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OslowCaptions from patreon

OslowCaptions

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OslowCaptions posts

He's a Barbie girl, in the Mistress world.

OslowCaptions post He's a Barbie girl, in the Mistress world.  from patreon

After a couple months as Ken’s submissive, Karen admitted that she was a switch. Ken laughed.

A little girl like you could never dominate a big man like me!

Later that day, while shopping before their vacation, Karen found “The Button” in an obscure junk shop. A press of “The button” would change your ...

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One Gallon Challenge: Mail order failure

OslowCaptions post One Gallon Challenge: Mail order failure  from patreon

After several months of dating, Agnes decided that she could no longer stand Steven’s macho homophobic crap, so she dumped him. As she had done with all her ex-boyfriends, she turned Steven into a woman and then explained the One Gallon Challenge to the terrified girl.

Stephanie’s homophobia recoiled at the idea ...

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Quit while you're ahead.

OslowCaptions post Quit while you're ahead.  from patreon

I should have quit while I was ahead. 

The kid had a good hustle, loose a couple, bet big, turn on his “A” game and clean the sucker out. I watched and I saw that his “A” game was class “C” at best compared to me.
So I turned the tables and had taken him for $5,000 by the en...

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The Button against the world

OslowCaptions post The Button against the world from patreon

Lt. Richard “Dick” Flanagan and Cpt. Dave “Dog” Johnson were Air Force fighter jocks with a problem. They were in love. A secret that could destroy both of them in the 1960s USAF.

While walking on the beach lamenting his problem, Dave came across a sea turtle tangled in a net. He freed the turtle and it chan...

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Unwanted Reunion

OslowCaptions post Unwanted Reunion from patreon

Andrew averted his eyes in shame as the officers led Barbara into the room.

Andy?  Oh God! Is that you?  My poor husband! 

It had been over a year since Andrew had been caught while working deep cover to investigate human trafficking and medical experimentation.  

In...

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His life changed when he met Kara K

OslowCaptions post His life changed when he met Kara K  from patreon

I love the softness of your skin now, the swell of your breasts against mine, the curve of your hips. I’m so happy we chose this.

This wasn’t my choice! I never wanted to be a ….a

A girl? But you have done so much to become one! Hormones, breast implants, voice training and now, bottom surgery. You tol...

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New 5$ member story

OslowCaptions post New 5$ member story from patreon

Betrayed by his wife, Jeff enters a couples counseling retreat only to find himself trapped in a sissy transformation program. Stripped of his masculinity and forced into humiliating submission, Jeff's world spirals into a nightmare climaxing in a final, irreversible change. Will he find a way to escape, or will he forever be...

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Judgement Day: The Cuck of Jessica

OslowCaptions post Judgement Day: The Cuck of Jessica from patreon

None of the other sissies from Jeff’s class had come back once they were called in for their assessment.  No one could tell him what to expect. This morning, Jeff had awakened in agony as the electric shock-cage around his cock surged with power.  

“It’s decision day Jessica...

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Felon 2 Fem: Punitive Pink

OslowCaptions post Felon 2 Fem: Punitive Pink  from patreon

All I did was throw a rock!

I admit that it was wrong. I got caught up in the moment. The new Governor up on stage at her victory party thanking that transgender woman became the newest controversy and I fell for it.

So, when they doxed the woman, I wanted to be part of the story so I painted a rock pink and c...

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Shared Responsibility

OslowCaptions post Shared Responsibility  from patreon

Deanna’s heart stopped when she read the text from Agnes

Change of plans girls! I was going to introduce my new man, Robert at today’s pool party. But it seems Robert preferred lovely Deanna! So, I want you all to meet Roberta, who is joining our sisterhood!

The whole point of Deanna’s seduction was to ...

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Taking one for a friend

OslowCaptions post Taking one for  a friend from patreon

“Oh God, this is gross, and weird!” Deanna thought but there was no other way.  

It had been four months since the breakup, when Agnes turned Dean into Deanna and set her the task of drinking a gallon of cum within a year to change back into a man.  

Deanna had moved in wit...

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Submit.SIR Dom1nat3.H3R

OslowCaptions post Submit.SIR Dom1nat3.H3R from patreon

It had started as a fun roleplay. Danny, had picked up the “Submit.SIR” port-chip from a black-market club. Slot it, define someone as “Admin” and then you would be compelled to obey any command. He talked Pam into slotting it and enjoyed using her as his sex slave for a week.

As they agreed, at week’s en...

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Gender Pandemic Patient 0

OslowCaptions post Gender Pandemic Patient 0 from patreon

My name used to be Owen Marshal. I was a botanist with years of Lab experience, I thought I knew how to avoid accidental exposure. I took all the standard precautions, but, then again, this was a non-standard sample.

They had found it growing in the center of a crop circle and sent it to my lab cause it looked weird....

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Aftermath

OslowCaptions post Aftermath from patreon

Jerry’s hands fell limp on the bed. It was several seconds before he tried to move them. To his shock, they responded! He lifted the manicured nails up and felt the hair cascading from his head. His breasts bulged under his bra and he still felt the void between his legs.

For the first time in months, he was in co...

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The showing

OslowCaptions post The showing from patreon

Fredric held his pose in the darkness terrified that his captors might be watching. Punishment was always brutal and fierce.

A row of lights along the floor came on, almost blinding Fredric. The wall across from him was a mirror and he gasped. The woman in the reflection was unrecognizable!

From the day they...

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Dr. Lilith's legacy

OslowCaptions post Dr. Lilith's legacy  from patreon

I was a 55 year old man on the day of the attack. I was leaving a client site on the train and there was a muffled “Pop” sound.

The train filled with mist that had a sickly sweet odor. For a moment, nothing happened, the train rolled on in stunned silence. Then the cramps started! Everyone was in pain, the men mu...

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Closing the circle, in lace

OslowCaptions post Closing the circle, in lace from patreon

Lawrence and his fiance Sarah, had inherited Sarah’s grandparent’s property and planned to restore it as their dream house. As they cleaned out the basement, Sarah picked up a strange jewel and vanished. Lawrence found a notebook with drawings of the jewel and an incantation. Frantic to save his love, he read the note...

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Ghost in the Sex Machine

OslowCaptions post Ghost in the Sex Machine from patreon

“Rachel, Standby mode!” Dr. Elwood Hasting’s commanded. The Bio-Sim android immediately smoothed her skirt and sat on the couch awaiting a “wake-up” command.

Corwin watched the Doctor walk out of the room and then focused all of his will on simply moving any part of this body. Hastings wouldn’t be back f...

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Charlie won't go bra-shopping alone.

OslowCaptions post Charlie won't go bra-shopping alone.  from patreon

Lookin good Charlie!

Laugh all you want Glen, but you are going to be crying real soon!

HA!! You don’t have the balls Charlie. Literally!

Yeah yeah! I got sent to miss Lilith’s and turned into a girl. You think it’s funny?

Fucking hilarious, From Mr Swinging-Dick to Miss No-Dick!

...

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Behavior Improvement Plan

OslowCaptions post Behavior Improvement Plan from patreon

Have a seat Bruce, this is Carol from HR. She is here to make sure everything discussed here today is clear and to answer any questions. Bruce, you are an asset to this company. Your financial performance has been phenomenal. However, we can no longer ignore your behavioral shortcomings. Cat calling coworkers was bad eno...

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Premium Story: Hailey's Lessons

OslowCaptions post Premium Story: Hailey's Lessons from patreon

Falsely accused and condemned by his own parents, the 18-year-old Henry is sentenced to a "lesson" unlike any other. Under the strict watch of Miss Greenfield, Henry is stripped of his identity, forced into dresses, makeup, and a chastity cage – to finish the last month of high school as a girl.

Publicly shamed and to...

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The Button wakes once more.

OslowCaptions post The Button wakes once more.  from patreon

Benjamin just stared at the mirror by the bed in stunned silence.  There was no warning!  No magic mist or metamorphic transition.  

One moment he was in his T-shirt and boxers, jerking it.  The next moment, “it” was gone and his fingers were rubbing a clit where his...

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Premium Story: Broken Trust

OslowCaptions post Premium Story: Broken Trust  from patreon

When Mike loses his job, he thinks things can't get any worse. That is until his roommate, Ben, reads aloud from a strange, inherited journal, unleashing a transformation beyond Mike's wildest nightmares. Suddenly, Mike is Missy, a woman with an insatiable craving for her best friend. 2025-04-19 15:55:24 +0000 UTC View Post

Premium Story: No Trespassing

OslowCaptions post Premium Story: No Trespassing from patreon

Originally part of the Erotica Consortium's original "Trick or Tease" collection!

When a Halloween prank goes awry, Bruce, Marcus, Stacy, and Kelly find themselves trapped in a twisted game....

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Premium Story: Ghost in the Sex Machine

OslowCaptions post Premium Story: Ghost in the Sex Machine from patreon

Originally part of the 2024 Erotica Consortium "Trick or Tease 2" collection.

He jacked into the system for the score of a lifetime. He woke up in her body.

Corwin Daws, a cocky mesh-ju...

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Premium Story : The Girly Drink

OslowCaptions post Premium Story : The Girly Drink  from patreon

Originally part of the Award Winning Erotica Consortium Anthology "Love Potion 69"

John is a 25-year-old self-described "loser" who has a crush on the amazing Jane. When he learns about a wizard w...

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Heads up: New Tier just launched

I write a lot of stories. They have previously been published in compilations, commissions, or as books on Amazon or Smashwords.
Now I am bringing a premium selection of these stories to subscribers in a new "premium story" $10 tier.
Subscribers to this tier get access to all TG Captions as well as these premium st...

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New Premium Story: Nate's Belief

OslowCaptions post New Premium Story: Nate's Belief from patreon

When Diana learns her boyfriend is a cheater, her friend April proposes a unique solution: use her brain-mapping research to manipulate him. What begins as revenge evolves into a dark exploration of control, identity, and the terrifying power of a belief made absolute.

2025-04-18 18:59:38 +0000 UTC View Post

New to the Premium Stories Tier: A Mother's Love

OslowCaptions post New to the Premium Stories Tier: A Mother's Love from patreon

Ben's graduation day takes a shocking turn when his mother's desperate act transforms him into Isabella. Forced to confront a new identity in a world hurtling towards war, Isabella must navigate a changed body, shattered relationships, and her mother's questionable love.

2025-04-18 18:43:54 +0000 UTC View Post

Cary on wayward ...waitress.

OslowCaptions post Cary on wayward ...waitress.  from patreon

Oh, thank God!  Yes, it’s true.  I am over 100 years old.  

There was a prophecy that a man would unlock the first seal and unleash the end times.  

Apparently, I was that man, destined to end all of creation in 1992.   View Post