Sissy Training (28,711)

Pretty sissy in pink, pegged for my pleasure

Pretty sissy in pink, pegged for my pleasure

xHamster 1 week ago

BISEXUAL BIMBOFICATION - Encouraged Bi Slut Training Transformation

46% HD 0:10 / 15:41

BISEXUAL BIMBOFICATION - Encouraged Bi Slut Training Transformation

LoyalFans 10 months ago

Strapon love with blonde Dominatrix

Strapon love with blonde Dominatrix

xHamster 1 year ago

Husband dressed up like a sissy bitch & pegged in his tight ass hole

Husband dressed up like a sissy bitch & pegged in his tight ass hole

xHamster 2 years ago

30 days MTF complete transformation - Faggot training - Crossdressing - Bimbofication - Femdom pov - Sissy slut - blonde - Mistress

60% HD 0:10 / 9:57

30 days MTF complete transformation - Faggot training - Crossdressing - Bimbofication - Femdom pov - Sissy slut - blonde - Mistress

LoyalFans 9 months ago

Putting the sissy in chastity by Matriarch Ezada , Evil Woman and me

61% HD 0:10 / 10:32

Putting the sissy in chastity by Matriarch Ezada , Evil Woman and me

LoyalFans 1 year ago

Our New Toy - Part 5 - Cumming Inside Him

HD 0:10 / 20:50

Our New Toy - Part 5 - Cumming Inside Him

LoyalFans 3 years ago

Breaking Her Sissy Doll Part 2/4: Sissy Slut gets her Pussy 🤜 & Sucks Cock with Mistress Stellina Obscura

Breaking Her Sissy Doll Part 2/4: Sissy Slut gets her Pussy 🤜 & Sucks Cock with Mistress Stellina Obscura

LoyalFans 7 months ago

AB003 The trans abbykitty trained by latex Mistress Coronadoll - 极品AV伪娘女优被乳胶衣女王调教

AB003 The trans abbykitty trained by latex Mistress Coronadoll - 极品AV伪娘女优被乳胶衣女王调教

aShemaleTube 6 years ago

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

Husband sissified, bent over and made to spread his ass cheeks for mistress's big cock to pound his tight boi pussy

xHamster 2 years ago

Matriarch Ezada Sinn, Mistress Kennya and Evil Woman train the sissy to take cock up the arse

69% HD 0:10 / 9:53

Matriarch Ezada Sinn, Mistress Kennya and Evil Woman train the sissy to take cock up the arse

LoyalFans 1 year ago

Why I Love Sissification

HD 0:10 / 12:02

Why I Love Sissification

LoyalFans 2 years ago

MommyDomme's Sissy Lesbian Daughter 4K

4K 0:10 / 41:38

MommyDomme's Sissy Lesbian Daughter 4K

LoyalFans 2 years ago

Mistress Sophia Sahara Bi Training

50% 0:26 / 17:03

Mistress Sophia Sahara Bi Training

Clips4sale 3 years ago

Muscle heterosexual man rails BIG BLACK COCK faux-cock in college doll mini-skirt and gets larger salami palms free-for-all

Muscle heterosexual man rails BIG BLACK COCK faux-cock in college doll mini-skirt and gets larger salami palms free-for-all

Gay4Porn 4 years ago

Beta Male Cuckold Is Humiliated And Turned Into A Sissy Maid (1080p)

HD 0:30 / 22:22

Beta Male Cuckold Is Humiliated And Turned Into A Sissy Maid (1080p)

Clips4sale 1 month ago

Boot Slut Worships My Boots

Boot Slut Worships My Boots

Clips4sale 4 months ago

Miss Whitney Morgan's Closet Slave's Vacation

HD 0:10 / 11:55

Miss Whitney Morgan's Closet Slave's Vacation

LoyalFans 1 year ago

FROM DOG TO BITCH

HD 0:10 / 17:20

FROM DOG TO BITCH

LoyalFans 3 months ago

SISSY PRISON - Dental Terror

66% 4K 0:35 / 19:17

SISSY PRISON - Dental Terror

Clips4sale 3 months ago

Accept The Household Humiliation

Accept The Household Humiliation

LoyalFans 1 year ago

Jessica Bloom Takes Fist And Foot Up Her Slutty Asshole Until She Cums Anal Fisting And Footing

Jessica Bloom Takes Fist And Foot Up Her Slutty Asshole Until She Cums Anal Fisting And Footing

xHamster 1 year ago

Sounds and Ballcrushing CBT on Latex Sissy

61% HD 0:10 / 26:25

Sounds and Ballcrushing CBT on Latex Sissy

LoyalFans 3 years ago

Lesbian Sissy

59% HD 0:10 / 9:43

LoyalFans 2 years ago

Gefangener feminisiert von Mistress Susi (deutsch) Prisoner feminized by Mistress Susi WMV

70% 0:11 / 10:30

Gefangener feminisiert von Mistress Susi (deutsch) Prisoner feminized by Mistress Susi WMV

Clips4sale 3 years ago

Cute Sissy Gets Ruined

HD 0:10 / 11:10

Cute Sissy Gets Ruined

LoyalFans 2 weeks ago

Sissy training and Discipline

60% HD 0:10 / 9:12

Sissy training and Discipline

LoyalFans 1 year ago

Sissy Slave Contract

HD 0:10 / 12:37

Sissy Slave Contract

LoyalFans 3 years ago

Sissy Husband Double BBC Training (FULL): Humiliating Wedgies, Panties, Spankings, Double Anal Pegging & **** with Mistress Stellina Obscura

60% HD 0:10 / 41:20

Sissy Husband Double BBC Training (FULL): Humiliating Wedgies, Panties, Spankings, Double Anal Pegging & **** with Mistress Stellina Obscura

LoyalFans 9 months ago

Sissy trainer: become slut like her

Sissy trainer: become slut like her

xHamster 4 years ago

Lara Croft Anal Tomb Raider #1 - Jessica Bloom Fisting & Anal Stretching

Lara Croft Anal Tomb Raider #1 - Jessica Bloom Fisting & Anal Stretching

xHamster 11 months ago

Step-Mommy’s Secret Sissy Part 2/3: Sissy Slut in Chastity gets Pegged with HUGE COCK - Mistress Stellina Obscura

HD 0:10 / 13:27

Step-Mommy’s Secret Sissy Part 2/3: Sissy Slut in Chastity gets Pegged with HUGE COCK - Mistress Stellina Obscura

LoyalFans 7 months ago

Be a Sissy for AI

51% HD 0:10 / 4:10

Be a Sissy for AI

LoyalFans 1 year ago

suruba taurus rio de janeiro

65% HD 0:30 / 15:58

suruba taurus rio de janeiro

PornBox 2 years ago

Foot worship and ball torment with shoe! (on SALE)!!

65% HD 0:29 / 18:56

Foot worship and ball torment with shoe! (on SALE)!!

Clips4sale 1 year ago

Foot Worship Feminization

Foot Worship Feminization

LoyalFans 2 months ago

Hardcore Anal Fist Training

Hardcore Anal Fist Training

aShemaleTube 3 days ago

Cumslut Training Jessica Bloom Self Suck & Cumplay CEI Cum Eating Instructions

Cumslut Training Jessica Bloom Self Suck & Cumplay CEI Cum Eating Instructions

xHamster 4 years ago

Jacky Joy hot wife Cuckold creampie POV femdom facesitting creampie eating sissy big tits sph findom chastity strapon sex 883

Jacky Joy hot wife Cuckold creampie POV femdom facesitting creampie eating sissy big tits sph findom chastity strapon sex 883

Clips4sale 5 months ago

Sissy Husband BBC Training Part 3/3: Femdom Sissy Fucking with Double BBC Pegging & Anal **** with Stellina Obscura

HD 0:10 / 10:43

Sissy Husband BBC Training Part 3/3: Femdom Sissy Fucking with Double BBC Pegging & Anal **** with Stellina Obscura

LoyalFans 9 months ago

Kitchen Chores Humiliation for Sissy Maid (1080p)

HD 0:19 / 13:44

Kitchen Chores Humiliation for Sissy Maid (1080p)

Clips4sale 1 week ago

Sissy Boy Mind Fuck 30 Minutes

HD 0:10 / 35:21

Sissy Boy Mind Fuck 30 Minutes

LoyalFans 3 weeks ago

Full doggy anal training

Full doggy anal training

LoyalFans 3 weeks ago

DOMINATRIX CHRONICALS -Barcelona-

50% HD 0:10 / 1:30:28

DOMINATRIX CHRONICALS -Barcelona-

LoyalFans 7 months ago

Sissy Slut Spit Roast Practice – Pegging Anal Training JOI Feminization Masturbation Instructions by Goddess Nikki Kit

63% HD 0:10 / 10:14

Sissy Slut Spit Roast Practice – Pegging Anal Training JOI Feminization Masturbation Instructions by Goddess Nikki Kit

LoyalFans 1 week ago

The Making Of A Sissy Part 2

HD 0:10 / 11:56

The Making Of A Sissy Part 2

LoyalFans 2 years ago

Broken into a Sissy - Strap-on, Cock Worship, Goddess Worship 720p wmv

HD 0:20 / 10:31

Broken into a Sissy - Strap-on, Cock Worship, Goddess Worship 720p wmv

Clips4sale 3 weeks ago

You're Nothing. But You're Comfortable Trampling Femdom Teaser

You're Nothing. But You're Comfortable Trampling Femdom Teaser

xHamster 9 months ago

From man to sissy, a full feminisation transformation, the full journey from male to female, undergoing makeup application to make her pretty for the cocks she's going to service! (HD)

53% 4K 0:20 / 20:02

From man to sissy, a full feminisation transformation, the full journey from male to female, undergoing makeup application to make her pretty for the cocks she's going to service! (HD)

Clips4sale 2 years ago

Mistress pegs her bitch bois ass for a custom fan video

Mistress pegs her bitch bois ass for a custom fan video

xHamster 2 years ago

Pegging Latex Fuckhole

65% HD 0:10 / 25:53

Pegging Latex Fuckhole

LoyalFans 3 years ago

FEMDOM SISSY PEGGING ANAL CUM EATING BIG TITS STRAPON CUMSHOT

FEMDOM SISSY PEGGING ANAL CUM EATING BIG TITS STRAPON CUMSHOT

xHamster 2 weeks ago

Kinky Bitch - Twin Domination 7

4K 0:31 / 13:12

Kinky Bitch - Twin Domination 7

Clips4sale 4 months ago

Sissy-Keuschlings KG-Entwicklungsstufen

Sissy-Keuschlings KG-Entwicklungsstufen

LoyalFans 10 months ago

Turning you into my sissy slut

65% 4K 0:30 / 11:29

Turning you into my sissy slut

Clips4sale 4 years ago

Tv Isabella's Compilation Y-Training Scheme

Tv Isabella's Compilation Y-Training Scheme

aShemaleTube 4 months ago

Slut Display & Destroy – Latex Sissy Clinic [1080]

4K 0:38 / 20:45

Slut Display & Destroy – Latex Sissy Clinic [1080]

Clips4sale 9 months ago

Sissy Training - Sissygasm Encouragement Jessica Bloom

Sissy Training - Sissygasm Encouragement Jessica Bloom

xHamster 4 years ago

Training Gimp Part 3: Total Sensory Overload

66% HD 0:10 / 13:35

Training Gimp Part 3: Total Sensory Overload

LoyalFans 3 weeks ago

Sissy Cuck Bitch Boy: Cum Tax

HD 0:10 / 18:31

Sissy Cuck Bitch Boy: Cum Tax

LoyalFans 4 years ago

Suck Cock For Me

HD 0:10 / 18:42

Suck Cock For Me

LoyalFans 4 weeks ago

Sissy Must Upgrade to BBC

61% HD 0:10 / 6:24

Sissy Must Upgrade to BBC

LoyalFans 3 years ago

Breaking Her Sissy Doll Part 3/4: Sissy Slut Humiliation, Deep Throat Training & Femdom Pegging with Mistress Stellina Obscura

HD 0:10 / 20:43

Breaking Her Sissy Doll Part 3/4: Sissy Slut Humiliation, Deep Throat Training & Femdom Pegging with Mistress Stellina Obscura

LoyalFans 7 months ago

POV Sissy transformatie

Premium 4K 10:55

POV Sissy transformatie

Clips4sale 1 year ago

Sissy Locktober 2023 - Everything You Need to Know

HD 0:10 / 14:17

Sissy Locktober 2023 - Everything You Need to Know

LoyalFans 2 years ago

Public piss and sissy training

Public piss and sissy training

xHamster 3 years ago

how to make a bisexual cuckold out of a husband chastity belt! only anal fuck!

69% HD 0:30 / 18:18

how to make a bisexual cuckold out of a husband chastity belt! only anal fuck!

PornBox 3 years ago

My sissy bitch's greedy boipussy swallows my 12inch BBC her clitcock has never looked so more tiny and pathetic

My sissy bitch's greedy boipussy swallows my 12inch BBC her clitcock has never looked so more tiny and pathetic

xHamster 8 months ago

Sissified husband gets his ass fucked & humiliated

Sissified husband gets his ass fucked & humiliated

xHamster 1 year ago

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

55% 4K 0:19 / 10:39

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

Clips4sale 2 months ago

Double Dom slut training vol1 FHD

60% HD 0:10 / 12:17

Double Dom slut training vol1 FHD

LoyalFans 10 months ago

ULTIMATE SISSY DIAPER SLUT TRAINING for step-Daddy Dick

50% HD 0:10 / 34:12

ULTIMATE SISSY DIAPER SLUT TRAINING for step-Daddy Dick

LoyalFans 1 month ago

FAGGOT OBSESSION

FAGGOT OBSESSION

LoyalFans 2 years ago

Feminized slut Blaire_18 sniffs and licks her Mistress's armpits. Femdom Christmas, armpit fetish, feminization, sissy

Feminized slut Blaire_18 sniffs and licks her Mistress's armpits. Femdom Christmas, armpit fetish, feminization, sissy

xHamster 2 months ago

FINANCIAL DOMINATION

HD 0:10 / 10:11

FINANCIAL DOMINATION

Clips4sale 2 weeks ago

Sissy Hure Training, including to swallow sperm (german) - Sissy Huren Ausbildung Incl Sperma schlucken (deutsch) 4K

50% 4K 0:11 / 13:17

Sissy Hure Training, including to swallow sperm (german) - Sissy Huren Ausbildung Incl Sperma schlucken (deutsch) 4K

Clips4sale 3 years ago

Sharing Wife With Friend Sucking Dick In Car In Public

Sharing Wife With Friend Sucking Dick In Car In Public

xHamster 4 years ago

Wife pegs & dominated husband

Wife pegs & dominated husband

xHamster 6 months ago

Sissy Maid Tormented in Chastity

Sissy Maid Tormented in Chastity

LoyalFans 2 years ago

slim shemale do her daily fitness program and cum

slim shemale do her daily fitness program and cum

xHamster 3 years ago

SISSYGASM ENCOURAGEMENT

66% HD 0:10 / 7:26

SISSYGASM ENCOURAGEMENT

LoyalFans 1 year ago

Faggot Triggers

Faggot Triggers

Clips4sale 1 year ago

Femdom teasers compilation part 1 gabby_19 Gabby Lust

Femdom teasers compilation part 1 gabby_19 Gabby Lust

xHamster 2 years ago

TELL HER

62% HD 0:10 / 17:53

LoyalFans 2 years ago

5 must-have sex toys for sissies - Femdom sissy feminization

63% HD 0:10 / 15:34

5 must-have sex toys for sissies - Femdom sissy feminization

LoyalFans 2 months ago

Tu deviendras une Sissy Cocue

56% HD 0:29 / 28:59

Tu deviendras une Sissy Cocue

Clips4sale 2 years ago

Mistress Mercer Reminds me Why She's the StepDaddy

62% HD 0:10 / 6:24

Mistress Mercer Reminds me Why She's the StepDaddy

LoyalFans 1 month ago

New Sissy Maid - part 2 - Miss Jessica Wood is following and observing her new sissy maid who is tidying for her Sissy Training

63% HD 0:10 / 3:56

New Sissy Maid - part 2 - Miss Jessica Wood is following and observing her new sissy maid who is tidying for her Sissy Training

LoyalFans 1 week ago

Day 2 of 7: Bimbo Bootcamp-Pretty Princess Protocol

Day 2 of 7: Bimbo Bootcamp-Pretty Princess Protocol

LoyalFans 1 week ago

GIVE IN TO THE GAY 720P

45% HD 0:10 / 8:01

GIVE IN TO THE GAY 720P

LoyalFans 1 year ago

STEP-MOMMY TURNS YOU OUT FOR BBC

46% HD 0:10 / 12:22

STEP-MOMMY TURNS YOU OUT FOR BBC

LoyalFans 2 years ago

Sissy Spitroast Training - Stretching My Ass While I Gag on Your Cock FULL VIDEO ON LAYNELOVEE MANYVIDS

Sissy Spitroast Training - Stretching My Ass While I Gag on Your Cock FULL VIDEO ON LAYNELOVEE MANYVIDS

xHamster 2 years ago

the feminized bitch in stockings wants to cum in his panties. sissy in the chastity belt.

63% HD 0:30 / 15:32

the feminized bitch in stockings wants to cum in his panties. sissy in the chastity belt.

PornBox 3 years ago

Be A Good Slut

LoyalFans 2 years ago

Sissy Training: Sitting Pretty

Sissy Training: Sitting Pretty

LoyalFans 2 years ago

Cuck Clean Up

HD 0:10 / 10:23

LoyalFans 3 years ago

Its all about the lemon slice

Its all about the lemon slice

LoyalFans 3 years ago

Make me bi in chastity for your husband bbc please fuck my ass Queen

64% 0:30 / 19:37

Make me bi in chastity for your husband bbc please fuck my ass Queen

Clips4sale 9 months ago

Why I Use a Shock Collar on My Slave

Why I Use a Shock Collar on My Slave

LoyalFans 4 months ago

BBC dildo ass fuck for HOT slut Tiffany Kitten

BBC dildo ass fuck for HOT slut Tiffany Kitten

xHamster 3 months ago

Mistress Niki Jerk Off Her Huge Strapon Until Cum on Your Big Cock (MOV)

Mistress Niki Jerk Off Her Huge Strapon Until Cum on Your Big Cock (MOV)

Clips4sale 1 month ago

Turning You into My Sissy Princess - Tia Black trains you to suck cock, get fucked in the ass, and be the feminine Sissy Princess you are meant to be

Turning You into My Sissy Princess - Tia Black trains you to suck cock, get fucked in the ass, and be the feminine Sissy Princess you are meant to be

Clips4sale 5 days ago

Sissies Suck Dick: Slave Training Task

Sissies Suck Dick: Slave Training Task

LoyalFans 5 months ago

Bf gets drilled in rump by trans gf, go after Daniela Chanel! My OF is free-for-all!

Bf gets drilled in rump by trans gf, go after Daniela Chanel! My OF is free-for-all!

Transvids.tv 7 months ago

korean Bloomer femboy threeway (total flick on fansly)

korean Bloomer femboy threeway (total flick on fansly)

4Gay 2 months ago

Caged Femboy kitty gets used by Vicky and Indica

61% HD 0:10 / 8:46

Caged Femboy kitty gets used by Vicky and Indica

LoyalFans 5 months ago

Who's Fucking Who? - StrapOn

52% 0:32 / 10:05

Who's Fucking Who? - StrapOn

Clips4sale 1 year ago

Sissy Barbie’s Slutty JOI: From Doll to Cock Toy JOI

HD 0:10 / 14:14

Sissy Barbie’s Slutty JOI: From Doll to Cock Toy JOI

LoyalFans 4 months ago

Sissy Monica & Slavena FIRST SISSY TRAINING

HD 0:10 / 14:50

Sissy Monica & Slavena FIRST SISSY TRAINING

LoyalFans 4 months ago

Kinky Stepmom in nylon Stockings Seduces Chaste stepson Dilon - Stepmother in Silk Japan Robe Masturbates hairy Pussy, Rubbing his Cock on Shoe High Heels, small Feet on Big Dick, Female Domination, Cum on Feet, Sensual Domination 4k

61% 4K 0:25 / 16:22

Kinky Stepmom in nylon Stockings Seduces Chaste stepson Dilon - Stepmother in Silk Japan Robe Masturbates hairy Pussy, Rubbing his Cock on Shoe High Heels, small Feet on Big Dick, Female Domination, Cum on Feet, Sensual Domination 4k

Clips4sale 4 months ago

Sissy boi gets his cock & balls pulled whilst his ass being pounded

Sissy boi gets his cock & balls pulled whilst his ass being pounded

xHamster 1 year ago

Sissy boi dressed up and pegged like the dirty cock whore slut he is!

Sissy boi dressed up and pegged like the dirty cock whore slut he is!

xHamster 2 years ago

Trucker step-Daddy Loves Diaper Sissy

HD 0:20 / 27:40

Trucker step-Daddy Loves Diaper Sissy

Clips4sale 4 months ago

Humiliated with Ugly Panties: Extended Cut

HD 0:10 / 12:49

Humiliated with Ugly Panties: Extended Cut

LoyalFans 2 years ago

Sissy Step 2

61% HD 0:10 / 10:54

LoyalFans 1 year ago

Sissy finishing school, Alice’s Final Preparation. The full movie

62% HD 0:10 / 54:42

Sissy finishing school, Alice’s Final Preparation. The full movie

LoyalFans 6 months ago

FROM ALPHA TO BARBIE BIMBO

HD 0:10 / 13:06

FROM ALPHA TO BARBIE BIMBO

LoyalFans 1 year ago

Sissy Maid Counseling

Sissy Maid Counseling

LoyalFans 1 year ago

Dual Deep Throat Training

Dual Deep Throat Training

LoyalFans 3 years ago

Blowjob-Training For Our Sissy Girl Part 1 – Lady Selina Morgan

48% HD 0:10 / 6:33

Blowjob-Training For Our Sissy Girl Part 1 – Lady Selina Morgan

LoyalFans 3 months ago

1 2 3 4 5

28,711 results found

Related searches

Narrow your search

sissy anal training

Models

Models

Legal

Terms of Service Privacy Statement Statement of Responsibility Notice and Action Policy (Link Removal) DMCA / Copyright Acceptable Content Policy Digital Services Act 2257

Parents

Modelgalore.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Modelgalore.com. All rights reserved.