[TG] Max's Long Night - Finale

Max is summoned to Madam Nightshade's chambers and finds his control slipping through his fingers.

~

To say that Max was nervous would be an understatement. After that final bombshell, Madam Nightshade had left, telling him he had an hour to make himself presentable for her. He bit down on his knuckle till it turned white; all night he’d been feeling conflicted, the emotions growing with each passing minute and now a veritable storm was raging inside him. There were so many angles to consider; he knew he could hold nothing back; he’d have to give this seduction his all or Madam Nightshade would never hold up her end of the bargain and turn him back. But it had been so hard to not give in completely to the pleasure of his new body and what was worse…part of him wanted to.

Yes, this night had started as a curse but he could no longer deny that Madam Nightshade had indeed picked him for a good reason. This body, this life; it was all something he’d fantasied about for years. Once he’d reached his late twenties, he’d out such dreams away, telling himself they were just fetishes he was better off ignoring. But now, after getting to fully indulge in them he could no longer push those confusing feelings down. Pandora’s Box had been opened and there was no going back. If he changed back, when he changed back, there would be a part of him that missed this body and all it could do.

But what else could he do? Give up his entire life? His entire identity? Just forget everything and become a thrall to Madam Nightshade? It couldn’t be done. He ran a hand through his luscious red hair, treasuring the silken texture so he could recall it later once it disappeared. The feeling was soothing and Max found himself calming down. He sat down at the makeup table, grabbing the hairbrush and began to run it through the long locks. The gentle tug massaging his scalp and turning the red hair ever shinier. With a sigh Max placed the brush down and put his chin in his hands, staring into the mirror.

The woman staring back at him was perfect; curvaceous, soft and undeniably feminine. Her long lashes framed her eyes perfectly without making her look permanently startled like his male body. Her roman nose actually suited her face now that it was heart shaped and the little mole on her left cheek managed to look cute, rather than like he had a permanent stain on his skin. She was everything he’d wished he could be all those years ago. Yet he couldn’t quite reconcile her with himself; his features where there, smoothed over, but there. She was him and not him at the same time.

Once upon a time, his mother had told him to act confident, even if he didn’t feel it and eventually, the act would become reality. Taking a deep breath, Max closed his eyes, snapping them open after forcing his face into one of serious confidence. The reflection in the mirror almost made his breath catch; the woman looked incredible, the fire in her eyes almost matched her flaming hair. A small smile tugged at his lips, perhaps his mother had been onto something there because a new sense of determination was slowly beginning to fill him. Right now, he didn’t need to worry about the past or future; rather he should focus on the here and now. And that meant showing Madam Nightshade what he was made of.

Full of focus he stood, walking over to the cupboard and flinging its doors open. His little satin dress was fine but for the Madam, he needed something special. He ran his fingers across a multitude of outfits, discarding the articles that were too modest or too skimpy, he needed something sexy, but classy. Finally, his hands stopped on a swath of dark green fabric. It was a bra and panties set, with a light, lace curtain hanging from the bottom of the bra to act as a sort of dress that would rest just above his knees. It was sheer, yet somehow didn’t look as vulgar or obvious as most sets of lingerie. The lace was patterned with whorls of flowers, a verdant garden made of fabric. Those swirls were stitched into the bra and panties as well and Max found his eyes widening and mouth splitting into a smile. It was perfect. He slipped on the panties, finding they sat snuggly atop his hipbones and fully cupped his hair. After all the punishment his pussy had already taken tonight the silken lining felt almost soothing. He expected the bra to be more difficult with its curtain but to his surprise, it almost seemed to float down to his body. The cup size was perfect, he could almost believe it was made for him. It even had strong support, keeping his breasts held high. It stopped the jiggling he’d grown so fond of, but ensured his cleavage was ample and on display at all times.

He rushed to the mirror, light on his bare toes and spun, watching the lace curtain spine around him. With his soft red hair, pale skin and green outfit he looked almost like a fey or something out of a magical tale. The perfect match for a witch.

The final touch was a layer of pink gloss across his lips, taken from the make up table. He pouted, carefully applying the lip gloss in the mirror, and noting that despite the strange, some would even say dangerous, situation he was about to walk into, his hands were steady. The nerves were there, of course they were, but they were mixed with excitement and defiance. He was ready.

He grit his teeth and allowed himself one last moment of weakness and doubt, hand poised on the handle to his temporary rooms. Then, with a deep breath, Max steeled himself and stepped out into the corridor and headed into the deepest part of the house. Follow some new, magical instinct to Madam Nightshade’s own door, emblazoned with a golden plaque bearing her name.

Just as his hand was poised above the handle the door flew open of its own accord. The room was on another level of luxury compared to what he had seen so far. Plush Persian carpets, dark mahogany furniture decorated with incense burners and silken blankets decorated the space. And in the centre of it all, a great, four poster bed the size of his entire bedroom. The sheets and duvet were a rich purple and sitting at its foot, was the Madam herself. She was wearing a white robe, yet somehow, the colour didn’t make her look innocent and pure. In fact, it had the exact opposite effect, clashing with her painted lips and sparkling eyes in a way that almost confused the senses.

“Hello, Maxie dear. So nice of you to join me and so punctual too.”

Max felt his mouth go dry as she uncrossed her legs, letting the robe slip down just that little bit to reveal a section of smooth skin. She held out a hand, nails painted wine red and beckoned him forwards. Max was unsure whether it was magic or sheer charisma that compelled him to obey but he did so. Everything about Madam Nightshade’s quarters seemed to lull him into a false sense of security; the carpet was soft as clouds on his bare feet, the sweet smell of incense filled his nostrils and melted the tension from his shoulders. By the time he’d reached the woman, only seconds had passed yet his eyes were already taking on a glazed, heavy-lidded appearance as the room seemed to work its magic on him. He felt loose and free and had to bite down on the inside of his cheek to refocus.

Madam nightshade’s hand reached up to cup his cheek in a gesture that could almost be considered motherly, were it not for the desire burning in her eyes.

“You really are lovely like this, you know.” She sighed, “I saw into your soul the moment you walked past. I saw your true desires and I have made them come true. Why fight it, Maxie?”

He swallowed.

“Because it wasn’t my choice.” He said finally as her fingers traced down to his chin, a single nail pressing gently on his lip as she cooed.

“My dear, my magic does not work on somebody who is not willing on some level. Were you truly against this, the pill would not have done a thing.”

“You’re lying.”

He knew she wasn’t.

Gently, she pulled down on his chin and Max felt his body bend to accommodate her so now they were face to face. She didn’t bother arguing with him, she could probably see the doubt in his eyes. Her lips were only an inch from his own now and instinctually his tongue flicked across the gloss he’d placed on his own; the sweetness there made his mouth water again and delight danced in the madam’s eyes. She said nothing, simply pulled him to her and kissed him deeply. Max felt his eyelids flutter closed; it was heavenly, better than kissing men or even Tabitha, it was slow, sensual and warm and without thinking he yielded to her.

A hand crept up the curve of his thigh and gripped his round ass, pulling him down onto the bed atop her. Despite the position Max had no delusions of being in control, he was here because it was exactly where she wished him to be. Her hands roamed, skimming across the flat expanse of his stomach and then up to his shoulder blades. Those long nails scrapped the lace into his skin and made him shiver before circling around the tiny hooks that held the article in place. With a flick of her fingers, they were gone and the bra fell off him and was swiftly brushed aside. Bringing both hands beneath him, she cupped his breasts, squeezing and massaging them gently as she pushed him up into a kneeling position. Max was in rapture; she knew exactly how to touch him to tease out the most pleasure. He could only tilt his head back to the ceiling and surrender to the sensation of having his nipples played with, desperately trying to keep that small part of him mind separate. He couldn’t look at her, it was too dangerous, yet with his head angled up his throat was bared and Madam Nightshade took advantage, gently biting into the sensitive skin and making Max quiver.

With her mouth on his throat and one hand on his breast her free one began to slowly move southwards. Max shuddered, his pussy clenching in anticipation and causing a small wet patch to soak into his pretty panties. Where had his defiance gone? Where was his determination not to give in? He tried, desperately to fight it but submitting to Madam Nightshade’s touch felt so very good.

“That’s a good girl.” She praised and approval made him whimper in pleasure.

A single finger pressed into the skin on his lower stomach, slipping beneath the thin waistband shaped like an ivy vine. Achingly slowly it moved across the red, curly hair there until it reached the front of his slit. Max’s breath hitched, his clit was less than an inch away and burned with desire. His pussy throbbed and his eyes flew open to find himself met with his own reflection. There was a mirror, suspended above the bedposts meaning he was now face to face with himself, kneeling amongst the sheets with Madam Nightshade slowly pleasuring him. He should look away, he knew that, but he couldn’t. Instead, he was met with his own reflection, face contorting in pleasure as she finally sunk a finger between his folds.

Her strokes were gentle and slow, spreading his slickness and coaxing even more from his wet hole. At first, she only glided over his clit every half dozen strokes, keeping him on the edge and only lightly brushing at his entrance. His reflection was blushing deeply, not just across his face but his shoulders as well. He was sure, were his vision not impeded by Madam Nightshade herself, that he would find that same blush across his breasts. He could feel the subtle burn there and it made him feel weak.

A desperate gasp escaped him when that finger finally pushed inside, the long nail gently scratching at his inner walls; it caused a slightly pain that only enhanced the pleasure that followed it and he moaned. He couldn’t give in fully though, he swallowed, biting his lip and trying to think of something, anything that wasn’t how incredible his body felt right now and how badly he wanted more. Her finger found his G-spot and pressed, causing another gush of juices and a whimper.

“Please.” He begged, unsure if he was asking for more or for her to stop. Either sounded like torture right now.

“Just relax darling, deep down, you want this. I am just helping you to see it.”

She rubbed against his G-spot, letting the sharp nail prick it occasionally and then soothing over the tiny pain with more pleasure. His resolve began to crumble and his hips bucked, once they started thrusting against her Max couldn’t bring himself to stop. Tiny gasps of pleasure escaping at each thrust of her fingers as his head finally fell forward to rest on her shoulders. He could now no longer see his reflection but instead had a perfect view of Madam Nightshade’s hand inside his panties, finger slowly thrusting into him. The sight made him want to wail. He was going to cum, there was no use fighting it but he refused to give her everything. He held out, squeezing his eyes closed and biting down on his lip as hard as he could as his pussy finally tightened and orgasm washed over him. The pleasure was immense but to his relief, Max still felt himself, he’d not given in fully! He’d won!

His elation did not last long though because Madam Nightshade wasn’t stopping. Despite his orgasm her finger was still pumping in and out of his hole steadily; his wet, overly sensitive hole. After so much use in a single night it was almost painful to have her still touching it. Ever nerve was on fire and Max found his breathing turning shaky from the mixture of torturous pleasure.

“You didn’t think I’d get you off just once, did you?” Madam Nightshade teased, “You’ve done so well tonight, Maxie. You deserve a reward after all your hard work.”

Max gripped her shoulders, nails digging into the skin as he tried, desperately, to ground himself. Her finger was still swirling inside him, slowly, teasing out the pleasure without fully overwhelming his senses. It was hard to think of anything else. He opened his mouth and all that escaped was a breathy moan.

“Unless, you want me to stop?” She offered, pressing her thumb to his clit and eliciting even more sounds.

She would stop if he asked, he knew that. If there was one thing he believed about the madam it was that she was a woman of her word. It was the smart thing to do, he had plenty of evidence to argue that he’d won their bet so she’d change him back. But it just felt so good, her touch was electric and deep down he knew holding back meant he was still to fully experience all this body could give. And he wanted it. Gods, he wanted it so badly, especially now that she was holding him right on the edge of it. He swallowed before his jaw went slack, she was still pressing her thumb to his clit and his pussy was starting to throb in tandem.

Max was at war with himself and slowly but surely, the side he’d so ardently tried to quash and deny was now winning. Madam Nightshade slowly pressed a second finger inside him, causing the inner walls to stretched and burn slightly with the added friction.

Max made his choice.

“Don’t stop.”

Max slumped against her, letting his body go limp and press against the older woman’s. He shivered as their breasts touched, the soft flesh pressing against one another, he could feel the hardness of her nipples through the dressing gown draped across her body. Then, remembering his daring, Max reached his hands up to part the folds of the clothing and slipped his hands inside to cup at those heavy breasts. They were bigger than his own, was and weight against his palms and the low groan that escaped the Madam’s mouth fuelled his curiosity. He pressed himself against her harder, rubbing their nipples together as a third finger pressed inside him, eliciting a wail. It was almost too good.

His body had already cum so many times tonight, it left his inner walls so sensitive and yet, somehow, ensuring that it took even longer for him to build to another orgasm. Now fully in the moment for the first time since his change, the pleasure seemed to increase and fill his every pore.

“No more distractions.” She whispered, nipping at the shall of his ear.

Moving a hand to the small of his back, Madam Nightshade gently maneuverer them down so he was laying on the sheets. He whimpered as her fingers withdrew, leaving him empty. His skin felt unpleasantly cold without her body heat against it and he whined, trying to sit back up only to be pushed gently back into the mattress. She slid down his body, hands coming to rest over his breasts while her mouth moved southwards. He barely had a moment to mentally prepare before her warm lips were against his folds. Max cried out, back arching into her touch and was rewarded with a sharp pinch to each of his nipples.

With hooded eyes he stared up at his own reflection; his skin now blush pink all over and eyes blown wide with arousal. The woman in the mirror was a wonton creature, pleasure etched into every line of her face. Max raised his legs up over her shoulders to allow her better access and her tongue dove into his folds. Already slick with juices it glided back and forth before finally dipping into his hole. Max was sure the whole street must have been able to hear him by now; he couldn’t hold back his cries any longer. He writhed, letting the pleasure fill him completely; he was aware of every inch of his skin in a way he’d never been before. He could feel the touch of her hands and tongue on his most sensitive parts, but also the soft, silk sheets at his back and the increasingly hot air on his face.

His insides were beginning to coil, a now familiar tightness forming in his core as he slowly got closer and closer to the edge. The world faded to a single place and time; all he could think about was Madam Nightshade’s touch and how good his body felt. If this was to be his fate, he was more than okay with it. His back arched once more as he came, wetness flooding out of him and onto the Madam’s face where she lapped it up. The ecstasy was so intense it made him feel lightheaded. As he collapsed back into the sheets Max watched as a haze descended over his mind and his life flashed before his eyes. Except this time, it was different; the Christmas’ where he watched jealousy as his sister received dresses melted away, replaced with ones where he too was granted them. His lonely high school days in the chess club replaced with happier times, as part of a cheerleading squad. His life was being rewritten before his very eyes, so that Max never existed but Maxie had.

She wasn’t sure how long it took to catch her breath and come down but when she came back to herself, she was snuggled up against Madam Nightshade. The older woman was stroking her hair gently and Maxie shivered, relaxing into the touch.

She was drowsy, almost dizzy, though that was to be expected; Madam Nightshade was the best lover she’d ever been with. It had been so long since she was last in her bed that Maxie could scarcely remember it, so many months of average men could jade you, make you forget just how much pleasure you were capable of feeling.

“How do you feel, Maxie dear?’

“Good, as always. I’ve missed you.”

Madam Nightshade chuckled.

“Of course, dear, but you’ve been working so hard lately I thought you deserved a reward.”

She had, hasn’t she? Everybody assumed working in the red-light district was an easy job where she just had to lay back and let the men do all the work. But the truth was, she put a lot of effort into pleasing every client the madam sent her way, it was nice to be the one focused on for once. She hummed thoughtfully to herself, remember all those years ago when she’d first come here and began working. How lucky she had been, that Madam Nightshade picked her from the crowd; if she hadn’t who knew where she would be now?

~

Two Years Later…

Life at the Velvet Cage had never been so hectic. It seemed as though half the city tried to get through those doors each night. Maxie went to sleep each dawn exhausted from a full night of clients, but couldn’t bring herself to be upset about it. She was the most requested girl in the house, Madam Nightshade had even set up a waiting list and appointment system just for her.

“You’re so lucky.” Tabitha sighed one evening as they took a break between sessions, “I can tell half the clients that get sent my way were hoping to be with you.”

Maxie blushed at the compliment; she couldn’t help her strange intuition when it came to where and how to touch men to elicit the most intense pleasure. It was almost as if she had felt it herself once, perhaps in a dream. Not that she’d ever want to really be a man, she’d have far less fun.

“Ah, just the girls I was hoping to see.”

Madam nightshade entered, her large manicured hands guiding in an unfamiliar face. The woman was Rubenesque, with large curves and short blonde hair that made Maxie think of the old pinup posters from the 1950s. She was blushing a deep crimson and covering her scantily clad body with her thick arms; almost as if she was ashamed of it.

“This is Rosie.” Madam Nightshade introduced, “It’s her…first night.”

“I um, actually prefer Ross.” Rosie squeaked and Maxie giggled; why would such a lovely creature choose to go by a man’s name?

“These are two of my best girls, Maxie and Tabitha.” Madam Nightshade continued, “I recruited them the same way I did you.”

Rosie’s mouth dropped for reasons Maxie couldn’t comprehend, what was so strange about the Madam picking you from a crowd.

“You mean they were both-“

“Yes.” The Madam cut her off, “Maxie, why don’t you take Rosie back to your room and help her relax a little. You do have such a good record when it comes to recruitment.”

It was true, Madam Nightshade often sent her newer recruits to pleasure before they took on their first client, it made them feel less nervous about using their bodies for pleasure. The girls she sent back to the madam always seemed so much happier and at home than when they first arrived. It was one of her favourite jobs, plus it gave her a break from men once in a while.

Gently she reached forward, taking both Rosie’s hands in hers and holding them tight; smiling warmly as the blush across her cheeks deepened.

“Come with me, I’ll take good care of you.”