Alex’s Surrender
Chapter 3: Session Three
The next day... Alex shifted uncomfortably in his office chair, his caged cock stirring, trying desperately to become erect as his mind replayed scenes from yesterday’s session. The way Mistress Isabella’s cock had filled him, the overwhelming pleasure he felt with her, the way she smoked her cigars. Every few minutes, he’d glance at the clock in the corner of his computer screen. 2:17 PM. 3:42 PM. 4:58 PM his mind desperately wanting to be back there.
At 5:00 PM, he left his desk and slipped into the single-stall bathroom, he opened the small brown bottle of poppers inhaling three times in each nostril. A rush of warmth flooded his head, a dizzying, euphoric wave that made his heart pound. Then he lubed the purple butt plug, coated it with lube, and slowly worked it into his ass. The fullness made him gasp with pleasure, it felt good.
At 5:30 PM, left work and made his way across town for his 6pm appointment with Mistress Isabella, stopping on the way to get some flowers and a bottle of champagne. At precisely 6:00 PM, he knocked on her door, The door opened to reveal Mistress Isabella, as beautiful as ever wearing a form-fitting leather corset that accentuated her waist, paired with thigh-high leather boots.
“Come” she said, guestering him inside. “And are these for me ?” she asked looking at the champagne and flowers.
“Yes they are” he replied
“Yes they are mistress, please don’t forget your place” she corrected reaching for the items.
Inside, she grabbed his crotch feeling for the cage, “And you’ve followed my instructions too. Good boy.”
She then gestured him into her chamber.
Once in the chamber Alex quickly, removed his clothes until he stood naked before her as was the protocol, the pink cage on full display. Mistress Isabella circled him slowly, her heels clicking on the floor and she inspected him.
“Bend over,” she ordered.
Alex complied, placing his hands on his knees. He felt her fingers probe his entrance, confirming the plug was there as instructed.
“Good,” she said with satisfaction. “Now, let’s get that cage off you.”
She unlocked the padlock and removed the pink cage, his cock springing free, already semi-hard from the constant stimulation of the plug.
“I want you free today,” she explained, a mysterious smile playing on her lips. “I want to see how your body responds without constraints.”
She guided him to the leather armchair and retrieved the silver pendulum. “Look at the pendulum,” she said, her voice already smoothing. The induction was quick and easy for Isabella and Alex’s mind sank rapidly into a trance. When he emerged, he felt refreshed and energised but like yesterday couldn’t recall what she had told him while he was under but looking at the clock it was now 6.30pm, so he had been under a while
“Come with me,” she said, leading him to a large screen that had been set up in the corner of the room. “I have something different for you today, I want you to watch”
She clicked a remote, and images began to flash across the screen. They were all pictures of cocks—in various sizes, shapes, and states of arousal. Some were close-ups, others showed the full body of muscular men, others larger men. Alex felt his own cock respond, growing harder with each ing image until it was harder than he had ever seen it.
“Interesting,” Mistress Isabella observed, her voice a low purr. “Your body seems to like what it sees.”
Alex flushed with embarrassment, he didn’t know what to say, He wasn’t gay, but these cocks were turning him on, and slowly a craving to touch a real cock started to fill him mind.
“What are you thinking?” she asked, her eyes fixed on his face.
Alex, his cheeks red with embarrassment. “I... I was wondering what a real cock would feel like.”
“Mistress says, there is nothing wrong with that” she said matter of factly, her words instantly soothed his mental struggle about cocks, She then gestured to the screen where a particularly impressive specimen was displayed. “What would you like to do with that cock?”
“I... I’d love to taste it” he itted, his voice barely a whisper. “And I want to feel it in me”
Mistress Isabella smiled, a predatory glint in her eyes. “I thought you might say that.”
She clicked the remote again, and the screen continued its slide show. “Stay here,” she commanded, leaving the room.
Alex stood there, watching the pictures of cocks on the TV screen, his cock throbbing with need.
A moment later, the door opened, and Mistress Isabella returned, followed by a well built bald man. He was tall, easily over six feet, with broad shoulders and a well-defined chest. His arms were thick with muscle, not muscle that comes from a gym but muscle that is built from hard physical labour, and his arms was covered in intricate tattoos. He wore nothing but a pair of tight black briefs that did little to hide his impressive endowment.
“Alex,” Mistress Isabella said, her voice dripping with authority, “this is Marcus. He’s going to help us today.”
Marcus stepped forward, his eyes appraising Alex’s naked form. A slow smile spread across his face as he took in the Alex’s body and his raging hard-on.
“So this is the little faggot you told me about,” Marcus said, his voice deep and resonant.
Alex flinched at the word Faggot, but to his shame, his cock remained painfully hard and erect.
“Mistress says,” Mistress Isabella began, her voice dropping into that hypnotic tone she often used, “tell Marcus that you want to feel his cock”
The urge was immediate, undeniable. “Please,” Alex heard himself say, the words feeling both foreign and completely right, “please I want to feel your cock”
Marcus chuckled, but mistress Isabella quickly interrupted, “You’ll address him as Sir when speaking to him. Got that?” her words firm and commanding.
Alex nodded, and corrected himself “Please Sir, I want to feel your cock”
Marcus smiled, “Well, since you asked so nicely...”
Mistress Isabella gestured to the rug in the centre of the room. “On your hands and knees, Alex. Like yesterday.”
Alex scrambled to obey, his knees and palms pressing against the soft rug. He was more aroused than he had ever been in his life. Mistress Isabella knelt behind him, “Let’s get this plug out of you,” she said, her fingers working the purple device free. With a pop it was out and the sudden emptiness felt wrong, all Alex wanted was for it to be filled again.
“Sniff your poppers, like I taught you” Mistress Isabella ordered, her words again firm and devoid of emotion. This was a command and Alex quickly grabbed his bottle of poppers and began sniffing, deep sniffs. As he sniffed the world dissolved into a euphoric haze the chemical rush hitting him like a tidal wave, he closed his eyes as the pleasure swept over him. When opened his eyes, he saw Marcus standing directly in front of him, his muscular thighs like tree trunks. His thick uncut, semi-erect cock hanging in front of his face.
Behind him, Alex could sense Mistress Isabella’s presence, he could smell the rich, earthy aroma of a freshly lit cigar, its smoke beginning to fill the room.
“You know what to do, faggot,” Mistress Isabella’s voice was a low purr, “Mistress says, suck his cock.”
The command was all the encouragement that Alex needed, he leaned forward, his mouth opening instinctively. He took the head of Marcus’s cock into his mouth, the taste overwhelming his senses. His technique was clumsy, all teeth and awkward suction. He tried to mimic what he’d seen in videos, but without success.
“No, no, no,” Mistress Isabella chided from behind him. She took a long drag from her cigar, and Alex could hear the faint crackle of the burning tobacco. “Use your tongue. Lick the head. Worship it.”
He tried to follow her instructions, swirling his tongue around the sensitive tip. Marcus grunted, his hand coming to rest on the back of Alex’s head, not pushing, just a heavy, possessive weight. Emboldened, Alex tried to take more of the shaft into his mouth, but he went too deep, too fast. His gag reflex kicked in violently, and he choked, pulling back with a strangled cough, tears springing to his eyes.
Before he could recover, Mistress Isabella’s hand was on the back of his neck, her grip like iron. She pushed his head forward, forcing his mouth back onto Marcus’s now-hardening cock. “You don’t stop until I say so,” she commanded, her voice dangerously close to his ear. She held him there, the thick flesh filling his mouth, cutting off his air for a terrifying moment. Panic warred with the overwhelming need to obey. “Breathe through your nose. Relax your throat. Take it.”
He struggled, his body tensing, and fighting his own reflexes, but over time he managed to do as she said. He relaxed his throat, and Marcus’s cock slid deeper. The panic subsided, replaced by a strange, sensation of pleassure that he was pleasing Marcus. When Mistress Isabella finally released her grip, Alex didn’t pull away he just continued sucking and worshipping this cock finding a rhythm.
“Good boy,” Mistress Isabella praised, her voice soft. She took another long, slow drag from her cigar. “Now, poppers again. Three deep sniffs in each nostril.”
Alex fumbled for the bottle, his mouth still full of Marcus’s cock. He managed to bring it to his nose and inhale as instructed. The rush was even more intense this time, a dizzying wave of pure, unadulterated lust. His entire world narrowed to the cock in his mouth and the voice behind him.
Just as the peak of the poppers hit him, he felt a blunt, wet pressure against his exposed hole. He didn’t have time to process it before Mistress Isabella slowly thrust forward. She was gentle, slowly working it in deeper and deeper, then when it was half in she gave a deep push burying it deep inside his ass. A groan, almost primal escaped Alex’s lips as she did and his body convulsed, his mouth pulling away as he groaned in pleasure.
SLAP!
Her hand came down hard across his ass cheek, the sound echoing in the room. “Did I tell you to stop sucking his cock, faggot?” she snarled, her voice a low growl. “You keep that mouth busy.”
The sharp sting of the slap, combined with the overwhelming fullness in his ass, sent a jolt excitement through him. He immediately plunged his mouth back onto Marcus’s cock, taking it with a desperate hunger.
Mistress Isabella began to fuck him now, her hips snapping forward with a steady, punishing rhythm. Each deep thrust forced his mouth further down onto Marcus’s shaft.
“Look at you,” she taunted, her voice dripping with condescension as she drove into him. “A cock in your mouth and a cock in your ass. Your just a faggot”
She punctuated her words with a particularly hard thrust that made him cry out.
“Tell me what you are,” she demanded. “Say it.”
He tried, but his words were muffled and indistinct around the thick flesh filling his mouth.
“Louder, faggot!” she commanded, slapping his ass again. “Say it while you’re being fucked.”
He pulled back just enough to gasp out the words, his voice ragged with need. “I’m a faggot,” he cried, not in pain but in pleasure, “I’m a faggot, I’ a faggot”
“Again!” she barked, her rhythm never faltering.
“I am a faggot, I love sucking cock!” he repeated, his voice growing stronger, more certain with each declaration. The words, that once so wrong, now felt like the truth. He was lost in overwhelming pleasure and would say anything to make it continue. Alex’s body was acting on pure instinct. As he sucked, and Isabella fucked him his desperate, aching need for his own release became unbearable. His hand, drifted down and wrapped around his straining cock. A jolt of pure pleasure that made his hips buck back against Mistress Isabella’s thrusts. He began to stroke himself, seeking the climax that was building to an unbearable pressure.
SLAP!
The blow was harder than any before, a sharp, stinging crack across his ass that made him yelp. Mistress Isabella’s rhythm stopped instantly. She remained buried deep inside him, her voice cut through the haze of his arousal. “Did I give you permission to touch that worthless little dick?”
Before Alex could even stammer an apology, she gave a sharp, almost imperceptible nod to Marcus. Understanding the signal instantly, Marcus pulled his cock from Alex’s mouth with a wet pop, leaving Alex disappointed. At the same time, Mistress Isabella withdrew her strap-on in one smooth, decisive motion, leaving Alex’s ass feeling suddenly, achingly hollow.
The abrupt cessation of all stimulation was a punishment in itself. He remained on his hands and knees, panting, his body trembling with frustrated need, his cock still painfully hard and bobbing in the air.
“No touching,” Mistress Isabella stated, her voice cold and final. “You don’t get to cum. You don’t get to feel pleasure unless I grant it. And since you can’t follow a simple rule, your punishment is that the pegging and the cock-sucking are over for today.”
Disappointment washed over him, it had felt so good, so wonderful and now it was all gone. He wanted to beg, to plead for another chance, but the tone of her voice told him it would be useless.
She walked over to a small table and returned with the same dripping, ice-cold towel from his previous sessions. Without a word, she wrapped it around his hard cock. The shock of the cold water against his sensitive skin was agonising. He hissed, his entire body tensing as the intense cold did its work, shrinking his erection with brutal efficiency.
Once he was completely flaccid, she tossed the towel aside. She picked up the familiar pink chastity cage. The process was clinical and devoid of the earlier sensuality. She fitted the plastic ring behind his scrotum, slid the cage over his shaft, and clicked the small padlock into place.
CLICK.
The sound echoed in the now-silent chamber, He was caged again, his desperate need for release trapped behind plastic, a reminder of his disobedience. Mistress Isabella stepped back, iring the pink plastic cage. She took a long, satisfying drag from her cigar, letting the smoke curl from her lips before she spoke again, her voice dripping with condescension.
“You’ve been a naughty little faggot, Alex,” she said, her eyes fixed on him. “You were given the privilege of servicing Marcus, and you were selfish. You didn’t have permission to touch your cock and that’s not acceptable.”
She gestured with the cigar toward Marcus, who stood with his arms crossed over his chest, his impressive cock listening with Alex’s saliva. “You interrupted his pleasure. Now, you’re going to apologise.”
Mistress Isabella pointed a finger at the floor in front of Marcus. “Mistress says, Crawl over there. On your hands and knees. Get on your knees in front of him and look him in the eye while you apologise for touching yourself”
Humiliation filled Alex, but the urge to obey was absolute. He scrambled forward on the rug, the plastic cage feeling heavier and more conspicuous with every movement. He stopped directly in front of Marcus and knelt, forcing himself to look up at the imposing, naked man.
“Well?” Mistress Isabella prompted from behind him. “He’s waiting.”
Alex’s throat felt tight, the words catching in his chest. He took a shaky breath. “I... I’m sorry, Sir,” he stammered, his voice barely a whisper.
Marcus just looked at him, his expression unreadable.
“Louder,” Mistress Isabella commanded. “And make it convincing. Tell him what you’re sorry for.”
Alex swallowed hard, his shame mounting. “I’m sorry, Sir,” he repeated, his voice louder this time “I’m sorry for touching myself. It was selfish and I apologise, Sir.”
A slow, cruel smile spread across Marcus’s face. He reached down, not to touch Alex, but to idly stroke his own still erect cock, a deliberate, taunting gesture. “Apology accepted,” he said, his voice deep and resonant with amusement.
“Good,” Mistress Isabella said, taking another long drag from her cigar. She walked over and stood beside Marcus, looking down at Alex. “Your pleasure is irrelevant. Your purpose is to serve. And if you fail to serve properly, your privileges will be taken away.”
She turned and briefly spoke with Marcus, Alex couldn’t hear what was said but whatever it was made Marcus chuckle, Just then the alarm sounded, signalling the end of the session. “See you soon Faggot” Marcus shouted as he left the room.
Mistress Isabella stood over him, a figure of smoke and absolute authority. She took one last, long drag from her cigar, the end glowing as she did. She exhaled, not towards him this time, but a slow, deliberate plume that rose towards the ceiling as if to taunt him more.
“Get up,” she commanded, her voice devoid of its earlier sensual teasing, replaced by a cold, businesslike tone.
Alex scrambled to his feet, his legs stiff and his body still trembling with the aftershocks of pleasure and punishment. He stood awkwardly, unsure of what to do with his hands.
“You have homework tonight,” she stated, walking to the small bag she had given him yesterday. She retrieved it and held it out to him.
“Inside,” she explained, “you will find poppers, lube, and a new toy.” She paused, her eyes locking onto his. “The dildo has a large suction cup on the base. Mistress says, Your assignment is this: on the hour, every hour that you are awake, you will sniff the poppers. Then, you will attach the dildo to a hard surface, like your bathroom floor or a chair, and you will ride it for five minutes.”
A jolt of apprehension mixed with a dark thrill went through him. To do this alone, in his own home, outside of her direct control... it felt wrong but at the same time he felt an overwhelming urge to obey
“Do you understand?” she asked, her voice sharp.
“Yes, Mistress,” he replied, his voice quiet but certain.
Alex then grabbed his clothes and began getting dressed.
“Not so fast.”
He turned to see her holding out a small, black bundle. It was a pair of women’s panties, made of a slick, satiny material with delicate lace trim at the hips. Beside them lay a pair of sheer, black stockings, folded neatly. And a tube of bright, fire-engine red lipstick.
“Mistress says, You will wear these under your clothes until you return tomorrow,” she said, her tone leaving no room for argument.
Alex stared at the items in his hands, a cold knot of dread forming in his stomach. This was different. This wasn’t about pleasure or pain, This was about identity. Dressing as a woman... it felt fundamentally wrong, he hated trans people and dressing In women’s clothes was a line he didn’t want to cross even though part of him desperately wanted to obey.
“No,” he said, the word escaping his lips before he could stop it. It was his first refusal. “I can’t. That’s... that’s not me. It’s wrong.”
Mistress Isabella didn’t get angry. She didn’t raise her voice. She simply took a step closer, her expression unreadable. “Wrong?” she repeated softly, her voice a dangerous purr. “What was wrong was touching yourself without permission. What was wrong was being a selfish little faggot and ruining Marcus’s pleasure. This,” she gestured to the lingerie in his trembling hands, “is a consequence. A reminder of your place.”
She leaned in closer, her face inches from his. “You will do this, Alex. You will put these panties on. You will put these stockings on. And tonight, before you ride your new dildo, you will paint your lips with this lipstick. You will do it because I command it. And if you want your session tomorrow, if you ever want to feel my cock inside you again, you will obey.”
Her words were firm and direct. The threat of being denied what he now craved more than anything was more potent than any slap. The choice was no choice at all. His desire for her, for the pleasure she gave him, crushed his resistance.
His shoulders slumped in defeat. “Yes, Mistress,” he whispered, as he submitted to her again.
A slow, satisfied smile spread across her face. “Good boy.” She turned and walked back to her chair, picking up the humidor. “Now get dressed. And don’t forget your homework.”
With fumbling, clumsy fingers, Alex complied. He pulled the satiny panties up his legs, the foreign feel of the tight material against his skin and the cage making him shudder with humiliation. He struggled with the stockings, rolling them up his smooth legs and fastening them with a fumbling he hoped she didn’t notice. He quickly pulled on his shirt and tros, the professional attire now feeling like a flimsy disguise over the shameful secret beneath.
He left the lipstick in his pocket,
“Same time tomorrow,” she said, not even bothering to look at him as he walked to the door.
“Yes, Mistress,” he replied, his voice hollow.
He stepped out into the cool evening air, the click of the door sealing him back into the normal world. But he wasn’t normal. He was a man in women’s underwear, caged and commanded, with a bag of toys in his hand and a night of humiliating homework ahead of him. And the worst part was the terrifying, undeniable thrill that ran through him at the thought of it all.
That night at home he followed her instructions to the letter. On the hour, every hour, the ritual was the same: carefully applying the bright red lipstick, then the dizzying rush of the poppers, followed by the slick, humiliating, and deeply satisfying act of riding the dildo. The sensations were overwhelming and each time he rode the dildo he loved it more, as the night progressed the challenge became only riding it for 5 minutes, he wanted to ride it longer, the feeling almost bringing him to orgasm, despite been caged. When sarah called, he deliberately ignored her calls, he didn’t want to speak to her tonight, he wasn’t in the mood, so to avoid suspicion, he text her back stating he was working late tonight and couldn’t talk. He would call her tomorrow.