Cabin 121 Park Motor Lodge, Engadine NSW, Australia
The erect penis that hovered inches above Sarah’s face was uncircumcised. The owner pulled back the foreskin to reveal a purple glans fringed by pearly penile papules. The stench of smegma invaded Sarah’s nostrils and she grimaced. The penis was gnarled with thick blue veins running along the length of the dark-skinned shaft; a runnel of clear pre-ejaculate hung from the eye. The penis was not the worst that Sarah had ever seen but somehow it seemed maleficent. As maleficent as the man to whose body it was attached.
He was straddling Sarah’s chest and the bed groaned under his weight as he shifted to get more comfortable and he pushed his cock closer to her lips. Sarah shuddered and the man laughed evilly.
“That’s right bitch, you better be afraid. I’m going to stick that thing in your mouth and you’re going to suck it. You’re going to suck it just right; just like you’ve sucked a couple hundred other cocks before mine. You bite it and I’ll hit you so hard that I’ll knock your teeth out and then it will slide in and out of your gummy mouth just fine,” the man’s voice was guttural; filled with vehemence and lust.
Sarah nodded her head. It was the only part of her body that she could move because her wrists were handcuffed to the metal-framed bedhead and her feet were being held down by another man to stop her struggling.
“Here we go honey,” the dark-skinned man thrust his penis between Sarah’s lips and she knew better than to do anything other than to open her mouth and begin to suck on the coriaceous phallus.
The man raping her mouth was right. Sarah had lost count of how many cocks she had willingly sucked over the years and this was far from the worst. She filled her mouth with saliva and used it to wash away the cheesy smegma with her tongue. She swallowed the repulsive amalgam quickly so that the taste didn’t linger and then she went to work. She ran her lipsticked lips up and down the shaft and flittered her tongue along the corona of the glans. Sarah was an expert cocksucker and she intended to use all her skills to try to get this man off quickly.
She wanted the ordeal to be over as expeditiously and painlessly as possible.
She felt the bed move again under the weight of the man sitting astride her calves and the pressure of his erect penis as he began to rub it on her stocking-sheathed legs.
“Fuck that feels good,” the man straddling her calves sighed as his cock slid back and forth along her shapely legs.
Sarah paid no attention to the man fondling her legs. She concentrated on fellating the big black cock that filled her mouth.
Without the use of her hands to hold the offending appendage Sarah had to cope with the man thrusting his cock in and out of her mouth. She had no control over the tempo but she made sure that she tended to the cock to the best of her ability with her lips and tongue. She clamped her lips tightly around the base of the throbbing protuberance when he forced it all the way into her mouth, nearly choking her. She loosened her grip when the man began to withdraw his cock so that her plump lips slid along the shaft ensuring that she bestowed the maximum pleasure to the dorsal nerves, the pleasure centres in the shaft of his penis.
At the same time her tongue flittered and slathered the bulbous head of the invading phallus, working the tip around the corona and flickering the ultra-sensitive fraenulum. She lapped at the secreted precum, grateful for its sweetness to offset the lingering taste of the man’s sebaceous secretions that lingered in her mouth.
“You’re doing just fine honey, now work that tongue and those lips a little harder bitch because I’m just about ready to blow my load. You better swallow all of it too bitch or you’ll be sorry,” the heavy dark-skinned man huffed as he began to fuck Sarah’s mouth harder and faster.
The man straddling her legs had slipped his erect penis between her calves and was fucking them. She could hear his heavy breathing and feel the steely-hard shaft pressing into her flesh, her stockings were becoming damp with his precum but that was the least of Sarah’s worries. With any luck the man would ejaculate all over her stocking-sheathed legs and he would be sated, sparing her from whatever new horror awaited her once the black man blew his load in her mouth.
“You were right about this bitch Loyd. She sucks dick like a world-class cocksucker,” the black man chuckled then he held Sarah’s head in a vice-like grip and began to fuck her mouth earnestly.
Sarah picked up on the name Loyd. Loyd was the name of the man who had lured her to this cabin but there was nothing she could do with the titbit of information now. She continued her ministrations to the big pulsing appendage that was raping her mouth.
The cock in her mouth began to throb and Sarah could sense the muscular contractions that propel semen through the urethra during ejaculation. In other words the man was about to cum. The man was grunting with exertion as he worked his cock in and out of Sarah’s mouth, his scrotum bounced on her jaw, his wiry pubic hair tickling her chin. She closed her lips around the pulsing prong and lashed the bulging plum of his glans with her tongue and then she tasted the first freshet of salty-sweet ejaculate as the man orgasmed.
The man was looking down at Sarah’s pretty face. She wasn’t young by any means but she was attractive: her emerald-green eyes were framed by a fringe of jet-black hair and enhanced with heavy black eyeliner and mascara and smoky-toned eyeshadow. Her cheeks were rouged, her face makeup pale and dramatic. Her lips were coated with ruby-red lipstick and the man watched mesmerised as those sweet lips sucked his bloated manhood, her throat working as she swallowed his issue.
Sarah’s mouth filled with the musky, viscous liquid that spewed out of the eye of the quivering cock that was slithering in and out of her mouth. She clamped her lips around the shaft and milked the disgorging appendage, swallowing the sweet secretions as they erupted in a volatile explosive paroxysm. She almost forgot that she was being mouth-raped by the big black man straddling her chest and that the man she knew as Loyd was dry-humping her legs as she dutifully brought her defiler to an explosive orgasm. She couldn’t help but relish the feel of his cock exploding in her mouth and the taste of his creamy issue as it filled her mouth. Despite her predicament her cock became semi-erect inside her satin panties.
The black man’s cock gave a final shudder and he moaned as his orgasm peaked and then waned. He ripped his cock from Sarah’s mouth and clumsily dismounted and knelt beside the bed. He turned Sarah’s head sideways so that she faced him. He was studied her pretty face, looking at her like she was his prey.
“That was some fine cocksucking, bitch. But my friend Loyd here and his pals need some lovin’ too. We are only just getting started with you baby. Look down at Loyd’s fine hard cock honey. You’ve seen that before haven’t you? Well you’re going to get acquainted with it up close and personal real soon,” the man twisted Sarah’s head viciously so that she was looking down her torso.
She could see the man she knew as Loyd straddling her legs, holding her down on the mattress. He was no longer fucking her calves but his cock stood out proud like prow of warship ready for battle.
Yes, Sarah had indeed seen Loyd’s cock before and it was his cock that was responsible for the trouble she was in now.
Five Days Earlier – Aarows Sauna and Spa – Rydalmere NSW
“One of these days you’re going to regret hooking up with those strangers that you meet online. You’re putting yourself in a vulnerable position with no protection if things go bad,” Cindy said as she concentrated on applying her mascara in the mirror.
Cindy was standing shoulder to shoulder with Sarah, sharing a mirror, as they applied the finishing touches to their makeup. They were both wearing miniskirts, satin blouses, sheer nylons and fuck-me heels. Their hair was big. Cindy’s wig wore a blonde bouffant and Sarah wore her signature shoulder-length black ‘Bettie Page’. Tuesday night was Tranny Night at Aarows and half a dozen crossdressers in various states of transformation competed for space in the cramped changeroom.
Aarows advertised itself as Sydney’s premier health, recreation & social centre where safe sex is permitted regardless of gender. It sprawled over three floors: the ground floor encompassed the changing and locker rooms, a lounge, kiosk, gym area, free pool tables, wet area and outdoor smoking area. The second and third floors comprised cinema rooms, private booths, sling rooms, ‘suckatorium’ glory holes, playrooms and orgy areas, and large relaxation areas. It was a licenced a ‘sex-on-premises’ venue, a safe space, where those so inclined flocked to engage in all forms of debauchery. It was open 24/7 and was a very profitable business.
“Again with the terrifying scenarios! For fuck sake Cindy, I’ve met plenty of guys off the apps and I haven’t met a serial killer yet,” Sarah pursed her lips in the mirror to make sure her lipstick was perfect.
“Yet! You go around to some stranger’s house or flat or to some fleabag hotel and once you are inside who knows what might happen?” Cindy countered, dropping her mascara stick into her purse.
“I’ll tell you what happens. I have great, guilt-free, sex and if we click we meet again. If I don’t like the guy or he doesn’t like me we just part ways and move on,” Sarah countered.
“Still… meeting strangers at those places is risky. I like this place. I get to hookup with my regular admirers twice a week, and sometimes I have sex with guys I haven’t met before, in a clean, safe, well managed environment,” Cindy commented fussing with her makeup bag.
Cindy was in her fifties. Out of drag she was a short balding man named Robert who had the beginnings of a potbelly and worked a boring office job in the city. Robert lived in a sexless marriage, his wife had given up on sex when menopause approached. She knew that Robert had been crossdressing since before adolescence but Robert had purged and remained faithful throughout his marriage until his wife turned frigid. They both agreed that besides the lack of sex, their marriage was a good one and they had raised two adult children, they enjoyed each other’s company and they liked to travel together.
Robert’s wife had agreed to allow him to go out and ‘play’ as Cindy twice a week so long as he was discreet about it. It was a ‘don’t ask – don’t tell’ arrangement that suited them both.
In drag, with a waist-cincher, a good wig and expertly applied makeup Cindy was a little stunner and had a small retinue of men who met up with her at Aarows on Tuesday and Friday nights. She was also partial to bending over or dropping to her knees for men she hadn’t met before if they took her fancy.
“Check this out,” Sarah thrust her mobile phone in Cindy’s face.
“Nice cock,” Cindy commented.
On the screen was the a picture of a slim, toned man who was naked and sporting a large, healthy erection. His face had been blurred which was not unusual for profile pictures on hookup apps.
“His name is Loyd and I’m meeting him at a nice little cabin on Saturday night at Engadine. It’s only a fifteen minute drive from mine so I can go there in full geish. He will never meet Stefan, and as you know, I use a separate phone and laptop for Sarah’s proclivities so Stefan will remain anonymous,” Sarah sounded a little too pompous and self-assured to Cindy.
“So when the coppers find Stefan wondering around The National Park, beaten, robbed and raped and your car nicked, at least you can direct them to a cabin in a cheap motel in Engadine which this Loyd fellow undoubtedly rented under a false name. Of course you will have to explain to them why you are dressed as a woman,” Cindy made her way to her locker and dropped her makeup bag inside and took out the little purse that contained the necessaries she would need for a night at Aarows.
“You’re just jealous,” Sarah dropped her makeup bag in her locker beside Cindy’s and took out her own little purse.
“Did you take your PrEP?” Sarah changed the subject.
“Yep. Did you?” Cindy asked.
“Yep and I’ve booked an appointment for a checkup at the clinic on Thursday so I’ll get a prescription for a top-up,” Sarah replied.
“What time are you leaving tonight? Sarah added.
“I promised Mildred that I’d be home just after midnight. Not that she cares. I have to sleep in the spare room on my play nights,” Cindy checked the contents of her purse.
“Yeah, I’m working tomorrow so I won’t be staying too late. I’ve got a couple of regulars lined up but you never know what the cat will drag in,” Sarah chuckled.
“See you later sweetheart, play safe,” Cindy leaned in and kissed Sarah quickly on the lips and Sarah smacked Cindy on the arse as the diminutive crossdresser toddled off to the playrooms on her high heels.
Cabin 121 Park Motor Lodge, Engadine
Sarah was able to get a good look at the man who had just fucked her mouth as he waddled away. He was a large man but his fat was layered over muscle. His back has covered in tribal tattoos. With his dark deep brown skin tone, coarse textured black curly hair, prominent cheekbones, strong jawline, almond-shaped eyes, full lips and a wide-bridged nose, she guessed he was Polynesian. If she was honest, Sarah would have to admit that he was handsome but for now she filed away his description in case she needed it later.
Loyd climbed off the bed and freed her legs and she grimaced as the circulation returned to them. She wished she could rub the numbness from them but her wrists remained securely handcuffed to the bedhead.
“Don’t start kicking Sarah or I’ll tie your ankles to the bed too. Just behave yourself and you can get though this with no harm done,” Loyd spoke for the first time.
Sarah’s head was resting on two pillows of the cheap motel variety that offered little support and Loyd snatched the other two pillows and began to stuff them under the small of Sarah’s back.
“Let’s make you a little more comfortable for what comes next shall we,” Loyd looked knowingly into Sarah’s eyes.
“You really are quite pretty and I want to watch your face when I fuck you,” Loyd patted her flat belly reassuringly but Sarah felt anything but reassured.
“Look’s like you got a little aroused while you were sucking Salesi’s cock,” Loyd had hiked Sarah’s navy blue knee-length pencil skirt up her thighs, exposing her white satin full-cut panties.
When Sarah and Loyd had been chatting online about their forthcoming rendezvous they had discussed what she would wear. Like most accomplished crossdressers Sarah was proud of her appearance and she had sent him a few cheesecake shots of her wearing different outfits. Sarah was quite pleased when Loyd had told her that he liked the secretary look. It meant that she could drive to the motel dressed enfemme rather than drive there as Stefan and transform. If he’d chosen French maid or ‘naughty nurse’ or some other fetish costume, it would have made driving to the motel dressed enfemme risky, even in the evening. Presenting as a conservative but sexy secretary was low risk if she had to pull over for any reason, say for car trouble or an RBT.
Loyd patted Sarah’s now fully deflated penis through her panties but the telltale wet stain in the translucent white satin was evidence that she had recently become aroused.
“Don’t worry, I won’t tell anyone if you wont,” Loyd chuckled evilly and Sarah heard muffled laughter come from elsewhere in the cabin.
From the corner of her eye she could make out the shape of at least two other men moving around the room. She could hear the muffled sounds of a pornographic movie playing on the television or on an electronic device. It did not bode well.
“Anyway, you know that it was me rubbing my cock on your magnificent legs while you were sucking Salesi’s cock. I love those stockings by the way, so now I’m going to fuck you a little. Don’t fight, don’t bite, don’t scream and then I wont have to get Salesi and the others to hold you down. They’re libel to get a little rough so it’s in your best interest to just take it. It’s not like you aren’t used to being fucked is it?” Loyd leaned in close and Sarah could smell his cologne and mouthwash.
She saw Loyd’s face clearly for the first time. He was not classically handsome but his countenance was compelling: his head was leonine, crowned by a thick black mane, he had a high forehead, a long nose that had been broken and not reset properly, his lips were full and sensual but the most striking quality was his fathomless, deep dark eyes in which she saw no sympathy only lust.
She had shared far too much information with Loyd online, including sending him images of her engaging in sex acts. What she had picked up on was Loyd’s use of the words the others and for what comes next she wondered how many other men were in the cabin and what they intended to do to her. She wished that her imagination wasn’t as vivid as it was.
“There is some controversy about who actually said it, but it’s good advice: ‘when rape is inevitable, just lie back and enjoy it’,” Loyd chuckled as he climbed onto the bed.
Sarah expected that he would rip off her panties, open her legs and begin to defile her and she was mentally prepared for it but Loyd surprised her when he hovered over her, taking his weight on his hands and feet as he gently lowered his body on top of hers. He lovingly stroked her face as he gazed into her emerald green eyes, enhanced by the heavy makeup. They were filled with fear and tears brimmed at the corners.
“You didn’t have to do this to me. We were going to meet for sex anyway,” Sarah whispered, her voice quivering a little.
“But it’s what I like. I like to see you helpless while my friends use you. I like to see the fear and confusion in your eyes. I want to see you capitulate and surrender yourself, knowing there is no alternative,” Loyd whispered in reply and lowered his lips to hers.
Sarah turned her head sideways trying to avoid the kiss but Loyd’s facial caress became an openhanded slap that jarred her cheekbone and rattled her teeth. He forcefully turned her head so that she was looking up at him.
“Don’t mistake my politeness and courtesy for decency. If you aren’t compliant we have ways of making you wish you had behaved better. I’m going to kiss you now and if you bite me I’m going to have Salesi fulfill his promise regarding your dental work. Do you understand?” Loyd smiled down at her but his smile was as cold and calculating as a crocodile’s.
The handcuffs were chafing Sarah’s wrists and her arms were aching from being stretched. Loyd was not a heavy man but his weight was pressing her down into the bed. The circulation had returned to her legs and feet but they ached dully from where Loyd had sat on them to hold her down while Salesi face-fucked her.
Sarah nodded compliantly and prepared herself as best she could for what would come next.
Loyd’s lips were soft and tender as he kissed her closed-mouthed briefly before he slipped his tongue between her lips. Sarah knew better than to bite or keep her mouth locked shut, she let him explore her mouth with his tongue while his full lips pressed against hers. She felt his cock, which had become flaccid during their brief conversation, become engorged and Loyd circled his hips so that it rubbed against her satin panties.
His breath was sweet, almost cloyingly so, and tasted of mouthwash and spearmint chewing gum with an undercurrent of tobacco. He stroked her hair and her face as he kissed her, behaving more like a lover than a rapist. As the passion of his kisses intensified his hands began to move down her body. He unbuttoned her satin blouse and his hands slid into the cups of her brassiere and he removed her silicon breastforms and tossed them aside.
Sarah couldn’t help but gasp as his fingers stroked her hardening nipples. She might have meagre ‘man-boobs’, a product of age rather than obesity, but they were sensitive and circlets of delight radiated from them as Loyd teased her nipples with his thumb and forefinger, moving from one to the other. She gasped into his mouth and she felt Loyd’s lips form a smile as he continued to kiss her. The kiss became more impassioned and his tongue flittered in her mouth, his cock slid back and forth along her panties and, god help her, Sarah felt her own penis begin to distend.
She was sure that Loyd had noticed but he said nothing, instead his hands continued their journey down her body. He untucked the tails of her blouse from the waistband of her skirt and his fingers drifted sensuously across her flat belly, briefly circling her bellybutton before moving on until they rested on her hips. They drifted down her skirt and lingered at the tops of her thighs, where they stroked the dark welts of her fifteen denier fully-fashioned stockings. They lazily explored the silky band of translucent nylon and fiddled with the silver clasps of her garter snaps.
Sarah couldn’t help but become concupiscent. Loyd’s kisses were sensual and demanding, the sensuous journey of his hands as they roamed down her body had ignited her pleasure centres and his ministrations to her thighs were lewdly stimulating but most of all the constant friction of his hard cock pressing on hers through her delicate lustrous panties was overpoweringly erotic. The feel of his steely shaft rubbing against her cock, his bulbous glans pressing against the vascular apex of her penis through the delicate garment was erotically exhilarating.
Loyd’s hands continued their odyssey. His fingers lingered on her stocking-tops for a while and then he began to trace the backseam of her stockings, taking an achingly long eternity before his fingers tickled the fine wrinkles in her nylons behind her knees.
Sarah was experiencing what she could only describe as bliss. Her lovers seldom took their time exploring her body like Loyd was doing now and few had Loyd’s ability to arouse her so tantalisingly. He was undoubtedly a very experienced lover and so far had not hurt her or treated her with the violence that she expected other than the slap. In fact she had to force herself not to intertwine her tongue with his and return his passionate kisses or to lift her legs and wrap them around his sinewy torso or to lewdly grind her pelvis into his so that their cocks meshed together with only the scintilla of diaphanous fabric between them.
But all that changed suddenly.
Loyd shot his hands under Sarah’s legs, slamming the crook of his elbows behind her knees. He swiftly lifted her legs up so high that Sarah could see her ankles and the stiletto heels of her shiny black ‘fuck-me’ pumps. His rigid pole slipped inside the leghole of her panties and he pressed her down into the bed with all his weight and crushed his lips against her mouth as his glans nestled snuggly in her sphincter and then he drove his long, thick cock all the way inside her anus.
Sarah’s scream was muffled by Loyd’s mouth, her body twisted and writhed beneath him, her wrists chafing at the cuffs as she tried to expel the hot iron rod that had invaded her rectum. Her long legs quivered as she tried to kick out but she was unable to use them as Loyd held them tightly, his elbows under her knees and his hands gripping her ankles as he forced all of his engorged manhood inside her tight anus.
Sarah had inserted silicon lubricant beads in her anus before leaving for the rendezvous but the lubricant did little to ease the pain as Loyd’s cock invaded her tight back passage. The pain was a fiery, sharp, intense spasm of agony which caused Sarah to thresh around on the bed despite the cuffs, the weight of Loyd’s body and his grip on her ankles.
Loyd rode with her, ensuring that his cock remained buried in her anus, stifling her screams, riding her like a bucking bronco.
Much to Sarah’s relief and surprise, Loyd didn’t begin to fuck her. He kept his cock buried in her ass but he lay still on top of her while the pain washed over her and slowly began to dissipate. It was not the first time that an inconsiderate lover had slammed his cock all the way inside her without regard for the pain it might cause. But in the past she had been able to expel the offending appendage quickly and teach the errant paramour how to properly mount her.
“There’s a good girl, take the pain. You know it won’t last long,” Loyd whispered in her ear almost soothingly.
Loyd was right and the intense scalding sting slowly began to dissipate. It became a dull throbbing ache that was still painful but manageable. She stopped trying to kick and buck and lay still, letting herself become accustomed to the dull twinge in her rectum. She tried to expel the thick, meaty prong but that only caused her more pain so she concentrated on relaxing her sphincter and the walls of her anus to accommodate Loyd’s erect penis.
“See… that’s better already I can tell by the look on your face,” Loyd smiled down at her, his dark eyes twinkling.
Watching Sarah’s face screw up into an anguished, agonising mask, tears running down her cheeks in runnels of black mascara as the sudden paroxysm of pain hit her when he rammed his steely phallus into her tight passage gave Loyd an jolt of evil pleasure. He was tempted to pound her into the mattress, jackhammering his cock in and out of her tight asshole as she screamed and tried to fight him off, but that wasn’t who he really was. The short jolt of passing agony he had caused Sarah was enough of a stimulant to satisfy that fleeting primal urge. Now he wanted to enjoy fucking her and make her enjoy it too, as much as she wouldn’t want to.
The truth was that when Sarah had bucked and roiled under him, her anus clenching and unclenching around his cock, trying to expel him, Loyd had come dangerously close to orgasm. He had already been stimulated watching Salesi face-fuck her while he sat on her legs and rubbed his cock on her nylon-sheathed legs and further stimulated when he kissed her and stroked her body and when he had slammed his cock into her tight hole and she had jerked and jolted underneath him Loyd had nearly climaxed.
He was now content to lie still on top of Sarah, feeling her spongy tunnel contract and dilate around his cock, feeling her body lie compliant beneath him, breathing in her perfume, looking into her pretty face made even prettier by her ruined makeup.
When he lowered his face to hers to kiss her Sarah turned her face away but he chased her lips with his mouth. She couldn’t escape him, being handcuffed and with the weight of his body pinning her to the bed. He kissed her cheek and lapped at the salty tears drying on her face with the tip of his tongue. He kissed her there, softly, comfortingly.
“I’m not going to hurt you anymore,” he whispered in her ear and then nuzzled her earlobe.
“But you already have,” Sarah’s voice was soft and trembling.
“I came here to have sex with you willingly. You didn’t have to force yourself on me,” Sarah sighed.
“You didn’t have to bring your friends to watch and take their turn,” Sarah sounded resigned to her fate.
“If I let go of your legs do you promise to stop trying to buck me off and not to kick me?” Loyd kissed her earlobe gently.
Sarah nodded compliantly. Her legs were starting to ache being pushed back against her body.
“You have amazing legs by the way. I’d love to feel them wrapped around me,” Loyd whispered and unhooked his elbows from under Sarah’s knees and allowed her to lower her legs so that she could rest her high heels on the bed.
Sarah would never admit it in a thousand years but now that her legs had stopped aching and the pain in her anus had subsided it felt quite nice having Loyd’s firm body lying on top of her, his cock inside her, his lips caressing her cheeks and earlobes. She still felt helpless but she also felt very feminine, like a heroine being held captive by a dastardly rogue in a movie.
Loyd’s lips found the corner of her mouth and he kissed her there softly. He was in no rush and he continued to kiss her, closed-mouthed, as he stroked her hair and then her cheek. His other hand slid down her body and stroked her thigh, once again caressing the welt of her stocking and playing with her garter clasp. Sarah felt his cock undulate inside her but he wasn’t thrusting, he was content to leave his phallus buried inside her unmoving while he kissed and fondled her.
God help her, Sarah was beginning to become aroused herself. Loyd’s muscled body fit snuggly against hers, his cologne was something musky and manly, his lips were soft and sensuous, his cock fit perfectly inside her anal sheath and his glans pressed on her prostate, the girth of his penis stretched her sphincter pleasantly, causing little ringlets of pleasure to radiate from the sensitive sinew and a deep resonance began to diffuse along her rectum.
Loyd’s flat belly was pressing against her panty-swathed penis, the silky fabric caressed her slowly hardening cock. She knew that Loyd would soon become aware of it, if he hadn’t already, and she hated herself for responding this way. Her body was betraying her. If not for the ache in her arms and the chafing on her wrists from being handcuffed to the bedhead reminding her that she was being held captive, she could be forgiven for thinking that Loyd was actually making love to her, not raping her.
Loyed gently turned her face to meet his and Sarah did not resist. Nor did she resist when he pressed his lips to hers. Nor did she resist when his tongue slipped into her mouth.
Instead she let out a muffled moan and returned Loyd’s kiss, her tongue sought his. She raised her legs and wrapped them around Loyd’s svelte waist just like he had told her that he wanted her to. She gave in to her primal urges.
“When rape is inevitable, just lie back and enjoy it. Isn’t that what you said?” Sarah broke the kiss long enough to gasp and then she dug her heels into Loyd’s flanks encouraging him to do what she wanted him to do.
Loyd smiled briefly and she was once again taken by his handsomeness before his face closed in on hers and he kissed her passionately as he slowly began to fuck her.
The pillows that Loyd had placed under the small of Sarah’s back positioned her body perfectly to allow him maximum penetration while she lay in the missionary position. Sarah had read a missive somewhere that a hard cock has no conscience and she discovered that she was not immune. As the pleasure began to build in her anus and her groin she began to raise her bottom up to meet Loyd’s thrusts so that his cock went all the way inside her and his scrotum osculated against her buttocks. The movement also caused friction between her hard cock and Loyd’s belly. Frisson’s of delight rippled along her engorged member as her slinky panties rubbed the delicate flesh.
Loyd smiled inwardly when Sarah capitulated. Her kisses were passionate and enthralling, her lips soft and yielding, her tongue beguiling, he loved the sensation of her diaphanous nylon stockings chafing his flanks, the softness of her round buttocks, the hardness of her cock pressing on his belly and most of all he adored the way her sphincter clasped around his hard rod as the walls of her anus kneaded his shaft as he slowly thrust it in and out of her tight, slick hole. She did something with the moist fleshy muscles of her back passage that made his cock feel like it was being milked by a velvet glove.
Sarah was oblivious to what was happening around her except for what Loyd was doing to her body and mind. She did not notice that Salesi and the two other shadowy figures she had glanced out the corner of her eye earlier had approached the bed and were watching Loyd fuck her. They were naked and improving their erections and grinning at each other.
“I can’t wait to take my turn,” one of the men whispered to the other.
“I’m going to smash that bitch’s ass until she howls,” the other man replied.
“She sucks cock real good too,” Salesi joined the conversation.
Loyd broke off kissing Sarah just long enough to give them a withering look that implied they should shut the fuck up until he had finished and the three men complied, content to stroke their burgeoning erections and wait their turn. Loyd pressed his lips against Sarah’s mouth and continued to kiss her while his long, thick member slid steadily in and out of her asshole. Her eyes were closed in blissful concentration as Loyd’s cock ignited the pleasure centres deep in her anus and she was oblivious to her surroundings. The only time she opened her eyes was to gaze lovingly into Loyd’s deep, dark eyes and smile up at him. When he began to kiss her again she writhed beneath him appreciatively.
Her cock was leaking a continual flow of pre-ejaculate which saturated the front of her panties and Loyd could feel the warm, slick excretions on his belly. Sarah had begun to issue a deep resonate moan as she approached climax. She locked her legs around Loyd’s flanks even harder and scissored them so that her nylon-sheathed legs tantalisingly excited his fervour, her heels scoured the small of his back as she encouraged him to fuck her harder and faster.
Loyd could feel her cock throbbing against his belly and her sphincter tightening around his cock. Her tongue was like a snake, writhing in his mouth, her kisses demanding and insistent. The feel of her body beneath him, her nylons rubbing his skin, her mouth sucking his essence, the smell of her perfume and the taste of her lipstick was an overpowering aphrodisiac.
Sarah was experiencing a sensory overload. Loyd’s passionate kisses were sublime. The feel of his hard, muscled body pressing against hers was rhapsodic, the feel of his hard cock jackhammering inside her tight channel was euphoric. His very masculinity, his insistent humping, his need and fervour incensed her. His shaft ignited the pleasure receptors ringing her sphincter and the wall of her anus and his glans triggered the sensors in her prostate. Her cock was pressed hard against Loyd’s flat stomach and every time he thrust into her, his belly rubbed her silky panties against her quivering organ.
She could feel her nylon stockings encasing her freshly-shaved legs, her skirt bunched around her waist like a saltern, she could feel her satin panties stretched tight around her buttocks and scrotum, the gusset eased aside so that Loyd could ravish her anus. She could taste her lipstick, smell her perfume, feel the nap of her wig tickle her neck, her nipples were erect and highly sensitive. She had never felt so womanly lying fully-clothed underneath this man who was using her body for his pleasure and in doing so was inducing the most incredible sexual phenomena that Sarah had ever experienced. She had become the slutty secretary that Loyd had asked her to be when arranged the assignation.
“Oh god yes!” Loyd howled and he pulled Sarah’s body tight against him and kissed her hard as his body shuddered with the paroxysm of orgasm and he expressed his essence deep inside Sarah’s rectum.
Sarah felt his cock quiver inside her and she realised that Loyd was planting his seed deep inside her and it triggered her orgasm. She began to shake almost uncontrollably the apotheosis of her climax washed over her like a tidal wave of euphoric bliss. She creamed her panties and Loyd could feel her cock juddering against his belly and then her warm creamy spunk slathering against his skin.
He drove her down into the bed and pounded his cock in and out of her tight hole, her nylon-sheathed limbs scissoring against his flanks, her breathing ragged, her need demanding as she pressed herself against him and her anus rippled and undulated as she extracted every scintilla of his semen.
The three men standing next to the bed watching on had never seen such sexual fury. The pretty transvestite and the well-hung handsome stud were locked together in a catalytic explosion of lust, need and desire. The men wanked their cocks as they waited their turn, imagining all the things they were going to do to Sarah to sate their lust.
To be continued…
Cabin 121 Park Motor Lodge, Engadine NSW, Australia
Sarah lay under Loyd feeling his semen seeping from her sphincter and dribbling between her buttocks. She was still feeling the aftereffects of her orgasm and oblivious to her surroundings but then the handcuffs rattled as Loyd moved on top of her and she suddenly became aware of the three other men standing next to the bed waiting their turn.
Once again she pondered the happenstances that had led to her current predicament. Of course she was well aware of the circumstances as to how she had been lured to the cabin but her thoughts drifted further back in time to when she had first become aware that she was different to most of the other boys and how her compulsion to crossdress and her inclination towards promiscuity had begun.
Kurrajong Street, Sutherland NSW, Australia – 1979
Stefan Lang had been a crossdresser for as long as he could remember.
He'd started out like most of his ilk, fascinated with ladies lingerie, hosiery and shoes and enchanted by frocks, crinolines, skirts and blouses. Like most serious crossdressers, he had graduated from nicking his mother's and sisters 'unmentionables' from the washing basket and rummaging through their wardrobes to try on their clothes when he had the place to himself. Stefan made choices that separated him from the 'hairy-panty-wearers', determined to learn how to present himself as realistically feminine as possible.
He saved his pocket money and his earnings from his paper route and the odd jobs he performed for cash and purchased himself a proper wardrobe. A small selection of clothes that fitted his svelte frame, a pair of high heels that fit, a decent wig and his own cosmetics. Most of the clothes came from the Op Shop as did the heels but the lingerie and hosiery and underwear came from Myer. Stefan had made the train journey from Sutherland to Sydney to acquire his necessities, the journey taking around an hour each way.
Stefan did this for two reasons. One: there was every chance he would run into someone he knew in the local Op Shop and nearby department store and it might prove embarrassing explaining why he why he was purchasing ladies clothing. Two: There were more stores to choose from and a better selection of goods in the city.
The women at the Op Shop on Oxford Street were used to men coming in and purchasing women's clothing and more than willing to help them find attire that suited them and fitted properly. Oxford Street was at the centre of Sydney's burgeoning LGBTI community, although in the 70s the queer community had not begun their appropriation of half the alphabet and were known disparagingly as: poofters, homos, and ponces. Those who had a predilection to dress up as women were: fairies, nancies and nellies. Another reason that Stefan needed to shop in secrecy.
Myer was one of the largest department stores in the city at the time and Stefan stuck out like a sore thumb as he roamed the aisles of the lingerie department selecting lingerie and hosiery. The hoity matron behind the counter had given him a withering look when he took his purchases to the sales registry and Stepfan had blushed and stammered his way through the exchange of cash for goods. There was no 'tap-and-go' in those days.
The wig he had purchased in a costumers on Oxford Street. The shop was little more than a front for crossdressers and transgender women (another term that had yet to be coined) to purchase their necessities in a safe space.
He'd seen the Bettie Page wig sitting on a wig stand in the storefront window and immediately fell in love with it. The combination of thick, straight bangs and flowing curls that spanned just past her collarbones was Bettie's trademark. The wig had nearly cleaned out the remainder of his savings, but on the train ride back to Sutherland Stefan was so excited that he counted down the stations until his train arrived at Sutherland station and then he ran all the way home.
Stefan had to wait for what seemed like an eternity for Saturday when his mother took his sister Julie to her weekly netball carnival, this time being held at Miranda. They would be gone all day and afterwards his mother was treating Julie to a shopping spree at Miranda Fair where they would also have dinner, meaning Stefan had the house all to himself all day.
As soon as they left Stefan showered and plucked the few hairs that grew on his chin and in the hollow of his chest. At school Stefan was sometimes teased in the changeroom because unlike most of the other boys who had suddenly become hairy yetis when they hit puberty, Stefan's body and legs remained smooth except for the patch of pubic hair between his legs.
Stefan pretended that he was jealous of the other boys hirsuteness and muscled frames but secretly he was pleased that his body had become muliebral, svelte and curvy rather than rugged and masculine like his peers. It was easier to fit into his mother's and sister's clothes but now he had his own wardrobe which he was keen to put to the test in the privacy of his bedroom.
Dressing enfemme for Stefan quickly became more than just something sexual or fantasy fulfilling. He'd adopted the femme name Sarah because it was close to 'Stefan' but not too close. Sarah wanted a name that reflected a complete change of gender and praised herself for not adopting the name Stephanie which would have continually reminded her that her 'boy name' was Stefan.
When she dressed, Sarah did not just dress like a girl, she became a girl both physically and mentally. It was a total transformation. She was another person, unencumbered by her male identity. She adored her small collection of feminine essentials, especially her Bettie Page wig. She practiced her makeup skills and became adept at presenting her own unique, feminine persona. She learned to walk and talk like a girl and instinctively adopted feminine mannerisms.
It was the little things about being a girl that Sarah adored: the faint hiss of her nylons as they rubbed together, the gentle flutter of the hem of her skirt on the back of her legs when she walked, the taste of her lipstick, the smell of her perfume, the gentle caress of her hair on her neck and shoulders.
She looked forward to Saturdays when she had the place to herself and she could roam around the house freely. Simple things brought enjoyment such as reading Julie's Dolly magazines or her mother's Women's Weekly, washing and ironing her clothes, trying on different outfits. She'd try to imitate Bettie Page, wearing a tight basque, fully-fashioned stockings and severe makeup or maybe dress as a sexy secretary dressed in a tight pencil skirt, satin blouse and fleshtone sheer-to-the-waist pantyhose.
Sarah was limited by her wardrobe. She had only one wig and one pair of black high heels and her collection of op-shop clothing but she made do with what she had and perfected her looks.
Of course there was a sexual component to Sarah's compulsion to present femme. When she had finished 'playing house' she would retire to her bedroom and drag out the small collection of soft porn that Stefan kept hidden under his bed. Of course there was a Bettie Page magazine but also some editions of Fiesta, Club International and Escort, where women posed provocatively in sexy lingerie and titillating stories were published, usually claiming to be real-life adventures. The threads to these stories were the usual schlock that titillated the male readers: naughty nurse, licentious secretary, horny next-door neighbour or busty librarian. Most of the women characters were at first reluctant to unleash their secret desires but the male protagonists always got into their knickers.
About an hour before her mother and sister were due home from their weekly sojourn Sarah would look at the pictures in the magazines or read the stories while she draped a nylon stocking over her erect member and slowly bring herself to climax. In the fantasies she wove while she masturbated she was one of the women in the pictures or a female character in one of the stories and some faceless but surely handsome man would seduce her. When Sarah climaxed she recalled how wonderful it had felt when Rita Blackwell had stroked Stefan to climax in the bushland behind the scout hall. Rita had lifted her skirt while she did it so that Stefan could stroke her pantyhose-sheathed thighs and panty-clad pubis.
At eighteen years of age Stefan was still a virgin when he'd had the handjob from Rita Blackwell. Rita had left school at sixteen and was still working at the same grocery store when she turned eighteen and became promiscuous. She was the type of girl who would show you her knickers for a couple of bob and she would give you a handjob for a dollar if she liked you.
The stories in the magazines that Sarah read were not exactly explicative when it came to the sex acts themselves but even though Stefan had no father to give him 'The Talk', Stefan knew enough about the mechanics of sex and exactly what words like coitus and fellatio entailed. In Sarah's imagination she was the one performing fellatio or lying on her back with her legs open, while the faceless but handsome man lay on top of her rutting.
Everything changed one fateful Saturday afternoon. Sarah was dressed in a rather demure navy-blue A-line skirt, a crisp white blouse, and her black high heels. Underneath she wore black satin full-cut panties and a matching bra stuffed with balled up pantyhose because she had no breastforms and at this stage of her life didn't even know they existed. Of course she was also wearing hosiery, in this case cheap tan pantyhose she'd purchased at the Coles.
She was sitting in the loungeroom flicking through Julie's latest edition of Dolly, envious of the young women pictured in the fashion section when she suddenly became aware that she was not alone.
Billy Barton stood directly in front of her, staring lustfully at her, and by the bulge in his jeans his intentions were obvious.
Billy Barton lived across the street from the Lang's and was in twelfth form, the same form as Stefan but Billy was one year older. He was tall and lanky and a better than average cricketer and footballer but disliked by his peers. He was a bully both on and off the playing fields and had been appointed as a school prefect and he thought nothing of twisting the ear or cuffing the back of the head of any student he found breaching the school rules. Male students either feared or avoided him and the girls were not attracted to his plain looks and scruffy appearance. His clothes were far from fashionable hand-me-downs or purchased at discount stores and his hair was lank and always looked unwashed. Billy was also afflicted with teenage acne which at the age of nineteen was a curse.
Billy converted the frustration and misery caused by his family's financial status and lack of acceptance into anger and was inclined to lash out without warning. Fear of reprisals kept those who were the victims of his anger from reporting him. In some ways he and Stefan were similar in that they both came from fatherless homes, were far from affluent, and both solitary. But in other ways they were opposites. Stefan was meek and studious whilst Billy was brash and athletic.
"How long did you think you could get away with this?" Billy asked as if he was just confronting Stefan in the school quad rather than having broke into his house.
"How did you get in?" Sarah's voice was a terrified whisper.
"You left the door unlocked you dickhead. I kicked my football over your fence a few Saturday's ago and when I came over to retrieve it I saw you through the window. At first I thought you were a girl, one of Julie's friends, but I knew that Julie had netball all day Saturday and your mom's car was gone," Billy answered Sarah's question and extrapolated further.
"What are you doing here?" Sarah was still terrified.
If Billy were to blab to the students and teachers at school, or even worse, tell Stefan's mother or sister that Stefan liked to dress in ladies clothing, Stefan's life would be ruined.
"I've been watching you putting on your little fashion shows, parading around the house like a girl and of course I've seen you wanking while you look at those dirty magazines," Billy hadn't answered Sarah's question and the sneer on his face did not bode well.
"You still haven't told me what you are doing here," Sarah tried to sound defiant but she just sounded meek.
"You even talk like a girl when you're dressed like that, do you know that? You're very pretty. I doubt anyone would know who you were under that wig and makeup and your legs are stunning," Billy still didn't answer the question but while he was talking he took a step closer to Sarah and began to unzip his fly.
"If you give me a headjob, I won't tell anyone I promise," Billy's sneer became a leer.
He was looking at her legs and up her skirt at her panties and Sarah realised that she was sitting with her legs wide open, the discarded magazine beside her. She demurely closed her legs and straightened her skirt.
"You even act and move like a girl Stefan," Billy chuckled.
"It's Sarah!" this time Sarah did sound defiant.
"Ok Sarah, you suck my dick and I won't tell everyone that you are a crossdressing sissy," Billy took another step forward and his cock was inches from Sarah's face.
Sarah had to think quickly. At the moment Billy Barton held all the cards. If he blabbed, the consequences were unthinkable but if Sarah did what he asked, Billy became complicit. She could blackmail him in return. Sure he could out her as a Nancy but it would be her word against his regarding her giving him a blowjob. Deep down inside, where Sarah kept her secret thoughts and yearnings, hadn't she always wanted to know what it was like to be woman in that way? Her masturbatory fantasies involved a faceless handsome man doing things to her. Billy Barton was far from handsome and in many ways despicable but Sarah was trapped. It might have been her subconscious justifying her actions but she made the decision then and there to cross the Rubicon.
"You can't tell anyone," Sarah whispered.
"Don't tell me what I can and can't do," Billy waggled his hard cock in Sarah's face.
"Ok, here's the deal. You call me Sarah. You treat me like I'm a girl. You never mention Stefan's name or refer to me in the male vernacular while I'm dressed like this," Sarah was becoming confident.
This might be her way out of being publicly disgraced whilst at the same time discovering if her sexual fantasies were anything like she imagined them to be.
"Fine with me. I don't want anything to do with Stefan, just with you... Sarah," Billy said impatiently.
Sarah actually smiled as she reached out and put her hand on Billy's rampant organ. It was long and smooth with blue veins running down the girth of it and instinctively she traced one with her red-painted fingernail. Billy shuddered and his cock juddered. He unbuckled his jeans and they fell around his ankles.
Sarah wrapped her fingers around the fleshy protuberance and two things happened. She felt herself becoming aroused rather than disgusted and a wave of femininity washed over her. She had never felt more womanly as she did when she slowly began to stroke Billy Barton's long sleek cock. If it had been Stefan Lang masturbating another boy it would be gay, it would be queer, it would be... unimaginable! But it wasn't Stefan. It was Sarah Lang who had secretly wondered what it would be like have sex with a man.
Billy stared at Sarah's legs, appreciating their length, their shape, their downright sexiness, clad as they were in tan pantyhose. Billy was a leg man or more specifically, a leg and ass man.
Sarah felt the veins throbbing in the velvety flesh of Billy's hard cock and watched marvelled and open-mouthed as a bubble of translucent precum formed at the eye and then formed a filament of silvery pre-ejaculate that hung from the shiny pink organ. She caught the slippery liniment on her fingertips and rubbed it into the shaft, working her fingers upward to the bulbous glans.
"Open your legs," Billy whispered, his face a mask of concentrated bliss.
He too had received a handjob or two off Rita Blackwell but it was nothing as sexually exciting as this. All Billy saw was a slim teenage girl with magnificent legs, her pretty face framed by a straight black fringe with raven curls cascading down her cheek and neck. Her eyes were sparkling green, enhanced by her heavy makeup. Her lips were lush and full and painted with ruby-red lipstick and he longed to kiss them but wondered if that might be taking things too far.
Sarah obligingly opened her legs and Billy put out his hand and ruched her skirt up so that he could see those luscious thighs and the Vee of her black satin panties. As he did so she began to stroke Billy's cock with long slow strokes, featherlightly caressing his shaft and glans. With her other hand she cupped his scrotum and gently caressed it. The seepage of precum became a steady stream as the sensation of Sarah's fingers manipulating Billy's cock began to build into a boiling conglomeration of carnal delight.
Billy's eyes alternated from looking at Sarah's beautiful face, which was lost in concentration as she stared at Billy's hard throbbing cock, awestruck by the firmness and liveliness of it, knowing that it was she who had brought it to life and was pleasuring it so lovingly. Then he glanced down at her luscious pantyhosed thighs and those lace-fringed black satin panties. He briefly wondered how Sarah managed to hide her cock but at the moment it the least of his concerns. He could feel his orgasm building and he desperately wanted to stick his cock in Sarah's mouth and blow his load.
But it was too late.
Sarah was expertly manipulating Billy's cock, her long slender fingers stroking the sensitive protuberance, alternating between a featherlight caress and a buffering flutter. She dragged her polished fingernails lightly across his fraenulum and softly kneaded his scrotum while she did so. She sensed that he was close to extremis and she grasped the throbbing phallus tightly and quickened her pace.
To Billy, Sarah looked vulnerable with her skirt hiked up, her panties exposed, her long legs sheathed in tan nylons, her pretty face a mask of concentration, her lips slightly parted, her perfume invading his nostrils. The sight and smell of her and the way she expertly massaged his cock was too much to bear. Her countenance was overpowering and Billy couldn't hold back any longer.
"Oh, my goodness!" Sarah squealed as Billy's cock erupted.
A scorching rope of glutinous semen splashed onto her thigh, the translucent plasma soaking into her stocking while the whitish goop of his spermatozoa clung to the nylon. It felt wet and warm and the musk of it assaulted her nose. A second freshet of jizz spattered on her leg, a third doused the front of her blouse. Geysers of viscous spunk splattered her legs, her skirt and her blouse and still Sarah worked her fingers up and down the pulsing penis while she gently squeezed his scrotal sac, expressing every drop of his seed.
Billy rocked back on his heels as his orgasm overwhelmed him. His first instinct was to close his eyes as the sheer bliss of his climax blossomed in his loins and spread throughout his body but he wanted to see Sarah's reaction.
She seemed fascinated and perplexed that she had invoked such a capricious consequence, although she shouldn't be. After all she had the same equipment which was presently rock-hard and tenting her panties. Billy thought she looked both lecherous and vulnerable sitting there with his cock in her hand, her skirt, blouse and pantyhose spattered with his issue. The sight of this pretty young maiden covered in his ejaculate escalated his orgasm to heights never before experienced.
When the last droplet of Billy's semen dribbled from his cock and spilled onto Sarah's shiny black high heel he exhaled slowly as his breathing began to return to normal. Sarah suddenly realised the enormity of what she had done. She was soused in Billy's warm, pungent milt. She could feel it cooling on her flesh where it had soaked through her hosiery and blouse. She reeked of it.
She let go of Billy's withering erection and his scrotum and demurely put her hands in her lap. Her red fingernail polish glistened with Billy's sperm and her fingers were sticky with it. She pulled down the hem of her skirt and straightened it, noting the two long tendrils of spunk drying on the fabric, and surprisingly, thinking to herself that she had better get the skirt into the wash before it stained.
"Well that was pretty awesome Sarah. You are a first-class wanker," Billy chuckled as he hitched up his pants.
An awkward silence followed while they both came to grips with the enormity of what had just occurred.
"I'll be back next Saturday to get that headjob," Billy finally announced.
"Mom and Cindy won't be back until late next week," Sarah blurted out and immediately wished she hadn't.
Then Billy surprised both himself and Sarah as he leaned down and pressed his lips against hers and kissed her. The kiss lasted only a few seconds but they both realised the significance of it. Billy was attracted to her and it was an acknowledgement that he thought of her only as a girl.
Billy broke the kiss and left the room leaving Sarah sitting perplexed and sexually stirred. When she heard the front door close she pulled her hard acing cock from her panties and masturbated. She thought of Billy's rampant cock juddering in her hand as he climaxed and relived the instant that the ropes of his steaming ejaculate spurted from the eye of his cock and spattered on her body and legs. But when she orgasmed she thought only about the kiss... the gender affirming kiss. Billy thought of her exclusively as a girl and that meant more to her than anything.
As she stripped out of her cum-spattered clothing and put them in the wash she gave consideration to what had happened. It was a life changing experience. Yes, Billy wasn't handsome and he was a bully... but he was now her bully. The cheap pantyhose she had been wearing did not go into the wash. She wanted to keep the cum-soaked nylons so that she could sniff them when she masturbated at night. They were conclusive evidence that what had happened was not a dream.
Kurrajong Street, Sutherland NSW, Australia -- One Week Later
During the week all Billy could think about was his encounter with Sarah. When he'd first entered the Lang's backyard to retrieve his football and peeked through the curtains into Sarah's house and realised what he was looking at, his natural instinct had been to bully and blackmail Stefan Lang. Billy was no homo and at first what he witnessed repulsed him... a young man dressed in ladies clothing. But he didn't do anything about it at first, instead he kept returning to the Lang's yard every Saturday, secretly watching Sarah intently, studying her through the window. Once he got past the fact that it might be Stefan Lang wearing those clothes but the gorgeous, sexy maiden that Stefan became when transformed presenting no male attributes whatsoever, his attitude changed.
He was still going to blackmail and bully the pretty crossdresser but he had to admit that he was becoming attracted to her and that's when he set his mind to confronting her and demanding a blowjob. When he had finally confronted the crossdresser and found out that her name was Sarah and that was not a skerrick of Stefan to be seen in the comely young woman who sat before him terrified, his perspective adjusted even further. As it turned out he hadn't received the blowjob that he wanted. He had become overexcited and ejaculated when Sarah masturbated him but he had to admit that it was very satisfying.
Billy had surprised himself when he kissed Sarah before he left. It was impulsive but deeply gratifying. The kiss lingered on his lips.
At school, first to fourth form girls wore white ankle socks with their school tunics in the hot Australian summer but in winter they wore tights. The young women who continued their scholastic endeavours to matriculate in the fifth and six forms had a more flattering school uniform: green A-line skirts, which the girls wore as short as they could get away with, white cotton blouses, green blazers and black court shoes. They exclusively wore tan or fleshtone pantyhose rather than ankle socks as a symbol of their maturity. Fifth and sixth form girls were entering womanhood as their eighteenth birthday passed them by.
Billy was surrounded by them during the day, pretty young women with coltish legs, fully-developed breasts, faces embellished with makeup and at an age where they were boy-hungry. But not for Billy. His hand-me-down clothing, unfashionable dull greasy hair, pockmarked cheeks and surly disposition placed him well below their standards. Even the ugly-ducklings and fatties eschewed him.
As he sat in the quadrangle eating his savourless homemade sandwiches he ogled these young women. They were mostly blondes and brunettes with their hair styled in the latest fashions but none of them had hair like Sarah's glossy black Bettie Page. They would consider it old-fashioned but Billy adored the way Sarah wore her hair. The girls were allowed to wear makeup of course but it was heavily policed by the staff and prefects. None of them had Sarah's emerald green eyes enhanced with smoky eyeliner, heavy mascara and exotic eyeshadow or full lips tinctured with bright red lipstick which matched her nailpolish. The girls makeup was by necessity sedate and muted.
Sure, most of them had comely long legs clad in shimmery or translucent pantyhose, they had firm buttocks, wide hips, trim waists but so did Sarah. Billy knew that whatever Sarah used to project the illusion of having a bust was just that, an illusion, but he didn't care. He wasn't really a 'tit man' anyway.
None of the young women could hold a candle to Sarah in his opinion. The more he thought about Sarah, the more he thought about Sarah being his girl. As to the secret Sarah kept in her panties... he thought it best not to dwell on it.
His masturbatory fantasies revolved about what he was going to do about Sarah the next time they met.
Cricket season had wrapped for the year and he was training heavily for the coming rugby league season and when the competition started his Sundays would no longer be free. But Billy now had something to keep him busy on Saturdays as well. That something would be Sarah Lang.
Of course he studiously avoided Stefan Lang. They didn't have any of the same classes and Stefan took his lunch in the library and the few friends that either of them had did have moved in the different circles. In Billy's mind Stefan Lang was an insignificant individual of no concern to him, other than that he lived across the street.
Sarah however was his girl.
*****
Stefan Lang was suffering a similar quandary. Long before Sarah's encounter with Billy Barton, Stefan would often drift off and become Sarah in his mind when his attention waned but Stefan came out of a reverie on the Tuesday after what he only ever referred to as The Encounter to find that he had daydreamed through the whole fifth period's Modern English lesson, thinking about what Sarah was going to wear on Saturday and what Billy might do to her.
Every night since The Encounter Stefan had gone to bed early and locked the door to his bedroom. It was too risky to fully transform into Sarah with his mother and sister at home so he mentally became Sarah, put on a pair of pantyhose and silky panties and a rayon chemise and slipped into bed. Sarah teased her cock through the silky garments whilst sniffing the pantyhose that Billy had sprayed his spunk over, recollecting the experience, until she couldn't hold back any longer and creamed her panties. At the moment of climax she relived the kiss.
Common sense told Stefan that he should get rid of all of Sarah's trappings and stop crossdressing. He should find something else to do on Saturdays when his mother and sister were out of the house; something that kept him away from home all day. It was also blindingly obvious that he should avoid Billy Barton at all costs.
But Sarah kept thinking about that lingering kiss. She kept thinking about how Billy had treated her like she was a girl. She kept thinking about that pulsing penis that had erupted in her hand and smothered her with hot spunk. Hadn't Sarah always wondered what it would be like to have sex with a man? Sure Billy had threatened her, bullied her, blackmailed her... but he had kissed her.
Stefan knew that the compulsion to crossdress would not just go away. He'd found what little there was written about transvestic disorder in the psychology section at the Sutherland Shire Public Library and was familiar with the urge to purge.
He knew that purging was an attempt to sever oneself from crossdressing by disposing of all physical reminders of it, usually triggered by feelings of guilt, shame, or social pressure, as well as the fear that embracing crossdressing might complicate or threaten one's personal relationships, professional life, or self-image.
The problem with purging was that it can be costly and distressing, especially if it's done impulsively. It might create a short-term sense of relief, almost like a cleanse. However, Stefan knew that the reality was that crossdressing was an intrinsic part of his identity and that purging would provide only temporary relief and before long the urge to crossdress would return, stronger than ever.
Sarah was a part of him and losing her would be like lopping off a limb or losing part of his soul. The problem was that Stefan and Sarah's shared psyche was splitting. Sarah's individuality was becoming dominant and Stefan's identity was fading into the background. There was a danger that Sarah would become the prevailing entity while Stefan disappeared into the shadows.
Those considerations were put aside as the weekend loomed. Saturday was Sarah's Day and Sarah was both anxious and excited about her forthcoming encounter with Billy Barton. The boy was an unattractive, unkempt, brash, rude bully but so far he told no one of his encounter with Sarah, at least as far as she knew, and if he had it would have been all around the school. So they shared a secret. And after all... he had kissed her.
Saturday
Sarah was both trepidatious and excited as her mother's car backed out of the driveway. Julie's netball carnival this Saturday was being held in Helensburgh, a little township near the south coast and they would be gone all day and because Helensburgh was so far away, his mother and his sister would get dinner on the way home and Sarah would have the house to herself all day and into the evening.
She imagined Billy Barton peeking through the curtains of his house across the street watching the Lang's Kingswood station wagon backing out with mother and daughter embarked. He would know that Sarah needed time to transform so she didn't expect him straight away. They had agreed that neither of them would acknowledge Stefan's existence, that Billy would only ever meet with Sarah.
She was already showered and shaved and she sat naked at her desk which had been cleared of the usual clutter of homework, textbooks and stationery. Her makeup was laid out carefully on the desk before a small, freestanding makeup mirror, a pot of Ponds Cold cream and her nailpolish. Her Bettie Page wig sat on a homemade paper mâché wigstand, already brushed and ready to wear. Her excitement built as she carefully applied her makeup and the transformation began. She sprayed herself liberally with Dior perfume, borrowed from her mother's bedroom. There was some risk in using her mother's perfume but she doubted that her mother would miss a few puffs of her favourite scent. Sarah made a mental note to buy her own perfume with her pocket money next time she went shopping.
As she carefully applied the deep red fingernail polish to her nails she was well aware of the little things she was doing to make herself more appealing to Billy. She didn't always paint her nails and seldom wore perfume, she had used nearly half a bottle of Listerine to ensure her breath was sweet, she had tweezed every stray hair from her body. She had eaten nothing the day before or breakfast this morning because she was so nervous. Her hands were shaking when she applied her eyeliner and she'd had to remove it and start again after taking a slug from the gin bottle from the little bar in the corner of the sitting room.
She pulled the footlet of an old stocking over her scalp and pushed all of Stefan's shoulder-length chestnut hair under the makeshift wigcap and carefully put on the Bettie Page wig, fussing with it and pinning it in place before giving it another brushing. She looked in the mirror and saw a very seductive young woman looking back at her. She smiled to herself thinking that if Julie ever tried to leave the house wearing the makeup that Sarah was wearing their mother would call her a slut and make her wash it off.
As she stepped into the tight black basque, pulled the fully-fashioned stockings up her freshly shaven legs and shimmied into the red satin -- black lace-trimmed panties, Sarah was well aware that she was dressing very provocatively. She could just as easily have worn a skirt and blouse or one of the two dresses she owned and still looked attractive but she was driven by a subconscious desire to present herself as sexy as possible. She clipped on her drop-earrings, put on her bangles and necklace; all cheap costume jewellery, and stepped into her black heels and looked at herself in the full-length mirror fitted to the inside of the wardrobe door.
For an instant she had an overwhelming urge to wipe off her heavy makeup and replace it with something subdued, to take off the basque and stockings and put on a modest skirt, sensible blouse and cheap pantyhose and present herself as demure. What she really should do was to remove all of her femme trappings, put on her 'boy clothes' and sneak out the back door and run to the railway station and spend the day well away from the house on Kurrajong Street.
But she did neither of those things. She left the bedroom she occupied in the three bedroom bungalow her mother owned and went into the living room and poured herself a gin and tonic and waited nervously for Billy Barton to arrive.
There was a tap at the front door and then Billy entered the short hallway and walked down to the loungeroom.
When Billy had seen the Lang's Holden Kingwood drive away he had suddenly became nervous. All he had thought about all week was Sarah and the things he intended to do to her. He imagined those full lips circling his cock. He'd never had a blowjob but he'd seen plenty of porn in which women fellated men and he could only imagine how wonderful it must feel. But he was still trepidations. He was no homo. He'd joined in the melee when a member of his rugby club had been accused of being gay and the unfortunate boy had been beaten half-senseless in the changing room by his teammates.
But anyway, no one was going to find out. Sarah was certainly not going to out herself, that's for sure. What happened in that little brick veneer cottage would remain a secret between them.
Any semblance of reluctance disappeared when he entered the loungeroom and saw how Sarah was dressed. She looked beautiful and sexy and he stood in the doorway and he examined her from head to toe. He started with those long legs clad in black, fully-fashioned stockings and followed them up from ankle to thigh. He caught a glimpse of her red stain panties, incongruent to the black basque and black stockings and heels and her raven hair. Her waist was cinched which emphasised her perky bottom and trim belly. He noticed that the cups of her basque had not been filled but her flat-chested appearance did not distract from how devastatingly raunchy and attractive she looked.
Finally he looked at her face. She looked stunning in her heavy makeup which emphasised her emerald green eyes and luscious red lips, her hair fanned around her neck and shoulders. What little flesh she exposed was alabaster white and flawless, accentuated by her black attire. She obviously spent very little time in the sun. He locked eyes with her and saw the trepidation in them but there was also something else... anticipation maybe?
He really didn't know how Sarah would react. Last time she had been reluctant, which was understandable given that she was effectively being blackmailed, but there was no doubt that she had become a willing participant in their brief tawdry tryst. He had no intention of today's encounter being brief and given the way she was dressed there was no doubt that she was presenting herself provocatively. When Sarah ran the tip of her tongue across her bottom lip any doubts he had dissipated and he strode across the room and pulled her into his arms.
Sarah noticed immediately that Billy had gone to some lengths to present himself as genteel. His usually lank oily hair was freshly washed and neatly combed, his clothes were clean and pressed, his face was freshly scrubbed and his acne was hardly visible. Dare she think it, he actually bordered on handsome. She could smell the Lux toilet soap and Old Spice aftershave from across the room. She couldn't help but being flattered that he had gone to the trouble of presenting himself at his best.
When Billy strode across the room and took her in his strong arms Sarah nearly swooned like some actress in a B romance movie. He took her breath away and she clung to him, feeling his muscled body pressing against hers. He kissed her and any doubt that Billy was not infatuated with her disbursed. His lips were firm and his tongue slipped into her mouth and it tasted surprisingly sweet. She responded and her tongue met his, her heart was pounding in her chest and she felt a stirring in her loins.
He wrapped her in his arms, gently grasping her shoulder blades. As the kiss continued his hands drifted down to her waist where they lingered for a while before he cupped her buttocks and pulled her into an even more rigorous embrace. She could feel him through his trousers, his hard steely cock pressed into her belly, his breathing was laboured. She had evoked this response. She was responsible for Billy's ardour. She felt a tingle of self-satisfaction that her feminine charms were responsible for his passion.
When Billy took Sarah into his arms and kissed her he realised that his self-doubt was foolish. She moulded herself to him, her mouth open and willing, her lips soft and yielding. Their was no reticence in her reaction. She returned his kiss and clung to him. The feel of her slim body, she scent of her perfume, the taste of her mouth was magical. He became engorged and pressed his cock into her belly and she didn't flinch. She was actively participating, behaving almost lecherous.
He wanted to touch her everywhere, to feel her flawless alabaster flesh on his fingertips, to run his hands up and down those long silken-sheathed limbs, to fondle her panty-clad buttocks, to suckle her tiny nipples, to kiss her until he was breathless. There was a lingering uncertainty as to how to deal with her genitals but so long as he didn't touch them there was no concern as to his masculinity was there? He was holding the prettiest, sexiest, seductive girl in Sutherland and she was willingly giving herself to him. All of those haughty bitches who sneered at him across the quadrangle at school could go fuck themselves.
Billy's hands were all over Sarah's body. He stroked the bare flesh above her stocking-tops then cupped her buttocks, kneading them, feel her perky buttocks jiggle through her satin panties, then his fingers explored her thighs, relishing the silky texture of her stockings, lingering on the gauzy welts and tracing the seams at the back. His tongue was alive in her mouth.
Sarah was breathing heavily and she fumbled with his belt buckle and zipper but eventually was able to ease his trousers down and slip her fingers inside his underpants to free his rampant member. It was already fully engorged and leaking precum. She stroked it and felt Billy's body shudder as she worked her fingers along the shaft.
Suddenly Billy broke the kiss and removed his hands from her lower extremities and placed them on her shoulders. He pressed downward on them firmly.
"You know what I want Sarah," Billy whispered, his deep blue eyes locked on hers and she could see the need; they were imploring her.
Sarah had thought about this moment for a long time and now it was here. She dropped to her knees and Billy's phallus was inches from her face. It looked almost ready to erupt, a filament of clear pre-ejaculate hung from the eye. She took a deep breath, steadied her nerves and took him in her mouth.
Billy's cock tasted of Lux soap and salty-sweet pre-seminal fluid. Like any teenager, Sarah had tasted her own secretions and Billy's tasted no different, but, they were his secretions. This young man yearned for her, adored her and wanted her more than anything else in the world right now and that was a powerful aphrodisiac as was the fullness of his flesh on her lips and in her mouth. She explored the bulbous glans with her tongue and was rewarded with a freshet of syrupy precum which she savoured and then swallowed.
Billy's hands rested lightly on her head. The feel of Sarah's warm, wet mouth on his member was like nothing he had ever experienced. He watched her plump lipsticked lips close around his shaft while her tongue tickled his fraenulum and circled the corona of his glans. She looked up at him, her emerald green eyes supplicant and sparkling with lust. Seeing his cock inside the mouth of this gorgeous young woman was almost enough to drive him over the edge.
He began to fuck her mouth.
Sarah used her lips to suckle Billy's shaft while her tongue continued to coddle the pink protuberance of his bulbous glans as his cock slid in and out of her mouth. She felt so submissive on her knees before him, submitting to his needs but at the same time she felt so powerful and commanding. She was giving Billy what he wanted but she was giving it willingly. Her cock was stirring inside her panties and she desperately wanted to stoke it while she sucked Billy' fine specimen of manhood but she didn't want Billy to become repulsed if he saw her doing so.
She put her hands on his hairy thighs and moved her mouth up and down on his quivering rod, lapping at it with her tongue while her lips slid back and forth along the sleek shaft. She stroked his scrotal sac and felt it contract as his penis began to spasm.
Freshets of creamy, glutinous milt filled her mouth and rather than being revolted she was delighted by the of taste of the musky essences and gleefully swallowed them. The feel of his cock juddering her mouth, the piquancy of his semen, the feel of his hands pressing her face into his groin, his laboured breathing and guttural moans reflected the intensity of his orgasm. An orgasm she had invoked. Her cock was rock hard and yearned for release but she resisted the urge to touch it and instead she suckled Billy's quivering organ until she had drained every scintilla of his seed.
Billy's knees nearly buckled with the intensity of his climax as waves pleasure radiated from his groin. He looked on fascinated as the pretty transvestite worked her mouth up and down the shaft of cock. When she had drained him he removed his cock from her mouth and helped Sarah to her feet.
She stood before him supplicant, both of them unsure what to do or say in the awkward silence that followed. Billy surprised her when he pulled her into his arms and kissed her, pressing himself against her. Then he released her.
"Thank you darling that was everything I dreamed it would be," Billy whispered as he pulled up his pants, zipped his fly and buckled his belt.
"It was amazing," Sarah admitted and felt both stupid and guilty for saying so.
Billy kissed the tip of her nose and smiled at her.
Sarah was overcome with Billy's tenderness. The brash young man who had broke into her house and threatened her had called her darling and had kissed the tip of her nose affectionately. He was behaving almost gentlemanly and Sarah adored him for it.
It validated her femininity and allure. Billy genuinely liked her, she wasn't just a object for him to use for satisfaction.
He looked at her quizzically while she stood before him ruminating, probably wondering what she was thinking. He kissed her quickly and stroked her cheek.
"Go and fix yourself up, I'm ducking across the road for something but I'll be back shortly," Billy said in an authoritative tone.
Sarah had half-expected Billy to leave as soon as he'd blown his load just like he did last time. Then she remembered that she had told him that her mother and sister would not be back until the evening. She kicked herself for doing so but wondered if subconsciously she had done it intentionally so that he would stay a while.
Is that what she wanted? Did she want Billy to spend the day with her? She had to admit that she kinda liked being bossed about by him and she was enjoying the canoodling and the sex.
She heard the front door open and close as she retired to her bedroom and sat down in front of the makeup mirror and put foundation and power around her mouth, nose and chin and a fresh coat of lipstick on her lips, replacing what had come off during the kissing and fellatio. She turned on the radio and the current big hit, Girls Talk, by Dave Edmunds was playing. She smiled to herself as she recalled the first line of the lyrics: 'There are some things you can't cover up with lipstick and powder' and thought to herself how appropriate the words were given her current situation.
She had just finished fixing her makeup, brushing her hair and freshening her perfume when she heard the front door open and close again. Billy had returned and he was clutching a bottle of Gilby's gin and a bottle of Schweppes tonic water. Sarah got ice from the freezer and Billy poured the drinks.
It was strange sitting on the sofa in her home dressed as she was, talking to a young man she had just had sex with but it was also comforting. They avoided talking about school or about anybody they both knew as that would spoil the fantasy that they were boyfriend and girlfriend and instead they spoke about music, movies and of course Billy spoke about Rugby and in particular his beloved Sharks and their chances of making the quarter finals this year.
Sarah lay along the lounge with her legs across Billy's lap and he lazily stroked them while he talked. They would break now and then to refresh their drinks, light cigarettes and of course to kiss and canoodle. After awhile the conversation becomes stilted and awkward as they ran out of common subjects and the kissing and canoodling sessions became longer as their ardour grew. Billy became more interested in Sarah's legs than their current topic and Sarah stopped talking and lay back enjoyed the feel of Billy's rough hands caressing her stocking-clad legs.
"Can we go into the bedroom?" Billy asked, which caught Sarah by surprise.
"Why?" was the only response that Sarah could muster.
"This couch is kinda small and I wanna cuddle," Billy gave her a bashful smile.
The idea of canoodling on the bed with Billy was intriguing to Sarah. The intimacy of lying together on the covers, of being in her boudoir, the place where she slept, the place where she transformed, the place where she masturbated, was tempting.
Sarah got to her feet and held out her hand and Billy took it and she led him into the bedroom. She'd left the radio on and music played softly in the background. When she went to remove her heels Billy asked her to leave them on.
"They're sexy," he smiled, blushing coyly.
Sarah smiled back at him and climbed on the bed and scootched over to make room for him. Billy stripped down to his underpants, flicked off the light and joined her. It was intimate lying side by side in the gloom, their bodies touching, their breathing expectant above the light background music.
Billy pulled Sarah close and began to kiss her, softly at first, his hands gently caressing her body. Their ardour built slowly and soon their kisses were impassioned, their lips crushed together, their tongues entwined, Billy's hands squeezed her buttocks and Sarah searched for Billy's cock. She freed it from his underpants and stroked it, feeling it engorge and begin to throb in her fingers.
Billy began to circle his fingers on Sarah's bottom, delighting in the feel of her shiny satin panties on his fingertips, he ran a finger up and down the crease between them and Sarah purred like a kitten. He could tell that Sarah liked him playing with her bottom as she squirmed and wriggled against him, her tongue flittering in his mouth. She stroked his cock to full tumescence and toyed with it, not wanting Billy to cum too soon.
Billy started to feel cramped on the narrow bed, despite enjoying every second of what they doing. They both realised that what they were doing was more intimate than what they had been doing in the livingroom. The closeness of their bodies, the tenderness, attending to each other's needs and desires. When Billy used his strength to roll Sarah onto her back and lie on top of her, the communion between them was taken to the next level.
Billy's blue eyes gazed into Sarah's sparkling green eyes and something passed. between them; a silent acknowledgement that this wasn't just lust on their parts, they were entering a relationship. Sarah could no longer pretend that she was just going along with Billy's sexual demands because she was being blackmailed and Billy could no longer pretend that he only saw Sarah as a sex toy. They had feelings for each other.
"Are you okay," Sarah caressed Billy's cheek, and searched his eyes.
"I'm just happy and content is all," Billy smiled down at her.
They kissed, perfectly aware of their bodies pressing together, Sarah entirely cognisant that Billy's hard cock was pressing into her belly. It ignited her passion and the diminutive crossdresser squirmed with delight under the burly football player. Billy was fascinated with the sensation of Sarah's panties and he wanted to feel them on his cock. He adjusted his position so that it nestled in the Vee of her veluntinous panties and began to grind against her.
Sarah purred like a kitten as Billy kissed her passionately while he shimmied his cock against her groin, then suddenly she became aware that her own cock had become fully engorged and was tenting her panties. Billy's cock was rubbing against it, only the layer of silky panty material between the two engorged phalluses. It felt delightfully decadent and wholly immoral for them to be rubbing cocks together but if Billy noticed, he didn't seem to care, instead he kissed her harder and bucked against her fervently, pressing his cock against her velvety mound.
Then something happened that would change their relationship forever.
Billy's cock accidentally slipped inside Sara's panties and slithered between her buttocks.
They both froze and Sarah gazed up into Billy's eyes supplicantly.
"No Billy, we cant... I cant... I'm not ready," Sarah whispered.
Billy could feel the head of his penis nestled in the crevice of Sarah's sphincter. For a fleeting second the idea of what he was about to do might be gay crossed his mind but he was far beyond such tendentiousness now. He would never had done the things he and Sarah had done with each other after only two short meetings a few weeks ago. What was a little buggery in the scheme of things? He had never fucked a woman and was unlikely to anytime soon and he desperately wanted to know what it felt like and, anyway, didn't he think of Sarah as a woman?
In the umbra of the afternoon light peeking through the cracks in the curtains he spotted the jar of Ponds cold cream that Sarah used to remove her makeup sitting on the desk. It was just within reach.
Sarah turned her head to follow Billy's eyes and saw what he was looking at and she anticipated his intentions. Had she herself not used the cool salve to lubricate her cock sometimes when she masturbated?
"No Billy! No!" she whispered.
Billy ignored her and reached for the small pot of moisturiser and scooped a dollop onto his fingers and slid them inside Sarah's panties and lubricated his member.
"No Billy, I'm not doing that!" Sarah began to struggle beneath him.
The bully in Billy returned. He wanted something and he wanted it now and Sarah was not going to stop him. He used his bodyweight and superior strength to hold Sarah still and pushed.
Sarah screamed so loud that it echoed around the vacant rooms in the little cottage as Billy's bulbous glans pierced her tight sphincter. She drummed her fists on Billy's chest and drummed her legs against the covers but to no avail. Billy was inside her.
Billy held Sarah still as best he could and stopped thrusting. Not because he was hurting Sarah but because he was afraid he would climax. The feel of Sarah's tight anus girding his sensitive organ was overwhelmingly pleasureable. Sarah realised that struggling was only making things worse for her. Now that the tip of Billy's cock was inside her, the initial excruciating pain had plateaued to a dull ache. She realised that instead of clamping her sphincter tight she should concentrate on relaxing it.
Billy became aware that Sarah had given up the fight when the tight ring encircling the tip of his penis loosened and Sarah stopped bucking. He looked into her pretty face and saw the consternation and the tears in the corners of her eyes.
"I'm sorry Sarah, I don't know what came over me. I'll take it out," Billy whispered.
"Don't you dare!" Sarah uttered, surprising them both.
"I mean the damage is done now and the worst is over," Sarah said a little bashfully.
A quizzical look crossed Sarah's face.
"It feels good, you dummy," Sarah smiled up at him and wrapped her arms around his back and leaned up and kissed him.
It did feel good. Once the initial sharp spasm subsided and her sphincter loosened, the excruciating pain receded to a dull aching throb. But then the throb became a tingle; a rather delightful tingle. A circlet of sparkling pleasure ringed the entrance to her anus.
"Go slow. Take your time," Sarah broke the kiss long enough to utter.
She clamped her mouth back on Billy's and lifted her legs and locked them around his torso.
Billy gazed lovingly into Sarah's eyes and watched them widen with astonishment and wonder as he slowly slid his thick phallus all the way inside her. She felt it fill her void and it was surprisingly pleasurable, as it slid past her prostate she moaned like a slattern as the feelings intensified. Her cock became fully engorged and pressed against Billy's hard flat tummy. When he began to fuck her his belly rubbed against her panty-shrouded penis and it was all she could do to hold back her climax.
Billy groaned as his cock slid inside Sarah's warm, buttery anus. It was like his cock was being gently squeezed by silken fingers. The deeper he went, the more pleasurable it became and when he was fully inside her with his scrotum pressed against her silken-shrouded buttocks he stopped because he could feel his orgasm about to erupt. He kissed her and she kissed him back and she surprised him when she rubbed her stocking-clad legs against his flanks and dug her heels into his back, encouraging him to fuck her.
He looked into her eyes questioningly and she smiled at him and nodded and clenched and unclenched her sphincter and he knew what she wanted... what they both wanted. He could feel her cock pressing into his belly, the front of her panties saturated with precum. He didn't mind one little bit. He was impressed that he had aroused her so intensely. He wanted to make her come.
His thrusts at first were slow and gentle and they both rode the wave of desire, kissing each other, Billy grabbing her ass and squeezing it as he pummelled her rectum, feeling her anus undulate as her anal pleasure receptors reacted to being massaged by his cock. Her cock juddered in her panties, full, bloated and ready to erupt.
Their kisses became frenetic, their tongues intertwined, their bodies slapping together as Billy began to pound his cock in and out of her tight anus faster and faster.
Sarah felt Billy's cock pulsate and sensed him planting his seed deep inside her. He clung to her, gasping into her mouth, driving her into the bed as his climax peaked. Her own cock erupted and she creamed her panties as waves of delight emanated from her quivering cock and her prostate and little circlets of pleasure radiated from her sphincter. Her anus contracted and quivered, milking Billy of his musky milt.
When the crescendo of their climaxes peaked and waned their kisses became more tender and loving.
Billy lay on top of Sarah, his cock still buried in her anus. She still had her arms and legs locked around him, holding him close, they were both experiencing post-orgasmic bliss. Neither of them wanted to move. They kissed and nuzzled each other saying nothing, conveying their emotions by touch and feel. Sarah gently buffed her legs against his flanks, knowing that he adored the feel of her stockings on his flesh, she stroked his cheek and gently grazed her nails down his back.
Billy sighed and kissed the side of Sarah's mouth, then fully on the lips but the kiss was gentle, their fervour was spent. His cock was till engorged but it was slowly becoming become flaccid. He became aware that Sarah's semen was cooling on his belly. When she had orgasmed at same time as he, the feel of her cock pulsing against his belly disgorging her essence had encouraged him to drive his cock all the way inside her and ejaculate. He was amazed that he had been able to make her orgasm handsfree but now he wanted to wash away her spunk. He wasn't particularly disgusted by it, but now that he was satiated he wanted to clean up. He also wanted a drink and was craving a cigarette.
"I'm going to use your bathroom then I'll make us both a drink while you go," Billy kissed the tip of Sarah's nose and disentangled himself from her embrace.
She watched him walk away, impressed by his muscular frame. She could feel some of his semen dribbling from her sphincter and she clenched it tight. The front of her panties were sodden with her own juices and now she had wet the gusset. She lay still until Billy came out of the bathroom with a towel wrapped around his waist.
"Your turn," Billy called out as he passed by the bedroom door on the way to the loungeroom
Sarah kicked off her heels and padded to the bathroom on stocking feet. She closed the door and looked at herself in the mirror. Her lipstick was smeared around her mouth and her hair was dishevelled. She needed to pee, fix her face, brush her hair and change her panties. Then something suddenly dawned on her.
"Oh my god!" Sarah exclaimed and pulled down her panties and looked in the gusset.
The gusset of her panties was clotted with Billy Barton's semen and the lotion he had used for lube that had escaped her sphincter when Billy withdrew. There was an infinitesimal scintilla of brown. Nothing anyone would notice except perhaps a forensic examiner.
But Sarah knew.
She knew that the hole that Billy had just vigorously fucked was the same hole that she used to defecate. She took her panties off and sniffed the crotch... nothing but Dior, Ponds cold cream and the musky smell of spunk. She wiped her ass and looked carefully at the toilet tissue and saw the same result but this time there was nothing brown. Sarah thanked whatever deity looked after crossdressers that her anus and colon had been empty. Not eating for twenty four hours had paid an unexpected benefit but it was something to consider for future encounters.
She came back to the bedroom and changed her panties, fixed her makeup and brushed her hair. She could hear Billy in the living room mixing drinks and she joined him.
"Well that was unexpected," Sarah took the proffered gin and tonic.
"Are you ok? Did I hurt you?" Billy was genuinely concerned and Sarah appreciated it.
"When do you think you will be ready to go again?" Sarah grinned at him lecherously and plonked herself in his lap.
*****
And so it went until they both matriculated and left school. Sarah had a few months before she started tertiary studies at the University of Sydney. Billy was planning on attend technical college.
Then another fateful day arrived.
Sarah could tell that Billy was anxious when he came over for their usual Saturday tryst. She was feeling particularly horny and ready for sex but she could tell he wanted to talk so after kissing him and giving his penis a welcome tug she made drinks and they sat on the sofa, lit cigarettes and she waited for him to begin.
"Mom's got a job in Melbourne. Fucking Victoria! They don't even play real football down there, just kick-and-giggle Aussie rules," Billy said vehemently.
"She only just dropped the news on me so as you can imagine I'm pissed off. Anyway Sarah, this will be the last time we are together," Billy sighed.
Sarah tried to swallow her bitter disappointment and patted his knee comfortingly.
"Anyway there's more. Steve Rynolds plays lock in my rugby team. You don't know him, he didn't go to our school and now he's an apprentice electrician and he lives at Loftus. Anyway the other day he was bragging to me that he went to Kings Cross last weekend to get on the piss and play up," Billy paused briefly to take a sip of his drink.
"He went to Les Girls and ended up fucking one of the drag queens. It cost him fifty nicker but he told me that it was awesome and that he'd really like to do it again but of course he doesn't want to pay," Sarah nodded understandingly although she had no idea where the story was going.
"He told me this in strictest confidence you understand. Because he had trusted me with his secret I told him about you and what we get up to every Saturday and he was very interested and very jealous," Billy explained and Sarah paled.
She was terrified that someone she didn't know knew her secret.
"Look... he's a good guy and good looking too, all the shielas who come to our footy matches are keen for him. He keeps asking about you, so anyway I was thinking he could take my place. I haven't told him your real name or where you live so don't worry. If your not happy with the idea I'll keep schtum," Billy looked at Sarah earnestly.
Sarah considered the matter, but only briefly. It would mean another person besides Billy knew her secret but she was devastated that Billy was leaving and she would miss her regular Saturday sex sessions.
"Ok, give him my address and tell him to come next Saturday. Tell him to make sure mom and Julie have left and not to knock on the door until thirty minutes after so I can get ready. I don't want him to meet Stefan, just Sarah," she replied.
She could see that Billy was a little jealous and also a little disappointed that Sarah had agreed so quickly which was cute but Sarah was pragmatic. She had gotten used to being adored and she loved the sex, but with Billy on his way out she needed a reliable and discreet replacement.
"Ok, I'll set it up," Billy sighed.
"Also tell him to bring condoms. He's not fucking me bareback until he brings me a doctor's certificate proving he's STD free. If he's been fucking trannies up the Cross, fuck knows what he might have caught," Sarah added.
And so Sarah was set to meet the second man in her life who would become her sex partner. The second of many as it turned out.
Cabin 121 Park Motor Lodge, Engadine NSW, Australia - Present Day
Sarah came out of her reverie. There was nothing in her past that could help her now but she realised that she often found herself in situations where men forced her to do things that she didn't really want to but she always endured and overcame the difficulties. She would need that resolve now because Loyd had climbed off her and left the room, leaving her with Salesi and his two henchmen.
They were all naked and sporting huge erections, looking lustfully at Sarah and muttering amongst themselves. Sarah saw the handcuff key in the hands of one of the men and a glimmer of hope crossed her mind but it was dashed when the man spoke to Salesi.
"Ok, so we uncuff her, turn her around and recuff her so we can spitroast her. I'm going doggie first, Steve gets a bowjob and you get seconds in her ass after I've finished," the man spoke about Sarah like she was a slab of flesh not a person with feelings.
"Agreed, now uncuff her and get her on her hands and knees, I wanna fuck her today not tomorrow," Salesi chuckled.
Sarah prepared herself as best she could for what was coming next.
To be continued
Cabin 121 Park Motor Lodge, Engadine NSW, Australia
The man approached the bed jiggling the handcuff keys, holding them in front of Sarah’s face to taunt her. She had overheard the conversation between Salesi and the other two men and she knew that there was no salvation in those handcuff keys.
The man looked down at Sarah lying on the bed, her arms outstretched above her head, handcuffed to the bedhead. She might be forty, she might be fifty; the heavy makeup made it difficult to tell her age and everybody lied in their Grindr profiles. She was pretty, even with her makeup smeared and her raven black hair mussed. Her blouse was open and untucked revealing her ‘man-boobs’, her belly was flat and hairless. Of course Gary knew that Sarah was a crossdresser and that her hair was a wig but she could pass as a woman except for when you looked further down her body.
Sarah’s navy blue pencil skirt had been hiked up by Loyd so he could fuck her, exposing the black satin garter belt with red lace trim and her matching panties. The illusion that she was a woman was foiled by the flaccid penis bulging her semen sodden panties.
“Hey Steve, Salesi, the bitch creamed her panties when Loyd fucked her,” Gary sniggered.
“I told you Gary, this bitch likes it rough. She got a semi on when she was sucking my cock,” Salesi replied and ran his hand along her leg.
“I love these fully-fashioned stockings. This bitch can be my secretary any day of the week,” Salesi chuckled and squeezed her thigh.
So now Sarah had all of their names: Loyd, whom she had met on Grindr and who had lured her to the motel, Salesi, the big Islander who had fucked her mouth first, Gary, the guy with the handcuff keys and Steve, the balding fat older guy.
“Ok, I'm going to uncuff you and give you a minute to work some circulation into your wrists, then you're going to kneel on the bed and I'm going to cuff you again. Don't fight us, don't try to get off the bed, just do as you're told and we won't have to get handsy with you,” Gary barked.
Sarah was just happy that she was going to be free of the cuffs for a while. Her arms were aching and her wrists were burning. Gary uncuffed one wrist, then the other and Sarah sighed with relief and rubbed her wrists, wincing when full circulation brought momentary pain but then relief. She smoothed her skirt tugging the hem down so that at least for a while she had a modicum of decorum. She also buttoned her blouse.
“Ok, enough faffing, get on your knees girly,” Gary barked and dangled the cuffs in front of her face whilst smiling wickedly.
There was no escape so Sarah obeyed and got on her knees athwart the middle of the bed and held out her wrists and experienced a small moment of triumph when Gary cuffed her wrists in front of her body rather than behind her back.
That moment was short-lived however when Gary pushed her down so that she was resting on her hands and knees. Gary climbed on the bed and took up position behind Sarah and Steve stood on the floor facing her, his cock directly in front of her face. Salesi stood at the bottom of the bed looking on and Sarah could see that he had his phone in his hands, the camera facing the bed. He was obviously going to film her being spit roasted.
Steve lifted Sarah up by her armpits so that her face was level with his and began to kiss her, thrusting his tongue into her mouth. Thankfully his breath was fresh and Sarah endured his advances. To be honest he was a good kisser and Sarah returned the kiss, slipping her tongue into his mouth. Steve took her handcuffed hands and placed them in his groin. His semi-hard cock responded when she grasped it awkwardly and stroked it. It was long and sleek but not too girthy, which was just as well because Sarah knew where it was going next.
She felt Gary slide his hands under her skirt and his fingers gently stroked her thighs. He fondled the dark welts of her stocking-tops and then he traced the backseam of her nylons from thigh to ankle and little freshets of delectation proliferated along her legs. Steve kissed her passionately and she felt his cock fully engorge and she wondered briefly if she might be able to bring him off in her hand and save herself the indignity of having to suck his cock. Then she felt Gary lift her skirt and nestle his steely member in the crevice between her buttocks and slide it up and down her cum-soaked panties.
It wasn’t unpleasant and in different circumstances she would have welcomed the attention of the two men. She returned Steve’s kisses with feigned ardour and stroked his cock a little faster and his breathing became laboured, little grunts escaping his lips and wheezing into her mouth. His belly got in the way of her handcuffed wrists and she could feel the steel of the encircling restraints abrading his soft flesh. It must have been irritating because Steve slapped her hand away from his groin or maybe he was close to cumming and had ascertained her plan to bring him off in her hand.
It was as if a telepathic message passed between the two men because Gary pressed on Sarah’s shoulders, forcing her back down on her hands and knees.
Steve lifted his overhanging gut out of the way and pulled Sarah’s face into his groin and pressed his cock against her mouth. At the same time Gary eased aside Sarah’s panties and nestled the head of his phallus into her puckered bud. Gary gripped her hips and thrust. His cock slid into her anus like a hot knife through soft butter, Steve's semen and the remaining lubricant easing the passage of his engorged rod.
Sarah felt Gary's glans distend her sphincter and his shaft glide past the tight ring and begin to fill her void. It seemed like Gary's cock was as long and as thick as a truncheon as it slid deeper and deeper inside her until finally she felt his groin press against her panty-clad buttocks, his scrotum swinging back and forth against her taint. She opened her mouth to squeal and Steve took advantage and pushed his cock into her mouth, stifling her cry of anguish.
“There’s a good girl. Just relax and take daddy's cock,” Gary's voice was almost soothing.
Sarah’s face was pressed against Steve's fat belly with half of his lengthy appendage in her mouth. Steve seemed happy to just stand there with his cock in Sarah’s mouth, his hands resting lightly on her head and let her nurture his cock with her mouth, which suited her. She would likely choke if he pushed the whole thing in there. Bent over as she was, she needed to rest her upper bodyweight on her hands so she was unable to cup Steve's scrotum so she concentrated on working her lips on the shaft of his penis and her tongue on his bulbous glans. It was easy work for her.
What wasn't easy was taking Gary's cock in her ass. It was huge! Luckily for Sarah, Gary stopped thrusting when he had his phallus fully inside her. She kept still and concentrated on relaxing her anal sheath and sphincter until she comfortably accommodated the mighty organ while she slathered at Steve's penis. He started the annoying habit that some men liked to do which was to rip his cock out of her mouth and bounce it on her nose and cheeks whilst pushing her mouth onto his scrotal sac.
Sarah paid homage to him however, licking the hairy ball-bag and then sucking it into her mouth and using her tongue to slather his testes, which Steve seemed to like, at least for a little while before he shoved his prick back in her mouth.
At the other end of her body, Gary had rested long enough and staved off a premature orgasm and was ready to fuck her. He slapped her ass a couple of times, gripped her hips a little tighter, and began to plunge his cock slowly in and out of her tight hole, watching intently as his cock systematically see-sawed her puckered bud. He removed his hands from her hips and gripped her thighs, pulling Sarah’s plump ass into his groin and ground his pubis into her and Sarah, now comfortably adjusted to his long girthy manhood, obligingly pushed back.
“You love it don’t you, you slut!” Gary grunted as he worked her ass, stroking her nylon-sheathed legs.
“Suck my cock you whore!” Steve decided be needed to be verbal too as he held Sarah’s face in his hands and forced his cock in and out of her mouth.
They were role-playing for the camera but both men were enjoying ravishing the attractive crossdresser.
“This is going to look awesome when I upload it,” Salesi worked his phone’s camera as if he was a Hollywood director, zooming in and panning out on the action.
Despite her discomfort, Gary's cock was fulfilling its duty as an instrument of pleasure, lighting up the pleasure centres in Sarah's rectum and her sphincter, which gripped Gary's rod as he drove it in and out of her. Her prostate was a fiery ball of sensuality, radiating waves of carnal delight.
She instinctively clenched and unclenched her rectal muscles, gripping and releasing Gary’s cock as he began to fuck her harder and faster. Her sphincter contracted and released around his invading member and Gary struggled not to climax as her velutinous channel undulated and quivered as Sarah worked her ass like a craftsman, providing maximum pleasure for both of them.
It was not the first time that Sarah had been spit roasted, far from it, and she always found it a little difficult ensuring that the men at both ends of her body received the same attention. Now that she had her ass providing Gary with maximum pleasure, she worked her lips and tongue on Steve's long sleek rod, circling the corona of his glans with her tongue while her lips slid up and down the shaft. She felt the veins begin to pulse animatedly and the shaft begin to quiver and she smiled around the appendage filling her mouth; she knew that Steve was close to extremis. He gripped her head and fucked her mouth, his eyes closed in paroxysm of pleasure.
“Oh fuck, I'm coming!” Steve cried and gripped Sarah's head in his hands and shot his first spritz of jism in her mouth.
Sarah slavered at Steve's cock, lapping his sensitive glans with her tongue and felt it erupt again, the second burst of milky ejaculate filling her mouth forcing her to swallow it as Steve's cock continued to plunder her mouth.
Gary watched his friend fucking Sarah’s mouth, listening to the sucking, slurping sounds as Sarah expertly fellated Steve and to the ‘thwok’ ‘thwok’ ‘thwok’ sounds of his pubis slamming into Sarah’s buttocks, her fine derrière grinding against him, gyrating to maximise his and her pleasure.
When Steve drove his cock as far as he could into Sarah’s willing mouth, pulling her face into his fat belly she almost suffocated and she bucked and writhed on all fours as she struggled to breathe. Steve misread her discomfort for an expression of carnal pleasure and held her face into his belly and ejaculated into her mouth. Steve's spunked a torrent of viscous ejaculate into Sarah’s mouth, forcing her to swallow it, further hindering her fight to breathe.
“I'm coming! I'm coming! Fuck me this is awesome! I've never cum this much in my life,” Steve squealed.
Sarah’s mouth filled with another freshet of musky semen which she struggled to swallow so she could breathe.
Watching all this triggered Gary’s climax and he dug his fingers into Sarah's thighs, pulling her rounded ass tightly against his groin as he drove his cock all the way inside her and unleashed his issue deep inside her rectum.
“Fuck! Me too!” Gary pulled Sarah's cushiony buttocks into his groin and slammed his cock deep inside her and began to inseminate her.
The sensation of having her mouth raped, swallowing Steve's milky, salty issue, while Gary's cock quivered inside her asshole, blasting her full of spunk, his glans pressing on her prostate, his shaft fretting her sphincter, triggered Sarah's orgasm. For the second time that evening she spunked her knickers. She sucked gregariously on Steve's cock and ground her buttocks into Gary's pubis to elicit as much pleasure as possible for all three participants.
“This is fucking amazing guys! Steve, spunk on her face!” Salesi was taking his directorial duties seriously as he zoomed in for close-up, just in time to catch Steve whip his cock out of Sarah's mouth and spray the remainder of his ejaculate over her eyes, nose, lips and hair.
Clots of his glutinous issue ran down her face and glistened in her raven hair. Sarah took a mighty breath and moaned like a slattern as she ground her ass into Steve's groin, eliciting as much pleasure as she could as his cock quivered and disgorged his load deep in her anus.
Salesi caught the whole thing on camera, including Steve rubbing his cock on Sarah’s face, smearing her makeup with his issue, whilst Sarah desperately licked the creamy goo off her lips, her eyes glazed with lust, and then Gary pulling his cock from her tight hole, spraying the last of his issue on her panty-shrouded ass cheeks. It would make an epic porn film.
Salesi was frantically wanking his cock with one hand whilst filming with the other. The show that Sarah was putting on was so outrageously erotic and when Gary finished ejaculating Salesi dropped his phone on the bed, pushed Gary out the way and slammed his cock into Sarah’s semen-clotted hole.
Sarah collapsed under Salesi’s weight, her body pressed firmly into the mattress as Salesi raped her asshole. He thrust once, twice, three times and was done. He roared with anguished euphoria as his cock undulated inside Sarah's battered anus and discharged his hot load. Sarah lay underneath him, totally exhausted and unable to move. Salesi ground his cock into Sarah's ass a few times to release the last of his issue and then rolled off her.
“Did you guys enjoy yourselves?” Loyd stood in the doorway, he'd been watching the show for the last few minutes.
“You promised us a good looking, juicy piece of ass Loyd, and you didn’t let us down,” Gary slapped Sarah on Sarah’s bottom.
Gary's semen was congealing on her panties and the tops of her stockings, Salesi’s jism dribbled from her distended asshole, her face was caked with Steve's spunk and freshets of it glistened in her jet-black hair.
“Well let's get a drink and have a smoke while she gets some rest before we go at her again, shall we?” Gary led the four men out of the bedroom, turning off the light before he closed and locked the door.
Sarah lay face down on the bed, cum-spattered and dog-tired. She curled up in a ball and her mind once again drifted back to the past.
Kings Cross, Sydney Australia - 1981
Sarah grunted and opened her legs a little wider so she could keep her balance in her ridiculously high heels. She was pressed against the brick wall outside the toilet block just down from Fitzroy Gardens. Her sequined minidress was hiked up, her pantyhose and panties rolled down to her knees and a fifty-something suburbanite visiting ‘The Cross’ to experience Sydney’s premier red light district was buggering her.
“Hurry up love, I haven’t got all night,” Sarah whined.
She had been making her way home from the Goldfish Bowl when the man had accosted her and offered her twenty dollars for a ‘knee trembler’. Sarah was drunk and a little high and had already had sex with three different men over the course of the evening but the promise of quick cash was an offer she couldn't refuse. Her makeup was smeared, her hair a mess, her nylons laddered and she was walking precariously on her heels, zigzagging her way home when the drunken reveller solicited her.
“Shut up you tranny bitch!” the man gripped her hips and jackhammered his cock in and out of her anus.
He was drunk and horny but couldn't quite get there. Sarah slipped a hand between her legs and found his scrotum and fondled the hairy sac expertly and that did the trick. The man pulled her ass into his groin and ground against her, depositing his load deep inside her anus.
As soon as he finished climaxing the stranger whipped his cock from her ass and stuffed it in his pants. He dropped a twenty dollar note on the ground between Sarah's legs and staggered away looking for a taxi. Sarah picked up the money before she even bothered pulling up her underwear. Pickpockets and thieves were rampant in this part of town. She shoved the money in her purse, rolled up her pantyhose and pulled up her flimsy pink transparent knickers and continued on her way, lighting an Alpine with her Bic as she tottered home.
Kings Cross was full of bars and clubs during this period and many trans women worked in them. The Rex Hotel, Tina’s Bar, The Venus Room and the Bourbon and Beefsteak were popular social spots and fertile ground for picking up trade.
Unbeknown to the punters, many of the strip clubs employed trans girls who were often better at the art of striptease than their female co-workers. These places were a drawcard for straight males looking to try something exotic and good looking, passable, transgender women and transvestite men could earn quite a decent stipend. A large group of working girls operated around Darley Street in Darlinghurst because the laws of the day allowed street soliciting and the traffic often backed up in William Street on a Saturday night as punters crawled the curb.
The tranny prostitutes worked an area called ‘The Wall’ and could be seen hopping in and out of cars or disappearing into dark alleyways with their punters.
Sarah did not consider herself a prostitute. Most nights she frequented the Goldfish Bowl where she was invariably hit on. If she liked the man she would go back with him to his hotel room or they would skip across the road to the Pleasure Chest, an adult store that had a XXX cinema, gloryholes and private cubicles out back.
The very first time she had been hit on Sarah was an ingenue, new to the bright lights of Sydney and out for the first time dressed en-femme. She had stumbled into the Goldfish Bowl to escape the taunts, catcalls and groping hands of the men on the busy streets who thought a pretty young girl in a short skirt was fair game.
She had made love with the man in his room in the Crest Hotel, right above the venue, and was stupidly disappointed when he tossed a twenty on the bed on his way to the bathroom and asked her to be gone before he came out. She caught a taxi back to the student accommodation at the University of Sydney and snuck into her room at four in the morning reeling from the experience.
Her foray into Kings Cross came about not long after she graduated high school and went to university. Her first lover Billy Barton had left for Melbourne but had recommended that his friend Steve Reynolds take Billy’s place.
Steve Rynolds had turned out to be more than an adequate replacement for Billy Barton. Steve was more mature, more experienced and a very enthusiastic lover who adored Sarah and taught her things in the bedroom that she never dreamed were possible. After matriculating near the top of his class, Stefan enjoyed a couple of months of freedom spending as much time as possible transformed as Sarah. Steve had his own place, only one train station down the line, and Stefan would arrive at Steve's place with a backpack full of feminine requisites and go straight into the spare bedroom and emerge as Sarah and they would fuck the afternoon and evening away.
When Stefan left Sutherland to attend the University of Sydney, accommodated in the student digs, he took all of Sarah’s accoutrements with him. Sarah emerged from her cocoon, assured of anonymity in the big city and gravitated naturally to Kings Cross where her type were not only accepted, they were welcome.
After her indoctrination into the world of sin on her first night at the Goldfish Bowl, Sarah realised that she was potentially onto a good thing. She didn’t openly prostitute herself but if the men she met who craved company were willing to drop some money for her services, who was she to say no? It wasn’t like she was selling her ass on the street or working the clubs and bars owned and operated by the likes of Abe Saffron, the so called King of the Cross.
After three months she had saved enough money to move out of the student gigs and rent a bedsit apartment on Ward Avenue, one street removed from ‘the strip’ as Darlinghurst Road was known. She put together an extensive wardrobe and hung out in various clubs and pubs that welcomed her kind, invariably ending up at the Goldfish Bowl. As a young, attractive, passable twenty year old transvestite, new on the scene, she was very popular.
At first Stefan allowed Sarah to take control of his psyche after classes during the week and on weekends but Sarah soon became addicted to the lifestyle: the booze, the drugs, the adoration of men, and of course, the sex. Her grades started slipping when she began to skip lectures, miss assignment deadlines and seldom studied. She was spiralling out of control and Stefan was powerless to stop her.
Sarah became a fixture at the Cross’s most popular nightspots. She was on first name basis with the bartenders, bouncers, doormen, touts and hustlers. She was good for business as wide-eyed schmucks from the suburbs out for a night in ‘sin city’ sidled up to her, buying overpriced drinks and spending big. She was careful never to pick up men except at the Goldfish Bowl, which was considered neutral territory by the pimps and crooks. She befriended a detective from the notoriously corrupt Darlinghurst police station, fucking him on a steady basis in return for being left alone by the licencing squad and beat coppers.
She rubbed shoulders with some of the transgender women who worked at Les Girls and for a time contemplated whether or not that she too might be gender dysphoric (a term not yet in common use) but decided that she wasn’t, she just loved the life she was living but it would all come to an abrupt halt.
Barely scraping through the first year at university, living as Sarah when he wasn't attending campus, Stefan was perilously close to spiralling out of control when fate intervened. She was nearly home at 4am on Sunday morning when the two men accosted her. Sarah had been taking speed to get her through a day and night of debauchery and to fight the effects of the alcohol she had imbibed and was coming down with a crash, almost dead on her feet. One man came up behind her and put a handkerchief soaked in a liquid sedative over her face and Sarah passed out without feeling a thing. Between them they carried Sarah to her flat. Anyone seeing them would think it was two friends helping a drunk girl home.
Earlier in the evening her detective friend had taken Sarah upstairs for a quick shag in the room that the owners of the Crest comped him and had advised her that Abe Saffron had his flunkies were out reigning havoc on dealers, hustlers and working girls who were working his patch and not paying him a stipend and warned her to careful. She had just shrugged off the advice, stating that although she liked to visit most of the bars and clubs on the strip, she only pulled guys in the Goldfish Bowl, which wasn't owned by Abe or any of his associates.
She regained consciousness in her bedsit finding that she was handcuffed, her arms extended above her, the cuffs suspended from a makeshift strop constructed from a pair of her tights that were secured to an ornamental ceiling beam. Her stockinged feet barely touched the floor. Her fuck-me heels had been removed by one of the henchman.
“Those things can be a deadly weapon. Mick Freeman got stabbed in the eye by a high heel one night when he was dealing with a prossie who was holding out on him. Of course he beat the bitch senseless but he nearly lost the eye,” the henchman said as he ripped off Sarah’s heels and tossed them aside.
“What the fuck?” Sarah groaned when she realised her predicament.
“You know who we are?” the dark haired older of the two men growled.
Sarah had seen the two men prowling the strip on many occasions, meandering from club to club ensuring the owners and operators were abiding by Abe’s mandates and kicking up the proper stipends.
Sarah nodded but said nothing. She was suddenly sober and instantly terrified.
“Just so there's no confusion, we are the personification of Abe’s retribution and you've been a naughty girl,” the younger, sandy-haired man explained, rather needlessly.
“I've never worked any of Mister Saffron’s establishments. Sure, I hang out in them sometimes but I never pull in them,” Sarah reasoned.
“That may well be but you're still taking food off his table. Every punter you pull in the Goldfish Bowl is a punter who might have gone with one of our girls. Also you often use the Pleasure Chest to service your punters and that is Abe's establishment. You should have been working for Abe from the start or at least been kicking up to him,” the dark haired man said grimly.
“I didn’t know; honestly I didn’t,” Sarah pleaded.
“Doesn't matter. You've been here long enough to figure it out. That copper you've been fucking should have explained the rules to you better, he's been taking kickbacks from us since he was walking the beat,” sandy-hair explained.
Sarah thought they were playing a Mutt and Jeff on her, taking turns to threaten her.
“Now, you can get stabbed with this...” Dark Hair produced an evil looking flick-knife.
“Or this...” he unzipped his fly and released his engorged member.
It was a no-brainer for Sarah, whose arms were aching and was shaking with fear when she saw the knife. She looked down at the dark haired man's groin and nodded her head vigorously.
“I thought so, you slut,” Dark Hair kicked off his boots, dropped trou and pulled down his underpants so that he was naked from the waist down.
Dark Hair approached Sarah who was hanging from her wrists like a side of beef and studied her. She was wearing a red satin evening gown that was low cut and clung to her lean body like a sheath. Underneath she wore a red satin and lace bra with ‘chicken fillet’ inserts to give the appearance of small tits. She wore lustrous fleshtone sheer-to-the-waist pantyhose but no panties so that there was no VPL to spoil the silhouette of the tight sheath. Her makeup was heavy and she wore her signature Bettie Page wig.
The man still had the knife in his hand and he waved it in front of her face menacingly and grinned evilly. A miasma of body odour thinly veiled in cheap cologne emanated from his slender but muscular body. He placed the tip of the knife just below Sarah’s left eye and spoke, his breath fetid with cigarettes and whisky.
“Don’t bite. Don’t kick. Don’t do anything stupid or you might lose an eye,” he hissed and ran the flat of the blade down her cheek.
Sarah was too scared to speak and she couldn’t nod because the tip of the knife was pressed into her throat but her eyes said everything that needed to be said. The thug ran the flat of the blade down her body until the point rested between her legs. It sliced through the satin dress, the fabric hissing as he slit it from crotch to toe.
He spun her around like an ornament hanging from a branch and opened the gown and took a second to admire her long legs sheathed in the glossy hosiery.
“No knickers; you are a naughty girl,” he chuckled and slipped the knife between her legs.
Sarah had mastered the art of tucking. Her testes were ruched up inside her inguinal canals, her empty scrotum and penis held in place along her perineum by the tight fitting pantyhose.
“She's got a great arse,” he commented to his friend as he traced the knife down the crease of her buttocks.
He pressed the knife into the sheer fabric and Sarah felt the nylon rend and a small hole was created adjacent to her puckered bud. The man poked a finger through the hole in her pantyhose and slid it inside her. Her sphincter instinctively tightened around the invading digit but the man worked his finger deeper into her anus.
“Tight too,” he whispered in her ear, then nibbled her earlobe.
He licked her neck, pressing his groin into her buttocks while his finger wriggled around inside her, stroking the walls of her anus and kneading her prostate. Sarah had been fucked three times already that night and the remnants of semen and KY jelly provided sufficient lubricant to ease the passage of the invading digit. In any other circumstances what the man was doing to her would feel wonderful. Sarah had not climaxed that evening, the speed and the booze had caused ‘brewer's droop’ but now that she had been terrified into sobriety her receptors were hypersensitive.
He licked her neck while he ground his cock against her buttock and fingered her rectum. She sensed that the man was well-equipped as he humped her nylon-shrouded haunch.
“Jeeze, those nylons feel good on my cock,” he whispered again in her ear and she heard the knife clatter on the floor as he dropped it.
“Remember, no biting. I can pick that knife up in a second,” he hissed and ripped his finger from Sarah’s anus and spun her around like a carcass on a meat hook.
He hefted her thighs and opened them, forcing Sarah to lock her legs around his waist to support her weight as his mouth closed in on hers. He crushed his lips against hers and slivered his tongue into her mouth as his hard phallus probed her sphincter.
Sarah could do nothing but hold onto the man with her thighs as his tongue swirled in her mouth and his cock slithered against her pink crinkled butthole. The man smiled around the kiss. She sensed the evil in him, the stink of his body, his putrid breath, his sinewy body pressing against her. He was scrunching her bottom and stroking her thighs, her pantyhose hissing as his calloused fingers fondled and caressed the silky fabric; he seemed fascinated by the lustrous hosiery. The glans of his penis, now wet with the secretions leaking from her anus continued to fret against her sphincter.
The man could easily have slid his turgid member inside her but he continued to tease himself, feeling her pantyhose rub against his shaft while his glans scoured her tight entrance, his kisses deep, enthusiastic and demanding. Sarah clung to him with her thighs and calves, convincing herself she was doing so only to prevent catastrophe. She returned his kisses, only so that her sweet spittle would nullify his fetid breath. She wriggled her buttocks and clamped her legs tightly around his waist, only so she wouldn't fall and be left dangling with all her weight on her wrists. All this she believed was true, despite the longing she felt, despite the delight she felt as their tongues intertwined, despite the deep languid ache she felt in her prostate from where he had fingered her, despite the overwhelming urge she felt to impale herself on his steely rod and despite her hard cock, which had sprung free from between her legs, tenting her pantyhose.
He slowly slid his cock inside her and Sarah moaned as his bulbous knob opened her sphincter and his thick shaft snaked its way inside her tight passage, stretching it, igniting the pleasure sensors, filling her until his rampant organ was all the way inside her. He kissed her deeply, exploring her mouth with his tongue, sliding his hands up and down her thighs, her diaphanous nylons tingled against her freshly-shaved legs, releasing another freshet of delight. Then he cupped her silken-sheathed buttocks and began to fuck her.
But... Dark Hair fucked her slowly, easing his cock almost all of the way out of her and then slowly gliding it back in while he kissed her passionately, kneading her buttocks, stroking her thighs. Sarah hated him for it. Sarah loved him for it. For all intents and purposes she was being raped but her body betrayed her. The funk of his body odour should have revolted her, the taste of his mouth on hers should have sickened her, his gnarled penis inside her should have appalled her, the feel of his sinewy body pressed against hers should have repulsed her but instead she moaned like a whore and clung to him with her legs wrapped around him, shaking with desire and wantonness.
Sarah was close to orgasm and she tried to fight it off, thinking of the knife that had been held to her face, thinking of the threats the man had made, thinking of dead kittens, thinking of anything that would quell her desire. But Dark Hair kept kissing her, his penis kept sliding slowly in and out of her tight, slick hole, his hands caressed her thighs and scrunched her buttocks, his scrotum bounced off her taint. He must have known that Sarah was relishing being defiled. She could sense the smirk on his lips as he kissed her, his breathing was becoming erratic and she sensed that he too was close to extremis.
But that cock just kept a steady rhythm, sliding slowly in and out of her rectum lighting up the pleasure centres in her anus, her prostate and her sphincter. His hands on her thighs and buttocks, stroking her and caressing her nylons, the sensation of the diaphanous hosiery on her flesh adding to fuel to the fire of lust, drove her closer to the edge.
Suddenly, after what seemed like an eternity, he pulled her close and drove his steely phallus all the way inside her and held her tight. He drove his tongue deep in her mouth and she felt his whole body shudder and his cock quiver, triggering her rectal muscles to spasm as his hot load began to erupt from his pulsating penis . He dug his fingers into her buttocks and she locked her legs around him tighter and ejaculated, saturating the gusset of her pantyhose with her milky essences as Dark Hair flooded her back passage with his glutinous semen.
Her orgasm was overwhelming and she mewled, shook and convulsed with the intensity of it but Dark Hair held her tight against his sinewy body, kissing her, inseminating her.
Sarah came down slowly from her orgasmic high and became aware that her wrists were chafed and aching, her armpits were burning from the burden of her outstretched arms but her cock and her anus were still tingling from the overpowering climax.
“You're not bad. You should have started working for us when you first came to the Cross,” Dark hair kissed her one last time and then withdrew his cock from her asshole and let go of her legs.
Sarah yelped as the full weight of her body came onto her wrists and she struggled to find purchase on the carpeted floor with her feet to take the burden off her arms.
“I'm not a prossie! If I like a guy I go with him! If he gives me money I take it!” Sarah knew that she sounded pathetic even as she uttered the words.
The men ignored her.
“Your turn,” Dark Hair said to his sandy haired colleague matter-of-factly, ignoring her pleas.
Sandy Hair looked at Sarah, her sliced open sheath dress displaying the cum-soaked front of her pantyhose with her shrivelling penis inside them.
“I'm having nothing to do with that,” he pointed at her spermy crotch and Sarah stupidly thought the ordeal was over.
Sandy Hair spun Sarah around like a swizzle stick so that her back was to him and he unceremoniously gripped her hips and slammed his rampant pecker in her keister.
This time the fucking was hard and brutal. There wasn't a skerrick of tenderness as Sandy Hair raped her asshole and to Sarah’s disgust it felt just as good, if not better. The brutality juxtaposed to the tenderness like sweet was to sour... totally opposite but each delicious in their own way.
It was over quickly, Sandy Hair pulling her ass had into his groin when he ejaculated deep inside her. He ripped his cock from her battered anus as soon as he was done and runnels of semen ran down Sarah's thighs, gobbets of spermatozoa clinging to her nylons. She was erect but didn’t climax this time.
“Ok. I think you've got the message. You work for us or get out of the Cross. Come find me when you’re felling better and I'll sort a pimp out to run you,” Dark Hair uttered as his friend pulled up his pants and zipped his fly.
They both made as if to leave and Sarah was terrified that she was going to be left hanging from the ceiling.
“Oh, I forgot the rest of the message,” Dark Hair grinned at her evilly.
The thrust was so quick and the knife so sharp that Sarah didn’t feel it at first. First she felt the freshet of warm blood running down her side, then she felt the sting where the knife had entered the fleshy part of her hip.
Dark Hair reached up and cut the tights that were secured to the ceiling beam and Sara dropped to the floor and curled up in a ball of agony while Dark Hair unceremoniously removed the cuffs. He looked down at Sarah lying on the floor sobbing, blood seeping from the wound in her side and poked her with the toe of his boot.
“Like I said, come see us when you’re feeling better,” he sniggered and the two men left, leaving the door wide open.
Twenty Years Later
Stefan Lang looked in the mirror and saw Sarah looking back at him for the first time in twenty years. It was an older version of Sarah and her once youthful prettiness had mellowed into mature beauty. She was even wearing the same Bettie Page wig. The wig had been stored in the attic, neglected for two decades.
After the stabbing, Sarah had been found by a neighbour and taken to Saint Vincent's Hospital. Lucky for her Dark Hair had no intention of killing her, the stabbing had been a warning.
Stefan’s mother arrived at the hospital later in the day and in a very distressed state told her son that she had warned him that no good would come from living in Kings Cross. Stefan had pleaded with the doctor and the nurses not to tell his mother that he had arrived at the hospital dressed as a girl. He had told the police that he had been attacked during a break in and had no idea who the perpetrators were and the constable from Darlinghurst police station had no interest in investigating the case further, especially since said constable was already on the take and knew exactly who the perpetrators were. The case was closed before it was opened.
When he was released from hospital Stefan had purged, throwing away everything of Sarah’s but he just couldn't part with the Bettie Page wig and he hid it away. He moved back into student digs, worked hard at making his grades, never missed a lecture, was never late for an assignment and finished university with his degree. He met a pretty girl, married her and settled down to life in the suburbs. Only in his dreams did he think of Sarah but he never let her out of her ‘mind prison’. He knew that it would be too dangerous because once free, he would be unlikely be able to control her and the thought of being discovered as a crossdresser was terrifying because he loved his family and didn’t want to hurt them.
That changed when his kids married and moved interstate. By then the bloom of love and desire that he had shared with his wife had withered on the vine. Despite his pleas to liven up their sex life, his wife Christine, showed no interest and lifted her drab cotton nightgown about once a week and lay still while Stefan rutted away on top of her until he achieved an unsatisfactory climax.
Stefan started to look at crossdresser porn online while he masturbated and dreamed that he was the ‘girl’ in the videos. He began to have nocturnal emissions dreaming about Dark Hair fucking Sarah while she was handcuffed to the ceiling beam. Sarah tried in vain to emerge from her mind prison but Stefan kept her securely locked away.
Then one day Stefan came home early to find Christine being rigorously fucked by his so-called best friend. He didn't know if he was more angry about the cuckold being his mate or Christine’s obvious enthusiasm while she was being vigorously rogered by his best friend or the fact that she was wearing sexy red lingerie, stockings and heels. When he’d brought up the subject of her acquiring some lingerie to liven up their sex life she'd scoffed at the idea.
Christine ran away to the Gold Coast with his ex best friend and filed for divorce. The kids and friends he and Christine shared took her side and Stefan found himself single and living alone and Sarah slipped into his psyche and told him that he no longer had recourse to keep her imprisoned.
But... as keen as Stefan was to rekindle his desire to let Sarah run free, many years had passed and things had changed. Young people especially were no longer trapped in a society that thought about gender in the binary. Many transgender women openly discussed their journey, others were open about their gender fluidity. There was this wonderful thing called the internet and everyone had mobile phones. People were hooking up everywhere because it was so easy to do so online and there were even licensed sex-on-premises venues that catered to their need to have somewhere clean, safe and discreet to meet.
Sarah was lucky that she had ceased being promiscuous before the AIDs pandemic erupted and had luckily evaded contracting an STI. Now there was PrEP and free clinics where one could get discreetly and regularly tested.
There were also other considerations. Would Sarah still look attractive and femme? Had too much time passed?
Sitting in front of that mirror, her heavily made-up face framed by those gorgeous raven locks, Stefan decided that he could indeed let Sarah out of her cage, but there was still a lot to do before he did so. He made a shopping list: lingerie, hosiery, shoes, skirts, blouses, dresses, makeup, a new wig or two and of course a douche. He also invested in a pair of good quality breastforms and some silicone ‘chicken-fillet’ inserts.
Shopping for Sarah was fun. Stefan felt no embarrassment this time procuring the required female requisites. It was exciting and Stefan took his time putting a wardrobe together matching clothing styles with looks he wanted Sarah to project. His favourite was sexy secretary. Now that Sarah had matured so had her sense of style. There was manscaping to done too, eyebrows to be shaped, body hair to be removed especially that now the fashion was to present with a shaved pubis, so that needed attending to. He let his nails grow longer and kept them manicured.
Stefan looked at the bed where Sarah’s new clothes were laid out, the stockings and pantyhose still in their cellophane wrappers, the panties multicoloured; mostly full-cut or boy-leg because thongs were for teenagers and twentysomethings, all either nylon, satin or lycra… no cotton of course. On the floor beside the bed were three pairs of high heels: black, red and white. On the dressing table, that had once been Christine’s, were three wigstands with three wigs, Sarah’s first and favourite Bettie Page, a brunette wavy shoulder-length mane and a platinum blonde bob. A selection of makeup that a drag queen would have been proud of was laid out ready for use.
Only when he was fully prepared would Stefan allow Sarah out of her ‘mind prison’. He surveyed the trappings laid out on the bed and hanging in what had been Christine’s side of the wardrobe, the wigs, the makeup and the heels and decided it was time.
He let Sarah out of her cage.
Her psyche flooded his brain and appropriated his senses and motor skills. Sarah looked around the bedroom and was delighted with what she saw. Stefan’s mannerisms changed in an instant: he became lighter on his feet and his gait became feminine, his gestures effete, his voice a sexy smoky rasp, similar to Kathleen Turner’s, her younger girly shrill no longer appropriate for a woman her age.
Sarah disrobed and kicked the cotton shave-coat that Stefan had been wearing under the bed with distain. She unwrapped a pair of taupe sheer-to-the-waist pantyhose and caressed the diaphanous garment with her fingertips then she fingered a pair of black satin panties. She sat on the bed and luxuriated in the feel of the pantyhose sliding up her freshly-shaved legs, uttering a little gasp as she pulled the fabric tight around her buttocks and genitals. Then she glided the panties up her legs and snatched them tight. She was tucked and when she looked in the mirror she saw a perfect Vee between her legs. She put on the brassiere that matched the panties and slipped the chicken fillet breast-enhancers into the cups.
Her dormant makeup skills had not diminished and she sat at the dresser and painted her face and was impressed with the results. They were far better than the effort that Stefan had done when he’d used the makeup that Christine had left behind to see if Sarah was worthy of resurrection. The wigs had all been brushed and styled and were ready to wear and of course Sarah selected her crowing glory and slipped on the raven hued Bettie Page. She smiled at herself in the mirror. She looked sexy, sensual and utterly feminine.
Sarah was back!
The rest of the weekend was taken up with trying out her wardrobe. Stefan’s choices were mostly perfect although not everything fitted her properly. Although Stefan had looked after his body, time had taken its toll and despite his commitment to walking ten thousand steps a day to stay fit, Sarah had put on some weight. She was no longer the skinny elfin ingénue she had been in her teens and early twenties. But the changes were not too bad. Her buttocks were plumper and she’d developed ‘man-boobs’ but her waist was still slim and her belly mostly flat. Her long legs were still stunning and the makeup she wore disguised some of the wrinkles and scars she had collected over the years. Anyway she didn’t want to look like mutton dressed as lamb, she wanted a more mature sophisticated look.
Of course there were endless selfies to be taken, some closeups, some posing sophisticatedly, some cheesecake shots and of course some provocative shots of her lying invitingly on the bed. These had to be catalogued, enhanced, cropped and saved in a folder. Then there was hours spent on the internet creating profiles on dating and hookup sites and carefully choosing prose to accompany the pictures. She wanted to express that she ‘up for it’ but picky about who she was willing to meet; not desperate.
As usually happens when a new profile pops up on location-based social networking and online dating applications, Sarah’s inboxes became flooded. She quickly blocked the weirdos and those just looking to collect pictures or engage in online sexting. Before she dipped her toes back in the water she wanted to make sure that she found the right man to be her first sexual partner after her enforced celibacy.
After several DMs and an exchange of telephone numbers so they could text, she arranged to meet Darrell, a man of similar age to her who seemed experienced but not creepy. He was insistent about discretion, which suited Sarah who demanded the same and Sarah suspected that he might be married but that was of no consequence to her. She might be new to online dating but she soon discovered that many of the men on the sites looking to hook up with crossdressers were married, even though they might not say so in their profiles.
Stefan had been to the sexual health clinic and after testing was given a prescription for PrEP and advice on how to use it. Sarah considered herself fully armed and ready as Friday drew near. It would be a daytime meet at a cheap motel, another indication that Darrell might be married. Sarah would arrive first and transform and Darrell would arrive an hour later. Darrell would never meet Stefan. Sarah had acquired a new laptop and mobile phone that she only used for Sarah’s avocations. She might now be single and unencumbered but she was no means ready to be outed. Sarah would have full reign over Stefan’s psyche when it suited but she would remain firmly closeted at other times.
Stefan arrived at the cheap motel and paid cash for the room. It was one of those places where such assignations were common and was also used by ‘professional ladies’, the type of establishment commonly referred to as a ‘no-tell motel’. Sarah came to the fore as soon as Stefan closed the door and pulled the blinds. The douching, showering and shaving had been taken care of before she left home so she laid out her requisites and began her transformation. She had popped two PrEP that morning as per the prescribed ‘on demand’ dosage regime. Darrell had asked for the ‘naughty nurse’ costume she was wearing in one of her Bi Australia profile pictures and asked her to wear the blonde bob which Sarah didn’t mind even though she would have liked to have worn her Bettie Page for her first encounter in decades.
Transformed, perfumed and very excited she popped a Viagra and laid out lubricant and condoms within easy reach of the bed. Darrell had seemed reticent about bare-backing when they were texting and she hadn’t pushed the issue. If he wanted to wear a condom that was fine by her.
Darrell opened the door at the exactly the appointed time and quickly stepped inside and slammed it closed and locked it. He was tall, dark-haired and dark eyed, a little overweight but not obese and very nervous but she sensed his excitement when his eyes locked on hers. Her face was enhanced by heavy makeup, her eyes embellished with black eyeliner, black mascara and earthy hued eyeshadow to show off her emerald green eyes. She was wearing a brilliant white micro-mini short-sleeved nurse’s dress and, keeping in character, she wore white satin and lace panties and bra, white suspender belt and white stockings and four-inch white high heels. With her blonde hair she projected as a pristine white fantasy fuck doll. Her Dior Poison perfume wafted across the room.
She was pleased to see the concern leave Darrell’s face and he strode confidently across the room and took her in his arms. He held her close and kissed her passionately, driving his tongue into her mouth. He was eager and horny and she could feel his cock pressing against her through his jeans. Sarah issued a sigh of contentment, she had missed this so much and any concerns that she might regret meeting a man for sex after so much time were soon forgotten.
Darrell’s hands were everywhere. This is what she had missed: his hands cupping the curve of her rump, the soft caress of his fingers stroking her nylon-clad thighs, his hand gliding across the front of her panties, her cock was rampant and distending the front of her silky panties. She could taste a hint of something, not unpleasant, that his mouthwash couldn’t fully mask… rum and Coke? Had he needed Dutch courage to go through with the meeting? His stubble scoured her cheek, the callouses on his fingers rasped against her panties and stockings, his belt buckle caught one of the buttons on the front of her tunic as he pressed himself against her. His outward masculinity authenticated her femininity, his need for her validated her womanliness and her seductiveness.
“God you are stunning,” Darrell murmured breathlessly and kissed her again.
Sarah smiled inwardly and struggled with his belt buckle because his belly was pressed against her. Darrell obligingly arched a little but kept kissing her and in her haste, Sarah chipped her nailpolish unbuckling his belt and unzipping his fly. His jeans fell to floor and she slipped her hand inside his underpants and found his member rampant and dripping precum. Darrell quickly hooked his fingers into the waistband of his Jockeys and they joined his jeans around his ankles then he pulled her close again and continued to aggressively kiss her, whilst his hands roamed over her body.
After all this time Sarah marvelled at the feel of his manhood in her fingers. His cock was long but not exceptionally girthy which suited Sarah because she hadn’t had a cock inside her for years and she knew that she would be tight. She stroked the long veiny appendage and it became fully tumescent and Darreel began to wheeze excitedly. His cock released a constant stream of slippery pre-ejaculate and she could feel the blood throbbing in the veins.
“Stop! I’m going to cum if you’re not careful,” Darrell batted her hand away.
“I know we spoke about taking our time before we fucked but I never expected you to be so sexy in real life and I really want to fuck you right now,” Darrell gasped, breaking their embrace and ripping off his clothing.
Sarah sensed his need and she too was keen to dispense with the preliminaries of foreplay and fellatio, there would be plenty of time for that later, right now she too wanted to fuck. Darrell had been stroking her cock through her panties and she too was close, the short break while he undressed gave her time to recover. She lay down on the bed and posed seductively putting her little finger between her red lipsticked lips, trying to look coy and alluring.
Darrell gazed down at her, her immaculate white uniform open at the top exposing her lacy brassiere, the hem high on her thighs exposing the bands at the top of her white stockings clipped to the garter snaps, her white satin panties bulging, her long legs sheathed in the gauzy, almost transparent, ivory stockings and the matching high heels on her feet. Her face was framed by the platinum blonde bob, her brilliant green eyes sparkling, her red-lipsticked lips full and sensuous. She saw his eyes devouring her and witnessed his cock shudder as lust overcame him.
Suddenly he was on top her, his belly pressing into her, his mouth on hers, almost like he wanted to devour her, his cock between her legs, stabbing at her. She reached out for the lubricant and handed it to him and suddenly Darrell paused. He lay on top of her looking into her eyes with a serious glare. Sarah guessed his dilemma.
“I haven’t had sex with anybody but my wife for twenty years. I’m clean and on PrEP but if you want to use a condom that’s fine with me,” she whispered and reached for the Durex lying on the coverlet.
“I’m married. I can’t catch anything,” he said almost apologetically.
Sarah struggled to unwrap the condom but Darrell snatched it from her hand and threw it away.
“I trust you Sarah,” he smiled down at her and began to kiss her and rut against her.
Hearing a man say her name for the first time in so long was cathartic but she was too was filled with lust to dwell on it. Darrell’s belly was pushing against her panty-clad cock, the satin lighting up her pleasure receptors. She snatched up the tube of lubricant that Darrell had dropped and squeezed a generous dollop on her fingers and struggled to get her hand between their bodies so she could put it where it was needed. Darrell sensed her plight but refused to stop kissing her but he did ease his belly off hers so she could snake her hand between their bodies.
She put her hands inside her panties and smeared the salve on her puckered bud and eased aside the gusset and guided Darrell’s cock into her crevice.
He pushed hard and his cock slid all the way inside her tight back passage. She gasped into Darrell’s mouth at the pain as she felt like she was being spilt open but luckily for her as soon as he was fully inside her Darrell stopped thrusting. Sarah concentrated on relaxing her sphincter and anal passage and was relieved that the ability to do so had not left her. Darrell sensed her discomfort and broke the kiss.
“Sorry Sarah, are you ok?” he whispered.
She looked up into his dark eyes and smiled, her hand stroked his cheek, she pressed her legs against his ample waist.
“I’m ready. Fuck me, you big beautiful man,” she growled and wriggled her ass invitingly.
Darrell looked into her eyes as he began to thrust his cock in and out of her anus. He saw the look of surprise and delight on her face as his cock lit up the nerves ringing her sphincter and her anus, the bulbous head pressing on her prostate. She saw him grin and heard him moan as her anus clasped at his hard cock as she worked her internal muscles to maximise their pleasure. She could feel his cock begin to judder as he fucked her slowly, his belly grinding against her rampant prick.
From out of nowhere she suddenly remembered the last time she had been fucked. Chained to the ceiling, hanging helpless while she mewled, shook and convulsed with the intensity of her orgasm as Dark Hair inseminated her. The memory of it combined with the feel of Darrell’s cock gliding in and out of her slick hole and the pressure of his belly against her pantied organ invoked an earth-shattering orgasm.
Darrell felt her cock judder against his belly and the hot, milky essences saturate her panties and spatter on his belly and he closed his mouth over hers and kissed her passionately as he erupted inside her, filling her cloistered rectum with his seed as Sarah’s anus undulated around his shaft, expressing every drop of his semen.
Sarah slowly came down from her orgasmic high and the memory of the unnamed dark-haired predator fucking her while she hung from the ceiling faded.
“That was awesome!” Darrell kissed her tenderly.
They lay in each other’s arms kissing and canoodling until the Viagra they had both taken kicked in and they went at it again. This time they were more adventurous. Darrell fucked her doggy-style, cowgirl, on her side and in every position they could think off. They both came a second time, Sarah riding him while he stroked her cock until she came all over his hairy belly while he filled her back passage with more of his issue.
Their farewell was a little awkward with promises to meet gain soon and expressions of gratitude for the wonderful time they had spent together. After Darrell left, Sarah removed her makeup and wig, showered and changed back into her ‘boy-clothes’ feeling immensely satisfied and happy that the encounter had gone so well. She was a little disturbed that memories of Dark Hair had snuck into her consciousness during their first session but it was of little consequence. Abe Saffron and his henchmen were long dead or retired.
After her first success encounter, Sarah was emboldened and delighted and keen to express her femininity and sexuality as often as possible. Stefan had, through no fault of his own, almost become a recluse. Devoid of family and most of his friends, living a solitary life, attending the occasional work function that he usually couldn’t wait to leave, he had no real excuse to keep Sarah cloistered.
He transformed into Sarah as soon as he came home from work and spent all of the weekends and holidays as Sarah. She was allowed to fully take over his mind and body and she took full advantage but she hard learned the hard way to stay away from drugs and limit her alcohol consumption. She was promiscuous but selective about who she chose to engage with and soon had a ‘stable’ of men, mostly married, whom she met with regularly and was constantly being hit up online so she had a wide and varied selection of sexual partners.
Sarah was fairly adventurous when it came to sex but drew the line at certain things. She would meet up a few times during the week and spent most of the weekend bouncing from bed to bed, she had a voracious sexual appetite. She started going to Aarows religiously for Tranny Tuesdays which was where she met Cindy. They would often team up in one of the bigger rooms and engage in debauchery with multiple partners. She attended the sexual health clinic regularly and commenced taking her PrEP daily.
The thing was that she couldn’t shake off the memories of being fucked by Dark Hair whilst she was restrained. She knew that it was a dangerous fantasy and always refused to participate in sexual bondage when it was requested of her. She was being careful with her health, staying away from drugs, even poppers - which gave her headache anyway. She was fastidious in her selection of sex partners and very discreet. She loved to roleplay the sexy secretary, the naughty nurse, the loose airline stewardess, and she even had a schoolgirl costume but delving into S&M was just too dangerous.
Cabin 121 Park Motor Lodge, Engadine NSW, Australia
The four men had used Sarah repeatedly until they just couldn’t get it up anymore. Sarah was exhausted and lay on the bed in a fugue. She had submitted to the men and had orgasmed at least three times herself over the course of the evening. Her skirt, blouse and panties were cum-spattered, her stockings laddered, her makeup ruined and her anus was sore and throbbing.
Loyd came into the bedroom and uncuffed her.
“Was it everything you hoped it would be?” he asked and leaned in and kissed her softly.
“It was wonderful but it’s not something I think I could do regularly,” Sarah admitted.
“The other three enjoyed themselves too, did my boys live up to expectations? Did they play their roles well?” Loyd sat on the bed and stroked Sarah’s cheek tenderly.
“The agreement was there would be two of you, not four, but… yes they were perfect, almost too perfect. Salesi’s threat to knock my teeth out and fuck my bleeding mouth was chilling,” Sarah chuckled as she recalled the beginning of the evening.
“You were also supposed to be handcuffed to the ceiling but if you look around this dump, nothing is structurally sound. Besides I thought you would be more comfortable being raped on the bed,” Loyd chuckled too.
“As for there being four of us, when I put the proposition out there to gangbang you to my trusted contacts and attached pictures of you, the response was overwhelming so I chose the three guys I trusted the most. I thought it would be nice to give you a little extra… to enhance your fantasy a little… make it a little more scarier for you,” Loyd’s hand was gently stroking her thigh.
“Well, it certainly did that,” Sarah placed her hand over Loyd’s and squeezed it gently.
“Thank you,” she leaned in and kissed him.
“Next time we meet I would like it to be just you and me,” Loyd smiled at her wistfully.
“I’d like that too Loyd and once again, thanks for setting this up. I hope I played my role satisfactorily. Steve, Salesi and Gary certainly did and you were magnificent as the ringleader. You made my fantasy come true,” Sarah smiled up at Loyd and they kissed again and then discussed when and where they would meet next time.
The End