Sissy Humiliation Videos (3,738)

The Sissy Casting Couch

HD 0:10 / 14:43

The Sissy Casting Couch

LoyalFans 6 hours ago

Sissy training task September 25

Sissy training task September 25

Clips4sale 1 year ago

Whittle Old BB Dick Just Needs MeanMommy’s Love

Whittle Old BB Dick Just Needs MeanMommy’s Love

Clips4sale 1 year ago

Young Mistress Femdom 217

HD 0:30 / 59:13

Young Mistress Femdom 217

Clips4sale 1 year ago

You Wish

Clips4sale 1 year ago

Glamour Girls Cuckolding 228 FULL-MOVIE wmv

63% 4K 0:30 / 1:09:52

Glamour Girls Cuckolding 228 FULL-MOVIE wmv

Clips4sale 1 year ago

Camp Bimbo

Clips4sale 4 months ago

Sissy Squat Endurance Training in Tight Red Rope & Locked Chastity

4K 0:29 / 47:17

Sissy Squat Endurance Training in Tight Red Rope & Locked Chastity

Clips4sale 3 months ago

SISSY MANNEQUIN TASK

SISSY MANNEQUIN TASK

Clips4sale 9 months ago

Feminized cuck shock collar

Feminized cuck shock collar

Clips4sale 7 months ago

Pathetic New Hire Sissified by Barbaric Boss! - Full Version

HD 0:30 / 25:47

Pathetic New Hire Sissified by Barbaric Boss! - Full Version

Clips4sale 11 months ago

Sissy Slave's Nylons, Piss, and Cum: A Humiliating Solo Session

Sissy Slave's Nylons, Piss, and Cum: A Humiliating Solo Session

Clips4sale 1 year ago

Sissy Poker Night audio

HD 0:25 / 10:01

Sissy Poker Night audio

Clips4sale 4 months ago

Sissy Feminization Training by Two Spanish Mistresses

HD 0:16 / 12:21

Sissy Feminization Training by Two Spanish Mistresses

Clips4sale 4 months ago

Anal Teasing with Black Gloves for Sissy MOV

HD 0:13 / 12:56

Anal Teasing with Black Gloves for Sissy MOV

Clips4sale 5 months ago

SISSY HUSBANDS 2: COCK SUCKING

SISSY HUSBANDS 2: COCK SUCKING

Clips4sale 10 months ago

Sissy Assfucks You and Diapers Too

Sissy Assfucks You and Diapers Too

Clips4sale 10 months ago

DRESSED UP AND EXPOSED AT THE MALL

Premium HD 9:30

DRESSED UP AND EXPOSED AT THE MALL

C4S 3 weeks ago

Diaper Satin Sissy Halloween Humiliation

66% HD 0:30 / 15:51

Diaper Satin Sissy Halloween Humiliation

Clips4sale 1 year ago

Feminizing and Pissing on a Sissy Slut

HD 0:30 / 14:57

Feminizing and Pissing on a Sissy Slut

Clips4sale 5 months ago

HOT Blonde Crossdresser in Pink Chastity Fucked

HOT Blonde Crossdresser in Pink Chastity Fucked

Clips4sale 5 months ago

Leather sissy Katja as my human ashtray

57% 0:11 / 8:59

Leather sissy Katja as my human ashtray

Clips4sale 4 years ago

NOT GAY IF YOURE A GIRL

66% 0:11 / 9:41

NOT GAY IF YOURE A GIRL

Clips4sale 4 years ago

12 DAYS OF GAY-MAS! DAY 7

12 DAYS OF GAY-MAS! DAY 7

Clips4sale 3 years ago

12 DAYS OF GAY-MAS! DAY 10

4K 0:25 / 13:01

12 DAYS OF GAY-MAS! DAY 10

Clips4sale 3 years ago

The Interview Part 1

The Interview Part 1

Clips4sale 3 years ago

(4K) Sissy Gamer Gurl: Femdom Huge Dildo Anal Pegging Part 2 of 3

66% 4K 0:30 / 13:51

(4K) Sissy Gamer Gurl: Femdom Huge Dildo Anal Pegging Part 2 of 3

Clips4sale 3 years ago

Dress Up Sissy Doll

Dress Up Sissy Doll

Clips4sale 3 years ago

Sissy School Vlog Slumber Party

65% HD 0:30 / 10:38

Sissy School Vlog Slumber Party

Clips4sale 2 years ago

Sissy Ex Girlfriends Party

Sissy Ex Girlfriends Party

Clips4sale 2 years ago

How To Stroke For My Profit

How To Stroke For My Profit

Clips4sale 2 years ago

Stroke While Squealing

Stroke While Squealing

Clips4sale 2 years ago

POV 3some Crossdresser Sub Camila POV blowjob 69 while Dadddy got fucked P4

HD 0:21 / 10:09

POV 3some Crossdresser Sub Camila POV blowjob 69 while Dadddy got fucked P4

Clips4sale 2 years ago

Make Me Bi For The Cuckold Cunt (Quicktime)

Make Me Bi For The Cuckold Cunt (Quicktime)

Clips4sale 4 years ago

FAT SHAMING MY STEP-BROTHER

FAT SHAMING MY STEP-BROTHER

Clips4sale 4 years ago

Lacy Lottery Life (1080 HD)

Lacy Lottery Life (1080 HD)

Clips4sale 4 years ago

Gay boyfriend bimbofication

Gay boyfriend bimbofication

Clips4sale 3 years ago

Sissy Stroke Along

Sissy Stroke Along

Clips4sale 3 years ago

Your Tiny Dick Won't Work, Guess you Should be my Girlfriend

Your Tiny Dick Won't Work, Guess you Should be my Girlfriend

Clips4sale 4 years ago

Pleasure withdrawal addiction symptoms of crossdresser (540P)

48% 0:11 / 50:29

Pleasure withdrawal addiction symptoms of crossdresser (540P)

Clips4sale 4 years ago

ForXed bi first experience PT2 - being our slut 480p

67% 0:20 / 9:07

ForXed bi first experience PT2 - being our slut 480p

Clips4sale 4 years ago

Finish Quick, Sissy

HD 0:11 / 10:06

Finish Quick, Sissy

Clips4sale 4 years ago

BAD SISSY BOY (mp4) FULLVERSION

BAD SISSY BOY (mp4) FULLVERSION

Clips4sale 4 years ago

Sissy Task Of The Day #4

Sissy Task Of The Day #4

Clips4sale 4 years ago

from cheater to sissy: punishment pegging from futa step-mommy - SD

from cheater to sissy: punishment pegging from futa step-mommy - SD

Clips4sale 3 years ago

12 DAYS OF GAY-MAS! DAY 2

4K 0:25 / 10:21

12 DAYS OF GAY-MAS! DAY 2

Clips4sale 3 years ago

You're the Queen's Fuck Doll (1080)

61% HD 0:18 / 9:19

You're the Queen's Fuck Doll (1080)

Clips4sale 3 years ago

Fucked In Every Room: Barbie's Wet Dream House Part 3 (4K)

4K 0:48 / 15:11

Fucked In Every Room: Barbie's Wet Dream House Part 3 (4K)

Clips4sale 4 years ago

ONCE YOU BAREBACK ALWAYS BAREBACK PURE FUCKING cumshot FETISH CLOTING 5

ONCE YOU BAREBACK ALWAYS BAREBACK PURE FUCKING cumshot FETISH CLOTING 5

Clips4sale 2 years ago

Sissy Reprogramming Meditation - Audio Only MP3

HD 0:22 / 10:53

Sissy Reprogramming Meditation - Audio Only MP3

Clips4sale 2 years ago

SISSY EXPOSURE CODE

SISSY EXPOSURE CODE

Clips4sale 2 years ago

Alpha couple Nara and Hex welcome their new TS Maid - Part 1 (1080 EN-sub)

HD 0:30 / 16:07

Alpha couple Nara and Hex welcome their new TS Maid - Part 1 (1080 EN-sub)

Clips4sale 2 years ago

Your First Time Sissy Session

Your First Time Sissy Session

Clips4sale 2 years ago

Love Sick Simp

HD 0:29 / 10:39

Clips4sale 2 years ago

P4 HALLOWEEN BLACK AND ORANGE CATSUIT TWINK LATEX FEMMEBOI TEASING KISSING DEEPTHROAT TAKING CONDOM OFF SHEMALE

63% HD 0:20 / 10:12

P4 HALLOWEEN BLACK AND ORANGE CATSUIT TWINK LATEX FEMMEBOI TEASING KISSING DEEPTHROAT TAKING CONDOM OFF SHEMALE

Clips4sale 1 year ago

Your Mistresses Toys

Your Mistresses Toys

Clips4sale 3 years ago

Good Sissies Always Swallow

Good Sissies Always Swallow

Clips4sale 3 years ago

Faggot Gangbang

45% 0:11 / 12:45

Faggot Gangbang

Clips4sale 3 years ago

Introduction to Sissy Academy (MOV)

63% 0:09 / 5:18

Introduction to Sissy Academy (MOV)

Clips4sale 3 years ago

Nylon Femdom 217

61% 0:11 / 59:09

Nylon Femdom 217

Clips4sale 3 years ago

Making Yard Man into a Sissy Slave Part 1

Making Yard Man into a Sissy Slave Part 1

Clips4sale 3 years ago

SISSYBB IS A CERTIFIED HOMOSEXUAL: EXPOSURE-FANTASY

SISSYBB IS A CERTIFIED HOMOSEXUAL: EXPOSURE-FANTASY

LoyalFans 3 years ago

Sissy Games : When my Cuckold Husband Meets my Lovers - Maitresse Julia

HD 0:10 / 28:04

Sissy Games : When my Cuckold Husband Meets my Lovers - Maitresse Julia

LoyalFans 3 years ago

Cruel Sissification

HD 0:10 / 13:18

Cruel Sissification

LoyalFans 3 years ago

Entertain me Cock-whore

Entertain me Cock-whore

Clips4sale 3 years ago

Sissy Reality Show!

Sissy Reality Show!

Clips4sale 2 years ago

Pink Dreams - Face Only (1080 HD)

HD 0:11 / 22:03

Pink Dreams - Face Only (1080 HD)

Clips4sale 4 years ago

My Sissy Drone

HD 0:30 / 15:18

Clips4sale 4 years ago

CV Big ass on jeans humiliation

CV Big ass on jeans humiliation

Clips4sale 3 years ago

Your First Anal Dildo Sissy Task

Your First Anal Dildo Sissy Task

Clips4sale 3 years ago

Be My Sissy Slave

65% HD 0:23 / 11:27

Be My Sissy Slave

Clips4sale 3 years ago

Encouraging Bisex Pt1 Fucking machine preparing you for my Bull - Real Time Session Recording

Encouraging Bisex Pt1 Fucking machine preparing you for my Bull - Real Time Session Recording

Clips4sale 3 years ago

Encouraging Bisex PT3 - Bull’s happy end… - Real Time Session Recording - 480p

65% 0:15 / 5:02

Encouraging Bisex PT3 - Bull’s happy end… - Real Time Session Recording - 480p

Clips4sale 3 years ago

Slut training blow job Encouraging PT1 - Real time session recording

Slut training blow job Encouraging PT1 - Real time session recording

Clips4sale 3 years ago

MY CROSSDRESSER SISSY SLUT

4K 0:25 / 13:58

MY CROSSDRESSER SISSY SLUT

Clips4sale 3 years ago

Giantess Sissy Slut Humiliation! wmv

Giantess Sissy Slut Humiliation! wmv

Clips4sale 3 years ago

Crossdressing Pervert Finally Does Anal (Part 3)

62% 0:28 / 13:07

Crossdressing Pervert Finally Does Anal (Part 3)

Clips4sale 3 years ago

Sissy Wife Licks Bull's Creampie Out Of My Panties

Sissy Wife Licks Bull's Creampie Out Of My Panties

Clips4sale 3 years ago

Rumor has it…

Rumor has it…

Clips4sale 3 years ago

P2 SLOW MOTION FUCKING LIVING DOLL RESTRAINED IN PVC LATEX OUTFIT and FISHNETS HARD CORE

HD 0:20 / 10:11

P2 SLOW MOTION FUCKING LIVING DOLL RESTRAINED IN PVC LATEX OUTFIT and FISHNETS HARD CORE

Clips4sale 2 years ago

Fucking the butler

63% HD 0:10 / 11:42

Fucking the butler

LoyalFans 3 years ago

SISSYBB EXPOSED

SISSYBB EXPOSED

LoyalFans 3 years ago

YOU’RE NOT GAY - YOU JUST LOVE DICK

YOU’RE NOT GAY - YOU JUST LOVE DICK

LoyalFans 3 years ago

Inara à Doutrinadora - Eating the Male's Ass While the Wife Stands at My Friend's Feet

57% 0:29 / 21:03

Inara à Doutrinadora - Eating the Male's Ass While the Wife Stands at My Friend's Feet

Clips4sale 3 years ago

Sissy Maid Dress Up Training: Sissy Training with Ivy Chaos

Sissy Maid Dress Up Training: Sissy Training with Ivy Chaos

Clips4sale 1 year ago

Truth be told (custom)

62% 0:15 / 10:17

Truth be told (custom)

Clips4sale 1 year ago

Uninvited Slumber Party Guest The Complete Collection 1-7 Written by Kylie Gable and Narrated by Shayla Aspasia

HD 0:30 / 4:00:00+

Uninvited Slumber Party Guest The Complete Collection 1-7 Written by Kylie Gable and Narrated by Shayla Aspasia

Clips4sale 1 year ago

TEASING SISSYFICATION SLOW MOTION

55% 0:11 / 3:25

TEASING SISSYFICATION SLOW MOTION

Clips4sale 1 year ago

Lips in Saliva, Filthy, Verbal Sissy Spitting, Self Facial

47% HD 0:30 / 22:18

Lips in Saliva, Filthy, Verbal Sissy Spitting, Self Facial

Clips4sale 1 year ago

Sissy BrainFuck Compilation FULL MOVIE

63% HD 0:30 / 1:13:15

Sissy BrainFuck Compilation FULL MOVIE

Clips4sale 1 year ago

Empty Sissy Head

HD 0:27 / 11:07

Empty Sissy Head

Clips4sale 1 year ago

Young Mistress Houseslave 51

Young Mistress Houseslave 51

Clips4sale 1 year ago

Sissification training lesson 1 - Mobile

Sissification training lesson 1 - Mobile

Clips4sale 1 year ago

Orientation for Step-Daddy’s New Prisoner

51% HD 0:30 / 13:55

Orientation for Step-Daddy’s New Prisoner

Clips4sale 1 year ago

Young Mistress Humiliation 249 wmv

Young Mistress Humiliation 249 wmv

Clips4sale 1 year ago

Transform Yourself With Me

HD 0:27 / 10:36

Transform Yourself With Me

Clips4sale 2 years ago

Jenna Reid's Sissy Cuckold Gets Spanked With A Wooden Paddle

Jenna Reid's Sissy Cuckold Gets Spanked With A Wooden Paddle

Clips4sale 2 years ago

Beta to Sissy Custom Clip

63% 0:09 / 10:00

Beta to Sissy Custom Clip

Clips4sale 2 years ago

Sissy Slut gets a Lesson in Pleasing Men Part 1 of 2 (1080p)

HD 0:11 / 12:52

Sissy Slut gets a Lesson in Pleasing Men Part 1 of 2 (1080p)

Clips4sale 2 years ago

Alpha couple Nara and Hex welcome their new TS Maid - Complete (720 EN-sub)

HD 0:32 / 32:13

Alpha couple Nara and Hex welcome their new TS Maid - Complete (720 EN-sub)

Clips4sale 2 years ago

pov sph BG hot huge cock futa pegs sissy in chastity - wmv

pov sph BG hot huge cock futa pegs sissy in chastity - wmv

Clips4sale 2 years ago

Evil Lohan: Smokin' with Sissy

Evil Lohan: Smokin' with Sissy

Clips4sale 2 years ago

The Male Urge 2_

63% 1:00 / 5:38

The Male Urge 2_

Clips4sale 2 years ago

1FETISH CLOTHING DEEPTHROAT BAREBACK SUB SATIM LATINA DOMME IN THIGH HIGH LEATHER BOOTS

1FETISH CLOTHING DEEPTHROAT BAREBACK SUB SATIM LATINA DOMME IN THIGH HIGH LEATHER BOOTS

Clips4sale 2 years ago

Man Catcher - the punishment collar *MOV*

61% HD 0:22 / 11:30

Man Catcher - the punishment collar *MOV*

Clips4sale 2 years ago

Pantyhose Cock Sucker || AUDIO MP4 || FEMINIZATION || BEST SELLER

Pantyhose Cock Sucker || AUDIO MP4 || FEMINIZATION || BEST SELLER

Clips4sale 2 years ago

I Support Your Cross Dressing

I Support Your Cross Dressing

Clips4sale 2 years ago

Glamour Girls Humiliaion 249

Glamour Girls Humiliaion 249

Clips4sale 2 years ago

Closet Sissy JOI Countdown

Closet Sissy JOI Countdown

Clips4sale 2 years ago

Prepare for Your Bimbo Slut Transformation

Prepare for Your Bimbo Slut Transformation

Clips4sale 2 years ago

Mrs Nara Sissification Training - Complete: A one-way trip from Boy to Slut (1080 EN-sub)

HD 0:47 / 50:04

Mrs Nara Sissification Training - Complete: A one-way trip from Boy to Slut (1080 EN-sub)

Clips4sale 2 years ago

Your Gayboi Secrets Are Getting So Big! Fetish Erotic Audio Crossdressing Humiliation Exposure-fantasy

Your Gayboi Secrets Are Getting So Big! Fetish Erotic Audio Crossdressing Humiliation Exposure-fantasy

Clips4sale 2 years ago

Pussification Of Man

Pussification Of Man

Clips4sale 2 years ago

S1 EP3 BONDAGE FULL DRESSED UP VELVET BLACK GLOVES CROSSDRESSER DEEPTHROAT BONDAGE BY FETISHTRANSEXUAL

HD 0:21 / 10:16

S1 EP3 BONDAGE FULL DRESSED UP VELVET BLACK GLOVES CROSSDRESSER DEEPTHROAT BONDAGE BY FETISHTRANSEXUAL

Clips4sale 2 years ago

Coaxing a Sissy to Crossdress and Jerk Off

4K 0:29 / 16:45

Coaxing a Sissy to Crossdress and Jerk Off

Clips4sale 2 years ago

Lets see if you can pleasure my crossdresser friend - Miss Honour May - MP4 SD

Premium HD 11:00

Lets see if you can pleasure my crossdresser friend - Miss Honour May - MP4 SD

Clips4sale 4 years ago

Delightful magic wand tor*ure for my Christmas sissy (no cum)

46% HD 0:11 / 1:22:09

Delightful magic wand tor*ure for my Christmas sissy (no cum)

Clips4sale 4 years ago

Mini Me Social Media Challenge

Mini Me Social Media Challenge

Clips4sale 4 years ago

Cum on your face, sissy slut!

HD 0:20 / 10:55

Cum on your face, sissy slut!

Clips4sale 4 years ago

The Submissive Assistant : A Slutty New Uniform

HD 0:15 / 15:30

The Submissive Assistant : A Slutty New Uniform

Clips4sale 4 years ago

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