Sissy Training Sex Videos (147,104)

Hand Job Training the Bondage Pet

53% HD 1:01 / 12:21

Hand Job Training the Bondage Pet

FapHouse 1 month ago

Red Lips Tease and Pussyplay

61% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Camster 3 years ago

bi confusion swallow his cum sissy faggot CEI (point of view cumshot femdom training)

bi confusion swallow his cum sissy faggot CEI (point of view cumshot femdom training)

Itsrealamateurs 1 month ago

Sissy Edging Challenge - Earn Your Sissygasm. Orvilina Trains You to Be Her Perfect Panty-Wearing Gooner. Includes JOI, Encouragement, Orgasm Control, Sissyfication & Sissygasm

Sissy Edging Challenge - Earn Your Sissygasm. Orvilina Trains You to Be Her Perfect Panty-Wearing Gooner. Includes JOI, Encouragement, Orgasm Control, Sissyfication & Sissygasm

Clips4sale 1 week ago

Red Lips Tease and Pussyplay

61% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Flirt4Free 3 years ago

Ich ficke deinen Sissy Arsch!

Ich ficke deinen Sissy Arsch!

XHamster 4 years ago

Sissy Training - guide to became sissy - (No_3)

Sissy Training - guide to became sissy - (No_3)

Itsrealamateurs 3 weeks ago

Learning to CUM from the ASS... First PROSTATE ORGASM!

Learning to CUM from the ASS... First PROSTATE ORGASM!

XHamster 2 years ago

Sissy Mind WARP

Sissy Mind WARP

BigTitsLust 1 year ago

Manu Eyngri Private Show

HD 2:00 / 10:00

Manu Eyngri Private Show

Camster 1 week ago

Sissy training part-1

Sissy training part-1

Eporner 3 months ago

Jen Holly Private Show

73% HD 2:00 / 4:45

Jen Holly Private Show

Camster 1 year ago

Special feminization training with your girlfriend Yae Miko (Femdom JOI)

Special feminization training with your girlfriend Yae Miko (Femdom JOI)

XHamster 1 month ago

Mistress's Command: Edge & Slap Control Game (Male Submission) Clip 2

Mistress's Command: Edge & Slap Control Game (Male Submission) Clip 2

XHamster 8 months 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

Feminization Training: Sissy takes big cock in her ass

Feminization Training: Sissy takes big cock in her ass

AnalRZ 1 year ago

Suck Cock and Swallow Hot Cum - Obey Your Mistress

Suck Cock and Swallow Hot Cum - Obey Your Mistress

XHamster 1 year ago

Your Mind is Weak, Sissy

Your Mind is Weak, Sissy

SortPorn 3 years ago

Sissy's Feminization

Sissy's Feminization

BigTitsLust 5 months ago

$let\'s have some fun - Part 2$ 4K 2:00 / 4:51

let\'s have some fun - Part 2

Camster 2 weeks ago

Throat Fuck Training with Miss Katie

Throat Fuck Training with Miss Katie

XHamster 4 weeks ago

Bi Humiliation & Cum Clean up with a Female Audience

51% 1:01 / 8:42

Bi Humiliation & Cum Clean up with a Female Audience

FapHouse 1 year ago

Cum Eating instruction CEI #1 By Bestsissycaptions

Cum Eating instruction CEI #1 By Bestsissycaptions

FreePorn8 1 year ago

Good boys eat cum

Good boys eat cum

XHamster 1 year ago

How I Destroyed My Cock (REAL Soft Cock Training) [MOV Format]

54% 1:00 / 10:40

How I Destroyed My Cock (REAL Soft Cock Training) [MOV Format]

Clips4sale 5 months ago

Sissy Slave Training MyFreeShemale.com

Sissy Slave Training MyFreeShemale.com

Fapcat 3 years ago

Aching For Penis

Aching For Penis

SortPorn 1 year ago

Guys, for the First Time I Got Myself Fucked by the Pantry Boy in a Moving Train, He Fucked Me Hard and Tore My Pussy

51% HD 1:01 / 9:48

Guys, for the First Time I Got Myself Fucked by the Pantry Boy in a Moving Train, He Fucked Me Hard and Tore My Pussy

FapHouse 10 months ago

Training You, My Sissy, to Love Cock

55% HD 0:10 / 10:14

Training You, My Sissy, to Love Cock

LoyalFans 1 month ago

Sissy training

Dafreeporn 4 years 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

Pro Sissy Training Level

Pro Sissy Training Level

Sunporno 2 years ago

Jennas Suprise

XHamster 3 years ago

Femdom Humiliation - Oops, I've Made You Gay!

45% HD 1:01 / 18:20

Femdom Humiliation - Oops, I've Made You Gay!

FapHouse 4 months ago

Stuffed Woman. the Hole Overflows as It Is Full to the Top

62% 0:39 / 11:41

Stuffed Woman. the Hole Overflows as It Is Full to the Top

FapHouse 6 months ago

Jen Holly Private Show

51% HD 2:00 / 8:35

Jen Holly Private Show

Flirt4Free 1 year ago

Elizabeth Whiler Private Show

53% HD 2:00 / 13:42

Elizabeth Whiler Private Show

Camster 3 years ago

MY KRISTEN: Full Feminine Transformation, Corset Training, & Total Identity Correction

MY KRISTEN: Full Feminine Transformation, Corset Training, & Total Identity Correction

XHamster 8 months ago

FEMDOM STRAPON GANGBANG

Premium HD 12:31

FEMDOM STRAPON GANGBANG

XNXXGold 1 month ago

FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

XHamster 4 years ago

Viky & Mateo Private Show

51% HD 2:00 / 11:13

Viky & Mateo Private Show

Camster 7 months 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

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year ago

Double Dommes Fuck the Bimbo Slut 4K ft Mistress Damazonia

63% 4K 0:22 / 14:14

Double Dommes Fuck the Bimbo Slut 4K ft Mistress Damazonia

Clips4sale 2 years ago

Pale babe moves her lips Slowly and Sucks BBC close-up

Pale babe moves her lips Slowly and Sucks BBC close-up

XGroovy 4 years ago

FEMDOM STRAPON GANGBANG

Premium HD 12:31

FEMDOM STRAPON GANGBANG

XVideosRed 1 month ago

We Love Spreading and Playing with Our Big Asses.

We Love Spreading and Playing with Our Big Asses.

XHamster 2 months ago

Brittney & Elvis Private Show

64% HD 2:00 / 6:22

Brittney & Elvis Private Show

Camster 3 years ago

Elizabeth Whiler Private Show

47% HD 2:00 / 9:53

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Sex Tool Hero - riding the A educate

Sex Tool Hero - riding the A educate

SortPorn 3 years ago

Femdom Pegging Gangbang

65% HD 1:01 / 12:36

Femdom Pegging Gangbang

FapHouse 6 months ago

elf femboy in chastity belt gets tight ass stretched by bbc cock and fuck machine until cum

elf femboy in chastity belt gets tight ass stretched by bbc cock and fuck machine until cum

Lesbian8 1 year ago

Elizabeth Whiler Private Show

45% HD 2:00 / 6:55

Elizabeth Whiler Private Show

Camster 3 years ago

Sharon J Private Show

Sharon J Private Show

Camster 3 days ago

Dressing up Sissy

55% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

femdom goddess nikki kit karina king foot worship porn video

femdom goddess nikki kit karina king foot worship porn video

BDSMShip 1 year ago

Jen Holly Private Show

64% HD 2:00 / 5:45

Jen Holly Private Show

Camster 1 year ago

Fun Feminization

52% HD 0:10 / 5:34

Fun Feminization

LoyalFans 1 year ago

POV Cuckold vol 30

POV Cuckold vol 30

XHamster 6 months ago

Domnafire straps her sissy to the edge and fucks him raw

Domnafire straps her sissy to the edge and fucks him raw

AveXXX 1 week ago

Femdom Republic Sissy Training And Feminisation a Feminine

Femdom Republic Sissy Training And Feminisation a Feminine

DrTuber 2 weeks ago

Making My Husband into a Cuckold Sissy!

49% 0:11 / 9:49

Making My Husband into a Cuckold Sissy!

Clips4sale 2 years ago

Bella Brookz Private Show

52% HD 2:00 / 11:32

Bella Brookz Private Show

Flirt4Free 3 years ago

Sissies Obey In Trance

Sissies Obey In Trance

LoyalFans 2 years ago

sissy joyce - goddess annie i love their helpless porn video

sissy joyce - goddess annie i love their helpless porn video

BDSMShip 1 year ago

Lazy Wife Take a Nap, but He Wakes Her up with a Dick in Her Ass

Lazy Wife Take a Nap, but He Wakes Her up with a Dick in Her Ass

FapHouse 3 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 8 months ago

Sissy Cum Dump! By Ruby Onyx

Sissy Cum Dump! By Ruby Onyx

Clips4sale 1 month ago

Delivery Guy Becomes a Sissy

65% HD 0:39 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 6 months ago

FBB BBC PEGGING SLAYER TRIO - Lexa ft Goddess Sydney Thunder & Rose Fit

63% 4K 0:19 / 10:39

FBB BBC PEGGING SLAYER TRIO - Lexa ft Goddess Sydney Thunder & Rose Fit

Clips4sale 8 months ago

PROSTATE EXPLOSION big compilation

PROSTATE EXPLOSION big compilation

XHamster 2 years ago

Hardcore Up Close Femdom Bi Encouragement Oral and CEI

Hardcore Up Close Femdom Bi Encouragement Oral and CEI

FreePorn8 3 years ago

Sissy Training level up now and takes cum in the mouth

HD 0:56 / 18:14

Sissy Training level up now and takes cum in the mouth

Clips4sale 3 weeks 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

Sissy Meets Alpha

58% HD 0:10 / 7:15

Sissy Meets Alpha

LoyalFans 2 years ago

Sissy Chastity Training with Two BBC

51% 0:11 / 20:25

Sissy Chastity Training with Two BBC

Clips4sale 1 year ago

Ruin It, Sissy Slut!

HD 0:26 / 14:17

Ruin It, Sissy Slut!

Clips4sale 2 years ago

Jasmine Flowers Pegging Training, femdom Goddess

Jasmine Flowers Pegging Training, femdom Goddess

XHamster 1 month ago

Alpha Couple Teaches How to Suck Cock

60% HD 0:39 / 11:53

Alpha Couple Teaches How to Suck Cock

FapHouse 1 year ago

Ive Always Wanted To Do This

Ive Always Wanted To Do This

LoyalFans 2 years ago

The Secret of My Body

48% 2:00 / 5:16

The Secret of My Body

Camster 6 months ago

Not for Boring Couples - Vol 2

Not for Boring Couples - Vol 2

XHamster 1 week ago

Kenia & Rene Private Show

Kenia & Rene Private Show

Camster 1 year ago

Sarah Stanley Private Show

Sarah Stanley Private Show

Camster 3 weeks ago

Sissy Slut Gets Strapon Experience - Full Version

Sissy Slut Gets Strapon Experience - Full Version

XHamster 4 years ago

can you make me cumm ?? - Part 2

56% 4K 2:00 / 4:52

can you make me cumm ?? - Part 2

Camster 1 month ago

CUM BLOCKING HANDJOB. Female POV

CUM BLOCKING HANDJOB. Female POV

XHamster 4 years ago

Elizabeth Whiler Private Show

Elizabeth Whiler Private Show

Camster 3 years ago

Dildo Dolly 2

58% HD 1:01 / 15:31

FapHouse 3 years ago

Strap on fun and asshole licking

66% 1:01 / 14:14

Strap on fun and asshole licking

FapHouse 4 years ago

Cuckold Sissy Maid in Training (4K)

68% 4K 0:13 / 10:36

Cuckold Sissy Maid in Training (4K)

Clips4sale 3 months 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

Adrenaline on the Train. Caught in the Toilet

Adrenaline on the Train. Caught in the Toilet

XHamster 3 months ago

Nefertiti & Demian Private Show

60% HD 2:00 / 9:43

Nefertiti & Demian Private Show

Camster 3 years ago

Viky & Mateo Private Show

67% HD 2:00 / 4:48

Viky & Mateo Private Show

Camster 7 months ago

Jen Holly Private Show

55% HD 2:00 / 4:53

Jen Holly Private Show

Camster 1 year ago

Milking in Sissy Mouth and Pegging Training

59% HD 0:39 / 16:24

Milking in Sissy Mouth and Pegging Training

FapHouse 1 year ago

Wife Making Cute Sissy Clit Squirt In Her Mouth, Then Swallows

Wife Making Cute Sissy Clit Squirt In Her Mouth, Then Swallows

XHamster 4 years ago

Doggy Style Pregnant Masturbate Lush Clit Spread Bush Pussy

69% 4K 2:00 / 7:28

Doggy Style Pregnant Masturbate Lush Clit Spread Bush Pussy

Flirt4Free 3 years ago

Jen Holly Private Show

61% HD 2:00 / 15:26

Jen Holly Private Show

Camster 1 year ago

Jhanne Cherry Private Show

46% HD 2:00 / 40:31

Jhanne Cherry Private Show

Camster 11 months ago

Diaper Bimbo Bitch Trainer - Mistress Ashley Edmonds

61% HD 0:10 / 16:35

Diaper Bimbo Bitch Trainer - Mistress Ashley Edmonds

LoyalFans 9 months ago

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Eporner 3 years ago

Best Femdom Pegging Compilation by Dominafire

Best Femdom Pegging Compilation by Dominafire

XHamster 2 years ago

Russian Domme Pounds Boy's Ass with Massive Strapon

Russian Domme Pounds Boy's Ass with Massive Strapon

Jizzberry 3 years ago

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

48% HD 0:39 / 10:01

30 Days Mtf Complete Transformation - Slut Training - Crossdressing - Bimbofication - Femdom POV

FapHouse 1 year ago

Elizabeth Whiler Private Show

63% HD 2:00 / 6:27

Elizabeth Whiler Private Show

Camster 3 years ago

Sissy Buttplug Humiliation Lick Your Pink Tail Clean, Slut

HD 1:01 / 18:04

Sissy Buttplug Humiliation Lick Your Pink Tail Clean, Slut

FapHouse 1 month ago

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

let\'s get naughty - Part 2

Flirt4Free 4 weeks ago

Jen Holly Private Show

61% HD 2:00 / 11:09

Jen Holly Private Show

Flirt4Free 1 year ago

Magically Transformed Sissy ABDL - Penny Barber POV

Magically Transformed Sissy ABDL - Penny Barber POV

Lesbian8 6 months ago

My cum eating chastity slave gets to clean my feet

My cum eating chastity slave gets to clean my feet

XHamster 1 year ago

Tiny Dick Losers Become Sissy Whores for Alexa Creed

Tiny Dick Losers Become Sissy Whores for Alexa Creed

XHamster 2 months ago

pissing in the mouth. let s open your mouth i ll fill it. lick my pussy and feet in stockings.

pissing in the mouth. let s open your mouth i ll fill it. lick my pussy and feet in stockings.

PissVids 3 years ago

Jen Holly Private Show

67% HD 2:00 / 8:35

Jen Holly Private Show

Camster 1 year ago

Elizabeth Whiler Private Show

51% HD 2:00 / 8:57

Elizabeth Whiler Private Show

Flirt4Free 3 years ago

Bi Encouragement Training - Take 2 Of My Mans Cumshots

Bi Encouragement Training - Take 2 Of My Mans Cumshots

XHamster 1 month ago

Elizabeth Whiler Private Show

54% HD 2:00 / 13:22

Elizabeth Whiler Private Show

Camster 3 years ago

Bella Brookz Private Show

65% HD 2:00 / 7:26

Bella Brookz Private Show

Flirt4Free 3 years ago

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