[TG] Max's Long Night - Part 3 (Patreon)

Personal Touch Tier Reward Story for DeSaJo with extra length commissioned 

Max begins to experiment and explore his new body as he takes on another client. 

~

Max sat at the make-up table, hands nervously fiddling with his short satin hem as he waited for the inevitable call. He wasn’t sure how long it had been since Madam Nightshade left; his thoughts had been all consuming; memories and emotions swirling in his mind. Lacking any better distraction than picking at the dress stitching Max picked up the hairbrush somebody had left on the dresser and began running it through his now long, red hair. The gesture was almost calming, the bristles slowly unknotting the strands and making them shine. He wondered if that is what Madam Nightshade had meant when she said he was special; she had complimented his red beard when he first entered after all, perhaps she was missing a redheaded girl in her collection? No, there was something more to her insinuations he knew it. Again, those memories of his youth bubbled up, the jealousy at his sister for her gifts of make up and high heels. Once again, he quashed them; youthful indiscretions, nothing more.

There was nothing weird about admiring how good this body looked and felt; under it all he was still a man after all. He was probably just feeling weirdly attracted to his own reflection, after all it wasn’t really him. Yes, that was it. And giving that blow job was just curiosity! His enjoyment derided from was simply derived from the novelty of the escapade. This was a whole new experience and he was making the best of it, that was all. Max bit his lip; that had to be it. It had to be.

The tinkling of the bell above his door bought both trepidation and excitement, the latter of which he tried to extinguish out of shame. Max knew he wouldn’t be able to get away with just a blow job this time. He swallowed, hopefully it wouldn’t be too painful, perhaps he should have spent this time looking for some lube to make things easier. Oh well, too late now, he was being summoned. Nervous as he was, he forced himself to appear confident, men liked that in a woman, the quicker he could finish the guy off the better. He let his hips sway as he walked, taking long strides with those smooth legs. Why shouldn’t he hold his head high? He’d done a good job with Rob after all, if nothing else he had some skills he could fall back on.

Pulling back the curtain he was met once again with Madam Nightshade and a man, this one tanned, with dark black hair and brilliant green eyes. He was waring a sort of casual business suit; trendy and sleek, certainly not the sort of man you would assume frequented ladies of the night. Max felt his heart beat quicker in his chest and his palms began to sweat slightly. A moment later he felt the familiar sensation of desire pooling in his lower stomach and he almost balked, he was attracted to this man. From the appreciative look he gave in return, Max assumed the feeling was mutual.

“Oh yeah, she’s perfect.”

Despite himself Max blushed, nervously fixing a stray strand of hair that fell over his face as he looked down.

“Maxie is a wonderful girl.” Madam Nightshade cooed, “She’s really started coming into her own tonight, I am sure you will have a lovely time with her.”

Max offered his hand, his cheeks flushing further as the man took said hand and kissed it like a prince from a fairy-tale.

“Enchenté, Maxie. I am Gregory.”

“You’re…certainly quite the gentleman.” Max smiled nervously, trying to ignore the way that touch sent shivers up his spine. He had to get a hold of himself.

“Oh, just so you know, Maxie dear.” Madam Nightshade added with a sly smile, “Gregory here has paid for a double booking, twice the time, twice the acts.”

Mac hoped his client didn’t see his nervous swallow. Gripping the man’s hand firmly he walked them down the corridor to his temporary room, desperately trying to get his damn heart under control. This had never happened to him before, okay he’d occasionally considered what it would be like to be with a man as a woman but that was very different from actively desiring somebody. Of course, Gregory was attractive on an objective level, with those bright eyes and strong jaw. What woman wouldn’t fancy him? This had to be Madam Nightshade’s magic, her attempts to get him to give in the pleasure of his new body and win their little bet. Well, jokes on her, Max had a stronger will than she gave him credit for. As soon as the door to his room closed Gregory seemed to relax, letting out a deep, world weary sigh.

“It’s been a long week.” He explained, tugging off his tie, “I just want to let off some steam, y’know?”

“Of course.” That was what had bought Max here himself. “How do you…want me?”

A subtle dampness was forming between his legs, watching this man undress. Max’s eyes roamed over that muscled torso as Gregory shrugged off his business shirt, he even felt his knees weaken slightly as the man shot him a cocky smile. Keeping his desire in check may be, ever so slightly, harder than Max thought.

“First, I want to touch you.” He ordered, “Strip for me.”

That wasn’t hard, he was barely wearing anything. In a manner he hoped came off as sensual Max slipped the negligee off his shoulders, letting the dress fall around his ankles while Gregory prowled around him.

“Oh yes, very nice.” He purred, cupping both of Max’s breasts in his hands and making his heart stutter.

“Good to see a girl with some curves.” His hands smoothed over Max’s tits, sending lightning forking through his entire system.

He tried to focus on the wall behind Gregory but his eyes kept slipping back to meet the man’s gaze, it was so intense. So enticing. Before he knew what was happening Max’s body was moving on instinct, mouth open to press against Gregory’s own in a deep kiss. The man moaned into Max’s mouth and the sound made the wetness between his legs increase. That hole inside him began to ache ever so slightly, yearning to be filled. Gregory’s hands found his ass and Max couldn’t help but yield as he was lifted off the ground, he wrapped his long legs around the man’s torso, pressing that wet hole against his crotch and feeling the bulge there; the only thing between them the thin material of those pants.

Everywhere they touched was electric, he couldn’t help but cling to Gregory as he was carried, enjoying the feeling of weightlessness. Max was in control, he just needed to get this over with and let Gregory fuck him. He tried to ignore just how badly he wanted that as well, at the very least his body did. Gregory placed him down on the bed, gently turning Max’s hips so that he was on his hands and knees facing the headboard. This was good, at least if they did it doggy style, Max wouldn’t have to look at the guy while they fucked. Looking at those eyes while Gregory moved inside him…just the thought made him whimper. Gregory gently pressed a palm into his back, forcing him down into the sheets while raising his ass into the air. The submissive position sent a shiver up Max’s spine; his fingers gripped the silken sheet in anticipation. He could feel his wet pussy exposed to the air, folds parted and open, already dripping and ready. His worry about needing lube was very much unfounded it seemed, this body was ready made for sex. The notion sent a thrill through him.

Gregory was taking his time, running his fingers up and down the curve of Max’s spine, stroking his long hair and sliding his palms under his body to cup those heavy breasts. Each movement left warm trails on Max’s skin and he had to resist the urge to keen. He leaned into those touches, telling himself it was all for show and doing his best not to focus on just how deliciously good it felt to have his nipples stroked. Juices flowed between his legs with each touch and that ache inside him was almost painful; Max could feel himself getting desperate, the want to have something inside him slowly turning to a need.

Finally, there was the sharp sound of a zip and Max felt the tip of Max’s cock pressing against his hole. Despite himself, Max tensed, waiting for the pain of being penetrated but it never came. Instead, a wave of overwhelming gratification and bliss overtook him as Gregory slowly pushed inside. His cock stretching and pressing against Max’s soft inner walls sending sparks flying through his entire body. It was heavenly. Max felt his jaw drop open in shock and pleasure as Gregory finally pushed them flush together, Max could feel the scrape of his hair against his outer folds. Then it was gone, Gregory having pulled back only to slam back inside again, eliciting a cry from Max before he could stop it. The gesture was repeated, then again, over and over, each time the force of the thrust and ecstasy it created knocking the wind right out of Max’s lungs.

It was so good. He was forced to bite down on the mattress to stop from begging for more. Every few thrusts the tip of Gregory’s cock would brush against something deep inside him, making his vision white out as his mind was overwhelmed with the sensation. He was desperately trying to hold back; he wasn’t sure what constituted ‘giving in’ but he was sure he was close to it. There was something building deep inside, a sort of pressure he knew would reach its limit if this continued much longer. His hips rocked back to meet Gregory’s thrusts instinctually and once he’d started Max found he couldn’t stop, the pleasure the movement created was too difficult to resist. Together they found a rhythm, their bodies moving in tandem and Max felt his jaw going slack as his eyes began to glaze over. He could think of nothing but how good each thrust felt; pulling himself back from fulling giving in to that pleasure was indescribably difficult.

Gregory’s moments were becoming erratic, Max could tell he was getting close, as was he. Max squeezed the cock inside him hard and Gregory groaned before he pulsed and a different kind of warm wetness flooded Max’s pussy. Max gasped, he’d come so close to orgasm and his body was screaming for it. That ache inside him had been reduced but not sated and he couldn’t help but whimper slightly as Gregory pulled out. He should have been happy it was over but instead he felt disappointed. Disappointed and hungry in a distinctly primal way.

“Fuck, you’re brilliant.” Gregory groaned, “Glad I paid for a double round.”

He flopped down onto the bed, arm over his eyes with a contented sigh.

“Give me a minute and I’ll be ready to go again.”

Max swallowed, feeling his breasts rise and fall with each deep breath he took. His nipples were hard as rocks, aching to be touched and his pussy quivered at the knowledge that soon it would be filled again. He tried to muster up some shame or embarrassment about how he was feeling but couldn’t seem to manage anything but eagerness.

He bit down on his tongue in an effort to reign himself in. Trying to focus on the sharp pain rather than the lingering pleasure radiating across his skin. He needed to take control of this situation, fully. It was time he stopped being some meek little puppet in Madam Nightshade’s sick game. She was going to show her and Gregory exactly what ‘Maxie’ was capable of.

With confidence he hadn’t felt in years Max crawled over to his client, placing a knee either side of his hips and stretching out his sore back. He could feel Gregory’s cock twitch watching his now lithe body displayed above him before gently, Max lowered himself down. He rested their foreheads together, licking at his lips in a way that he hoped would seem sexy, not nervous. He shivered as those pert nipples brushed against Gregory’s smooth chest, the friction causing the pleasure to start anew.

“You’re eager.” Gregory teased; Max could feel his hot breath on his face.

“Couldn’t wait.” He murmured in reply, unsure as to whether it was a lie.

He could feel Gregory’s cock hardening below him, slowly rising before coming to rest against his dripping hole. From this position, with Gregory pinned beneath him and Max could control everything. He wouldn’t be losing control again. Still, a ragged moan escaped his lips as he sunk down on the shaft, jaw once again dropping as the sheer intensity of the sensations short circuited his brain.

For a moment he simply sat there, feeling the cock inside him before he rocked his hips experimentally. This wasn’t like being on top as a man, each movement, no matter how slight, caused his inner walls to be teased. There were so many ways to shift, each one creating a different flavour of pleasure. Max couldn’t help but experiment, shifting his hips back and forth before finally rising and sinking back down. The feelings were exquisite and Gregory’s hands gripping his wide hips grounded Max to this reality, stopping him from falling completely into a haze of pleasure.

He looked down at the man he was riding, fully intending for it to be a quick glance but found his eyes glued to the muscular form. His abs and shoulders were clearly defined by a thin sheen of sweat from their earlier bout, his eyes bored holes into Max’s very soul. He couldn’t look away. Gregory’s face was one of rapture and Max felt a thrill pass through him; he was doing that; he was the source of that bliss Gregory was feeling. The power he held over this man was…intoxicating. He wanted more.

He began to ride harder, feeling his breasts bounce along with him. He felt a smile form as Gregory’s eyes dropped to watch them, he looked almost hypnotised by their jiggling, it gave Max a feeling of power he’d never experienced before. Once again, he bit down on his lip, he thought being in this position would help him stay in control but it seemed to be doing the opposite. He was getting even more turned on watching Gregory writhe below him. He leaned away, intending to stare at the ceiling or find some other distraction from the bliss but instead he found more. That deep place inside him, the one Gregory had brushed against a few times during their first round, he found it.

Leaning back as far as he could, bracing his arms against Gregory’s legs Max moaned. In this position that place of deep pleasure was being stimulated constantly. With each rise and fall Gregory’s tip rubbed against it, sending wave after wave of pleasure shooting through Max’s body. He knew he should stop, should find a better, less wonderful position but he couldn’t; his body ached for orgasm and he knew it wouldn’t be far away if he kept doing this. His back arched, breasts thrust out as he continued to ride cowgirl style close and closer to the edge.

“Oh God I-‘m close-!”

Gregory gripped Max’s hips tighter, he used the pressure like an anchor as he felt himself cresting. If he could just keep part of his mind focused on that and not the bliss…he wouldn’t give in completely. Max could hear himself moaning, each one becoming breathier as he raced toward the edge, there was no stopping it this time, finally the dam broke.

Max cried out as pure ecstasy filled his every pore; he was almost screaming with the intensity of it. Wave after wave of delicious sensations poured over him, the only break being that tiny speck of his mind focusing on the painfully tight grip Gregory had on his hips. It was so unlike any orgasm he’d ever had as a man, it just seemed to keep going, even as Gregory came as well Max couldn’t stop himself for milking every last drop out of his partner. After what seemed like almost a full minute he shuddered to a stop, pussy still throbbing with a new, smaller wave of pleasure every few seconds.

He breathed a sigh of relief and exhaustion, he still knew who he was; as wonderful as that had felt, he must not have fully given in to the pleasure as he still remembered who he really was. Even so, he felt the loss as he raised himself up and Gregory left him. Max’s legs were soaked with cum and juices, the sensation left him feeling a kind of satisfaction he’d never known, he almost didn’t want to clean it off.

“Wow, Madam Nightshade wasn’t kidding, you are well worth your price.”

Max resisted the urge to ask just how much the man had been charged for his services. His mouth felt dry as the gravity of the situation began to crash down on him; he’d nearly lost it there, he’d come a hairs breath away from losing himself completely.

“Glad you enjoyed yourself.” Was all he managed to murmur, laying back in the silken sheets while Gregory dressed himself.

“You know, I’m a team director at my company.” He mused allowed, “I’m so used to holding the reins, it was nice to let you do that the second time around, maybe I should let ladies do that more often.”

“This place has a habit of revealing aspects of yourself you didn’t know you had.” Max replied dryly, staring at the ceiling, his own words echoing around in his skull.

Gregory thanked him once again before showing himself out, leaving Max alone on the bed, still a mess from their coupling, both physically and mentally. He should be ashamed of himself, acting that way, enjoying this body the way he had; but he just didn’t. He thought about the confidence he’d felt, the power and pleasure this body had gifted him with. It was something he’d never experienced as a man. Not to mention his beauty; Max had never hated his old body but he was under no illusions it was anything special. Not like this one; he ran a long finger across the curve of his hips before tangling it in his hair. It had been so long since he’d had hair on his head, and even then, it had never been so luscious and beautiful.

He was beautiful now. He liked that.

After a few minutes of quiet contemplation, he sat up, the mess on his skin was beginning to crust and harden and he grimaced at the sight. Fortunately, his room had an ensuite he was yet to use. Hopefully he had time for a quick shower before Madam Nightshade called upon him. The small bathroom was tiled black and red with gilded gold taps and facets. The small seat located within the double wide shower told him that shower sex must have been common amongst Madam Nightshade’s other girls. Trying hard not to think about all the potential acts performed in this very space he hopped into the shower and sighed as the warm water hit his skin, washing away the sweat and other mess from his night’s work.

Max couldn’t help but marvel at how even something as mundane as taking a shower could feel so different as a woman. He could feel the water flowing over his breasts and down the curve of his body; trails of it spreading across his hips and down his thighs. His skin was still sensitive from the sex, his nerves dancing under the water’s stimulation. He dipped his head beneath the stream, enjoying the heat as steam opened his pores and soaked through his long hair. He could stand here for hours but knew better; with much disappointment he turned off the spray and stepped out onto the plush mat.

Quickly he dried himself with one of the white towels available, even attempting to bunch up his hair up turban style as he’d seen many girlfriends do in the past. He failed miserably, doing nothing but tangling the wet strands around his face. Idly he wondered what styles he could achieve with hair this long; how would it look in a braid or topknot? He’d just left the bathroom, intent on picking a new outfit when a knock at the door made him jump. Max had just enough time to pull the towel around himself before Madam Nightshade let herself in. She looked confident; Max felt his stomach flip at the hungry look in her eyes. Her ruby red lips were curved into what was Max was quickly considering her signature smile.

“How are we doing, Maxie.”

“Still Max.” He responded flatly.

“That’s not what I meant and you know it.” She purred, “How was your time with Gregory? He seemed very satisfied and I take it, from those stains on the sheets, you are too.”

“It was fine.” Max blushed deeply; glad he had showered to rid his body of evidence that proved just how ‘fine’ things had gone.

“My dear, have you figured out why I picked you for this yet?”

Max bit his lip. He had a sneaking suspicion, she was magical after all, she could know…

“Because I’ve fantasied about being…this?”

Madam Nightshade nodded.

“I can sense what a man wants, it’s why I am always so good at pairing my girls to clients.” She told him, taking a seat at the edge of the bed. “And sometimes, when I look inside their hearts, I see desires and fantasies they wont even admit to themselves.”

“Look, that’s nice I guess but just because I went through a bit of a phase when I was younger doesn’t mean shit. Just because a guy appreciates a few feminine things doesn’t mean he wants to work as a prostitute in your damn den!”

“That is true.” She mused, “But that’s what you want. Deep down. It is what will make you happiest dear, believe me. You may find this difficult to believe but I only want to make people happy, that includes you.”

Max felt his blood boil.

“You don’t know that! Just send in my next client so I can get this over with, it’s got to be close to morning by now. Let’s just finish this.”

He just needed her to leave, so he could stop thinking about what she said. It wasn’t true, it wasn’t. He didn’t want to spend his days being beautiful and having wonderful sex with men all night…every night…

A small amount of wetness began to leak down his leg; thankfully the towel caught it before Madam Nightshade’s eyes did. She was lying, this life wouldn’t make him happy, more than that his life before wasn’t even bad! Okay, there wasn’t exactly much excitement, he didn’t have much in the way of friends and his job was sort of boring but he had…well he had things that made him happy. He just couldn’t think of them right this moment was all with Madam Nightshade staring at him with that subtle smile on her face.

“The magic of my boudoir reveals all. My magic does not manipulate or control, only reveal. You will understand this in time.” Madam Nightshade continued, “Your next client you will take in the room at the end of the hall.”

“Why there?”

“Because it is my room.”

“You’re going to watch?” Max balked; he wasn’t sure he could handle that; Madam Nightshade simply chuckled.

“No, dear Maxie.”

She hooked a finger under his chin, forcing him to look into those beautiful, dark eyes.

“You’re next and final client, shall be me.”