Sissy Training - Porn Videos (147,083)

”Bi-Curious Bro Gets A Sissy Sandwich”

”Bi-Curious Bro Gets A Sissy Sandwich”

TransHero 6 months ago

Cum Eating instruction CEI #1 By Bestsissycaptions

Cum Eating instruction CEI #1 By Bestsissycaptions

FreePorn8 1 year ago

Gentle Bi Encouragement - Will You Suck Cock For Me?

Gentle Bi Encouragement - Will You Suck Cock For Me?

XHamster 1 year ago

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

57% 1:01 / 20:13

Step Mother Step Son Roleplay Hucow Video Custom for Superfan Beardypirate

FapHouse 1 year ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 4 years ago

Akira Sissifies Jessica (HD WMV)

50% HD 0:26 / 13:00

Akira Sissifies Jessica (HD WMV)

Clips4sale 10 months ago

Sensual pegging turns in hard painal that breaks his pussy open. Listen my bitch whine taking dick

Sensual pegging turns in hard painal that breaks his pussy open. Listen my bitch whine taking dick

Pornfact 3 months ago

Wife Fucks Husband Like a Submissive Sissy Pegging Rimming #68 Part 1

Wife Fucks Husband Like a Submissive Sissy Pegging Rimming #68 Part 1

XHamster 2 years ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

XHamster 2 years ago

Suck Cock and Swallow Hot Cum - Obey Your Mistress

Suck Cock and Swallow Hot Cum - Obey Your Mistress

XHamster 1 year ago

Cum Eating instruction CEI #1 By Bestsissycaptions

Cum Eating instruction CEI #1 By Bestsissycaptions

Amateur8 2 years ago

Good boys eat cum

Good boys eat cum

XHamster 1 year ago

Aurora Ber Private Show

50% 4K 2:00 / 6:07

Aurora Ber Private Show

Flirt4Free 10 months ago

Pissing CFNM domina punishes sissy in BDSM lesson

Pissing CFNM domina punishes sissy in BDSM lesson

Some.Porn 1 year ago

SISSY CUM EATING

SISSY CUM EATING

Amateur8 4 years ago

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

Asian MILF Mistress Inserts Huge Dildo Into Slave Ass

XHamster 5 months ago

Sissy anal whore gets deep throated, hardcore pegging, rough ass fucked, and anal fisting

Sissy anal whore gets deep throated, hardcore pegging, rough ass fucked, and anal fisting

Pornfact 3 days ago

Stuffing The Sissy

65% HD 0:10 / 11:25

Stuffing The Sissy

LoyalFans 1 year ago

Anna Blake makes a sissy milf out of you femdom obedience training

Anna Blake makes a sissy milf out of you femdom obedience training

AveXXX 1 week ago

Viky & Mateo Private Show

57% HD 2:00 / 32:44

Viky & Mateo Private Show

Flirt4Free 6 months ago

Sexy Wife with Big Strapon pegging her Husband with Handjob

Sexy Wife with Big Strapon pegging her Husband with Handjob

XHamster 1 year ago

Brittney & Elvis Private Show

56% HD 2:00 / 6:22

Brittney & Elvis Private Show

Flirt4Free 2 years ago

Emily & Stesha Private Show

58% 4K 2:00 / 8:48

Emily & Stesha Private Show

Flirt4Free 6 months ago

Jhanne Cherry Private Show

51% 4K 2:00 / 23:18

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Bi Humiliation & Cum Clean up with a Female Audience

48% 1:01 / 8:42

Bi Humiliation & Cum Clean up with a Female Audience

FapHouse 1 year ago

Emily & Stesha Private Show

75% 4K 2:00 / 8:54

Emily & Stesha Private Show

Flirt4Free 3 months ago

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

XHamster 11 months ago

Therapy for sissy boys and cum eating goddess

Therapy for sissy boys and cum eating goddess

AveXXX 1 week ago

Big-dicked sissy takes it up the ass and swallows his own cum

Big-dicked sissy takes it up the ass and swallows his own cum

XXXShake 3 years ago

Bi Encouragement Training - Take 2 Of My Mans Cumshots

Bi Encouragement Training - Take 2 Of My Mans Cumshots

XHamster 4 days ago

Cuckold 2 (lick My Toilet Clean!)

60% HD 0:39 / 5:36

Cuckold 2 (lick My Toilet Clean!)

FapHouse 1 year ago

Huge Strap-On Fucks My Sissy Hole While I’m Locked and Pretty

Huge Strap-On Fucks My Sissy Hole While I’m Locked and Pretty

Pornfact 3 months ago

My Wife Turned Me Into a Sissy Cock Sucking & FUCKING Whore! I Get Pegged, FISTED & Trained for BBC

My Wife Turned Me Into a Sissy Cock Sucking & FUCKING Whore! I Get Pegged, FISTED & Trained for BBC

Pornzona 3 months ago

Shaving and balls busting part 2

Shaving and balls busting part 2

XHamster 11 months ago

Sissy training and feminisation: A Feminine makeover for Miss Dayana’s chattel

57% HD 0:24 / 8:50

Sissy training and feminisation: A Feminine makeover for Miss Dayana’s chattel

Clips4sale 3 weeks ago

feminized - femdom sissy training sex doll milked with fucking machine porn video

feminized - femdom sissy training sex doll milked with fucking machine porn video

BDSMShip 2 years ago

Amy Perspective - Big cock cumming a lot - FPOV trailer

Amy Perspective - Big cock cumming a lot - FPOV trailer

Pornfact 1 week ago

Sissy Compilation Chastity Forever

Sissy Compilation Chastity Forever

Lesbian8 1 month ago

Training you to be a woman - Femdom Feminization Encouragement

Training you to be a woman - Femdom Feminization Encouragement

Pornfact 3 days ago

Ares & Adara Private Show

55% HD 2:00 / 9:20

Ares & Adara Private Show

Flirt4Free 1 year ago

Jhanne Cherry Private Show

55% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 10 months ago

Long and Hard Pegging with a big dildo – Topped Toys Mordax 90

Long and Hard Pegging with a big dildo – Topped Toys Mordax 90

XHamster 4 years ago

Viky & Mateo Private Show

58% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 6 months ago

Sissy Inspection & Fucking

Sissy Inspection & Fucking

Pornfact 1 week ago

Pegging and fisting my husband's asshole

Pegging and fisting my husband's asshole

XHamster 2 years ago

SISSIFYME. A SISSY FOR LIFE

SISSIFYME. A SISSY FOR LIFE

BigTitsLust 1 year ago

cum and fun - Part 3

cum and fun - Part 3

Camster 3 days ago

Enforced Feminization - Femdom Sissy Training - Goddess Maven

Enforced Feminization - Femdom Sissy Training - Goddess Maven

Pornfact 1 week ago

Goddess Of Destruction Pregnant Sissy Mind Training

Goddess Of Destruction Pregnant Sissy Mind Training

WinPorn 1 month ago

Hardcore Up Close Femdom Bi Encouragement Oral job and CEI

Hardcore Up Close Femdom Bi Encouragement Oral job and CEI

Dafreeporn 3 years ago

Slave training in heat

Slave training in heat

XHamster 11 months ago

Sissy's Daily Service - Brianna Beach - Faphouse Preview

Sissy's Daily Service - Brianna Beach - Faphouse Preview

XHamster 3 years ago

Suck His Dick Loser

Suck His Dick Loser

XHamster 1 year ago

Heartless big beautiful woman Dominatrix Destroys Stepson CBT Boots, Unfathomable Gagging, Anal Stretching, Sissification and Void urine Drinking!

Heartless big beautiful woman Dominatrix Destroys Stepson CBT Boots, Unfathomable Gagging, Anal Stretching, Sissification and Void urine Drinking!

BigTitsLust 2 weeks ago

Jennas Suprise

XHamster 2 years ago

Mean femdom Flagellation Treatment

Mean femdom Flagellation Treatment

Some.Porn 1 year ago

Becoming a sissy

Becoming a sissy

Dafreeporn 6 years ago

Evil big beautiful woman Domina Destroys Stepson CBT Boots, Unfathomable Gagging, Anal Stretching, Sissification and Void urine Drinking!

Evil big beautiful woman Domina Destroys Stepson CBT Boots, Unfathomable Gagging, Anal Stretching, Sissification and Void urine Drinking!

SortPorn 1 week ago

sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

XHamster 2 years ago

Sissy Princess Training

Sissy Princess Training

FreePorn8 4 days ago

Lady Caitlyn Party on Jun 30, 2026

65% HD 2:00 / 1:00:18

Lady Caitlyn Party on Jun 30, 2026

Flirt4Free 1 week ago

Positive Femdom: Pegging, Fisting to Each Other, Pee. Arya Grander

Positive Femdom: Pegging, Fisting to Each Other, Pee. Arya Grander

XHamster 1 year ago

Viky & Mateo Private Show

62% HD 2:00 / 19:22

Viky & Mateo Private Show

Flirt4Free 6 months ago

Jhanne Cherry Private Show

54% HD 2:00 / 40:31

Jhanne Cherry Private Show

Flirt4Free 9 months ago

The Final Transformation Part 2

The Final Transformation Part 2

Dafreeporn 3 months ago

Suck Wang For Your Mastix - Bi Encouragement

Suck Wang For Your Mastix - Bi Encouragement

Amateur8 1 year ago

Sweet & Daaniel Private Show

65% HD 2:00 / 14:05

Sweet & Daaniel Private Show

Camster 3 weeks ago

My Cuckold Slave Cleanup Cum From My Pussy and Beverage My Piss and Licks My Pussy Clean

My Cuckold Slave Cleanup Cum From My Pussy and Beverage My Piss and Licks My Pussy Clean

XHamster 2 years ago

You Will Beg Me To Link You To This Video. Big Compilation.

You Will Beg Me To Link You To This Video. Big Compilation.

XHamster 3 years ago

Khloe Clark Private Show

50% 4K 2:00 / 24:07

Khloe Clark Private Show

Camster 3 weeks ago

... - Part 3

55% 4K 2:00 / 4:53

Camster 2 weeks ago

Femdom Anal Training and Feminization

Femdom Anal Training and Feminization

Lesbian8 1 week ago

JOI Echo in Latex with My Big Black Strapon - Luna Doll

JOI Echo in Latex with My Big Black Strapon - Luna Doll

XHamster 8 months ago

Sissygasm Training: My Cockhungry Femboi Learns to Serve and Suffer

Sissygasm Training: My Cockhungry Femboi Learns to Serve and Suffer

Pornfact 3 months ago

alexis amadahy and jade sissy training and strap on

alexis amadahy and jade sissy training and strap on

PornOne 8 years ago

Sissy Sex Positions Training

HD 0:10 / 15:30

Sissy Sex Positions Training

LoyalFans 2 years ago

Anal training JOI, edging and denial

Anal training JOI, edging and denial

Pornzona 4 months ago

Male to Feminized Sissy Bondage Transformation

59% 0:12 / 12:32

Male to Feminized Sissy Bondage Transformation

Clips4sale 1 year ago

Viky & Mateo Private Show

55% HD 2:00 / 32:44

Viky & Mateo Private Show

Camster 6 months ago

Emmalee Jones Pov Hand Job Joi

Emmalee Jones Pov Hand Job Joi

Flirt4Free 11 months ago

Training You, My Sissy, to Love Cock

59% HD 0:10 / 10:14

Training You, My Sissy, to Love Cock

LoyalFans 2 weeks ago

I'm a dirty slave of my wife... she can do everything with me

I'm a dirty slave of my wife... she can do everything with me

XHamster 7 months ago

Eye-Contact Pegging JOI Sissification POV - I Make My Sissy Princess Cum Like a Good Girl

Eye-Contact Pegging JOI Sissification POV - I Make My Sissy Princess Cum Like a Good Girl

XHamster 1 year ago

JOI Echo in Latex with My Big Black Strapon - Luna Doll

57% 0:39 / 25:09

JOI Echo in Latex with My Big Black Strapon - Luna Doll

FapHouse 8 months ago

MAID TO SERVE #1

63% 4K 0:28 / 14:01

MAID TO SERVE #1

Clips4sale 2 years ago

INSTITUTION X - Prostate Milking Anal Training Pspot Orgasm COMPILATION 1-2

INSTITUTION X - Prostate Milking Anal Training Pspot Orgasm COMPILATION 1-2

Pornfact 2 weeks ago

Hard Lesson for Slut Sadie

70% 0:59 / 30:58

Hard Lesson for Slut Sadie

Clips4sale 4 years ago

BBC Sissy FPOV Blow Job Mindwash - Femdom - Female-Taskmaster Alexa and Father Jay

BBC Sissy FPOV Blow Job Mindwash - Femdom - Female-Taskmaster Alexa and Father Jay

Dafreeporn 4 years ago

wife bbc

MyLust 3 years ago

$let\'s have some fun - Part 2$ 4K 2:00 / 4:53

let\'s have some fun - Part 2

Flirt4Free 5 days ago

Labella Slays Dick on Crossdressing Big Dick Sissy

Labella Slays Dick on Crossdressing Big Dick Sissy

XHamster 2 months ago

Sissy Mind WARP

Sissy Mind WARP

BigTitsLust 1 year ago

JOI Cuck Anal Training CEI Next Level - Luna Doll

JOI Cuck Anal Training CEI Next Level - Luna Doll

XHamster 11 months ago

Dressing up Sissy

61% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

Big strapon rips hung sissy whore gobbling chokes

Big strapon rips hung sissy whore gobbling chokes

AveXXX 2 days ago

Mistress Lady Renee - Making you dress - mp4

72% 0:16 / 14:03

Mistress Lady Renee - Making you dress - mp4

Clips4sale 1 year ago

Sissy in chastity - feminization - verbal instructions - anal training

HD 0:25 / 11:04

Sissy in chastity - feminization - verbal instructions - anal training

Clips4sale 1 month ago

Bi confusion sissy cock sucking trainer POV cum on face (whispers positive instructions no insults)

Bi confusion sissy cock sucking trainer POV cum on face (whispers positive instructions no insults)

Pornfact 1 month ago

Unexpected sissy male climax .

Unexpected sissy male climax .

SortPorn 1 week ago

siswet from mrhankeystoys glides effortlessly in is hot man pussy

siswet from mrhankeystoys glides effortlessly in is hot man pussy

Pornfact 4 days ago

Woman Fucks Her Husband in the Anus #044 Training Sissy Lesbian Dildo

Woman Fucks Her Husband in the Anus #044 Training Sissy Lesbian Dildo

XHamster 5 months ago

Anal and Face Fucking Sex Doll with Cum on Face Facial

Anal and Face Fucking Sex Doll with Cum on Face Facial

Pornfact 1 week ago

Elle Marz - Sissy Training And Draining

Elle Marz - Sissy Training And Draining

InPorn 6 months ago

Depth Training My Boytoy's Ass With A 46 Inch Depth Trainer Dildo

Depth Training My Boytoy's Ass With A 46 Inch Depth Trainer Dildo

XHamster 4 years ago

[823] Strap and Birch

76% 0:55 / 32:50

[823] Strap and Birch

Clips4sale 3 years ago

Gentle Bi Encouragment - Will You Suck Cock For Me?

Gentle Bi Encouragment - Will You Suck Cock For Me?

Pornzona 4 days ago

Extreme StepMom Throat Training: Heavy Gagging, ATM, Huge Anal Toys, Sissification, CBT and Golden Shower Finale! Cruel BDSM BBW Domme

Extreme StepMom Throat Training: Heavy Gagging, ATM, Huge Anal Toys, Sissification, CBT and Golden Shower Finale! Cruel BDSM BBW Domme

Juicexxx 2 months ago

Making You Soft Forever

61% HD 0:28 / 19:00

Making You Soft Forever

IWantClips 9 months ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years ago

Two Dominatrix Femdom Ritual Humiliates Submissive Male Slave Training & Feminization French Pegging

Two Dominatrix Femdom Ritual Humiliates Submissive Male Slave Training & Feminization French Pegging

Juicexxx 5 days ago

Amy Bllossom Private Show

56% HD 2:00 / 16:39

Amy Bllossom Private Show

Camster 11 months ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

XHamster 5 months ago

[F4A] Doll's Don't Move ~ Cruel Femdom Dollification and Hyper Feminization Audio Roleplay

[F4A] Doll's Don't Move ~ Cruel Femdom Dollification and Hyper Feminization Audio Roleplay

Lesbian8 1 year ago

POV Sissy Pegging - Custom for FRED

POV Sissy Pegging - Custom for FRED

Amateur8 4 years ago

Sissy & cuckold training

52% HD 1:01 / 11:51

Sissy & cuckold training

FapHouse 5 years ago

Sissy Slut Training Pet Shows How To Suck And Swallow Huge Loads

Sissy Slut Training Pet Shows How To Suck And Swallow Huge Loads

AveXXX 5 days ago

Leather Weather! The Best Leather

Leather Weather! The Best Leather

Some.Porn 1 year ago

can you make me cumm ?? - Part 2

61% 4K 2:00 / 4:52

can you make me cumm ?? - Part 2

Camster 2 weeks ago

Size Queen Sissy Boy Training with CEI

HD 0:39 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 6 days ago

Bella Brookz Private Show

52% HD 2:00 / 11:32

Bella Brookz Private Show

Flirt4Free 3 years ago

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