Crossdressed Secretary Forced to Submit - Cover

Crossdressed Secretary Forced to Submit

Copyright© 2025 by Michele Nylons

Chapter 1: The Cabin

Erotica Sex Story: Chapter 1: The Cabin - Sarah is a mature crossdresser with a dark past. Searching to relive something that happened to her when she was a teenager, she agrees to meet a man in a no-tell motel but is totally unprepared for what is about to happen to her. A group of men have their own plans involving submission and degradation.

Caution: This Erotica Sex Story contains strong sexual content, including Mult   Coercion   Rape   Reluctant   CrossDressing   Fiction   BDSM   DomSub   Light Bond   Rough   Gang Bang   Group Sex   Black Male   White Male   White Female   Anal Sex   Cream Pie   Facial   Oral Sex   Petting   Voyeurism   Leg Fetish   Small Breasts  

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.

 
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