Sissy Anal Training (93,250)

The best and newest sissy anal training videos

Whored Out Office Sissy - Pegging POV with Elle Eros

66% HD 0:39 / 8:17

Whored Out Office Sissy - Pegging POV with Elle Eros

FapHouse 1 year ago

Katharine Cane Party on Jul 6, 2026 - Part 2

56% 4K 2:00 / 6:32

Katharine Cane Party on Jul 6, 2026 - Part 2

Flirt4Free 2 months ago

Felicity Fantasy Private Show

HD 2:00 / 1:26:27

Felicity Fantasy Private Show

Camster 5 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

Pretty Sissy Fuck Doll

HD 0:10 / 20:17

Pretty Sissy Fuck Doll

LoyalFans 1 month ago

Amber Sweeett Private Show

HD 2:00 / 17:11

Amber Sweeett Private Show

Flirt4Free 2 days ago

My owner becomes my SIssy

My owner becomes my SIssy

XHamster 2 years ago

Elizabeth Whiler Private Show

46% HD 2:00 / 6:55

Elizabeth Whiler Private Show

Camster 3 years ago

Mistress Baton’s Sissy Finishing School Part 4 - Strapping & Caning

Mistress Baton’s Sissy Finishing School Part 4 - Strapping & Caning

LoyalFans 2 months ago

(4K) Sissy Club Slut: Huge Strap-on and Deep Fisting Full Length 50 Minutes (4K)

65% 4K 0:30 / 53:35

(4K) Sissy Club Slut: Huge Strap-on and Deep Fisting Full Length 50 Minutes (4K)

Clips4sale 2 years ago

Playing with My Husband's Asshole

Playing with My Husband's Asshole

XHamster 2 years ago

8 INCH Strapon fucking my chastity slut in Latex

8 INCH Strapon fucking my chastity slut in Latex

XHamster 4 years ago

French dominatrix fucks her submissive husband part 2

French dominatrix fucks her submissive husband part 2

XHamster 2 years ago

BBW Femdom - Pegging Chaste Sissy Anal

BBW Femdom - Pegging Chaste Sissy Anal

XHamster 2 years ago

Worthless husband pegged in his boi pussy whilst pathetic cock is caged up

Worthless husband pegged in his boi pussy whilst pathetic cock is caged up

XHamster 3 years ago

Her Mission Is to Take Him Deep with Her Siswet From Mrhankeystoys

Her Mission Is to Take Him Deep with Her Siswet From Mrhankeystoys

XHamster 1 month ago

Bella Brookz Private Show

55% HD 2:00 / 5:11

Bella Brookz Private Show

Flirt4Free 2 years ago

Hailey Roses Private Show

57% HD 2:00 / 5:25

Hailey Roses Private Show

Flirt4Free 3 years 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

Detained and Fucked by Sinstress (mov)

Detained and Fucked by Sinstress (mov)

Clips4sale 7 months ago

SIT ON MY DILDO, GOOD BOY

SIT ON MY DILDO, GOOD BOY

XHamster 8 months ago

Bella Brookz Private Show

52% HD 2:00 / 11:32

Bella Brookz Private Show

Flirt4Free 3 years ago

Amateur thong-on movie scene – Amateur belt-on movie – Real wife bangs in good pegging her pliant hooby using a large toy, This babe makes greetings like a sissy slut. Escouple 08-26

Amateur thong-on movie scene – Amateur belt-on movie – Real wife bangs in good pegging her pliant hooby using a large toy, This babe makes greetings like a sissy slut. Escouple 08-26

SortPorn 1 week ago

Bizarre Sissy Bad Dragon Gaping and FemDom Aperture Destruction with Speculum Show Off by Mastix Mercer

Bizarre Sissy Bad Dragon Gaping and FemDom Aperture Destruction with Speculum Show Off by Mastix Mercer

Amateur8 9 months ago

Slave training in heat

Slave training in heat

Lesbian8 1 year ago

Viky & Mateo Private Show

59% HD 2:00 / 4:48

Viky & Mateo Private Show

Camster 8 months ago

He's been asking for so long. I saw for the first time what a male anal orgasm is.

He's been asking for so long. I saw for the first time what a male anal orgasm is.

XHamster 4 years ago

Bella Brookz Private Show

45% HD 2:00 / 14:02

Bella Brookz Private Show

Flirt4Free 3 years ago

Sweet & Daaniel Private Show

63% HD 2:00 / 14:05

Sweet & Daaniel Private Show

Camster 2 months ago

Anal training n. three - Miss Katryn dominated and pegged by Lady Sofia femdom headmistress

Anal training n. three - Miss Katryn dominated and pegged by Lady Sofia femdom headmistress

SortPorn 6 days ago

Extreme Anal Challenge - Strapon and 15-inch Dildo Until He Takes It All and Cums on My Black Nitrile Gloves

Extreme Anal Challenge - Strapon and 15-inch Dildo Until He Takes It All and Cums on My Black Nitrile Gloves

FapHouse 2 weeks ago

PROSTATE EXPLOSION big compilation

PROSTATE EXPLOSION big compilation

XHamster 2 years 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

Ashley Sinn Private Show

58% 4K 2:00 / 7:22

Ashley Sinn Private Show

Camster 11 months ago

My Bull Called, He Wants Us Both to Prepare Our Asses

53% HD 1:01 / 19:18

My Bull Called, He Wants Us Both to Prepare Our Asses

FapHouse 8 months ago

JOI Anal session training, sissy lesson - Sammy Altham

JOI Anal session training, sissy lesson - Sammy Altham

XHamster 4 months ago

”Bi-Curious Bro Gets A Sissy Sandwich”

”Bi-Curious Bro Gets A Sissy Sandwich”

TransHero 8 months ago

Bella Brookz Private Show

49% HD 2:00 / 9:32

Bella Brookz Private Show

Flirt4Free 3 years ago

Bella Brookz Private Show

63% HD 2:00 / 18:56

Bella Brookz Private Show

Camster 3 years ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 4 years ago

Red Lips Tease and Pussyplay

61% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Flirt4Free 3 years ago

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year ago

Harmoni Kalifornia's Sissy Spouse Mr. B***e (Pip) Experiences Anal Training from Sean

Harmoni Kalifornia's Sissy Spouse Mr. B***e (Pip) Experiences Anal Training from Sean

FreePorn8 11 months ago

Busty British MILF pegs office faggot with her huge strap-on

Busty British MILF pegs office faggot with her huge strap-on

AveXXX 2 weeks ago

Cana&rsquo_s Pet Training Joi Cbt Cei (Pet Play, Dildo Play, Chastity, NO HANDS, Denial, Ruined Orgasm)

Cana&rsquo_s Pet Training Joi Cbt Cei (Pet Play, Dildo Play, Chastity, NO HANDS, Denial, Ruined Orgasm)

XVideos 3 years ago

Sissy Anal JOI

65% HD 0:39 / 7:41

FapHouse 2 years ago

JOI for Anal CEI Ashley Sinclair

55% HD 0:39 / 7:03

JOI for Anal CEI Ashley Sinclair

FapHouse 4 months ago

Femdom Strict Sissy Training Session: Cock Sucking, CBT, Pegging & Fisting with Mistress Stellina (1080p)

HD 1:01 / 54:59

Femdom Strict Sissy Training Session: Cock Sucking, CBT, Pegging & Fisting with Mistress Stellina (1080p)

FapHouse 1 week ago

Whip and Fuck the Slut

67% HD 0:39 / 9:19

Whip and Fuck the Slut

FapHouse 2 years ago

Lilly Wayne Private Show

Lilly Wayne Private Show

Camster 2 years ago

Nazanin Hunter Private Show

59% HD 2:00 / 8:38

Nazanin Hunter Private Show

Flirt4Free 3 years ago

10 Depraved Tasks No Limits - Femom POV

42% HD 1:01 / 14:02

10 Depraved Tasks No Limits - Femom POV

FapHouse 4 months ago

Brittney & Elvis Private Show

58% HD 2:00 / 6:22

Brittney & Elvis Private Show

Flirt4Free 3 years ago

Viky & Mateo Private Show

53% HD 2:00 / 32:44

Viky & Mateo Private Show

Camster 7 months ago

Helena Red Private Show

64% HD 2:00 / 10:43

Helena Red Private Show

Flirt4Free 3 years ago

Elizabeth Whiler Private Show

54% HD 2:00 / 13:42

Elizabeth Whiler Private Show

Camster 3 years ago

show me your stretched anal hole. bisexual husband in chastity belt as he gets fucked by mistress!

63% HD 0:15 / 5:13

show me your stretched anal hole. bisexual husband in chastity belt as he gets fucked by mistress!

PornBox 3 years ago

Chit Chat with Katie

55% HD 2:00 / 22:31

Chit Chat with Katie

Flirt4Free 9 years ago

Junior & Brittney Private Show

64% HD 2:00 / 4:02

Junior & Brittney Private Show

Flirt4Free 2 years ago

Junior & Brittney Private Show

Junior & Brittney Private Show

Camster 2 years ago

Kandi More & Jamer Private Show

57% HD 2:00 / 5:32

Kandi More & Jamer Private Show

Flirt4Free 3 years ago

Viky & Mateo Private Show

56% HD 2:00 / 11:13

Viky & Mateo Private Show

Camster 7 months ago

Elizabeth Whiler Private Show

37% HD 2:00 / 6:55

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Hailey Roses Private Show

51% HD 2:00 / 24:20

Hailey Roses Private Show

Flirt4Free 3 years ago

Elizabeth Whiler Private Show

57% HD 2:00 / 6:03

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Red Lips Tease and Pussyplay

49% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Camster 3 years ago

DLVids Diapered Feminization & Hole Training SoftDomme IPOD

DLVids Diapered Feminization & Hole Training SoftDomme IPOD

Clips4sale 1 year ago

Femdom POV Sissy Training Pleasure Him

48% HD 0:39 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 5 months ago

$let\'s get naughty - Part 2$ 4K 2:00 / 4:52

let\'s get naughty - Part 2

Flirt4Free 1 month ago

First time anal for virgin sissy

First time anal for virgin sissy

XHamster 7 months ago

Ares & Adara Private Show

61% HD 2:00 / 15:45

Ares & Adara Private Show

Camster 1 year ago

Viky & Mateo Private Show

55% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 7 months ago

Femdom Humiliation, Sissy Training: Ready 4 Real Cock

42% HD 1:01 / 11:49

Femdom Humiliation, Sissy Training: Ready 4 Real Cock

FapHouse 5 months ago

Ares & Adara Private Show

54% HD 2:00 / 9:20

Ares & Adara Private Show

Flirt4Free 1 year ago

Hailey Roses Private Show

60% HD 2:00 / 24:20

Hailey Roses Private Show

Camster 3 years 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

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

58% 0:39 / 25:09

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

FapHouse 10 months ago

Hailey Roses Private Show

49% HD 2:00 / 13:45

Hailey Roses Private Show

Flirt4Free 2 years ago

Elizabeth Whiler Private Show

48% HD 2:00 / 9:53

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Handjob with prostate massage for my sissy boy

Handjob with prostate massage for my sissy boy

XHamster 2 years ago

Elizabeth Whiler Private Show

51% HD 2:00 / 13:22

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Amelia Sweety Private Show

60% HD 2:00 / 4:47

Amelia Sweety Private Show

Flirt4Free 10 months ago

oubliette films - goddess serena pegging her sissy slaves boi pussy

oubliette films - goddess serena pegging her sissy slaves boi pussy

BDSMShip 3 years ago

VIVIENNE L'AMOUR - PANTY SLUT PEGGED EVERY WHICH WAY

HD 0:19 / 18:13

VIVIENNE L'AMOUR - PANTY SLUT PEGGED EVERY WHICH WAY

Clips4sale 3 years ago

Veronica Mendez Private Show

HD 2:00 / 22:16

Veronica Mendez Private Show

Camster 2 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

Bella Brookz Private Show

52% HD 2:00 / 7:57

Bella Brookz Private Show

Flirt4Free 3 years ago

Electra Joness Party on Aug 10, 2026 - Part 3

69% HD 2:00 / 1:36:56

Electra Joness Party on Aug 10, 2026 - Part 3

Camster 4 weeks ago

Training my wife to anal. First anal stretching. Enema. Ep 24943

Training my wife to anal. First anal stretching. Enema. Ep 24943

XHamster 7 months ago

Chloe Riveiro Private Show

4K 2:00 / 12:12

Chloe Riveiro Private Show

Flirt4Free 4 days ago

Bella Brookz Private Show

60% HD 2:00 / 14:02

Bella Brookz Private Show

Camster 3 years ago

Femdom Pegging Gangbang

51% 0:39 / 11:17

Femdom Pegging Gangbang

FapHouse 6 months ago

Secret Sissy Fantasy- Mistress Kendra, femdom, chastity, make me bi

63% HD 0:37 / 11:26

Secret Sissy Fantasy- Mistress Kendra, femdom, chastity, make me bi

IWantClips 1 year ago

$let\'s cum together - Part 5$ 63% 4K 2:00 / 4:52

let\'s cum together - Part 5

Camster 1 month ago

Chastity PEE and FISTING for SISSY slave

Chastity PEE and FISTING for SISSY slave

XHamster 2 years ago

Kandi More & Jamer Private Show

61% HD 2:00 / 56:41

Kandi More & Jamer Private Show

Camster 3 years ago

Bella Brookz Private Show

61% HD 2:00 / 20:02

Bella Brookz Private Show

Camster 3 years ago

Ashley Ness Private Show

63% 4K 2:00 / 9:43

Ashley Ness Private Show

Flirt4Free 2 months ago

Darsy Pearly Private Show

65% HD 2:00 / 9:56

Darsy Pearly Private Show

Camster 1 month ago

can you make me cum ? - Part 2

47% HD 2:00 / 4:52

can you make me cum ? - Part 2

Flirt4Free 5 months ago

Femdom Pegging Gangbang

65% HD 1:01 / 12:36

Femdom Pegging Gangbang

FapHouse 6 months ago

Bella Brookz Private Show

67% HD 2:00 / 4:24

Bella Brookz Private Show

Camster 3 years ago

Electra Joness Party on Aug 10, 2026 - Part 3

64% HD 2:00 / 1:36:56

Electra Joness Party on Aug 10, 2026 - Part 3

Flirt4Free 4 weeks ago

ANAL INSTRUCTING ASSGASM

ANAL INSTRUCTING ASSGASM

BigTitsLust 1 year ago

Man Trains His Wife for Lesbian Sex #099 Full Video Long Pegging

Man Trains His Wife for Lesbian Sex #099 Full Video Long Pegging

XHamster 7 months ago

Cum Like a Girl - Feminized for a Girls Only JOI

52% 4K 0:29 / 20:17

Cum Like a Girl - Feminized for a Girls Only JOI

Clips4sale 1 year ago

Brittney & Elvis Private Show

61% HD 2:00 / 6:22

Brittney & Elvis Private Show

Camster 3 years ago

Bella Brookz Private Show

59% HD 2:00 / 16:09

Bella Brookz Private Show

Flirt4Free 3 years ago

Bella Brookz Private Show

54% HD 2:00 / 9:01

Bella Brookz Private Show

Camster 3 years ago

Anal Tease: JOI, Edging & Denial Adventures

Anal Tease: JOI, Edging & Denial Adventures

GiveMeAPorn 1 week ago

PROSTATE ORGASM COMPILATION SISSY

PROSTATE ORGASM COMPILATION SISSY

XHamster 4 years ago

Elizabeth Whiler Private Show

55% HD 2:00 / 31:36

Elizabeth Whiler Private Show

Camster 3 years ago

alexis amadahy and jade sissy training and strap on

alexis amadahy and jade sissy training and strap on

PornOne 8 years ago

Andromeda Cute Private Show

66% HD 2:00 / 20:53

Andromeda Cute Private Show

Camster 1 month ago

Elizabeth Whiler Private Show

60% HD 2:00 / 6:03

Elizabeth Whiler Private Show

Camster 3 years ago

Top 10 Chastity Ideas Vol.2

Top 10 Chastity Ideas Vol.2

XHamster 9 months ago

April Benson Private Show

55% HD 2:00 / 14:52

April Benson Private Show

Flirt4Free 2 years ago

Hot Mom Domme's Sissy Training - Wife Pegs Husband Anal

Hot Mom Domme's Sissy Training - Wife Pegs Husband Anal

TatBabes 2 months ago

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Eporner 3 years ago

JOI Echo With My Big Black Dick - Luna Doll

JOI Echo With My Big Black Dick - Luna Doll

XHamster 10 months ago

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