19 years old Anal Ladyboy Gets Cock
11 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
9 years ago
6:19

aShemaleTube

Ladyboy Pink Painful Bareback

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14 years ago
19:07

aShemaleTube

Teen guy cumsucker gets fucked painful by big ebony tranny

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Dude Takes A Painful Shemale Ass Fucking
9 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
11 years ago
3:00

FlyFlv

Oops, It's A Little Bit Painful For Him

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Shemale in white socks and fucks guy very painful
4 days ago
26:32

aShemaleTube

Shemale in white socks and fucks guy very painful

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Ladyboy Pang Jerking Off
10 years ago
6:25

aShemaleTube

Ladyboy Pang Jerking Off

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

TnaFlix

Transgender Bitch Electro TizORTURE Pain Slut

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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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Lesbians dominate and ass-fuck the plump pizza delivery girl Lily Labeau
3 months ago
5:34

ShemaleMovie

Lesbians dominate and ass-fuck the plump pizza delivery girl Lily Labeau

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Anal employee ate my ass, gonzo and painful, but horny! XXX!
4 months ago
6:53

VipTube

Anal employee ate my ass, gonzo and painful, but horny! XXX!

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Busty Cherry Torn gets pounded in a public bar
5 months ago
5:34

ShemaleMovie

Busty Cherry Torn gets pounded in a public bar

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Bbc Shemale fucks boy and cum inside ass
6 months ago
17:57

aShemaleTube

Bbc Shemale fucks boy and cum inside ass

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

XXXDan

Pain and pleasure, chastity and lust, Part 1

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Shemale takes cock in mouth
9 months ago
5:17

ShemaleMovie

Shemale takes cock in mouth

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

KeekAss

tony punishing his slave male nipples naked

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Pang1 - 4min Clip
11 months ago
3:59

XXXDan

Pang1 - 4min Clip

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Stacy Sadistic Has Her Way With Wet Pussy
13 days ago
10:59

aShemaleTube

Stacy Sadistic Has Her Way With Wet Pussy

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

ShemaleMovie

Big-breasted furry dominatrix anally pounds submissive man

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Sissy goes wild and releases with a bang!
5 days ago
12:59

VideoSection

Sissy goes wild and releases with a bang!

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tony performing his pain pervert punishment to his nipples
1 year ago
3:14

KeekAss

tony performing his pain pervert punishment to his nipples

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Kinky iris with new spike clamps, very painfull first time
1 year ago
6:52

XXXDan

Kinky iris with new spike clamps, very painfull first time

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Submissive ladyboy sucks and painfuly ass fucked
1 year ago
6:27

aShemaleTube

Submissive ladyboy sucks and painfuly ass fucked

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The pain in male ass because of hard shemale dick
2 years ago
6:14

aShemaleTube

The pain in male ass because of hard shemale dick

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thin shemale likes pain with pleasure
2 years ago
5:18

aShemaleTube

thin shemale likes pain with pleasure

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Teen Ladyboy Pang Changes Outfit And Jerks Off
3 years ago
6:02

aShemaleTube

Teen Ladyboy Pang Changes Outfit And Jerks Off

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Super Cute Teen Ladyboy Getting Fucked In The Ass Wit No Pain, Only Pleasure.
4 years ago
20:18

TrannyOne

Super Cute Teen Ladyboy Getting Fucked In The Ass Wit No Pain, Only Pleasure.

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GENDER X Extremely feminine looking TS Emma Rose fucks hot tutor guy
4 years ago
6:15

TrannyOne

GENDER X Extremely feminine looking TS Emma Rose fucks hot tutor guy

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Shemale fuck dude in public restroom
4 years ago
5:11

TrannyOne

Shemale fuck dude in public restroom

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Latex-clad nurse Lyla Storm gives a hard ass pounding to Red Riding in a hot bdsm session
3 months ago
5:35

ShemaleMovie

Latex-clad nurse Lyla Storm gives a hard ass pounding to Red Riding in a hot bdsm session

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Chocolate shemale giving painful anal to her sub partner
20 days ago
8:34

aShemaleTube

Chocolate shemale giving painful anal to her sub partner

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Fem-005 Sweet And Sadistic With Tachibana Serina And Serina Tachibana
4 months ago
2:02:44

ShemaleZ

Fem-005 Sweet And Sadistic With Tachibana Serina And Serina Tachibana

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Painful ponyplay on the Halloween party
3 years ago
23:17

TrannyOne

Painful ponyplay on the Halloween party

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Eurasian Persuasion, Punishing Loser
4 years ago
8:03

TrannyOne

Eurasian Persuasion, Punishing Loser

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Pornstars: sandra romain

Girl-on-girl action with some wild kink fun
5 months ago
5:36

ShemaleMovie

Girl-on-girl action with some wild kink fun

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Liinssarah fucks boytoy hard and cum inside ass
6 months ago
26:03

aShemaleTube

Liinssarah fucks boytoy hard and cum inside ass

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feet worship while fucked
8 months ago
2:14

aShemaleTube

feet worship while fucked

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Atm, porn-vido
9 months ago
5:17

ShemaleMovie

Atm, porn-vido

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

KeekAss

tony punishing his slave male nipples naked 2

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Owner Of XXX Shop Tries Gloryhole With A Trans - Jenna Creed
4 years ago
6:15

TrannyOne

Owner Of XXX Shop Tries Gloryhole With A Trans - Jenna Creed

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

XXXDan

Pang1 - Doggiestyle - 4min Clip

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

ShemaleMovie

Female dominatrix Mona Wales spanks and anally penetrates submissive male

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Magic helps sad tranny to recapture bf's heart
4 years ago
5:00

TrannyOne

Magic helps sad tranny to recapture bf's heart

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girls sadistic Cam Trans Cock
4 years ago
10:02

aShemaleTube

girls sadistic Cam Trans Cock

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Jaymee Castles And Stacy Sadistic - Fit Trans Beauties Go Bareback After A Gym Workout
2 months ago
29:21

ShemaleZ

Jaymee Castles And Stacy Sadistic - Fit Trans Beauties Go Bareback After A Gym Workout

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Trans man experiences nipple orgasm and moans in pleasure
1 year ago
5:56

ShemaleMovie

Trans man experiences nipple orgasm and moans in pleasure

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

Transgender princess indulges in sadistic and masochistic fun in Fallout 4
4 months ago
7:35

ShemaleMovie

Transgender princess indulges in sadistic and masochistic fun in Fallout 4

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No Pain, No Gain
1 year ago
10:35

aShemaleTube

No Pain, No Gain

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Ladyboy feels pain in ass after giving nice blowjob
1 year ago
6:23

aShemaleTube

Ladyboy feels pain in ass after giving nice blowjob

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Pain in the ass
2 years ago
1:12

aShemaleTube

Pain in the ass

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My patient was complaining of pain in his leg, so I treated him with ass tea on the table
2 years ago
5:58

aShemaleTube

My patient was complaining of pain in his leg, so I treated him with ass tea on the table

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I Know You Love This Black, Ebony Stick Of Pain
3 years ago
2:09

TrannyOne

I Know You Love This Black, Ebony Stick Of Pain

Tags: anal, anus, ass, bdsm, black, blowjob, domination, ebony, hardcore, licking

Unusual outdoor escapades with a hint of kink
4 months ago
5:35

ShemaleMovie

Unusual outdoor escapades with a hint of kink

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Sadistictranskitty KdamaGrey
3 years ago
1:32

aShemaleTube

Sadistictranskitty KdamaGrey

Tags: pain

crossdresser punishment
4 years ago
19:30

aShemaleTube

crossdresser punishment

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Electric Shock to my nippls..issss lovely pain and heaven for me...
4 years ago
2:52

aShemaleTube

Electric Shock to my nippls..issss lovely pain and heaven for me...

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Wife cuckolded by husband and trans maid Emma Rose
4 years ago
4:56

TrannyOne

Wife cuckolded by husband and trans maid Emma Rose

Tags: anal, anus, ass, assfucking, cheating, crossdressing, cuckold, extreme, hardcore, husband

Busty transsexual gives straight guy some painful delight
6 years ago
4:59

ShemaleZ

Busty transsexual gives straight guy some painful delight

Tags: big tits, lingerie, pain, stockings, transsexual

Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
4 months ago
44:11

JizzBunker

Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w

Tags: amateur, asslick, bdsm, beauty, big ass, crossdressing, fetish, hardcore, licking, pain

Kisses and pain in intimity
5 months ago
18:35

XXXDan

Kisses and pain in intimity

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

Pain and Pleasure
8 months ago
51:35

JizzBunker

Pain and Pleasure

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

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

ShemaleMovie

Big-dicks, rough-anal-sex

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

Sissy Trans Hazel Splashes Her Nads in the Woods!
10 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
11 months ago
10:29

ShemaleMovie

Rollenspiel, marionette

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

KeekAss

stacy sadomasochistic smacks wild kitten^utter on crimson^

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Caning, kinkysmut
6 months ago
5:40

ShemaleMovie

Caning, kinkysmut

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Three way, hermaphrodite
7 months ago
5:08

VideoSection

Three way, hermaphrodite

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Pain loving solo TS in lingerie toys her cock while wanking
1 year ago
5:00

PornGem

Pain loving solo TS in lingerie toys her cock while wanking

Tags: bdsm, dick, fishnet, lingerie, masturbation, pain, small tits, solo, stockings, toys

Hard-anal, anal-destruction
1 year ago
5:12

ShemaleMovie

Hard-anal, anal-destruction

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

Sexy TV bound on bed, severely whipped, spanked with many instruments
1 year ago
25:59

aShemaleTube

Sexy TV bound on bed, severely whipped, spanked with many instruments

Tags: bdsm, bed sex, bound, crop whip, domination, extreme, lingerie, pain, riding, slave

Steamy quickie with ladyboy Pang
9 months ago
5:06

AnalDin

Steamy quickie with ladyboy Pang

Tags: amateur, anal, asian, assfucking, blowjob, hardcore, ladyboy, pain, pov, quickie

shemale shemale pang a gets her butt fucked by a big de
2 years ago
5:06

aShemaleTube

shemale shemale pang a gets her butt fucked by a big de

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Kiss, pain, and intimate moments
2 years ago
18:34

aShemaleTube

Kiss, pain, and intimate moments

Tags: crossdressing, domination, fat, hd, kissing, latex, mature, pain

Painful dildo play
3 years ago
7:22

aShemaleTube

Painful dildo play

Tags: crossdressing, dildo, hd, masturbation, pain, solo, stockings

Big tits tranny Pang sucked dick before hard ass fucking by a white client
3 years ago
6:00

aShemaleTube

Big tits tranny Pang sucked dick before hard ass fucking by a white client

Tags: assfucking, barebacking, big cock, big tits, blowjob, dick, hd, lingerie, pain, pov

Skinny trans nanny takes care of the parent's needs too
4 years ago
6:15

aShemaleTube

Skinny trans nanny takes care of the parent's needs too

Tags: anal, babysitter, cute, flexible, hardcore, hd, pain, skinny, transsexual

tgirls prostitutes with lots of semen in their balls shoot like a cannon
4 years ago
21:58

TrannyOne

tgirls prostitutes with lots of semen in their balls shoot like a cannon

Tags: 18 year old, anal, anus, ass, assfucking, balls, blowjob, cum, cumshot, extreme

Blowing an Old Friend w Stacy Sadistic
6 years ago
15:30

ShemaleZ

Blowing an Old Friend w Stacy Sadistic

Tags: amateur, big cock, big tits, blonde, friend, hd, old, pain, redhead, small tits

Gorgeous trans beauty is open to some serious ass pounding
4 months ago
5:17

ShemaleMovie

Gorgeous trans beauty is open to some serious ass pounding

Tags: anal, ass, babe, beauty, big ass, big cock, blowjob, cum, first time, gaping hole

Fucking The Pain Away With Miss Nikita
6 months ago
5:22

aShemaleTube

Fucking The Pain Away With Miss Nikita

Tags: amateur, anal, barebacking, big cock, blonde, blowjob, cumshot, fetish, hd, mature

stacy sadomasochistic climax denial utter on crimson
6 months ago
5:45

KeekAss

stacy sadomasochistic climax denial utter on crimson

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

WELTS WHORE GET PAIN
8 months ago
0:30

aShemaleTube

WELTS WHORE GET PAIN

Tags: domination, hd, lingerie, pain, slut

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

ShemaleMovie

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

Tags: anal, ass, bdsm, blowjob, bondage, domination, drilling, group sex, hardcore, kinky

Pornstars: ashlynn leigh, james deen, princess donna

Wealthy entrepreneur dominated and pegged by a fierce female dominatrix
10 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
11 months ago
9:20

KeekAss

Taunting, edging my stud pleasure button

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

Hot quickie with ladyboy Pang
1 year ago
5:06

aShemaleTube

Hot quickie with ladyboy Pang

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

T-girl enjoys sucking and riding ass
1 year ago
5:17

ShemaleMovie

T-girl enjoys sucking and riding ass

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

Free-anal-videos, anal-video
1 year ago
5:18

VideoSection

Free-anal-videos, anal-video

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

Cute big tits tranny hot masturbation after passion posing in lingerie
1 year ago
6:15

aShemaleTube

Cute big tits tranny hot masturbation after passion posing in lingerie

Tags: asian, big tits, cute, hd, ladyboy, lingerie, masturbation, pain, passionate, posing

Anal fist fuck faggot love to feel the pain in the ass
3 years ago
18:02

TrannyOne

Anal fist fuck faggot love to feel the pain in the ass

Tags: anal, anal fisting, anus, ass, extreme, fisting, hardcore, pain

Shemale Sex Spanked By The Sadistic Sex Fiends, S1
3 years ago
3:05

TrannyOne

Shemale Sex Spanked By The Sadistic Sex Fiends, S1

Tags: anal, anus, ass, blowjob, hardcore, oral, pain, pornstar, punishment, spanking

Pornstars: cytherea

Pain and
4 years ago
8:48

aShemaleTube

Pain and

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Pain-Getting hard fucked
4 years ago
0:59

aShemaleTube

Pain-Getting hard fucked

Tags: 3some, anal, barebacking, big cock, crossdressing, cum in mouth, domination, gangbang, group sex, hardcore

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

ShemaleMovie

Slender lesbian enjoys anal plug and deep drilling session

Tags: anal, ass, bdsm, bondage, domination, drilling, gagging, lesbian, pain, pornstar

Pornstars: haley wilde

Trans College Girls Having Anal Afternoon
4 years ago
6:16

TrannyOne

Trans College Girls Having Anal Afternoon

Tags: 18 year old, 3some, anal, anus, ass, assfucking, blonde, blowjob, college, crossdressing

Crossdresser Enjoys a very Painful Flogging Session in
4 years ago
11:29

aShemaleTube

Crossdresser Enjoys a very Painful Flogging Session in

Tags: crossdressing, pain

Sissy anal plug and pain bra training
6 years ago
19:25

ShemaleZ

Sissy anal plug and pain bra training

Tags: amateur, anal, bra, fetish, pain, sissy

Anal-fucking, xvidioes
4 months ago
5:22

ShemaleMovie

Anal-fucking, xvidioes

Tags: anal, ass, asslick, big ass, blowjob, hardcore, licking, oral, pain, pov

Sapphic, marionette
6 months ago
5:40

ShemaleMovie

Sapphic, marionette

Tags: anal, ass, bdsm, bondage, domination, gagging, pain, pornstar, slave, tied up

Pornstars: phoenix marie

Pang1 - Trailer
11 months ago
1:56

XXXDan

Pang1 - Trailer

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

Pts-527 S-class Gal Shemale Intense Lesbian Sex, Super Sadistic Big-breasted Gal Creampie Oil Massage
7 months ago
2:25:13

ShemaleZ

Pts-527 S-class Gal Shemale Intense Lesbian Sex, Super Sadistic Big-breasted Gal Creampie Oil Massage

Tags: 3some, anal, asian, assfucking, big ass, big tits, blonde, booty, booty shake, creampie

Inked slave tied up and fucked by a dominant woman
11 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

Adult movie star, sissys
9 months ago
8:02

VideoSection

Adult movie star, sissys

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

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

ShemaleMovie

Public outdoor FFM anal penetration with strapon in various languages

Tags: anal, bdsm, bizarre, bondage, domination, european, ffm, group sex, hardcore, humiliation

Muscular Trans beauties ditch protection after hitting the gym
10 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
11 months ago
15:36

ShemaleMovie

Intense pleasure, pain play & submission

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

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

shemale and guy switch roles (painful anal)
1 year ago
9:20

aShemaleTube

shemale and guy switch roles (painful anal)

Tags: anal, big ass, pain

Redhead asian trans all covered in pain ass fucked doggystyle till facial
1 year ago
7:25

aShemaleTube

Redhead asian trans all covered in pain ass fucked doggystyle till facial

Tags: asian, assfucking, cumshot, doggystyle, facial, ladyboy, pain, redhead, teen (18+), transsexual

Gold Predator BBC Brutally Destroys White Sluts Hole & Makes Me Scream
1 year ago
10:28

aShemaleTube

Gold Predator BBC Brutally Destroys White Sluts Hole & Makes Me Scream

Tags: anal, big black cock, hd, model, pain, pornstar, screaming, sissy, slut, transsexual

Pornstars: candy ass

thin tranny likes pain with pleasure
2 years ago
5:18

aShemaleTube

thin tranny likes pain with pleasure

Tags: pain, solo, thin, tranny, webcam

Light dack girls enjoyng sexy threesome
2 years ago
43:40

TrannyOne

Light dack girls enjoyng sexy threesome

Tags: 3some, anal, big black cock, black, dick, hd, pain, transsexual

Painful Ass Fucking In The Office
2 years ago
5:00

TrannyOne

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TrannyOne

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aShemaleTube

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