Tim’s Secret Fascination Begins
Tim was 22 when he first slipped into his sister Lucy’s clothes in the summer of 2020. Alone in his parents’ house in Manchester’s Didsbury suburb, while Lucy was at a mate’s party and his mum Ellen was away on a business trip, he crept into Lucy’s room. A light blue summer dress (80 cm, thin straps) lay on her bed. Tim held the soft cotton fabric, pulled it on, and stood before Lucy’s full-length mirror. His slim frame, blond hair – the sight was electric. He rummaged through her drawer, slipped on a pair of white lace knickers (size 8), and tried her sandals (size 6), which just about fit. For an hour, he posed around the house, caught between shame and thrill. When he heard Lucy’s key in the lock, he tore the clothes off, stashed them, and pretended to read in the lounge. Lucy didn’t notice a thing, but Tim was hooked.
Mum’s Sexy Wardrobe
By autumn 2020, Tim discovered his mum Ellen’s wardrobe. Ellen, a stylish woman in her fifties, had a knack for sultry outfits. Her closet was a treasure trove: silk dresses, tight leather and velvet skirts, cashmere jumpers, sheer tights, lace lingerie from Agent Provocateur and La Perla. Tim was drawn to a black lace bra (34B) with matching thong, a red satin negligée (size 10, 70 cm), a fitted black leather skirt (size 10, 45 cm), and hold-up stockings with lace tops. He often wore Ellen’s black stilettos (10 cm, size 7), red platform pumps (12 cm), or silver strappy sandals (8 cm). Once, he paired a deep green silk dress (size 10, knee-length) with a suspender belt and felt like a film star. Another time, he laced himself into a black corset (size 10, 60 cm waist) with a velvet skirt (size 10, 50 cm), barely able to breathe but loving the transformation.
More Frequent Crossdressing and Nighttime Ventures
Over the next months, crossdressing became a ritual. Tim wore Lucy’s skinny jeans (size 8), crop tops, mini skirts (35 cm), or Ellen’s silk blouses, corsets, and negligées. He secretly used Lucy’s make-up: red lipstick, dark eyeliner, mascara. In spring 2021, he ventured out at night in Ellen’s grey wrap dress (90 cm), hold-ups, and ballet flats (size 7). In Heaton Park, 2 miles from home, he felt the evening breeze on his stockinged legs. Passing a café, he spotted Ellen with a friend – she frowned, as if recognising something. Tim darted into a side path, heart pounding. Back home, he noticed a scuff on the flats, which he covered with shoe polish.
In summer 2021, Tim moved to a flat in Chorlton and bought his own clothes: black knickers (size 8), hold-ups, an H&M dress (size 8, 85 cm), a white silk blouse (size 10). He hid them in a suitcase on top of his wardrobe but still used his family’s stuff when visiting. At night, he roamed Chorlton as “Mia” (his secret name), wearing Ellen’s cream silk blouse (size 10) and tight denim skirt (size 10, 40 cm) or Lucy’s belly-baring tank top with hotpants (size 8). Once, he wore Ellen’s black lace top (size 10) and trainers for a walk in Fallowfield, feeling invisible yet exhilarated.
Close Calls
In winter 2020, Tim wore Lucy’s red mini skirt (35 cm) and white top when Lucy came home early. He wiped off make-up, hid the skirt in the laundry, and claimed he’d accidentally washed it. Lucy bought it. In spring 2021, he tried Ellen’s satin negligée and suspenders when his dad rang to say he was popping by. Tim stuffed the clothes in the wardrobe, later finding a stocking under the sofa, which he quickly hid.
In summer 2021, Tim forgot to take off Ellen’s cream silk blouse (size 10), paired with jeans. He was in the lounge when Ellen walked in. “Tim, why’re you wearing my blouse?” she snapped. Tim stammered he’d mixed it up with his shirts in the laundry basket, saying it looked similar. Ellen frowned but believed him, telling him to be more careful. Tim, relieved, hid the blouse straight away.
In autumn 2021, Tim wore Lucy’s black crop top (size 8) and jeans when Ellen came into the lounge unexpectedly. The top was subtle, like a tight tee, and the jeans hid the lace knickers underneath. Ellen didn’t seem to notice, chatted about her day, and left. Tim changed, grateful for his luck.
The Party Encounter
In summer 2022, Tim made his boldest move. In Ellen’s black lace dress (size 10, 80 cm), hold-ups, black 8-cm pumps (size 7), and Lucy’s make-up (dark eyeliner, red lipstick, false lashes), he went to an open-air party in Platt Fields Park as “Mia”. A blonde wig (shoulder-length, bought online) and Lucy’s clutch completed the look. He felt confident, unseen.
At the bar, he ran into his mates Max and Josh, who didn’t recognise him. “Alright, love,” Max said, offering a drink and slipping an arm around Tim’s waist. Josh flirted, pulling him to dance. On the dancefloor, Tim felt Josh’s hands on his hips while Max whispered suggestive remarks and invited him for a “walk”. Tim, nervous but flattered, mumbled he needed the loo and bolted. In the shadows, he yanked off the wig, wiped the make-up, and legged it home, both thrilled and terrified. The encounter reminded him of his isolation – nobody knew “Mia”, and the mates who teased Tim had fancied him as a woman.
The Fascination Grows
By his 25th birthday in June 2025, Tim’s crossdressing was central to his life. He loved the feel of silk, lace, nylon, the tightness of corsets, the click of heels. In his flat, he dressed up daily, posing in mirrors, watching crossdressing porn that fed his fantasies. The fear of discovery – Ellen’s glance in Heaton Park, the party with Max and Josh, the near-misses – heightened the thrill. He’d never pictured himself with men as a woman, but the party stirred something: the power of being desired. This secrecy shaped him when his mates took him to Clara on his birthday.
The Birthday and the Surprise
Tim glanced nervously around as his mates roared with laughter, shoving him through the grubby door of an old terraced house in Manchester’s city centre into a dim hallway where a woman waited. They’d been celebrating Tim’s 25th birthday, a do he’d have skipped if anyone had listened. But his mates insisted, and Tim, as usual, went along. After a night hopping from swanky pubs on Deansgate to a curry house in Rusholme, they sprang their “gift” on him.
It was no secret among them that Tim was a virgin – a confession spilled after too many tequila shots in a Fallowfield strip club. Whenever it came up, Tim trotted out the same line: he was waiting for the right person, it should be special, and no, despite their jibes, he wasn’t gay.
Tim was telling the truth, but not the whole truth. Two things he couldn’t admit held him back. First, he struggled to talk to women, especially confident or attractive ones. He’d stammer, get flustered, and never got past a first date, let alone anywhere near sex. He couldn’t tell his mates that, even if they’d been understanding – which they weren’t. Second, and bigger, was that Tim was a crossdresser and kept it deeply hidden.
Since he was 22, when he tried Lucy’s summer dress, he’d been hooked on women’s clothes. He wore Lucy’s jeans, tops, mini skirts, and later Ellen’s silk dresses, leather skirts, corsets, and lingerie. He’d nearly been caught: Lucy almost spotted him in her mini skirt, his dad showed up while he was in Ellen’s negligée, and in Heaton Park in 2021, Ellen nearly recognised him in her wrap dress. In summer 2022, at a Platt Fields party, Max and Josh flirted with him as “Mia”, clueless it was him. In his Chorlton flat, he hid his own clothes – knickers, stockings, dresses – in a suitcase and dressed up daily. Once, he forgot to take off Ellen’s silk blouse and blagged his way out; another time, Ellen missed Lucy’s crop top on him. These moments, plus nighttime outings, defined him: a life of shame, thrill, and secrecy.
The Reveal and the Pressure
As he was pushed to the door, Tim recalled his mates sniggering for days before his birthday, dodging his questions. Now, at the door, the secret was out. They’d booked a prostitute to take his virginity – not just any, as one slurred, but a pricey, top-notch one, highly recommended. Who’d recommended her, he didn’t say, but Tim reckoned at least one mate had been a client.
Despite Tim’s feeble protests, his mates said it was time, and with everything sorted, the woman was waiting. They were outside her place on Oxford Road. One mate rang the bell, announced Tim, the birthday boy, and seconds later, the door swung open.
Shoved inside amid crude cheers and demands for a full report in the morning, Tim saw a stern-looking woman eyeing him in the dim hallway.
“Shut the door, Tim,” she ordered.
Tim obeyed, closing the door as his mates laughed and staggered off.
The locks clicked shut, trapping him with the woman.
“Good, follow me.”
Tim turned to see her heading down the hall. A door opened, light spilling out as she entered the room.
The First Room and the Encounter
Tim followed into a small, sparsely furnished room – a single armchair, a sofa, and a switched-off telly. A few Lake District landscapes hung on the white walls, but otherwise, it was bare.
The woman sat in the armchair, and Tim got a proper look at her. She had dark brown hair tied in a ponytail, striking green eyes, and a mouth like a thin slash of red lipstick. She frowned at Tim, as if unimpressed. She wore a black silk dressing gown, tied tight, revealing only black stockings or tights and black strappy stilettos.
“I’m Clara, and you, Tim, are, as I hear, still a virgin and want to change that.”
Tim stammered at her bluntness, unable to speak.
“What’s up?” Clara asked sharply.
Tim shrugged. “My mates… they, uh, set this up, I…”
She nodded. “Got it.”
“So, why’re you still a virgin? Not into women, maybe blokes? Or something else holding you back?”
Tim stood frozen, staring at Clara. She was stunning, confident, and controlling – the kind of woman who left him tongue-tied.
Clara took his silence as a clue to something deeper. “So, it’s some fetish keeping you back. Well, lucky you, I’m just the person to explore that fetish with you.”
Tim stayed mute, mouth slightly open in shock.
Clara pressed on: “So, is it spanking, bondage, tying someone up, domination, pet play, watersports, sounding, pegging, forced chastity, infantilism, crossdressing, sissification?”
Tim listened as she listed fetishes, some familiar, others not. At “crossdressing”, he couldn’t help blushing and looking down – a reflex from two years of secrecy, from Lucy’s clothes to Ellen’s lingerie to the party with his mates.
Clara pounced on it. “Crossdressing, eh? That’s the reason? Are you a girly lad who loves wearing pretty knickers and playing at being a woman?”
Tim, desperate to guard his secret, stammered: “I, no, it’s…”
Sighing, Clara softened her tone. “It’s alright, Tim. This is a safe place to play with your little fetish, and I’ve got just the thing for you. You’ll love it.”
The Transformation
Clara stood, smoothed her dressing gown, and brushed past Tim out of the room. “Follow me, Timmy-bear.”
Without thinking, Tim trailed Clara, watching her hips sway hypnotically as she climbed the stairs at the hall’s end.
Upstairs, through an open door into a brightly lit room, Tim entered. A large double bed with a red velvet throw dominated the space, and he caught his reflection in mirrored wardrobe doors opposite.
Clara waited till he was inside, then shut the door behind him.
“Now, my Timmy-bear,” she said, “first things first: strip off, and while you do, I’ll find something sexy for you to wear.”
Tim opened his mouth to protest, but Clara went “Tch, tch” and pressed a finger to his lips.
“No talking for now, just doing.”
Tim had no real choice but to obey. His lack of confidence and years of secret crossdressing – from Lucy’s dress to Ellen’s corset – left him unable to argue or bluff his way out.
Slowly, he shed his clothes, piling them on the bed.
Meanwhile, Clara rifled through the wardrobes behind the mirrored doors, laying out garments on the bed.
Once stripped, Tim stood in his boxers, hands nervously covering his crotch.
Without turning, Clara asked his shoe size.
“7,” Tim mumbled.
Clara spun round, holding a pair of chunky black high heels. “These’ll do.”
Seeing he still wore boxers, she shook her head. “Everything, love, that means those grim boxers too. Then we can get you into something far sexier and more fitting for my newest girly toy.”
She smiled at Tim and pointed at his crotch. “Off with ‘em.”
Tim swallowed, slowly slid his boxers down, stepped out, and added them to his pile. Turning, he met Clara’s gaze on his crotch, and he quickly covered himself.
Clara grinned. “Not much to hide, is there?”
Tim blushed and dropped his head.
“Oh, how cute, my little girl’s shy about her tiny clitty,” Clara laughed.
“Now, you can cover it.” She picked up a pair of silky black knickers and held them out.
Tim reached for them, feeling the cool, soft fabric, like Ellen’s thongs. The front was black silk, the back stretchy lace that would show his bum through the pattern.
“Don’t just gawp, put ‘em on,” Clara urged.
Tim nodded, lowered the knickers to his ankles, and stepped in.
As he pulled them up his legs, the fabric brushed his skin in a way he always found arousing, from Lucy’s knickers to his own.
Adjusting them around his slightly stiffening penis, Clara sighed.
“Very pretty, lucky you’re blond so your body hair’s near invisible. You should shave everywhere next time, though.”
Tim looked at her, puzzled.
Clara caught his look and smiled, a bit menacingly to Tim.
“Oh, I promise, after tonight, you’ll be changed forever and back as often as I need you.”
Like a switch flipped, Clara’s face lit up with a grin. “Stockings next, sit on the bed, roll ‘em into a ball, then up your legs – you know the drill.”
Clara handed Tim two red hold-up stockings. He sat on the bed and followed her instructions, rolling the familiar silky-smooth material over each leg, as he’d done with Ellen’s.
After smoothing the stockings, a ritual he’d always savoured alone, Clara walked round the bed and stood before him.
“Arms behind your back, please.”
Tim obeyed, and she sprayed his chest with a can. Tossing it on the bed, she grabbed a small box from behind him, pulled out a flesh-coloured plastic mass, and pressed it firmly to his chest.
“Hold it there with your left hand, Tim,” she said.
As Tim did, she repeated it on the other side, telling him to hold it with his right.
She stepped out of sight, and Tim sat holding what he realised were breast prosthetics – something he’d planned to buy but never had, stuffing his bras with rolled socks instead.
After a moment, Clara told him to let go, and Tim felt the weight of the breasts tugging his chest, the adhesive holding them fast.
Reappearing, Clara told him to stretch his arms forward, and she slid a black bra over them, leaning close to fasten it at his back. Tim caught her heavy floral perfume, closed his eyes, and sighed, hearing Clara giggle.
“You love this, don’t you?” she whispered, and Tim couldn’t help whispering “Yeah,” like he had in Ellen’s corset.
Clara stepped back, eyeing him up and down.
“Not a bad start, lucky you’ve got a slightly girly figure and face. I’d put you in a corset, but we’ll skip that tonight – maybe next time.”
She motioned him to stand.
“Next, make-up, and plenty of it for your debut.”
Clara led him to a dressing table, sitting him on a stool facing away from the mirror so he couldn’t see himself in the wardrobe doors without turning. All he could focus on was a pink silk dressing gown with red and white flowers hanging on the door, which he found cute and wished he could buy.
Snapped out of his daydream, Clara said: “No peeking in the mirrors till I say, got it?”
Tim nodded, unable to speak, and sat quietly as Clara opened jars and applied make-up. He closed his eyes when told, letting her dab on eyeshadow, blinked at the false lashes glued to his lids, and flinched as she tweezed stray eyebrow hairs. Tim worried that might go too far, but he couldn’t muster the courage to challenge Clara – she was too intimidating for him to be anything but passive.
Clara left Tim on the stool to let his second coat of lip gloss dry, then returned from the wardrobes with a chestnut-brown wig, long and wavy. She set it carefully on his head, grabbed a small bottle from the table, unscrewed it, and used the pipette to dab adhesive along his scalp under the wig’s edge.
“Don’t want your hair falling off at the wrong moment, do we?”
Tim glanced at Clara but didn’t reply – he didn’t think she expected one.
“Stand up, and remember, no squinting, look straight ahead.”
Tim stood, staring at the flowery dressing gown.
He felt Clara hold something to his waist, and looking down, saw her fitting a skimpy red bustier around him. She tugged it tight, making Tim suck in his stomach. As she fastened the hooks at his back, he struggled to exhale fully. Looking down, he saw it barely covered his bra, the prosthetics clearly visible.
Next, Clara told him to lift his feet, and he stepped into a black leather mini skirt she pulled up his legs and over his hips. It was tiny, just 30 cm long, barely covering his crotch – Tim knew bending over would hide nothing.
Clara stepped in front of him and smiled.
“Hold out your left hand.”
Tim obeyed, and she fastened a black leather bracelet with “Slut” in rhinestones around his wrist. Then, from her dressing gown pocket, she pulled a necklace. Tim saw “Slut” in the centre of silver links, flanked by links shaped like erect penises.
Clara draped it round his neck, fastening it. Tim felt it sit snug against his skin.
Clara smiled, scanning Tim head to toe. “You need one more thing to be perfect – a name, a proper slutty one.”
She tapped her lip, thinking. “We can’t call you Tim, that’s not slutty or girly enough.”
“I reckon Carrie suits you, yeah, you’re Carrie,” spelling it out: “C A R R I E.”
“Turn round, Carrie, check yourself in the mirrors.”
Tim was shocked by the renaming. He’d always been Mia when dressed, like at the Platt Fields party, but Mia was tame. He’d never gone this risqué, and Carrie fit this version better.
Turning, Tim saw a woman beside a smiling Clara across the room. She looked like a total tart: eyes framed by dark black shadow and long lashes caked in mascara, lips glossy red, clothes revealing more than they hid. The red bustier pushed up obviously fake breasts, screaming she wasn’t a real woman. Tim blinked his make-up-crusted lids, looked again, and recognised himself, dressed like a slag.
Clara ran a hand over Tim’s shoulder. “Well, Carrie, what d’you think? Like what you see?”
Tim swallowed, starting to say “Erm…” but was cut off as Clara’s hand reached his crotch.
“Reckon you do, judging by this.”
Tim hadn’t noticed, but his stiff, throbbing penis strained against the silk knickers, and he moaned as Clara squeezed.
“Maybe we should sort that out. Want me to play with your clitty, Carrie?”
Tim moaned again as she rubbed his aching cock.
Clara leaned closer, nudging Tim back to the bed and pushing him down so he fell onto it.
Tim lay there, gazing up at the gorgeous woman looming over him.
“Wait here a sec, Carrie,” she said, vanishing from view.
“Now, lift your arms above your head and keep your wrists close.”
Tim did as told, feeling metal click around one wrist, then the other. Clara pulled him higher on the bed, Tim wiggling his bum as he slid, the satin knickers rubbing his hard cock, making him moan softly. He noticed Clara was stronger than she looked.
Another click, and Clara reappeared.
“There, now your hands can’t wander, even if you’re tempted.” Tim tried pulling his arms down, but he was securely handcuffed to the headboard.
Clara told him to lift his head and shoulders, sliding a pillow under him so he wasn’t flat.
Then she moved down the bed, lifted Tim’s skirt, pulled his knickers down his legs, leaving one leg free but the other dangling from a shoe.
“Proper slutty look,” Clara remarked.
His penis, freed from the knickers, sprang upright, and Clara gave a small, mocking snort, then pulled a condom from her robe pocket, tore it open, and rolled it over his erection.
She gave it a gentle stroke, and Tim shivered.
What happened next shocked Tim. From out of sight, she produced a large black dildo, at least 20 cm long, with a glossy head gleaming in the room’s light. She held it before him.
“Like what you see, Carrie? Isn’t it gorgeous?”
Tim was speechless. This went beyond anything he’d done, even the party with his mates, and felt more like porn he’d watched online.
Clara smiled. “I want you to kiss it for me.”
She held the tip near his mouth, the long black shaft filling his view.
Tim didn’t want to and couldn’t speak, shaking his head.
“I promise, Carrie, you’ll love it.” As she spoke, she stroked his penis, making Tim moan, then moved the tip closer, brushing his lips.
“Kiss it for me, Carrie, I know you really want to.”
Tim shook his head again.
Clara’s hand slid down his shaft to his balls, then squeezed. Tim squeaked in sudden pain. “Just a little kiss, Carrie,” she said angrily, “and I’ll keep playing with your clitty, I know you’d rather that.” She squeezed his balls again, lighter, but the threat was clear.
Tim groaned as the pain eased. He wanted Clara to keep stroking his cock, not hurt him again, and knew there was only one way to make her stick to the pleasant option.
Relenting, Tim puckered his lips, leaned forward, and gave the tip a tiny kiss.
“That was a pathetic kiss,” Clara scoffed. “Kiss it properly, Carrie.”
Tim sighed and gave what he thought was a proper kiss.
He was rewarded as Clara’s hand returned to his penis, stroking gently, saying:
“Good girl, now lick it, Carrie.”
Tim knew he could hardly refuse after the kiss, so he stuck out his tongue and licked the tip.
“Good girl, again.”
Tim licked again.
“Keep licking, Carrie.”
As Tim licked, Clara stroked his cock, moving the dildo so he licked not just the tip but the shaft.
Then, as he opened his mouth to lick along the shaft, Clara swiftly pushed the dildo deep inside. Tim coughed, trying to push it out with his tongue, but Clara held it firm, saliva dribbling down his chin. She eased it deeper, then slowly pulled it out, dragging the shaft over Tim’s glossy lips.
“Good girl,” she laughed. “Knew you’d love sucking a cock.” Tim gagged as she pushed it deep again, swallowing what felt like litres of spit.
As her hand quickened on his penis, Tim moaned, muffled by the dildo sliding in and out.
Suddenly, Clara let go of his cock and pulled the dildo from his mouth. Tim lay panting, his penis twitching, close to climax.
Clara leaned close, as if to kiss him, but at the last moment yanked the pillow from under his head.
He felt his lower body lift, the pillow shoved under his bum, propping him up. Clara spread his legs wide, and Tim felt something press against his anus. The pressure grew, and he gasped as the spit-slick dildo slid in. A brief burn gave way to fullness as more of the thick plastic entered him. At first strange, the sensation grew pleasurable as Clara slowly pulled it out, leaving the tip inside, then pushed it back. Tim couldn’t help a soft moan.
As if it were her cue, Clara thrust the dildo faster and harder, each stroke seeming deeper.
Despite his shock, Tim couldn’t stifle his moans as the dildo massaged his prostate, and he instinctively moved his body to her rhythm.
“You love this, don’t you, Carrie?” Clara asked, thrusting deep and pulling back.
Tim moaned “Yeah” as she sped up.
“Tell me how much you want it, Carrie.”
Tim couldn’t hold back; so aroused, he pushed his body down as Clara thrust. “I want it so bad, Clara.”
Clara pulled the dildo out fully. “Beg, Carrie, beg me to fuck you with this dildo, tell me how much you want it, how much you want a cock.”
Tim didn’t want her to stop.
“Please, fuck me, please, I want your cock so bad, it hurts, please.”
Tim groaned in frustration as Clara teased the tip against his anus without entering.
“Not bad, Carrie, but I’m not sure I believe you. Tell me how much you want this cock, what’d you do for it?”
Tim looked down at Clara, positioned between his spread legs, and begged. More than anything, he wanted the dildo back inside, and with wide eyes fixed on her, he moaned: “Please, I want it in me so bad, I’ll do anything you want, please, I need it, I need this cock in me.”
“Anything, eh? Would you suck a real cock for me, let a real man fuck you?”
Tim didn’t think, just answered: “Yeah, yeah, anything, please, anything.”
Clara gave him a crooked smile. “Tell me, convince me you want a real man.”
Something broke in Tim, and he said things he’d never dreamed: “Please, I want to suck a real cock, get fucked by a real man, please, I want it so bad, please.”
“Say it again, that you want to suck a real man.”
Tim moaned: “Yeah, I want to; I want to suck a real cock.”
“And swallow his juicy cum?”
Tim nodded. “Yeah, yeah, and swallow his juicy cum.”
Clara smiled. “Knew you’d be a good girl, Carrie, and good girls always get their reward.”
She slid the dildo fully into Tim. “Keep begging, Carrie.”
“Oh please, Clara, fuck me with your cock, fuck me.”
Clara thrust with one hand, grabbing his straining penis with the other, stroking slowly, then faster, until Tim’s hips bucked under her grip.
“Tell me what you’d do with a real man’s cock, Carrie.”
Between moans, Tim told Clara he’d suck it, lick it everywhere, kiss the tip.
“Carrie, would you take his cum in your mouth, swish it round, then gulp it down?”
Tim moaned: “Yeah, yeah, I would.”
With a final thrust, Tim’s climax hit, his cock pulsing, filling the condom.
Tim’s head fell back, staring at the ceiling.
Clara released the dildo, leaving it inside, and murmured: “Good girl, Carrie, good girl.”
She pinched the condom’s tip, easing it off with enough slack to squeeze the cum-filled end, then removed it fully.
Tim felt the bed dip beside him, and Clara loomed into view.
“Good girls get rewards,” she said, holding the full condom above his face.
Tim’s eyes widened, shocked at what was expected.
Clara raised the condom, holding the open end over his mouth.
“Open wide, Carrie.”
Tim watched the cum slide down in slow motion, and for some reason, opened his mouth, sticking out his tongue.
“Oh, good girl,” Clara cooed at his initiative.
Tim flushed under the thick make-up at her praise and tasted the salty fluid as it hit his tongue’s tip.
It ran down his tongue into his mouth, and Clara squeezed every drop from the condom.
The taste of the slightly warm cum wasn’t great but not awful, and Tim let it slide down his throat.
Closing his mouth, Clara crumpled the condom and wiped a finger over his lips, licking it.
“Mmm, tastes good, yeah?”
Tim just nodded.
Clara stood, looking down at Tim. “Stay there, Carrie, back in a bit.”
Tim heard the door open and shut, leaving him alone, still cuffed.
The Blackmail
Tim lay on the bed, licking the last traces of cum – his cum – that Clara had forced into his mouth from the condom he’d filled while she fucked him with the dildo. He’d been there for what felt like half an hour, growing uncomfortable. The handcuffs dug into his wrists, his shoulders ached, and his lower back complained about his bum propped on the pillow. The dildo still sat in his arse, so he wiggled till the pillow slid out. This shifted the dildo, sending pleasure waves through him. Tim moaned, then louder as it pressed deeper against the mattress. His limp cock stirred, and he couldn’t resist grinding his bum against the bed to prolong the sensation.
Before he could get going, the door opened, and a smiling Clara reappeared.
“Hey, Carrie, sorry it took so long, had a few things to sort.”
Tim felt a sudden emptiness as the dildo was pulled out. He groaned in frustration, and Clara loomed over him, unlocking the cuffs so he could sit up and face her. She now wore a short black skirt, thigh-high boots, and a white blouse peeking under a half-open black leather jacket.
“Put your knickers on, Carrie,” Clara ordered. “I know you’re a slag, but even slags have some standards.”
Tim slid off the bed, bent to pull up his knickers, smoothed his skirt, and looked at Clara, who grinned oddly.
“I’ve got something to show you.”
She held up a tablet displaying an image of the room, with Tim on the bed and a big white play button over it.
“Press play, Carrie.”
With dread, Tim tapped the arrow.
The video showed edited highlights of his transformation, then him writhing on the bed, close-ups of him sucking the dildo, getting fucked by it, and begging for a real cock. When it ended, Tim scanned the room frantically but couldn’t spot the cameras.
He sank onto the bed, shocked and betrayed, tears welling. “What, what d’you want, money?” he asked.
Clara laughed. “Yeah, but not how you think, Carrie.”
“What then?”
“I want you to work for me, Carrie. I’m taking you out tonight, you can do what you begged for, and earn me some cash.”
Tim gaped at Clara.
She waved the tablet. “Goes without saying, if you don’t play ball, everyone you know sees this video.”
Tim trembled, terrified of what was happening and what could happen if he didn’t obey.
“Carrie?”
Tim looked up at Clara standing before him.
“I know you want this, why deny it?”
“I… I… I don’t, I’m not, I can’t.”
Clara slapped him. “For fuck’s sake, Carrie, pull yourself together, you know you really want this. I’m just opening the door so you can actually do it.”
Tim held his cheek, staring at Clara as she stood. He wondered if she was doing this out of some twisted altruism, genuinely trying to help. He sat, grappling with being blackmailed but maybe also helped by this woman.
“Get up, Carrie,” Clara snapped, yanking him from his thoughts.
Tim stood, still clutching his cheek.
“Listen up.”
“You charge twenty quid for a handjob, thirty for oral, thirty-five for oral without a condom, fifty for anal.”
Tim swallowed, certain he’d never, ever let anyone fuck him, even if Clara had just done so with her dildo.
“I want you to earn at least two-fifty for me by the end of the night, or else…”
“I can’t, I could never,” Tim began.
“Shut it, you’ll do what I say, or everyone’ll know you’re a cock-worshipping, crossdressing whore,” Clara shouted.
Tim flinched at her harsh tone, dropping his head, the long chestnut wig falling around his make-up-caked face.
“Now come on, Carrie, time’s ticking.”
Clara stormed out, and Tim, seemingly unable to muster the will to resist, followed meekly.
Onto the Street
Tim shuffled down the stairs, clinging to the banister as his feet wobbled in the highest heels he’d ever worn.
Reaching the ground floor, he looked up from his feet to see Clara at the front door, waiting.
A thin smile played on her lips. “Don’t worry, you’ll get the hang of those heels soon; you’ll have plenty of practice tonight.”
Tim approached, each cautious step sending a tingle as his nylon-clad thighs brushed together.
As he reached her, Clara handed him a small clutch bag.
“Here, stuff you’ll need: condoms, lube, wet wipes, and some lippie.”
Tim took the bag silently. Clara turned, opened the door, and stepped out.
Standing in the doorway, Tim wasn’t just scared of being outside dressed as a woman but also of the slim chance his mates were still nearby. Frozen, Clara turned, went “Tch, tch”, grabbed his bustier, and yanked him forward. Tim stumbled out of the house.
Clara kept pulling till he was well clear of the door, then slipped past to lock it.
Tim glanced around nervously. The dark street was empty, but that didn’t ease his fear of being seen.
As he looked, Clara brushed past.
“Come on, Carrie, it’s not far.”
Clara strode down the path, and Tim, glancing back at the locked door, had no choice but to follow her onto the street.
The cool night air swept over Tim’s body, reminding him how skimpily dressed he was. It wasn’t freezing, about 10°C, but his exposed skin prickled. He glanced enviously at Clara, sure her leather jacket kept her warmer than his outfit did him.
As he eyed her, Clara crossed the street. Tim followed. They walked through a few dimly lit streets, most houses dark, though a couple were brightly lit. Tim hunched his shoulders and lowered his face as they passed, just in case anyone was watching.
Passing a large, well-lit house on Whitworth Street, Clara hissed at him.
“Stop that, Carrie, if you want people to stare and wonder, that’s the way to do it. Stand tall, act confident, no one’ll give you a second glance, act like you belong.”
Tim straightened and kept walking, but it didn’t calm his nerves; he still feared being recognised, by who, he couldn’t say, but the fear lingered.
They reached the corner of Deansgate, a long, well-lit street where a few cars cruised despite the late hour. No other people were about.
“Well, Carrie, here’s your patch for the night, time to earn me some cash.”
Tim felt trapped, half-hoping Clara was just winding him up and would reveal it was a joke. But no, she was dead serious.
A spark of defiance flared, and he shook his head. “I can’t do this, I’m not a prossie, I’m a bloke.”
Clara glared and hissed: “Carrie, you don’t look or act like one, do you?” She stepped closer. “You’ll be what I say, do what I say, you promised to do anything I want.” She grabbed his chin, jerking his face up to meet her eyes. “Got it?”
Tim blinked, trying to avoid her gaze. He understood, but felt torn. He didn’t want to be out here dressed like this, but part of him couldn’t deny enjoying everything that had happened.
Clara leaned closer, hissing: “Remember, Carrie, I’ve got your clothes, phone, wallet, keys, all with me. I know your old name, your mates, where you live. Unless you want them seeing you dressed as a whore begging me for a real cock, you’ll do this tonight and every other night I need you.”
“Clear now, Carrie?”
Tim nodded as the reality hit – he was completely under Clara’s control unless he wanted the world to know about his crossdressing and tonight’s events.
“Answer me, Carrie.”
Tim nodded. “Yeah, Clara, I get it.”
“Good girl, Carrie, now go earn me some money,” she waved up the street.
“Go to the end and back, keep doing it till someone stops.”
Tim looked up the street, then back at Clara.
“Go!” she snapped.
The First Night
Tim hurried away from Clara, his heels clacking on the pavement. The cool street made him shiver, the breeze slipping under his short skirt. Trembling, he wrapped his arms around himself below his fake breasts and kept walking.
The First Client
Carrie stood shivering on Deansgate’s kerb, the bright city centre buzzing despite the late hour. Her 10-cm heels made every step wobbly. Clara loitered a bit away, smoking and watching.
A car pulled up, a bloke in his forties with greying hair eyed Carrie. “So, Carrie, what’s fifty quid get me?” he asked in a Manc accent.
Carrie swallowed: “Twenty for a handjob, thirty for oral, thirty-five for oral without a condom, fifty for anal.”
The bloke grinned, handed her a fifty-quid note, and told her to hop in. He drove to a backstreet in Ancoats, parking under a busted streetlight. Carrie pulled a condom from her clutch and did the job mechanically. Ten minutes later, he gave her a ten-quid tip, dropped her off, and drove away.
Carrie returned and handed Clara the sixty quid. “Good, Carrie. One-ninety to go,” Clara said.
The Next Clients
Carrie paced the street, freezing in her skimpy outfit. After twenty minutes, a black BMW stopped. The driver, early thirties, wanted oral for thirty quid. In a car park near Piccadilly, Carrie got it over with. He paid, no tip.
Around midnight, an older bloke in a van asked for a handjob for twenty quid. In Chorlton, Carrie did it and got twenty-five. Just after one, a nervous student wanted oral without a condom for thirty-five quid. Carrie hesitated but went through with it.
The Last Client of the Night
At two, a silver Mercedes pulled up. The businessman in his fifties wanted “everything” for fifty quid. They drove to a car park near Old Trafford. The act hurt, but Carrie endured, getting a twenty-quid tip.
Carrie handed Clara the last seventy quid. She’d earned 223 pounds (60 + 30 + 25 + 35 + 70) from five clients but missed the 250 target.
The Reckoning
Clara counted the cash. “Twenty-three short, Carrie. Not good.”
Carrie trembled, tears in her eyes. “I tried, Clara, please…”
Clara sighed. “Alright, I’ll let it slide this time. But you’re back tomorrow night, got it? And you’ll make up the twenty-seven, plus another two-fifty.”
Carrie nodded silently. Clara headed back to her place on Oxford Road. “Come on, Carrie. Change and grab your stuff. But remember – I’ve got the video.”
The Second Day and Night
Preparation
The next morning, Tim woke in his Chorlton flat, body aching. Memories of the clients and Clara’s threat haunted him. At 6 p.m., Clara called: “Be at mine by 8, Carrie.”
Tim went to Oxford Road. Clara opened the door in a red dress. On the bed lay a new outfit: a sheer lace bodysuit, a pink mini skirt (28 cm), black fishnet stockings, silver 12-cm stilettos, and a blonde wig. A necklace with “Carrie” in glitter letters sat beside it.
“Get changed,” Clara ordered. “Shave everywhere.” Tim used a razor in the bathroom. Clara did his make-up: dark eyeliner, pink lipstick, thick mascara. “Tonight, you make 277 quid.”
The Second Night
By 9 p.m., Carrie was on Deansgate, the pink skirt barely covering her bum. The 12-cm heels forced tiny steps.
Clients One and Two
After fifteen minutes, an Audi stopped. The young bloke wanted a handjob for twenty quid, gave a five-quid tip. Soon after, a cabbie asked for oral for thirty quid, no tip.
Clients Three to Five
At 11 p.m., a student wanted oral without a condom for thirty-five quid. Around midnight, a bloke asked for a handjob for twenty quid. An hour later, a businessman wanted anal for fifty quid, tipping ten.
Reckoning for the Second Night
By 2 a.m., Carrie had earned 170 pounds (25 + 30 + 35 + 20 + 60) from five clients. Clara frowned. “One-oh-nine short. Tomorrow, you make 359.”
The Third Day and Night
Preparation
Tim was numb, barely sleeping. At 6 p.m., Clara called: “8 p.m., Oxford Road.” The outfit: a silver sequin top, black latex skirt (25 cm), glittery stockings, 11-cm platform pumps, black wig. A “Whore” bracelet in rhinestones lay beside it. Clara did dramatic make-up: smoky eyes, red lips, false lashes.
“Three-fifty-nine tonight, at least seven clients, pricier services,” Clara said.
The Third Night
By 9 p.m., Carrie was on Deansgate, the sequin top sparkling. The latex skirt clung to her skin.
Clients One to Eight
A Porsche driver wanted oral without a condom (35 quid), an older bloke a handjob (20 quid), a tourist oral (30 quid). At midnight, a bloke wanted anal (60 quid with tip). Then a handjob (20 quid), oral without a condom (35 quid), anal (55 quid), and oral (30 quid).
Final Reckoning
By 3 a.m., Carrie had earned 285 pounds from eight clients. She’d made 678 pounds total (223 + 170 + 285). Clara nodded, pleased. “Good, Carrie. We’ll see about tomorrow.”
The Fourth Day and Night
New Rules and the Flat
On the fourth day, Tim was emotionally drained. At 5 p.m., Clara called: “Tonight, you work in a flat, not the street. 8 p.m., Whitworth Street.”
Tim went to Whitworth Street. The flat was plush: dark wood floors, red leather sofa, a big bed with black satin sheets, a bathroom with a jacuzzi, and a separate room with cuffs, whips, and toys. Clara, in a black latex catsuit, explained: “Clients come here. You offer everything: oral, anal, BDSM, roleplay. Prices: handjob 30 quid, oral 40, oral without 50, anal 70, BDSM or roleplay 100. Target: 500 quid a night.”
The outfit: a red corset cinching his waist to 65 cm, black lace knickers, hold-ups, red 13-cm stilettos, a curly red wig. Accessories: handcuff bracelet, “Slut” necklace. Clara did his make-up: gold eyeshadow, red lipstick, false lashes.
The Fourth Night
Work started at 9 p.m. Clara stayed in the lounge, monitoring clients.
Client One
A businessman wanted oral without a condom for 50 quid. Carrie knelt on the bed, finishing quickly. He paid on time.
Client Two
A bloke in his forties wanted anal for 70 quid. In the bedroom, it hurt as Carrie used too little lube. He grumbled but paid.
Client Three
A younger bloke wanted a BDSM roleplay for 100 quid. Carrie had to tie him up and whip him lightly. Unsure, she managed, and he tipped 20 quid.
Client Four
An older bloke wanted anal and oral for 110 quid. It was exhausting, and Carrie fought fatigue. He paid, no tip.
Client Five (Things Go Wrong)
Around midnight, an aggressive client wanted hard BDSM for 100 quid, with Carrie bound. He got too rough, ignoring the safeword (“Red”). Carrie panicked, screamed. Clara stormed in, stopped him, and threw him out. Carrie shook, with bruises on her wrists. Clara gave her water but said coldly: “Pull yourself together, Carrie. Keep going.”
Reckoning for the Fourth Night
By 3 a.m., Carrie had earned 450 pounds (50 + 70 + 120 + 110 + 100) from five clients, 50 short of the target. Clara was annoyed: “You failed, Carrie. Tomorrow, you make 550 to catch up.”
The Fifth Day and Night
Preparation
Tim was broken, bruises throbbing. At 6 p.m., Clara called: “8 p.m., Whitworth Street.” The outfit: a black latex dress (40 cm), like a second skin, black suspenders, fishnet stockings, 14-cm platform boots, black wig with bangs. Accessories: “Bitch” collar, silver earrings. Clara did his make-up: dark smoky eyes, black lipstick.
“Five-fifty, Carrie. No excuses,” Clara said.
The Fifth Night
Work began at 9 p.m. Carrie was tense after the incident.
Clients One and Two
A bloke wanted oral for 40 quid, another anal for 70 quid. Both were routine, but Carrie felt hollow.
Client Three
A couple wanted a roleplay for 100 quid, with Carrie as the “submissive”. They were kind, but the humiliation cut deep. They tipped 20 quid.
Client Four (It Goes Wrong)
A bloke wanted BDSM for 100 quid, with Carrie dominating. Too nervous, she whipped too lightly. He got angry, called her “useless”, and paid only 50 quid. Clara was livid: “You’re ruining my business, Carrie!”
Clients Five and Six
A bloke wanted anal for 70 quid, another oral without a condom for 50 quid. Carrie did both mechanically, getting 10 quid tips each.
Reckoning for the Fifth Night
By 3:30 a.m., Carrie had earned 460 pounds (40 + 70 + 120 + 50 + 80 + 60) from six clients, 90 short. Clara was visibly pissed: “You’re letting me down, Carrie. Tomorrow, you make 640, or the video goes to your mates.”
Clara’s Satisfaction and Carrie’s State
Clara’s unhappy with Carrie. Though she earned 1,363 pounds (223 + 170 + 285 + 450 + 460) over five nights, she missed the higher targets lately. Clara sees Carrie as an investment not paying off enough and ramps up the pressure, still threatening with the video, keeping Carrie in a mix of fear, resignation, and odd acceptance of her role.
Carrie’s physically and emotionally spent. The flat’s nights were intense, the BDSM and roleplays overwhelming. The aggressive client and angry punter deepened her fear. Yet part of her – Carrie – finds a twisted thrill in the control and humiliation, tearing her apart, especially after years as “Mia”, where she tasted desire without consequences. She doesn’t know how long she can endure, but the video’s threat leaves her no choice.
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