[TF/TG] Max's Long Night - Part 2 (Commission) (Patreon)

An extra chapter commissioned DeSaJo as an addition to their Personal Touch Patron Reward. 

Max takes on his first client and finds himself learning to enjoy this new body, perhaps too much. 

~

Madam Nightshade led him down the dark corridor toward the back of the building. As they passed each room Max took in the name engraved on each door’s golden plaque, Trixie, Delilah, Amy; how many of these women had been men once like he and Tabitha? Could it really be all of them? Had they been given the same deal as him? If they had, his chances of changing back with his mind in tact seemed slim. He strained his ears and swore he could hear the sound of muffled voices and moans behind the thick wood and his cheeks flushed at the realisation that he would be joining them soon.

“Here we are, the temporary room.” Madam Nightshade smiled, pushing open a door without a label and ushering him inside.

The room was lovely, missing a few of the smaller details and personal affectations of Tabitha’s but still complete with a large bed complete with silk sheets.

“How long until you turn me back?” Max asked, “You said I had to last the night.”

“Six AM.” She responded, “Don’t you worry, I am sure you will have plenty of clients before then. I’ll give you half an hour to search the cupboard for something suitable to wear but then I will start calling on you.”

Half an hour to come to terms with his new body, dress it and start…servicing men. Max’s gut swirled with a maelstrom of conflicting emotions; fear and trepidation naturally but also, beneath it all was a small ember of desire. From here he could already see the open cupboard, packed full of colourful and alluring outfits. A sudden memory; of sitting beside his sister Christmas day as she unwrapped a chiffon gown. Max remembered aching with a jealousy that he couldn’t understand, gripping his own pair of sensible jeans and pretending not to care. He quashed the memory; this was no time to think back on that silly teenage phase. Madam Nightshade ran her hands over his new slopped shoulders approvingly before taking his chin in her palm.

“Remember darling, only a whore needs to be naked to draw a client in. A lady such as yourself can make a man cum in his trousers just by picking the right outfit. Take your time.”

Max felt not unlike a kitten being taught to hunt by a mother cat. There was genuine warmth in Madam Nightshade’s smile as she passed on the sage advice; despite everything he felt heat bloom in his chest, dusting his breasts a gentle pink.

“I’ll leave you to it.” She winked, sauntering out the door and locking it behind her.

Max swallowed. All he had to do was get through the next few hours without ‘giving in to the pleasure of his female body’, whatever that meant. That shouldn’t be too hard, after all he barely knew this form at all and he’d be focusing on pleasuring his clients, not himself. A little voice in his mind told him he was accepting this too easily, what sort of man just went along with a crazy plan like this unless of course, deep down he was secretly okay with it. He silenced that voice before it could take hold.

Max wasn’t into guys, of course he wasn’t, he was straight as an arrow and yet, that little ember of desire inside him burned in this new body. He couldn’t help but wonder what it was truly capable of. He’d always been curious about how it would feel to be on the other side of the sexual wall but, that was totally normal wasn’t it? It’s not like he wanted this to happen but now that it had…there was no harm in trying to make the best of a bad and very temporary situation…right?

Pushing all those confusing emotions away Max headed for the cupboard, swinging it open fully to peruse his options. There were a dozen different colours and designs, everything from leather straps to soft satin negligees; Max was beginning to see what Tabitha meant about having experience being all sorts of girls. What sort of woman was he? Tonight anyway, he quickly added mentally. Max looked down at his body, it was certainly gorgeous; not stick thin like all those models on the front of the glamour magazines he saw at the checkout and definitely wasn’t tempted to buy, bur rather curvaceous. He still had some meat on his bones, but in all the right places, that is to say, hips, tits and ass. He tried to ignore the sense of pride that filled him, it was just because his old body wasn’t that impressive, it was the novelty of the change making him feel that way. Yes, that was all.

Max shook his head clear of such thoughts, he had to focus, pick an outfit the Madam would approve of. He had the very distinct feeling that were he not to at least put in some effort, the terms of their deal may become somewhat tighter. So, he had to decide, sweet and innocent, sexy and sultry, mysterious glamour? What was his angle? He ran his fingers across the fabrics, taking in their different textures until they stopped on a black negligee; it was elegant in its simplicity, smooth satin material with a heart shaped neckline and very short skirt that would rest just below his waist with a fine black lace trim. It would hug these new curves in all the right places and while it was skimpy, it didn’t feel, for lack of a better term, whorish. It was beautiful and Max knew instantly that this would be his for the night.

He enjoyed the cool sensation of satin gliding across his skin as he pulled the outfit on, amazed to find it fit him perfectly, lace brushing his thighs and generous amount of cleavage on display. He padded across the room on his tip toes, enjoying the freedom that came with such an open outfit, and took in his reflection. His beautiful red hair flowed in gentle waves down his back, contrasting with the shimmering black satin. Mysterious glamour it was. Max actually felt a small lump form in his throat; he was glamourous; never in his life did he suspect that was a word that would ever apply to him. He swallowed down the lump and the confliction emotions it bought, likely a side effect of whatever magic pill did this to him, nothing more.

There came a tinkling chime from somewhere above him and the door to his room opened. He was being summoned. The walk down the hall felt simultaneously too short and too long. Max’s heart pounded in his ears with ear step, he’d never been so nervous in his life. As he pulled back the curtain and stepped into the foyer, he was met with Madam Nightshade and a handsome young stranger; blonde, around Max’s own age but with a boyish face and a nervous demeanour.

“This is Maxie.” Madam Nightshare introduced and Max bit his lip, eyes lowering instinctually as butterflies raced in his stomach. “She’s quite new, I think you’ll find her a good match.”

“Okay.” The man swallowed, “Hi Maxie, I’m uh Rob.”

Rob shuffled, awkwardly thrusting out a hand to shake and despite everything a small smile formed on Max’s face. This was clearly the man’s first time in a red light district, he was trying not to make a fool of himself. That helped put some of his own insecurities as ease, at least his first client didn’t have specific expectations. The idea of serving him though…that still made his stomach flip.

“Take things slow.” Madam Nightshade insisted, “Enjoy yourselves.”

Max took a deep breath and clutched Rob’s hand in his own. He may be uncomfortable but he could at least show this guy a good time, he wasn’t doing anything wrong by being here anyway. He’d show Madam Nightshade who the bigger person was. They walked together down the hall in awkward silence, Max wanted to put his client at ease but had no idea how when he was just as anxious. What was the old adage, fake it till you make it? How did you fake something you had no idea how to be?

By the time they had made it back to the room Max felt like a total wreck on the inside; torn between wanting to test this body and being terrified that he may in fact enjoy himself. Rob looked flustered as well but Max couldn’t help but notice the way his eyes roamed across his curves, settling on his cleavage more than one before hastily looking away. To see somebody, even a man, admiring his body in such a way felt nice he had to admit. It wasn’t often he found himself the object of somebody’s desire.

“How about a blow job.” Max suggested, there was no risk of him ‘giving in to pleasure’ if he wasn’t receiving any after all.

“That’s be so nice.” Rob sighed, “But um, just warning you it’s sort of been a while so I don’t think…”

“You’ll last very long?” Max gave him what he hoped was an understanding look, “Don’t worry honey, I’m not in a position to judge anybody.”

He wasn’t sure where that affectation came from but it seemed to do the trick. Rob seemed to relax as he unbuckled his pants and Max waved him over to the bed, trying to ignore the way his skin was tingling in anticipation; this was just a job he had to do, nothing to be excited about. And yet, he couldn’t deny that he was excited. The idea of being forced to suck on another man’s cock should have been disgusting to him, a massive turn off, something he would have to metaphorically grit his teeth and bear just for the sake of being turned back at the end of the night. Yet here he was suggesting it, with butterflies forming as he watched Rob slowly pull down his boxers to reveal his already hard length. It stood upright, stiff and ready as he laid back, fingers kneading the mattress nervously.

“You can uh, start whenever.” He mumbled, “Sorry I know it’s not much, I’ve never done-“

“Don’t apologise.” Max interrupted before adding, “I was just admiring it, you have nothing to be ashamed of.”

It was true, Rob was actually fairly impressive by male standards, at least size wise. Max found his mouth watering as the butterflies began to race faster, no matter how much he tried to get a hold of himself. Slowly, he crawled onto the bed, feeling the weight of his breasts as they hung low, free of any sort of support. Out of some instinct he never knew he possessed he rested those heavy tits above Rob’s crotch, letting his cock rest in the cleft between them, squeezed slightly as they swayed and pushed together. The man took a sharp breath and Max hung his head forward in time to see a spot of precum appear at the tip of the erection; knowing it was his body that caused such a reaction made even more of those conflicting feelings to bubble up within Max’s chest.

He couldn’t resist slipping the straps off his negligee, letting bunch around his waist to expose his breasts fully. He reached down and pressed those tits together, squeezing the cock and he began to slowly thrust his chest back and forth. Rob gripped the bedsheets as he did so, breathy moans already escaping him as Max’s tits pleasured him. Max couldn’t help a contend sigh escaping as he continued, the sensitive skin of his breasts squeezing around that hard cock felt better than any massage ever could. He let his eyes flutter closed, fully focusing on the wonderful sensation radiating out from his chest only to catch his breath a moment later. What was he doing? The whole reason he suggested a blow job was so he wouldn’t be tempted by his own pleasure!

He let go of the soft skin of his breasts and quickly shuffled down the bed till his face was even with Rob’s crotch. Trying not to focus on the lingering pleasure blooming across his chest. He could smell that heady, masculine scent wafting from the dark hair and skin there; it should have disgusted him, instead he felt a hunger building within. Before he could hesitate longer, he squeezed his eyes and moved forward to press his full lips to the tip. Even through pursed lips he could taste the saltiness of the precum and found it was not completely unpleasant. Curiosity built and slowly he opened his mouth, letting the tip of his tongue dart out to taste. Rob moaned as the tip ran over his slit, more precum immediately replacing that which Max had licked away.

With trepidation and some other feeling he couldn’t quite identify, Max slowly lowered himself over the head, taking the tip in his mouth. He tried to be put off, to not enjoy the sensation of the shaft slowly felling his cheeks as he hollowed them but he just couldn’t. He could feel Rob quivering from his touch and taste the slight salt of his skin; it was intoxicating. He swallowed him down until the shaft was fully engulfed and the tip rested against the back of his throat, he waited to gag but was surprised to find the sensation was not unpleasant. Tightening his hold, he began to suck and swallow, hyper aware of every twitch and moan his client made, ensuring to copy what ever elicited a good reaction. A rough hand found his head, fingers curling tightly into his long red hair and guiding him upwards. Obediently, Max followed Rob’s lead and began to bob up and down on his cock, keeping his cheeks hollow the way he knew felt the best.

Max thought back to the last blow job he’d received, embarrassed at just how far back he had to recall. Now wasn’t the time for self-pity though, instead he focused on what he remembered and copied it, reaching a gentle hand between them and massaging Rob’s balls. Squeezing in time with his sucks and causing Rob to arch of the bed. The man was moaning his name, well, the name he knew as his and the sound went straight to Max’s pussy. The fact that he was capable of eliciting such sounds from somebody was intoxicating, he wanted more. He started to speed up, savouring the way Rob writhed under him as he got closer, his grip on Max’s hair tightened almost painfully.

“Oh Gods, Maxie I-I’m going t-to-!”

Max kept sucking, he should have moved back and let Rob cum onto his stomach but he just couldn’t resist the temptation, he’d come this far anyway. Hot seed burst into his mouth and Max found the taste was actually quite delicious, sweet and salty at the same time. Before he could even think things through, he’d swallowed it down before gently sliding off Rob’s cock and sitting back on the bed.

“I’m sorry!” Rob blushed, “I couldn’t help myself, I should have asked before I, well…”

“Don’t worry about it.” Max smiled, “That was quite fun and, just so you know, you lasted a decent amount of time.”

“Really?”

Rob seemed flattered and Max felt a sense of warmth fill him. It was nice, making somebody happy like this. He helped Rob up and rebuckled his pants for which the man gave him a grateful smile.

“Do I just go back to the front to pay?” He asked, that nervousness seemingly lifted.

Max realised he had no idea so he just nodded, walking him to the door and giving his first client a wave goodbye before closing it gently. The thought swirled in his brain to the point he almost felt dizzy; he’d just serviced his first client as a woman. He almost had to pinch himself to ensure this wasn’t some sort of dream. What was stranger, it hadn’t been the ordeal he’d been expecting, on the contrary giving a blowjob had been quite the pleasurable experience in its own way. Max felt his breath hitch slightly, did that count as ‘giving in’? It had felt nice, having that cock between his tits and under his tongue but surely that wasn’t what Madam Nightshade had been talking, right?

A cold sweat broke out across the back of his neck as he carefully reclothed himself in that satin negligee. He would need to be more careful with his next client. He began to pace, shame rising up and painting his cheeks red, not at what he had done but the fact that he had enjoyed it. Men did not enjoy being forcibly changed into women, they didn’t like the feel of heavy breasts hanging against their chest, or pleasuring other men with their mouths…so why did he? The thought of his inevitable next client should be filling him with humiliation and dread or at the very least some form of righteous anger that Madam Nightshade had even put him in this position to begin with! Yet the only shame he felt was at his own lack of shame! He was so wrapped up in these conflicting thoughts the knock at the door made him jump. Another client, already?

“How are you going, darling?” Madam Nightshade let herself in, a sultry smile on her face.

“You did very well, young Rob was very pleased.”

Max tried to hide how nice that praise made him feel.

“If I didn’t know any better, I’d say you’d done that before.” She cooed. “Or at the very least…thought about it.”

The dusting of pink across Max’s cheeks flushed a deep crimson. It was natural to wonder what it felt like on the other side from time to time, it didn’t mean anything!

“I just want to win your little game, that’s all. If I didn’t give it my all you’d pull some trick and make me stay longer or something.”

“Would that be so bad?”

“Yes, obviously.” Max bit the inside of his cheek.

Madam Nightshade walked toward him slowly, taking his chin in her soft palms and forcing his gaze up to meet hers. There was so glimmer of magic in her eyes, only a strange warmth he couldn’t quite describe.

“Many men visit my house.” She said, “I only pick special ones for spells such as yours. Think about why I chose you, Maxie.”

“How the hell am I supposed to know?”

“I’m sure you’ll figure it out.” She sighed, sounding almost disappointed, “Get yourself together, there are still several hours left before the end of the night and I mean to put you to work for all of them.”