This is an adult website

This website contains age-restricted materials including nudity and explicit depictions of sexual activity. By entering, you confirm that you are at least 18 years of age or older.

Sissy Training Porn Videos (9,398)

Chat with AI
Sissy Brainwashing Stage 1
91%
4:55
Sissy Brainwashing Stage 1

Pornhub 5 years ago

Pegging my sissy slut whilst spanking his fat ass
99%
1:22
Pegging my sissy slut whilst spanking his fat ass

xHamster 2 years ago

2 Asian Domintrixes vs 1 White Sissy
91%
2:20
2 Asian Domintrixes vs 1 White Sissy

Pornhub 3 years ago

Brunette and Chastity slave part 2
93%
17:59
Brunette and Chastity slave part 2

xHamster 1 year ago

Pegging my Sissy Slut
97%
4:28
Pegging my Sissy Slut

xHamster 1 year ago

Yummy Cum CEI Sissy Slut Training by Goddess Chy Latte Cum Slut Femdom Make Me Bi
90%
7:23
Yummy Cum CEI Sissy Slut Training by Goddess Chy Latte Cum Slut Femdom Make Me Bi

xHamster 2 years ago

It Gets Bigger and Bigger
90%
0:49
It Gets Bigger and Bigger

xHamster 1 year ago

Horny Femboy Slut Intro Sissy Training
92%
1:20
Horny Femboy Slut Intro Sissy Training

Pornhub 3 years ago

Crave Cock - JOI
91%
10:05
Crave Cock - JOI

SpankBang 4 years ago

Sissy Trainer Facesitting Discipline #FemdomRAW
90%
0:47
Sissy Trainer Facesitting Discipline #FemdomRAW

Pornhub 3 years ago

Wife pegs husband and trains his pathetic ass
95%
1:54
Wife pegs husband and trains his pathetic ass

xHamster 2 years ago

ANAL PROBE INTENSE PROSTATE ORGASM - Pornhub Gay
91%
5:06
ANAL PROBE INTENSE PROSTATE ORGASM - Pornhub Gay

Pornhub 3 years ago

Sissy Slutcore 2 by Musicmonk
84%
21:01
Sissy Slutcore 2 by Musicmonk

SpankBang 3 years ago

Sissy Faggot Mind Scramble Enhanced Erotic Audio by Tara Smith Femdom Submissive Male Training
91%
7:09
Sissy Faggot Mind Scramble Enhanced Erotic Audio by Tara Smith Femdom Submissive Male Training

Pornhub 5 years ago

Sissy training
95%
16:30
Sissy training

SpankBang 5 years ago

Sissy Scarlet Sky Cum Compilation!
91%
3:20
Sissy Scarlet Sky Cum Compilation!

Pornhub 3 years ago

Sissy Mantra : Female Domination POV Sissification Feminization
91%
3:45
Sissy Mantra : Female Domination POV Sissification Feminization

Pornhub 3 years ago

Sissy Slut Training - Preview
66%
2:34
Sissy Slut Training - Preview

XNXX 4 years ago

Busty Mistress Mary Fucks her Cuckold Hubby in the Ass and goes to Fuck with BBC! Full Version on OF
91%
3:14
Busty Mistress Mary Fucks her Cuckold Hubby in the Ass and goes to Fuck with BBC! Full Version on OF

Pornhub 4 years ago

Wife Sissy "D" and the Humbler Part 1
91%
8:57
Wife Sissy "D" and the Humbler Part 1

xHamster 1 year ago

EAT YOUR OWN CUM SISSY BOI YOU CAN DO IT
99%
4:41
EAT YOUR OWN CUM SISSY BOI YOU CAN DO IT

xHamster 5 years ago

Strapon Deepthroat and Facesitting Latex Sissy by DominaFire
91%
2:16
Strapon Deepthroat and Facesitting Latex Sissy by DominaFire

Pornhub 3 years ago

HOME SISSY TRAINNING
94%
1:29
HOME SISSY TRAINNING

XNXX 1 year ago

Shy Femboy Gets a Handjob from his Girlfriend with Cum on his Belly
90%
5:58
Shy Femboy Gets a Handjob from his Girlfriend with Cum on his Belly

Pornhub 3 years ago

Beautiful 18 Year old Transsexual Girl Masturbates in the Forest
93%
5:23
Beautiful 18 Year old Transsexual Girl Masturbates in the Forest

Pornhub 2 years ago

Clitty Busts after Fucking my Doll
92%
12:11
Clitty Busts after Fucking my Doll

Pornhub 2 years ago

Hattabi4ik Sissy Boy Gold Rain Compilation
90%
9:27
Hattabi4ik Sissy Boy Gold Rain Compilation

Pornhub 3 years ago

Hattabi4ik Cumshot Compilation
90%
7:34
Hattabi4ik Cumshot Compilation

Pornhub 4 years ago

Sissy Anal Gape Farting!
91%
4:27
Sissy Anal Gape Farting!

Pornhub 5 years ago

Become the Sissy at the Circle Jerk ENHANCED AUDIO VERSION
91%
5:56
Become the Sissy at the Circle Jerk ENHANCED AUDIO VERSION

Pornhub 4 years ago

Fucked and on the Edge of Orgasm - Sissy Slut Training
100%
1:09
Fucked and on the Edge of Orgasm - Sissy Slut Training

xHamster 1 year ago

Gay Cum Eating Reprogramming Ft Trans Femdom
90%
0:36
Gay Cum Eating Reprogramming Ft Trans Femdom

Pornhub 2 years ago

Snowbunny fucks SISSY with BBC Dildo, heavy VERBAL HUMILIATION.
100%
11:24
Snowbunny fucks SISSY with BBC Dildo, heavy VERBAL HUMILIATION.

xHamster 1 year ago

Подарок ко Дню Святого Валентина) - римминг, страпон
91%
19:31
Подарок ко Дню Святого Валентина) - римминг, страпон

Pornhub 5 years ago

You know you want it
97%
2:33
You know you want it

xHamster 5 years ago

Self Facial while Fucking my Ass Balls Deep
91%
0:56
Self Facial while Fucking my Ass Balls Deep

Pornhub 4 years ago

Femdom Sissy Humiliation Tube Vids
58%
7:57
Femdom Sissy Humiliation Tube Vids

XNXX 3 years ago

Guys, I have to Confess that i'm no Longer a Virgin
92%
5:39
Guys, I have to Confess that i'm no Longer a Virgin

Pornhub 1 year ago

You know you want it
97%
2:33
You know you want it

xHamster 5 years ago

DominaFire Pegging her Tied up Slave Rough
90%
3:36
DominaFire Pegging her Tied up Slave Rough

Pornhub 3 years ago

Sissy Bimbo Training
91%
6:25
Sissy Bimbo Training

Pornhub 5 years ago

Sissy Sophie Fucking her Dildo like a Slut! (Compilation)
91%
10:50
Sissy Sophie Fucking her Dildo like a Slut! (Compilation)

Pornhub 3 years ago

Sissy Maid Cums in Chastity and in Bondage and Swallows her Sissy Cum
92%
15:24
Sissy Maid Cums in Chastity and in Bondage and Swallows her Sissy Cum

Pornhub 1 year ago

Chastity Sissy Riding new XXL Toy - TRAILER - Pornhub Gay
91%
1:45
Chastity Sissy Riding new XXL Toy - TRAILER - Pornhub Gay

Pornhub 3 years ago

Sissy Training Day 3 - Femdom Feminization
90%
6:27
Sissy Training Day 3 - Femdom Feminization

Pornhub 4 years ago

Sissygasm from Anal Masturbation in Sissy Slut with Closed Clit in Chastity_sc.29
90%
12:34
Sissygasm from Anal Masturbation in Sissy Slut with Closed Clit in Chastity_sc.29

Pornhub 3 years ago

Cunt on a Stool - she Turns his Butt inside a Huge Vagina
9:15
Cunt on a Stool - she Turns his Butt inside a Huge Vagina

CrazyPorn 4 years ago

Japanese Sissy Fucking Erotic Video♡i'm going to have Sex with you Cum Inside.【女装 男の娘 Ladyboy】
91%
3:03
Japanese Sissy Fucking Erotic Video♡i'm going to have Sex with you Cum Inside.【女装 男の娘 Ladyboy】

Pornhub 2 years ago

CD take black dildo 2
94%
2:59
CD take black dildo 2

XVideos 2 years ago

You're not Fooling anyone - SISSY! - Pornhub Gay
91%
3:22
You're not Fooling anyone - SISSY! - Pornhub Gay

Pornhub 2 years ago

Girl Crying as she is Poked from behind by a Dildo💦japanese Crossdresser Masturbation
91%
11:03
Girl Crying as she is Poked from behind by a Dildo💦japanese Crossdresser Masturbation

Pornhub 3 years ago

Mistress sissifies her husband and pounds his tight ass hole
98%
1:49
Mistress sissifies her husband and pounds his tight ass hole

xHamster 2 years ago

Chastity PEE and FISTING for SISSY slave
100%
10:36
Chastity PEE and FISTING for SISSY slave

xHamster 2 years ago

Sissification Lecture "caged Sissy" Chastity Belts, Jerk, Sissygasm by Mistress Veronica Taboo
91%
16:47
Sissification Lecture "caged Sissy" Chastity Belts, Jerk, Sissygasm by Mistress Veronica Taboo

Pornhub 5 years ago

Doggy Style Anal Fingering Training with Bunny Girl Cosplay Vol.7
90%
5:03
Doggy Style Anal Fingering Training with Bunny Girl Cosplay Vol.7

Pornhub 3 years ago

Sissy Training 2 hour affirmation video
64%
1:58:31
Sissy Training 2 hour affirmation video

XNXX 6 years ago

Femdom Girlfriend Teaches you how to Suck Cock
91%
8:22
Femdom Girlfriend Teaches you how to Suck Cock

Pornhub 4 years ago

My Lunch Break... LIKES HER FINGERS MORE!!!
90%
16:03
My Lunch Break... LIKES HER FINGERS MORE!!!

Pornhub 3 years ago

An impactful spelling lesson: sissy learns to spell with paddling
73%
14:01
An impactful spelling lesson: sissy learns to spell with paddling

XVideos 4 years ago

Cute Filthy Whore - Pegging and Golden Shower
80%
11:01
Cute Filthy Whore - Pegging and Golden Shower

XNXX 5 years ago

Cum Addict, by Jlodalisque
99%
14:09
Cum Addict, by Jlodalisque

xHamster 5 years ago

Neural Adaptation - Feminization Instructions
60%
3:34
Neural Adaptation - Feminization Instructions

XNXX 1 year ago

A Sexy Fun Time
91%
15:28
A Sexy Fun Time

Pornhub 3 years ago

Born to Suck - Encoraged Bi, Sissy Training, Sissification
90%
0:53
Born to Suck - Encoraged Bi, Sissy Training, Sissification

Pornhub 2 years ago

My Favourite Video
90%
23:26
My Favourite Video

Pornhub 2 years ago

Sissy Shorts Captions 5 - Girlfriend's Kitty
99%
1:00
Sissy Shorts Captions 5 - Girlfriend's Kitty

xHamster 5 years ago

Slowly Fisting while Hot Cum Drips out of Him. Beautiful Prostate Orgasm!!!!
91%
6:24
Slowly Fisting while Hot Cum Drips out of Him. Beautiful Prostate Orgasm!!!!

Pornhub 3 years ago

ANAL MARATHON 2: endurance
96%
15:31
ANAL MARATHON 2: endurance

xHamster 5 years ago

Sissy Cock Trainer
97%
8:12
Sissy Cock Trainer

xHamster 6 years ago

Slut School Dick Sucking Class
91%
10:55
Slut School Dick Sucking Class

Pornhub 4 years ago

Slut Girl Peeing her Pants by Playing Tricks on her Asshole💖crossdresser Masturbation
91%
9:28
Slut Girl Peeing her Pants by Playing Tricks on her Asshole💖crossdresser Masturbation

Pornhub 2 years ago

Rimming pegging = perfect sex for a guy (comments at the end)
64%
15:31
Rimming pegging = perfect sex for a guy (comments at the end)

XVideos 5 years ago

SissyXXX (5)
91%
22:04
SissyXXX (5)

SpankBang 4 years ago

Sissy Fag Cock Training Ft Trans Femdom
91%
0:35
Sissy Fag Cock Training Ft Trans Femdom

Pornhub 2 years ago

Screaming Girl with Intense Piston💖japanese Crossdresser Masturbation
91%
10:23
Screaming Girl with Intense Piston💖japanese Crossdresser Masturbation

Pornhub 2 years ago

Curious Blonde Wife Natural Tits Anal Masturbation Handjob Sissy Husband Fucking Hairy Pussy
91%
5:13
Curious Blonde Wife Natural Tits Anal Masturbation Handjob Sissy Husband Fucking Hairy Pussy

Pornhub 4 years ago

Penis Worship JOI Edit
20:00
Penis Worship JOI Edit

Love4Porn 4 years ago

Rub that Sissy Clitty on my Feet--reward Time Sissy!!
90%
9:59
Rub that Sissy Clitty on my Feet--reward Time Sissy!!

Pornhub 3 years ago

Cock hypno cei
81%
10:05
Cock hypno cei

SpankBang 4 years ago

Femdom Cuckold used Condom Feeding
90%
0:59
Femdom Cuckold used Condom Feeding

Pornhub 4 years ago

Related stars:
Miss Brat Mistress Susi Lauracdtv Mspetrahunter Polysweet Pau1sweet Alina Li Brandi Belle Charlie Garcia Veronica Rodriguez
Related categories:
Sissy Hd Porn Verified Amateurs Amateur Transgender Anal Femdom Fetish Masturbation Cumshot Exclusive Big Ass Babe Pegging 18 25 Strapon Toys Chastity