Network:
Announcements
Hypnotube Discord
Support Hypnotube's Creator
Friends
More
All Media
Videos
Images
Accounts
Playlists
Login
Free Registration
Sign Up
Upload
VIP
Videos
VIP Videos
VIP Rooms
VIP Rooms
Trending
Movies
Most Recent
Most Viewed
Top Rated
Most Discussed
Longest
Albums
Most Recent
Most Viewed
Top Rated
Most Discussed
Categories
Audio
Cock Sucking
Cum
Feminization
Fucking
Gifs
HD
Hypnosis
See All
Cams
AI Jerk Off
Reading
Playlists
sissy
3881 views
0% (0)
10:00
DeepSlutPuppy Episode 1
04:02
Sissy Love Games
08:47
Gemini PMV
37:32
Sissy Hypno Addiction 3
08:04
Thirsty Cum Slut
06:39
New Sissy Cum Trainer
14:32
Cumslut Training
15:14
Sissy Fuck Doll Trainer
10:54
Cum Princess
08:08
Straight Reverse Hypnosis 2
01:10
Ass up Face Down Sissy Boi
11:39
DeepSlutPuppy Episode 4
08:04
DeepSlutPuppy Episode 6 - Captions
02:48
Nasty Bitch
08:20
DeepSlutPuppy Cumversion
08:06
HypnoSissy
04:52
Naked Girls Don't Turn You On Anymore (Lesson 30)
04:03
My Sissy Bachelor Party Fantasy
06:18
Follow Your Dreams - Sissy Hypno Slut
20:38
Sissy World 7
18:06
Sissy World 2 - Sissy Progression
05:26
Throat Slave Love by Drogon
15:37
Sissy World 6 - ATM Sissy by Drogon
07:44
Role Models Are Important By Drogon
17:31
Sissy World 3 - Cum And Piss Trainer By Drogon
04:44
FriGGGa Sissymaker PMV 2020
12:43
Sissy Secrets By Drogon
31:46
Sissy MENtors - By Drogon
14:52
Sissy World 9
07:50
SissyMaker 9 - Breed Black PMV
03:31
Anal Whore Goals
21:57
Blowbang Sissy - By Drogon
12:01
Sissy World 1 - The First Ever Drogon Production
32:13
Next Level Sissy Challenge - By Drogon
27:36
BBC Broken - By Drogon
03:49
Plug Princess - Ass To Mouth Training v2
12:21
Abuse Doll
04:00
Your Mom's BBC Secret 4 (MONSTERCOCKGOD)
11:07
Mortus Girls - On The Hook - Chapter 1 - [English]
13:05
Mortus Girls - On The Hook - Chapter 2 - English
12:56
Take One For The Team
05:47
Submissive Sissy Bitch Boi Training
04:33
Gangbang Addiction PMV
22:14
Sissy World 10 by Drogon
01:40
Sissyarmy - Night With Friends Caption Story
17:11
Untitled By Drogon
20:32
Party Piss Whore
18:00
Cum Addict - By Drogon
12:22
Making The Team - Gender Swap Caption
26:38
Fem Bitch Boy
16:41
Ass To Mouth Sissy For Life - By Drogon
23:10
Cum Swallower Club - By Drogon
21:24
Acting Like A Slut - Caption Story
37:46
Sissy Getaway
13:36
Sissy Island - Sissy Caption Story Porn
08:29
Bachelor Party - Sissy Caption Story Porn
09:53
Loser Case Study - Rough Stuff
32:04
Forced Sissy Caption Story PMV
09:40
Stupid Drunk Dares - Sissy Caption Story Porn
09:06
Boss's Son - Sissy Caption Story Porn
30:11
BNWO Goon File
26:30
Grindr Whore
29:39
Sissy Is forced To Visit - Caption Story PMV
17:46
Alpha-Owned - By Drogon
02:41
BBC Wetdrops PMV - Piss
09:36
Sissy Story Fuckdoll
03:56
Covered In Piss ~by Cthl55
34:17
Sissy Life By Drogon
24:06
Cum Swallower Club 2
13:07
Stupid Goon Meat
21:40
My Ex Tricked Me Into Becoming A Girl - And I Liked It - Pt 1 - X-Change Story
22:19
Dirty Old Daddies By Drogon
01:03
Sissy Caption Story - After Club Party
01:58
Sissy Caption Story - The Sissy's Daddy
58:57
The Frat Slut - Sissy Caption Story
25:01
Sissy Forced To Gangbang - Caption Story PMV
06:11
Bullied By BBC - Poppers And Throat Trainer
14:06
Real Men Real Cocks - By Drogon
17:04
Cum Eating Mindfuck - By Drogon
23:23
Pimped Out 2 - By Drogon
40:50
Bullied Sissy Goes To The Gym - Caption Story PMV
16:25
Give Men Your Throat - By Drogon
12:35
Piss Whore 1
50:48
The Bully Kink
01:15
Your Bully Came To Beat Your Ass
06:53
A Gang Makes Policewoman Their Bitch
00:51
Horny Sissy Boy For Money
1:16:31
Piss Whore 2
1:14:06
Piss Whore 3
03:32
Muevete Perrita
07:44
Sissy Dreams - Hitchhiker
24:41
Sissy Dreams - Hitchhiker Part 2
1:01:10
Piss Whore 4 - Affirmations And Mantras
02:20
Black Master Meet My Family - Babecock Hypno
45:15
Sissy Dreams - Career Girl - YVN90
02:00
Your Mother Became A Cum Whore
03:17
Ur Mom Was Spotted On Chaturbate
07:42
Found Footage - Sissy Story
19:35
ATM Man By Drogon - Full Version
02:00
TikTok Sissies 1
09:31
Doomed To Goon Part 2
05:10
My Mommy Became A BBC Slut
02:18
Modern Pussy PMV
18:48
Suffer For Their Pleasure By Drogon
11:09
Truth Or Dare - The Night You Became Their Sissy - Part 1
02:02
Cosplay Convention - BBC World
05:10
Your Master Awaits
05:02
Shemale Top
16:50
Your Bully - Captions Story
01:00
Rental Agreement - Sissy Shorts
01:20
Friends With Benefits - Teaser
03:00
From Denial To Addiction
03:57
Masculinity Dies Here
05:31
Pillow Chupon PMV
17:20
Frat - Sissy Caption Story
02:29
Cum Swallower Club Encore - Teaser
02:00
Santurrona PMV
00:46
Bully Made You His Slut - Sissy Caption Story
01:58
Culiadora
00:28
Lost Bet - Caption Story
01:00
From Bro To Bitch
01:00
Sissy Caption - Your Big Dick Friend Bet You To Dress As A Girl
03:51
Ningen Toire - Poppers Edition
01:36
Now Is Over
01:00
House Slut Training
03:29
Suculenta Carol PMV
00:39
Sissy Shower Story
15:08
Cosplay For An Old Friend
10:47
Nasty Piss Slut
03:01
They Know
02:14
UUi PMV
15:46
A Slutty Sissy Jenny - Confessional No2 - The Warehouse
00:24
Swallow Your Pride Pig
26:08
Bullied Sissy Tries Sports - Caption Story PMV
03:18
Anal Overload
03:23
MmM PMV
07:52
Gentle
11:08
Doctors Orders
03:03
PMV Loquito
01:54
Fuel
02:48
You Are These Captions Sissy
01:00
Sexy Sissy Bitch
05:31
Sissy Piss Princess 2 - Piss Whore Anthem
02:51
Winners And Losers - Teaser By Drogon
03:11
Yo Perreo Sola PMV
02:25
Lost Bet Friends Night - Sissy Caption Story
01:48
Goon Your Brain
07:25
Fuckdoll Fate
05:11
Pimped Out For Men To Use
08:38
Please Men Wherever They Want
04:26
Tik Tok Black Cock - PMV
03:43
Perreo Del Porki PMV
09:58
From Friends To Being Owned
07:23
Grindr Dom Daddy
02:02
Titis PMV
07:56
Roommate Won The Bet
07:35
Blackmailed By Your Colleague
02:31
Dumb - PMV Inferiority
07:43
Grindr Date Wont Leave
05:40
First Night On The Job Gangbang Captions
16:20
Help Your Friend Out - Full Version
03:47
Fuck Me Daddy
01:00
Sissy Of The Friendgroup
03:15
Thot Shit - A Shemale PMV
07:35
Mens Plaything
Roommate Won The Bet
93%
(89)
About
Add to playlist
Submitted by
NoelleCaptions
07:56
69284
2026-06-08 15:01:47
A story of how you lost the bet and became your roommates sextoy!
Tags:
sissy
,
captions
,
roommate
,
caption story
,
cock
,
cock sucking
,
deepthroat
,
bet
,
crossdressing
,
pov
,
fucking
,
anal
,
trans
,
tgirl
,
shemale
Categories:
Anal
,
Big Cock
,
Caption Story
,
Captions
,
Cock Sucking
,
Fucking
,
Movies
,
Tgirls
Show more
Show less
<iframe src='https://hypnotube2.com/embed/133175' frameborder='0' height='400' width='600'></iframe><br><strong>Roommate Won The Bet</strong> - powered by <a href='https://hypnotube2.com'>Hypnotube Beta</a>
Comments
(2)
Show more
Show less
You must be logged in to post wall comments. Please
Login
or
Signup (free)
.
Related Content
05:09
Moms Ex Roommate - A Caption Story
86%
52024
00:45
HD
You Lost The Bet - Part 1 - Sissy Caption Story
81%
50963
15:39
HD
Hypnosister - The Bet - Deutsche Sprache KI - German Language AI
83%
72782
00:28
HD
Lost Bet - Caption Story
86%
44190
04:05
Lost Basketball Bet
90%
79443
01:19
HD
Roommate Surprise - Sissy Caption Story
86%
64490
04:29
HD
How To Seduce Your Roommate - A Caption Story
91%
113515
03:23
HD
Losing The Bet
88%
76309
03:37
HD
Losing The Bet
89%
35677
15:04
HD
The Roommate Setup - A Sissy Caption Story
85%
129519
05:34
HD
Passing For A Friend - A Sissy Caption Story
89%
56750
04:03
HD
A New Workout Routine - Shemale Caption Story
88%
35001
00:34
HD
New Roommate
90%
111709
01:00
HD
Roommate Found Out
90%
30929
01:41
HD
Losing The Bet
92%
58666
01:10
HD
The Cosplay Whore - A Sissy Caption Story
88%
36709
10:16
HD
Roommate - Sissy Caption Story
93%
179086
01:00
HD
Won 1V1 In A Video Game - Captio Story
80%
18908
15:39
HD
Hypnosister - The Bet
92%
347827
01:00
HD
This Was Your Best Prank You Pulled On Your Roommate
94%
106633
09:24
HD
Maid Service - A Sissy Caption Story
85%
77532
04:13
HD
Losing The Bet Again
71%
50712
11:31
HD
Acting Practice - Sissy Caption Story Porn
83%
1352808
00:41
HD
Easy Win - Sissy Caption Story
92%
59737
You must be logged in to post wall comments. Please Login or Signup (free).