Network: Announcements Hypnotube Discord Support Hypnotube's Creator Friends More
Home - Hypnotube Beta
Upload
Help Hypnomaster build online games
Sissy
1549 views
0% (0)
Sissy Training - Repeat After Me 07:00
Sissy Training - Repeat After Me
Secret Sissy 05:45
Secret Sissy
A Day In The Life 10:12
A Day In The Life
Know Your Place 10:44
Know Your Place
Drill Me Down 04:47
Drill Me Down
Reverse Hypnosis - SisWen 04:10
Reverse Hypnosis - SisWen
Sex Doll 07:52
Sex Doll
That's My Girl 04:50
That's My Girl
Night Shift 12:34
Night Shift
Sissy Challenge - Pimped Out 06:32
Sissy Challenge - Pimped Out
The Sissy Cum Slut Mantra 06:18
The Sissy Cum Slut Mantra
Bimbo Doll Program v2 44:12
Bimbo Doll Program v2
Abuse Doll 12:21
Abuse Doll
Hungry Hypno 06:29
Hungry Hypno
Being The Girl Hypno 11:37
Being The Girl Hypno
A Sissy's First Time 10:45
A Sissy's First Time
Swan Song - Gender Swap Caption Story 21:21
Swan Song - Gender Swap Caption Story
Sissy Cock Roulette Ep 5 25:34
Sissy Cock Roulette Ep 5
Sissy Hacker Part 2 - JOI CEI Babecock Reveal Roulette 13:19
Sissy Hacker Part 2 - JOI CEI Babecock Reveal Roulette
Sissy Caption Story - 1 Month 2 Of 2 16:20
Sissy Caption Story - 1 Month 2 Of 2
Sex Slave - Caption Story 09:59
Sex Slave - Caption Story
Suck Cock PMV 07:12
Suck Cock PMV
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
Pink - Feminizer Censored Sissy Safe - Bimbo Labs 06:47
Pink - Feminizer Censored Sissy Safe - Bimbo Labs
Undercover Sissy - Sissy Caption Story Porn 41:39
Undercover Sissy - Sissy Caption Story Porn
A Career Change - Gender Swap Caption 24:41
A Career Change - Gender Swap Caption
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
YOU ARE JUST A FUCK DOLL /HYPNODANCER/ 05:26
YOU ARE JUST A FUCK DOLL /HYPNODANCER/
Training To Go Undercover - Sissy Caption Story By S44int 16:31
Training To Go Undercover - Sissy Caption Story By S44int
Corporate Surrender - Gender Swap Caption 16:11
Corporate Surrender - Gender Swap Caption
Boyfriend To E-Girl - Sissy Caption Story 26:28
Boyfriend To E-Girl - Sissy Caption Story
Finally Accept Her Fate 05:39
Finally Accept Her Fate
Turning Into Sissy Slave - Gender Swap 04:33
Turning Into Sissy Slave - Gender Swap
Warrior Princess Becoming Slave By Dark Magic 06:08
Warrior Princess Becoming Slave By Dark Magic
Forced Into Prostitution 08:58
Forced Into Prostitution
Captured And Fucked Until You Became A Slave 05:09
Captured And Fucked Until You Became A Slave
Breaking Of The Sissy Part 1 Of 2 05:30
Breaking Of The Sissy Part 1 Of 2
Accept Yourself - PMV By HoloPMV 02:06
Accept Yourself - PMV By HoloPMV
Size Doesnt Matter - Sissy Caption Story 08:41
Size Doesnt Matter - Sissy Caption Story
Kidnapped And Trained - A Sissy Caption Story 03:02
Kidnapped And Trained - A Sissy Caption Story
Captured And Trained - Sissy Caption Story - Part 1 11:42
Captured And Trained - Sissy Caption Story - Part 1
Wana To Be - PMV By HoloPMV 02:08
Wana To Be - PMV By HoloPMV
Captured And Trained - Sissy Caption Story - Part 2 38:55
Captured And Trained - Sissy Caption Story - Part 2
Feminization Brainwash - Poppers HMV 10:39
Feminization Brainwash - Poppers HMV
Sexual Journey Pt1 - Sissy Caption Story 15:00
Sexual Journey Pt1 - Sissy Caption Story
Caught In The Act - A Sissy Caption Story 12:35
Caught In The Act - A Sissy Caption Story
Cosplay Cumdump 15:06
Cosplay Cumdump
The Boss Ordered - Sissy Caption Story 15:52
The Boss Ordered - Sissy Caption Story
Hottest Sissy Caption Compilation 10:57
Hottest Sissy Caption Compilation
How My Trainer Turned Me Into His Sissy - Part 1 08:43
How My Trainer Turned Me Into His Sissy - Part 1
90 Days In Jail Broke My Masculinity Part 1 07:44
90 Days In Jail Broke My Masculinity Part 1
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
Role Rewind - A Sissy Caption Story 04:45
Role Rewind - A Sissy Caption Story
How I Got Tricked Into Sissy Training Part 1 07:30
How I Got Tricked Into Sissy Training Part 1
The Fill In - Caption Story 13:13
The Fill In - 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
Too Realistic- Sissy Caption Story 17:06
Too Realistic- Sissy Caption Story
TV Night - Sissy Caption Story 04:11
TV Night - Sissy Caption Story
Role Rewind 2 - A Sissy Caption Story 10:44
Role Rewind 2 - A Sissy Caption Story
Altered Deal Part 1 - A Sissy Caption Story 08:10
Altered Deal Part 1 - A Sissy Caption Story
Altered Deal Part 2 - A Sissy Caption Story 09:28
Altered Deal Part 2 - A Sissy Caption Story
The Roommate Setup - A Sissy Caption Story 15:04
The Roommate Setup - A Sissy Caption Story
Good Girl - Sissy Caption Story 15:56
Good Girl - Sissy Caption Story
Total Goon Doll Download 02:23
Total Goon Doll Download
Cocksucker Dreams 04:09
Cocksucker Dreams
Neighbor Makes You His Personal Sex Toy 00:46
Neighbor Makes You His Personal Sex Toy
Caught At A Convention 02:32
Caught At A Convention
You Asked Your Roommate For A Friendly Wrestling 00:34
You Asked Your Roommate For A Friendly Wrestling
The Antidote - Caption Story 10:15
The Antidote - Caption Story
Sissy Facefucked For A Stupid Question 00:42
Sissy Facefucked For A Stupid Question
Fulfilling His Demands Pt1 - Sissy Caption Story 10:25
Fulfilling His Demands Pt1 - Sissy Caption Story
Dont Drink Too Much - A Sissy Caption Story 05:08
Dont Drink Too Much - A Sissy Caption Story
Sissy Manhandled 00:58
Sissy Manhandled
Becoming My Roommates Toy - A Sissy Caption Story 09:40
Becoming My Roommates Toy - A Sissy Caption Story
Sissy Cant Resist Hypno 00:42
Sissy Cant Resist Hypno
Sissy Gets Caught And Facefucked 00:50
Sissy Gets Caught And Facefucked
Sissy Got Broken 00:38
Sissy Got Broken
Sissy Hypnotized To Be A Fleshlight 00:47
Sissy Hypnotized To Be A Fleshlight
Will You Accept This Deal 01:00
Will You Accept This Deal
Gender Swap Pill Makes You Cock Dumb 00:36
Gender Swap Pill Makes You Cock Dumb
You Love To Be Manhandled 00:36
You Love To Be Manhandled
XChange Addiction - Sissy Caption Story 58:25
XChange Addiction - Sissy Caption Story
Sissys Fall On Stream 01:00
Sissys Fall On Stream
Sissy Got Blackmailed 00:46
Sissy Got Blackmailed
Lesson Learned - A Sissy Caption Story 01:23
Lesson Learned - A Sissy Caption Story
PussyLicker - Sissy Story Tales - Xella 20:50
PussyLicker - Sissy Story Tales - Xella
A Compliant Husband - Sissy Story Tales - Xella 12:42
A Compliant Husband - Sissy Story Tales - Xella
BodyHopper Problems - Sissy Story Tales - Xella 10:44
BodyHopper Problems - Sissy Story Tales - Xella
The Catch - A Sissy Caption Story 07:59
The Catch - A Sissy Caption Story
Sissy Submits To A Stranger 00:48
Sissy Submits To A Stranger
This Was Your Best Prank You Pulled On Your Roommate 01:00
This Was Your Best Prank You Pulled On Your Roommate

90 Days In Jail Broke My Masculinity Part 1

  • 76%
  • (109)
SissyBenefits Submitted by SissyBenefits
  • 07:44
  • 108134
  • 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
Show moreShow less

Comments (2)

Show moreShow less

You must be logged in to post wall comments. Please Login or Signup (free).

Related Content

How I Became a Permanent Sissy Part 1 13:23 HD How I Became a Permanent Sissy Part 1 84% 255391
90 Days Of Nipple Training 06:29 90 Days Of Nipple Training 40% 12898
HypnoSissy 08:06 HD HypnoSissy 92% 1516409
Toxic Masculinity 03:39 HD Toxic Masculinity 74% 70034
Now Youre Just Another Weak Helpless Sissy 05:57 HD Now Youre Just Another Weak Helpless Sissy 84% 144224
How A Trans Goddess Broke Me Part 1 09:00 HD How A Trans Goddess Broke Me Part 1 90% 147842
Queue-balls 21 Day Challenge - Stage 1 Days 1 & 2 23:42 HD Queue-balls 21 Day Challenge - Stage 1 Days 1 & 2 77% 54161
Voice Only Queue Balls Days 1 and 2 - Stage 1 23:42 HD Voice Only Queue Balls Days 1 and 2 - Stage 1 73% 15968
Queue Balls - Voice Emphasized Mix - Stage 1 - Days 1-6 Of 21 1:59:41 HD Queue Balls - Voice Emphasized Mix - Stage 1 - Days 1-6 Of 21 82% 53217
The Feminizer - Part 1 11:52 The Feminizer - Part 1 67% 630125
Will You Put Your Leash On Me? Photos: 1 Will You Put Your Leash On Me? 100% 2072
Three Days In Chicago Photos: 23 Three Days In Chicago 42% 3345
Sissy Slut Feeling Cute Photos: 5 Sissy Slut Feeling Cute 85% 3545
Fucking My Sissy Pussy 02:01 Fucking My Sissy Pussy 87% 47327
If We Ever Broke Up - Femboy HMV 02:21 HD If We Ever Broke Up - Femboy HMV 94% 151781
Virus Broke Your Head 02:00 HD Virus Broke Your Head 72% 31800
Guess Its Broke Photos: 1 Guess Its Broke 100% 297
2 Broke Girls 00:26 HD 2 Broke Girls 55% 7406
Ready Player One Trailer - By HypeArt 02:11 HD Ready Player One Trailer - By HypeArt 81% 47916
On Your Knees 03:36 HD On Your Knees 84% 28217
Masculinity Revoked 04:40 HD Masculinity Revoked 83% 142692
Almost Like Jail - Sissy Caption Story By S44int 14:17 HD Almost Like Jail - Sissy Caption Story By S44int 76% 33378
Sissy Prisoner 04:21 HD Sissy Prisoner 78% 87515
Sissy Training 1 - Feminization Or Why Are You A Girl 02:42 HD Sissy Training 1 - Feminization Or Why Are You A Girl 90% 78927