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Sissy Anal Training Porn Videos (702)

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Sissy in High Heels and Chastity goes Outdoors with a Vibrating Wand in the Ass, Falls to the Floor
90%
3:22
Sissy in High Heels and Chastity goes Outdoors with a Vibrating Wand in the Ass, Falls to the Floor

Pornhub 3 years ago

Crossdressing Amateur Sissy trying to Ride her first Dildo in Tight Virgin Ass - Pornhub Gay
92%
2:21
Crossdressing Amateur Sissy trying to Ride her first Dildo in Tight Virgin Ass - Pornhub Gay

Pornhub 3 years ago

HEADPHONE WARNING Training Ass to take XL Atlas mr Hanky Toy Deeper, Painal Gape
92%
16:48
HEADPHONE WARNING Training Ass to take XL Atlas mr Hanky Toy Deeper, Painal Gape

Pornhub 3 years ago

Sissy Soldier Slut Anal Training (short Version)
91%
5:58
Sissy Soldier Slut Anal Training (short Version)

Pornhub 5 years ago

Phone Call w Panty-wearing Sissy Boy
91%
15:20
Phone Call w Panty-wearing Sissy Boy

Pornhub 6 years ago

Sissy Fucks Bussy with Cum
93%
3:24
Sissy Fucks Bussy with Cum

Pornhub 1 year ago

Sissygasm from Anal Masturbation in Sissy Slut with Closed Clit in Chastity_sc.30
91%
9:05
Sissygasm from Anal Masturbation in Sissy Slut with Closed Clit in Chastity_sc.30

Pornhub 3 years ago

Mexican Sissy Juice
90%
1:32
Mexican Sissy Juice

Pornhub 2 years ago

BBC Buttfuck
91%
6:09
BBC Buttfuck

Pornhub 6 years ago

Sissy Michelle Cums in Chastity Cage from Fuck Machine
91%
0:52
Sissy Michelle Cums in Chastity Cage from Fuck Machine

Pornhub 4 years ago

I Love Riding Hard FAT Dick until I Cum! | SissyGasm! | Hands Free CumShot!
92%
12:15
I Love Riding Hard FAT Dick until I Cum! | SissyGasm! | Hands Free CumShot!

Pornhub 4 years ago

Anal Fisting Training for my Sissy Slut Petra!
90%
2:14
Anal Fisting Training for my Sissy Slut Petra!

Pornhub 4 years ago

Transgender Devil Deep Anal with 11 Inch Dildo
90%
9:11
Transgender Devil Deep Anal with 11 Inch Dildo

Pornhub 2 years ago

POV... you just Started Fucking my Ass
88%
1:02
POV... you just Started Fucking my Ass

Pornhub 2 years ago

Watch libidinous Goddess Alexa
100%
8:07
Watch libidinous Goddess Alexa

PornHat 2 years ago

PEGGING Training for SISSY Husband
91%
13:13
PEGGING Training for SISSY Husband

Pornhub 3 years ago

ANAL Stretching Training for CHASTITY SISSY Slave
90%
9:03
ANAL Stretching Training for CHASTITY SISSY Slave

Pornhub 1 year ago

Sissy Slave Gets Sissygasm in Chastity from Anal Masturbation_3
92%
13:05
Sissy Slave Gets Sissygasm in Chastity from Anal Masturbation_3

Pornhub 3 years ago

Transgender Anastasia Harris Wearing Devil Costume for Halloween Passionately Rides 8 Inch Dildo
89%
5:05
Transgender Anastasia Harris Wearing Devil Costume for Halloween Passionately Rides 8 Inch Dildo

Pornhub 2 years ago

Transgender DEEP Anal Play W/ Feet Licking & Sucking
92%
5:58
Transgender DEEP Anal Play W/ Feet Licking & Sucking

Pornhub 2 years ago

SISSY ANAL Adventures - DIAPERS Lesson In CHASTITY With Big BUTT PLUG And PEE
89%
6:28
SISSY ANAL Adventures - DIAPERS Lesson In CHASTITY With Big BUTT PLUG And PEE

FapCat 4 years ago

Tiny Femboy Training his little Hole with HUGE Dildo
89%
2:23
Tiny Femboy Training his little Hole with HUGE Dildo

Pornhub 3 years ago

Sex Machine Huge Anal Dildo
91%
8:44
Sex Machine Huge Anal Dildo

Pornhub 1 year ago

Hard Anal Training for Sissy
90%
3:53
Hard Anal Training for Sissy

Pornhub 3 years ago

Soft Warm Anal Femboy
89%
1:37
Soft Warm Anal Femboy

Pornhub 2 years ago

Quick Sissy Anal Training - Pornhub Gay
89%
14:03
Quick Sissy Anal Training - Pornhub Gay

Pornhub 3 years ago

Test Big Plug Tunnel , Anal Dilatation Training
88%
21:29
Test Big Plug Tunnel , Anal Dilatation Training

Pornhub 4 years ago

Sissy Femboy Pounds her Ass with 8 Inch Thrusting & Vibrating Dildo | Anal Play
88%
2:03
Sissy Femboy Pounds her Ass with 8 Inch Thrusting & Vibrating Dildo | Anal Play

Pornhub 2 years ago

Analathletics Anal Obsessions: College Student Absolutely Loves Stretching his Ass with Huge Toys - Pornhub Gay
91%
19:46
Analathletics Anal Obsessions: College Student Absolutely Loves Stretching his Ass with Huge Toys - Pornhub Gay

Pornhub 4 years ago

Fat Bad Dragon Busts my Boy Hole Wide Open Pt 2 - Pornhub Gay
88%
0:57
Fat Bad Dragon Busts my Boy Hole Wide Open Pt 2 - Pornhub Gay

Pornhub 2 years ago

Sissy follows Mistress Gie's Order to Show Viewers Close up Anal Workout
100%
12:46
Sissy follows Mistress Gie's Order to Show Viewers Close up Anal Workout

Pornhub 4 years ago

Sublime Goddess Alexa
100%
7:49
Sublime Goddess Alexa

PornHat 1 year ago

Sissygasm Challenge Day 3: Butt Plug
80%
2:07
Sissygasm Challenge Day 3: Butt Plug

Pornhub 4 years ago

Sissy with Tattoos Twerks a Big Ass
90%
6:09
Sissy with Tattoos Twerks a Big Ass

Pornhub 4 years ago

Jessie Finally Fits the Flare of her new Dildo in her Ass
100%
3:22
Jessie Finally Fits the Flare of her new Dildo in her Ass

Pornhub 2 years ago

Krissy the Sissy’s Compilation
91%
27:39
Krissy the Sissy’s Compilation

Pornhub 5 years ago

Slut Training - Huge Toys, Chastity and Ruined Orgasms
91%
2:01
Slut Training - Huge Toys, Chastity and Ruined Orgasms

Pornhub 4 years ago

Sissy got all Dressed up just to be Put to Drink Beers via Anal by her Alpha Male
90%
4:11
Sissy got all Dressed up just to be Put to Drink Beers via Anal by her Alpha Male

Pornhub 3 years ago

Sissy Ride
91%
6:10
Sissy Ride

Pornhub 6 years ago

Midnight Snack for my Boipussy (muffins and Dildo in my Asshole)
89%
2:06
Midnight Snack for my Boipussy (muffins and Dildo in my Asshole)

Pornhub 2 years ago

Denial and Ruin
91%
26:35
Denial and Ruin

Pornhub 3 years ago

Sissy Anal Masturbation Emptying a Beer Bottle in her Asshole
91%
4:09
Sissy Anal Masturbation Emptying a Beer Bottle in her Asshole

Pornhub 4 years ago

Bubble Butt Sissy Boy Loves to Fuck his Asshole on Cam Pt 1 FULL VID on LayneLovee Manyvids - Pornhub Gay
88%
0:41
Bubble Butt Sissy Boy Loves to Fuck his Asshole on Cam Pt 1 FULL VID on LayneLovee Manyvids - Pornhub Gay

Pornhub 2 years ago

Masturbate like a Girl - Sissy Anal JOI to Sissygasm by Goddess Nikki Kit
0:28
Masturbate like a Girl - Sissy Anal JOI to Sissygasm by Goddess Nikki Kit

Pornhub 1 year ago

Crossdressing Femboy Sissy at Public Parking Lot with Buttplug and in Latex Leggings
92%
1:23
Crossdressing Femboy Sissy at Public Parking Lot with Buttplug and in Latex Leggings

Pornhub 3 years ago

Sissy in Flat Chastity Cage trying to Fit Huge Magic Wand in her Boipussy
91%
1:23
Sissy in Flat Chastity Cage trying to Fit Huge Magic Wand in her Boipussy

Pornhub 2 years ago

Caged Sissy Properly Masturbating with Fucking Machine and Vibrator until Sissygasm
90%
6:29
Caged Sissy Properly Masturbating with Fucking Machine and Vibrator until Sissygasm

Pornhub 3 years ago

Sissy`s Private Anal Marathon
100%
4:49
Sissy`s Private Anal Marathon

Pornhub 1 year ago

Sissy Lucy Fucked by Big Black Dildo on the Fucking Machine
92%
4:35
Sissy Lucy Fucked by Big Black Dildo on the Fucking Machine

Pornhub 4 years ago

Anal Play Training for the Sissy Slut
92%
6:26
Anal Play Training for the Sissy Slut

Pornhub 5 years ago

Femboy Cummes in 1 Minute :3 🙀🤙
90%
1:13
Femboy Cummes in 1 Minute :3 🙀🤙

Pornhub 2 years ago

Pink Sissy Maid Gets Caught Playing with her Doll and made to have a Sissygasm
91%
11:19
Pink Sissy Maid Gets Caught Playing with her Doll and made to have a Sissygasm

Pornhub 1 year ago

Sissy Fixed and Chained Up, Riding Dildo
90%
8:59
Sissy Fixed and Chained Up, Riding Dildo

Pornhub 1 year ago

First Time Anal with my Toy - Pornhub Gay
88%
0:52
First Time Anal with my Toy - Pornhub Gay

Pornhub 2 years ago

Femdom First Time JOI CEI And Anal Training
1:16
Femdom First Time JOI CEI And Anal Training

FapCat 4 years ago

Sissy Riding Dildo on Table
88%
5:14
Sissy Riding Dildo on Table

Pornhub 1 year ago

The only right Choice is White Boy in Chastity and the only Sex he can have is Anal - Pornhub Gay
91%
9:04
The only right Choice is White Boy in Chastity and the only Sex he can have is Anal - Pornhub Gay

Pornhub 5 years ago

House rules for sissies
74%
5:55
House rules for sissies

XNXX 6 years ago

Femboy De México Estrena Su Dildo Hasta Venirse
92%
2:08
Femboy De México Estrena Su Dildo Hasta Venirse

Pornhub 3 years ago

Horny Boy Rides Dildo till He’s Satisfied - Pornhub Gay
89%
1:44
Horny Boy Rides Dildo till He’s Satisfied - Pornhub Gay

Pornhub 3 years ago

Riding a Dildo in the Shower & Ass to Mouth until I Cum, here my Loud Moaning Orgasm - Pornhub Gay
90%
8:38
Riding a Dildo in the Shower & Ass to Mouth until I Cum, here my Loud Moaning Orgasm - Pornhub Gay

Pornhub 4 years ago

Sissy Hands Free Orgasm - Anal Training
91%
1:18
Sissy Hands Free Orgasm - Anal Training

Pornhub 6 years ago

SMOKING for my SISSY Girlfriend and PLUGGING her Sweet Ass
93%
5:54
SMOKING for my SISSY Girlfriend and PLUGGING her Sweet Ass

Pornhub 3 years ago

Sissy Boi Anal Training by Goddess Lana
91%
6:48
Sissy Boi Anal Training by Goddess Lana

Pornhub 5 years ago

Anal Dildo Machine Pounding Orgasm
86%
7:54
Anal Dildo Machine Pounding Orgasm

Pornhub 1 year ago

4k Vulgar Femboy Riding a Dildo and Enjoyed ( Sissy Crossdress )
91%
4:30
4k Vulgar Femboy Riding a Dildo and Enjoyed ( Sissy Crossdress )

Pornhub 6 years ago

FAILED SISSY SELF FUCK! Sex Machine Dildo Fell off before Sissygasm. TS Veronica Taboo Smoking Vape.
89%
13:02
FAILED SISSY SELF FUCK! Sex Machine Dildo Fell off before Sissygasm. TS Veronica Taboo Smoking Vape.

Pornhub 4 years ago

Sissy Riding Dildo on Wasch Maschine - Pornhub Gay
88%
5:05
Sissy Riding Dildo on Wasch Maschine - Pornhub Gay

Pornhub 1 year ago

Anal PLUG and CHOCOLATE MESSY Play with SISSY Girlfriend
100%
10:25
Anal PLUG and CHOCOLATE MESSY Play with SISSY Girlfriend

Pornhub 2 years ago

Big Butt Trans CD Sissy Maid Feminization Sissification Training
86%
15:13
Big Butt Trans CD Sissy Maid Feminization Sissification Training

Pornhub 3 years ago

Slutty Sissy Anal Fuck Machine - Pornhub Gay
90%
10:30
Slutty Sissy Anal Fuck Machine - Pornhub Gay

Pornhub 2 years ago

Daily Evening Training with my Dildo
91%
1:14
Daily Evening Training with my Dildo

Pornhub 4 years ago

Horny Sissy Daniella in Train - Pornhub Gay
88%
15:26
Horny Sissy Daniella in Train - Pornhub Gay

Pornhub 1 year ago

Horny Sissy on way Home
88%
14:00
Horny Sissy on way Home

Pornhub 1 year ago

Early Sissy Slut Formation and Depravation Episodes - Compilation I
91%
27:20
Early Sissy Slut Formation and Depravation Episodes - Compilation I

Pornhub 4 years ago

ANAL DILDO RIDE
90%
2:41
ANAL DILDO RIDE

Pornhub 4 years ago

Teen Boy Riding Dildo for the first Time Leads to Multiple Cumshots Supervised Femdom Sissy Training - Pornhub Gay
92%
7:48
Teen Boy Riding Dildo for the first Time Leads to Multiple Cumshots Supervised Femdom Sissy Training - Pornhub Gay

Pornhub 4 years ago

Cant Stop Shaking after first Attempt with Mr. Hankey’s Giant Goliath Dildo - Pornhub Gay
91%
1:30
Cant Stop Shaking after first Attempt with Mr. Hankey’s Giant Goliath Dildo - Pornhub Gay

Pornhub 5 years ago

Simple Butt Fun - Pornhub Gay
91%
6:05
Simple Butt Fun - Pornhub Gay

Pornhub 4 years ago

Purple Hair Sissy Wrecks Asshole with Double Sissygasm
91%
18:37
Purple Hair Sissy Wrecks Asshole with Double Sissygasm

Pornhub 6 years ago

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