Cum In Chastity Videos (7,581)

Who's the Real stepdaddy with Jenny Flowers

61% HD 1:01 / 20:25

Who's the Real stepdaddy with Jenny Flowers

FapHouse 2 months ago

Jessica Bloom Extreme Deep Urethral Sounding in Chastity Then Massive Cumshot And Eats It All

Jessica Bloom Extreme Deep Urethral Sounding in Chastity Then Massive Cumshot And Eats It All

XHamster 4 months ago

Full Version - Extended - Goth Slut Pees in Condom

68% 1:01 / 11:01

Full Version - Extended - Goth Slut Pees in Condom

FapHouse 2 months ago

Pretty Femboy in Chastity Fucked Raw

Pretty Femboy in Chastity Fucked Raw

XHamster 4 months ago

part two of the nun series

part two of the nun series

XHamster 4 days ago

Sissy Slut Fucked Raw Then Swallows Huge Creampie and Her Own Sissygasm

Sissy Slut Fucked Raw Then Swallows Huge Creampie and Her Own Sissygasm

XHamster 3 months ago

Femboy Moans From Getting Railed

Femboy Moans From Getting Railed

XHamster 2 months ago

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79% HD 1:14 / 34:16

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PornBox 1 year ago

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

Chastity Sissygasm Compilation Encouragement - Sissy Jessica Bloom

XHamster 1 year ago

Anal Bash

ShemaleSex 1 week ago

Trans Girls Share a Cock and Chastity Cage Huge Load of Cum Jessica Bloom and JenbyDoll

Trans Girls Share a Cock and Chastity Cage Huge Load of Cum Jessica Bloom and JenbyDoll

XHamster 9 months ago

Pumping my load into a sissy White boi pussy

Pumping my load into a sissy White boi pussy

XHamster 2 weeks ago

Lily Demure: Please Suck on Me

Lily Demure: Please Suck on Me

FapHouse 1 year ago

Caged Cowgirl Gets Titties Pumped & Plowed

71% HD 1:01 / 26:44

Caged Cowgirl Gets Titties Pumped & Plowed

FapHouse 4 months ago

Ts In Chastity Hotel Fuck Cum Inside Pussy

Ts In Chastity Hotel Fuck Cum Inside Pussy

PornoXO 6 days ago

Sissy crossdresser cumming twice and swallowing her own cum

Sissy crossdresser cumming twice and swallowing her own cum

XHamster 3 months ago

negative chastity cum

negative chastity cum

XHamster 3 years ago

Sissy

XHamster 6 months ago

Chastity release

Chastity release

XHamster 1 week ago

Caged Femboy with a Big Dildo in His Ass Cums From a Magic Wand for You

HD 1:01 / 14:03

Caged Femboy with a Big Dildo in His Ass Cums From a Magic Wand for You

FapHouse 2 years ago

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

XHamster 10 months ago

Power Fucking His Ass Till He Cums

Power Fucking His Ass Till He Cums

XHamster 3 months ago

Crossdresser in Chastity Fucked Raw

Crossdresser in Chastity Fucked Raw

XHamster 1 month ago

Sexy TS Kitty Lucia Maya LEAKS CUM in Chastity While FUCKING HER ASS Then Unlocks Cage & CUMS HARD

Sexy TS Kitty Lucia Maya LEAKS CUM in Chastity While FUCKING HER ASS Then Unlocks Cage & CUMS HARD

XHamster 2 years ago

Sudden Ejaculation In Her Fufu Pinch

Sudden Ejaculation In Her Fufu Pinch

TrannyGem 2 years ago

Sissy Slut Ball Busting Jessica Bloom Has Two Plapping Orgsams Back to Back And Eats Her Own Cum!

Sissy Slut Ball Busting Jessica Bloom Has Two Plapping Orgsams Back to Back And Eats Her Own Cum!

XHamster 2 weeks ago

Ts In Chastity Hotel Fuck Cum inside pussy

Ts In Chastity Hotel Fuck Cum inside pussy

Eporner 1 week 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 2 years ago

I fuck my roomie and fills my hole full of cum in chastity

I fuck my roomie and fills my hole full of cum in chastity

GayJaVu 11 months ago

Femboy Piss and Flash Her Hot Feminized Body Outdoor Piss While in Chastity Cage and Rub Her Small Flaccid Cock

56% HD 0:39 / 13:00

Femboy Piss and Flash Her Hot Feminized Body Outdoor Piss While in Chastity Cage and Rub Her Small Flaccid Cock

FapHouse 1 year ago

pigtail trans cutie

55% 0:30 / 26:19

pigtail trans cutie

Clips4sale 1 year ago

Sissy Jessica Bloom Locked & Fucked by BBC Machine - Anal Orgasm, Cum Cleanup + Swallowed

Sissy Jessica Bloom Locked & Fucked by BBC Machine - Anal Orgasm, Cum Cleanup + Swallowed

XHamster 6 months ago

Sedy Ladyboy does a Thousand Ball Plappies while gooning for the BNWO

Sedy Ladyboy does a Thousand Ball Plappies while gooning for the BNWO

XHamster 2 months ago

BBC Fucks a Slutty Crossdresser Without Limits

BBC Fucks a Slutty Crossdresser Without Limits

XHamster 1 year ago

2025.05.24 sport swimsuit cum in chastity

2025.05.24 sport swimsuit cum in chastity

XHamster 8 months ago

Gorgeous femboy fuck till cum a lot

Gorgeous femboy fuck till cum a lot

XHamster 1 year ago

Sissy slave in chastity restrained cumming

Sissy slave in chastity restrained cumming

XHamster 3 years ago

Sissy Rides Cock And Gets Fucked Hard Bareback Doggy Style for Massive Anal Creampie She Licks up Every Drop of Cum

Sissy Rides Cock And Gets Fucked Hard Bareback Doggy Style for Massive Anal Creampie She Licks up Every Drop of Cum

XHamster 2 weeks ago

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

67% HD 0:30 / 58:54

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

Clips4sale 2 years ago

Ts Roberta Cortes and Ts Janny Costa fuck Hotwife Nara in front of his cuck husband (1080p ENG-sub) Trans Woman - Trans Fuck Cis - Trans Blowjob - Trans Cock

HD 0:22 / 21:31

Ts Roberta Cortes and Ts Janny Costa fuck Hotwife Nara in front of his cuck husband (1080p ENG-sub) Trans Woman - Trans Fuck Cis - Trans Blowjob - Trans Cock

Clips4sale 8 months ago

Trans girl is locked up in chastity, but still giving ass - Emily Adaire ts

Trans girl is locked up in chastity, but still giving ass - Emily Adaire ts

XHamster 1 year ago

How To Fit And JIZZ In A FuFu Pin (Step by Step Voice Guide)

How To Fit And JIZZ In A FuFu Pin (Step by Step Voice Guide)

TrannyGem 2 years ago

Impelement Chair Double Agony: Constant Prostate Stimulation + Ruthless Electro Cock Edging

Impelement Chair Double Agony: Constant Prostate Stimulation + Ruthless Electro Cock Edging

XHamster 2 weeks ago

hope you guys like watching me get messy and covered in cum lube💦 nothing better than stret

hope you guys like watching me get messy and covered in cum lube💦 nothing better than stret

AShemaleTube 1 year ago

Chubby alt femboy in stockings got BBC into her ass compilation

Chubby alt femboy in stockings got BBC into her ass compilation

MyLust 1 year ago

Sissy Jessica Bloom Tries Out 5 Different Types of Chastity Cage

Sissy Jessica Bloom Tries Out 5 Different Types of Chastity Cage

XHamster 4 months ago

She Accidentally Shoots A Load Rock Hard In Her Box While Edging

She Accidentally Shoots A Load Rock Hard In Her Box While Edging

TrannyGem 1 year ago

cuties cumming in chastity: a compilation

cuties cumming in chastity: a compilation

AShemaleTube 1 year ago

SisK releases her penis from chastity device and plays with her horny penis after her ass is being plugged.

SisK releases her penis from chastity device and plays with her horny penis after her ass is being plugged.

XHamster 4 years ago

luci belle and justice onlyfans tatted trans gets bbc

luci belle and justice onlyfans tatted trans gets bbc

TransDoe 2 years ago

L@dyc@k3 - Asian Trans 40 cumshot Cumpilation - Compilation

L@dyc@k3 - Asian Trans 40 cumshot Cumpilation - Compilation

Eporner 7 months ago

AB138 Bitch Sissy Cumshot and Edging training (Chinese and English subtitles)

AB138 Bitch Sissy Cumshot and Edging training (Chinese and English subtitles)

XHamster 1 year ago

MaureenNadh - (Day 1 Locked In Chastity) Anal Training Before School

MaureenNadh - (Day 1 Locked In Chastity) Anal Training Before School

XHamster 3 years ago

Chastity Christmas! Naughty tranny girl gets punished! Spanking! Mouthfuck! Assfuck!

Chastity Christmas! Naughty tranny girl gets punished! Spanking! Mouthfuck! Assfuck!

XHamster 7 months ago

Jackie Israeli touching herself

Jackie Israeli touching herself

XHamster 3 years ago

Taniax masturbate in the streets with big black dildo wearing sexy miniskirt

Taniax masturbate in the streets with big black dildo wearing sexy miniskirt

XHamster 1 month ago

Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot

63% HD 0:39 / 5:27

Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot

FapHouse 1 year ago

Plump Redhead Sissy in Chastity Cage and Leather Bodysuit Large Jizz flow after rubbing her Oiled Clitty with BBC Vibrator

Plump Redhead Sissy in Chastity Cage and Leather Bodysuit Large Jizz flow after rubbing her Oiled Clitty with BBC Vibrator

ShemaleSin 1 week ago

Femboy cums in chastity while being fucked hard

Femboy cums in chastity while being fucked hard

AShemaleTube 1 month ago

Skinny Kitty in Cage rides Huge Dildo (12cm diameter)

Skinny Kitty in Cage rides Huge Dildo (12cm diameter)

XHamster 1 week ago

Wifey Taunts you about locking you in innocence like her TRANSSEXUAL Buddy POINT OF VIEW HAND JOB SISSY TEACHING

Wifey Taunts you about locking you in innocence like her TRANSSEXUAL Buddy POINT OF VIEW HAND JOB SISSY TEACHING

TrannyGem 5 years ago

Chastity Fuckdolls Reverse Gangbang

Chastity Fuckdolls Reverse Gangbang

AbTranny 1 year ago

Watch this kinky secretary in lingerie get a hardcore virginity-raiding and cumshot from a vibrator

Watch this kinky secretary in lingerie get a hardcore virginity-raiding and cumshot from a vibrator

TrannyMovs 2 weeks ago

Chastity Sissy Anal Orgasms And Licking Cum of Feet Jessica Bloom and Femdom Polieana

Chastity Sissy Anal Orgasms And Licking Cum of Feet Jessica Bloom and Femdom Polieana

XHamster 2 years ago

Jessica Bloom Extreme Deep Urethral Sounding in Chastity Then Massive Cumshot And Eats It All

Jessica Bloom Extreme Deep Urethral Sounding in Chastity Then Massive Cumshot And Eats It All

ShemaleSex 1 month ago

Who's the Real stepdaddy with Jenny Flowers

55% HD 0:39 / 20:25

Who's the Real stepdaddy with Jenny Flowers

FapHouse 2 months ago

andylynn payne @andylynnpayne transgirl solo wank porn video

andylynn payne @andylynnpayne transgirl solo wank porn video

TransDoe 2 years ago

Sissy Slut Sucks Cock For Huge Load of Cum Twice in a Row - Jessica Bloom

Sissy Slut Sucks Cock For Huge Load of Cum Twice in a Row - Jessica Bloom

XHamster 10 months ago

Sissyboi Femboi Black Lingerie Fishnet Fisting Dildo Play

Sissyboi Femboi Black Lingerie Fishnet Fisting Dildo Play

XHamster 2 years ago

i'm the most excellent horse rider in city-- 40 cm vibrator -- compilation

i'm the most excellent horse rider in city-- 40 cm vibrator -- compilation

ShemaleSin 3 days ago

Dream a Little Dream

Dream a Little Dream

XHamster 1 year ago

Roommate Loses Bet and Gets Locked in Chastity

Roommate Loses Bet and Gets Locked in Chastity

XHamster 5 months ago

I shag my roommate and packs my fuck-hole utter of jizm in innocence

I shag my roommate and packs my fuck-hole utter of jizm in innocence

5Gays 9 months ago

Chastity, piss and cum

Chastity, piss and cum

XHamster 1 week ago

Trans Femdom Jessica Bloom Edges And Milks Her Huge Cock While Humiliating You SPH

Trans Femdom Jessica Bloom Edges And Milks Her Huge Cock While Humiliating You SPH

XHamster 1 year ago

Extreme Combined Torture: Impaled Prostate + Electro Cock Edging on Impalement Chair

Extreme Combined Torture: Impaled Prostate + Electro Cock Edging on Impalement Chair

XHamster 3 weeks ago

Schizu Have Fun In Innocence

Schizu Have Fun In Innocence

TrannyGem 2 years ago

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

XHamster 4 months ago

Sissy Whore Training 2

Sissy Whore Training 2

XHamster 1 year ago

The Condom Looks so Tight on That Big Trans Cock

The Condom Looks so Tight on That Big Trans Cock

XHamster 7 months ago

onlyfans - wollip dont get scared when i pull out my cock on you porn video

onlyfans - wollip dont get scared when i pull out my cock on you porn video

TransDoe 1 year ago

Aiden Ward Fist Jona Ortiz

73% 1:01 / 21:27

Aiden Ward Fist Jona Ortiz

FapHouse 4 months ago

bound shemale slut in chastity anal creampie by bbc

bound shemale slut in chastity anal creampie by bbc

PornOne 4 weeks ago

fansly - mysterioustg and thedongkinger shy sissy in chastity corrupted by first bbc

fansly - mysterioustg and thedongkinger shy sissy in chastity corrupted by first bbc

TransDoe 2 years ago

Inverted Chastity Off, Itty Bitty Clitty Gets Sounded, Pushed Back in & Locked up Again!

Inverted Chastity Off, Itty Bitty Clitty Gets Sounded, Pushed Back in & Locked up Again!

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 9 months ago

2025 Trans Anal & Cum Compilation Pt 1 ABRIDGED

2025 Trans Anal & Cum Compilation Pt 1 ABRIDGED

Amateur8 3 months ago

Jessica Bloom Anal Dildo And Vibrator Chastity Orgasm Then Swallows Her Own Cum!

Jessica Bloom Anal Dildo And Vibrator Chastity Orgasm Then Swallows Her Own Cum!

XHamster 1 month ago

A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!

A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!

XHamster 2 years ago

Jessica Bloom Spit-Roasted & Machine-Fucked! Throbbing Cocks DP Her Holes Massive Facial & Cum Swallow

Jessica Bloom Spit-Roasted & Machine-Fucked! Throbbing Cocks DP Her Holes Massive Facial & Cum Swallow

XHamster 5 months ago

SisK CD in purple EP3 her sissy clity is released from a super tiny chastity cage

SisK CD in purple EP3 her sissy clity is released from a super tiny chastity cage

XHamster 4 years ago

I Can’t Take It Anymore! Locked up but Trying to Cum Anyway

54% HD 0:39 / 17:12

I Can’t Take It Anymore! Locked up but Trying to Cum Anyway

FapHouse 1 year ago

Gagged Nylon Slut Gets Her Face Fucked and Ass Pounded Like a Cheap Cum Dump

70% 1:01 / 7:42

Gagged Nylon Slut Gets Her Face Fucked and Ass Pounded Like a Cheap Cum Dump

FapHouse 3 months ago

Happy Birthday Lola

65% HD 1:01 / 28:52

Happy Birthday Lola

FapHouse 4 months ago

JenbyDoll Sucks Mommy Jessica Bloom's Throbbing Tgirl Cock Then Shares Cummy Kiss

JenbyDoll Sucks Mommy Jessica Bloom's Throbbing Tgirl Cock Then Shares Cummy Kiss

XHamster 1 year ago

Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum

Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum

XHamster 2 years ago

Dirty Talk Lady

Dirty Talk Lady

XHamster 7 months ago

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

XHamster 3 months ago

Sissy Boy Shakes His Cage in Front of Your Face to Cum for You

Sissy Boy Shakes His Cage in Front of Your Face to Cum for You

XHamster 2 weeks ago

Is it Big Enough to be Called a Cock? or Small Enough to be an Itty Bitty Clitty?

Is it Big Enough to be Called a Cock? or Small Enough to be an Itty Bitty Clitty?

XHamster 3 years ago

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

XHamster 5 months ago

Messy Makeup Fuck With Tgirl Harley ABRIDGED

Messy Makeup Fuck With Tgirl Harley ABRIDGED

ShemaleSex 1 month ago

Cute femboy being teased by magic ropes and a chastity cage, cumming hard during the time that locked.

Cute femboy being teased by magic ropes and a chastity cage, cumming hard during the time that locked.

ShemaleSin 10 months ago

Ass to Mouth With Over 100 Loads of CUM! Frozen Cum Play Sissy Jessica Bloom

Ass to Mouth With Over 100 Loads of CUM! Frozen Cum Play Sissy Jessica Bloom

XHamster 10 months ago

Sissy White Boi and His Wife: Strippers for Big Black Daddy - Chapter 1: the Fantasy

58% HD 1:01 / 5:51

Sissy White Boi and His Wife: Strippers for Big Black Daddy - Chapter 1: the Fantasy

FapHouse 2 months ago

Tranny in chastity fucking her ass with dildos

Tranny in chastity fucking her ass with dildos

XHamster 11 months ago

Kymmy receives To batter After ten Days In Virginity At The Sissy Institute!

Kymmy receives To batter After ten Days In Virginity At The Sissy Institute!

TransTube.tv 1 month ago

caged QOS sissy plaps balls & cums with huge BBC in her ass

72% 4K 0:18 / 9:49

caged QOS sissy plaps balls & cums with huge BBC in her ass

Clips4sale 1 year ago

Kylie Maria In Kylie Cums In Her Chastity

Kylie Maria In Kylie Cums In Her Chastity

AbTranny 4 years ago

Nicco & Patric & Santiago Have Amazing Threesome

58% HD 2:00 / 1:04:58

Nicco & Patric & Santiago Have Amazing Threesome

Flirt4Free 2 years ago

Sissy Boy Shakes His Cage in Front of Your Face to Cum for You

Sissy Boy Shakes His Cage in Front of Your Face to Cum for You

XHamster 2 weeks ago

Anal Beads, Buttplug and Huge Dildo - Anal Training Cumslut Jessica Bloom

Anal Beads, Buttplug and Huge Dildo - Anal Training Cumslut Jessica Bloom

XHamster 1 year ago

Cute Blonde Transgirls fucks herself with extra large pink dildo!!

Cute Blonde Transgirls fucks herself with extra large pink dildo!!

XHamster 2 months ago

Pink Sissy Bride Dildo Play and Tombussy Chastity Cumming

Pink Sissy Bride Dildo Play and Tombussy Chastity Cumming

XHamster 2 weeks ago

Eating, fucking, and breeding a bad sissy's pussy

Eating, fucking, and breeding a bad sissy's pussy

XHamster 1 month ago

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 9

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 9

XHamster 6 months ago

Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot

64% HD 1:01 / 5:27

Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot

FapHouse 1 year ago

wollip getting railed by my boyfriend pov onlyfans video

wollip getting railed by my boyfriend pov onlyfans video

TransDoe 3 years ago

2025 Trans Anal & Cum Compilation Pt 1 ABRIDGED

2025 Trans Anal & Cum Compilation Pt 1 ABRIDGED

ShemaleSin 5 months ago

Sissy Maid Gets Locked in Chastity and Strained to Serve1

Sissy Maid Gets Locked in Chastity and Strained to Serve1

FapHouse 1 week ago

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