19 years old Anal Ladyboy Gets Cock
10 years ago
6:14

aShemaleTube

19 years old Anal Ladyboy Gets Cock

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Lover with big cock fucks painful small tits shemale
14 years ago
4:59

aShemaleTube

Lover with big cock fucks painful small tits shemale

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Ladyboy Pink Painful Bareback
8 years ago
6:19

aShemaleTube

Ladyboy Pink Painful Bareback

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Stacy's masochistic pleasure session with Luna's wet pussy
53 days ago
8:14

VideoSection

Stacy's masochistic pleasure session with Luna's wet pussy

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Teen guy cumsucker gets fucked painful by big ebony tranny
14 years ago
19:07

aShemaleTube

Teen guy cumsucker gets fucked painful by big ebony tranny

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Three way, hermaphrodite
38 days ago
5:08

VideoSection

Three way, hermaphrodite

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Dude Takes A Painful Shemale Ass Fucking
8 years ago
21:05

Txxx

Dude Takes A Painful Shemale Ass Fucking

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Busty transsexual gives straight guy some painful delight
11 years ago
5:29

aShemaleTube

Busty transsexual gives straight guy some painful delight

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Oops, It's A Little Bit Painful For Him
10 years ago
3:00

FlyFlv

Oops, It's A Little Bit Painful For Him

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Ladyboy Pang Jerking Off
9 years ago
6:25

aShemaleTube

Ladyboy Pang Jerking Off

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Bitchy shemale gives her man a real pain
11 years ago
7:00

AnyPorn

Bitchy shemale gives her man a real pain

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Shemale with leather cloth likes cruel sex with pain in her apartment
9 years ago
19:49

xHamster

Shemale with leather cloth likes cruel sex with pain in her apartment

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Ladyboy Pang Jerking Off
9 years ago
5:32

BravoTube

Ladyboy Pang Jerking Off

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Transgender Bitch Electro TizORTURE Pain Slut
9 years ago
8:24

TnaFlix

Transgender Bitch Electro TizORTURE Pain Slut

Tags: bdsm, bitch, bondage, pain, slut, transsexual

Chains, Pain and Pleasure
9 years ago
3:24

TubeDupe

Chains, Pain and Pleasure

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Teen Ladyboy Pang Jerking Off
9 years ago
5:32

aShemaleTube

Teen Ladyboy Pang Jerking Off

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Master interrogates submissive with intense pummeling and raunchy oral play
1 year ago
5:17

VideoSection

Master interrogates submissive with intense pummeling and raunchy oral play

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Blairglass Sensual Massage Feat. Stacy Sadistic
3 years ago
30:54

ShemaleZ

Blairglass Sensual Massage Feat. Stacy Sadistic

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BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
2 months ago
7:34

xHamster

BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales

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Public slut gets her ass and mouth drilled in kinky outdoor action
3 months ago
5:23

ShemaleMovie

Public slut gets her ass and mouth drilled in kinky outdoor action

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Pornstars: ashlynn leigh, james deen, princess donna

Bbc Shemale fucks boy and cum inside ass
8 days ago
17:57

aShemaleTube

Bbc Shemale fucks boy and cum inside ass

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Futuretist Compilation of Hot Sadistic Sluts Intense Orgy with Burst Asses and Thirsty for Cum Intense Pleasure
4 months ago
6:12

xHamster

Futuretist Compilation of Hot Sadistic Sluts Intense Orgy with Burst Asses and Thirsty for Cum Intense Pleasure

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Leather-clad dominatrix humiliates submissive cockslut outdoors
4 months ago
5:19

VideoSection

Leather-clad dominatrix humiliates submissive cockslut outdoors

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Busty milf dominatrix punishes man with cane for kinky fun
4 months ago
5:20

ShemaleMovie

Busty milf dominatrix punishes man with cane for kinky fun

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Pornstars: aiden starr, maitresse madeline

It's What You Really Ache For - Fagboy
23 days ago
7:02

aShemaleTube

It's What You Really Ache For - Fagboy

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The tormentor's painful and raunchy discipline is not forgiven even if you sob and pray for it
6 months ago
12:31

KeekAss

The tormentor's painful and raunchy discipline is not forgiven even if you sob and pray for it

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Compilation with Weekly Episodes from the pain whore Alina
7 months ago
2:05

xHamster

Compilation with Weekly Episodes from the pain whore Alina

Tags: anal, bdsm, beauty, big ass, compilation, croatian, crossdressing, femboy, feminization, fetish

Steamy quickie with ladyboy Pang
2 months ago
5:06

AnalDin

Steamy quickie with ladyboy Pang

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Public outdoor FFM anal penetration with strapon in various languages
3 months ago
5:17

ShemaleMovie

Public outdoor FFM anal penetration with strapon in various languages

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tony punishing his slave male nipples naked
4 months ago
5:00

KeekAss

tony punishing his slave male nipples naked

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Kinkysmut, gagging
5 days ago
5:28

VideoSection

Kinkysmut, gagging

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Pang1 - 4min Clip
4 months ago
3:59

XXXDan

Pang1 - 4min Clip

Tags: big cock, big tits, facial, pain, sucking, thai

Big-breasted furry dominatrix anally pounds submissive man
4 months ago
5:21

ShemaleMovie

Big-breasted furry dominatrix anally pounds submissive man

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Pornstars: cherry torn

JUDE LYNX — SPANKS, MONSTER FAUX-COCK AND PUNY GIMP
6 months ago
8:20

KeekAss

JUDE LYNX — SPANKS, MONSTER FAUX-COCK AND PUNY GIMP

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Pain loving solo TS in lingerie toys her cock while wanking
7 months ago
5:00

PornGem

Pain loving solo TS in lingerie toys her cock while wanking

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Kinky iris with new spike clamps, very painfull first time
8 months ago
6:52

XXXDan

Kinky iris with new spike clamps, very painfull first time

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Pain and pleasure, chastity and lust,  Part 1
2 months ago
51:35

XXXDan

Pain and pleasure, chastity and lust, Part 1

Tags: anal, bdsm, beauty, german, mature, pain

Executive dominated by professional mistress Lorelei Lee
3 months ago
5:20

ShemaleMovie

Executive dominated by professional mistress Lorelei Lee

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Pornstars: lorelei lee

Candle Wax dripped on Sissy's cunt sheclit
32 days ago
2:13

xHamster

Candle Wax dripped on Sissy's cunt sheclit

Tags: american, bdsm, big ass, cunt, domination, european, fetish, fishnet, hd, high heels

Slender lesbian enjoys anal plug and deep drilling session
3 months ago
5:22

ShemaleMovie

Slender lesbian enjoys anal plug and deep drilling session

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Pornstars: haley wilde

tony punishing his slave male nipples naked 2
4 months ago
0:21

KeekAss

tony punishing his slave male nipples naked 2

Tags: bdsm, clamp, crossdressing, gay, hd, nipples, nude, pain, punishment, slave

Liinssarah fucks boytoy hard and cum inside ass
8 days ago
26:03

aShemaleTube

Liinssarah fucks boytoy hard and cum inside ass

Tags: ass, cum, hardcore, missionary, moaning, pain, transsexual

Cuckold Husband Gets Hard Painful Fucking From His Wifes Bull Lover Hard Humiliation Cd Sissy Cuck
59 days ago
12:45

HClips

Cuckold Husband Gets Hard Painful Fucking From His Wifes Bull Lover Hard Humiliation Cd Sissy Cuck

Tags: amateur, anal, assfucking, cuckold, deep throat, hardcore, hd, humiliation, husband, pain

Pang1 - Doggiestyle - 4min Clip
4 months ago
4:04

XXXDan

Pang1 - Doggiestyle - 4min Clip

Tags: big ass, big cock, big tits, blowjob, cumshot, doggystyle, facial, pain, panties, shaved

Female dominatrix Mona Wales spanks and anally penetrates submissive male
5 months ago
5:19

ShemaleMovie

Female dominatrix Mona Wales spanks and anally penetrates submissive male

Tags: anal, bdsm, bizarre, bondage, dildo, dominatrix, pain, spanking, strap-on, submissive

T-girl Pang Fapping Off
6 months ago
6:26

KeekAss

T-girl Pang Fapping Off

Tags: asian, big tits, brunette, handjob, hd, jerking, ladyboy, masturbation, pain, solo

T-girl enjoys sucking and riding ass
7 months ago
5:17

ShemaleMovie

T-girl enjoys sucking and riding ass

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stacy sadomasochistic climax denial utter on crimson
17 days ago
5:45

KeekAss

stacy sadomasochistic climax denial utter on crimson

Tags: amateur, ass, bbw, crossdressing, denial, fat, fetish, glasses, orgasm, pain

Shemale with insatiable hard-on craves cock ride and begs for more
8 months ago
5:19

HDSex

Shemale with insatiable hard-on craves cock ride and begs for more

Tags: anal, ass, big ass, big cock, cumshot, dick, first time, ladyboy, massage, oral

feet worship while fucked
2 months ago
2:14

aShemaleTube

feet worship while fucked

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Extreme submission and female authority in BDSM scene featuring Maitresse Madeline
3 months ago
5:19

ShemaleMovie

Extreme submission and female authority in BDSM scene featuring Maitresse Madeline

Tags: bdsm, bizarre, bondage, dildo, domination, extreme, gagging, hardcore, pain, pornstar

Pornstars: maitresse madeline

Busty Trans Scientist Needs Her Hole Filled By Her Partner - Stacy Sadistic And Kellie Shaw
3 months ago
8:06

ShemaleZ

Busty Trans Scientist Needs Her Hole Filled By Her Partner - Stacy Sadistic And Kellie Shaw

Tags: american, anal, assfucking, barebacking, big tits, blonde, cumshot, deep throat, hd, hooters

Sissy Trans Hazel Splashes Her Nads in the Woods!
4 months ago
6:12

KeekAss

Sissy Trans Hazel Splashes Her Nads in the Woods!

Tags: amateur, ball busting, caught, crossdressing, dare, forest, hd, humiliation, pain, public

Rollenspiel, marionette
4 months ago
10:29

ShemaleMovie

Rollenspiel, marionette

Tags: bdsm, domination, german, latex, pain, pissing, skinny, slave, teen (18+)

stacy sadomasochistic smacks wild kitten^utter on crimson^
5 months ago
7:00

KeekAss

stacy sadomasochistic smacks wild kitten^utter on crimson^

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The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
6 months ago
10:53

xHamster

The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded

Tags: abuse, anal, assfucking, barebacking, bdsm, beauty, blowjob, creampie, cum, domination

Finishing up with pain on my balls
7 months ago
4:02

xHamster

Finishing up with pain on my balls

Tags: balls, bdsm, dutch, european, hd, latex, mature, pain, redhead, sissy

Hard-anal, anal-destruction
8 months ago
5:12

ShemaleMovie

Hard-anal, anal-destruction

Tags: anal, ass, big ass, big cock, blowjob, gaping hole, ladyboy, pain, sucking, teen (18+)

Pain and Pleasure
2 months ago
51:35

JizzBunker

Pain and Pleasure

Tags: amateur, anal, bdsm, blowjob, german, hardcore, mature, pain, toys

Tranny with big cock fucks latino man in the ass
3 months ago
35:40

xHamster

Tranny with big cock fucks latino man in the ass

Tags: anal, ass, barebacking, bathroom, beauty, big cock, big tits, couple, creampie, german

Redhead asian trans all covered in pain ass fucked
12 days ago
7:30

xHamster

Redhead asian trans all covered in pain ass fucked

Tags: amateur, anal, asian, assfucking, barebacking, blowjob, couple, cum, cumshot, hd

Kellie Shaw And Stacy Sadistic In Trans Archaeologists Discover Bareback Sex At The Temple
3 months ago
8:06

ShemaleZ

Kellie Shaw And Stacy Sadistic In Trans Archaeologists Discover Bareback Sex At The Temple

Tags: anal, assfucking, barebacking, big ass, big tits, blonde, booty, booty shake, deep throat, hd

Wealthy entrepreneur dominated and pegged by a fierce female dominatrix
4 months ago
5:20

ShemaleMovie

Wealthy entrepreneur dominated and pegged by a fierce female dominatrix

Tags: anal, bdsm, bizarre, bondage, dildo, domination, dominatrix, gagging, pain, pornstar

Pornstars: lorelei lee

Taunting, edging my stud pleasure button
4 months ago
9:20

KeekAss

Taunting, edging my stud pleasure button

Tags: amateur, boy, clamp, clit, denial, dick, hd, masturbation, pain, pussy

Futuretist Compilation of Hot Sadistic Sluts Intense Orgy with Burst Asses and Thirsty for Cum Intense Pleasure
5 months ago
3:18

xHamster

Futuretist Compilation of Hot Sadistic Sluts Intense Orgy with Burst Asses and Thirsty for Cum Intense Pleasure

Tags: amateur, american, asian, ass, bbw, beauty, big cock, black, compilation, crossdressing

tony performing his pain pervert punishment to his nipples
6 months ago
3:14

KeekAss

tony performing his pain pervert punishment to his nipples

Tags: bdsm, bisexual, clamp, crossdressing, fetish, gay, nipples, pain, punishment, submissive

Painful Anal In The Office
8 months ago
5:16

ShemaleZ

Painful Anal In The Office

Tags: anal, big cock, big tits, hd, office, pain

mistress stacy instructs kitten all about suck jobs! utter version on crimson
14 days ago
6:28

KeekAss

mistress stacy instructs kitten all about suck jobs! utter version on crimson

Tags: bbw, bdsm, big cock, blowjob, dick, femdom, hd, mistress, mom, oral

WELTS WHORE GET PAIN
2 months ago
0:30

aShemaleTube

WELTS WHORE GET PAIN

Tags: domination, hd, lingerie, pain, slut

Stacy Sadistic Has Her Way with Wet Pussy
2 months ago
8:12

xHamster

Stacy Sadistic Has Her Way with Wet Pussy

Tags: beauty, big tits, blonde, blowjob, cum, hd, ladyboy, lingerie, pain, pussy

Shemale takes cock in mouth
3 months ago
5:17

ShemaleMovie

Shemale takes cock in mouth

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Unexpected shemale
3 months ago
5:10

HDSex

Unexpected shemale

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Muscular Trans beauties ditch protection after hitting the gym
4 months ago
11:44

ShemaleMovie

Muscular Trans beauties ditch protection after hitting the gym

Tags: ass, beauty, big ass, big cock, big tits, blowjob, gym, muscled, pain, teen (18+)

Intense pleasure, pain play & submission
4 months ago
15:36

ShemaleMovie

Intense pleasure, pain play & submission

Tags: american, bdsm, bondage, masturbation, orgasm, pain, solo

So hard and painful fuck the big dick (watch sweet video on faphouse, fabclub,)
5 months ago
5:07

xHamster

So hard and painful fuck the big dick (watch sweet video on faphouse, fabclub,)

Tags: 3some, big cock, big tits, dick, fingering, gloryhole, hardcore, hd, hermaphrodite, pain

Painful Assfuck With Huge Knob
17 days ago
6:27

ShemaleZ

Painful Assfuck With Huge Knob

Tags: anal, asian, assfucking, big ass, blowjob, booty, booty shake, hd, ladyboy, oriental

116 min degrading of bdsm sissy pain whore Alina
7 months ago
2:20

xHamster

116 min degrading of bdsm sissy pain whore Alina

Tags: anal toying, bdsm, beauty, big ass, compilation, croatian, crossdressing, cumshot, femboy, feminization

Pain loving TS masturbates in closeup with toy in urethra
7 months ago
5:00

XXXDan

Pain loving TS masturbates in closeup with toy in urethra

Tags: bdsm, close up, lingerie, masturbation, pain, small tits, solo, toys, transsexual, urethra

Transvestite from hell
31 days ago
11:12

xHamster

Transvestite from hell

Tags: bdsm, bondage, crossdressing, femdom, pain, punishment, queen, slave, spanking, transvestite

Free-anal-videos, anal-video
9 months ago
5:18

VideoSection

Free-anal-videos, anal-video

Tags: anal, ass, big ass, blowjob, gaping hole, huge cock, ladyboy, pain, pov

Adult movie star, sissys
2 months ago
8:02

VideoSection

Adult movie star, sissys

Tags: anal, bdsm, blowjob, brutal, crossdressing, dildo, fisting, gaping hole, german, hardcore

Atm, porn-vido
3 months ago
5:17

ShemaleMovie

Atm, porn-vido

Tags: anal, ass, ass to mouth, big ass, big cock, blowjob, ladyboy, pain, sucking

Ladyboy painful assfuck with huge knob
41 days ago
6:27

AnalDin

Ladyboy painful assfuck with huge knob

Tags: anal, asian, ass, assfucking, barebacking, big cock, blowjob, ladyboy, pain, pov

Waaa-431 Sweet And Sadistic Shemale Gal Nurse! Reverse Anal Fuck Penis Injection Clinic Leading To Super Crazy Dry Orgasm Ramu Ichinose
4 months ago
2:00:58

ShemaleZ

Waaa-431 Sweet And Sadistic Shemale Gal Nurse! Reverse Anal Fuck Penis Injection Clinic Leading To Super Crazy Dry Orgasm Ramu Ichinose

Tags: anal, asian, assfucking, blonde, blowjob, clinic, crazy, deep throat, dick, japanese

Pang1 - Trailer
4 months ago
1:56

XXXDan

Pang1 - Trailer

Tags: big cock, big tits, facial, pain, sucking, thai

Inked slave tied up and fucked by a dominant woman
4 months ago
5:18

ShemaleMovie

Inked slave tied up and fucked by a dominant woman

Tags: bdsm, bizarre, bondage, brutal, dildo, domination, gagging, hardcore, pain, pornstar

Pornstars: lorelei lee

Hot quickie with ladyboy Pang
5 months ago
5:06

aShemaleTube

Hot quickie with ladyboy Pang

Tags: amateur, anal, asian, assfucking, blowjob, dick, hd, homevideo, ladyboy, pain

Sexy Asian Big Cock Shemale likes to fuck and give pain to big Ass Porn Star Magic Michel deep anal
46 days ago
10:05

xHamster

Sexy Asian Big Cock Shemale likes to fuck and give pain to big Ass Porn Star Magic Michel deep anal

Tags: anal, asian, barebacking, beauty, big ass, big cock, big tits, cum, domination, hd

A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
7 months ago
1:34

xHamster

A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass

Tags: anal, ass, barebacking, bdsm, beauty, big ass, blowjob, desperate, femboy, feminization

Ladyboy painful anal with huge dick
7 months ago
6:27

aShemaleTube

Ladyboy painful anal with huge dick

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Big-dicks, rough-anal-sex
3 months ago
5:16

ShemaleMovie

Big-dicks, rough-anal-sex

Tags: anal, ass, big ass, big cock, blowjob, brutal, dick, gaping hole, ladyboy, pain

some fun kitty playtime
4 months ago
16:17

xHamster

some fun kitty playtime

Tags: amateur, american, anal, anal toying, bdsm, fetish, fisting, funny, gaping hole, hardcore

Rachell dominates her new sex toy Valentina in extreme threesome play
4 months ago
5:10

VideoSection

Rachell dominates her new sex toy Valentina in extreme threesome play

Tags: 3some, bdsm, big cock, deep throat, extreme, group sex, humiliation, latina, pain, spanking

Busty mummy domme jerking gimp slave in harsh femdom session
4 months ago
5:19

ShemaleMovie

Busty mummy domme jerking gimp slave in harsh femdom session

Tags: bdsm, big tits, bizarre, bondage, brutal, dildo, domination, femdom, gagging, jerking

Pornstars: maitresse madeline

Hi t-girl - Spectacular transgender princess with large faux bumpers
6 months ago
13:32

KeekAss

Hi t-girl - Spectacular transgender princess with large faux bumpers

Tags: anal, asian, big ass, blowjob, brunette, crying, cum, cumshot, fake tits, hardcore

Trans man experiences nipple orgasm and moans in pleasure
7 months ago
5:56

ShemaleMovie

Trans man experiences nipple orgasm and moans in pleasure

Tags: american, bdsm, cum, femboy, jizz, masturbation, moaning, nipples, orgasm, pain

Ladyboy122 video
8 months ago
1:32

xHamster

Ladyboy122 video

Tags: anal, anal toying, dick, fitness, hd, homevideo, ladyboy, muscled, pain, skinny

Rayray Sugarbutt puts her cock and balls inside her bitch's asshole
9 months ago
4:11

aShemaleTube

Rayray Sugarbutt puts her cock and balls inside her bitch's asshole

Tags: anal, ass, balls, dick, pain

Pain loving tranny masturbates close up with a toy in the urethra
7 months ago
5:00

XXXDan

Pain loving tranny masturbates close up with a toy in the urethra

Tags: bdsm, close up, lingerie, masturbation, pain, small tits, solo, toys, tranny, urethra

Kinky iris very painful lifting 4,2 kilo on nipples
8 months ago
9:44

JizzBunker

Kinky iris very painful lifting 4,2 kilo on nipples

Tags: kinky, nipples, pain

Ladyboys in pain, beautiful anal fuck, the best
9 months ago
5:14

HDSex

Ladyboys in pain, beautiful anal fuck, the best

Tags: anal, ass, beauty, big ass, big cock, blowjob, brutal, ladyboy, pain, pov

Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
2 months ago
13:12

xHamster

Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune

Tags: amateur, american, anal, bbw, big ass, big cock, blowjob, crossdressing, cuckold, femboy

Anal, freeporm
10 months ago
5:17

ShemaleMovie

Anal, freeporm

Tags: anal, ass, beauty, big ass, blowjob, dildo, ladyboy, oral, pain, pov

Sexy ladyboy vixen smokes while getting her ass ravaged
10 months ago
5:18

VideoSection

Sexy ladyboy vixen smokes while getting her ass ravaged

Tags: anal, ass, big ass, big cock, huge cock, ladyboy, pain, ravage, vixen

Shemale Pang Gets Herself Off
9 months ago
5:00

XXXDan

Shemale Pang Gets Herself Off

Tags: pain

Sultry shemale craves cum and expertly sucks and rides cock for a load of jizz
9 months ago
5:17

VideoSection

Sultry shemale craves cum and expertly sucks and rides cock for a load of jizz

Tags: anal, ass, big ass, big cock, blowjob, cum, cumshot, dick, huge cock, jizz

Olly Jackson, female-to-male, dominated by sadistic Sean Taylor in intense anal pounding
1 year ago
9:45

ShemaleMovie

Olly Jackson, female-to-male, dominated by sadistic Sean Taylor in intense anal pounding

Tags: anal, bdsm, bondage, bound, cumshot, domination, pain

Stretch Nipples with special tool , VERY PAINFULL !!
9 months ago
8:34

JizzBunker

Stretch Nipples with special tool , VERY PAINFULL !!

Tags: bdsm, lingerie, mature, nipples, pain, pov, small tits, solo

Rebeccas painful Orgasm
9 months ago
10:49

JizzBunker

Rebeccas painful Orgasm

Tags: orgasm, pain

Pain loving solo TS jerks her cock with toy in her urethra
9 months ago
5:00

XXXDan

Pain loving solo TS jerks her cock with toy in her urethra

Tags: bdsm, big cock, dick, lingerie, masturbation, pain, small tits, solo, toys, transsexual

Wide-open anal whores love getting their butts stretched
10 months ago
5:14

VideoSection

Wide-open anal whores love getting their butts stretched

Tags: anal, ass, big ass, big cock, blowjob, gaping hole, ladyboy, pain, pov, slut

Pain loving solo TS babe in lingerie plays with her urethra
9 months ago
5:00

XXXDan

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