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.

Sissification Porn Videos (5,422)

Chat with AI
Powerful CFNM mistress pegs pathetic lad
100%
4:50
Powerful CFNM mistress pegs pathetic lad

wankoz 4 months ago

Snowball Feeding my Cum Hungry Cuck
92%
0:18
Snowball Feeding my Cum Hungry Cuck

Pornhub 1 year ago

Sexy Blonde Sissy Bailey Wilde in Chastity Fucked
57%
10:01
Sexy Blonde Sissy Bailey Wilde in Chastity Fucked

XVideos 10 months ago

Hot Maid Trans Women Fucking
54%
1:16
Hot Maid Trans Women Fucking

XVideos 1 year ago

I Assure you that you will never get out of the Cage again | MistressErica
89%
1:08
I Assure you that you will never get out of the Cage again | MistressErica

Pornhub 1 year ago

Redhead ultra slut Roxana humiliate her white pay sissy with her black lover.
78%
0:59
Redhead ultra slut Roxana humiliate her white pay sissy with her black lover.

XVideos 1 year ago

Petite Trans Jessica Moon Gives Trans Bailey Wilde a Blowjob
100%
11:32
Petite Trans Jessica Moon Gives Trans Bailey Wilde a Blowjob

XNXX 1 year ago

Dick Measuring Contest with Goddess / Femdom SPH / Goddess Alexa
90%
6:17
Dick Measuring Contest with Goddess / Femdom SPH / Goddess Alexa

Pornhub 3 years ago

Hot Trans Blonde Fucked Missionary
100%
7:07
Hot Trans Blonde Fucked Missionary

XVideos 9 months ago

Feminization C - Training Trailer
59%
3:34
Feminization C - Training Trailer

XNXX 2 years ago

HOTTEST Crossdresser Bailey Wilde Giving Blowjob
78%
3:04
HOTTEST Crossdresser Bailey Wilde Giving Blowjob

XVideos 5 months ago

Bounce - Sissy - Teaser
41%
1:54
Bounce - Sissy - Teaser

XVideos 3 years ago

Hot Blonde Femboy Bailey Wilde Photoshoot
52%
4:44
Hot Blonde Femboy Bailey Wilde Photoshoot

XVideos 1 year ago

Petite Trans Woman Rides Beautiful Trans Woman
73%
9:13
Petite Trans Woman Rides Beautiful Trans Woman

XVideos 7 months ago

Sissification Lecture "SISSY COCK and ASSHOLE EVOLUTION" Veronica Taboo Shows DILDOS, PLUGS, CAGES
90%
15:03
Sissification Lecture "SISSY COCK and ASSHOLE EVOLUTION" Veronica Taboo Shows DILDOS, PLUGS, CAGES

Pornhub 2 years ago

Sissy Whore Training Pt1
90%
0:55
Sissy Whore Training Pt1

Pornhub 3 years ago

British dominas dominating useless crossdressing sissy
73%
5:00
British dominas dominating useless crossdressing sissy

XNXX 3 years ago

Sissification
99%
25:52
Sissification

xHamster 5 years ago

Owned Sissy Slut Streams & Fucks herself Raw while Hotwife Femdom Goddess is Away! 4/5 Full Vid soon
89%
25:07
Owned Sissy Slut Streams & Fucks herself Raw while Hotwife Femdom Goddess is Away! 4/5 Full Vid soon

Pornhub 2 years ago

Your first task is coming from me now, my Sissi. Because I love it when you become a DWT and wear women's underwear, it will be great.
100%
16:14
Your first task is coming from me now, my Sissi. Because I love it when you become a DWT and wear women's underwear, it will be great.

XVideos 6 months ago

Anal Dildo Ass Trraineer
90%
11:04
Anal Dildo Ass Trraineer

Pornhub 1 year ago

Thirsty for Squirts - Sissification Trailer
20%
3:34
Thirsty for Squirts - Sissification Trailer

XNXX 2 years ago

[FayGrey] [Sold as a to Junko Enoshima] (JOI CEI CBT Petplay Sissification Anal Trainer)
70%
19:10
[FayGrey] [Sold as a to Junko Enoshima] (JOI CEI CBT Petplay Sissification Anal Trainer)

XVideos 4 years ago

Femdom JOI Dirty Talk & CEI while I Tease you about Bigger White Cock
89%
1:09
Femdom JOI Dirty Talk & CEI while I Tease you about Bigger White Cock

Pornhub 1 year ago

Crossdressing into Prom Queen
83%
4:43
Crossdressing into Prom Queen

XVideos 1 year ago

Girl for Step-Mommy Sissy Transformation Preview
89%
3:12
Girl for Step-Mommy Sissy Transformation Preview

Pornhub 1 year ago

30 Days to Sissy Day 4: Sissy Bimbo Quiz
91%
3:18
30 Days to Sissy Day 4: Sissy Bimbo Quiz

Pornhub 3 years ago

Hot Transgender Women Fucking
74%
0:59
Hot Transgender Women Fucking

XVideos 1 year ago

Mistress takes you to a gay bar
81%
10:56
Mistress takes you to a gay bar

XNXX 4 years ago

Petite Trans Woman Rides Crossdresser's Huge Cock
100%
2:36
Petite Trans Woman Rides Crossdresser's Huge Cock

XVideos 6 months ago

TS Jessica Moon Fucked Deep by TS Bailey Wilde
83%
4:56
TS Jessica Moon Fucked Deep by TS Bailey Wilde

XVideos 7 months ago

Sexy Blonde Sissy Bailey Wilde in Chastity Fucked
83%
10:01
Sexy Blonde Sissy Bailey Wilde in Chastity Fucked

XVideos 5 months ago

JOI Nico Robin & Nami Quiz, CEI, CBT, Ice Play French
91%
22:34
JOI Nico Robin & Nami Quiz, CEI, CBT, Ice Play French

Pornhub 5 years ago

Confessions of a Cam Girl: My Naughtiest Moments on Camera
100%
7:19
Confessions of a Cam Girl: My Naughtiest Moments on Camera

XVideos 6 months ago

SPH and BBC Pegging
90%
4:52
SPH and BBC Pegging

Pornhub 2 years ago

Denied - Feminization Instructions - Trailer
86%
3:34
Denied - Feminization Instructions - Trailer

XNXX 1 year ago

Shame - Sissy - Teaser
45%
2:23
Shame - Sissy - Teaser

XVideos 3 years ago

Bday Surprise - Feminized & Fucked by your Sissy Roommate FULL VID at LayneLovee Manyvids
93%
1:12
Bday Surprise - Feminized & Fucked by your Sissy Roommate FULL VID at LayneLovee Manyvids

Pornhub 1 year ago

Lucky - Teaser
50%
3:34
Lucky - Teaser

XVideos 2 years ago

Sexy Blonde Trans Woman Fucks Alternative Trans Woman Missionary
71%
0:46
Sexy Blonde Trans Woman Fucks Alternative Trans Woman Missionary

XVideos 1 year ago

Preview: Snowed in Cross Dressing Encouragement: GFE Role Play & Feminization Encouragement
91%
1:55
Preview: Snowed in Cross Dressing Encouragement: GFE Role Play & Feminization Encouragement

Pornhub 3 years ago

Roxana is now kicking her cuckold sissy slut with the high heels.
71%
0:31
Roxana is now kicking her cuckold sissy slut with the high heels.

XVideos 1 year ago

Pegging a cross dressing slut
98%
8:33
Pegging a cross dressing slut

xHamster 5 years ago

Hot Blonde Crossdresser Bailey Wilde Strokes Big Cock While Being Fucked
80%
2:59
Hot Blonde Crossdresser Bailey Wilde Strokes Big Cock While Being Fucked

XNXX 11 months ago

Cock Obsessed Whore
91%
7:52
Cock Obsessed Whore

Pornhub 5 years ago

Mind Hole - Awakening Your Mind Pussy - Sissy Enthrallment
50%
0:24
Mind Hole - Awakening Your Mind Pussy - Sissy Enthrallment

XVideos 1 year ago

Sissification Audio 4 Pack Be Gay for Dicks
96%
26:56
Sissification Audio 4 Pack Be Gay for Dicks

xHamster 2 years ago

FayGrey, Gremory mansion part 1. Akeno takes your servitude test (Joi Cei Ruin) fantasy roleplay
81%
13:06
FayGrey, Gremory mansion part 1. Akeno takes your servitude test (Joi Cei Ruin) fantasy roleplay

XVideos 5 years ago

DILDOGAME. DAY1.PART1. STEPBROTHER MY LITTLE HELPER
95%
40:31
DILDOGAME. DAY1.PART1. STEPBROTHER MY LITTLE HELPER

xHamster 5 years ago

Petite Trans Woman Rides Beautiful Trans Woman
88%
9:13
Petite Trans Woman Rides Beautiful Trans Woman

XNXX 7 months ago

Hairless Sissy Bitch
79%
7:54
Hairless Sissy Bitch

XVideos 4 years ago

Golden Shower Wets my SISSY Gurlfriend before FISTING Cumshot
90%
14:15
Golden Shower Wets my SISSY Gurlfriend before FISTING Cumshot

Pornhub 1 year ago

BG Redhead Latex Domme Fists Sissy for the first Time Pt 2 - Full Video on Veggiebabyy Manyvids
90%
0:55
BG Redhead Latex Domme Fists Sissy for the first Time Pt 2 - Full Video on Veggiebabyy Manyvids

Pornhub 2 years ago

Butt plug for luck
100%
0:26
Butt plug for luck

XVideos 8 months ago

Unleash your Fem for Me. Pegging my Sissy Boyfriend. Full 11Min OnlyFans|FEMFORHER
90%
3:38
Unleash your Fem for Me. Pegging my Sissy Boyfriend. Full 11Min OnlyFans|FEMFORHER

Pornhub 3 years ago

FayGrey, Kurumi JOI CEI Femdom
74%
18:38
FayGrey, Kurumi JOI CEI Femdom

XVideos 5 years ago

Sissy Husband Dressed and Fucked - Check out my Links for Full Video
90%
2:47
Sissy Husband Dressed and Fucked - Check out my Links for Full Video

Pornhub 2 years ago

[FayGrey] [mistress Erza's Slave#473] (Joi NoToys Wholesome Cuckolding Love Engagement OptionalNTR M
91%
29:27
[FayGrey] [mistress Erza's Slave#473] (Joi NoToys Wholesome Cuckolding Love Engagement OptionalNTR M

Pornhub 2 years ago

Crossdresser Makeover Transformation Into Woman by Girlfriend
86%
0:27
Crossdresser Makeover Transformation Into Woman by Girlfriend

XVideos 1 year ago

VR Gender Swap Into Hot StepSister: Grope & Felt Up
100%
0:30
VR Gender Swap Into Hot StepSister: Grope & Felt Up

XVideos 11 months ago

Slut Whore Trainer - Teaser
69%
2:34
Slut Whore Trainer - Teaser

XVideos 4 years ago

Sissy Training for Hotel Housekeeping Job
56%
12:45
Sissy Training for Hotel Housekeeping Job

XNXX 1 year ago

Getting Trained to please Cocks no Matter what they are Attached to GIRLS OR BOIS
91%
10:27
Getting Trained to please Cocks no Matter what they are Attached to GIRLS OR BOIS

Pornhub 5 years ago

Trans Kelsey Masters Fucked by Fuck Machine While Bailey Wilde Masturbates
3:04
Trans Kelsey Masters Fucked by Fuck Machine While Bailey Wilde Masturbates

XVideos 1 year ago

ex girlfriend walks in on you with a dildo up your butt and degrades you while you fuck yourself - veggiebabyy
74%
1:03
ex girlfriend walks in on you with a dildo up your butt and degrades you while you fuck yourself - veggiebabyy

XNXX 3 years ago

Heart Squirts - Teaser
87%
2:32
Heart Squirts - Teaser

XVideos 3 years ago

Sexy Petite Trans Woman Fucked Deep by Crossdresser
100%
4:59
Sexy Petite Trans Woman Fucked Deep by Crossdresser

XNXX 6 months ago

Sissy Hope Compilation 13
60%
10:43
Sissy Hope Compilation 13

XVideos 8 months ago

Nub - Sissy instructions - Chastity JOI
46%
3:34
Nub - Sissy instructions - Chastity JOI

XNXX 1 year ago

Hot Femboy Fucks Petite Trans Woman
100%
4:46
Hot Femboy Fucks Petite Trans Woman

XNXX 6 months ago

Fuck Machine Fucks Femboy Bailey Wilde
75%
3:51
Fuck Machine Fucks Femboy Bailey Wilde

XNXX 1 year ago

Bra for sissy transformation
40%
11:08
Bra for sissy transformation

XVideos 9 months ago

Trap Shows Cock
95%
0:17
Trap Shows Cock

XVideos 1 year ago

FILIPINA DOMINA PEGGING WHITE CHASTITY SLUT by DominaFire
90%
2:22
FILIPINA DOMINA PEGGING WHITE CHASTITY SLUT by DominaFire

Pornhub 3 years ago

Suck Chanel Santini's Cock
85%
6:37
Suck Chanel Santini's Cock

XVideos 6 years ago

Brainwashing Works if you Work Bitch!
91%
6:13
Brainwashing Works if you Work Bitch!

Pornhub 5 years ago

Please spread all over the internet !!️️
94%
0:22
Please spread all over the internet !!️️

XVideos 1 year ago

Love Treatment - Sissy Training Teaser
90%
3:34
Love Treatment - Sissy Training Teaser

XVideos 1 year ago

Sissy Hope Anal Training Teaser
83%
4:47
Sissy Hope Anal Training Teaser

XVideos 1 year ago

Hot Blonde Crossdresser Bailey Wilde Strokes Big Cock While Being Fucked
40%
2:59
Hot Blonde Crossdresser Bailey Wilde Strokes Big Cock While Being Fucked

XVideos 5 months ago

Related stars:
Bailey Wilde Chisholm Of Boston Jade Madison Jessica Moon Sissy Hope Lilly Mays Bobbywhiteprinceshumiliator Olivia Rose Jake Grand Todd Jones Lady Julina Crossdresser Ketty Enchantressthorne Casey Calvert Mspetrahunter Rider On The Floor The Other Rider On The Floor Kaiia Eve
Related categories:
Sissy Amateur Anal Femdom Feminization Transsexual Tranny Hd Porn Fetish Sexy Homemade Ass Verified Amateurs Joi Sissy Training Humiliation Femboy Solo Female