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Sissy Stories & Captions
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Mind Reprogramming for Sissy Sluts 06:32
Mind Reprogramming for Sissy Sluts
Your Best Friend's Bitch - AbjectBetaSchool 04:41
Your Best Friend's Bitch - AbjectBetaSchool
X-Change - The Gender Swapping Pill 06:35
X-Change - The Gender Swapping Pill
Promotion And Benefits - Sissy Caption Story 09:52
Promotion And Benefits - Sissy Caption Story
Closing Deals - Sissy Caption Story 09:21
Closing Deals - Sissy Caption Story
Chastity Cages Get Ripped Off - A Short Chastity Story 03:03
Chastity Cages Get Ripped Off - A Short Chastity Story
No Looking Back - Gender Swap Caption 03:45
No Looking Back - Gender Swap Caption
Baby It's Cold Outside - Gender Swap Caption 02:36
Baby It's Cold Outside - Gender Swap Caption
Sissy Caption Story - Father Vs BBC Bully Cagefight 09:19
Sissy Caption Story - Father Vs BBC Bully Cagefight
Swan Song - Gender Swap Caption Story 21:21
Swan Song - Gender Swap Caption Story
Sissy Caption Story - Estranged Uncle 10:15
Sissy Caption Story - Estranged Uncle
Girlfriend For The Weekend - Caption Story 16:03
Girlfriend For The Weekend - Caption Story
Hazard Pay - Caption Story 08:26
Hazard Pay - Caption Story
Sex Slave - Caption Story 09:59
Sex Slave - Caption Story
Girlfriends Job - Caption Story 23:04
Girlfriends Job - Caption Story
Sissy Caption - Time To Pay The Rent 08:48
Sissy Caption - Time To Pay The Rent
Basketball Cheerleader - A Sissy Caption Story 03:20
Basketball Cheerleader - A Sissy Caption Story
Extra Cash - Caption Story 11:24
Extra Cash - Caption Story
Doctors Visit - A Sissy Caption Story Gender Swap Pill 11:59
Doctors Visit - A Sissy Caption Story Gender Swap Pill
Costume Contest - Sissy Story 03:03
Costume Contest - Sissy Story
BNWO Hypno - Whiteboy Castration - No Captions 05:26
BNWO Hypno - Whiteboy Castration - No Captions
Repaying The Debt Part I - A Sissy Caption Hentai Story 04:42
Repaying The Debt Part I - A Sissy Caption Hentai Story
Snowbunny Conversion - Overwatch BBC Caption Story 04:20
Snowbunny Conversion - Overwatch BBC Caption Story
Bachelor Party - Sissy Caption Story Porn 08:29
Bachelor Party - Sissy Caption Story Porn
Through The Eyes Of A BBC Queen - A Female POV BBC Caption Story 08:06
Through The Eyes Of A BBC Queen - A Female POV BBC Caption Story
Boss's Son - Sissy Caption Story Porn 09:06
Boss's Son - Sissy Caption Story Porn
BBC XChange Stories - Sissy Caption Story Porn 12:11
BBC XChange Stories - Sissy Caption Story Porn
Wife's Ex - Sissy Caption Story Porn 10:54
Wife's Ex - Sissy Caption Story Porn
The Promotion - Sissy Caption Story Porn 25:08
The Promotion - Sissy Caption Story Porn
Pawnstars - Sissy Caption Story Porn 07:17
Pawnstars - Sissy Caption Story Porn
XChange Star - Sissy Caption Story Porn 32:57
XChange Star - Sissy Caption Story Porn
Sissy Is forced To Visit - Caption Story PMV 29:39
Sissy Is forced To Visit - Caption Story PMV
Divorced - Sissy Caption Story Porn 28:52
Divorced - Sissy Caption Story Porn
Crazy For Cock - Sissy Caption Story Porn 12:44
Crazy For Cock - Sissy Caption Story Porn
Last Night - Sissy Caption Story Porn 09:08
Last Night - Sissy Caption Story Porn
BNWO - Whiteboy Officers 05:32
BNWO - Whiteboy Officers
Fitness Training - Sissy Caption Story Porn 09:16
Fitness Training - Sissy Caption Story Porn
Hacker Problem - TG Caption Story 16:24
Hacker Problem - TG Caption Story
XChange Drug Testing Trials - Sissy Caption Story Porn 18:13
XChange Drug Testing Trials - Sissy Caption Story Porn
Empty Your Mind Whiteboy 27:54
Empty Your Mind Whiteboy
Her Valentine's Day - Bodyswap Caption Story 16:59
Her Valentine's Day - Bodyswap Caption Story
Your Brain Has Been Rewired & There Is No Going Back 01:00
Your Brain Has Been Rewired & There Is No Going Back
My First BBC Contact 1 - A Sissy Caption Story 03:59
My First BBC Contact 1 - A Sissy Caption Story
My First BBC Contact 2 - A Sissy Caption Story 04:58
My First BBC Contact 2 - A Sissy Caption Story
Sissy Caption - My Friend's Dare 03:51
Sissy Caption - My Friend's Dare
Acting Practice - Sissy Caption Story Porn 11:31
Acting Practice - Sissy Caption Story Porn
Your Friend's Story (Voiced Gender Swap Caption) 11:13
Your Friend's Story (Voiced Gender Swap Caption)
BBC Photography - Sissy Caption Story Porn 09:03
BBC Photography - Sissy Caption Story Porn
A Career Change - Gender Swap Caption 24:41
A Career Change - Gender Swap Caption
My Friend Is A Bully 05:59
My Friend Is A Bully
My Ex Tricked Me Into Becoming A Girl - And I Liked It - Pt 1 - X-Change Story 21:40
My Ex Tricked Me Into Becoming A Girl - And I Liked It - Pt 1 - X-Change Story
Become The Egirl You Always Wanted Sissy Caption 00:40
Become The Egirl You Always Wanted Sissy Caption
Just Hanging With The Boys Sissy Caption Story 01:00
Just Hanging With The Boys Sissy Caption Story
Your Wive's First BBC - BBC Propaganda 13:53
Your Wive's First BBC - BBC Propaganda
Your Work Friend Needs A Sissy Sex Ed Teacher - Sissy Caption Story By Accsissycaptions 03:42
Your Work Friend Needs A Sissy Sex Ed Teacher - Sissy Caption Story By Accsissycaptions
College Party - Sissy Caption Story 12:56
College Party - Sissy Caption Story
Corporate Surrender - Gender Swap Caption 16:11
Corporate Surrender - Gender Swap Caption
Wake Up A Sissy 01:56
Wake Up A Sissy
His DDLG Fantasy - Sublimehypno 10:21
His DDLG Fantasy - Sublimehypno
Sissy Caption Story - Bosses Orders 43:34
Sissy Caption Story - Bosses Orders
The Frat Slut - Sissy Caption Story 58:57
The Frat Slut - Sissy Caption Story
Wife's New Job - A Cuckold Caption Story 19:30
Wife's New Job - A Cuckold Caption Story
Sissy Forced To Gangbang - Caption Story PMV 25:01
Sissy Forced To Gangbang - Caption Story PMV
The Polybius Incident - Gender Swap Story 22:18
The Polybius Incident - Gender Swap Story
Carlos Now Carla Making Partner - Gender Swap Story 28:41
Carlos Now Carla Making Partner - Gender Swap Story
Evermore - An X Change Caption Story 06:03
Evermore - An X Change Caption Story
If Only - An X-Change Caption Story 16:36
If Only - An X-Change Caption Story
Brat - An X-Change Caption Story 11:59
Brat - An X-Change Caption Story
Brat - An X-Change Story - With Voice Over 11:59
Brat - An X-Change Story - With Voice Over
True Nature - BBC Sissy Caption Story 11:46
True Nature - BBC Sissy Caption Story
True Nature - BBC Sissy Caption Story 11:46
True Nature - BBC Sissy Caption Story
Sissy Maid - BBC Caption Story 23:09
Sissy Maid - BBC Caption Story
Roommate Sissification Part 1 08:21
Roommate Sissification Part 1
Roommate Sissification Part 2 13:04
Roommate Sissification Part 2
The Bully Kink 50:48
The Bully Kink
Ex Girlfriend - By LucyLuu 24:24
Ex Girlfriend - By LucyLuu
Date With Kylie - Strapon Caption Story 02:00
Date With Kylie - Strapon Caption Story
Turned Into Girl - Xchange Story 04:16
Turned Into Girl - Xchange Story
My New Sexy Body 05:38
My New Sexy Body
Rent And A Handy Friend - Gender Swap Caption Story 08:17
Rent And A Handy Friend - Gender Swap Caption Story
Naked News - BBC In Control - Caption Story 07:58
Naked News - BBC In Control - Caption Story
Mommy Fell In Love With My Bully 06:30
Mommy Fell In Love With My Bully
The Purple Pill 17:06
The Purple Pill
Suck And Serve - Sissy Caption Story 07:42
Suck And Serve - Sissy Caption Story
The Wager - Sissy Caption Story 05:56
The Wager - Sissy Caption Story
No Going Back - Sissy Caption Story 03:45
No Going Back - Sissy Caption Story
Size Doesnt Matter - Sissy Caption Story 08:41
Size Doesnt Matter - Sissy Caption Story
Yoga Session - Sissy Caption Story 22:42
Yoga Session - Sissy Caption Story
Epic- XChange - Movie - PMV Caption Story 03:43
Epic- XChange - Movie - PMV Caption Story
Sexual Journey Pt1 - Sissy Caption Story 15:00
Sexual Journey Pt1 - Sissy Caption Story
Caption Compilation 1 05:13
Caption Compilation 1
Who Are You 12:03
Who Are You
Who Are You - Part 1 12:15
Who Are You - Part 1
Who Are You - Part 3 11:08
Who Are You - Part 3
Getaway - Xchange Movie - Full 11:37
Getaway - Xchange Movie - Full
The Cleaner - Sissy Caption Story 11:44
The Cleaner - Sissy Caption Story
Test His Dick - Sissy Caption Story 06:58
Test His Dick - Sissy Caption Story
Snowed In - A Gender Swap Story 07:04
Snowed In - A Gender Swap Story
More Than David Can Chew - By Freakling1990 13:33
More Than David Can Chew - By Freakling1990
Wife Turns Husband - Sissy Caption Story 11:47
Wife Turns Husband - Sissy Caption Story
Cosplay Cumdump 15:06
Cosplay Cumdump
Bootleg Meds - BBstories 07:13
Bootleg Meds - BBstories
The Honey Trap - A Sissy Caption Story 13:05
The Honey Trap - A Sissy Caption Story
Futa Mom 1 - Oral Anal Light-Feminization And More - NovaJoi 23:35
Futa Mom 1 - Oral Anal Light-Feminization And More - NovaJoi
Erotic Audio - Sissy Bimbo Slut Training 25:16
Erotic Audio - Sissy Bimbo Slut Training
The Boss Ordered - Sissy Caption Story 15:52
The Boss Ordered - Sissy Caption Story
Party Favor 00:57
Party Favor
Hottest Sissy Caption Compilation 10:57
Hottest Sissy Caption Compilation
Sissy Caption Story - Good Flatmates Part 1 By LucyLuu 12:10
Sissy Caption Story - Good Flatmates Part 1 By LucyLuu
Chikas School Valentine - By RatedF4Futa 08:48
Chikas School Valentine - By RatedF4Futa
Early Christmas 01:00
Early Christmas
Whitened Chocolate - Sissy Caption Story 05:41
Whitened Chocolate - Sissy Caption Story
Mommy Sissy And Bully 09:03
Mommy Sissy And Bully
Daddy Loves Me 2 - Sissy Life - Full Video By Sissypsichology 18:35
Daddy Loves Me 2 - Sissy Life - Full Video By Sissypsichology
Sissy Story - Daddys Girl 36:24
Sissy Story - Daddys Girl
New Roommate 00:34
New Roommate
Daddy Issues 14:04
Daddy Issues
Sissy Story - The Club 08:14
Sissy Story - The Club
Ex BBC Story Movie 16:00
Ex BBC Story Movie
Virtual Whore Immersion Training 02:31
Virtual Whore Immersion Training
Its Just Twister 01:16
Its Just Twister
Sissy Story - The Earth Needs Women 12:40
Sissy Story - The Earth Needs Women
Becoming A Big Cock Slut 03:47
Becoming A Big Cock Slut
Deal With Dealer 01:47
Deal With Dealer
My Girlfriend Teaches Me Female Orgasms Pt 1 16:55
My Girlfriend Teaches Me Female Orgasms Pt 1
Deal With Dealer 2 00:54
Deal With Dealer 2
Bully - Sissy Caption Story 15:38
Bully - Sissy Caption Story
You Are Her - Sissy PMV Caption Story 03:47
You Are Her - Sissy PMV Caption Story
Good Sissy Girl For Me 00:29
Good Sissy Girl For Me
My New Role Is In The BNWO 05:28
My New Role Is In The BNWO
Law and Order - Dick Sucking Unit 08:10
Law and Order - Dick Sucking Unit
A Day With Your Neighbor 03:05
A Day With Your Neighbor
Helping Out The Sports Team 00:35
Helping Out The Sports Team
Friendly Town - Hayley Taking Over 04:36
Friendly Town - Hayley Taking Over
Futa Petplay Orgasm - Hentai Dildo Hero, Anal Orgasm JOI 35:19
Futa Petplay Orgasm - Hentai Dildo Hero, Anal Orgasm JOI
Truth Or Dare - The Night You Became Their Sissy - Part 1 11:09
Truth Or Dare - The Night You Became Their Sissy - Part 1
The Blowjob Contest - Sissy Story 08:51
The Blowjob Contest - Sissy Story
TG Short N1 - Happy Birthday To Me - Sissy Story 06:42
TG Short N1 - Happy Birthday To Me - Sissy Story
Now Youre Just Another Weak Helpless Sissy 05:57
Now Youre Just Another Weak Helpless Sissy
Body Swap Shock - Caption Story 12:31
Body Swap Shock - Caption Story
You Are Overreacting 00:35
You Are Overreacting
How I Became Addicted To Cock Part 1 08:00
How I Became Addicted To Cock Part 1
Blowjob Queen - A Sissy Caption Story 11:46
Blowjob Queen - A Sissy Caption Story
Sissy Hacker Part 1 - JOI CEI Babecock Reveal Roulette 26:01
Sissy Hacker Part 1 - JOI CEI Babecock Reveal Roulette
How My Own Viewers Turned Me Into The Sissy - Part 1 06:45
How My Own Viewers Turned Me Into The Sissy - Part 1
Futa Plumber Fuck - Anal Footjob Dildo Hero JOI 15:42
Futa Plumber Fuck - Anal Footjob Dildo Hero JOI
Prison Sissy Pimped Out - Comic Narration 14:20
Prison Sissy Pimped Out - Comic Narration
Sissy Breaks The Internet 15:09
Sissy Breaks The Internet
Futa Kafka Makes You Her Pet - Preview - NovaJoi 10:58
Futa Kafka Makes You Her Pet - Preview - NovaJoi
Hypnotic Catch - Caption Story 04:08
Hypnotic Catch - Caption Story
BBC Sloppy Toppy 11:00
BBC Sloppy Toppy
Your Bully Fucks You 01:03
Your Bully Fucks You
How My Trainer Turned Me Into His Sissy - Part 1 08:43
How My Trainer Turned Me Into His Sissy - Part 1
Your Girly Yoga Day - BBC XChange Story By FloraSissy 26:16
Your Girly Yoga Day - BBC XChange Story By FloraSissy
Beta Test 01:00
Beta Test
Size Competition 01:00
Size Competition
The Favour - HypnoSister 18:59
The Favour - HypnoSister
Sorority Sister 01:00
Sorority Sister
All Girls College 01:00
All Girls College
Magic Spell 01:00
Magic Spell
Turned Into A Femboy 01:00
Turned Into A Femboy
Sissy Lost In The Woods 01:00
Sissy Lost In The Woods
Turned To A Sissy By GF 01:00
Turned To A Sissy By GF
Youre Married But He Made You His Sissy Anyway 00:59
Youre Married But He Made You His Sissy Anyway
The Janitor 00:50
The Janitor
Xchange Law 05:16
Xchange Law
Bimbo Nightmares - A Sissy Caption Story 21:00
Bimbo Nightmares - A Sissy Caption Story
Roommate Sharing His Cock 00:48
Roommate Sharing His Cock
Extortion Anything To Win - Caption Story 13:42
Extortion Anything To Win - Caption Story
You Want To Become Her - N1 - Sissy Caption Story 04:05
You Want To Become Her - N1 - Sissy Caption Story
Cosplay Xchange 08:21
Cosplay Xchange
Sissy Shorts - Tattoo 00:52
Sissy Shorts - Tattoo
When Pranks Go Too Far - Pt 1 06:02
When Pranks Go Too Far - Pt 1
90 Days In Jail Broke My Masculinity Part 1 07:44
90 Days In Jail Broke My Masculinity Part 1
Nanobot Shape Shifter 06:59
Nanobot Shape Shifter
Im Not Gay I Was Drunk 00:35
Im Not Gay I Was Drunk
Investigation - Sissy Caption Story 17:44
Investigation - Sissy Caption Story
Dont Deal With The Cartel Part 1 - A Sissy Caption Story 07:45
Dont Deal With The Cartel Part 1 - A Sissy Caption Story
Dont Deal with the Cartel Part 2 - A Sissy Caption Story 10:26
Dont Deal with the Cartel Part 2 - A Sissy Caption Story
Tough Times - Caption Story 13:35
Tough Times - Caption Story
Helping A Friend 00:39
Helping A Friend
Sissy Loves BBC 01:00
Sissy Loves BBC
Paying Daddys Debt 01:00
Paying Daddys Debt
Sissy Life - You Are A Cock Addict 03:22
Sissy Life - You Are A Cock Addict
Keeping Secrets 10:02
Keeping Secrets
How I Got Tricked Into Sissy Training Part 1 07:30
How I Got Tricked Into Sissy Training Part 1
Wake Up Call Sissy 00:44
Wake Up Call Sissy
The Fill In - Caption Story 13:13
The Fill In - Caption Story
Shrinking Consequence 09:03
Shrinking Consequence
Wrong School Of Thought - A Sissy Caption Story 08:57
Wrong School Of Thought - A Sissy Caption Story
Dress - Sissy Caption Story 15:36
Dress - Sissy Caption Story
Double Trouble Part 1 - A Sissy Caption Story 08:57
Double Trouble Part 1 - A Sissy Caption Story
Double Trouble Part 2 - A Sissy Caption Story 11:45
Double Trouble Part 2 - A Sissy Caption Story
Your Bully - Captions Story 16:50
Your Bully - Captions Story
Roommate - Sissy Caption Story 10:16
Roommate - Sissy Caption Story
Sneaking Into Yoga - A Sissy Caption Story 07:43
Sneaking Into Yoga - A Sissy Caption Story
Sissy Vision 02:31
Sissy Vision
I Knew You Are A Girl - TG Caption Story 19:16
I Knew You Are A Girl - TG Caption Story
How Game Night Turned Me Into A Sissy - Part 1 06:23
How Game Night Turned Me Into A Sissy - Part 1
License To Swallow - Bimbo Files N001 - A Sissy Caption Story 28:10
License To Swallow - Bimbo Files N001 - A Sissy Caption Story
Undercover Sissy Detective - Caption Story 05:24
Undercover Sissy Detective - Caption Story
Bottom For Futa Polycule - JOI 17:00
Bottom For Futa Polycule - JOI
From Denial To Addiction 03:00
From Denial To Addiction
Baldurs Gate Cosplay Contest 13:36
Baldurs Gate Cosplay Contest
Space Cum Eating Training JOI - Voiced And Captions 07:59
Space Cum Eating Training JOI - Voiced And Captions
Sucked It For Hours And Cant Get Enough - Turkish 02:20
Sucked It For Hours And Cant Get Enough - Turkish
Youve Never Been A Man - Turkish 02:20
Youve Never Been A Man - Turkish
Neighborhood Slut 00:50
Neighborhood Slut
Fuck Your Brain 02:20
Fuck Your Brain
No Way Back N3 - Sissy Caption Story 06:47
No Way Back N3 - Sissy Caption Story
Just Look How Far Youve Come Sissy 00:49
Just Look How Far Youve Come Sissy
Good Bimbo Deep Loop Conditioning Program 08:50
Good Bimbo Deep Loop Conditioning Program

90 Days In Jail Broke My Masculinity Part 1

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SissyBenefits Submitted by SissyBenefits
  • 07:44
  • 70769
  • 2025-04-15 02:34:14
How 90 days in jail turned me into a sissy
Tags: SissyTraining, Feminization, SissySlut, SubmissiveSissy, ForcedFeminization , SissyMindBreak, ReluctantSissy, HypnoSissy, jail
Categories: Big Cock, Caption Story, Captions, Cock Sucking, Feminization, Movies
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