SHEMALE • BOSS 2,757 videos

Popular Latest Top rated

20:11 94%

TRANSSEXUAL Lena Kelly Gets Vengeance on Porno Managers Cornhole

3 years ago

TrannyGem

femdom, bondage, babe, ass, reality, boss
27:50 93%

Lady-man hammered By Boss And Secretary

4 years ago

ShemaleZ

secretary, boss
06:15 92%

Mesmerizing Natalie Mars fucks in sexy stockings with boss

3 years ago

AShemaleTube

cum in mouth, boss
06:15 92%

Raven-haired American shemale gives bald boss a dick

5 years ago

SexVidXXX

blowjob, facial, boss
08:00 91%

Heteroflexible - Cute Femboy Maid Katie Lingeries Tight Ass Gets Used By Straight Boss Mateo Tomas

2 months ago

GetTranny

stockings, maid, facial, old and young (18+), bareback, boss, cosplay
12:09 90%

Trans Maid Cant Resist Bosses Dick Micheal - Natalie Stone And Del Ray

2 years ago

HClips

stockings, small cock, maid, boss
27:33 89%

Fuck My Boss

3 years ago

BeMyHole

beauty, dogging, ass licking, shaving, slut, boss
22:11 88%

Here we enjoy Boss again getting banged

3 years ago

ShemaleZ

creampie, asian, boss
06:16 88%

Ladyboy amateur teen beauty Boss anal fucked bareback after pecker sucking

2 years ago

TrannyOne

teen (18+), teen anal (18+), boss
06:15 88%

Secretary ladyboy with big tits Tata pleases her boss with anal sex

3 years ago

TXXX

teen (18+), teen anal (18+), ladyboy, secretary, boss
01:11 87%

Big Boss Becomes Dungeon Anal Whore With Corbin Dallas And Jessica Fox

2 years ago

Upornia

stockings, whore, boss
41:33 87%

Shes The Boss

2 years ago

TrannyOne

shemale, office, boss
13:07 85%

Miran’s The Boss!

1 year ago

TXXX

japanese, boss, japanese uncensored
21:22 85%

TS Taboo #2: My Boss Wife: Aubrey Kate and Ruckus

2 years ago

TrannyOne

wife, boss
15:00 84%

TRANSFIXED - OFFICE MS. CONDUCT - Hot Trans Boss Jade Venus And Jane Wilde Fuck In Front Of The Staff!

1 year ago

TXXX

office, boss
13:04 83%

DEVILS T GIRLS - Trans Babysitter Aubrey Kate Gets analed By Her boss For Some additional Cash

1 year ago

ShemaleTaxi

money, facesitting, shemale and girl, taxi, skirt, boss
12:06 83%

Threesome Orgy With Trans Nurse and Her mommy Boss - LeWood

1 year ago

XoZilla

mom, nurse, riding, 69, orgy, boss
23:13 83%

Stockinged blonde tranny fucks and creampies her ass licking boss

6 years ago

TrannyOne

creampie, boss
41:08 83%

Shemale Foxy Angel Shows Whos the Boss

4 years ago

TXXX

blowjob, fetish, boss
12:48 82%

BBC guy fucks latina trans boss for promotion

8 months ago

AnySex

big ass, interracial, latina, office, BBC, boss
48:39 82%

Shiri Allwood - Getting Ahead: Shiri Allwood Owns Her Boss, Dale Savage With Her Cock

3 years ago

ShemaleZ

stockings, fetish, BDSM, domination, boss
17:36 82%

Sexy maid trying to satisfy her bosses

4 years ago

TXXX

maid, shemale and girl, boss
05:58 82%

Teen Maid Kate Zoha Gets Taken By Her Trans Boss : Part 2

1 year ago

TrannyOne

teen (18+), teen anal (18+), maid, boss
04:41 80%

Ts Atorney With Big Cock Fuck Milf Boss - Venus Lux

2 years ago

ShemaleZ

MILF, shemale and girl, boss
07:00 80%

Kinky Transsexual Boss Joanna Jet Fucking Blonde Babe Sarah Vandella

10 years ago

AnyPorn

boss
06:15 79%

Secretary ladyboy with big tits Tata anal pleases her boss

3 years ago

xHamster

teen (18+), teen anal (18+), ladyboy, secretary, boss
16:28 79%

Sexy tranny maid treats her boss with her BBC deep in his ass

2 years ago

TrannyOne

maid, big cock, boss
20:05 79%

Sexy shemale boss fuck visitor

8 years ago

DrTuber

ebony, 18, boss, shemale fucks guy
23:42 79%

The Boss Adam With Erica Cherry And Sabina Steele

1 year ago

ShemaleZ

threesome, boss
35:58 79%

Jaquelin Braxton Takes Down The Boss

5 years ago

ShemaleZ

MILF, big tits, BDSM, boss
15:13 78%

Sissy Crossdresser Is Todays Maid Getting Fucked By Her House Boss In The Ass

2 years ago

Upornia

asian, maid, crossdresser, sissy, boss
14:46 77%

Doctor Boss

4 years ago

TXXX

doctor, boss
05:59 76%

My Boss Is A Transsexual!

5 years ago

ShemaleZ

domination, boss
2:09:24 72%

Shemales bosses

4 years ago

Upornia

shemale, blowjob, boss
05:41 72%

Horny Boss Asslicks And Barebacks The Blonde Tgirl - Emma Rose

2 years ago

TXXX

small cock, ass licking, boss
20:22 72%

Nina Lawless Xxx - Nina Lawless - Smoking Boss Bitch

2 years ago

ShemaleZ

smoking, boss
05:45 68%

Busty Shemale Boss Gets Her Ass Licked And Barebacked By Bbc

2 years ago

ShemaleZ

amateur, interracial, BBC, boss
05:08 67%

Crossdresser takes trannys chopper up his rear end

4 years ago

XoZilla

maid, uniform, boss
26:16 65%

Old boss with her tranny secretary

4 years ago

ShemaleZ

mature, fetish, outdoor, lingerie, uniform, ass to mouth, secretary
05:50 65%

Johanna Badine In Latin Milf Shemale Sucked Off And Anals Boss

10 months ago

ShemaleZ

mature, mature anal, boss
06:24 64%

Strict boss...! Warning or swallow sperm?

5 months ago

xHamster

shemale, blowjob, sperm, swallow, boss
05:59 63%

Tranny boss ass fucks blonde girl on her first day at the job

3 years ago

HellPorno

office, babe, secretary, boss
06:01 63%

Raunchy Slender Boss Shemale Surprised A Muscular Worker With Nataly Gold

2 years ago

HClips

18, surprise, boss
22:07 62%

Curvaceous double cock Latina futa dominates and fucks her boss

6 years ago

TrannyOne

domination, futanari, boss, double penetration
41:33 61%

Shes The Boss Kenna James and shemale

3 years ago

Analdin

office, babe, erotic, boss, romantic
06:56 59%

Horny Secretary Inseminated By Boss!

4 months ago

BeMyHole

mature, german, mature anal, anal, secretary, boss
27:16 58%

Young Boss exposes his older secretary to a lustful slut!

2 years ago

TrannyOne

mature, secretary, slut, boss
39:55 57%

Horny boss gets his old fat ass banged hard by the horny TS secretary

2 years ago

TrannyOne

fat, office, secretary, boss
26:29 56%

Riley Storm Assistant Pummel

3 years ago

TrannyGem

creampie, office, old and young (18+), secretary, boss
42:51 56%

Horny latina secretary gives it to her boss good and hard

2 years ago

AShemaleTube

homemade, secretary, domination, webcam, boss, shemale fucks guy
17:27 55%

Shemale Boss

8 years ago

TXXX

small tits, boss
55:22

Lesbian training by female boss and used as a toy

7 months ago

JizzBunker

shemale, lesbian, train, japanese, boss, japanese lesbian
39:33

TRANS ANGELS - Seductive Boss Chanel Santini Gives Her Employee Tony A Fuck Lesson For Being Naughty

2 months ago

xHamster

blowjob, big cock, seduced, boss
05:12

Black Secretary Makes Her Boss Lick Her butt hole - female domination

3 weeks ago

ShemaleTaxi

black, facesitting, domination
05:06

Blonde trans anal fucks bound boss in hairy ass

1 week ago

KeekAss

fetish, shemale fucks guy, stockings
07:05

Submit To Your Boss!

3 months ago

xHamster

mature, stockings, cumshot, boss
29:10

Michael Del Ray, Del Ray And Domino Presley In Goes To Her Husbands Boss And Fucks Him To Let Her Husband Go Home Early

3 months ago

ShemaleZ

shemale, big tits, husband, ass licking, cumshot, big cock, boss
17:19

Slim ladyboy maid tops her boss

2 years ago

AShemaleTube

maid, uniform, boss, shemale fucks guy
05:50

Trans Babysitter Mia Davina Anal By Boss 6 Min

1 week ago

ShemaleZ

masturbation, big cock, handjob, small cock
20:20

Hot BDSM Boss Plugs and Disciplines Bimbo Secretary for Mistakes

2 years ago

PornHub

train, fetish, bondage, BDSM, babe, secretary, slut
12:44

Trans Maid Cant fight back Bosses man meat - Natalie Stone, Micheal DelRay - GenderXFilms

1 week ago

ShemaleMovie

shemale fucks guy, anal, missionary, maid
43:56

Secretary gets her pussy plowed by her hung tranny boss

6 years ago

TrannyOne

secretary, boss
12:47

Hot Trans Couple Spitroast Hunk Boss - Jade Venus, Kasey Kei - GenderXFilms

1 month ago

PornHub

threesome, boss
05:09

Blond Hair Babe Ts boss fucks redhead employee

4 years ago

XoZilla

latex, anal, fetish, bondage, BDSM, redhead, ladyboy
13:53

Mateo Tomas - Heteroflexible - Cute Femboy Maid Katie Lingeries Tight Ass Gets Used By Straight Boss

3 months ago

ShemaleZ

cute, shemale, maid, boss, femboy
07:14

Horny Secretary Inseminated By Boss!

5 months ago

ShemaleZ

stockings, secretary, boss
49:49

Horny latina secretary seduces and dominates her weenie boss

2 years ago

TrannyOne

secretary, boss
05:05

Secretary fucking with boss in lingerie sex

4 years ago

ShemaleZ

lingerie, secretary, boss
16:02

Dominated By My Female Boss - Indonesian Femdom With Awek Melayu

3 months ago

ShemaleZ

femdom, indonesian, boss
12:41

Trans Babysitter Aubrey Kate Gets Assfucked By Her Boss For Some Extra Cash

1 year ago

BeMyHole

handjob, beauty, blowjob, money, big tits, dogging, facesitting
04:38

Shemale Boss Whips And Fucks Worker

1 year ago

ShemaleZ

domination, boss
05:18

Sapphic boss ass fucking nails bent over employee

3 weeks ago

ShemaleTaxi

domination, BDSM, strapon, bondage, spanking
24:51

Exciting Compilation With the Sexiest Trans Maids Enjoying Their Bosses Dicks

4 months ago

AnySex

stockings, big ass, big tits, maid, compilation, boss
03:03

Shemale gets fucked by her boss during a family affair in the office

3 months ago

JizzBunker

office, cartoon, boss
21:26

Young Stud Gets Stuffed By Shemale Boss Joanna Jet

1 month ago

AShemaleTube

shemale fucks guy, boss
29:28

Indian Boss Fucked Hot Shemale

11 months ago

xHamster

indian, anal, big ass, asian, ladyboy, boss
12:09

Stunning Trans Boss Bangs Bbc Employee - Jade Venus

1 year ago

ShemaleZ

boss, BBC
24:30

Boss Overallsandacreampie

3 years ago

ShemaleZ

ladyboy, boss
12:00

Hottest Tattooed Trans Boss Gets Her Tight Ass Banged By The New Intern - Nadia Love

1 week ago

ShemaleZ

shemale, shemale fucks guy, big tits, big ass
12:26

Security Caught Boss Fucking New Hire In Elevator & Wanna Join Them With Kasey Kei And Izzy Wilde

3 months ago

ShemaleZ

shemale and girl, caught, boss
04:01

Ts Boss Fucks Him Hard And Fast In The Back Room - Melanie Brooks And Brook S

1 year ago

GetTranny

casting, boss
26:13

Boss Spurtingcumshotandcreamyhole

3 years ago

Upornia

asian, ladyboy, boss
09:06

Sissy Secretary Seduces Boss

3 years ago

xHamster

secretary, sissy, boss
04:40

Blonde Ts boss fucks redhead employee

4 years ago

ShemaleZ

boss
21:00

Secret sheboy Secretary Opens pleasant butt For Boss

5 years ago

ShemaleZ

secretary, boss
08:35

The boss fucks the little trans maid

2 months ago

JizzBunker

french, bondage, maid, crossdresser, boss
05:57

TS Izzy Wilde Barebacks Coworker As Boss Fucks Her In 3some

1 year ago

BeMyHole

stockings, fetish, lingerie, office, blonde, ass, deepthroat
15:48

Transex secretary giving it to her boss

1 week ago

XXXDan

shemale, blowjob, anal, cumshot
06:15

Tgirl4You.com - Ebony shemale babysitter Sheba Star anal fucked by her boss

7 months ago

AShemaleTube

ebony, boss
12:46

Babysitter Luna Love Fucks Divorced Boss - GenderX

3 years ago

xHamster

teen anal (18+), boss
2:09:24

Shemales bosses

4 years ago

ShemaleZ

uniform, boss
24:37

Like a Boss

9 years ago

xHamster

boss
05:18

Employee Sucks Off Her Boss Massive tranny salami For Promotion

3 years ago

HDSex

boss
06:15

Trans maid throating her boss cock before riding it

6 days ago

TXXX

shemale, stockings
12:01

DEVILS TGIRLS - Hottest Tattooed Trans Boss Nadia Love Gets Her Tight Ass Banged By The New

3 months ago

AShemaleTube

boss, frottage
28:42

Boss has her cute tranny ass fucked

3 years ago

ShemaleZ

POV, boss
03:50

Shemale boss loves to fuck her male employees at work

3 years ago

YourLust

boss
06:15

Lesbian tgirl waitress fucks her colleague after boss goes away

2 weeks ago

TXXX

fetish, lesbian
04:58

Ginger Tranny boss seduced her worker

6 months ago

TrannyOne

seduced, boss
09:13

Ariel Demure In Dark Tgirl Roots Boss Gigantic Rod In Boar

8 months ago

TXXX

creampie, boss
24:03

Transgendered Bosses 3 With Dillon Diaz And Gracie Jane

1 year ago

Upornia

stockings, fetish, big tits, lingerie, blonde, boss
05:09

Corrupted shemale agent fucks guy

3 years ago

BeMyHole

femdom, office, boss
30:44

Sissy secretary lunchtime fucking by boss

4 years ago

ShemaleZ

secretary, sissy, boss
04:49

Sissy secretary used by her boss

4 years ago

ShemaleZ

secretary, sissy, boss
06:40

Security Guard Seducing His Hot Shemale Boss

5 days ago

GetTranny

boss, shemale
06:31

Dillon Diaz gets sexual punshment from transgender boss

4 months ago

AShemaleTube

boss
12:21

Big Cocks Boss Janie Blade Bangs Employee

1 year ago

BeMyHole

handjob, redhead, dogging, tattoo, ass licking, glasses, riding
15:10

Transfixed - OFFICE MS. CONDUCT - super hot Trans boss Jade Venus And Jane Wilde Fuck In Front Of The Staff!

1 year ago

ShemaleTaxi

office, taxi, boss, shemale and girl
04:42

Ts Atorney Fucking Busty Blond Boss 5 Min

1 year ago

Upornia

boss
50:05

Hot Latina Secretaries Abuse And Dominate Their Boss

2 years ago

TrannyOne

shemale, secretary, boss
27:51

The naughty TS assistant pleases her boss by banging his juicy butthole deep and hard

2 years ago

TrannyOne

office, boss
05:03

Busty TS Boss Cums On Auditioner

2 years ago

TrannyOne

boss
18:27

SHEMALE BOSS FUCKS HER EMPLOYEE

2 years ago

AShemaleTube

big tits, uniform, vintage, boss, shemale fucks guy
11:50

GenderX - Trans Boss Fucked in Office after Hours

3 years ago

BeMyHole

office, boss
04:53

Tranny boss goddess anal fucks employee

3 years ago

BeMyHole

boss
06:58

Sexy secretary Kassondra Raine enjoys sex with boss tranny lady Kelli Lox

4 years ago

BravoTube

secretary, boss
04:39

Shemale boss fucks deep throat employee

4 years ago

ShemaleZ

boss
10:08

Your Work Review

3 weeks ago

TrannyGem

mature, stockings, black, crossdresser, cumshot
06:25

Teen Maid Kate Zoha Gets Taken By Her Tranny Boss

1 week ago

BeMyHole

shemale, maid, anal, blowjob, small tits
06:14

My Boss dreamed To Eat My Ass After He Took Me Shopping, I Feed His Old Ass My Ebony bumhole, Filling Up My Ebony Ass With His Tongue, And displaying My Booty At The Mall Msnovember Reality on Sheisnovember

3 weeks ago

ShemaleTaxi

ebony, black

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