious grin on her face.

“Ah, I knew you would be a perfect fit for our little family.” She smiled, “Welcome, Max.”

“Wha-What have you done to me?” Even his voice was different, gentle, with an almost songlike lilt.

“Just a little curse darling,” She smiled, “It’s what us witches like to do. I have to get my kicks somehow and I choose to do it in such a way that we both get some pleasure out of the bargain.”

“What do you mean? I never struck a bargain with you!”

“You’re about to.” She walked forward, circling him like a lioness toying with her prey. “How about a little wager, Max. Work for me in my house tonight and if you can withstand the pleasures of your new female form, I will turn you back.”

She ran a hand along his hip at the word ‘pleasure’ and it sent sparks flying across his skin.

“Do this and when the sun rises, you’ll walk out of here the same man you entered but if you give in and admit you’re really a woman, I’ll do as I did with Tabitha and all my other girls. Your memories will be changed and you’ll forget you were anything other than this.”

“Tabitha was…?”

“A man once? Oh yes. She turned out quite well, didn’t she? So loving.”

Madam Nightshade’s hand rose from his hip, up the slope of his body before coming to rest under his chin, gripping it firmly so that he had no choice but to meet her gaze. Purple light seemed to shimmer behind those dark eyes and he found himself mesmerised by the light.

“What do you say, Max?” She whispered huskily, “Do we have a deal?”

What else could he do? He was completed at Madam Nightshade's mercy; without her magic he would never be himself again.

“Yes.”