Chastity Compilation Videos (1,078)

My Sissy Cums Again From the Huge BBC Oh, This Feels Amazing! I Hope You Can Do This Yourself?

57% HD 0:39 / 2:28

My Sissy Cums Again From the Huge BBC Oh, This Feels Amazing! I Hope You Can Do This Yourself?

FapHouse 2 weeks ago

Simply Delicious - I Want This Cock in Me Right Now 2

Simply Delicious - I Want This Cock in Me Right Now 2

FapHouse 3 weeks ago

Goth Femboy Nun Compilation - Huge Cumshot in Chastity

53% HD 0:39 / 2:30

Goth Femboy Nun Compilation - Huge Cumshot in Chastity

FapHouse 9 months ago

HUGE BBC fucks & breeds kinky brunette shemale

HUGE BBC fucks & breeds kinky brunette shemale

aShemaleTube 1 month ago

Caged Sissy Cums with Inverted Chastity Still On

Caged Sissy Cums with Inverted Chastity Still On

xHamster 1 week ago

Caged Cowgirls

aShemaleTube 4 months ago

Cumming on My Face

51% 1:01 / 11:29

Cumming on My Face

FapHouse 1 month ago

Caged ladies cumming

Caged ladies cumming

aShemaleTube 11 months ago

Sissy sub pegging compilation

Sissy sub pegging compilation

Juicexxx 1 week ago

Sissy Shelby Kiss's New Year's Resolutions for 2026

Sissy Shelby Kiss's New Year's Resolutions for 2026

xHamster 5 days ago

Fisting Double Sissygasm Cumshots

Fisting Double Sissygasm Cumshots

xHamster 5 months ago

Femboy POV Banging Compilation

Femboy POV Banging Compilation

FreePorn8 3 weeks ago

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 5

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 5

aShemaleTube 6 days ago

Best of Harmony Rose vol 1

Best of Harmony Rose vol 1

xHamster 9 months ago

Femboy POV Screwing Compilation

Femboy POV Screwing Compilation

Dafreeporn 3 weeks ago

Sissy Hero - PMV by HoloPMV

Sissy Hero - PMV by HoloPMV

aShemaleTube 5 months ago

Fucking Trans Woman in Chastity - Compilation 7

Fucking Trans Woman in Chastity - Compilation 7

xHamster 2 weeks ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

xHamster 1 year ago

艾香艾草 aicao01 getting caught masturbat public and she still doesn't care!

艾香艾草 aicao01 getting caught masturbat public and she still doesn't care!

aShemaleTube 2 years ago

Purity Box Challange - Day two/ten

Purity Box Challange - Day two/ten

Gayhub 5 months ago

Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot

Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot

xHamster 5 months ago

chastity cum and squirt and cum again

chastity cum and squirt and cum again

xHamster 3 months ago

Sissy Evolution 2: Be Happy. Be a Bimbo

Sissy Evolution 2: Be Happy. Be a Bimbo

xHamster 2 months ago

crossdresser domination bdsm

crossdresser domination bdsm

BDSMDoe 1 year ago

Chastity Caged Sissies

Chastity Caged Sissies

aShemaleTube 11 months ago

Bisex ladies in 3some fucked in cumshot compilation video

Bisex ladies in 3some fucked in cumshot compilation video

Some.Porn 1 year ago

ASSFUCK ejaculation compilation two

ASSFUCK ejaculation compilation two

TrannyGem 2 years ago

Femboy Virginity Ejaculation Compilation (palms free-for-all)

Femboy Virginity Ejaculation Compilation (palms free-for-all)

TrannyGem 11 months ago

Sissy Candy's Dildo Post Compilation!

Sissy Candy's Dildo Post Compilation!

xHamster 1 year ago

Trans Sissy Whore disciplined by Mistresse Murmur compilation

Trans Sissy Whore disciplined by Mistresse Murmur compilation

ShemaleSin 3 weeks ago

Rachael Belle Exposed Chastity Sissy Slut Humiliation 1-6 Compilation

Rachael Belle Exposed Chastity Sissy Slut Humiliation 1-6 Compilation

aShemaleTube 6 months ago

Rachael Belle - Fuck Machine Instructions In Both Black and White Stockings

Rachael Belle - Fuck Machine Instructions In Both Black and White Stockings

aShemaleTube 1 year ago

Finger in the Ass While Masturbating with a Condom

Finger in the Ass While Masturbating with a Condom

xHamster 1 week ago

Fuck Your Body - PMV by HoloPMV

Fuck Your Body - PMV by HoloPMV

aShemaleTube 2 months ago

cuties cumming in chastity: a compilation

cuties cumming in chastity: a compilation

aShemaleTube 11 months ago

Take His Chastity

Take His Chastity

Transvids.tv 1 year ago

Bl@ckate BBC lover

Bl@ckate BBC lover

Eporner 10 months ago

Pantieboy tucked and taped in lingerie riding BBC dildo. Hands free cum several times

Pantieboy tucked and taped in lingerie riding BBC dildo. Hands free cum several times

xHamster 1 month ago

Cunilingus and analingus on the beach. My husband is a sissy.

Cunilingus and analingus on the beach. My husband is a sissy.

xHamster 8 months ago

TS f@yef@yeb@by & BBC Split screen Compilation

TS f@yef@yeb@by & BBC Split screen Compilation

aShemaleTube 4 months ago

acceptance letter

acceptance letter

TrannyGem 5 years ago

FEMOUT XXX - Compilation Updates 17th to 21st Nov'25

FEMOUT XXX - Compilation Updates 17th to 21st Nov'25

xHamster 1 month ago

Chastity Compilation: Trans and Sissy Girls Locked and Fucked

Chastity Compilation: Trans and Sissy Girls Locked and Fucked

KeekAss 3 years ago

DEVILS TGIRLS - Sexy Busty Trans Gracie Jane Fucks Hot Teen Masseuse

DEVILS TGIRLS - Sexy Busty Trans Gracie Jane Fucks Hot Teen Masseuse

Some.Porn 4 months ago

Cumming in chastity compilation

Cumming in chastity compilation

aShemaleTube 5 months ago

sissy slut solo riding compilation - MercurySissy best solo anal rides so far

sissy slut solo riding compilation - MercurySissy best solo anal rides so far

Pornzona 2 weeks ago

Raine Ryder - Femboy and Huge Dildos COMPILATION

Raine Ryder - Femboy and Huge Dildos COMPILATION

xHamster 3 weeks ago

Chubby alt femboy in stockings got BBC into her ass compilation

Chubby alt femboy in stockings got BBC into her ass compilation

MyLust 9 months ago

Plump Trans Female Mitts Free-For-All Ass Fucking Ejaculation Jism Shot Compilation

Plump Trans Female Mitts Free-For-All Ass Fucking Ejaculation Jism Shot Compilation

TrannyGem 1 year ago

Maskedloki9 BBC destroying trans femboys and sissies Compilation

Maskedloki9 BBC destroying trans femboys and sissies Compilation

SortPorn 6 months ago

Getting Pummeled Until I'm Bellowing!! Camshow Compilation

Getting Pummeled Until I'm Bellowing!! Camshow Compilation

TrannyGem 1 year ago

Ruin Your Pitiful Pouch

Ruin Your Pitiful Pouch

TrannyGem 1 year ago

katie fox ts compilation cum 2024 pt 1

katie fox ts compilation cum 2024 pt 1

PornBox 1 year ago

No Better Place for a Sissy to Cum then Her Own Mouth! Yum!

No Better Place for a Sissy to Cum then Her Own Mouth! Yum!

xHamster 1 month ago

Best femdom pegging porn compilation

Best femdom pegging porn compilation

AnySex 2 years ago

POV Cuckold vol 11

POV Cuckold vol 11

xHamster 7 months ago

Transformed husband into a slut and four more cocks and two dominatrixes

Transformed husband into a slut and four more cocks and two dominatrixes

xHamster 1 year ago

The Condom Looks so Tight on That Big Trans Cock

69% HD 1:01 / 1:03:50

The Condom Looks so Tight on That Big Trans Cock

FapHouse 5 months ago

Thug BBC breeds lascivious British femboy trap compilation- Maskedloki9 x Nunicult

Thug BBC breeds lascivious British femboy trap compilation- Maskedloki9 x Nunicult

ShemaleSin 1 year ago

No Better Place for a Sissy to Cum then Her Own Mouth! Yum! Clip 1

No Better Place for a Sissy to Cum then Her Own Mouth! Yum! Clip 1

xHamster 1 month ago

Maskedloki BBC breed trans sissies (Compilation)

Maskedloki BBC breed trans sissies (Compilation)

xHamster 1 year ago

Thug BIG BLACK COCK breeds whorish Brit femboy trap compilation- Maskedloki9 x Nunicult

Thug BIG BLACK COCK breeds whorish Brit femboy trap compilation- Maskedloki9 x Nunicult

TrannyGem 1 year ago

2025 Sissy Compilation

2025 Sissy Compilation

xHamster 8 months ago

Home Pegging Cumming Sluts

Home Pegging Cumming Sluts

xHamster 1 month ago

TGirl in Chastiy has Anal Orgasm Sissygasm🏳️&zwj;⚧️

TGirl in Chastiy has Anal Orgasm Sissygasm🏳️&zwj;⚧️

xHamster 4 months ago

Widely Opened Brown Sphincter Internal Cumshot from uber-cute ladyboy

Widely Opened Brown Sphincter Internal Cumshot from uber-cute ladyboy

TrannyGem 3 months ago

Bnwo Sissy

53% HD 0:39 / 2:19

FapHouse 10 months ago

Amazing soft tiny clit sissygasm

Amazing soft tiny clit sissygasm

xHamster 1 month ago

It's so Delicious to Suck and Ride a Big Black Cock Part1

55% HD 1:01 / 7:33

It's so Delicious to Suck and Ride a Big Black Cock Part1

FapHouse 1 month ago

Fucking Sexy Sissy in Chastity - Compilation 5

57% HD 0:08 / 0:40

Fucking Sexy Sissy in Chastity - Compilation 5

FapHouse 4 weeks ago

Lots of cum, throat, dildo and fucking. This got it all. Best of 22

Lots of cum, throat, dildo and fucking. This got it all. Best of 22

xHamster 3 years ago

POV Cuckold vol 23

POV Cuckold vol 23

xHamster 3 months ago

Fuck Machine

xHamster 4 months ago

Fag slave humiliation compilation part 8

Fag slave humiliation compilation part 8

xHamster 5 days ago

Premature Orgasm Cheating - Bf Became Femboy and Cums Hard in Chastity Cell Watching Us

Premature Orgasm Cheating - Bf Became Femboy and Cums Hard in Chastity Cell Watching Us

KAMS 5 months ago

Fucking Trans Woman in Chastity - Compilation 11

Fucking Trans Woman in Chastity - Compilation 11

xHamster 3 months ago

quick vid

xHamster 1 year ago

Slut Cums Into her Own Mouth, Multiple Sissygasms, While Sounding, Vibrator on Her Chastity Cage, In the Woods, Etc!

Slut Cums Into her Own Mouth, Multiple Sissygasms, While Sounding, Vibrator on Her Chastity Cage, In the Woods, Etc!

xHamster 1 year ago

Feminized femboy pissing in toilet while caged like a girl

Feminized femboy pissing in toilet while caged like a girl

xHamster 1 year ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

ShemaleSin 1 year ago

Caged Sissy Slut rides Dildo and Sissygasm using a Vibrator - Locktober Chastity Special

Caged Sissy Slut rides Dildo and Sissygasm using a Vibrator - Locktober Chastity Special

xHamster 1 year ago

Sissy slave

xHamster 1 year ago

Chastity Compilation Trans and Sissy Girls Locked and Fucked

Chastity Compilation Trans and Sissy Girls Locked and Fucked

TrannyGem 3 years ago

Locked Clit cum

Locked Clit cum

xHamster 2 years ago

Sub Cums Between valentinarosa89 and I - Mistress and Shemale Double Top a Sub Slut

Sub Cums Between valentinarosa89 and I - Mistress and Shemale Double Top a Sub Slut

xHamster 1 year ago

Tiny clitty compilation

Tiny clitty compilation

xHamster 1 year ago

Pretty trans dame spunks alot COMPILATION

Pretty trans dame spunks alot COMPILATION

TransTube.tv 1 year ago

To take my chastity in an deserted health center, we were caught

To take my chastity in an deserted health center, we were caught

4Gay 1 month ago

Female Mask Crossdressing Doll Models Her Recent Outfits

Female Mask Crossdressing Doll Models Her Recent Outfits

ShemaleSin 1 year ago

Public Pee Drinking And Chastity Unlocking

Public Pee Drinking And Chastity Unlocking

xHamster 2 years ago

Endless cumshots during anal with hot trannies - Shemale CUMpilation

Endless cumshots during anal with hot trannies - Shemale CUMpilation

XGroovy 2 years ago

Chastity Cage Sissygasm - Huge Spunk fountain (Shorties)

Chastity Cage Sissygasm - Huge Spunk fountain (Shorties)

ShemaleSin 3 months ago

CUMpilation: V-Card Sissygasms, Demolished Ejaculations, & Crossdressing Popshots of a Desperate Sissy

CUMpilation: V-Card Sissygasms, Demolished Ejaculations, & Crossdressing Popshots of a Desperate Sissy

TrannyGem 3 years ago

Riding Dildo in the Park at Night

Riding Dildo in the Park at Night

FapHouse 3 months ago

Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - full video on LayneLovee Manyvids

Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - full video on LayneLovee Manyvids

xHamster 1 year ago

Best of Femdom Pegging! Strapon and Cum Compilation.

Best of Femdom Pegging! Strapon and Cum Compilation.

Pornzona 4 weeks ago

Premature Handsfree Sissygasm - Jizz shot in 30 Seconds!

Premature Handsfree Sissygasm - Jizz shot in 30 Seconds!

Gayhub 4 weeks ago

JessieBbwSissy - Plapgasm Compilation

JessieBbwSissy - Plapgasm Compilation

xHamster 3 weeks ago

some sissy fun

xHamster 1 year ago

My Freak Tonight - PMV by HoloPMV

My Freak Tonight - PMV by HoloPMV

aShemaleTube 3 weeks ago

HandsFree Cumpilation #22

HandsFree Cumpilation #22

BallsAndBoobs 1 year ago

Tgirl cums twice

Tgirl cums twice

xHamster 3 years ago

Pony jizz-shotgun sissygasm compilation

Pony jizz-shotgun sissygasm compilation

TrannyGem 1 year ago

Sissy Mara Jade's FULL Sissygasm Chastity Compilation!

Sissy Mara Jade's FULL Sissygasm Chastity Compilation!

ShemaleSin 4 years ago

Caged and Leaking Chastity Sissy Compilation

Caged and Leaking Chastity Sissy Compilation

BigTitsLust 1 month ago

Latina TS Taniax gets sissygasm on the streets

Latina TS Taniax gets sissygasm on the streets

xHamster 3 weeks ago

Trans Sissy Whore tutored by Mastix Murmur compilation

Trans Sissy Whore tutored by Mastix Murmur compilation

Amateur8 3 weeks ago

Best of Sissies Cumming in Chastity

Best of Sissies Cumming in Chastity

BeMyHole 5 years ago

Sissy Mara Jades UTTER Sissygasm Purity Compilation!

Sissy Mara Jades UTTER Sissygasm Purity Compilation!

TrannyGem 3 years ago

BBC & Blondes Compilation # 2

BBC & Blondes Compilation # 2

aShemaleTube 3 weeks ago

Sissy - Feminization - Sissy Trainer - Sissification

Sissy - Feminization - Sissy Trainer - Sissification

TrannyGem 3 years ago

BNWO Sissy Bride Gooning

BNWO Sissy Bride Gooning

xHamster 3 months ago

Milky TGirl in Chastity has Handsfree Sissygasm + Shows her Lactating Tits

Milky TGirl in Chastity has Handsfree Sissygasm + Shows her Lactating Tits

xHamster 5 months ago

Femboy Restrain bondage - Ruined Cum shot In Chastity Cell

Femboy Restrain bondage - Ruined Cum shot In Chastity Cell

WebcamBros 3 weeks ago

Trans Girl Kitty Clip / Fufu Compilation 2

Trans Girl Kitty Clip / Fufu Compilation 2

aShemaleTube 1 month ago

Femboy Chastity Ball-busting Tutorial: How to Lock Your Penis for BNWO

Femboy Chastity Ball-busting Tutorial: How to Lock Your Penis for BNWO

xHamster 2 years ago

Maskedloki BBC breed trans femboys and sissy (Compilation)

Maskedloki BBC breed trans femboys and sissy (Compilation)

ShemaleSin 1 year ago

Twin Game

xHamster 1 year ago

Femboy Love

HentaiGem 4 months ago

Chastity trans compilation

Chastity trans compilation

Eporner 6 months ago

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