[TG] From Student to Master - Part 5 (Patreon)

Personal Patron Tier Reward Story for Deadtom

Stuart begins to embrace his inner sex kitten while Lisa's control over the situation begins to slip. 

~

Stuart had never felt so pampered in all his life. The white, silken panties and bra felt heavenly against his smooth skin and the dress Brad had picked out was truly stunning; red satin that hugged his curves in all the best ways while still have a plunging neckline and slit down one leg to show off his body in the most wonderful ways. He couldn’t help but smirk slightly as every man in the restaurant turned to look at him as they walked by; he outshone every other woman in here and Brad was clearly the object of every man’s envy for having Stuart on his arm. He had to admit, he’d underestimated Lisa’s boyfriend. While domineering in the bedroom he seemed like a genuinely nice guy who wanted to ensure he treated his woman right; that meant pampering her after a good fucking.

‘Wellingtons’ was one of the most expensive Michelin star restaurants in the city, Stuart had never entertained the idea of ever eating there when an entrée cost half his weekly pay. Yet here he was, about to have three whole courses, plus cocktails, all on Brad’s card at his insistence.

“You’re sure you will pay the entire bill?” he checked as Bra pulled out a chair for him.

“Of course, since when do you ever offer to pay?” He chuckled good naturedly, Stuart was suddenly filled with a sense of indignant rage at the injustice of such a man being wasted on a brat like Lisa.

Sitting down he couldn’t help but wince slightly, his pussy still ached from all the punishment it had taken today; Stuart would be lying if he said the slightly pain wasn’t gratifying though, already he was wondering how to go about initiating something once they got back to the apartment. Pride be damned, he was having the best sex of his life in this body, why not enjoy it? Especially when it came with the added benefit of being treated like an absolute princess.

The food was exquisite, from caviar and beef tartare starters to the incredible lobster main Stuart was at a loss for words. He couldn’t help but moan as he popped another rich piece of seafood in his mouth.

“Careful babe, making noises like that, people might get the wrong idea.” Brad teased and Stuart blushed, he hadn’t even realised he sounded so…pornographic.

A moment later, Stuart felt a subtle buzz come from the handbag sitting by his feet. Curiously, he bent down and opened it to find a phone, of course Lisa had more than one. She probably had a phone to match every one of her handbags honestly. He was about to ignore it in favour of their meal when he recognised the number, it was his own. With some trepidation he picked up the phone and unlocked it, clicking on the message and immediately being confronted with a picture of his own dick; coated in lipstick in some dark alley.

‘Hope you’re having as much fun as me ; ) tit for tat, better send me a pic as well.’

The ‘or else’ was very much implied.

“Everything okay?”

Stuart felt a small smile tug at his mouth as he looked at his old cock, he couldn’t help but be aroused at the sight of it, even covered in some streetwalker’s lipstick.

“Yeah, all good. I just have to go to the bathroom. Don’t finish this off without me!”

He tried to hide the spring in his step; he’d never taken nudes before but if Lisa wanted proof of him having a good time, he was going to damn well give it to her. The slinky dress fell off his shoulders easily; normally he would have been hesitant to drop such a beautiful and no doubt expensive item on a bathroom floor but in a place, this fancy he figured it was safe. He lifted the camera skyward, ensuring both his breasts and ass were on full display in their new lingerie before taking the snap. Then another. And another. Each time ensuring his pose was alluring and his smile wide, he even pulled down the panties to show off his pink pussy, still slightly raw from the pounding it took; there was even a small amount of cum still dripping out that hadn’t been washed out in the shower. It wasn’t until he’d taken his seventh photo that he realised he was enjoying this, making Lisa jealous. She had done this swap in order to humiliate him well, what better way to insult her than embracing it?

With absolute glee he typed back.

‘Having the time of my life, better go now Brad is waiting, enjoy your alley.’

Funnily enough, she didn’t respond.

~

The bass rumbled beneath Stuart’s feet as he danced, he could feel the loud music pumping through his entire body; it was glorious. He’d always been so focused on his career that he’d never really gone clubbing, even when he was younger, now though he finally got the appeal. It was a sort of whiplash after the fancy wine and food of Wellingtons but the vodka shots and sweaty crowd made him feel wild and alive so he couldn’t bring himself to care. What’s more, Brad’s hands on hips, moving together and messily kissing between gyrations was utter bliss. Maybe it was the alcohol or maybe he was finally loosening up but Stuart found he didn’t mind the stares and touches now, on the contrary he wanted more of them.

So, when Brad finally pulled him into a taxi after a wild few hours on the floor he did not hesitate to crawl into his lap and start kissing his neck. Only stopping when the driver awkwardly cleared his throat and told him to put on a seatbelt.

“My little sex kitten is really on the prowl tonight.” Brad chuckled, laying a hand high on Stuart’s thigh teasingly, already he could feel wetness soaking into those pretty white panties. Not so innocent looking anymore.

Stuart wasn’t even sure how they got back to the penthouse, it was all a blur of kissing and roaming hands until Brad gently pushed him back into those silky sheets. Feeling bold, Stuart crawled back to him, unzipping the man’s fly and taking that heavy length in his hand. It was time to truly embrace what this body was capable of. With a streak of dominance that clearly surprised Brad, Stuart pulled him onto the bed, crawling over his legs until his mouth was hovering above the hard cock.

“Fuck yes babe, it’s been forever since you sucked me off.”

Poor Brad, he really did deserve better than Lisa and Stuart was going to prove it. He’d never sucked dick before, but having been on the receiving end he knew what felt good, emboldened by the alcohol in his blood he slipped the tip of his tongue between his lips, licking a stripe across the head. A drop of precum appeared from the slit and he immediately lapped it up, treasuring that unique, slightly salty taste. Brad moaned as he continued down the shaft, licking and mouthing at the flesh gently until the entire shaft was claimed, wet and ready for his mouth to sink down upon.

He was forced to place a hand at Brad’s solid hips, holding him in position as they bucked with each gentle lick.

“Careful now, wouldn’t want you to accidentally get any teeth.” He whispered before closing his lips around the tip and swirling his tongue.

If Brad had any sort of come back it was lost in a primal groan as his hands buried themselves in Stuart’s long hair. The grip was hard, grounding and Stuart found he loved it. Teasingly he began to bob, only taking in the tip but gradually going further with each suck until after almost a minute, he could feel the tip of Brad’s cock brush against the back of his throat. He expected to gag but found his body didn’t seem to care, what luck. He continued, hollowing his cheeks and bobbing up and down as saliva dribbled down the shaft. Brad’s hands were shaking as we his legs, his hips rising to meet Stuart’s mouth quicker and quicker.

“Fuck, babe, I’m cumming-!”

He let go, clearly expecting Stuart to stop so Brad would cum on his own stomach. Tempting as the sight would be, Stuart did not falter he kept sucking, harder and harder with a hand gently squeezing Brad’s balls until his back arched and Stuart found his mouth flooded with more of that delicious, salty liquid. He swallowed it down without hesitation before licking the shaft clean, a tiny drip of white fluid dribbling down his chin.

He wiped it away proudly, looking down at Brad’s heaving body, still shivering in the post orgasm bliss he knew all to well. The man’s eyes were glued to Stuart kneeling between his legs, a cocky smile appeared and suddenly Stuart found himself flung forward as Brad’s legs closed around him, pulling them flush together. Both gave breathy laughs before their lips found one another again. God, it felt so nice to be kissed this way, firm yet yielding at the same time.

Brad’s hands began to roam as they made out, sliding up his thigh and under his dress to cup his round ass. Squeezing it tight and slipping a finger into the leg hole of the panties to gently start pulling them down.

“You are wearing entirely too much clothing.” He murmured, pushing Stuart up so that he could unclasp the bra as well, “I think I need to do something about that.”

Stuart could only gasp in pleasure as the dress was pushed off his shoulder to bunch at his hips, leaving his lose bra the only thing between Brad’s hands and his breasts. He couldn’t help but keen as the man’s fingers traced over the petal patterned lace before finally, fully unhooking the bra and chucking it aside. His hands felt so very warm cupping his heavy tits, Stuart moaned, thrills of bliss passing through him as Brad gently played with his nipples. Already his hips were beginning to stutter, dampness soaking into the gifted panties at an alarming rate.

“Shall I fuck you into the mattress?” Brad grinned, gripping both his tits hard and making Stuart see stars.

“N-No I…I want-“

What did he want? A cock, that much was obvious but more than that, he wanted to take charge again.

“I want to ride you.” He keened, pushing Brad down into the mattress himself and pressing his soaking panties against his already hardening cock.

Brad only smiled, pushing himself back up on his elbows enough to remove his shirt while Stuart dragged down his panties. Now the only thing left between them were those white panties which Stuart once again pressed to the base of the man’s shaft. He swore he could feel every individual stich pressing against his sensitive folds along with the heat from Brad’s skin. It sent tingles across his over sensitive skin and a whimper, both desperate and horny, escaped his mouth.

Brad’s gentleness evaporated as he finished what he started, yanking the panties down and exposing Stuart’s pussy to the cool air; he kicked them off without a second thought and positioned himself above the length. He swallowed somewhat nervously but did not allow himself to hesitate further and gradually sunk down. The burn of his inner walls stretching was now familiar but no less wonderful; he could feel the tip brushing his G-spot as he came to rest sitting flush on Brad’s hips. For a moment he simply stayed there, eyes closed, enjoying the unique gratification that came from being so deeply penetrated but then Brad’s hips rolled against his, eliciting such delicious feeling that Stuart’s could help but moan and roll his hips in turn. Before he could think he was bouncing on the cock, drawing himself up high enough that only the tip remained before sinking down with rapid speed.

It felt different, being the one on top, deciding the pace and position. Yet the pleasure was just as wonderful, and building ever faster as he leaned back to ensure his G-spot was being rubbed at all times. Stuart felt that familiar haze of lust descending over his mind, all other thoughts blocked out, leaving him only with the primal need for pleasure. His moans began short and high pitched as his insides began to tighten, he could feel the orgasm coming and he raced toward it. Wanting more, needing more.

“Yes, yes…Yes!!”

It was the only coherent word he could manage, Brad was holding his hips and thrusting up into him with such force Stuart was seeing stars and then, his vision went white. Pure ecstasy washed over him and he felt his pussy squeeze around the clock, milking it for every last drop of gratification it could. Every muscle in his body tightened before relaxing involuntarily, he could just barely keep himself upright long enough for Brad to thrust in one more time, filling him with even more seed.

They shuddered together, collapsing into a sweaty heap atop the sheets. Sated and exhausted Stuart curled up, humming contently as Brad wrapped a muscled arm around his torso. His pussy pulsed with aftershocks, each one causing more cum to dribble out of his hole. Comfortable, safe and in a fog of post-coital pleasure Stuart fell into a deep, restful sleep.

~

Lisa grimaced, looking at the photos Stuart had sent. She had been gleeful when he’d responded so promptly, eagerly opening each file to bask in his humiliated expressions and nervous poses; but she’d gotten none of that. Every photo showed a sexy, confident woman showing off her body with abandon. Her submissive little Stuart was nowhere to be seen and she detested it. She’d expected shame after being pounded so hard by Brad but if anything, Stuart looked more confident than she’d ever seen him, even as a man.

She grasped her cock in anger, pumping it in time with Stuart’s bouncing as he mounted her boyfriend; she’d show him tomorrow, oh yes, she’d wipe that confident smile of his fucking face and show him where he belonged, on his knees before her. She’d have that body all to herself soon enough, she’d make Stuart her personal sex doll. The idea had her finishing, seed spilling messily over her hand but there was none of the relaxing come down she wanted. The gesture felt hollow somehow and left her feeling unsatisfied and pissed off.

After several frustrated hours waiting, her security system finally told her Stuart and Brad were home. She eagerly logged on only to find the video feed wasn’t much better; her arousal was awakened again watching Stuart giving Brad a blowjob, it soured when she zoomed in on his face, clearly loving it. He was supposed to be humiliated! Taken down a peg as punishment for turning her down originally! This was supposed to be sexual torture for him not…fun! With a frustrated growl she slammed down the laptop, settling into Stuart’s tiny bed and settled in for a rough night, tossing and turning on the lumpy mattress. Comforted only by the idea that tomorrow morning, things would get back on track.

~

Stuart was tempted to skip classes today; Brad made getting out of bed incredibly difficult, especially when he woke up hard. How was Stuart supposed to resist taking the man for another spin; it had been years since he started his day with sex and he’d almost forgotten how it managed to brighten the entire day ahead. Two glorious orgasms later he was finally dragging himself out of the sheets and denying Brad’s offer to help clean him up.

“I want to smell like you today.” Stuart whispered, putting on a new pair of panties and feeling the cum begin to soak into them. When Lisa got her hands on him and saw that it would set her blood ablaze. He couldn’t wait.

He took his time picking an outfit for the day, it almost made him late. He’d tried many yesterday and decided on the cute pink mini skirt and matching black tank top, it barely met the decency standard for the university, especially when he paired them with a set of strappy heels. In this, he was sure to have every eye on him, something that now excited him greatly. Maybe he could even test and see which professors he could catch checking him out. Giving Brad a quick peck on the cheek he departed, whisked away to the university campus in luxury by a private car.

Lisa’s next exam was at eleven thirty, plenty of time for him to stop by his old office and she no doubt expected him to. He wasn’t going to give her the pleasure of summoning him, instead he walked confidently down the hall, enjoying the appreciative glances several guys made as his short skirt swayed with his hips. He’d be lying if he said the nervousness at facing Lisa again wasn’t still present in come capacity, he could feel his palms sweating as he approached the office door. Wiping them on his skirt quickly he did his best to bury the trepidation; reminding himself to be empowered by the pleasure of his new body, not beholden to it.

He rapped his knuckles against the wood twice before letting himself in. Biting down on his cheek as Lisa looked up from his computer with a sly, confident smile.

“Well, hello.” She purred, “Aren’t we the wild one, I did so love your pictures and performance last night.”

“Performance?”

“Oh, did I forget to tell you, I have security camera set up in my apartment?” She grinned, swivelling the computer screen to reveal a recording of him on his hands a knees by the mirror, Brad thrusting into him.

Stuart felt his cheeks burn, the woman in the recording was so wanton, her shameless moans sent arousal and humiliation burning inside him. At least for a moment; that sex had been incredible, so what if he’d enjoyed himself? At least he’d been having a good time, not perving with one hand around his dick like she obviously had been.

“Glad you had something to keep you entertained.” He crossed his arms, refusing to be perturbed and enjoying the way Lisa’s eyebrow twitched in irritation.

“You think you’re back in control, huh?” She growled, pushing back the chair and prowling around the desk. Her shirt was unbuttoned with the sleeves rolled up to reveal her strength and toned physic.

Despite everything, Stuart felt his own wetness begin to mix with the cum in his panties.

“I think you need to be taken down a peg, arrogance isn’t a good look for you, sweetheart.”

Lisa’s hands reached out and around his thin figure, finding his plump ass and pulling them together so that he could feel the bulge in her pants.

“It’s time I reminded you what you really are, a desperate little sub who can only be satisfied by me.”

An instant later her teeth were at his throat, sucking and biting down on the soft flesh hard enough to leave marks.

“Let’s see what brad has to say when you come home covered in my marks.”

Stuart tried to think of a retort but the pleasure and pain from those bites were beginning to fog his brain. There was something primal and oh so very wonderful about being claimed so physically by another. Lisa’s tongue swipes across the indents left by her teeth, soothing the red skin and sending tingles down Stuart’s spine where they pooled in his lower stomach. Horny and wanting nothing more than to be touched he let himself be led to the office chair where Lisa pushed him down and lifted his skirt.

“You really are asking for it,” She said huskily, “Dressed like this.”

He keened, obediently raising his hips so she could remove his underwear, smirking at her irritated expression when she saw the mess already in them. Residual seed flowed out with his juices and to his surprise, Lisa didn’t hesitate to lap at it with her tongue. The touch against his folds was deliberately light and teasing, causing his whole body to quiver as Lisa hummed contently.

“Miss his cum, do you?” Stuart teased breathlessly, earning him a hard glare.

Without warning Lisa surged forward, sucking hard at his clit and making him cry out in shock and ecstasy.

“You. Do not. Tease. Me.” She seethed, punctuating the words with licks that were so hard they almost hurt. His whole body shuddered with bliss at the torture.

She began to feast upon him, whole mouth encompassing his pussy as her tongue dove into his waiting hole. He moaned and shivered, the pressure inside him growing already at the stimulation. He didn’t throw his head back this time though, he forced it forwards, looking down at his old body eating him out. Lisa looked…pathetic, there on her knees going down on him, he couldn’t help but give a satisfied chuckle and she shot him a look.

“You…keep talking about putting me in my place.” He panted, “But you’re the one on your knees, pleasuring me.”

She pulled away, thunderous expression on her face and Stuart felt his confidence grow.

“Get up.” She growled and he did so, smile never leaving his face even as she roughly bent him over the desk.

His skirt was pushed up past his waist, leaving his ass and pussy exposed to the air. Stuart grinned, gripping the desk with both hands ready as she shoved her way inside. It felt good, excellent in fact but he couldn’t help but lament his old cock now; it was smaller than Brad’s not nearly as powerful. She was showing him no mercy, thrusting in hard and fast, the roughness might have been too much for him to handle before but now he knew it was her desperation getting the best of her. He may be the one bent over being fucked, but he was still in control and she hated it.

A sharp slap to his ass cheek made him moan, the extra sensitive skin tingled in the aftermath in the most delicious of ways.

“Beg me for more.” She ordered; Stuart grinned and stayed silent. “Go on! Beg!”

He just huffed in amusement, enjoying the burning gratification between his legs. He could feel himself getting closer; Lisa may not have been as big as Brad but even she couldn’t help but hit his G-spot every few thrusts. He looked back at her over his shoulder and moaned, rolling his eyes in a performative matter that was sure to irritate.

“I. Said. Beg.” Each word signalled a hard thrust, each one making him see stars.

Again, he said nothing. He was so close and he knew she was too, no matter what he did, she wouldn’t be able to stop now. She was helpless against her own burning desire. The intoxicating power and pleasure from being fucked all melted together in his core, muscles clenching for a moment before releasing a wave of bliss. He writhed and moaned, making sure she knew he was cumming and loving every second of it. He squeezed around his old cock, tight as he could and grinning as he heard a surprised and pleasured gasp escape Lisa’s mouth. A moment later, warm seed flooded him; she’d not meant to cum yet but he’d teased it out of her anyway despite his position below.

She withdrew quickly, no doubt embarrassed and trying to hide it. Stuart simply picked up his panties and stepped back into them nonchalantly, savouring every second of Lisa’s humiliation and fury.

“That was great, thank you!” He said almost musically, “I’d love to stay for round two but I have a very important exam to take.”

Lisa said nothing, but her teeth were grinding so hard Stuart swore he could hear them even as he headed for the door.

“Oh, by the way, we really should be more careful in the future.” He added with a smirk, “I don’t know how to use your birth control, you never did explain how.”

Stuart gave one final bark of laughter as the blood drained from Lisa’s face before exiting the room and strutting down the hall to the next exam.

“Well, sweetheart.” He whispered under his breath, “Let’s see how you like it now that the tables are turned…”