Sissy Training - Sex Videos (154,930)

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

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 5 years 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 2 years ago

Angelica Swiss Party on Oct 21, 2025

61% 4K 2:00 / 2:03:16

Angelica Swiss Party on Oct 21, 2025

Flirt4Free 11 months ago

Amateur Huge Strap-on Pegging Session

HD 0:39 / 20:52

Amateur Huge Strap-on Pegging Session

FapHouse 1 week ago

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year ago

Sissy Cumslut for Asian Homewrecker CEI

53% HD 0:29 / 19:57

Sissy Cumslut for Asian Homewrecker CEI

IWantClips 1 year ago

Jhanne Cherry Private Show

52% HD 2:00 / 8:06

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Spanking My Sissybitch

Spanking My Sissybitch

XHamster 4 days ago

Viky & Mateo Private Show

55% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 8 months ago

Peg Curious - Sharing My Man W Roommate

71% 0:39 / 26:10

Peg Curious - Sharing My Man W Roommate

FapHouse 3 months ago

Vends-ta-culotte - Anal training and strap-on pegging for a submissive man

Vends-ta-culotte - Anal training and strap-on pegging for a submissive man

XHamster 3 days ago

Playing with My Husband's Asshole

Playing with My Husband's Asshole

XHamster 2 years ago

Femdom y humillaci&oacute_n total. Total Femdom and Humiliation

Premium HD 33:26

Femdom y humillaci&oacute_n total. Total Femdom and Humiliation

XNXXGold 6 months ago

Suck Cock and Swallow Hot Cum - Obey Your Mistress

Suck Cock and Swallow Hot Cum - Obey Your Mistress

XHamster 1 year ago

Group Bi Training with My Three Girlfriends

Group Bi Training with My Three Girlfriends

XHamster 3 months ago

Elizabeth Whiler Private Show

52% HD 2:00 / 13:22

Elizabeth Whiler Private Show

Flirt4Free 4 years ago

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

61% HD 0:39 / 47:50

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

FapHouse 1 month ago

Fucked and on the Edge of Orgasm - Sissy Slut Training

65% HD 1:01 / 14:43

Fucked and on the Edge of Orgasm - Sissy Slut Training

FapHouse 1 year ago

Submissive Sluts volume 4

Submissive Sluts volume 4

XHamster 3 months ago

Slut Training for Slaves

Slut Training for Slaves

FapHouse 1 month ago

Size Queen Sissy Boy Training with CEI

69% HD 1:01 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 3 months ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

XHamster 8 months ago

Gentle Bi Encouragement - Will You Suck Cock For Me?

Gentle Bi Encouragement - Will You Suck Cock For Me?

XHamster 1 year ago

Real cuckold wife wants to suck cock together !!!

Real cuckold wife wants to suck cock together !!!

XHamster 9 months ago

The Lust of Sissy 3D Saga - Supportive Sugardaddy

49% HD 0:39 / 12:03

The Lust of Sissy 3D Saga - Supportive Sugardaddy

FapHouse 1 year ago

Peg Curious - Sharing My Man W Roommate

Peg Curious - Sharing My Man W Roommate

XHamster 3 months ago

Give up Your Life to Serve Me

HD 0:39 / 11:39

Give up Your Life to Serve Me

FapHouse 1 month ago

Blonde femdom trains a sissy in latex and heels inside a sleek German dungeon

Blonde femdom trains a sissy in latex and heels inside a sleek German dungeon

Yesvids 2 months ago

Sissy is filled with 100cm extrem dildo - part 2 of 2

Sissy is filled with 100cm extrem dildo - part 2 of 2

XHamster 2 years ago

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

59% 1:01 / 20:06

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

FapHouse 1 month ago

Sissy Gamer Gurl: Feminization & Throat Fucking Part 1 of 3 (1080p)

65% HD 1:01 / 17:26

Sissy Gamer Gurl: Feminization & Throat Fucking Part 1 of 3 (1080p)

FapHouse 1 month ago

Cuckold 2 (lick My Toilet Clean!)

59% HD 0:39 / 5:36

Cuckold 2 (lick My Toilet Clean!)

FapHouse 1 year ago

Goddess Sissy Training Penis Worshiper CEI

Goddess Sissy Training Penis Worshiper CEI

ALOTPorn 4 years ago

JOI Sissy - Be My Dirty Little Bitch

63% HD 1:01 / 11:29

JOI Sissy - Be My Dirty Little Bitch

FapHouse 3 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

$Katharine Kane\'s Handcuffed Blowjob$ 64% HD 2:00 / 19:35

Katharine Kane\'s Handcuffed Blowjob

Flirt4Free 9 years ago

Sexy Wife with Big Strapon pegging her Husband with Handjob

Sexy Wife with Big Strapon pegging her Husband with Handjob

XHamster 1 year ago

Bi Femdom Blowjob POV, Two MILF Mouths One Cock, Bisexual Encouragement

57% HD 1:01 / 10:19

Bi Femdom Blowjob POV, Two MILF Mouths One Cock, Bisexual Encouragement

FapHouse 1 month 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

INSTITUTION X - Prostate Milking Butthole Training Pspot Cumming COMPILATION 1-2

INSTITUTION X - Prostate Milking Butthole Training Pspot Cumming COMPILATION 1-2

KAMS 1 year ago

Jhanne Cherry Private Show

55% HD 2:00 / 27:22

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Good boys eat cum

Good boys eat cum

XHamster 2 years ago

Mistress Susi - the Straight Slaves First Sissy Blowjob

Mistress Susi - the Straight Slaves First Sissy Blowjob

XHamster 1 month ago

Tiny Blonde Rubbing Her Clit Hard and Fast

48% HD 2:00 / 4:07

Tiny Blonde Rubbing Her Clit Hard and Fast

Flirt4Free 9 years ago

Pissing CFNM domina punishes sissy in BDSM lesson

Pissing CFNM domina punishes sissy in BDSM lesson

Some.Porn 1 year ago

Mistress raises her sissy whore. anal training pussy licking

Mistress raises her sissy whore. anal training pussy licking

Itsrealamateurs 1 week ago

lick my pussy after pissing. oh yes good bitch. feminization of the stepbrother.

lick my pussy after pissing. oh yes good bitch. feminization of the stepbrother.

PissVids 3 years ago

Tia Tizzianni - Sissy Riley Joi Sexual Skills Training

Tia Tizzianni - Sissy Riley Joi Sexual Skills Training

Nuvid 1 week ago

Sexy Asian Mistress Dominates You

66% 0:39 / 11:30

Sexy Asian Mistress Dominates You

FapHouse 3 months ago

Jhanne Cherry Private Show

47% HD 2:00 / 22:11

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Emily & Stesha Private Show

47% 4K 2:00 / 5:57

Emily & Stesha Private Show

Flirt4Free 9 months ago

teaseandthankyou - mandy marx look into my gorgeous eyes while im pegging you but dont shoot too soon porn video

teaseandthankyou - mandy marx look into my gorgeous eyes while im pegging you but dont shoot too soon porn video

BDSMShip 1 year ago

Jhanne Cherry Private Show

52% HD 2:00 / 8:21

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Sissy Training- Blowjob CEI HYP

Sissy Training- Blowjob CEI HYP

Eporner 5 months ago

Mistress training sissies to play together

Mistress training sissies to play together

AbXXX 7 years ago

Mistress gives Sissy a Ruined Orgasm in Chastity Cage - Massive Load of Cum Rubbed on Mask and Fed to Her

Mistress gives Sissy a Ruined Orgasm in Chastity Cage - Massive Load of Cum Rubbed on Mask and Fed to Her

XHamster 1 year ago

Edelnutte Fabiennes Outen

Edelnutte Fabiennes Outen

XHamster 2 weeks ago

Sissygasm Training: My Cockhungry Femboi Learns to Serve and Suffer

Sissygasm Training: My Cockhungry Femboi Learns to Serve and Suffer

LoyalFans 10 months ago

PROSTATE ORGASM COMPILATION SISSY

PROSTATE ORGASM COMPILATION SISSY

XHamster 4 years ago

Deep Strap-on Lesson for a Sissy Slut’s Ass

57% HD 1:01 / 9:23

Deep Strap-on Lesson for a Sissy Slut’s Ass

FapHouse 3 weeks ago

Blonde Sex Slave Inseminated in Steel Shackles

Blonde Sex Slave Inseminated in Steel Shackles

XHamster 1 month ago

Electra Joness Party on Apr 13, 2026 - Part 3

57% 4K 2:00 / 1:00:15

Electra Joness Party on Apr 13, 2026 - Part 3

Flirt4Free 5 months ago

wife makes stranger cum and then her husband licks it up

wife makes stranger cum and then her husband licks it up

XHamster 1 year ago

Harmoni Kalifornia's Sissy Husband Mr. Bruce Experiences Anal Training from Sean

Harmoni Kalifornia's Sissy Husband Mr. Bruce Experiences Anal Training from Sean

Xfeed 1 year ago

Emily & Stesha Private Show

4K 2:00 / 12:14

Emily & Stesha Private Show

Flirt4Free 5 months ago

Bi Sissy Training

74% HD 1:01 / 34:42

Bi Sissy Training

FapHouse 6 months ago

Femdom Fisting by 2 Asian Dommes

Femdom Fisting by 2 Asian Dommes

XHamster 1 year ago

Julie and Liza's Latex Doll

69% HD 0:10 / 19:56

Julie and Liza's Latex Doll

LoyalFans 8 months ago

Female POV - feel like a girl

Female POV - feel like a girl

XHamster 3 years ago

Jhanne Cherry Private Show

58% 4K 2:00 / 21:44

Jhanne Cherry Private Show

Flirt4Free 1 year ago

It's my birthday, she gave me full package...all holes in one day

It's my birthday, she gave me full package...all holes in one day

FapHouse 2 months ago

Teaching My Cuckold - SNOWBALLING & HUMILIATION

63% 1:01 / 20:17

Teaching My Cuckold - SNOWBALLING & HUMILIATION

FapHouse 3 years ago

SLUT TRAINING BFF

66% HD 0:10 / 11:22

SLUT TRAINING BFF

LoyalFans 3 days ago

Jhanne Cherry Private Show

51% 4K 2:00 / 22:26

Jhanne Cherry Private Show

Flirt4Free 1 year ago

What a Ridiculous Sissy

57% 1:01 / 18:12

What a Ridiculous Sissy

FapHouse 2 years ago

Ruth Oliver Private Show

67% 4K 2:00 / 18:06

Ruth Oliver Private Show

Flirt4Free 4 months ago

Husband Turned Girlfriend Pt 5

54% HD 0:15 / 20:29

Husband Turned Girlfriend Pt 5

IWantClips 3 years ago

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

66% HD 1:01 / 47:50

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

FapHouse 1 month ago

Hospitality Whores (full scene 4k)

54% 4K 0:30 / 42:01

Hospitality Whores (full scene 4k)

IWantClips 2 years ago

Sissy Training

XHamster 7 months ago

Sissy slut fuck

57% HD 0:25 / 11:32

Sissy slut fuck

IWantClips 3 months ago

Bi Encouragement - Let Me Help You Give Your First Blowjob

58% 1:01 / 12:42

Bi Encouragement - Let Me Help You Give Your First Blowjob

FapHouse 1 year ago

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Eporner 3 years ago

Therapy session for sissy boys

Therapy session for sissy boys

XHamster 2 years ago

Randy Moore Fucks Lance Hart in the Ass with Strapon

Randy Moore Fucks Lance Hart in the Ass with Strapon

Fetishpapa 1 month ago

Camilla Polls Private Show

55% 4K 2:00 / 5:37

Camilla Polls Private Show

Flirt4Free 1 year ago

Zoey Evans Private Show

HD 2:00 / 13:29

Zoey Evans Private Show

Flirt4Free 1 week ago

Humiliation and food crushing for sissy Zombie: Giada Da Vinci disappointed, makes him eat the wilted roses

HD 0:25 / 11:07

Humiliation and food crushing for sissy Zombie: Giada Da Vinci disappointed, makes him eat the wilted roses

Clips4sale 3 days ago

Sissy Academy Part 1

Sissy Academy Part 1

XHamster 1 year ago

High Class Sissy Trained - Mistress T

High Class Sissy Trained - Mistress T

AbXXX 5 years ago

Slut Training

FapHouse 2 days ago

Emily & Stesha Private Show

53% 4K 2:00 / 12:53

Emily & Stesha Private Show

Flirt4Free 8 months ago

Prissy sissy dolly - Maid to be used

62% 0:30 / 13:35

Prissy sissy dolly - Maid to be used

Clips4sale 2 years 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

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

Rubber doll anal sissyfication training on rubber sissy doll

Rubber doll anal sissyfication training on rubber sissy doll

Clips 4 days ago

LOSER EXPOSED: The Sissy Madison Files - make me bi - bisexual encouragement - loser exposed - sissy training - slut

LOSER EXPOSED: The Sissy Madison Files - make me bi - bisexual encouragement - loser exposed - sissy training - slut

XHamster 2 weeks ago

Viuda Nagra Private Show

52% HD 2:00 / 52:49

Viuda Nagra Private Show

Flirt4Free 5 years 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

SISSY SLUT FUCKED WITH 8 INCH STRAPON by DominaFire

SISSY SLUT FUCKED WITH 8 INCH STRAPON by DominaFire

XHamster 4 years ago

Pegging my Sissy Slut

Pegging my Sissy Slut

XHamster 2 weeks ago

Aisha Goldenstein Private Show

4K 2:00 / 19:25

Aisha Goldenstein Private Show

Flirt4Free 1 week ago

you must always be under lock and key. chastity, always.

you must always be under lock and key. chastity, always.

PornBox 1 week ago

The Chastity Fuck

The Chastity Fuck

XHamster 5 days ago

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

Headmistress ANAL SEXTOY MILKING and ORAL PLEASURE

MatureTubeHere 4 years ago

Dominant-bitch, sissy training

Dominant-bitch, sissy training

BigTitsLust 1 year ago

Akira Sissifies Jessica (HD MP4)

57% HD 0:26 / 13:00

Akira Sissifies Jessica (HD MP4)

Clips4sale 1 year ago

Kat Fucks Lance in Chastity Part 1 by Sweetfemdom

Kat Fucks Lance in Chastity Part 1 by Sweetfemdom

XHamster 2 years ago

Confess that you are a sissy to your best friend!

Confess that you are a sissy to your best friend!

XHamster 2 months ago

Delivery Guy Becomes a Sissy

54% HD 1:01 / 13:05

Delivery Guy Becomes a Sissy

FapHouse 8 months ago

Stepmommy Turns U into a Little Bunny Sissy Wench - Penny Barber Taboo

Stepmommy Turns U into a Little Bunny Sissy Wench - Penny Barber Taboo

Lesbian8 8 months ago

Office sissy training

Office sissy training

XHamster 8 months ago

Obedient White Whore Worships BBC & Dicked down Hard

Obedient White Whore Worships BBC & Dicked down Hard

FreePorn8 5 years ago

Training You as My Sissy | Femdom Penny Barber Diaper Mistress Feminization POV

Training You as My Sissy | Femdom Penny Barber Diaper Mistress Feminization POV

Fapcat 4 years ago

Cruel Cuckoldress - Her Lover, His Cell Part 2

74% 4K 0:43 / 11:12

Cruel Cuckoldress - Her Lover, His Cell Part 2

Clips4sale 2 years ago

The Chastity Fuck

The Chastity Fuck

XHamster 6 days ago

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

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

Amateur8 2 months ago

Thrashing My Sissybitch

Thrashing My Sissybitch

BigTitsLust 3 days ago

Sissy Whore Gets Ding-penis Experience - Full Version

Sissy Whore Gets Ding-penis Experience - Full Version

PornFreeNow 2 weeks ago

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