Chastity Compilation Videos (1,083)

Goth Femboy Nun Compilation - Huge Cumshot in Chastity

57% HD 0:39 / 2:30

Goth Femboy Nun Compilation - Huge Cumshot in Chastity

FapHouse 10 months ago

HUGE BBC fucks & breeds kinky brunette shemale

HUGE BBC fucks & breeds kinky brunette shemale

aShemaleTube 1 month ago

Sissy Hero - PMV by HoloPMV

Sissy Hero - PMV by HoloPMV

aShemaleTube 6 months ago

Caged Cowgirls

aShemaleTube 4 months 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

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

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 Shelby Kiss's New Year's Resolutions for 2026

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

xHamster 1 week ago

Femboy POV Banging Compilation

Femboy POV Banging Compilation

FreePorn8 3 weeks ago

BNWO Sissy Bride Gooning

BNWO Sissy Bride Gooning

xHamster 3 months ago

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 5

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 5

aShemaleTube 1 week ago

Fisting Double Sissygasm Cumshots

Fisting Double Sissygasm Cumshots

xHamster 5 months ago

Fucking Trans Woman in Chastity - Compilation 7

Fucking Trans Woman in Chastity - Compilation 7

xHamster 3 weeks ago

Best of Harmony Rose vol 1

Best of Harmony Rose vol 1

xHamster 9 months ago

Fag slave humiliation compilation part 8

Fag slave humiliation compilation part 8

xHamster 1 week ago

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

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

aShemaleTube 4 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 Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

xHamster 1 year ago

crossdresser domination bdsm

crossdresser domination bdsm

BDSMDoe 1 year ago

Caged Sissy Cums with Inverted Chastity Still On

Caged Sissy Cums with Inverted Chastity Still On

xHamster 2 weeks ago

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

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

TrannyGem 11 months ago

ASSFUCK ejaculation compilation two

ASSFUCK ejaculation compilation two

TrannyGem 2 years ago

Sissy - Feminization - Sissy Trainer - Sissification

Sissy - Feminization - Sissy Trainer - Sissification

TrannyGem 3 years ago

Chastity Caged Sissies

Chastity Caged Sissies

aShemaleTube 11 months 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

FemdomRAW: The Hottest Dominant Bitches

FemdomRAW: The Hottest Dominant Bitches

Eporner 9 months ago

Aline Fucks Sissy's Ass

HD 1:01 / 16:48

Aline Fucks Sissy's Ass

FapHouse 1 day ago

Bisex ladies in 3some fucked in cumshot compilation video

Bisex ladies in 3some fucked in cumshot compilation video

Some.Porn 1 year ago

Finger in the Ass While Masturbating with a Condom

Finger in the Ass While Masturbating with a Condom

xHamster 2 weeks 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

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

Bl@ckate BBC lover

Bl@ckate BBC lover

Eporner 10 months ago

Sissy Evolution 2: Be Happy. Be a Bimbo

Sissy Evolution 2: Be Happy. Be a Bimbo

xHamster 2 months ago

Tgirl cums twice

Tgirl cums twice

xHamster 3 years ago

Getting Pummeled Until I'm Bellowing!! Camshow Compilation

Getting Pummeled Until I'm Bellowing!! Camshow Compilation

TrannyGem 1 year ago

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

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

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

Trans Sissy Whore disciplined by Mistresse Murmur compilation

Trans Sissy Whore disciplined by Mistresse Murmur compilation

ShemaleSin 4 weeks ago

onlyfans - ava venom @theavavenom transgirl hot fuck scene

onlyfans - ava venom @theavavenom transgirl hot fuck scene

TransDoe 1 year ago

acceptance letter

acceptance letter

TrannyGem 5 years ago

Chastity Compilation: Trans and Sissy Girls Locked and Fucked

Chastity Compilation: Trans and Sissy Girls Locked and Fucked

KeekAss 3 years ago

Cumming in chastity compilation

Cumming in chastity compilation

aShemaleTube 5 months ago

Sissy Candy's Dildo Post Compilation!

Sissy Candy's Dildo Post Compilation!

xHamster 1 year 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

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

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

Raine Ryder - Femboy and Huge Dildos COMPILATION

Raine Ryder - Femboy and Huge Dildos COMPILATION

xHamster 4 weeks ago

Sissy sub pegging compilation

Sissy sub pegging compilation

Juicexxx 2 weeks ago

Maskedloki BBC breed trans sissies (Compilation)

Maskedloki BBC breed trans sissies (Compilation)

xHamster 1 year ago

Feminization Sissication Sissy instructing - Glad Idiot - Innocence Jizz

Feminization Sissication Sissy instructing - Glad Idiot - Innocence Jizz

TrannyGem 6 months ago

Ruin Your Pitiful Pouch

Ruin Your Pitiful Pouch

TrannyGem 1 year 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

katie fox ts compilation cum 2024 pt 1

katie fox ts compilation cum 2024 pt 1

PornBox 1 year 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

Best femdom pegging porn compilation

Best femdom pegging porn compilation

AnySex 2 years ago

POV Cuckold vol 11

POV Cuckold vol 11

xHamster 8 months ago

Sissy Chastity Maid Service Training With Ria Bentley

Sissy Chastity Maid Service Training With Ria Bentley

xHamster 2 months ago

Purity Box Challange - Day two/ten

Purity Box Challange - Day two/ten

Gayhub 5 months ago

2025 Sissy Compilation

2025 Sissy Compilation

xHamster 9 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

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

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

Chastity Sissy Deepthroat Practice &ndash_ Oral Handjob Combo

Chastity Sissy Deepthroat Practice &ndash_ Oral Handjob Combo

XVideos 1 month 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 2 months ago

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 3 weeks ago

POV Cuckold vol 23

POV Cuckold vol 23

xHamster 3 months 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

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

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

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

BBC & Blondes Compilation # 2

BBC & Blondes Compilation # 2

aShemaleTube 3 weeks ago

chastity cum and squirt and cum again

chastity cum and squirt and cum again

xHamster 3 months 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

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

Tiny clitty compilation

Tiny clitty compilation

xHamster 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

Endless cumshots during anal with hot trannies - Shemale CUMpilation

Endless cumshots during anal with hot trannies - Shemale CUMpilation

XGroovy 2 years ago

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Virginity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

TrannyGem 1 year ago

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

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

xHamster 6 months ago

quick vid

xHamster 1 year ago

Pop-Shot Compilation

Pop-Shot Compilation

4Gay 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

Premature Handsfree Sissygasm - Jizz shot in 30 Seconds!

Premature Handsfree Sissygasm - Jizz shot in 30 Seconds!

Gayhub 1 month ago

Best of Femdom Pegging! Strapon and Cum Compilation.

Best of Femdom Pegging! Strapon and Cum Compilation.

Pornzona 1 month ago

some sissy fun

xHamster 1 year ago

My Freak Tonight - PMV by HoloPMV

My Freak Tonight - PMV by HoloPMV

aShemaleTube 3 weeks ago

Femboy POV Screwing Compilation

Femboy POV Screwing Compilation

Dafreeporn 3 weeks 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

Sissy Mara Jade's FULL Sissygasm Chastity Compilation!

Sissy Mara Jade's FULL Sissygasm Chastity Compilation!

ShemaleSin 4 years ago

Fuck Machine

xHamster 4 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

JessieBbwSissy - Plapgasm Compilation

JessieBbwSissy - Plapgasm Compilation

xHamster 3 weeks ago

Chastity Compilation Trans and Sissy Girls Locked and Fucked

Chastity Compilation Trans and Sissy Girls Locked and Fucked

TrannyGem 3 years ago

Pony jizz-shotgun sissygasm compilation

Pony jizz-shotgun sissygasm compilation

TrannyGem 1 year ago

Trans Sissy Whore tutored by Mastix Murmur compilation

Trans Sissy Whore tutored by Mastix Murmur compilation

Amateur8 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

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

CROSSDRESSER COMPILATION Sissy Story SISSY TRANSFORMATION Feminization

CROSSDRESSER COMPILATION Sissy Story SISSY TRANSFORMATION Feminization

SortPorn 4 years ago

sissygasm caged Compilation

sissygasm caged Compilation

xHamster 3 years 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

Biggest Spunk fountain Femboy - Chastity Cage Jizz flow Explosion

Biggest Spunk fountain Femboy - Chastity Cage Jizz flow Explosion

ShemaleSin 1 month ago

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

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

FreePorn8 1 year ago

Chastity locked riding bbc on slaves face then and peg their ass for cum

Chastity locked riding bbc on slaves face then and peg their ass for cum

Pornzona 1 week ago

Maskedloki BBC breed trans femboys and sissy (Compilation)

Maskedloki BBC breed trans femboys and sissy (Compilation)

Tranny.one 1 year ago

Die gefesselte Sissy in der Abstellkammer | ASMR Hörspiel | Fufu Clip, Anal, Dildo, Femdom, Keusch

Die gefesselte Sissy in der Abstellkammer | ASMR Hörspiel | Fufu Clip, Anal, Dildo, Femdom, Keusch

Juicexxx 1 month ago

Shake It Off - PMV by HoloPMV

Shake It Off - PMV by HoloPMV

aShemaleTube 1 year ago

Sissy Compilation Outside drinking and pussy fuck in Public

Sissy Compilation Outside drinking and pussy fuck in Public

XVideos 5 months ago

1 2 3 4 5

1,083 results found

Related searches

Narrow your search

chastity lynn compilation

Categories Pornstars

Categories Pornstars

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

Pornmd.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 Pornmd.com. All rights reserved.