A Lady Never Cheats

An Anonymous Commission

Content Warning: This story involves involuntary TG

Taking a forkful of steak into his mouth, Darren chewed a few bites, swallowed, and then reached for his wine glass. When he put the wine down, the glass was already half empty. 

“Dinner is wonderful, Dear,” Darren declared, smiling at his wife, across the table from him. “I’m surprised you remembered my favorite cut of steak.”

“You’ll need to thank the cook for that,” Hellen responded, coldly. “I haven’t been allowed in the kitchen since you hired her.”

“Is that right?” the man took another long sip of wine, before putting the empty glass down.

A maid reacted immediately, stepping into the dining room, taking the glass, and replacing it with another all in one smooth motion.

“…I suppose you’ve forgotten? We argued about it for a week. Or rather, I argued with your voice mailbox for a week, while you took a vacation.”

“It was a business trip,” Darren corrected. “…If I’m remembering the right occasion, at least.” He smiled, taking a more relaxed sip of his wine this time. He only finished a third.

“It’s all a joke to you, isn’t it?” Hellen demanded, not caring enough to hide the anger in her voice. “Our entire marriage is just a big laugh.”

“Of course not, Dear,” Darren protested with a smile. “A joke makes you laugh.” He took another sip of his wine, further reducing the contents of the glass.

Hellen stood, her chair scraping against the hardwood floor as she did so. Without looking at her husband, she began to march past him, and toward the kitchen.

This would have gone entirely without comment by her husband, if she hadn’t also happened to grab his glass as she walked by.

“Where are you going?” he demanded. “Dinner’s not half done – and I’ll need a few more drinks if you’re expecting me to sleep in the same bed as you, tonight.”

“I’m going to get a drink of my own,” was Hellen’s chilled response, as she came to a stop at the edge of the dining room. “You can go without one when I’m not around, can’t you?”

“It is remarkably easier,” Darren agreed, shifting attention from his wine glass to his wife.

A blonde woman, with brown eyes, and a round face that lit up when she smiled. 

Not that Darren could remember the last time his wife had smiled.

He’d used to be able to make her smile. Back when he was nothing but a college student, with nothing to offer her but a song he’d composed in music class – she’d smiled. She’d smiled, and agreed to go out with him, and he’d smiled in turn.

At the time it had seemed the farthest thing in the world from a mistake, but while he’d heard Hellen was wealthy he had not yet understood the true reach and age of her parent’s wealth and influence. It was only after meeting them in their mansion that he’d understood the sort of life he’d be expected to provide.

Of course, Hellen had claimed such things didn’t matter to her. She said it was no problem to put up with it, at the small apartment he could afford from his work in telemarketing.

She hadn’t objected, though, when her father offered him a position in management at an investment firm. She hadn’t raised a complaint when he was fast tracked to promotion after promotion, especially not when he’d used his continuously growing income to make her life better.

Yes. Darren had worked hard to improve living conditions for his wife, with his own well being becoming almost an afterthought. Yet when he’d finally reached a level where he could provide at least a fraction of what she was used to, she’d started with the complaints.

She’d said he worked too many hours. That he never spent time with her. That he spent more time with his secretary than her. She’d gotten so jealous, she’d even offered to work as a secretary herself, saying she only wanted to spend more time with her.

He’d refused, of course. All the things he was doing would have no purpose if he couldn’t give her the life she expected. It was his job to provide. She should have understood that. That was why she’d let her family pay his way forward, wasn’t it?

Yet she always had more complaints… And slowly but surely, under the weight of those complaints, their relationship had fractured. 

Not that her cheating had helped any.

The clink of ice against glass brought Darren back from his thoughts. His wife had leaned over the table, apparently to deposit a glass of scotch on the rocks to him.

“…I thought you were just getting a drink for yourself,” Darren remarked. He still took the glass, though, bringing it to his lips and taking a small sip.

“After taking yours? No matter how you see me, I’m not actually heartless.”

Darren grunted a noncommittal answer, draining a bit more of the glass. Scotch was a drink you sipped, and he knew it, but he was pushing that to the limit.

His wife returned to her plate, eating a small portion of steak and all of the green salad that had been put on the side. She then pushed the plate away and stood.

Darren, who had only finished half his steak and a quarter of his salad, raised an eyebrow. “Eating fast tonight?”

“I thought I’d get an early start on bed,” Hellen replied.

“Hoping to masturbate before I get there, Dear?” Darren asked, wearing the same fake smile he always used when talking to her.

“Not tonight,” was Hellen’s surprisingly honest response. “Perhaps you’ll help me, instead.”

“…Thought your lover had you covered there. Wouldn’t want to step on his toes.”

“I’ve told you a hundred times before. I haven’t slept with anyone but you; and I have no intention of doing so for as long as we are married.”

“As if I’d believe that,” Darren scoffed, stabbing his fork into his steak. “You won’t let me fuck you. You haven’t in forever. You practically flinch when I try to touch you.”

“The flinching started after you started accusing me of cheating,” Hellen protested.

Darren took a long sip of his scotch, reasoning that some of the ice must have melted and watered it down by then. It was left unsaid that, prior to that, it had already been four months since Hellen had let Darren touch her. 

When he finished the glass of scotch, he put it down, and the maid scurried in to replace it with a glass of wine.

With his wife gone, Darren managed to finish the rest of the meal with just that glass. He finished off the steak and ate all of the salad, and was in something of a gluttonous haze when he stood to his feet, only to stumble.

At first, Darren thought nothing much of this near trip. He was drunk, and there was nothing unusual about stumbling a little. It was only that, after righting himself, he noticed the table looked a bit taller than normal. Or rather, everything seemed a little taller than it had been a moment before?

Thinking he had imagined it, he placed a delicate hand upon his forehead, only to freeze as a cold sweat broke his brow.

Darren had never done much physical work. He had nothing that could be called a callus on his hands or fingers. Still, to call his large hands delicate would surely be an ill descriptor. Yet, surely, he had felt delicate fingers upon his own brow. And indeed, lowering his hands before his eyes, he found them small and delicate, with short trimmed nails.

“Wh-What’s going on?” he stammered out.

He was smaller. His hands especially so. Was he getting younger? He ran fingers around his cheek, and once more froze in place.

He was devoid of even a five o’ clock shadow. He shaved, daily, but he was always able to feel a few hairs, nonetheless. Now there was nothing.

Yet if he was getting younger… at his current height, he should have still been able to grow a beard. “It doesn’t make any sense,” he muttered out loud – and paused, yet again.

His voice had come out with a higher pitch than intended.

“Is that… Me..?” he asked no one in particular, confused and alarmed. He still had yet to fully grasp what was going on.

He felt a strange weight behind his head, and reached back to find long tresses of brown hair. First he lost hair, now he’d gained it elsewhere?

That was when he felt a pressure in his chest, a blossoming warmth. Unbuttoning his white shirt, he was shocked to find two budding breasts swelling up beneath.

The breasts grew, even as Darren watched, shifting from something small enough to fit in even his delicate palm, to something that might have strained her old hands to grip. This happened in the span of seconds, and by the time Darren thought to try and protest, scream, or even physically press the breasts back into his body, it was already done.

“N-No way…” Darren whispered, staring at the rather large breasts he was quite suddenly endowed with.

It was at that moment that Darren felt another warmth – in his ass, this time.

“N-No!” he protested, firmly pushing his hands into his pants and placing them on his own rear.

He was treated to the sensation of something soft, and thick. A fat ass that would grab attention anywhere he went.

“Th-This can’t be happening!” Darren screamed, looking about. “M-Maid? M-Maid!?” he called.

The maid, however, did not come. Perhaps because she did not recognize the screaming voice – or perhaps she had simply been told to go home, by someone else of stature in the house. 

It was at that moment that Darren felt a warmth in his crotch.

“Th-That too?” Darren whispered, pushing down his pants and boxers to get a better look. It wasn’t a protest, not really. After everything else that had happened, he almost didn’t see the point in holding onto this. Nevertheless, his eyes were filled with tears.

A slit opened between Darren’s legs. His balls were slowly drawn inside, the excess flesh shifting into folds of a new pussy, while the testicles themselves dissolved into nothing.

His penis shrank and even as he stared down at himself, sniffling, he watched as it became nothing more than a clit.

“Wh-Why is this happening to me?” Darren asked, rubbing at his cheek. He’d been given a feminine form. That much was obvious. Something must have caused it. Someone must know something about it.

The alternative – that Darren was trapped in an unrecognizable form, with no paperwork, no allies, and no one who knew the truth – was too horrible to consider. Someone had to know that he’d be made to look like a woman.

The only one who came to mind was Darren’s wife. She was the only one who’d have the money and motive to pull something like this off. The cheater who couldn’t be satisfied with the life he could give her – had she decided to get rid of him?

“I don’t want to imagine what’s going through your mind right now…” came a familiar voice, causing Darren to spin.

Hellen was standing outside the dining room. She was wearing  black lingerie, a two piece bra and panties with a nearly transparent, yet still visibly black, chemise over it.

“Y-You did this,” Darren accused, wishing his newly high pitched voice would come out more angry and less petulant. “You turned me into a girl!”

“I made you look feminine, yes,” Hellen responded, striding up to Darren. It was strange, being at eye level with his wife. He could see right into her warm brown eyes.

How long since she’d looked at him like this? With actual affection in her eyes? The presence of it here, now, confused Darren enough that he was momentarily silent.

“I’ve had my eye on this drug for a while; highly experimental. I had to grease quite a few pockets for the pill that I mixed into your drink – but it was well worth it. Just look at you… You’re beautiful…”

Reaching out, Hellen ever so gently lifted a lock of Darren’s hair, smiling with such joy that Darren couldn’t help but take a step backwards from her.

“Wh-Why did you do this?” Darren asked. “Did you want to make me disappear? You could have just asked for a divorce!”

“…Why would I want someone as beautiful as you to disappear?” Hellen asked, this time reaching out to place a hand on Darren’s cheek.

The cheek warmed in response, a blush spreading across Darren’s features. Despite himself, his heart was beating faster at the words. “Why did you do this to me?” he asked.

“Because my family doesn’t believe in divorce,” Hellen responded, a cheeky grin on her face. “And I don’t believe in cheating. So this was the only way I’d ever get to sleep with… Well, actually, how do you identify. Dear?”

Her smile turned poisonous with those words, and Darren swallowed hard. “I-I’m a man. I’m a man! You know I’m a man!”

“Funny…” Hellen whispered, reaching out to take one of Darren’s hands in hers. “You were just talking about how you’d been turned into a woman… Are you sure you aren’t a woman, after all?”

“I-I’m sure!” Darren squeaked, heart beating faster and faster. Shockingly, it was not with fear.

It was from the unbridled joy of being touched. The wonderful feeling of being looked at, with affection and warmth.

It was also from arousal. Darren hated to admit it, but his nipples were stiff, his clitoris was throbbing, and he could feel the muscles in his newly formed pussy responding, as clearly as he felt the growing sensation of wetness between his thighs.

“My… It worked better than I thought it would…” Hellen whispered.

“Wh-What are you talking about?” Darren asked.

“The part where your body gets aroused by me. The part where you can’t help but feel for me. And especially, I hope, the part where you can’t help but listen to what I have to say…”

“Y-Why would you do that?” Darren meant to scream the words, but they came out as a bare whisper, a polite question. It didn’t matter the reason. He couldn’t help the way he felt: like Hellen was suddenly his whole world.

“Relax, dear. It’ll only last a few more minutes… Though I intend to use them to their fullest. Quite simply, though, it was the only way you’d listen to me.”

“Listen to you?” Darren asked, confusion clouding his brow.

“I didn’t cheat on you. I’ve never cheated on you. I never would cheat on you. I simply stopped wanting you to touch me… Or rather, realized I had never enjoyed you touching me. Because I’m a lesbian.”

“Y-You’re… why didn’t you tell me?” Darren asked, confused and hurt, yet still edging closer to Hellen. He wanted to press his flesh against his wife, to be touched everywhere at once for as long as possible.

If this was all due to a single pill, then it was unbelievably potent.

“How was I supposed to tell you that I wanted you to be a girl? That I needed you to be a girl? That of all the things you’d given me, the one thing you couldn’t was being a girl… I couldn’t even get you to listen when I said I needed you to spend more time with me. How would you have taken that?”

“I…” Darren hesitated. He had no response for her.

Hellen smiled, sadly. “See? But I couldn’t give up on happiness… For both of us.”

“How am I supposed to be happy like this!?” Darren complained. “Looking like this? Feeling like this, every time you’re near me?”

“I told you, the feeling will last only a minute or two more,” Hellen reminded him. “I only needed it for one purpose…”

“And what purpose is that?” Darren demanded.

“…Getting you to accept that you’re a girl.” 

The words were spoken quietly, so much so that Darren wasn’t sure they’d been spoken at all.

“What?” he asked.

“I want you to be a girl, Darren. I want you to be a woman. For real. I can do it – with the power I have over you, right now, I can rewrite you to fit your new body. And we can be happy together, at last… But I don’t want to do it without your permission.”

“My- My permission?” Darren shook her head, back and forth, barely able to believe it. “My permission!? What about my life? What about the company? What about my job?”

“I’ll provide for us, from now on,” Hellen promised. “We’ll be happy together. We’ll have everything we need – and you’ll be my wife. We’ll tell the public that you’ve decided to cloister yourself, and focus on transition. When enough time has passed, we’ll show you to the world.”

“Tran-Transition? We’re telling everyone this was my choice?” Darren asked, hardly able to believe the audacity.

“…If you don’t want to, I have arrangements set up. I can get you a new life. But either way, the person you used to be is going to disappear. The you who cheated on me, all the while saying it was okay because I’d done it first.,.. Is going to disappear.”

The look in Hellen’s eyes was no longer warm. It was cold, and hard.

Slowly, Darren nodded. “What do you need to do, then? To make me… A woman?”

“This…” Saying so, Hellen pulled Darren into a kiss, pressing her lips against his with all her might, and wrapping her arm around his head. She gave no quarter, no room to breathe, no ability to pull away.

Not that Darren was trying to. His mind was blank, a white expanse of nothingness as pleasure irradiated his system. It felt so good, touching lips with Hellen. Being with Hellen, even. Just smelling Hellen…

“You’re a woman,” whispered a voice in Darren’s ear, and she accepted it without question. “Your name is Bethany,” the voice added, and Bethany nodded in acceptance. “You came to this conclusion on your own – risking our very happy marriage, because you knew what needed to be done. You asked me for the pill that would transform you. This is the happiest night of your life, having your dream come true. The happiest night of both our lives.”

“The happiest night,” Bethany responded, a small smile on her lips.

Her eyes opened, slowly. She was sitting on the floor, for some reason, which she found odd. Hellen, her wife, was standing above her with a worried look on her lips.

“Perhaps I overdid it?” Hellen muttered.

“Overdid what?” Bethany asked, hopping to her feet and grinning at her wife. “Nothing too bad, I hope.”

“Nothing at all, dear,” Hellen replied, a small smile on her lips as she reached out to stroke Bethany’s cheek.

A warmth blossomed in Bethany’s chest, happiness that her wife would touch her so tenderly. Happiness that her wife accepted her, for that matter, and that she could still call the woman her wife after all this time.

“I was thinking…” Hellen whispered, suddenly taking Bethany’s hand and tugging forward, so that Bethany flew into her arms. “I was thinking we should have some fun tonight…”

Bethany looked hungrily at her wife: at the transparent chemise, the black bra, and the matching panties.

“…Race you there?” she suggested, before taking off.

She took off at a run, almost stumbling while going up the stairs. Still, she made it there just a heartbeat before her wife, and leaped into the bed.

Hellen laughed in response, climbing more carefully atop the sheets and moving to undo Bethany’s tie.

“It’s nice to see you happy, again…” Hellen sighed.

“What do you mean?” Bethany asked. “How else would I be?”

Hellen only shook her head, and undid the remaining buttons of Darren’s shirt. 

“You really do look beautiful…” Hellen whispered, staring hungrily at Bethany’s large tits. “I’m so glad you agreed to me making them this large.”

“Did I?” A confused frown graced Bethany’s lips for a moment, but then she shrugged it off. The details of the planning were all a happy blur. All she could remember was how excited she’d been, the closer she’d gotten to achieving her dream body.

Still… “Are you sure those weren’t a special request from you?” she asked, cocking an eyebrow. “I always imagined myself with something smaller.”

“Do you mind if it was?” Bethany asked, staring hungrily at the tits.

“Not really…” Bethany laughed. “So go ahead. I can see you’re barely containing yourself.”

Letting out a small noise of happiness, Hellen lowered her lips to a breast, and placed her lips against the nipple. Her tongue lashing back and forth over it, her teeth ever so lightly grazing the flesh, she worshipped the breast before her with fervor, parting only to breathe, before diving back in. Like a woman long starved of something vital, she all but attacked the breast with kisses and bites and the gentle caress of her tongue.

Bethany responded by tilting her head back and moaning. Those moans turned to screams as the kissing continued, and her body convulsed with pleasure that momentarily turned her mind to white nothingness. 

When she was back to herself Hellen was wearing a warm, slightly smug,  smile.

“Don’t think I’ll let myself be the only one who orgasms tonight,” Bethany declared, reaching for her wife’s panties.

Hellen stayed perfectly still as Bethany pulled the panties down Hellen’s thighs, spreading her legs once the panties were down to her ankles. Her pretty pussy was on display before Bethany, and Bethany couldn’t help but smile at the sight.

Lowering her head to gently kiss the folds, she moved a thumb to start teasing against Bethany’s clitoral hood. Once she’d teased the button into view, she ever so lightly touched it with her thumb, while licking and teasing Hellen’s folds.

In the end, it took very little to make Hellen cum.

When she did, she screamed Bethany’s name.

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