Gaypril: Scared ‘Straight’

Kenny did not recognise the woman who entered. She was small and slender – a waif of a thing really – with the grey of age showing in her temples. She wore a tweed jacket over a plain white blouse and plainer black trousers, her flat shoes some fifty years out of date – older than she was, he was certain of that – and though she cast him a brief smile, her grey eyes pored over the clipboard in her grasp.

Her presence confused Kenny. He had sat in this same chair in this same interrogation room dozens of times and the story was always the same: he’d spend half an hour or so getting a thorough talking to either by one of the local PD’s officers or a well-meaning counsellor, after which they would send him on his way knowing full well he would be cluttering up their station by the following week. It was the same record they played week in, week out, but Kenny was hardly a hardened criminal – his transgressions were rarely serious enough to earn him anything more than a meagre fine, let alone a stint behind bars, and so long as that was the case this was the routine they would continue to follow.

However, this woman was something new. Kenny supposed she could have been another counsellor, but she didn’t look like any who’d visited him before, nor did she resemble the single psychiatrist who had tried and failed to help him mend his ways. And she certainly wasn’t an officer.

‘Who are you?’ he said bluntly as she took the seat opposite him. ‘Not seen you before.’

The woman raised an eyebrow at his brusqueness, though when she spoke her tone was warm, friendly even. ‘Oh, you wouldn’t have dear. I work here at the station, but I don’t tend to do suspect interviews all too often. My name is Eliza. I’m in… well, rehabilitation I guess you might say. I’m something of a last resort.’

Kenny scoffed and folded his arms. ‘So another shrink. You should have just said.’ He slouched in his chair, tugging down the hood of his tattered grey hoodie. ‘Go on then, analyse me if that’s what you’re here for.’

‘I’d rather not,’ she said, her lips pursed in a disapproving line. ‘Quite apart from my utter disinterest in the limited inner workings of that empty head of yours, Mister Taylor, I don’t need a psychiatry degree to perceive how hopelessly pathetic you are.’

Kenny was stunned. Nobody had ever spoken to him like that. Sure, the usual suspects who interviewed him were stern and sometimes a little sharp, but never insulting. Yet this woman – a full head shorter than Kenny and with less muscle mass than a lazy toddler – was practically baiting him into an argument as though he couldn’t beat her to a pulp if he liked.

‘As I said, I am a last resort,’ Eliza went on. ‘I am bought in when men like you who are perfectly willing to throw their life in the gutter step out of line once too often.’

‘You don’t know me,’ he spat, a sudden hate for this bitch welling up inside him.

‘Do I not? I’d say I have a fairly comprehensive understanding of you.’ Turning her attention to the clipboard she flicked through the sheaf of pages. ‘Petty theft, indecent exposure, vandalism and graffiti, joyriding, personal possession of a class B drug, general delinquency…’ She dropped the clipboard sharply, a sudden edge to her stare. ‘Need I go on? To put it bluntly, you are a prison inmate waiting to happen. Sooner or later you will escalate into more serious offences, and when that time comes it won’t just be yourself affected but our community as a whole. We do not tolerate crime in this town, and since you have refused to co-operate with any other means of rehabilitation, I am here to set you straight.’

Before Kenny could devise some sarcastic remark, Eliza hit him with a question he definitely hadn’t been expecting to be asked when bought into the station that morning. ‘Do you believe in magic, Mister Taylor?’

The question was so odd he could not think to reply with anything but the bare truth. ‘No.’

‘I thought not; men like you never do. Fortunately for everyone else, you are as wrong about the existence magic as you are about most things, and today I will personally delight in proving it to you.’

Ignoring his scoff of disbelief, Eliza produced an immaculate ring from her jacket pocket. It was old, ancient even, the kind of piece one might have imagined on the finger of a medieval monarch, a bright diamond set into the gold band. Despite its visible age, however, it glittered like new and, like a true criminal, Kenny found himself wondering how much it might be worth.

‘Centuries ago, when this town was first founded, there was a woman who lived up on the hill where the schoolhouse now stands. She was a wise woman who loved her town; she was a teacher, a wife, a mother, and, as luck would have it, a witch. You see in those times stability was hard to come by. Swindlers, thieves and more sinister men were forever searching for an easy mark, so she turned to magic in order to protect herself, the people she loved and the town she called home.

‘This ring belonged to that woman.’ She held it up for him to eye suspiciously. ‘Alas, nobody knows her name anymore, but her legacy lives on through her descendants – descendants like me. Upon her death she imbued this ring with all her powers and passed it to her daughter, with the intention that it be used to protect the town even after she was gone. And so it went throughout the years, passing down from parent to child, all the way to me.

‘Times change, of course, and while my ancestors used to have to protect themselves against roaming miscreants, these days we use magic for those threats a little closer to home. I doubt you have noticed, but you don’t have much company as a criminal in this town. We try less invasive methods of rehabilitation before I intervene, but when it comes to men like you, a little magic can go a long way. Here, let me show you…’

The moment Eliza slipped on the ring, the air around her began to shimmer. Sparkling streaks of light circled her, like tiny comets in orbit of her small frame, and she was lost under a dense mirage-like haze. Kenny scrambled back, his face twisted with fear, and as he cowered against a filing cabinet he realised the glittering, swirling image before him might have seemed almost cliché had it not been so deeply unnerving.

He tried to convince himself it was just some kind of trick, the lights cast by a hidden projector, perhaps. But his theory began to crumble as Eliza’s frame expanded. Blurred by the roiling air as she was, her outline was still visible and he watched in shock as she rose to a towering height. The vague brown of her tweed jacket faded into a rich blue, and he could see midnight locks contrasting against porcelain skin, giving the impression of an oversized china doll rather than the ageing busybody he had just been speaking too.

Busty trans woman poses in stockings and blue silk dress

In a sudden flare of light, the air settled. Kenny blanched.

Eliza was gone. In her place stood a mesmerising woman in sleek heels, gleaming stockings and a long blue silk dress so dark it was almost purple. Inky trusses framed features made up with almost surgical precision, and her curvy figure was accentuated by her attire, the bosom of her dress stretched taut across her breasts and the rear draped over her considerable rump. Her arms were bare, the skin perfect and supple, and her wrists glittered with diamond-encrusted bracelets to match her ring. Heavy earrings of large black gemstones hung almost to her shoulders and her nails were painted the same deep crimson as her full, sultry lips.

As she leaned against the table she fixed him with a piercing gaze and Kenny’s stomach flipped. No… Eliza hadn’t gone. She had changed. Though every rational thought told him it was impossible, he recognised the edge in her eyes. There was no question about it: this was the same woman in a different body.

‘Come now, Kenny, don’t get all tongue-tied on me now. This is the fun part.’ Eliza’s new voice was soft as a summer breeze and sweet as golden honey. Her words wreathed around his head like a fog, clouding his thoughts. She lifted her dress suggestively, the bare flesh of her upper thighs tempting him in. ‘I don’t think anyone in this station ever imagined you’d be speechless. I’ll consider that a compliment.’ For the first time he noticed an unusual swelling at her crotch. ‘You look tense, baby. Here, let me help you with that.’

Eliza thrust her hand in his direction and immediately the tension in his stance melted away. He stood casually, one hand hooked in his trouser pocket, and his racing pulse calmed swiftly. Even his inner fear mellowed. Though he was still cautious of the beautiful woman, it was a caution of unfamiliarity rather than fright; the startling transformation she had undergone didn’t seem to matter and his eye fell to linger on her heavy bust.

‘That’s better,’ she purred. ‘Now let’s get started.’

Busty trans woman poses in stockings and suspender belt

With a snap of her fingers, Eliza dissolved her dress into nothing, and Kenny realised with a start what the bulge had been. Where he had expected a flushed pink pussy she sported a set of heavy balls and an enviable cock. Presently small, it was rising quickly, the head glistening with her arousal. Despite her unexpected genitals, lust was beginning to swell through him and he soon found his own erection starting to tent his jogging bottoms.  

To his dismay, the sight only drew a disdainful look over Eliza’s face. ‘Well that certainly isn’t a flattering look. The horny chav aesthetic isn’t do anything for me I’m afraid dear. I think it’s time you had a makeover.’

Another snap of her fingers and Kenny suddenly looked like a new man. His stained hoodie dissolved to reveal a crisp white shirt and black suspenders, which had replaced the grubby band tee he had been wearing. While his erection continued to grow, it was now firmly pressed against his thigh, contained in sleek black trousers which descended to crown glossy black dress shoes at least ten times as expensive as the filthy trainers they had taken the place of. With a thin black tie to complete the look and his once greasy hair now oiled into a trimmed quiff, Kenny looked the image of a diligent office worker.

His toned body and handsome features no longer obscured, Eliza realised how attractive he was: she was going to enjoy this.

Man in white shirt eats ass of busty trans woman in stockings

‘Over here,’ she commanded, and she smiled as Kenny came trotting over. ‘Kneel.’ He did so. She took a moment to savour his obedience. Inside, she knew, he was reeling, his thoughts a conflict of lust and confusion as his body followed her orders automatically. Briefly, she considered rewriting his consciousness there and then, but then she hesitated: leaving him like this was far hotter. His mind in turmoil, his body under her control – the bewilderment in his eyes was so deliciously erotic compared to the implicit obedience he demonstrated. Leaning over the table she presented her plump ass to him, chuckling softly as she pondered what thoughts were tumbling through Kenny’s head. ‘Eat,’ she said.

Kenny obliged instantly. Burying his face between her cheeks, he lapped at her tight hole frantically, his broad hands rising to clutch her thighs and pull himself in deeper. What he lacked in technique he made up for in enthusiasm and, despite the fact he was staunchly against ass-play and rimming in particular, his tongue was soon forcing its way into her hole.

Just as Eliza assumed, Kenny’s mind was in a frenzy. Desperate to please Eliza he eagerly ate her ass, yet in the back of his mind confusion reigned. All the memories of who he had been before falling under her spell were still there, though they seemed entirely unimportant. As his scorching arousal threatened to burn up his insides, the voice begging him to resist went ignored; betraying everything he had once been, Kenny surrendered to Eliza’s power.

All the while Kenny ate Eliza out, he could sense the weight of her magnificent cock swinging between her legs. Her balls frequently rubbed against his fingers grasping her inner thighs, and once she had engorged to her full length the resounding slap of her shaft against her stomach as she rocked over Kenny’s face echoed through the room like a sordid drumbeat.

The thought of what it might taste like eventually had the former delinquent salivating heavily. His heart missed a beat when she at last pushed him away, expecting her to spin around and drag his lips over her juicy rod.

As it happened, Eliza had something else in mind.

Busty trans woman gives anal sex to handcuffed man in shirt and tie over table

Dragging him up, she threw him over the table with unexpected strength. Kenny suddenly realised how powerless he was against her, though that clarity was sharply overwhelmed by arousal as a set of handcuffs materialised about his wrists and Eliza’s hands seized his short hair to wrench his head back.

‘I know you’re enjoying this, but this isn’t about you. It’s about all the people you’ve harassed and bullied and tormented over the years. This is their justice. By rights you deserve to fuck up your own life with drink and drugs and depravity until you find yourself in some gutter wasting away like the worthless nobody you are. Fortunately for you, my forebear believed in second chances, and so do I. So this is your second chance, Kenny. Not that you have any choice in the matter.’

Eliza didn’t even bother exposing him herself. Pointing at the waist of his trousers she gestured sharply down, and they fell as if pulled by unseen hands. His boxers having dropped around his ankles with them, his vulnerable ass was hers for the taking.

And take it she did.

Plunging inside him with one powerful thrust, magically-produced lubricant allowed her to slide herself in balls deep, filling her unwitting slave so completely his legs trembled beneath him. Then, with his head held high in her firm grip to prevent him lolling about and ruining her rhythm, Eliza began to thrust.

It was fortunate indeed that Kenny was supported by the table, for no sooner had she begun than his legs were reduced to jelly. Even if he had wanted to listen to the voice of his former self, he would not have been able to hear it, for the ecstasy singing through his mind drowned out all else. His hips burned with agony-laced pleasure as she stretched his virgin hole, while his jaw hinged open and closed uselessly, the orgasmic howls snagging in his throat; every time he went to scream Eliza’s cock slammed against his P-spot and sent blinding rapture roaring through his system, the effect so intense it shattered his cries and reduced them to little more than hoarse gasps, which bubbled on his lips like frothing drool.

Lost in his euphoria, Kenny failed to notice Eliza weaving her spare hand over his temple, fashioning an addiction to this pleasure from his lustful thoughts and slowly erasing the man he had been before.

Handsome man receives anal sex from busty trans woman on table

As Kenny tumbled further into submission, their passion became ever more intimate. What began as Eliza fucking him over the table soon shifted into Kenny lying back over the scattered papers detailing the transgressions of his previous life, his tie in her hand as she pounded him into a breathless mewling mess; later still, once she had used her power to extract the whining streak from her toy’s thoughts, she took to the table herself for him to demonstrate his skills in riding cock.

The slutty rocking of Kenny’s hips drew a cold smile over her bloodred lips. This was her favourite part. Her orgasm was approaching, her cum ready to seal Kenny into his new life of submission. But before that, she had something to tell him: the last thing Kenny Taylor would ever hear.

Snapping her fingers, she summoned his original persona to the front of his mind. His body continued to ride her, yet raw terror overtook his features and there was horror in his eyes.

‘Enjoying yourself?’ she grinned.

‘What have you done to me?’ Kenny gasped, his voice faltering as the pleasure threatened to drown him.

‘I’ve given you a second chance. Like I said, we don’t tolerate criminality in this town, and now you’re going to be far too horny to even think about stealing anything. If I were you I’d think yourself lucky; you’d have never experienced pleasure like this without my intervention.’

‘What’s going to happen to me?’

The fear in his eyes almost pushed Eliza over the edge. ‘That’s the poetic part actually. Normally this is the point where I tell you I’ve found a nice boyfriend to love you, if I’m feeling generous even a job somewhere other than a gay strip club in the city. But I’m afraid that’s not how things are going to go. You see you’ve been a thorn in the side of this police department for years, Kenny, and we all agree it’s about time for a little payback. From now on you’re to be an assistant to the chief and you’ll work here in the station. I’d like to say you’d find it to be a fulfilling career, but I suspect it will be more the case of a career that fills you. But since you’ll be working so hard servicing your new colleagues it’s only fair you have a nice home to go to afterwards: namely the chief’s. You won’t just be assisting him at work, but as his twinky little pet at home too. I’ve given you a new life, Kenny, and you’re going to live it with a cock buried in your holes.’

Kenny looked ready to scream. However, just as before, her forceful thrusts shattered his cries and he was left with an expression of silent terror.

Eliza chuckled to herself. ‘You know, it’s funny, I’ve never really thought of it before, but other places try to rehabilitate guys like you by scaring them straight. And I guess I am scaring you, but once I’m finished you’ll be anything but straight.’

At that moment, Eliza’s orgasm broke. Fat tits heaving and cock throbbing so hard she could feel it in her ribs she fired her hot load with a gasp of pleasure and all at once Kenny Taylor was extinguished. The horny cock-addict she had fashioned him into instantly filled the void his discarded persona left behind and even before she had finished he was begging for a fresh load.

‘Oh don’t you worry, slut. You’re never going to go wanting for cum from now on. Now shut up and ride – I want to see how many creampies this sweet ass can take…’

Two tattooed men have sex on bed

By the following week, the new Kenny had settled in well to his new life. He could often be found kneeling in the station break room ready to help relieve the stress of any staff who desired his services, from officers just off duty to cleaners in need of an energy boost. Whenever he was not there, he was sure to be in some office or another, crouched beneath the desk of one of his colleagues who had decided they needed a little personal attention from obedient little Kenny ‘Cocksucker’ as he was now known fondly within the department.

Meanwhile, beyond the station’s walls, he gleefully devoted his new life to serving the long-suffering chief of police he had caused so many frustrations over the years. Kenny was eager for his new master to take out those frustrations on his slutty holes, and like a good little pet he made sure to wake sir with a sensual blowjob every morning and soothe his stress every night by presenting his willing holes to use.

And in the rare moments he isn’t speared on the cock of some depraved colleague degrading him with insults about a delinquent past he cannot remember, he always finds the time to visit Eliza and her wonderful dick.

Though he isn’t sure why, Kenny always feels like he should thank her, as though she helped him once, long ago, in a different life. Yet when he says as much, Eliza merely smiles before presenting her juicy meat for him to worship…

Thanks for reading!

When scheduling this month’s releases, I generally organised them in order of which I was most pleased with, and at this point we’re really starting to reach those stories I am profoundly proud of. To be clear, I am very happy with all the content I’ve produced for this month, all of which I think balance detail and sexiness really well, however the stories from here onwards really push my personal buttons and I’m super happy to have them releasing for others to read.

Certainly one of the reasons I love this story so much is because the models supporting it are truly awesome. Those models being Domino Presley, Kaleb Stryker and Wesley Woods.

Presley is pretty much trans porn royalty at this point, as popular on the trans scene as any big names like Riley Reid or Abella Danger are within the mainstream porn industry, and for good reason. Presley has a truly impressive body of work and has starred in scenes with some of the hottest men and women in the industry. If you like trans content and you haven’t seen her work, frankly you’re doing something wrong.

Stryker’s work was of course showcased alongside Natassia Dreams in my early story Wrong Place, Wrong Time, and as I did there I’ll link his profile here too since his PornHub profile is fairly bare. There isn’t much to say about him that I didn’t already mention in my comments on that scene, so just go check out his work – you won’t regret it.

As for Woods, he is also an impressive model in his own right. That said, while I was searching for a decent online profile for him, I discovered he has retired from the industry. As far as I can tell he had a fairly brief tenure, but in that time he created some phenomenal content and I implore fans of gay scenes to check him out. My research also tells me he enjoys doing stand-up comedy and has appeared on a few different podcasts here and there, so if you’re interested in seeing what kind of things retired models like Woods get up to beyond the industry, definitely take a look into what he’s currently doing.

I would love to hear your thoughts on my work, so please leave me a comment!

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