Dorm Room Punishment
11 years ago
6:37

aShemaleTube

Dorm Room Punishment

Tags: blowjob, domination, dorm, jessica fox, kinky, pornstar, punishment

Ab120 Voluntary M Slave Secretary - Cumshot.stocking Covered Glans Punishment
8 days ago
2:57

ShemaleZ

Ab120 Voluntary M Slave Secretary - Cumshot.stocking Covered Glans Punishment

Tags: anal, assfucking, bdsm, bondage, brunette, cumshot, domination

Submissive sissy gets her tight hole punished and then deeply penetrated
1 year ago
17:06

ShemaleTaxi

Submissive sissy gets her tight hole punished and then deeply penetrated

Tags: ass, punishment, shemale, sissy, submissive, tight, whip

Dirty Talking Tranny Punishes A Submissive Guy
3 years ago
5:57

getTranny

Dirty Talking Tranny Punishes A Submissive Guy

Tags: amateur, anal, bdsm, big cock, brunette, deep throat, dirty talk

Sexy Trans Sissy Steph gets Punished fucked by The BBC PUNISHER and takes a HUGE facial cums
8 months ago
1:58

aShemaleTube

Sexy Trans Sissy Steph gets Punished fucked by The BBC PUNISHER and takes a HUGE facial cums

Tags: anal, big black cock, blowjob, cowgirl, cum, cumshot, doggystyle

Tv Goddess Foxxy Punishes Loser Boyfriend
3 years ago
10:32

TrannyOne

Tv Goddess Foxxy Punishes Loser Boyfriend

Tags: anal, anus, ass, barebacking, bdsm, boyfriend, crossdressing

Dude Punished With Giant Long Black Cock
9 years ago
11:47

aShemaleTube

Dude Punished With Giant Long Black Cock

Tags: assfucking, barebacking, big cock, big tits, black, dick, hd

Punished And Anal With Natalie Mars
1 year ago
4:57

getTranny

Punished And Anal With Natalie Mars

Tags: anal, bdsm, bondage, brunette, fetish, hd, punishment

Denali Danger gets Punished #3 out now!!! Shes so amazing
7 months ago
2:14

aShemaleTube

Denali Danger gets Punished #3 out now!!! Shes so amazing

Tags: amazing, anal, big black cock, blowjob, cowgirl, cumshot, doggystyle

Four transsexual punishers in ebony leather outfits manhandle a man
1 year ago
6:29

ShemaleSin

Four transsexual punishers in ebony leather outfits manhandle a man

Tags: anal, bdsm, big cock, bondage, cumshot, domination, ebony

Hot tranny mistress Casey Kisses with a huge hard cock and big boobies pounds male slut using his hips to slam her cock deep inside him and feeds him
1 year ago
4:02

FapCat

Hot tranny mistress Casey Kisses with a huge hard cock and big boobies pounds male slut using his hips to slam her cock deep inside him and feeds him

Tags: anal, ass, barebacking, bdsm, big cock, big tits, blowjob

Beautiful transsexual punisher with large boobs bangs a dude until facial
1 year ago
8:14

ShemaleSin

Beautiful transsexual punisher with large boobs bangs a dude until facial

Tags: anal, bdsm, beauty, big cock, big tits, bondage, cumshot

Tgirl punisher Jeniffer Satine cums on a guy's chest after banging
1 year ago
7:06

ShemaleSin

Tgirl punisher Jeniffer Satine cums on a guy's chest after banging

Tags: anal, banging, bdsm, big cock, bondage, cum, cumshot

Arimura Nozomi, Nozomi Arimura And Suzune Nico - Nvh-055 Transsexual Bondage Training Lesbian Female Teacher Punishes Student 18+ As Extracurricular L
2 months ago
2:37:12

ShemaleZ

Arimura Nozomi, Nozomi Arimura And Suzune Nico - Nvh-055 Transsexual Bondage Training Lesbian Female Teacher Punishes Student 18+ As Extracurricular L

Tags: asian, bondage, japanese, lace, lesbian, lingerie, oriental

Tranny spanks and anal fucks motel manager
3 years ago
5:11

TrannyOne

Tranny spanks and anal fucks motel manager

Tags: anal, anus, ass, assfucking, bdsm, domination, hardcore

Punishing her bf's ass with a hot painal session
1 year ago
9:07

aShemaleTube

Punishing her bf's ass with a hot painal session

Tags: amateur, anal, ass, assfucking, hardcore, homevideo, punishment

Corporal Punishment on Spanking Bench using Whisks
7 months ago
37:50

JizzBunker

Corporal Punishment on Spanking Bench using Whisks

Tags: amateur, bdsm, couple, lingerie, mature, punishment, shemale

Very thick tranny enjoys some anal punishment
8 months ago
4:12

aShemaleTube

Very thick tranny enjoys some anal punishment

Tags: amateur, anal, big ass, hardcore, homevideo, punishment, shemale

Takes Parker To A Secret Dungeon, Punishes And Fucks Him With Sarina Valentina
49 days ago
38:54

ABTranny

Takes Parker To A Secret Dungeon, Punishes And Fucks Him With Sarina Valentina

Tags: anal, assfucking, babe, barebacking, big tits, blonde, bondage

crossdresser ballbusting
4 years ago
42:34

aShemaleTube

crossdresser ballbusting

Tags: amateur, ball busting, crossdressing, dick, domination, fetish, homevideo

Fat Slut deserve punishment from her Transgender Dominatrix
1 year ago
9:54

JizzBunker

Fat Slut deserve punishment from her Transgender Dominatrix

Tags: amateur, bbw, bdsm, chubby, couple, dominatrix, fat

Post Climax Punishment Compilation. 4 Outstanding Cumshots
4 years ago
4:46

ShemaleSin

Post Climax Punishment Compilation. 4 Outstanding Cumshots

Tags: beauty, big cock, big tits, compilation, cum, cumshot, ladyboy

Naughty TGirl maids get bondage and spanking punishment after being caught playing together
3 years ago
10:11

TrannyOne

Naughty TGirl maids get bondage and spanking punishment after being caught playing together

Tags: amateur, ass, bdsm, bondage, brunette, caught, crossdressing

She is Dominatrix Ladyboy punishing her slave with pain
1 year ago
13:33

RainblowXXX

She is Dominatrix Ladyboy punishing her slave with pain

Tags: bdsm, dominatrix, kinky, ladyboy, pain, punishment, shemale

Naughty shemale Nun Korra Del Rio punishing DJ in bondage with face fucking and cumming
5 months ago
5:07

aShemaleTube

Naughty shemale Nun Korra Del Rio punishing DJ in bondage with face fucking and cumming

Tags: blowjob, bondage, cum, cumshot, domination, face fucking, fetish

English mother I'd like to fuck and Crossdresser get a precious arse drubbing
1 year ago
11:32

ShemaleSin

English mother I'd like to fuck and Crossdresser get a precious arse drubbing

Tags: amateur, ass, bdsm, british, crossdressing, dress, english

Beautiful babes in watersports BDSM film: pee play, punishment, and humiliation. Featuring Mira Sunset.
9 months ago
13:24

ShemaleTaxi

Beautiful babes in watersports BDSM film: pee play, punishment, and humiliation. Featuring Mira Sunset.

Tags: babe, bdsm, beauty, big cock, bizarre, chained, domination

Transgender in chastity punished & anal fucked
1 year ago
5:05

RainblowXXX

Transgender in chastity punished & anal fucked

Tags: anal, bdsm, blowjob, bondage, domination, extreme, fetish

Sissy tgirl rough anal
8 years ago
28:21

FetishPapa

Sissy tgirl rough anal

Tags: amateur, anal, ass, extreme, punishment, rough, sissy

Dominatrix tranny punishes a chick in her mouth and pus
1 year ago
9:00

aShemaleTube

Dominatrix tranny punishes a chick in her mouth and pus

Tags: amateur, dominatrix, hd, punishment, shemale, tranny

U have been a nasty student. Now its time to be punished and compare jocks. Ever had a crush on your hawt teacher but the twist is u didnt know that b
2 years ago
11:38

ShemaleSin

U have been a nasty student. Now its time to be punished and compare jocks. Ever had a crush on your hawt teacher but the twist is u didnt know that b

Tags: amateur, ass, babe, latina, masturbation, pov, punishment

Bound up Femboy gets edged until that guy can't stop himself! (POST CLIMAX PUNISHMENT)
1 year ago
16:26

ShemaleSin

Bound up Femboy gets edged until that guy can't stop himself! (POST CLIMAX PUNISHMENT)

Tags: amateur, bdsm, bondage, bound, cum, cumshot, femdom

Brunette tranny punisher in black leather corset gets sucked by a dude
7 months ago
7:44

aShemaleTube

Brunette tranny punisher in black leather corset gets sucked by a dude

Tags: 3some, anal, big ass, big cock, big tits, black, blowjob

One blond and 2 brunette hair transsexual punishers spank and screw a dude
1 year ago
7:13

ShemaleSin

One blond and 2 brunette hair transsexual punishers spank and screw a dude

Tags: anal, bdsm, big cock, blonde, bondage, brunette, cumshot

Blonde Shemale Gave Punishment To Me For Overspeeding
1 year ago
6:14

FlyFlv

Blonde Shemale Gave Punishment To Me For Overspeeding

Tags: big cock, big tits, blonde, blowjob, cumshot, deep throat, handjob

Domina shemale punishes a dude's ass and mouth
7 months ago
6:20

aShemaleTube

Domina shemale punishes a dude's ass and mouth

Tags: amateur, anal, ass, domination, dominatrix, face fucking, hardcore

Sissy Charlotte gets flogged and Electro stim on her cock
3 years ago
8:28

TrannyOne

Sissy Charlotte gets flogged and Electro stim on her cock

Tags: amateur, bdsm, british, crossdressing, dick, domination, english

Shemale in a cage, fisted and punished, only in Germany
1 year ago
9:35

XXXDan

Shemale in a cage, fisted and punished, only in Germany

Tags: anal, bdsm, cage, fisting, german, latina, masturbation

TRANSSEXUAL PUNISHERS - Sexy and Kinky Tranny Domination
1 year ago
19:54

ShemaleSin

TRANSSEXUAL PUNISHERS - Sexy and Kinky Tranny Domination

Tags: anal, bdsm, big cock, bondage, cumshot, domination, fetish

Verified amateur rough anal first time Punish my nineteen year-old bum
4 years ago
6:01

TrannyOne

Verified amateur rough anal first time Punish my nineteen year-old bum

Tags: amateur, anal, anus, ass, first time, old, punishment

Busty shemale in fishnets punishes her partner
2 years ago
7:15

aShemaleTube

Busty shemale in fishnets punishes her partner

Tags: amateur, anal, assfucking, big tits, domination, fishnet, homevideo

Cheating TS punished by team fuck hotties with cum in own throat
4 years ago
10:00

ShemaleSin

Cheating TS punished by team fuck hotties with cum in own throat

Tags: cheating, cum, gangbang, group sex, hardcore, punishment, shemale

Punishment
2 years ago
5:21

aShemaleTube

Punishment

Tags: bdsm, crossdressing, domination, hd, punishment, shemale, slave

I Will Punish You With My Dick!
6 years ago
3:59

FlyFlv

I Will Punish You With My Dick!

Tags: ass, bdsm, bella rossi, big ass, big tits, dick, domination

Six shemale cops punish just one criminal man
5 years ago
5:05

TrannyOne

Six shemale cops punish just one criminal man

Tags: amateur, cop, domination, group sex, juicy, orgy, punishment

Busty shemale punisher in black leather boots fucks a tied up stud
7 months ago
5:28

aShemaleTube

Busty shemale punisher in black leather boots fucks a tied up stud

Tags: 3some, anal, big ass, big cock, big tits, black, blowjob

Massage session with the kinky TS babe turns into an amazing anal fuck for the lucky lad
4 years ago
15:58

TrannyOne

Massage session with the kinky TS babe turns into an amazing anal fuck for the lucky lad

Tags: amazing, anal, anus, ass, assfucking, babe, beauty

Anal cd punishment
9 years ago
8:40

aShemaleTube

Anal cd punishment

Tags: anal, crossdressing, domination, punishment, redhead, shemale, sucking

Hot shemale professor gives the naughty guy a punishment he will never forget
3 years ago
31:13

TrannyOne

Hot shemale professor gives the naughty guy a punishment he will never forget

Tags: anal, anus, ass, barebacking, big tits, blonde, couple

resigned trans after being punished
4 months ago
0:28

ShemaleSin

resigned trans after being punished

Tags: amateur, argentinian, ass, bdsm, big ass, latina, nerdy

Bound shemale slave anal fucked and punished
1 year ago
5:07

KeekAss

Bound shemale slave anal fucked and punished

Tags: anal, bdsm, big cock, blowjob, bondage, bound, brunette

Shemale domination with big dick - submissive shemale slave receives hardcore punishment
1 year ago
8:24

ShemaleTaxi

Shemale domination with big dick - submissive shemale slave receives hardcore punishment

Tags: anal, bdsm, big cock, bondage, creampie, cumshot, domination

TS Kendall Penny dominates Bussy Bradley with  BDSM
5 months ago
6:55

FapCat

TS Kendall Penny dominates Bussy Bradley with BDSM

Tags: anal, bdsm, big cock, blowjob, brunette, cum in mouth, cum swallowing

Pre Op Trans Girl Slut Sarah Gets Punished By Her Wife Mistress Petula - Teaser Video
2 years ago
5:25

getTranny

Pre Op Trans Girl Slut Sarah Gets Punished By Her Wife Mistress Petula - Teaser Video

Tags: amateur, bdsm, big ass, domination, femdom, lingerie, mistress

Sexy sissy squirts fer her daddy
3 years ago
4:16

TrannyOne

Sexy sissy squirts fer her daddy

Tags: crossdressing, daddies, female orgasm, gay, hd, masturbation, orgasm

Bustylicious blonde shemale punishing a nerdy guy's asshole
2 years ago
7:39

aShemaleTube

Bustylicious blonde shemale punishing a nerdy guy's asshole

Tags: amateur, anal, ass, assfucking, blonde, hardcore, homevideo

Day 01 of Punishment
10 months ago
19:41

XXXDan

Day 01 of Punishment

Tags: big ass, big tits, latex, latina, masturbation, punishment, shemale

First time straight latino fucks Crossdresser
3 years ago
4:32

TrannyOne

First time straight latino fucks Crossdresser

Tags: anal, anus, ass, barebacking, couple, creampie, crossdressing

Rough anal strapon guy and whipped ass Mia Martinez Xmas Punishment
4 years ago
5:01

TrannyOne

Rough anal strapon guy and whipped ass Mia Martinez Xmas Punishment

Tags: anal, anus, ass, punishment, rough, shemale, strap-on

After a entire sunday being in different dresses and jerking off and cumming all over the place, I had to get punished for being such a sexually excit
2 years ago
6:44

ShemaleSin

After a entire sunday being in different dresses and jerking off and cumming all over the place, I had to get punished for being such a sexually excit

Tags: amateur, bdsm, cum, domination, fetish, jerking, ladyboy

Jaycis sissy clitty punishment
9 months ago
20:25

XXXDan

Jaycis sissy clitty punishment

Tags: amateur, bdsm, big cock, british, clit, crossdressing, dick

HOT black CD Strawbee gets punished and shares 2 Hung cocks
9 months ago
2:28

aShemaleTube

HOT black CD Strawbee gets punished and shares 2 Hung cocks

Tags: anal, big black cock, black, blowjob, cumshot, dick, doggystyle

Mean tranny babe punishing her slave
1 year ago
5:36

aShemaleTube

Mean tranny babe punishing her slave

Tags: amateur, anal, assfucking, babe, hardcore, homevideo, punishment

Tgirl floozyjezebelle punishing her big ass with huge toys
5 months ago
9:08

aShemaleTube

Tgirl floozyjezebelle punishing her big ass with huge toys

Tags: amateur, anal, big ass, compilation, dildo, fetish, hd

Femboy Pusa gets punished! Full 20 min video available now 😈
6 months ago
2:04

aShemaleTube

Femboy Pusa gets punished! Full 20 min video available now 😈

Tags: anal, barebacking, big black cock, blowjob, cumshot, dick, doggystyle

Dominant Mrs. Samantha punishes and humiliates mega-slut Els, restrained with a chain
1 year ago
9:12

ShemaleTaxi

Dominant Mrs. Samantha punishes and humiliates mega-slut Els, restrained with a chain

Tags: abuse, bdsm, chained, domination, high heels, lingerie, punishment

Naughty Transsexual Is Fucked Deep In Her Ass And Dominated
13 years ago
3:03

FlyFlv

Naughty Transsexual Is Fucked Deep In Her Ass And Dominated

Tags: anal, ass, bdsm, big ass, brunette, condom, domination

Sissy Slave Punishment
1 year ago
10:12

XXXDan

Sissy Slave Punishment

Tags: anal, bdsm, couple, punishment, shemale, sissy, slave

Punished for disrespecting headmistress JaydenCherry
6 months ago
0:57

ShemaleSin

Punished for disrespecting headmistress JaydenCherry

Tags: amateur, public, punishment

Marina shackled up to the ceiling by her Mrs Samantha, then punished by Thrashing and being teased with various attributes including 2 sex toys
3 years ago
35:12

ShemaleSin

Marina shackled up to the ceiling by her Mrs Samantha, then punished by Thrashing and being teased with various attributes including 2 sex toys

Tags: amateur, blowjob, domination, dutch, lingerie, mature, punishment

Sissy cums likewise early and gets punished with coarse banging
4 years ago
2:35

ShemaleSin

Sissy cums likewise early and gets punished with coarse banging

Tags: amateur, ass, banging, barebacking, bdsm, big cock, cum

Small tits trans Izzy Wilde n milf anal fuck a guy in 3some
3 years ago
6:11

TrannyOne

Small tits trans Izzy Wilde n milf anal fuck a guy in 3some

Tags: 3some, anal, anus, ass, assfucking, barebacking, deep throat

Her hot sub is quite addicted to her punishment
4 years ago
8:04

ShemalePub

Her hot sub is quite addicted to her punishment

Tags: gorgeous, punishment, seduce, shemale, transsexual

Amateur caught cheating and ebony tit cumshot Mia Martinez Xmas Punish
4 years ago
5:01

TrannyOne

Amateur caught cheating and ebony tit cumshot Mia Martinez Xmas Punish

Tags: amateur, black, caught, cheating, cum, cumshot, ebony

Hard spanking
4 years ago
10:51

aShemaleTube

Hard spanking

Tags: crossdressing, punishment, shemale, spanking

Three busty shemales in black lingerie punish their tied up lover
8 months ago
7:34

aShemaleTube

Three busty shemales in black lingerie punish their tied up lover

Tags: 3some, anal, big ass, big cock, big tits, black, blowjob

Dominant t-doll Honey Foxxx punishes her submissive after giving a blowjob
6 months ago
6:07

ShemaleTaxi

Dominant t-doll Honey Foxxx punishes her submissive after giving a blowjob

Tags: bdsm, blowjob, doll, domination, punishment, rimjob, shemale

Naughty TS babe Lianna Lawson caged punished and fucked deep
6 months ago
6:55

FapCat

Naughty TS babe Lianna Lawson caged punished and fucked deep

Tags: anal, ass, babe, bdsm, big cock, blonde, blowjob

Being out for some punishment
6 months ago
0:49

aShemaleTube

Being out for some punishment

Tags: crossdressing, ladyboy, pantyhose, punishment, shemale, sissy, stockings

Worship my feet or face a naughty punishment - Female domination foot fetish
1 year ago
8:58

ShemaleTaxi

Worship my feet or face a naughty punishment - Female domination foot fetish

Tags: bdsm, feet, femdom, fetish, naughty, pov, punishment

Cherry Punishes My Lewd Aperture With Her Biggest Knob
2 years ago
11:56

ShemaleSin

Cherry Punishes My Lewd Aperture With Her Biggest Knob

Tags: anal, babe, barebacking, close up, doggystyle, pornstar, punishment

SADOMASOCHISM self servitude anal punishment with automatic massive pump sex-toy - pumps mercilessly larger and larger - CUP Z huge titties crossdress
3 years ago
5:18

ShemaleSin

SADOMASOCHISM self servitude anal punishment with automatic massive pump sex-toy - pumps mercilessly larger and larger - CUP Z huge titties crossdress

Tags: anal, anal toying, ass, bdsm, big ass, big tits, bondage

Denali Danger gets Punished
11 months ago
3:00

aShemaleTube

Denali Danger gets Punished

Tags: anal, big black cock, blowjob, cowgirl, cumshot, doggystyle, facial

See as hawt as bang trans boss Eva Maxim punishes her boy empolyee with her rod.
2 years ago
12:52

ShemaleSin

See as hawt as bang trans boss Eva Maxim punishes her boy empolyee with her rod.

Tags: babe, barebacking, big black cock, big tits, blowjob, boss, boy

TS Yoga Instructor Dominates Foot-Sniffer
3 years ago
10:56

TrannyOne

TS Yoga Instructor Dominates Foot-Sniffer

Tags: anal, anus, ass, bdsm, coach, domination, extreme

2023-05-13 LaraSukkuba Large Ramrod Ball Punishment Shiny Hose Precum - 1St Live-Stream
2 years ago
9:14

ShemaleSin

2023-05-13 LaraSukkuba Large Ramrod Ball Punishment Shiny Hose Precum - 1St Live-Stream

Tags: anal, anal toying, big cock, cum, dutch, fetish, homevideo

Dominic Pacifico & Lianna Lawson in Bad Little Bitch: Lianna Lawson Punished, Suspended and Fucked - TSSeduction
5 years ago
4:00

XShemale

Dominic Pacifico & Lianna Lawson in Bad Little Bitch: Lianna Lawson Punished, Suspended and Fucked - TSSeduction

Tags: bdsm, bitch, blonde, fetish, punishment, shemale, small tits

Slave training and punishment first time If you're going to be a c
4 years ago
8:01

TrannyOne

Slave training and punishment first time If you're going to be a c

Tags: domination, first time, punishment, shemale, slave

Naughty Shemale Nun Punishing Man
39 days ago
4:57

ShemaleZ

Naughty Shemale Nun Punishing Man

Tags: bdsm, big tits, bondage, brunette, cumshot, domination, facial

Nasty thief gets punished for robbing by getting his ass stretched wide by the hot trans chick's huge Tcock
4 years ago
1:00:06

TrannyOne

Nasty thief gets punished for robbing by getting his ass stretched wide by the hot trans chick's huge Tcock

Tags: anal, anus, ass, ass to mouth, assfingering, bdsm, big cock

One blonde and three brunette tranny punishers fuck a dude till facials
1 year ago
6:30

aShemaleTube

One blonde and three brunette tranny punishers fuck a dude till facials

Tags: 3some, anal, big ass, big cock, big tits, blonde, blowjob

Steamy Shemale Takes on Slut
15 years ago
27:45

aShemaleTube

Steamy Shemale Takes on Slut

Tags: big tits, latina, punishment, shemale, slut, small tits

Three busty shemales in leather boots punish a dude until cumshots
8 months ago
8:44

aShemaleTube

Three busty shemales in leather boots punish a dude until cumshots

Tags: 3some, anal, big ass, big cock, big tits, blowjob, boots

Ts Belatriz Fucked Bareback And Punished Roughly
2 years ago
5:57

ShemaleZ

Ts Belatriz Fucked Bareback And Punished Roughly

Tags: ass to mouth, barebacking, brazilian, fetish, latina, pov, punishment

Rika Fox gets punished and takes a MASSIVE facial full video available now
3 months ago
1:24

aShemaleTube

Rika Fox gets punished and takes a MASSIVE facial full video available now

Tags: anal, big black cock, blowjob, cowgirl, cumshot, doggystyle, facial

Naughty Daphne, Receiving Punishment And Rewards From Head Mistress Samantha!
8 months ago
7:59

getTranny

Naughty Daphne, Receiving Punishment And Rewards From Head Mistress Samantha!

Tags: amateur, blonde, bondage, domination, dutch, high heels, lace

Corporalist punishes me for being nasty pt. two
1 year ago
1:04

ShemaleSin

Corporalist punishes me for being nasty pt. two

Tags: amateur, anal, bondage, couple, domination, fetish, handcuffed

The large wang tgirl has a fresh thrall. 1St that babe is showing him his fresh role. Then the punishment begins and the mastix is hammering the pet w
2 years ago
3:10

ShemaleSin

The large wang tgirl has a fresh thrall. 1St that babe is showing him his fresh role. Then the punishment begins and the mastix is hammering the pet w

Tags: amateur, anal, babe, barebacking, bdsm, big cock, cumshot

Sissy Husband Gets Caught Crossdressing and Punished
3 years ago
5:00

TrannyOne

Sissy Husband Gets Caught Crossdressing and Punished

Tags: caught, crossdressing, hd, husband, punishment, shemale, sissy

Breasty tranny punisher in ebony leather boots bangs a bound up chap
8 months ago
5:33

ShemaleSin

Breasty tranny punisher in ebony leather boots bangs a bound up chap

Tags: anal, bdsm, big cock, bondage, boots, bound, cumshot

Shemales Punish Their Little Man Slut
11 years ago
3:00

FlyFlv

Shemales Punish Their Little Man Slut

Tags: 4some, black, blonde, bondage, domination, outdoor, punishment

Punishing my balls and dick huge cumshot
3 months ago
0:30

aShemaleTube

Punishing my balls and dick huge cumshot

Tags: anal, ball busting, balls, bdsm, big ass, big cock, cumshot

Hispanic sissy gets fucked her her little skirt by The BBC PUNISHER and takes a nasty facial
9 months ago
3:15

aShemaleTube

Hispanic sissy gets fucked her her little skirt by The BBC PUNISHER and takes a nasty facial

Tags: anal, big black cock, blowjob, cumshot, doggystyle, facial, hd

Three busty shemales in leather boots punish a guy until
1 year ago
8:49

JizzBunker

Three busty shemales in leather boots punish a guy until

Tags: big tits, boots, leather, punishment, shemale

Huge tits tranny in lingerie punishes bf
3 years ago
5:10

TrannyOne

Huge tits tranny in lingerie punishes bf

Tags: anal, anus, ass, barebacking, bdsm, big cock, big tits

Mrs Samantha has her serf t-girl Marina shackled to the ceiling, and punishes her by drubbing with a whip, flogger and paddle. Then teases her with so
3 years ago
14:09

ShemaleSin

Mrs Samantha has her serf t-girl Marina shackled to the ceiling, and punishes her by drubbing with a whip, flogger and paddle. Then teases her with so

Tags: amateur, bdsm, dutch, ladyboy, lingerie, mature, punishment

They punish a married dude while his gf is filming
2 years ago
10:40

aShemaleTube

They punish a married dude while his gf is filming

Tags: amateur, anal, assfucking, domination, girlfriend, hardcore, hd

Submissive lesbian punished with spanking and anal penetration
9 months ago
5:17

ShemaleTaxi

Submissive lesbian punished with spanking and anal penetration

Tags: anal, ass, bdsm, bondage, fisting, gaping hole, lesbian

Italian Tranny Anna Hickiman Punishes Wardrobe Attendant feat. Anna Hickhiman trans,Tommy Bravo - Trans n Shemale
9 months ago
16:12

XXXDan

Italian Tranny Anna Hickiman Punishes Wardrobe Attendant feat. Anna Hickhiman trans,Tommy Bravo - Trans n Shemale

Tags: anal, blowjob, brazilian, cumshot, handjob, italian, lingerie

Cute and nude sissy femboy pmb with jewelry only.
3 years ago
4:33

TrannyOne

Cute and nude sissy femboy pmb with jewelry only.

Tags: 18 year old, adorable, amateur, asian, big cock, crossdressing, cute

Hawt latin t-girl punishes a favourable stud.
3 years ago
6:37

ShemaleSin

Hawt latin t-girl punishes a favourable stud.

Tags: anal, ass, boyfriend, hardcore, latina, punishment, shemale

Colleen TS Self Paddling - at least 100 strokes
5 years ago
1:21

aShemaleTube

Colleen TS Self Paddling - at least 100 strokes

Tags: amateur, ass, crossdressing, homevideo, pain, punishment, shemale

spanking and whipping crossdressers
3 years ago
11:01

TrannyOne

spanking and whipping crossdressers

Tags: crossdressing, gay, hd, punishment, shemale, spanking, transvestite

Blindfolded maid Arielle Aquinas is punished by shemale mistress Roxxie Moth
1 year ago
5:06

aShemaleTube

Blindfolded maid Arielle Aquinas is punished by shemale mistress Roxxie Moth

Tags: blindfolded, blowjob, domination, fetish, hd, maid, mistress

Blonde tranny is punished & suspended
1 year ago
5:04

FapNow

Blonde tranny is punished & suspended

Tags: anal, bdsm, blonde, blowjob, bondage, domination, extreme

Sexy Young Trans Denali Danger gets Punished #3 full video available now!
6 months ago
1:33

aShemaleTube

Sexy Young Trans Denali Danger gets Punished #3 full video available now!

Tags: anal, big black cock, blowjob, cowgirl, cumshot, doggystyle, facial

Punishing a slave for a lost teaspoon
30 days ago
11:39

aShemaleTube

Punishing a slave for a lost teaspoon

Tags: anal, big ass, crossdressing, lingerie, pantyhose, punishment, shemale

Stella Rae in Stella Rae: Hi Step Daddy!
3 years ago
7:55

TrannyOne

Stella Rae in Stella Rae: Hi Step Daddy!

Tags: amateur, bend over, big cock, blonde, blowjob, bush, caught

Redhead ts mistress punishes a dude
59 days ago
7:48

aShemaleTube

Redhead ts mistress punishes a dude

Tags: amateur, anal, big tits, hardcore, homevideo, mistress, punishment

Big ass shemale punisher in leather corset fucks a stud doggystyle
8 months ago
6:44

aShemaleTube

Big ass shemale punisher in leather corset fucks a stud doggystyle

Tags: 3some, anal, big ass, big cock, big tits, blowjob, corset

Group of four shemale punishers dominate a guy until he cums
1 year ago
6:47

ShemaleMovie

Group of four shemale punishers dominate a guy until he cums

Tags: anal, bdsm, big cock, bondage, creampie, cum, cumshot

Daddy Spanks & Fucks Femboy Chrissy
4 years ago
14:52

TrannyOne

Daddy Spanks & Fucks Femboy Chrissy

Tags: amateur, american, anal, ass, barebacking, crossdressing, daddies

Gagged sissy punishes herself.
9 months ago
2:03

ShemaleSin

Gagged sissy punishes herself.

Tags: amateur, bondage, fetish, gagging, punishment, sissy

Domination, punishment, and discipline for transgender princess Emma Lee in lingerie and tights
11 months ago
5:24

ShemaleTaxi

Domination, punishment, and discipline for transgender princess Emma Lee in lingerie and tights

Tags: crossdressing, domination, latex, lingerie, panties, punishment, shemale

Three shemale punishers in black leather boots fuck their prisoner
8 months ago
7:22

aShemaleTube

Three shemale punishers in black leather boots fuck their prisoner

Tags: 3some, anal, big ass, big cock, big tits, black, blowjob

Teen girls friends first time and hot teen lesbian punished One of the
4 years ago
8:01

TrannyOne

Teen girls friends first time and hot teen lesbian punished One of the

Tags: first time, friend, lesbian, punishment, shemale, teen (18+)

You were a naughty stud! As punishment, kick yourself while you jerk off in this JOI session with TV_Helena
3 months ago
7:53

ShemaleTaxi

You were a naughty stud! As punishment, kick yourself while you jerk off in this JOI session with TV_Helena

Tags: bdsm, big tits, cum, domination, german, glasses, humiliation

One guy gets punished with six shemale dicks
5 years ago
5:05

TrannyOne

One guy gets punished with six shemale dicks

Tags: amateur, dick, gangbang, group sex, orgy, punishment, shemale

Naughty Tgirl gets an anal punishment from her teacher (Subtitled)
2 years ago
10:53

ShemaleTaxi

Naughty Tgirl gets an anal punishment from her teacher (Subtitled)

Tags: anal, blowjob, college, emo, goth, naughty, punishment

Tgirl dominant-bitch Korra Del Rio Korra puts a sub boy on his back and gives him a mouth screwing that makes his cock additional hard and on edge! No
2 years ago
4:05

ShemaleSin

Tgirl dominant-bitch Korra Del Rio Korra puts a sub boy on his back and gives him a mouth screwing that makes his cock additional hard and on edge! No

Tags: anal, ass, babe, banging, barebacking, bisexual, bitch

Three shemale punishers dominate a dude outdoors until triple cumshot
8 months ago
7:33

aShemaleTube

Three shemale punishers dominate a dude outdoors until triple cumshot

Tags: 3some, anal, big ass, big cock, big tits, blowjob, cumshot

Japanese FGO spy cosplayer gets defeated and subjected to various sexual punishments by her enemies - a wild ride of pleasure ensues!
1 year ago
5:18

ShemaleTaxi

Japanese FGO spy cosplayer gets defeated and subjected to various sexual punishments by her enemies - a wild ride of pleasure ensues!

Tags: crossdressing, hidden cam, japanese, ladyboy, punishment, shemale, wild

TGIRLS HOOKUP: Lying Top Gets Humiliated & Punished!
1 year ago
2:00

RainblowXXX

TGIRLS HOOKUP: Lying Top Gets Humiliated & Punished!

Tags: abuse, anal, ass, barebacking, beauty, big cock, blowjob

Chubby shemale domme likes punishing her slave
4 years ago
8:02

ShemalePub

Chubby shemale domme likes punishing her slave

Tags: chubby, domination, punishment, seduce, shemale, slave, transsexual

Self punishment and anal play
8 months ago
16:29

ShemaleSin

Self punishment and anal play

Tags: amateur, anal, anal toying, bondage, buttplug, dildo, extreme

TS Ryder Monroe bound fisted and fucked hard in AI punishment
5 months ago
6:55

FapCat

TS Ryder Monroe bound fisted and fucked hard in AI punishment

Tags: anal, big cock, blonde, blowjob, bondage, bound, creampie

Busty blonde tranny dominatrix Gia punishes and humiliates her lover
7 years ago
15:03

TrannyOne

Busty blonde tranny dominatrix Gia punishes and humiliates her lover

Tags: abuse, big tits, blonde, dick, dominatrix, juicy, punishment

Thicc black shemale pleasuring her cock
3 years ago
5:42

TrannyOne

Thicc black shemale pleasuring her cock

Tags: ass, assfingering, bbw, black, booty, couch, cum

Skinny MILF shemale stepmom punish fucked stepsons ass
6 years ago
6:00

aShemaleTube

Skinny MILF shemale stepmom punish fucked stepsons ass

Tags: anal, ass, big tits, blonde, blowjob, milf, punishment

The BBC PUNISHER Only Fans Preview
1 year ago
3:21

aShemaleTube

The BBC PUNISHER Only Fans Preview

Tags: balls, barebacking, big black cock, blowjob, cowgirl, doggystyle, hd

shemale punishers Agatha Trajano
5 years ago
19:17

TrannyOne

shemale punishers Agatha Trajano

Tags: doggystyle, group sex, punishment, shemale

ANAL LOVE
3 years ago
10:00

TrannyOne

ANAL LOVE

Tags: anal, anus, ass, big cock, booty, cfnm, creampie

Three transgender punishers dominate a guy in hardcore gangbang session
1 year ago
6:30

ShemaleMovie

Three transgender punishers dominate a guy in hardcore gangbang session

Tags: anal, bdsm, big cock, bondage, creampie, cumshot, domination

Denali Danger gets Punished #2
10 months ago
2:19

aShemaleTube

Denali Danger gets Punished #2

Tags: anal, big black cock, blowjob, cowgirl, cumshot, doggystyle, facial

Busty Yasmin Andrade punishes her slave and fucks him from
7 months ago
8:24

IcePorn

Busty Yasmin Andrade punishes her slave and fucks him from

Tags: bdsm, big ass, big tits, blowjob, cumshot, dick, gangbang

this bad slut behind the cage get to be punished
2 years ago
18:41

ShemaleSin

this bad slut behind the cage get to be punished

Tags: 3some, anal, big cock, blowjob, cage, cumshot, hardcore

Bound Shemale Slave Anal Fucked And Punished
1 year ago
4:57

getTranny

Bound Shemale Slave Anal Fucked And Punished

Tags: anal, bdsm, big tits, bondage, bound, brunette, hardcore

SADOMASOCHISM Punishment
2 years ago
2:49

ShemaleSin

SADOMASOCHISM Punishment

Tags: amateur, bdsm, domination, european, ladyboy, lingerie, mature

Ladyboy blowjob spanking bdsm compilation
4 years ago
20:15

TrannyOne

Ladyboy blowjob spanking bdsm compilation

Tags: amateur, anal, anus, ass, bdsm, blowjob, compilation

Brunette Punisher Viviany Aguilera Strokes Her Monster Cock Until Cumshot
7 months ago
7:03

ABTranny

Brunette Punisher Viviany Aguilera Strokes Her Monster Cock Until Cumshot

Tags: 3some, big ass, big cock, big tits, booty, booty shake, brunette

Kinky latex wearing transsexual slut fucks a kinky male toy lover
4 years ago
38:43

TrannyOne

Kinky latex wearing transsexual slut fucks a kinky male toy lover

Tags: anal, anus, ass, assfingering, bdsm, bed sex, bedroom

Sizzling oriental shemale gets some drilling and gets punished
4 years ago
6:12

ShemaleSin

Sizzling oriental shemale gets some drilling and gets punished

Tags: anal, big cock, big tits, black, cowgirl, doggystyle, drilling

Amateur ladyboy Emie wears kinky hose, handcuffs and collar. This Babe is willing to do what her slavemaster says, that babe willing to please her dom
1 year ago
6:27

ShemaleSin

Amateur ladyboy Emie wears kinky hose, handcuffs and collar. This Babe is willing to do what her slavemaster says, that babe willing to please her dom

Tags: amateur, anal, asian, ass, assfucking, babe, blowjob

Gerald resolves Tina needs to be spanked
4 years ago
3:41

ShemaleSin

Gerald resolves Tina needs to be spanked

Tags: british, lingerie, masturbation, mature, milf, punishment, solo

Poor guy gets his ass and mouth fucked to multiple orgasms by the mature blonde shemale
3 years ago
22:13

TrannyOne

Poor guy gets his ass and mouth fucked to multiple orgasms by the mature blonde shemale

Tags: anal, anus, ass, barebacking, bdsm, blonde, blowjob

Trio of dark-haired transgender princess punishers dominate a hunk in bondage
1 year ago
7:22

ShemaleMovie

Trio of dark-haired transgender princess punishers dominate a hunk in bondage

Tags: anal, bdsm, big cock, bondage, creampie, cumshot, dark hair

Three Transsexuals Are Dominating A Black Man
13 years ago
3:01

FlyFlv

Three Transsexuals Are Dominating A Black Man

Tags: 4some, bdsm, black, boots, brunette, domination, feet

Naughty TGirl maid bent over Milfs knee for ass spanking
4 years ago
10:06

TrannyOne

Naughty TGirl maid bent over Milfs knee for ass spanking

Tags: ass, bdsm, bend over, crossdressing, domination, feet, fetish

A Private Punishment
3 years ago
28:45

TrannyOne

A Private Punishment

Tags: american, bdsm, cowgirl, doggystyle, domination, extreme, femdom

Crossdressed twink fucked bareback by straight curious Arab
3 years ago
20:58

TrannyOne

Crossdressed twink fucked bareback by straight curious Arab

Tags: anal, anus, arab, ass, barebacking, big cock, creampie

Spanked teeny transexual assfingered by dom ginger
4 years ago
6:08

TrannyOne

Spanked teeny transexual assfingered by dom ginger

Tags: ass, assfingering, bdsm, domination, erotic, fetish, fingering

TS Jesse punishes a cis man and a TS man!
1 year ago
10:11

XXXDan

TS Jesse punishes a cis man and a TS man!

Tags: anal, bdsm, big ass, big tits, blowjob, hardcore, punishment

Larasukkuba Episode 4 - First live stream with a kinky tranny receiving oily ball punishment in shiny nylon pantyhose
1 year ago
5:18

ShemaleTaxi

Larasukkuba Episode 4 - First live stream with a kinky tranny receiving oily ball punishment in shiny nylon pantyhose

Tags: amateur, anal, anal toying, babe, beauty, big cock, feet

Slave for my mistress
4 years ago
11:45

TrannyOne

Slave for my mistress

Tags: amateur, anal, anus, ass, bdsm, bondage, crossdressing

Sissy outdoor public spanking
4 months ago
5:04

aShemaleTube

Sissy outdoor public spanking

Tags: crossdressing, hd, outdoor, public, punishment, shemale, sissy

Mndy Punishes Kim
1 year ago
8:00

getTranny

Mndy Punishes Kim

Tags: amateur, anal, bdsm, brunette, domination, natural tits, punishment

Golden-Haired resigned tranny Lianna Lawson is fastened to a metal device gets her penis wanked then in metal chastity anal drilled by the large knob
1 year ago
5:04

ShemaleSin

Golden-Haired resigned tranny Lianna Lawson is fastened to a metal device gets her penis wanked then in metal chastity anal drilled by the large knob

Tags: anal, bdsm, blonde, bondage, dick, domination, drilling

Taking Hung Midwest guy for a RIDE
4 years ago
6:04

TrannyOne

Taking Hung Midwest guy for a RIDE

Tags: anal, anus, ass, barebacking, big cock, booty, crossdressing

Brunette shemale punisher spanks and fucks her lover outdoors
1 year ago
6:51

aShemaleTube

Brunette shemale punisher spanks and fucks her lover outdoors

Tags: 3some, anal, big ass, big cock, big tits, blowjob, brunette

Cock Punishment - Pinko TGirls
1 year ago
0:37

Txxx

Cock Punishment - Pinko TGirls

Tags: big ass, big tits, dick, latina, lingerie, mature, punishment

Crossdresser punished
1 year ago
1:56:21

aShemaleTube

Crossdresser punished

Tags: amateur, crossdressing, domination, fetish, homevideo, punishment, shemale

Tgirl Dominates Delivery Man Worships Feet And Gets Fucked, S2
4 years ago
12:18

TrannyOne

Tgirl Dominates Delivery Man Worships Feet And Gets Fucked, S2

Tags: anal, anus, ass, barebacking, bdsm, big cock, big tits

Pet femboy puppy gets punished! POV (Teaser)
2 years ago
0:55

aShemaleTube

Pet femboy puppy gets punished! POV (Teaser)

Tags: cute, dick, fur, hd, model, pov, punishment

Dominant TS punisher in sexy boots ravages a submissive
8 months ago
5:34

HDSex

Dominant TS punisher in sexy boots ravages a submissive

Tags: 3some, anal, bdsm, big cock, blonde, bondage, boots

Lascivious Thai ladyboy Amy is always cheating her boyfriends, for what that babe always getting punished. After each cheating movie scene this babe s
1 year ago
6:26

ShemaleSin

Lascivious Thai ladyboy Amy is always cheating her boyfriends, for what that babe always getting punished. After each cheating movie scene this babe s

Tags: anal, asian, ass, assfucking, babe, barebacking, blowjob

sissy-transvestite fucked bare and spanked by chubby daddy
4 years ago
10:51

TrannyOne

sissy-transvestite fucked bare and spanked by chubby daddy

Tags: amateur, anal, anus, ass, barebacking, bdsm, chubby

Maid Joanna is Punished on Cam for wanking
10 months ago
31:00

XXXDan

Maid Joanna is Punished on Cam for wanking

Tags: anal, bdsm, femdom, hardcore, lingerie, maid, masturbation

Confession and punishment
8 months ago
12:20

XXXDan

Confession and punishment

Tags: anal, bdsm, big ass, big cock, granny, hardcore, latex

Naughty trans babe Chrystal punished for misbehaving
9 months ago
6:12

HDSex

Naughty trans babe Chrystal punished for misbehaving

Tags: anal, babe, blowjob, latina, naughty, pov, punishment

Raid Over Japan , Asian Ladyboy Punished And Fucked In The Ass Hardcore
4 years ago
25:50

TrannyOne

Raid Over Japan , Asian Ladyboy Punished And Fucked In The Ass Hardcore

Tags: anal, anus, ass, bdsm, blowjob, domination, hardcore