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Sissy Entrapment 06:11
Sissy Entrapment
Black Magic Sissy Transformation 07:22
Black Magic Sissy Transformation
Pretty Prison 09:00
Pretty Prison
Sissy MENtors - By Drogon 31:46
Sissy MENtors - By Drogon
A Sissy Life Movie - The Best Room Mate 08:06
A Sissy Life Movie - The Best Room Mate
Perverted Meditations - Glory Hole Slut 10:52
Perverted Meditations - Glory Hole Slut
Perverted Meditations - 24 Hours as a Shemale 12:41
Perverted Meditations - 24 Hours as a Shemale
Mortus Girls - On The Hook - Chapter 1 - [English] 11:07
Mortus Girls - On The Hook - Chapter 1 - [English]
Mortus Girls - On The Hook - Chapter 2 - English 13:05
Mortus Girls - On The Hook - Chapter 2 - English
Vol 1 Of ChloeCaps 11:50
Vol 1 Of ChloeCaps
How I Became A Sissy - Part 1 25:07
How I Became A Sissy - Part 1
No Looking Back - Gender Swap Caption 03:45
No Looking Back - Gender Swap Caption
Swan Song - Gender Swap Caption Story 21:21
Swan Song - Gender Swap Caption Story
Sissy Caption Story - White Cocks Matter 07:53
Sissy Caption Story - White Cocks Matter
How I Became A Sissy - Part 2 33:22
How I Became A Sissy - Part 2
Almost Home Alone - A PoisonSissy Story 20:21
Almost Home Alone - A PoisonSissy Story
Gloryhole Surprise Party 08:39
Gloryhole Surprise Party
Caught And Turned Into A Sissy Cock Slut 08:07
Caught And Turned Into A Sissy Cock Slut
Sissy Caption Story - 1 Month 1/2 12:57
Sissy Caption Story - 1 Month 1/2
Girlfriend For The Weekend - Caption Story 16:03
Girlfriend For The Weekend - Caption Story
Hazard Pay - Caption Story 08:26
Hazard Pay - Caption Story
Reverse the Curse - Gender Swap Story - Episode 1 18:11
Reverse the Curse - Gender Swap Story - Episode 1
Gender Studies - Male To Female Transformation Caption Movie 1:07:30
Gender Studies - Male To Female Transformation Caption Movie
Vlogging The Real Me - Caption Story 08:13
Vlogging The Real Me - Caption Story
Making The Team - Gender Swap Caption 12:22
Making The Team - Gender Swap Caption
YVN90 - At The Bar 11:15
YVN90 - At The Bar
Lost A Bet 09:56
Lost A Bet
Sissy Caption Story - Bad Deal 14:45
Sissy Caption Story - Bad Deal
Sound Advice 12:28
Sound Advice
Girlfriends Job - Caption Story 23:04
Girlfriends Job - Caption Story
Sissy Squad - Field Testing - Sissy Caption Story 12:26
Sissy Squad - Field Testing - Sissy Caption Story
Sissy Psychosis - Sissy Caption Story 16:08
Sissy Psychosis - Sissy Caption Story
YV90 - New Models 07:09
YV90 - New Models
Sissy Caption Story - Trippy Days 19:31
Sissy Caption Story - Trippy Days
The Semester 23:53
The Semester
Extra Cash - Caption Story 11:24
Extra Cash - Caption Story
Undercover - Caption Story 17:24
Undercover - Caption Story
Born This Way 17:36
Born This Way
Doctors Visit - A Sissy Caption Story Gender Swap Pill 11:59
Doctors Visit - A Sissy Caption Story Gender Swap Pill
Acting Like A Slut - Caption Story 21:24
Acting Like A Slut - Caption Story
Sissy Island - Sissy Caption Story Porn 13:36
Sissy Island - Sissy Caption Story Porn
Repaying The Debt Part I - A Sissy Caption Hentai Story 04:42
Repaying The Debt Part I - A Sissy Caption Hentai Story
Bachelor Party - Sissy Caption Story Porn 08:29
Bachelor Party - Sissy Caption Story Porn
Mechanic Dare - Sissy Caption Story Porn 06:16
Mechanic Dare - Sissy Caption Story Porn
Forced Sissy Caption Story PMV 32:04
Forced Sissy Caption Story PMV
Protective Proof 11:00
Protective Proof
Stupid Drunk Dares - Sissy Caption Story Porn 09:40
Stupid Drunk Dares - Sissy Caption Story Porn
Boss's Son - Sissy Caption Story Porn 09:06
Boss's Son - Sissy Caption Story Porn
My Better Half 11:50
My Better Half
Generex - The Conversion 30:33
Generex - The Conversion
Wife's Ex - Sissy Caption Story Porn 10:54
Wife's Ex - Sissy Caption Story Porn
Protective Proof Pt 2 08:45
Protective Proof Pt 2
Protective Proof Pt 3 13:28
Protective Proof Pt 3
Generex - Too Horny? 23:08
Generex - Too Horny?
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
Divorced - Sissy Caption Story Porn 28:52
Divorced - Sissy Caption Story Porn
Reverse the Curse - Gender Swap Story - Episode 2 35:55
Reverse the Curse - Gender Swap Story - Episode 2
Crazy For Cock - Sissy Caption Story Porn 12:44
Crazy For Cock - Sissy Caption Story Porn
Gender Swap Game Show 35:13
Gender Swap Game Show
Last Night - Sissy Caption Story Porn 09:08
Last Night - Sissy Caption Story Porn
Hotel With A Friend 04:55
Hotel With A Friend
Proving To Him That I'm A Girl 14:27
Proving To Him That I'm A Girl
Fitness Training - Sissy Caption Story Porn 09:16
Fitness Training - Sissy Caption Story Porn
The Long Turn - Sissy Caption Story Porn 46:26
The Long Turn - Sissy Caption Story Porn
Hacker Problem - TG Caption Story 16:24
Hacker Problem - TG Caption Story
My Brother's Buddy's Cock - A Sissy Story 09:53
My Brother's Buddy's Cock - A Sissy Story
Curious Boy Got Hacked - A Caption Story 05:16
Curious Boy Got Hacked - A Caption Story
Sissy Caption Story - Prisoners Pt 2 10:07
Sissy Caption Story - Prisoners Pt 2
A Loving Cuckold Story 30:18
A Loving Cuckold Story
Becoming Her 13:40
Becoming Her
Bullied By BBC Forever 2 - A Sissy Caption Story 13:23
Bullied By BBC Forever 2 - A Sissy Caption Story
The Switch 08:41
The Switch
Sissy Caption - Lost A Bet 08:42
Sissy Caption - Lost A Bet
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
The Adventures Of A Cum Sucking Sissy Succubus 09:58
The Adventures Of A Cum Sucking Sissy Succubus
Your Friend's Story (Voiced Gender Swap Caption) 11:13
Your Friend's Story (Voiced Gender Swap Caption)
Undercover Sissy - Sissy Caption Story Porn 41:39
Undercover Sissy - Sissy Caption Story Porn
BBC Photography - Sissy Caption Story Porn 09:03
BBC Photography - Sissy Caption Story Porn
How My Life Looks Like As A Cocksucker Part 1 06:18
How My Life Looks Like As A Cocksucker Part 1
A Career Change - Gender Swap Caption 24:41
A Career Change - Gender Swap Caption
Bullied By BBC Forever 3 - A Sissy Caption Story 22:20
Bullied By BBC Forever 3 - A Sissy Caption Story
My Friend Is A Bully 05:59
My Friend Is A Bully
Maid Prank Gone Right - Sissy Caption Story - Sublimehypno 15:41
Maid Prank Gone Right - Sissy Caption Story - Sublimehypno
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
My Ex Tricked Me Into Becoming A Girl - And I Liked It - Pt 2 - X-Change Story 17:17
My Ex Tricked Me Into Becoming A Girl - And I Liked It - Pt 2 - X-Change Story
My Ex Tricked Me Into Becoming A Girl - And I Liked It - Pt 3 - X-Change Story 16:15
My Ex Tricked Me Into Becoming A Girl - And I Liked It - Pt 3 - X-Change Story
Training To Go Undercover - Sissy Caption Story By S44int 16:31
Training To Go Undercover - Sissy Caption Story By S44int
College Party - Sissy Caption Story 12:56
College Party - Sissy Caption Story
Relapse On Sissy Pills 11:25
Relapse On Sissy Pills
Frustrated Friend Part 1 - A Sissy Caption Story 12:56
Frustrated Friend Part 1 - A Sissy Caption Story
Part 3 12:31
Part 3
Boyfriend To E-Girl - Sissy Caption Story 26:28
Boyfriend To E-Girl - Sissy Caption Story
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
Football Bet - Sissy Story 23:33
Football Bet - Sissy Story
Wife's New Job - A Cuckold Caption Story 19:30
Wife's New Job - A Cuckold Caption Story
Wrong Drug Part 2 - A Sissy Caption Story - SissyFan 12:02
Wrong Drug Part 2 - A Sissy Caption Story - SissyFan
The Office - Part One 17:00
The Office - Part One
Carlos Now Carla Making Partner - Gender Swap Story 28:41
Carlos Now Carla Making Partner - Gender Swap Story
Swap Tales - Getting Even 14:39
Swap Tales - Getting Even
Who Wants To Be A Girl - Sissy Caption Story 29:47
Who Wants To Be A Girl - Sissy 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
Christmas Gifts - Sissy Caption Story 16:21
Christmas Gifts - Sissy Caption Story
Hypnosister - The Prank - Trans Edition 11:43
Hypnosister - The Prank - Trans Edition
Hypnosister - The Prank - Standard Edition 16:39
Hypnosister - The Prank - Standard Edition
True Nature - BBC Sissy Caption Story 11:46
True Nature - BBC Sissy Caption Story
Hypnosister - The Fancy Dress Party 12:42
Hypnosister - The Fancy Dress Party
Dream Job - Sissy Caption Story 18:17
Dream Job - Sissy Caption Story
Occult Sissy Story 14:11
Occult Sissy Story
Ex Girlfriend - By LucyLuu 24:24
Ex Girlfriend - By LucyLuu
Overslept - Sissy Caption Story 11:18
Overslept - Sissy Caption Story
Steve Now Sveta - X-Change Story 26:43
Steve Now Sveta - X-Change Story
One Mistake Part 1 - A Sissy Caption Story 15:08
One Mistake Part 1 - A Sissy Caption Story
John Now Leah - Chapter 2 09:52
John Now Leah - Chapter 2
Hypnosister - Locked Up 12:28
Hypnosister - Locked Up
Hypnosister - Camslut 15:56
Hypnosister - Camslut
Grindr Date Night - A Sissy Caption Movie By Sublimehypno 15:34
Grindr Date Night - A Sissy Caption Movie By Sublimehypno
Almost Like Jail - Sissy Caption Story By S44int 14:17
Almost Like Jail - Sissy Caption Story By S44int
Meeting My Mistress 05:13
Meeting My Mistress
Hypnosister - Roommate Wanted 21:56
Hypnosister - Roommate Wanted
My Mothers Friend - Sissy Caption Story 06:29
My Mothers Friend - Sissy Caption Story
My Fathers Friend - Sissy Caption Story 06:16
My Fathers Friend - Sissy Caption Story
Sissy Slut Confession - Caption Story 08:45
Sissy Slut Confession - Caption Story
The Bad Batch - A Caption Dub From Captivatrix 16:16
The Bad Batch - A Caption Dub From Captivatrix
How I Became A Femboy Whore 07:51
How I Became A Femboy Whore
Friend In Need 20:29
Friend In Need
Hypnosister - The Anniversary 19:37
Hypnosister - The Anniversary
The Good Son 12:50
The Good Son
Sissy Dreams - Hitchhiker 07:44
Sissy Dreams - Hitchhiker
Sissy Dreams - Hitchhiker Part 2 24:41
Sissy Dreams - Hitchhiker Part 2
Hypnosister - The Bet 2 17:22
Hypnosister - The Bet 2
Making The Sale - Sissy Story 12:29
Making The Sale - Sissy Story
My Wife Found Out Everything - Sissy Caption Story 17:59
My Wife Found Out Everything - Sissy Caption Story
Rent And A Handy Friend - Gender Swap Caption Story 08:17
Rent And A Handy Friend - Gender Swap Caption Story
X-Change - An Anal Story 13:55
X-Change - An Anal Story
Onedollarsissy - Sissy In Distress 08:27
Onedollarsissy - Sissy In Distress
Occult Story 2 19:35
Occult Story 2
Confronting Your Bully - Sissy Caption Movie 16:51
Confronting Your Bully - Sissy Caption Movie
Sissy Swim Class - Sissy Caption Story 46:27
Sissy Swim Class - Sissy Caption Story
Yoga Session - Sissy Caption Story 22:42
Yoga Session - Sissy Caption Story
BBC Xchange 14:56
BBC Xchange
Captured And Trained - Sissy Caption Story - Part 1 11:42
Captured And Trained - Sissy Caption Story - Part 1
Extreme Anal Gangbang Caption Story - No Music 47:08
Extreme Anal Gangbang Caption Story - No Music
The Pillory - Hypnosister 17:44
The Pillory - Hypnosister
I Need A Ride 12:27
I Need A Ride
Sissys Salty Revenge 12:44
Sissys Salty Revenge
Sissy Story - Master Class 12:21
Sissy Story - Master Class
How I Became A Femboy Porn Star - Part 1 22:08
How I Became A Femboy Porn Star - Part 1
Carries sissy journey Part 1 27:00
Carries sissy journey Part 1
New Photo Model - Sissy Caption Story 15:27
New Photo Model - Sissy Caption Story
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
Sweet Gift - Sissy Caption Story 14:45
Sweet Gift - Sissy Caption Story
The Kink - Sissy Caption Story - Part 1 27:27
The Kink - Sissy Caption Story - Part 1
The Kink - Sissy Caption Story - Part 2 34:49
The Kink - Sissy Caption Story - Part 2
The Cleaner - Sissy Caption Story 11:44
The Cleaner - Sissy Caption Story
Caught In The Act - A Sissy Caption Story 12:35
Caught In The Act - A Sissy Caption Story
Snowed In - A Gender Swap Story 07:04
Snowed In - A Gender Swap Story
Carries Sissy Journey - Part 2 38:18
Carries Sissy Journey - Part 2
Cosplay Cumdump 15:06
Cosplay Cumdump
Kai Forced Into Kaylee - X-Change Story 10:56
Kai Forced Into Kaylee - X-Change Story
The Honey Trap - A Sissy Caption Story 13:05
The Honey Trap - A Sissy Caption Story
How My Hubby Became A Sissy 34:56
How My Hubby Became A Sissy
Sissy Caption Story - Good Flatmates Part 1 By LucyLuu 12:10
Sissy Caption Story - Good Flatmates Part 1 By LucyLuu
How I Became a Permanent Sissy Part 1 13:23
How I Became a Permanent Sissy Part 1
The Dark Web Pill 21:05
The Dark Web Pill
Sissy Breaks The Internet 15:09
Sissy Breaks The Internet
Bimbo Nightmares - A Sissy Caption Story 21:00
Bimbo Nightmares - A Sissy Caption Story
Extortion Anything To Win - Caption Story 13:42
Extortion Anything To Win - Caption Story

Sissy Caption Story - Bosses Orders

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  • (92)
  • 43:34
  • 102303
  • 2023-07-16 22:59:44
Sissy is a secretary at a film studio after college when his student loan debt starts piling up. Sissy's boss promises to pay off sissy's debt if sissy takes Xchange for 12 months. After reluctantly taking Xchange, sissy becomes even more submissive, is treated like a girl and dominated by her boss. Sissy gives boss a little attitude at first to see how dominant he is but learns quickly learns her place and likes it. She becomes a live in girlfriend for the boss by the end.
Categories: Caption Story, Movies

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