SHEMALE • PUNISHMENT 1,830 videos

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‹1 2 3 4 5 ›

08:09 57%

Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged.

2 years ago

xHamster

crossdresser, spanking, femboy
01:03 83%

Sweet chocolate transsexual punishing her boyfriend

2 years ago

TXXX

ebony, boyfriend
16:06

Italian Tranny Punishes Wardrobe Attendant Feat Trans) Tommy Bravo - Trans N Shemale - Anna Hickiman And Anna Hickhiman

3 years ago

ShemaleZ

italian
08:00 88%

The Naughty Nun: Korra Del Rio Punishes Disgraceful Sinner Dj

3 years ago

GetTranny

femdom, bondage, feet, nun
04:43 56%

Sydney Screams And Cherry Mavrik In Youre Cucked & Punished By Trans Lesbian Horny Nuns 5 Min

3 years ago

HClips

latex, shemale, lesbian, nun, screaming
22:43 70%

Natasha Rusthy And Labelle Sandorran In Two Shemale Mistress Punish A Slave Guy

4 years ago

Upornia

femdom, shemale fucks guy, threesome
07:44

Winter bluu sock wrestling loser gets punished

4 years ago

TrannyOne

wrestling, socks, amateur
07:30

Innocence CD sissy maid punished & overlooked by femdom mistress EvilKitties

4 years ago

ShemaleTaxi

femdom, maid, crossdresser
13:27 54%

Punishment Spanking For Oversleeping And Not Taking Out Trash

4 years ago

ShemaleZ

spanking, interracial
23:46

Black TGirls Hardcore - Chyna & Lok

4 years ago

TrannyOne

black, hardcore
10:07 64%

Domination and pain with this 2 shemales hardcore punishment

5 years ago

xHamster

mature, femdom, latex, mature anal, couple
06:42 80%

Innocent lad gets punished by her tranny boss with hot anal pounding

6 years ago

BeMyHole

ass to mouth, natural, dress, boss
26:25 93%

Natalie Mars - Caught Punished

6 years ago

TXXX

fetish, caught, toys, shemale, domination
13:28 57%

Sissy in chastity punished and bareback fucked

7 years ago

ShemaleZ

chastity
03:36

Sissy punished 50 smacks with the cane.

7 years ago

ShemaleZ

fetish
10:09 57%

Spanish Chubby Wife Anally Punished by Hubbys Small

7 years ago

ShemaleZ

amateur, spanish, anal, chubby, wife
05:13

Nurses punishes tv with strapon cock

7 years ago

ShemaleZ

strapon, nurse, crossdresser
06:00

Facesitting asian domina punishes her slave

7 years ago

AShemaleTube

femdom, facesitting
08:00 54%

Mom punishes cronys daughter with strapon and step hidden c

8 years ago

IcePorn

mom, strapon, hidden, stepmom
05:09

Honey FoXXX Takes Down College Crush

3 months ago

TrannyGem

ladyboy, BDSM, femdom, domination, college
05:10 83%

TS Vaniity Mardi Gras Butt sex Shag Fest

4 months ago

Analdin

domination, bondage, public
15:10

Maintenance slapping for Kitsy. Oral and lovemaking following the penalty.

10 months ago

TrannyGem

feet, cute, blowjob, BDSM, spanking, tied, sissy
03:38

Piss Punishment & Human Ashtray

1 month ago

$$ FapHouse

FTM, fetish, pissing
01:28

TS Esther Gets Fucked and Facialed by The BBC PUNISHER #4 full video available now

2 months ago

AShemaleTube

facial, BBC, shemale, big cock
05:07

Busty tits cougar fucks tranny

3 months ago

Analdin

cumshot, femdom, cougar, mom
47:33 89%

Goddess Punishes Arrogant Boy Toy

3 months ago

TXXX

latex, fetish, BDSM, toys, domination, shemale fucks guy
01:29

TS Bubble Booty Esther Gets fucked by The BBC PUNISHER

3 months ago

AShemaleTube

shemale, anal, BBC
08:58

Masters directive No. 45: One-legged Suspension with electro-hitachi punishment

3 months ago

ShemaleMovie

pissing, outdoor, electro
19:16

Subby Gets Ass Punished by TS Sasha Blue

3 months ago

$$ FapHouse

mature, shemale
01:38

SEXY Mexican Mami Caricia De Angel Gets Fucked and Facialed by The BBC PUNISHER

4 months ago

AShemaleTube

blowjob, BBC, big cock, facial, mexican
05:09

Kayleigh Coxx Transsexual Fucks Mike

5 months ago

Analdin

domination, pegging, bondage
06:07

TS Victoria Neves Punished And Fucked Bareback Indoor

5 months ago

BeMyHole

ass licking, riding
01:37

HOT Sailor Moon orgy starring Jenny Wei,Rika Fox,The BBC PUNISHER and the homies

6 months ago

AShemaleTube

BBC, blowjob, anal, cumshot
01:30

Avery Angel Gets fucked and facialed by The BBC PUNISHER #1

6 months ago

AShemaleTube

BBC, cumshot, shemale, big cock, facial
01:17 86%

Sexy Young Trans Rika Fox gets fucked by The BBC PUNISHER

7 months ago

AShemaleTube

big cock, BBC, blowjob, cumshot
09:07

Stunning curly shemale punishes her bf

7 months ago

AShemaleTube

lingerie, shemale fucks guy
08:08

Self-training No.71 punishment training tabouret

7 months ago

ShemaleTaxi

pissing, train, japanese, BDSM, machine
01:29

Sexy TS Viviana Rose gets Punished, fucked, facial & fucked more!

7 months ago

AShemaleTube

shemale, blowjob
15:06

Punish Chair, Let Me Cum to Becoming a Fountain

8 months ago

$$ FapHouse

solo, stockings, sissy, dildo
05:09

Blonde Femdom Shemale Anal Pounding

8 months ago

TrannyGem

blonde, bondage, femdom, shemale, pegging, BDSM
07:46

Burglar Gets Punished By Hung Trannies Yasmin Dornelles & Bruna Ferrari

8 months ago

BeMyHole

big cock, shemale fucks guy, cumshot, blowjob, threesome
06:49

Punishes Trans Toy: Creampie Clean-up & Foot Worship After Defiance With Kora Bell And Mistress Kora Bell

10 months ago

ShemaleZ

shemale, femdom, feet
06:01

Chubby heshe domina punishes a big guy

10 months ago

TrannyOne

femdom, chubby, anal
10:31

How a Tgirl severely punishs her phat spunk-pump.

11 months ago

ShemaleMovie

cumshot, sissy, femboy, shemale, BDSM, tied
05:06

Shemale mistress Venus Lux punishes disobedient muscle sub Draven Navarro with bareback anal

11 months ago

AShemaleTube

muscle, shemale fucks guy, femdom
07:48 90%

Redhead ts mistress punishes a dude

1 year ago

AShemaleTube

homemade, shemale fucks guy, femdom, redhead, amateur
06:59 83%

TS Kate Zoha punishes Korra Del Rio with deep rough fucking

1 year ago

KeekAss

shemale, latex
01:49

Avery Angel gets deep strokes and fucked by The BBC PUNISHER! Full video available now

1 year ago

AShemaleTube

big cock, BBC, cumshot
07:10

Shemale goddess Yasmin Lee delivers a hot point of view punishment

1 year ago

XXXVogue

shemale fucks guy, shemale, bondage
01:59

Sexy Young Trans Denali Danger gets Punished #3 out now!

1 year ago

AShemaleTube

shemale, anal
06:57

Fit shemale domina punishing a dude and fucking him in the ass

1 year ago

AShemaleTube

big tits, shemale fucks guy, blowjob, threesome, femdom
02:13

Avery Angel gets fucked by The BBC PUNISHER and takes a nasty facial cumshot

1 year ago

AShemaleTube

big cock, facial, BBC
07:36

Brunette tranny punishers take a stud prisoner and fuck him doggystyle

1 year ago

AShemaleTube

big ass, shemale fucks guy, gangbang, fetish, group
02:30

Avery Angel gets Punished #2

1 year ago

AShemaleTube

anal, cumshot
43:35 60%

Corporal Punishment Session with Mistress Jamie Diaper Sis

1 year ago

JizzBunker

amateur, BDSM, femdom, diaper, lingerie, mature
20:30 76%

TSDOMME: Straight Guy Bound and Punished

1 year ago

xHamster

fetish, bondage, BDSM, gangbang, big cock, group
01:39 88%

Sissy Steph gets Punished by The BBC PUNISHER and takes a HUGE facial cumshot!

1 year ago

AShemaleTube

sissy, BBC, shemale, facial
07:06 83%

Platinum-blonde ladyboy punisher in leather harness fucks her slave

1 year ago

HDSex

satin, bondage, BDSM, monster, gangbang, leather, blonde
23:17 62%

Rulebreakers will be punished (futa dominating male)

1 year ago

XXXVogue

3D, futanari, shemale fucks guy
05:14

Blonde shemale Lianna Lawson gets punished and suspended for disobedience

1 year ago

XXXVogue

BDSM
26:04

Nikolly Gaucha punishes his partner

1 year ago

XXXDan

fetish, BDSM
36:50

Trans Buggers Bareback The Crook Who Wanted To Punish Her With Larissa Albuquerque

1 year ago

ShemaleZ

stockings, shemale, bareback
08:00

Yasmin Lee Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

2 years ago

xShemaleTube

secretary, shemale fucks guy, asian, boss
05:02

Punishes Him With Her Cock - Anastasia Penny And Rock Solid

2 years ago

ShemaleZ

domination
06:31

Four shemale punishers fuck a stud in bondage doggystyle till facials

2 years ago

AShemaleTube

fetish, bondage, dogging, latina, facial, gangbang, group
06:26

Tanned shemale with high heel boots punishes a dude with her

2 years ago

xHamster

heels, boots, big cock, orgy
07:13

One blonde and two brunette shemale punishers spank and fuck

2 years ago

xHamster

group, shemale, bondage, gangbang
08:14

Gorgeous shemale punisher with big tits fucks a stud until

2 years ago

xHamster

group, orgy, big cock, bondage, gangbang, BDSM
01:17

You've Been a Bad Boy Mommy Wants to Punish You

2 years ago

AShemaleTube

mom, stockings, crossdresser, big cock, femboy
05:05 82%

Trans in chastity punished and anal fucked

2 years ago

AShemaleTube

anal, fetish, domination, chastity
06:37

Big ass shemale punisher gets sucked before fucking a tied up dude

2 years ago

AShemaleTube

group, shemale fucks guy, domination, gangbang, tied
19:08 77%

Frenchbaguettes Yaya The Punisher

3 years ago

TXXX

shemale fucks guy
09:41 75%

Cute Crossdressing Sissy Gets Caught And Punished

3 years ago

ShemaleZ

cute, crossdresser, caught, sissy
15:01 57%

Bdsm Transgirl Lactation Rough Punishment Homonate Puffy breasts she-male

3 years ago

ShemaleTaxi

lactating
07:29

Hard Punishment And Sex. Kitsyme0w

3 years ago

GetTranny

bondage, spanking
05:59

Trucker punishing a sissy hard

3 years ago

TrannyGem

sissy
23:53 77%

Mommy Dom Jessica Bloom Babies And Punishes Bratty Girl Jenby (short Version) 24 Min

3 years ago

ShemaleZ

mom, BDSM, shemale and girl, fetish
23:50 20%

Doc punishing his bratty submissive femboy sissy Michele

3 years ago

xHamster

black, interracial, big cock, BBC, sissy, femboy
07:29

Chubby Trans Bombshell Punishes A Dude On Cam

3 years ago

TXXX

chubby, domination, shemale fucks guy
05:00 73%

Sissy Husband Gets Caught Crossdressing and Punished

4 years ago

TrannyOne

husband, caught, sissy
08:00

Alana Ferreira Punishing A Guy Outdoors

4 years ago

GetTranny

pissing, femdom, bondage, outdoor, BDSM, shemale fucks guy
04:52 67%

Blonde TS Foxxy Punishes Slob Boyfriend With Spanking And Nonstop Pounding

4 years ago

BeMyHole

latex, tattoo, spanking, boyfriend
32:29

Sexy trans student Andrea will be punished

4 years ago

xHamster

student
08:01 60%

MATURE CROSSDRESSER TVROSE COCK, BALLS AND ASS PUNISHED

4 years ago

TrannyOne

mature, crossdresser, amateur, 18
07:12 79%

Sissy Is punished By daddy With a spanking paddle Followed by a Deep Throat Fucking

4 years ago

ShemaleTaxi

spanking, femboy, sissy, crossdresser
28:45 67%

A Private Punishment

4 years ago

TrannyOne

femdom, hardcore
06:41

Teacher Tranny Spanking Guy and Fucking His Ass in Classroom

4 years ago

TrannyOne

spanking, teacher
06:01 77%

Asian MILF shemale stepmom punish fucks faggott stepson

4 years ago

TrannyOne

stepmom, skinny, asian
43:35

Corporal Punishment Session with Mistress Jamie & Diaper Sis

4 years ago

TrannyOne

femdom, diaper
07:03

A Private Punishment With Natalie Mars

4 years ago

ShemaleZ

fisting
11:09

Korra Del Rio Penalizes TRANSSEXUAL Schoolgirl Sarina Havok With Her Rod

5 years ago

TrannyGem

femdom, lesbian, gagging, boots, teacher, slut, skirt
04:10 73%

TRANSSEXUAL College Girl Predominates Classmate (Lena Kelly)

5 years ago

TrannyGem

femdom, fetish, BDSM, facial, college, hardcore
16:47 60%

Shemale punishers indoors gangbang

5 years ago

BeMyHole

latex, bondage, boots, dogging, tied, gangbang, group
43:22 85%

Japanese Punishment And Hardcore Threesome Sex

5 years ago

HClips

handjob, threesome, asian, japanese, hardcore, amateur
18:00 46%

Bad Girl Punished After School

6 years ago

xHamster

BDSM, shemale and girl
08:11 69%

Cougar tranny mom in law punishing lazy teeanger

6 years ago

VideoSection

mom, cougar
06:29

White Gardenia Bondage Clip 4 Crossdressing Submissive Male Forced To Dress Like a Female Slut Ass Licking Punishment

6 years ago

TrannyOne

feet, bondage, crossdresser, dress
29:38 83%

Mara Nova and Sydney Farron In Punishment by Principal

6 years ago

TrannyOne

facial
04:46

Stunning latex ts gives corporal punishment

7 years ago

ShemaleZ

latex, domination
05:10 60%

Roommate punished and made love by tranny

7 years ago

Analdin

ebony, domination, ladyboy
05:40

Naughty Nina Punished by Mistress Meena

7 years ago

ShemaleZ

femdom
09:28 79%

Redhead TGirl Slut Handcuffed Spanked Whipped in Garden by Leather Clad Guy

7 years ago

TrannyGem

public, fetish, bondage, BDSM, redhead, spanking, leather
08:01 75%

MIlf Shemale Mother in Law Punishing Lazy Teeanger

7 years ago

TrannyGem

mom, feet, teen (18+), massage, fetish, MILF, dogging
06:28

Pimp and prostitute-shemale punished prostitute

8 years ago

xHamster

prostitute
08:33 69%

Crossdresser Mistress Luci May punishes spanks blonde tranny maid tight ass

9 years ago

AShemaleTube

femdom, maid, spanking, tight
05:20

Sissy katelyn drinks her own piss sissy punishment

9 years ago

TXXX

pissing
04:00

Busted Watching Porn at Work Boss Punishes Bad Employee w Her Own Cock

12 years ago

TXXX

boss
05:08

Chelsea Marie Ass fucking Pegging Session

3 months ago

Analdin

creampie, feet, domination, BDSM, femdom, chastity
05:11

Latex TS sub chastity and butt fucking sex

3 months ago

Analdin

shemale and girl, bondage, BDSM, chastity, latex
05:09

T-girl Surprise In Spooky Cemetery Sex

4 months ago

Analdin

shemale, BBW, surprise
05:09

Leather T-girl Suspension and Pegging

5 months ago

Analdin

femdom, blowjob, bondage, BDSM, facesitting, shemale and girl, leather
05:09 57%

Bound TS Honey Dominates With Huge Knob

5 months ago

Analdin

hardcore, bondage, BDSM
05:09

Blindfolded tied up man fucked by TS

8 months ago

TrannyGem

facesitting, bondage, ladyboy, footjob, tied
04:06 85%

TS Domina in Latex Fucks Dude

2 years ago

PornGem

femdom, latex, domination
05:06

Blindfolded maid is punished by tranny

5 months ago

Analdin

blowjob, bondage, femdom, domination, maid, latex
14:14

Mrs Samantha Punishes Her Slave Tgirl Marina with a Good Spank and Teases Her

1 year ago

$$ FapHouse

blonde, BDSM, sissy, mature, dutch
08:11

Milf transgender princess m. in law punishing lazy teeanger

2 weeks ago

ShemaleMovie

teen (18+), shemale fucks guy
29:23

Hijab Shemale Punishes her Asshole With a Big Dildo

1 month ago

AShemaleTube

arab, shemale, dildo
01:20

Rika Fox gets punished and takes a MASSIVE facial

1 month ago

AShemaleTube

cumshot, facial
01:25

Sexy Young TS Rika Fox gets Punished #9 full video available now for only 4.99

1 month ago

AShemaleTube

homemade, shemale and girl, cumshot

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