SIMON BECOMES SIMONE

Simon woke to the sound of birds outside his bedroom window. He rubbed his brown eyes and stretched before slipping his 5’9″ lithe body out of bed. It was a Monday morning, but instead of taking a shower to begin the working week, he took one to begin a week of dressing up.

Simon was twenty-years old. He lived at home with his single mother and worked in retail. An effeminate young man, he secretly cross dressed in women’s clothing. It started so long ago he couldn’t remember the first time he tried on his mother’s clothes.

Since he started working, however, he bought his own clothes, shoes, make-up and accessories. He slept in sexy satin lingerie, and whenever his mother went away for business or leisure, he would seize the opportunity to dress fully as a sissy-slut, calling himself Simone.

His mother knew her son was gay, or at least bi-sexual. Although she’d never caught him dressed up or seen him with other men, she knew. Simon lost his virginity to a girl at eighteen, then his other virginity to an older man he met on the internet.

Never feeling ready to come out about his sexuality or crossdressing, the internet was where he satisfied his sexual needs and desires, along with the men he arranged to meet in hotels and car parks, after dark.

Following his shower, Simon donned a long blonde wig and an E cup breast plate before slipping on a sexy pink satin babydoll for breakfast. His mother was working away for the entire week, returning home sometime on Saturday.

After breakfast, he sat and watched a couple of episodes of Desperate Housewives, painting his toenails red and glueing a set of red, French false nails to the tips of his fingers. It was then back to his bedroom to properly transform himself into Simone for the week.

Three hours later, in time for her zero carbs lunch, Simone stepped out of her bedroom in a pair of red stiletto platforms, dressed as a busty French maid. A blonde wig on her head and convincing make-up all over her face.

Walking down the wooden stairs in the black and white outfit, loving the sound her heels made with each step, her sissy-clit was in chastity and a thick butt plug occupied her sissy-bottom.

Simone thought it best to do all the house chores in one day, freeing her up for the rest of the week to enjoy her other activities. She had a yoga outfit which clung to her breast plate when she worked out in front of the TV. She had club wear, office attire and so much more.

Simon barely had any clothes; he was a simple boy who needed very little and wanted for even less. Meanwhile, Simone wanted it all. She needed to wear lace, silk and satin on her slim, hairless body. She needed to feel it against her smooth, soft skin.

The week was a dream for the blonde sissy-slut. She was in sissy-heaven the entire time. Under self lock and key, Simone binged on Desperate Housewives and sissy-porn, eventually retiring to her bedroom each night to talk to other sissies, and men who loved to fuck gurls like her, often behind their wives’ backs.

Come Friday evening, her last night of sissy-freedom, before turning back into a boy, it was time for Simone to bring things to an unwanted end and release four days worth of built up creamy cummies.

Wearing a lipstick red, wet-look, strapless bodycon dress and matching fuck-me high heels, she stuck a 6″ rubber suction dildo to the floor, in front of her mirror, and lubed it up.

She then picked up the red masquerade mask from her desk and put it on over her head, concealing her identity before setting up her phone to record the action.

Simone’s clitty was throbbing inside the metal pussy ring chastity cage, as she slowly pulled the butt plug out of her sissy-bottom and checked herself over in the mirror, straightening her long blonde hair.

She smiled excitedly at her reflection whilst humming along to the Spice Girls blaring out of the speakers connected to her laptop. But as she went to lube her opening… her world came crashing down.

Simone’s bedroom door suddenly and unexpectedly opened, and there, standing in the doorway, was her next-door neighbour.

“Neil!!!!!” she screamed, dropping the lube on the floor. She then turned the music off and stood frozen in fear.

Neil was her widowed, sixty-two-year-old neighbour. Her mother forgot to mention that she’d asked him to keep an eye on the house. He was given a spare key, but he was supposed to only enter if there was a problem and Simon was out.

But the old man had been curiously spying through the windows since Monday. He was watering the plants in his back garden when he thought he saw a French maid in his neighbour’s kitchen, cleaning like it was the most fun thing in the world to do. When he realised it was Simon dressed up, he kept a closer eye on things.

“Relax,” he said quietly, hoping to avoid a panic. He put his hands out low, signalling he meant no harm and ignored the rubber cock sticking up from the floor.

Despite being old compared to Simone, Neil was a six-foot ex-rugby player who still kept in decent shape. He could snap the slim, flexible twenty-year-old in half if he wanted to, and he did want to, but not in the way she was fearing.

“It’s ok. I promise I won’t tell a soul, not even your mother. This is your secret, not mine,” he tried to assure her.

“What are you doing inside my house, Neil?” she muttered anxiously, terrified.

The towering figure walked slowly towards her, sympathetically explaining the arrangement with her mother. As he put the spare key down on the desk, Simone complained about the situation in a soft feminine voice, whilst trying to create distance between them.

“Relax, ok. You and your secret are very safe with me,” he said, putting his hands on her arms, turning her around to face the mirror again.

Simone sharply sucked air into her lungs and held it there. She couldn’t believe the nightmare scenario she found herself in. Fully dressed as a sissy-slut with a rubber cock stuck to her bedroom floor, ready to impale herself on.

“You look and smell amazing,” Neil whispered in her ear, while they stared into the mirror at each other. “I like your mask, too. Very sexy.”

Simone let the breath out and gulped, wishing the floor would open up and swallow her whole. “Please don’t tell anyone,” she feared, close to a mental breakdown.

“I’m a man of my word. I told you I won’t tell anyone, and I meant it. So relax and let’s pretend we don’t know each other, ok?” Neil was very gentle in his approach.

Simone’s legs trembled and her breathing became short and shallow. Her neighbour was looking her up and down through the mirror, smelling her sweet perfume with lust in his eyes.

“Can you do that for me, sweetie?” he whispered again.

“I’ll try,” she muttered, fighting to hold herself together.

“Good girl,” Neil smiled, rubbing her bare shoulders. “Now, what’s your name, sweetie?”

“Si… Si… Simone…” she managed to get out.

“You smell and look amazing, Simone,” Neil said softly. “Do you have a boyfriend?”

“Nnn… no…” she continued to wilt but her sissy-brain was slowly being knocked back into gear. Simon had sucked off and been topped by quite a few men in his time, but Simone had never been touched by a man before.

“I won’t hurt you. I might be a big, old, ogre to a pretty young girl like you, but I’m still a gentleman.” Neil collected the false blonde hair, cascading down her shoulders, and gently moved it back, exposing her supple neck. “Do you like gentleman, Simone?” he breathed.

As his warm breath touched her skin, Simone sighed and quivered. “Yes, I do.”

Neil planted little soft kisses on her neck, bringing her eyes to a close with arousal. He watched her through the mirror, slowly melting. She leaned back against him, and then he traced his fingertips down her arms and across the front of her dress.

“Ohhh, god,” she gasped, feeling a strong pair of hands on her body.

Neil brought his hands up and cupped the bulging silicone breasts. He gave them a squeeze, amazed and delighted at how realistic they were. Simone’s cleavage looked fantastic, he thought, slowly pulling down the front zip to expose her fake tits.

“Mmm, you have lovely breasts, Simone. What size are they?” Neil wondered, tracing the tip of his tongue along her neck to her ear lobe.

Simone was pressing back against him with her clitty throbbing inside her cage. “I’m a 32E,” she breathed proudly.

“Mmm,” he groaned, swirling his thumbs over the rubber nipples as he pushed the breasts together. “Big tits for a such a beautiful, slim girl.”

“Uh!” Simone gasped. While Neil played with her breasts, he moved one hand down her body until it reached the hem of her dress. He sucked on her lobe and slowly inched the outfit up her slender thighs.

“Mmm, you’re so sexy, Simone. Are you a virgin?”

“Ohhh,” she quivered again. No was the true answer, but technically, Simone was a virgin. “Yes, I’ve never done it before.”

“Mmm. What do you think about? What excites you, Simone? What do you desire? Tell me, sweetie.” Neil teased her.

Pulling the dress high enough, enjoying the feel of her smooth skin, he smirked at the revealing of her small cock inside its cage. Cute, he thought, looking at the pussy ring on the front of it.

Simone parted her lips, sighing. Neil watched the tip of her tongue come out and wet her red, moist lips. He would quite like to feel that tongue around his cock, along with those sexy lips giving him a blowjob,” he thought.

“I can’t say it,” she exhaled, keeping her eyes closed. He was her neighbour. It was too close to home.

“I won’t hurt you, Simone. Just whisper the words for me. You never know, I might be able to help you.” Neil sucked seductively on her neck.

Simone emitted a groan of approval. Her heart was racing. Her flat abdomen was contracting. Her clitty was throbbing, even her puckered sissy-bottom was twitching. Her body was alive and excited. This is what she was born to do, she told herself, letting out another groan.

“I think about big strong men using me for their pleasure. Big strong men sticking their big cocks inside me,” she breathed the words and completely melted.

“Mmm, there’s a good sissy. How often do you ride that thing?” Neil asked, finally acknowledging the dildo still stuck to the floor.

Simone opened her eyes, remembering she was wearing a mask. It suddenly gave her strength. She glanced down. “Not enough,” she giggled like a real girl.

Her old neighbour spun her around. Her big tits pressed against his chest. He stared lustily through the mask and into her eyes, then looked hungrily at her lips. Do it she thought.

Neil pressed his mouth against hers then pushed his tongue inside her mouth. He held her tight to his body, kissing a sissy for the first time. He didn’t care. He thought Simone looked and sounded convincing. He needed to fuck her.

“Tell me what you want, Simone,” he gasped, parting from their passionate kiss.

“I want to get fucked,” she sighed, tasting the masculinity on her tongue.

“By whom? Tell me,” he urged her.

“You. I want you to fuck me right here in my bedroom.” Simone almost fell to the ground with nauseous lust.

“Mmm, you naughty little slut!” Neil hissed and spun her around again, bending her over the desk to spank her buttocks.

“Ohhh! Yes, Daddy!” Simone cried out. He pushed the dress right up, exposing the softest butt cheeks he’d ever seen, and gave both sides a firm smack. “Ohh! Daddy!”

“Do you like that, Simone?” he hissed, raining his big hand down on her arse. “You want a daddy to punish you for being a naughty girl?”

“Oh God, yes, daddy!” she screamed, taking a thorough spanking until her cheeks burned bright red.

Neil bent down and picked up the earlier dropped lube from the floor. “Mmm, daddy is going to punish his little girl, don’t you worry about that.”

“Uhhhh… uhhhhh…” Simone closed her eyes and dropped her head. An old man, her neighbour, was greasing her tight hole with a long, fat finger.

“Mmm, nice and tight for daddy,” Neil groaned, pushing his index finger inside until it was knuckle deep. He then slowly and gently worked it in and out, just like he used to do to his wife.

Simone rocked back and forth on the finger, salivating at the mouth when Neil started finger fucking her sissy-bottom harder. Whining like a true sissy-slut in anticipation for bigger, harder and deeper things to come.

“I think it’s time you got down on your knees, Simone.” Neil removed his finger and pulled her up from the desk, manoeuvring her so the dildo was between her legs.

Giggling once more, a little shy and embarrassed, Simone got down on her knees, straddling the sex toy. But instead of guiding it into her body, she reached for Neil’s trousers, unbuckled his belt and unzipped his fly.

He grinned down at the excitement on her face, when she pulled his trousers down and out sprang his big cock. It was bigger than her dildo and very real. Smooth and taut for an old guy, she pulled his trousers down further to expose his heavy balls.

“I hope you like what you see,” he chuckled.

“I love daddy’s big cock,” Simone smiled, wrapping her hand around it. She came closer and cupped his swollen nut-sac, licking her lips in preparation.

“Show your daddy how much you love his cock, sweetie.” Neil put his hand on the back of her head and pulled her face closer. “Ohhhh,” he groaned when her open mouth closed around his bulbous head and began to suck.

Simone grew stronger. Her strength made her more obedient, increasing her sissy-desire to pleasure a real man. Old he may be, she thought, moaning and chocking on his big cock, he was still an alpha male.

She sucked his balls into her mouth while stroking his shaft over her pretty face. She then licked from his balls, along his smooth, taut shaft and ended with his leaking tip at the back of her tight throat.

“Mmm, daddy is impressed,” Neil groaned, holding her head while he fucked her face. When he eventually released her, Simone coughed then smiled, looking up at him. The moment they knew he owned her. “Sit down, Simone. Daddy wants to see his naughty girl taking two big cocks.”

Simone grabbed the lube and applied it to her sissy-bottom and the dildo. She then positioned the thick rubber head to her opening and began to slowly lower herself down on it, gradually easing it into her body.

“Ohhh… ohhh…” she whimpered, all the way down until she was full. Her insides contracted around the toy while her eyes rolled around inside her head.

“That’s my girl. Daddy’s naughty girl,” Neil grinned, rubbing his cock around her mouth.

“Daddy’s sissy-slut,” Simone gasped, gently riding the dildo as she gripped his throbbing cock and gobbled it into her mouth.

“Mmm… yeah… your daddy’s sissy-slut now, aren’t you, Simone?”

“Uh-huh!” she agreed, leaking tiny droplets of sissy-juice through her cage. Her suppressed clitty was swollen inside it, aching as her sissy-bottom gripped the dildo.

Neil held the back of her head again, pushing more of his cock down her throat. Simone gagged and whimpered, grabbing her tits while he slowly fucked her mouth. It was her first time being penetrated at both ends. She loved every second of it.

“Ohhh, fuck! You’re so sexy, Simone,” Neil exhaled with his head tilted back, eyes closed at the ceiling. His young neighbour was a great little cock sucker, taking his meat right down her throat while she rocked her body back and forth on the sex toy.

Getting close to filling her mouth with his cum, Neil pulled out and slapped his cock across her face. “Daddy needs to fuck his sissy-slut now, sweetie. Get on the bed, on your hands and knees.”

Hot and sweaty in the bodycon dress, Simone eased herself off the dildo and giggled her cute little butt over to her bed. She looked over her shoulder, crawling towards the headboard while her neighbour undressed. Mmm, now that’s what I call a daddy, she thought, licking her lips once more.

Neil’s body looked as old as he was. Strong, yes, but he had a pot belly which didn’t compliment his upper body. His skin naturally sagged around his muscles and he was very hairy. Simone knew she was in for a good, hard fucking.

“There’s condoms in the drawer,” she nodded towards her desk.

“Don’t need one, don’t want one. Daddy is breaking his sissy in bareback.” Neil knelt on the bed, spreading Simone’s legs. He looked down at her puckered hole winking at him.

She breathed deeply on all fours, staring down at her bed. Fucking a dildo was one thing, she was in control. But having a man with a big cock in control, dictating how he fucked her, was quite another. Simone had never been taken bareback either.

All the hard cocks she took as Simon were average and sheathed. The brief moment of trepidation was soon replaced with desire and lust once more. As Neil began to squeeze the head of his cock inside her sissy-bottom, she knew he was going to fill her up with warm, creamy sperm for the first time.

“Uhhhhh… that is one tight pussy…” he moaned in pleasure as her tight cavity spasmed around his cock.

“Ohhhh… yes, daddy… put it in me… I want to feel it all…” Simone gritted her teeth and clutched fistfuls of bedding. The sensation was so different to her dildo. So different to the guys who fucked Simon with their smaller cocks. It was amazing. Incredible.

The feelings were reciprocated. Neil never managed to fuck his wife up the arse. She was too tight. Too tense and nervous. But Simone was a sissy-slut. His sissy-slut now. He groaned down at the slim blonde bent over in front of him and held her waist firmly.

“Ohhhh! Ohhhh! Uhhhhh!” Simone screamed, taking every inch. She could feel him deep inside her body, throbbing as it stretched her out.

Neil rested his hanging sac against her dripping clitty while he caught his breath. The metal cage felt cold on his balls compared to the warmth he felt around his cock. He then pulled backwards, keeping only his engorged head inside his sissy before he pushed forwards and exhaled a deep grunt.

“Oh, fuck!” Simone exclaimed.

Neil closed his eyes and pulled hard on her waist while he thrusted in and out of her tight sissy-bottom, faster and faster. His sissy could only scream and gasp for air now. Her breast plate pulled on her back as the weight of the big rubber tits jiggled beneath her.

“Yes! Yes! Uh! Don’t stop, daddy!” He had no intention of stopping until his balls were empty.

The pleasure grew stronger and stronger, in both of them, as Neil repeatedly rammed his cock inside her. The bed was squeaking and knocking, and the bedroom stank of hard sex. The pair were fucking like uninhibited animals.

“Yes! I’m coming, daddy!” Simone cried out, getting fucked like a rag doll. “Don’t stop!”

“Cum for me, slut! Ahhhh! Cum for your daddy!” Neil slammed into her, hard and deep until she exploded in orgasm.

“Oh, yes! Oh, yes! Yes! Oh! Oh! Yes, daddy!” Simone whimpered like a girl as her cummies poured from her throbbing clitty. Through the gaps in the metal cage, they flowed, onto her bed.

“Ohhh, fuck that’s so hot!” Neil groaned, maintaining the pace and power of his strokes.

As his young sissy-slut shuddered helplessly, his balls tightened. He felt a tingling sensation consume his dome-shaped gland and then he grunted, slamming his cock balls deep as his masculine sperm erupted fiercely inside Simone’s sissy-bottom.

“Uhhhhh! Take it, Simone! Take my cum, you naughty girl! Make daddy proud of his little cum-slut!” Neil didn’t recognise himself. All he cared for was the ride he was having. The ride of his life.

“Yes, daddy! Fill me up! Fill your grateful little slut with cum!” Simone could feel him, throbbing and twitching deep inside her. She pushed back, panting, as he finished giving her his thick load.

Snorting, when he finally pulled out, Neil stood up and looked down at the mess he made of her. Simone had fallen down on her bed, also panting, while her stretched hole slowly leaked sperm.

“Well, I wasn’t expecting my weekend to begin like this,” he chuckled. “Are you ok?”

Simone raised her arm and gave him a thumbs up. She was more than ok. He then asked if he should see himself out, unsure how to act, now they were back in reality. Simone simply gave him another thumbs up.

The next day, Simon woke to the sounds of voices talking in the kitchen. Rid of all things Simone, he trudged downstairs in his man pyjamas to find Neil sat at the table, drinking a cup of coffee with his mother.

“Morning, darling,” she beamed. “How was your week of freedom?”

Simon gulped while Neil smirked over the rim of his coffee cup. “Uneventful,” he muttered. “How was your week?”

“It was work,” she laughed. “Neil was just telling me about his new girlfriend.”

“Yeah?” Simon looked at their neighbour, wondering what the fuck?

“Well, it’s early days and she is a lot younger than me. But she’s great.”

“Ahh, that’s nice,” Simon’s mother smiled. “Maybe I’ll get to meet her one day.”

“Like I said, it’s early days. I’m hoping to see her again soon.” Neil glanced up at Simon. “I don’t want to scare her off, she’s a sweetie.”

Simon rudely left the kitchen and returned to his bedroom. He was in turmoil for weeks, until his mother went away for a spa weekend with her sister.

The evening of the day she left, Simone was dressed as a naughty schoolgirl, sat on the end of her bed, deep throating her daddy while she fondled his balls.

“Mmm, if you’re going to be my secret sissy-slut, you’re going to need to start getting ready at my house.”

“I’d like that, daddy,” Simone smirked, licking his thick shaft.

“I have a spare room with Simone’s boudoir written all over it,” he groaned, needing her regularly.

“Mmm… when do I move my things in?”

“Right after I’ve finished with you. Now bend over and show daddy that tight sissy-cunt. My balls need emptying.”

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