Blackmailed Ch. 02

Samuel slunk out of the gas station just as the morning sun began to cast long shadows across the pavement. Sharnise was already there, her arms crossed and her foot tapping impatiently. He gave her the keys without a word, his head bowed, the hood of his sweatshirt pulled low. He couldn't bring himself to look at her. He just wanted to disappear.

The walk to the alley was a walk of shame. Each step felt heavy, the fabric of his sweatshirt rubbing against the collar, a constant, chafing reminder of his predicament. He saw the black sedan parked at the entrance, a silent, ominous sentinel. He didn't hesitate this time. He just turned the corner and walked into the familiar darkness.

The man was there, leaning against the brick wall, nonchalantly picking at his nails. He was wearing a black business suit again.

"Good morning, sissy. Strip out of your boy clothes and kneel in front of your Daddy." The command was casual, almost bored.

Samuel complied, resigning to what he assumed was going to be another degrading ordeal. His tormentor grabbed Samuel's chin and tilted it up to look at his face.

"The collar is a good start. We can improve in the face, however. He produced a basic make-up bag and a small mirror from his pocket. "Some mascara and lipstick will help you look like a proper sissy slut."

Samuel's hadn't the slightest idea how to apply the make-up properly. He had been interested in trying during his alone time but hadn't plucked up the courage to go that far as of yet. He gave it his best try even though his hands were shaking.

To make matters even more distracting, the man stalked behind him and placed his hands on Samuel's ass. His thumb snaked its way between his cheeks and pressed softly against his ass. He leaned in close to Samuel's ear as he spoke. "After her little demonstration last night, Daddy fucked Jamie in the car. Bet you are jealous, you faggot. Your sister got a nice, deep fucking and you still had to work. Did you think about that while you were stacking shelves?"

Samuel gasped at the violation as he accidentally smudged the mascara. "Yes, Daddy," he mumbled, the shame coiling in his gut. He focused on the lipstick, trying to get the line even as the man's thumb continued to circle his entrance, a teasing, maddening pressure.

"Tell me you are jealous, sissy. Tell me you wish that was you, bent over and taking my cock like a good girl."

"I'm... I'm jealous, Daddy," Samuel stammered. He smeared the lipstick, a bright, messy crimson across his lips. He knew he was doing an awful job of his make-up.

The man spun him around and sneered at him. "You look like a clown, sissy. Don't worry, this will be part of your training."

He pushed Samuel into a kneeling position; Samuel complied without resistance. The man pulled a thick black dildo out of his bag. "This is what you will practice on before you get the privilege of Daddy's cock down your throat. You will learn to deepthroat this toy. Open wide, faggot."

Samuel opened his mouth, and the man pushed the dildo past his lips. The rubbery taste filled his mouth. He gagged as it hit the back of his throat.

"Breathe through your nose, sissy. Relax your throat." The man said, pushing it deeper. "Look at you, kneeling in an alley with a cock in your mouth, and makeup smeared all over your face. This is your natural state." He began to fuck Samuel's face with the dildo, slow and deep. Tears streamed down Samuel's face, mixing with the ruined mascara and creating dark tracks down his cheeks. He choked and spluttered, drool running down his chin.

"Messy, little slut aren't you, Samantha. Bet you can't wait to give Daddy a sloppy blowjob. Keep that throat relaxed; we are getting you halfway today." He pushed the dildo further, until Samuel's lipstick had smeared halfway down the dildo. "Good girl, Samantha. Hold it there a little longer."

Samuel gagged and coughed on the toy; the edges of his vision started going fuzzy as he struggled to breathe through his nose. The man held the dildo in place until Samuel stopped gagging. He pulled it out as soon as he saw that he had pushed him far enough. A long string of drool hung from Samuel's lips. He was panting, face red and tear-streaked.

"A respectable start for a beginner, sissy. We will have to work on that gag reflex." He reached down and wiped a stray tear from Samuel's cheek with a manicured finger. He wiped the saliva-coated dildo on Samuel's hair. "Keep the dildo and make-up. Your homework for tomorrow is to practice your makeup and deepthroating skills. Daddy expects you to make progress. Do you understand, faggot?"

"Ye-yes Daddy." Samuel croaked back, his throat feeling red and raw from the man's meticulous attention. He hoped this was the end of today's 'training'. His heart dropped as the man unzipped his trousers and began stroking his hard cock.

"Stick out your tongue, slut. Daddy likes to mark his sissy wives every day. Keeps them in their place." The man stroked himself faster, his breath hitching. "You are going to be such a pretty little sissy when we are done with you."

He grunted, and a thick stream of cum shot onto Samuel's waiting tongue. The man then moved his cock around, splattering the rest of his load all over Samuel's face and hair. "Swallow." The man commanded. Samuel obeyed, the taste bitter and salty on his tongue. The man used his cock to smear the cum across Samuel's face like it was lotion. "There, a pretty little sissy with a cum-glazed face. Go home, Samantha."

He turned and walked towards the car, leaving Samuel kneeling on the ground, naked, covered in cum, with a dildo in one hand and a bag of make-up in the other. For the second time in a row, he had to walk back to his flat in a disgusted, humiliated mess.

---

As a small silver lining, Samuel cried a little less in the shower this time. Furthermore, his absolutely exhausted state allowed him to pass out once he'd hit the pillow.

He woke up feeling somewhat rested and seemed to have an appetite back. He hadn't eaten much since the ordeal had begun due to his stomach being in knots the entire time. The first thing he did was inhale a bowl of cereal and was able to pretend his life was normal for a sweet thirty minutes.

He almost didn't notice the blackmail phone had been flashing the entire time. He winced as he saw he had an unread message. With a deep sigh, Samuel opened the message. The man had ordered him to record himself putting the buttplug up his ass and wearing it all day.

He walked to his bathroom and stared at the plug sitting on the sink. It hadn't been moved since he pulled it out of himself the day before. It sat, looking cold and imposing. Samuel set the phone to record and balanced it precariously on the soap dish. He lubed the plug up with some of the cheap, generic brand lube that the man had left him. He tried to relax as he pressed the tip of the plug against his entrance, his face flushing with shame. He slowly pushed it inside, a familiar stretch and burn.

Samuel sent the video to 'Daddy' and got an instant reply. 'Good girl. Don't forget your practice. Daddy will see you tomorrow and expects to see progress. Do not disappoint me.' Several links to make-up tutorials followed shortly after.

Samuel spent the rest of the day following the tutorials. He was a poor student at first, but he was a determined one. The fear of a poorly done 'homework' assignment was a good motivator. He made significant progress by the end of the day and was able to apply a decent layer of foundation, mascara, and a neat line of red lipstick. He was still an amateur, but he no longer looked like a clown.

The dildo 'homework' was much more difficult. He spent much of the day attempting to subdue his gag reflex, but progress was slow and painful. The tight collar around his neck hampered his attempts to relax his throat, and he gave himself a coughing fit every time the gag reflex touched the back of his throat. More than once, his coughing forced the plug out of his ass, causing him to yelp in surprise. After the third time, Samuel threw the plug and dildo across his living room in a fit of frustration.

Samuel stormed off to work in a foul mood. He barely spoke to his colleagues who were completing a stock count and stalked straight into the staff toilet to wait for them to leave.

When the store was once again his, he walked out onto the shop floor and saw Sharnise's magazine left on the counter. He opened it out of boredom and flicked through the pages. He stopped at a page with a full-page perfume advert. The model had a powerful and feminine look. Her make-up was flawless. He studied the image for a few minutes before he realized what he was doing. He slammed the magazine shut and threw it in the bin. A wave of self-loathing washed over him.

He tried to distract himself by watching a movie on his phone for a little while, but the bright light of the screen and the low hum of the freezers lulled him into a state of sleepy dissociation. Customers came and went and did little to knock him out of his stupor. Once his shift had finished, he walked home to eat a lonely meal and curl up in bed. Samuel couldn't help but be aware of how meaninglessly boring his life had become before the man walked through the doors of his work.

---

Samuel was awakened by a knock at his front door; it was the weekend, which he usually set aside for sleep and gaming. He pushed past the various strewn-about takeaway boxes that were cluttering his living room and met the delivery man at his door. He wasn't expecting a package, but he often did late-night shopping, which he didn't remember doing.

"Hi there, sir. I have a delivery for Samantha and need someone to sign for it. Is she in?" The chirpy delivery driver asked.

Samuel's blood went cold. "Oh... uh... yes, that is me." He mumbled as he scribbled a signature on the device. The driver cocked an eyebrow in slight surprise but said nothing more.

"Have a nice day, ma'am." The driver said before disappearing down the hall.

Samuel slammed the door and ripped the box open. He was confronted with a sea of pink tissue paper and an array of feminine clothing. He pulled out the items one by one. A frilly French maid outfit and apron. A pink silk dressing gown with a fluffy trim. A set of lacy white lingerie, including a garter belt and stockings. A cheap-looking blonde wig. A collection of brightly coloured yoga pants and crop tops. And to top it all off, a pair of bright pink, seven-inch stripper heels.

He threw the clothes on the floor in disgust. A note fell out of the box. 'Wear the maid outfit, wifey. Daddy will be coming over by noon and expects you to be waiting. See you soon, sissy."

Samuel looked over at the clock; it was almost ten. He had two hours to prepare himself for what was to come. He looked over at the pile of clothes, then at the dildo and makeup on his coffee table. He felt a strange sense of resignation. He had to do what he was told. He went to the bathroom and started on his makeup. He needed to get it right this time. He had spent much of the day yesterday practicing, and his hard work was certainly paying off. He wasn't sure if he should be proud of that or not. He calmed himself before applying the foundation, mascara and lipstick, this time with a steady hand. He looked in the mirror and hardly recognized himself. The face that stared back was feminine, almost pretty in a whoreish sort of way.

With his make-up done, he moved on to the clothes. He started with the white lace bra and panties; both felt uncomfortable as the lace rubbed against his sensitive nipples and rode up his asscrack. Next came the nylon stocking, which felt nice and cool against his legs, much to his shame. Lastly, he swallowed whatever small amount of pride he had left and pulled on the maid outfit. The dress felt flimsy, cheap and was barely long enough to cover his ass. The blonde wig also looked cheap; the whole ensemble made him look like a hooker. He finished the outfit by shoving the plug up his ass; the man didn't specifically order him to wear it today, but he didn't want to risk being chastised for it.

A loud knock at the door announced the arrival of his blackmailer. Samuel timidly opened the door and peeked his head round to make sure it was indeed him. The man looked him up and down with a pleased look. "Good afternoon, Samantha. Now step aside, your husband is home."

Samuel scurried out of the way as the man strode into his flat. The man grabbed Samuel by the chin and pulled him in for a deep kiss. Samuel tried not to cringe away as the man explored his mouth with his tongue. The man pulled his face away and slowly stroked Samuel's lips with his tongue. Samuel felt himself becoming lost in the man's deep blue eyes; something stirred within him.

The man broke the strange moment of intimacy by breaking eye contact and glancing around Samuel's flat. "Samantha, your flat is an absolute mess. A sissy wife needs to have more pride in her housekeeping skills. But don't worry, Daddy will teach you how to clean like a proper housewife." He pulled a pair of yellow marigold gloves and a plethora of cleaning supplies. "Start in the kitchen; I'm assuming you have a sink full of dirty dishes." He said, gesturing to the kitchen. "Don't stop until this entire apartment is spotless."

Samuel wanted to protest, but he knew it would be useless. He walked to the kitchen and looked at the mountain of dirty dishes. He sighed and pulled on the rubber gloves. He began to scrub, the hot water and soap stinging his hands. The man lounged on his sofa, casually reading a newspaper. He chuckled when Samuel exposed his plugged as while bending down to collect some trash. The man reached over and groped him, "Daddy loves to see his sissy wife properly plugged. Your slutty ass is going to look so pretty when it's wrapped around my cock." He smacked Samuel's ass hard and left a red welt on the soft skin.

Samuel yelped and jumped away from him. "Yes, Daddy," he said, his voice small and submissive.

"Carry on, slut. Daddy will give you a reward when you are finished." The man said, returning to his newspaper. He occasionally looked up to watch Samuel's progress, making comments about how he was scrubbing too slowly, or how he missed a spot.

After what felt like an eternity, the entire apartment was spotless. The floors were gleaming, the surfaces were wiped down, and the air smelled of bleach. Samuel was exhausted, sweat beading on his brow and dripping down his back. He stood in the middle of the living room, awaiting his next command.

The man put down his newspaper and opened his legs. "A good job, wifey. Now get on your knees and crawl over here for your reward."

Samuel's stomach clenched. He sank to his hands and knees, the maid dress's skirt riding up to expose the frilly white panties and the garter straps. He crawled across the clean floor, each movement feeling like a surrender. He stopped between the man's spread legs, looking up at him with wide, frightened eyes. He had practiced with the dildo, but the reality of the situation was far more terrifying.

"You've been a good little housewife, Samantha. Daddy thinks you've earned a taste." The man unbuckled his belt and unzipped his trousers, pulling out his semi-hard cock. It was bigger than the dildo, and the thought of it inside him made him tremble.

"Kiss it." The man commanded.

Samuel leaned forward and pressed a hesitant kiss to the tip, the salty taste of precum on his lips. The man let out a low groan.

"Lick it. Worship your husband's cock, you little faggot." He tangled a hand in the blonde wig, forcing Samuel's face closer.

Samuel stuck out his tongue and ran it along the underside of the shaft, from base to tip. He could feel the veins throbbing against his tongue. The man's grip tightened in his hair, guiding him, showing him how to please him. He traced the head, swirling his tongue around the slit, just as he had seen Jamie do the day before. The taste was musky, overwhelmingly male, and it filled his senses.

"Take it in your mouth, sissy. Show me what you learned." The man's voice was a low growl.

Samuel opened his mouth and wrapped his lips around the head. He sucked gently, his tongue flicking against the sensitive underside. He remembered the practice with the dildo and tried to relax his throat, taking him in deeper. He gagged slightly, but pushed through it, determined not to disappoint. He bobbed his head up and down with the rhythm he had practised. He could feel the man's cock growing harder, filling his mouth. He looked up and locked eyes with the man. Unsurprisingly, the man had a look of pure satisfaction plastered over his face. Samuel felt a strange feeling of relief blossom in his chest, the first time he had felt even slightly relaxed over the past days.

"Good girl, this feels right, doesn't it? You are a natural-born cocksucker." The man pulled Samuel's mouth off his cock and leaned in closely. "Do you want to be a good sissy wife for Daddy?"

Samuel blushed and swallowed before he answered, "Yes, Daddy. I want to be a good sissy wife for you." He was surprised at the sincerity in his own voice.

"Are you ready to swallow Daddy's cum, slut?" The man asked, stroking himself with one hand while still holding onto the wig with the other.

"Yes, Daddy, I am ready," Samuel said. He wasn't sure if he meant it or not, but he knew what the expected answer was.

The man pushed Samuel back down onto his cock. He started to thrust his hips, fucking Samuel's face with a steady rhythm. "That's it, take it all. You're going to be my little cumdump." He moaned, his thrusts becoming faster and more erratic. "Swallow every last drop, you filthy whore. Don't you dare spill a drop."

With a final, deep thrust, the man's cock pulsed in Samuel's mouth. Hot, thick cum hit the back of his throat, and he swallowed instinctively. It was bitter and salty, but he forced it down, just as he was told. He kept sucking until the man was completely spent, then he pulled away, a small trickle of cum escaping from the corner of his lips.

"Clean me up." The man ordered.

Samuel dutifully licked the man's cock clean, from tip to base, until there was no trace of his release left. He sat back on his heels, the taste of the man still lingering in his mouth.

"Good girl, you are a fast learner. Now get up." The man said, pulling Samuel to his feet. "Bend over the couch; good girls get rewarded." The man forcibly bent Samuel at the waist and put his hands on the back of the couch. His ass was high in the air, the frilly skirt of his maid outfit bunched up around his waist. The man slowly pulled the plug out of Samuel's ass. He felt a sense of loss and emptiness as the plug was removed. The man took a moment to assess Samuel's gaped hole. "Hmmm, not quite stretched enough for my cock just yet. Daddy doesn't want to break his new sissy wife." He picked up the pink dildo from Samuel's table and smeared it with lube.

"Daddy is going to fuck you with this toy. It will get you ready for the real thing." The man said as he pushed the dildo into Samuel's ass. The rubbery object slid in easily, and Samuel let out a small moan. "Do you like that, slut? Do you like having your sissy hole filled?"

"Yes, Daddy," Samuel whimpered, pushing back against the dildo.

The man began to fuck him with the toy with long, slow strokes. "Tell me you want more. Beg for it."

"Please, Daddy, fuck me harder," Samuel begged, surprised by the words coming out of his own mouth.

"Good girl," the man said, increasing the pace of his thrusts. He reached around and grabbed Samuel's cock, which was now hard and straining against the lacy panties. "Look at you, getting all turned on from being fucked in your sissy hole. You really are a faggot, aren't you?"

"Yes, Daddy, I'm a faggot," Samuel moaned, his body trembling. He could feel an orgasm building, a pressure in his balls that was all-consuming. He was completely lost in the sensation and the character the man was forcing him to play. "I'm close to cumming, Daddy."

"Not yet, slut. Daddy wants you needier than that." He taunted, releasing his hand from Samuel's cock. Precum was starting to leak through his thin, lacy panties. "Bounce your pretty ass on that toy, my little sissy slave."

Samuel started to rock back and forth, impaling himself on the dildo. The movement felt natural, almost instinctual. He could hear the squelching sounds as the toy moved in and out of him.

"Are you a sissy who loves anal?" The man asked as he smacked him across the ass again, causing Samuel to yelp in a mixture of pain and pleasure.

"Yes! Yes! I'm a sissy who loves anal!" He sobbed, tears of frustration and pleasure streaming down his face, the makeup running down his cheeks. The humiliation of the act was at odds with the intense pleasure he was feeling.

"Then cum for me, sissy." The man commanded, grabbing hold of Samuel's cock again and stroking it in time with the thrusts of the dildo.

Samuel's body convulsed as a powerful orgasm ripped through him. His cock spasmed over and over, making a mess of his new panties. He had never come so hard in his life. The man congratulated himself as he wiped his cum-slick hand over Samuel's face, further smearing his already messy make-up.

Samuel collapsed forward onto the sofa; his breath was heavy and ragged. He felt a confusing mix of shame, relief, and a strange sense of satisfaction. The man pulled the dildo out of his ass and left it on the floor. He zipped up his trousers and straightened his tie.

"Good girl, Samantha. You have potential." The man said with a smirk. "We're making real progress."

He walked over to the door and paused before leaving. "Catch your breath and clean up. Jamie will be visiting you later. It'll be nice to spend some time together. We're your new workout clothes and your plug. See you tomorrow, sissy"

The door closed, and Samuel was left alone. He lay in his own sweaty mess, the cum drying on his face and in his panties. He did manage to pull himself onto his couch before he passed out.

---

Samuel was awoken by the doorbell. He grimaced from the feeling of dried cum on his face and the pain of his stretched ass.

The doorbell was still sounding off impatiently. He pulled himself up from the couch, still dressed in the now dishevelled maid outfit. He stumbled to the door and opened it to see an effeminate young man with shoulder-length pink hair and an eyebrow piercing.

He was wearing a baby blue velour tracksuit with the tracksuit panties riding low on his hips, purposefully exposing his panty line. He practically leapt forward and embraced Samuel in a tight squeeze.

"Samantha! So good to see you again! I never got to introduce myself properly; I had a mouth full of Daddy's cock after all! I'm Jamie!" He said with a giggle, bouncing on the balls of his feet. He spoke with a high-pitched, girly lilt.

Samuel was taken aback. This was a completely different person from the gimp he saw the other day. Samuel recognized his bright eyes, however. Jamie seemed to be genuinely friendly, which took him by surprise. "Uh, nice to meet you too, Jamie."

Jamie invited himself in, skipping into the living room and making himself at home on the couch. "Daddy sent me over to hang out and get to know my new sister! Have you had lunch yet?" He asked, pulling out a large tote bag that was emblazoned with a tacky "Princess" logo.

"No, I just woke up," Samuel said, still feeling groggy and disoriented.

Jamie clapped his hands together with glee. "Perfect! I'll make us some lunch while you get changed. Daddy's friend runs an amazing workout class which will rock your world!"

Samuel was too exhausted to protest. He went to his bedroom and fished out the gym clothes from the package he was given. A hot pink sports bra and matching yoga pants, both made of a shiny, spandex material. The pants had "Juicy" emblazoned across the rear in bold silver letters. There was also a pair of pristine white trainers. He changed into the clothes, the spandex feeling tight and constricting. He avoided looking in the mirror, not wanting to see how he looked in the outfit.

When he returned to the living room, Jamie had laid out a spread of salads and fruit on the coffee table. "Daddy always says it's important for his sissy slaves to eat healthy. He's kind of like that. You didn't have much in the fridge, so it's lucky I brought food for both of us!"

"Did you choose to live like this, or were you blackmailed as well?" Samuel blurted out. The question had been burning inside him since Jamie's brazen display at the gas station.

Jamie's cheerful demeanour faltered for a second. He sighed and picked at an imaginary piece of fluff on his velour tracksuit. "I guess you could say I was blackmailed. But I was already a sissy in my heart long before Daddy found me. He just gave me a little push in the right direction. He didn't have to blackmail me for long; I realized I was much happier as a sissy. And I am so happy now. You will be too, I promise."

They ate in silence for a few minutes until Jamie began to fill the silence with his upbeat nattering. Samuel sporadically replied, still astonished by the insanity of his situation. Once the meal was finished, Jamie clapped his hands and declared it was time for them to head out. As Samuel rose to his feet, Jamie surprised him by pulling him into a passionate kiss. Jamie's hands explored Samuel's body as his tongue explored his mouth, causing Samuel to whimper into the kiss. A dainty hand found its way down the back of Samuel's yoga pants.

"Oh no! Samantha, you almost forgot to put your plug in! You would have been feeling empty all day! That wouldn't do at all." Jamie said as he broke the kiss. He skipped to Samuel's bedroom and returned with the plug. He coated it in lube before telling Samuel to bend over. He peeled Samuel's tights down to his knees and spread his ass cheeks to expose his hole. It had become red and puffy from the treatment earlier today.

Jamie cooed in genuine concern, "Oh, you poor baby, Daddy really worked you over, didn't he? Don't worry, it gets easier!" Samuel gasped in pleasure as he felt Jamie's tongue lap at the sensitive ring of muscle. He felt his ass and balls be lathered with Jamie's saliva; it was a new sensation. One which he did not detest.

Jamie's own moans joined Samuel's, "Mmmm, I just love eating boy-pussy. Feels so gooood." Jamie murmured into Samuel's ass. After a few more licks, he pressed the plug against Samuel's entrance. He pushed it in with a wet schlick and pulled the yoga pants back up. "There, all plugged up and ready to go!"

Samuel endured a humiliating thirty-minute walk to the private gym. Jamie held his hand the entire way, loudly reminiscing about the various debauched activities he had been up to. Samuel kept his head down, focusing on the feeling of the ground beneath his feet. He tried to ignore the fullness in his ass and the eyes resting on the collar around his neck.

The gym was discreetly tucked away behind some boutique shops in the nicer part of the city. The windows were tinted, and there was no sign on the door, just a small, polished brass plaque with a single, stylized letter 'S'. Jamie buzzed them in with a keycard.

The gym itself was pristine, all polished concrete floors and state-of-the-art equipment. A pretty blonde woman sat at a modern reception desk; she recognized Jamie instantly. "Good afternoon, Jamie. Who's your friend?"

"Hey, Chloe! This is Samantha, my new sister! She's here for her first class!" Jamie beamed.

Chloe's expression was professionally blank, but her eyes lingered on the collar for a moment too long. "Of course. Down the hall, third door on the left. Enjoy your workout." She said, her tone laced with a knowing amusement.

The workout room was a large, open space with wall-to-wall mirrors and a polished wooden floor. There were about a dozen older women wearing lycra and spandex. The instructor was leading them through some initial stretches. Samuel was immediately intimidated by the sight of them. They looked like they all belonged in high society.

The instructor was a woman in her late forties, with a stern, athletic build and her greying hair tied back in a severe bun. She stopped the class when Jamie and Samuel entered. "Ladies, we have a new member joining us today." Her eyes scanned over Samuel, a flicker of something unreadable in her gaze. "This is Samantha. Make her feel welcome."

The women all turned to look at Samuel; unadulterated hunger was plastered on their faces as they looked him up and down. He felt like a piece of meat. He felt more naked than when he was actually naked in front of the man. The women in the class all had a look like they were accustomed to getting their way.

The instructor marched up to Samuel. "I am Mistress Veronica. In my class, you will do as I say, without question or hesitation. You will address me as Mistress. Understood?" Her voice was sharp, and left no room for argument.

"Yes, Mistress," Samuel replied, his voice trembling slightly.

"Good. Now get into position at the front of class. The ladies enjoy the view of a new sissy's ass." She said with a cruel smile. The other women tittered. Jamie gave him an encouraging pat on his plugged ass as they found their space at the front. The women's haughty gazes bored into the back of Samuel's head.

The class itself was completely overstimulating, physically and emotionally. Mistress Veronica put them through a gruelling set of aerobic routines. The mirrors quickly became clouded with sweat; the air was thick and heavy. Samuel was not an athletic person and his velvet attire did nothing to help him cool down. He was drenched in sweat, struggling to keep up with the more experienced Jamie.

"Ladies, focus on form." Mistress Veronica commanded, her sharp voice cutting through the pounding music. "Samantha, deeper into that lunge. I want to see your thighs parallel to the floor. Your husband won't want a wife with lazy glutes." She strode over and smacked his ass with a riding crop that seemingly materialized from thin air. "And keep that back arched. Little faggots like you should always present their holes properly."

The women in the class watched with rapt attention, their eyes glinting with a predatory light. He could hear their whispers. "Look at that blush." "He has such a plump little ass." "I wonder if he'll be at the next party."

Next came a long and painful stretching session. Mistress Veronica manhandled Samuel into a range of strenuous positions, each one more humiliating than the last. She forced him into the splits in front of the entire class, her strong hands pushing his legs wider until the fabric of his yoga pants strained at the seams. He could feel the plug shifting inside him with each stretch, a constant, maddening reminder of his situation. Samuel glanced over at the other women and was surprised to see they were peeling off their lycra tights. A couple of them were stepping into strap-on harnesses. "You'll love what comes next, sissy. We are going to train that asshole whilst you eat sweaty pussy." Mistress Veronica whispered to him. The thought of servicing these strangers made him feel physically sick.

He was so lost in his thoughts he didn't hear the command. Mistress Veronica's crop came down hard on the back of his thigh. "Did I give you permission to daydream, sissy?" She barked. "When I give an order, you obey instantly. Or perhaps you'd prefer a more... public punishment?"

"No, Mistress. Sorry, Mistress," Samuel stammered, his face burning with shame. She grabbed him by his collar and pulled him towards a woman who was waiting with her legs open, her plump, sweaty pussy on full display. Jamie was standing to the side recording the whole scene on his phone.

Samuel knew if the man saw him resist, he would be in deep trouble. He could only guess at the consequences if he underperformed. He knelt before the woman and leaned in, the musky, salty scent of her sweat and arousal filling his nostrils. He stuck out his tongue and gave a tentative lick.

The woman let out a satisfied sigh. "That's it, sissy. Don't be shy. Show Mistress Veronica what a good little pussy-eater you can be." She grabbed the back of his head and forced his face deeper into her slick folds.

As he was desperately trying to please the woman, he felt a pair of hands on his hips. He looked back to see Mistress Veronica lining up her strap-on with his plugged ass. "Stay still, Samantha," she commanded. "Your Daddy told me to train your ass some more." She yanked the plug out in one swift motion, leaving him feeling suddenly empty and exposed. Before he could adjust, she began to push the strapon inside him.

It was bigger than the dildo, and the sudden stretch made him cry out. His cries were muffled by the woman's pussy. "That's it, moan into my cunt, you little slut," she groaned, grinding her hips against his face.

Mistress Veronica began to fuck him with a steady, punishing rhythm. Each thrust sent a jolt of pain and pleasure through his body. He felt completely and utterly violated, used from both ends by these dominant women. And yet, to his horror, he felt his cock become hard in his knickers.

The woman he was eating out pulled him deeper into her cunt with a vice-like grip. She came directly into Samuel's mouth, her juices spurting up his nose, causing him to cough and sputter.

He was turned onto his back just in time to see the next curveous women face before she smothered him with her sweat-covered ass. He tried to breathe but found only her flesh as she wiggled her butt back and forth.

"Lick my asshole, you dirty sissy. I expect a thorough job," She demanded. He obeyed, his tongue circling the tight ring of muscle. The taste was earthy and bitter. He could hear the other women cheering him on. "That's it, get your tongue in there!" "Look at him go, he's loving it!"

As he was pleasuring the woman, Mistress Veronica continued her assault on his ass. "You like that, don't you, faggot? You like being fucked like the sissy you are," she taunted, smacking his thighs with her open palms in between thrusts.

He was passed from woman to woman, forced to pleasure each of them in turn. He licked and sucked and probed until his jaw ached and his tongue was raw. He was fucked by Mistress Veronica and a few of the other women who were eager to try out their strapons on the new sissy. By the end of the session, he was a trembling, sweaty mess, covered in their juices and cum.

As the class came to an end, the women slowly started to get dressed, their predatory smiles replaced with polite, indifferent expressions. Mistress Veronica unstrapped her harness and tossed it aside. "Good work today, ladies. And Samantha," she said, her voice softer now, but no less commanding. "You have potential. I'll see you next week."

Jamie helped him to his feet, chattering away as if nothing out of the ordinary had happened. "You were amazing, Samantha! You looked like you were having so much fun!" He handed Samuel a bottle of water and a small, wrapped packet. "Here, a little gift from one of your admirers. Mrs. Davison said you had a very talented tongue. She would love to use you again."

Samuel stared at the packet in his hand. It was a hundred-dollar bill, folded neatly. He felt physically sick. He had just been whored out, and he'd been paid for it.

The walk back to his flat was a blur. They stopped at a shop on the way back for some groceries. Samuel barely noticed all the other shoppers staring at his collar and ragged appearance, other than his mind whirring from the ordeal of the exercise class. Being completely truthful to himself, he had fantasized a great deal about being used by a group of women. In reality, it had been horrible.

When they got back to his flat, Jamie suggested that Samuel put the shopping away while he called their Daddy. Samuel numbly did as he was told, stacking cans in the cupboard and putting milk and vegetables in the fridge.

He could hear Jamie's high-pitched, giggly voice from the living room. "Yes, Daddy... she did so well... Mistress Veronica was very impressed... Yes, I'll make sure she practices... Okay, Daddy... I love you too! Bye!"

Jamie bounced into the kitchen, a bright smile on his face. "That was Daddy! He's so proud of you! He said you earned a special treat tonight. We are having a movie night, just the two of us!" He clapped his hands with glee. "We can do face masks, paint our nails, and I can give you a proper makeover! It'll be so much fun!"

Samuel just nodded, too exhausted to argue. He excused himself to use the restroom to give himself ten minutes of peace to cry on the toilet. He returned to find Jamie having set up a small spa I his living room. An array of coloured nail polishes and face masks were laid on his living room table. Apparently, he never left his house without them in his handbag.

Jamie excitedly patted his lap, signalling for him to sit. Samuel sat down with a sigh. Jamie applied a cooling cucumber face mask onto Samuel's face before gently massaging a sweet-smelling cream into his hands. The smell of lavender filled the small room as Jamie worked on him. The gentle touches and sweet smells were a stark contrast to the rough, demanding hands he had been subjected to earlier that day. He found himself relaxing into Jamie's touch, his body betraying him once again.

"You have such a pretty face, Samantha," Jamie said, his voice soft. "And your hands are so delicate. You'll make a beautiful woman."

Samuel didn't respond. He just closed his eyes and let Jamie work. He painted his nails a bright, sparkly pink, the same colour as the collar around his neck. Jamie then started on his makeup. He applied a layer of foundation, then a sweep of shimmery eyeshadow and a coat of mascara. He finished with a slick of glossy pink lipstick. He held up a small mirror for Samuel to see.

"There," Jamie said, a proud smile on his face. "What do you think?"

Samuel looked at his reflection. He saw a stranger. A pretty, feminine stranger with sparkling pink nails and glossy lips. He felt a strange sense of detachment, as if he was looking at someone else. He didn't recognize the person staring back at him. The face that stared back was not his own.

"It's... different," he managed to say, his voice barely a whisper.

"Different is good, Samantha," Jamie said, patting his cheek. "Different is what we're going for. Would you like to fix us some drinks? I'll find us a movie we can enjoy."

Samuel once again did as he was told, and he fetched two glasses of wine for him and his guest. He returned to Jamie browsing a gay porn website on his TV; he seemed to be looking for a specific video. He eventually found it and pressed play. The movie started with a young man being roughly manhandled by two older men. They tore off his clothes and forced him to his knees. The scene was eerily similar to what Samuel had experienced earlier that day.

Samuel felt a knot of unease in his stomach. He wasn't sure he could watch this. But Jamie seemed to be enjoying it. He was sipping his wine, his eyes glued to the screen. He reached over and took Samuel's hand, lacing their fingers together. His touch was gentle, but there was a possessiveness to it that made Samuel's skin crawl.

"This is one of my favourites," Jamie said, his voice low and husky. "Daddy showed it to me when I was first starting. It helped me understand my place."

The movie continued, the scenes becoming more and more intense. The young man was tied up, spanked, and used in every way imaginable. He was crying and begging, but it was clear he was enjoying it. Samuel found himself getting lost in the movie, his own experiences from the day flashing through his mind. He could feel the heat rising in his cheeks, and a familiar stirring in his loins.

Jamie seemed to notice. He leaned in close, his breath warm against Samuel's ear. "You like this, don't you, Samantha? You like seeing him being used like a little slut. Not the first time you've jacked off to gay porn, is it?"

Samuel didn't answer. He just stared at the screen. He could feel Jamie's hand on his thigh, slowly creeping up towards his crotch. He wanted to push him away, but he couldn't.

Jamie's fingers found the growing bulge in Samuel's yoga pants. He rubbed it gently, causing Samuel to gasp. "See? I told you you'd like it," Jamie whispered, a triumphant smile on his face. "You're a sissy gayboy, just like me. And it's time you accepted it."

He unzipped Samuel's pants and pulled out his cock. It was hard and throbbing. Jamie wrapped his fingers around it and started to stroke it, matching the rhythm of the thrusting on the screen. Samuel leaned his head back against the couch, a low moan escaping his lips. He was completely lost in the sensation, the shame and the pleasure warring within him.

"You're so beautiful when you're like this, Samantha," Jamie said, his voice full of admiration. "So submissive and willing. Daddy is going to be so pleased."

He leaned in and took Samuel's cock into his mouth. He sucked him with a practiced ease, his tongue slowly swirling around the head, his lips gently caressing the shaft. Samuel had never felt anything like it. He tangled his hands in Jamie's pink hair, pulling him closer. He could feel the pressure building, his balls tightening. He was close.

"Not yet," Jamie said, pulling away with a wet pop. He stood up and stripped off his velour tracksuit, revealing a matching set of black lace lingerie. He looked stunning. He was slender and toned, with smooth, hairless skin. His cock flattened by a restricting metal cage. "How about you bend me over your coffee table while we finish watching the movie?" He suggested with a wink. He sauntered over to the coffee table and pulled out his plug, giving it a long seductive lick. He then bent over the table, presenting his ass to Samuel. The straps of the thong framed his perfect, hairless ass.

Samuel hesitated. This was a line he wasn't sure he was ready to cross. The man, the women at the gym, that was different. That was forced. But this... this felt like another big step down the slippery slope he was on. The movie continued to play, the sounds of moaning and slapping filling the room.

"I... I don't know if I can..." Samuel murmured. He finally had to admit his greatest shame to another person. "I've never had sex with anyone before. Not a woman, and definitely not a man. These last few days have been so overwhelming." He could feel tears rolling down his eyes.

Jamie turned his head to look at him, a sympathetic look on his face. "Oh, you poor, sweet baby. Your first time! Did Daddy know you were a virgin?" He asked with genuine surprise.

Samuel shrugged his shoulders. "I assume he knows. I mentioned, from what I posted on the forums, that my lack of experience and crippling porn addiction was pretty evident." He looked down at the floor, ashamed.

Jamie got up and cradled Samuel's face in his hands, wiping away his tears with a thumb. "Hey, don't you worry about that. We can take it slow. Let's just focus on making you feel good." He said, leading him back to the sofa. He resumed stroking Samuel's cock, this time with a gentler touch. "Just relax and watch the movie. Let your sister take care of you." He kissed him again, a soft, lingering kiss that was full of tenderness.

Samuel melted into the kiss, his body relaxing. He let Jamie take control, his hands and mouth exploring him with a gentle curiosity. He felt a sense of surrender, not out of fear, but out of a strange, newfound comfort. Jamie's touch was different. It wasn't demanding or punishing. It was... affectionate.

Jamie moved to straddle Samuel's lap, the lace of his panties brushing against Samuel's aching cock. He guided the tip to his slick, lubed hole. "I've been wearing a plug all day too. I'm always ready for Daddy or a sister." He explained. He slowly lowered himself onto Samuel, a gasp escaping his lips as he took him in. He felt impossibly tight, a hot, velvet vice gripping Samuel's cock. "Just let me do all the work, Samantha." He whispered.

Jamie started to rock back and forth, his movements slow and deliberate. He ground his hips against Samuel, taking him deeper with each pass. He took Samuel's hands and placed them on his chest, encouraging him to touch him.

Samuel's hands roamed over Jamie's smooth skin, tracing the lines of his muscles, finding his pert nipples. He looked up at Jamie's face, his eyes closed in ecstasy, his lips parted in a silent moan. He was beautiful. And for a moment, Samuel forgot about the blackmail, the humiliation, the fear. He lost himself in the moment, the porn in the background melted away, and he focused on the pleasure of the gorgeous man who was riding his cock.

"You feel so good inside me, Samantha," Jamie moaned, his voice a breathy whisper. "You're so big. I can feel you stretching me." He leaned down and kissed Samuel again, a deep, passionate kiss that stole his breath.

Samuel's hips began to move of their own accord, rising to meet Jamie's downward thrusts. He was getting closer, the pressure in his balls building to an unbearable level.

"Cum for me, Samantha," Jamie begged, his voice hoarse with desire. "Fill my boy pussy. I want to feel you explode inside me."

With a final, powerful thrust, Samuel buried himself deep inside Jamie. A guttural moan escaped his lips as he came, spilling himself into him. He came harder than he had ever cum in his life, his body convulsing with the force of it. He felt like he was pouring out all the fear and frustration of the last few days, leaving him empty and spent. He collapsed against the sofa, his chest heaving.

Jamie stayed on top of him for a few minutes, their bodies entwined. He stroked Samuel's hair, murmuring soft words of encouragement. "That was beautiful, Samantha. How do you feel?" He asked.

Samuel's mind was a complete blank. He looked into the warm and genuine eyes of the man who was still impaled on his cock. He felt surprisingly calm. Being a virgin in his twenties had weighed on him for some time; it's not how he expected it to go, but he felt surprisingly okay.

"I feel... good." He said, a little surprised by his own admission. He expected to feel regret, shame, or disgust. Instead, he felt a sense of relief, a release of tension he didn't even know he was carrying.

Jamie climbed off of Samuel's cock, a trickle of cum leaking from his ass. He knelt and cleaned Samuel's cock with his tongue, licking him clean with a practiced ease. "You taste delicious, Samantha," he said with a giggle. "We'll have to do this again soon."

Samuel watched him, a strange feeling of fondness washing over him. Jamie was a victim, just like him. But he had embraced his role, found a twisted sort of happiness in it. Maybe there was something to that.

Jamie's phone pinged, and he let out a signature giggle. "Oh, Samantha! Exciting news! Daddy will be over tomorrow! He's going to let me watch you get fucked in the ass for the first time!"

And just like that, the calm Samuel was feeling evaporated.