SHEMALE • BOSS 3,423 videos

Popular Latest Top rated

06:31 75%

Dillon Diaz gets sexual punshment from transgender boss

2 years ago

AShemaleTube

boss
05:35 62%

She-male secretary buttfuck tears up her boss

8 months ago

ShemaleTaxi

hardcore, shemale, boss, ladyboy
41:08 85%

Shemale Foxy Angel Shows Whos the Boss

6 years ago

TXXX

blowjob, fetish, boss
14:46 86%

Horny Leilani Li Sneaks Her Big Cock Inside Boss Destiny Miras Pussy

1 week ago

TheyAreHuge

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06:15 93%

Raven-haired American shemale gives bald boss a dick

6 years ago

SexVidXXX

blowjob, facial, boss, anal
07:00 73%

Her boss did not know that she is a shemale

11 years ago

AnyPorn

boss
06:15

Shemale boss sucks and fucks her intern

2 years ago

PornDr

wife, boss
06:00

Trans Maid Pleasures Her New Boss - TransRoommates

10 months ago

HotMovs

mature, boss
27:16 57%

Young Boss exposes his older secretary to a lustful slut!

4 years ago

TrannyOne

mature, secretary, slut, boss, shemale
16:28 86%

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

4 years ago

TrannyOne

maid, big cock, boss, BBC
49:49 56%

Horny latina secretary seduces and dominates her weenie boss

4 years ago

TrannyOne

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06:00 43%

Transsexual office manager got a cock bigger than her bosss

12 years ago

BravoTube

office, boss
07:59 94%

Shemale Boss Karabella Fucks And Creampies The It Guy

2 years ago

GetTranny

stockings, creampie, big ass, fetish, lingerie, tattoo, big cock
35:58 82%

Jaquelin Braxton Takes Down The Boss

6 years ago

ShemaleZ

MILF, big tits, BDSM, boss
06:25 69%

Strict boss...! Warning or swallow sperm?

1 year ago

TrannyOne

big ass, amateur, swallow, sperm, boss
41:33 74%

Shes The Boss

4 years ago

TrannyOne

shemale, office, boss
50:05 71%

Hot Latina Secretaries Abuse And Dominate Their Boss

4 years ago

TrannyOne

shemale, secretary, boss, threesome
05:35 92%

Blowing the gigantic cock of the boss to get the job - Blowjob Interview! - HQ 3D Animation

10 months ago

xHamster

3D, big cock, shemale, romanian, audition, boss
12:09 76%

Stunning Trans Boss Bangs Bbc Employee - Jade Venus

3 years ago

ShemaleZ

boss, BBC
04:01

Trans Secretary Fucks Her Boss

2 months ago

PornGem

boss, blowjob, secretary
17:08 78%

Patricia Shows Him Who Is Boss

10 months ago

AShemaleTube

shemale fucks guy, domination, shemale, blowjob, boss
48:39 81%

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

5 years ago

ShemaleZ

stockings, fetish, BDSM, domination, boss
06:16 67%

Mom intern 3some orgy with shemale boss

3 months ago

XoZilla

threesome, orgy, mature, mom, anal, boss
23:13 80%

Stockinged blonde tranny fucks and creampies her ass licking boss

8 years ago

TrannyOne

creampie, boss, anal
05:12

TS boss Marissa Minx goes raw with her employee at the office

8 months ago

AShemaleTube

shemale, office, boss
21:54 74%

Shemale Porn Video Amateur Sex My Boss Is A Transgender She Comes Home Very Angry And Fucks My...

1 year ago

TrannyOne

big cock, shemale, amateur, anal, boss
04:39 64%

Shemale boss fucks deep throat employee

6 years ago

ShemaleZ

boss
04:40 67%

Blonde Ts boss fucks redhead employee

6 years ago

ShemaleZ

boss
05:52

Im Rubbing My Dick Ifo My Hot Tgirl Boss

2 weeks ago

BeMyHole

big cock, blowjob, boss
12:50 81%

GenderXFilms - inked Trans boss Orders big black cock To Blow Her -

1 year ago

ShemaleTaxi

black, anal, big ass, blonde, big cock, ass, BBC
04:01 75%

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

3 years ago

GetTranny

casting, boss, shemale fucks guy
04:38 64%

Shemale Boss Whips And Fucks Worker

3 years ago

ShemaleZ

domination, boss
07:59

Sage Roux And Jade Venus In Hot Blonde Boss Gets Assfuced + Cum In Mouth From Horny Offices Assistant

Today

PePorn

shemale fucks guy
01:58

Hot trans girl twerking for her boss

6 days ago

AShemaleTube

big ass, solo, big cock, amateur, masturbation, shemale and girl, homemade
07:05 75%

Submit To Your Boss!

1 year ago

xHamster

mature, stockings, cumshot, boss
24:37 44%

Like a Boss

10 years ago

xHamster

boss, small tits
2:09:24 93%

Shemales bosses

6 years ago

ShemaleZ

uniform, boss, shemale, blowjob, amateur
08:04 86%

Busty Tranny Bangs Her Colleague Wet Bush and Her Boss Tight Ass at Work

5 months ago

AShemaleTube

blowjob, threesome, big cock, wet, cum in mouth, tight, boss
29:10 79%

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

1 year ago

ShemaleZ

big tits, husband, ass licking, cumshot, big cock, boss, brunette
05:03 82%

Busty TS Boss Cums On Auditioner

4 years ago

TrannyOne

boss
17:27 53%

Shemale Boss

9 years ago

TXXX

small tits, boss, shemale fucks guy
05:59 73%

My Boss Is A Transsexual!

7 years ago

ShemaleZ

domination, boss, shemale fucks guy
2:09:24 81%

Shemales bosses

6 years ago

Upornia

shemale, blowjob, boss
06:15 78%

Transgendered boss fucks her big tits secretary

11 months ago

AShemaleTube

big tits, boss, secretary
08:35 82%

The boss fucks the little trans maid

1 year ago

JizzBunker

french, bondage, maid, crossdresser, boss, solo
05:41

Boss sucks cock to transgender princess babysitter then ass fucking fucks her

9 months ago

ShemaleTaxi

shemale, boss
08:16 74%

Shemale boss Jade Venus normally does not fuck her employees

2 months ago

KeekAss

handjob, boss, blowjob, ass licking
39:33 86%

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

1 year ago

xHamster

blowjob, anal, big cock, seduced, bareback, hotel, boss
02:02

Shemale Boss Fucking A Very Annoying Coworker

13 years ago

AnyPorn

boss
12:01

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

1 year ago

AShemaleTube

boss, frottage
05:11

Nikki Vicious, the tranny boss, gets down for a serious ass pounding.

7 months ago

AShemaleTube

boss
15:03

Slutty trans sitter Avery Lust submits her tight hole to her well-endowed boss Michael Del Ray

Yesterday

XXXVogue

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21:26 86%

Young Stud Gets Stuffed By Shemale Boss Joanna Jet

1 year ago

AShemaleTube

shemale fucks guy, boss
07:00 81%

Kinky Transsexual Boss Joanna Jet Fucking Blonde Babe Sarah Vandella

11 years ago

AnyPorn

boss
25:56 75%

Big shemale shows guy whos the boss

5 years ago

ShemaleZ

redhead, boss
06:00

Angry Trans Boss Dicked Down By Clutsy Hunk Employeer - Nikki North Brody Kayman - Teaser Video

2 years ago

GetTranny

boss
05:01

BBC Boss Spanks His BIG ASS Trans Secretary.

Today

BeMyHole

boss, interracial, BBC, shemale, secretary
22:07 57%

Curvaceous double cock Latina futa dominates and fucks her boss

8 years ago

TrannyOne

domination, futanari, boss, double penetration
04:53 86%

Tranny boss goddess anal fucks employee

5 years ago

BeMyHole

boss, shemale fucks guy
05:09 62%

Blond Hair Babe Ts boss fucks redhead employee

6 years ago

XoZilla

latex, anal, fetish, bondage, BDSM, redhead, ladyboy
06:01 66%

Raunchy Slender Boss Shemale Surprised A Muscular Worker With Nataly Gold

4 years ago

HClips

18, surprise, boss
27:51

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

4 years ago

TrannyOne

office, boss
11:33

Gabriella Her boss - Gabriella Paltrova - femdom

2 months ago

ShemaleTaxi

feet, boss, facesitting
24:56 80%

TS lady boss has a new lover

14 years ago

AShemaleTube

boss
03:12

Shemale Boss Cums

13 years ago

AShemaleTube

18, cumshot, boss
08:04

TS Nicolly Pantoja and Her Boss Bareback

6 years ago

AnyPorn

boss
06:15

I finally fucked my busty ts boss asshole

1 year ago

TrannyGem

interracial, boss
43:56 86%

Secretary gets her pussy plowed by her hung tranny boss

8 years ago

TrannyOne

secretary, boss, MILF
08:00

Fuck My Boss

2 days ago

xShemaleTube

big cock
05:03

Busty TS Ginger Boss Anal Fucks Man

4 years ago

BeMyHole

redhead, boss, shemale fucks guy
06:15 80%

How about you fucking your shemale boss

3 weeks ago

AShemaleTube

shemale, anal, boss
11:50 67%

GenderX - Trans Boss Fucked in Office after Hours

5 years ago

BeMyHole

office, boss
05:59 82%

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

4 years ago

HellPorno

office, babe, secretary, boss, shemale and girl
21:22 79%

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

3 years ago

TrannyOne

wife, boss
06:24 58%

Strict boss...! Warning or swallow sperm?

2 years ago

xHamster

shemale, blowjob, sperm, swallow, boss, shemale fucks guy
13:16 86%

Big Booty Shemale Secretary Gets Fucked By Her Boss

1 year ago

ShemaleZ

secretary, big ass, shemale, boss
24:51 54%

Exciting Compilation With the Sexiest Trans Maids Enjoying Their Bosses Dicks

1 year ago

AnySex

stockings, big ass, big tits, maid, uniform, compilation, small tits
03:50

Shemale boss loves to fuck her male employees at work

5 years ago

YourLust

boss
05:26

Boss blowing man rod to shemale employee

3 years ago

ShemaleTaxi

ladyboy, facial, domination, taxi, boss
07:14 86%

Horny Secretary Inseminated By Boss!

2 years ago

ShemaleZ

stockings, secretary, boss, cumshot
01:34

Horny boss punish her employee

7 years ago

AnyPorn

boss
15:00 80%

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

3 years ago

TXXX

office, boss
05:18

Bearded masculine ass fucking fucked by she-creature boss

2 months ago

ShemaleTaxi

domination, shemale fucks guy, boss
07:06

Submit to Your Boss!

1 month ago

$$ FapHouse

masturbation, amateur, mature, boss
12:54

TRANSFIXED - Kenna James Does Whatever It Takes To Make Her Hot Trans Boss Natalie Mars Happ

3 years ago

AShemaleTube

boss
38:57 80%

Marissa Minx Transgendered Bosses

4 years ago

ShemaleZ

MILF, boss
05:42

Horny Employee And Tranny Boss

1 month ago

Fuxxx

big cock, office, boss
2:16:10 53%

Honda Momo And Momo Honda - Ktb-094 My Crossdressing Lesbian Diary With My Girlfriend When I Soiled My Pants, My Female Boss Lent Me Her Skirt... The Tingly Feel Of The Lining Of The Skirt Made Me Get An Erection And I Became A Girl And Had Lesbian S

6 months ago

ShemaleZ

shemale, lesbian, asian, crossdresser, shemale and girl, girlfriend, skirt
26:16 80%

Old boss with her tranny secretary

6 years ago

ShemaleZ

mature, creampie, fetish, outdoor, lingerie, ladyboy, uniform
05:32

Tall dominant tranny anal bangs her boss

8 years ago

TXXX

tall, boss
11:01 67%

Genderx - Man Banged By Trans Boss To Save His Job

5 years ago

TXXX

gangbang, boss
06:11

TS boss gagging on employee's dick

6 years ago

xHamster

gagging, boss
05:11 40%

Big Tittied Blonde Boss TS Dominated

11 years ago

AShemaleTube

shemale and girl, domination, boss
20:05 81%

Sexy shemale boss fuck visitor

9 years ago

DrTuber

ebony, 18, boss, shemale fucks guy, black
39:11

Shemale Porn Video Seductive Boss Chanel Santini Gives Her Employee Tony A Fuck Lesson For Being...

1 year ago

TrannyOne

shemale, boss, seduced, anal
06:15

Boss caught TS babysitter having sex in his house

Yesterday

AShemaleTube

boss
03:37

Trans Babysitter Jade Venus Jerked Off N Barebacked By Boss

3 months ago

xShemaleTube

big tits, jerking, boss
08:00

Seductive Boss Chanel Santini Gives Her Employee Tony A Fuck Lesson

1 year ago

xShemaleTube

lingerie, seduced, boss
13:07 86%

Miran’s The Boss!

3 years ago

TXXX

japanese, boss, japanese uncensored, stockings, asian, solo
07:37

Latina Trans Boss Jessy Dubai Finds Out Her Assistant Stole From Her And Dominates Her.The Big Tits Ts Facefucks Her And Fingers Her Cunt.She Bangs Her

1 year ago

BeMyHole

latina, big tits, blowjob, boss
06:14

Trans boss let client bareback her ass

3 years ago

AShemaleTube

boss
12:38

Nail me in an office uniform, Im your boss.

3 months ago

ShemaleTaxi

stockings, shemale fucks guy, crossdresser, big cock, boss, pantyhose
05:04

Shemale boss anal fucks auditioner

4 years ago

BeMyHole

redhead, short hair, office, panties, boss, stockings
06:16

Shemale Boss Fucked Her Stud Assistant

1 year ago

GetTranny

boss
05:52

Trans chick boss gives her favorite employee the best anal fuck he ever had

5 years ago

BeMyHole

teen anal (18+), nipples, boss
09:13

Ariel Demure In Dark Tgirl Roots Boss Gigantic Rod In Boar

2 years ago

TXXX

creampie, boss
04:39

Tranny boss anal fuck pervert employee

6 years ago

ShemaleZ

domination, boss
05:57

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

3 years ago

BeMyHole

stockings, fetish, lingerie, office, blonde, ass, deepthroat
06:10

T-girl nanny Jade Venus jerked off n barebacked by boss

2 years ago

TrannyOne

bareback, boss
11:39

Very freaky employee gets anally railed by his shemale boss

7 years ago

TrannyOne

boss
27:50 93%

Lady-man hammered By Boss And Secretary

6 years ago

ShemaleZ

secretary, boss, shemale
11:30 75%

Lady Boss - Boss Lady Gets More Than She Bargained For

2 months ago

ShemaleZ

stockings, ebony, big tits, creampie, shemale, boss
05:08

Asian Shemale Boss Anal Fucks Worker

3 years ago

GetTranny

boss
05:09

Sarina Dominates and Fucks Her Boss

3 weeks ago

KeekAss

fetish, anal, shemale fucks guy, boss, domination
08:00

My Transgender Boss Invites Me On A Yacht Ride And Convinces Me To Fuck Outdoors

Today

GetTranny

boss, outdoor
06:10

Big tits tgirl boss Angelina Please anal

3 years ago

TXXX

boss
26:59

Babysitter shemale fucks her boss and his friend!

4 years ago

AShemaleTube

big tits, boss
04:40

Employee anal fucks shemale boss

6 years ago

ShemaleZ

boss
06:15

Korra Del Rio Barebacking The Big Cock Boss

5 years ago

TrannyOne

boss
04:36

Ebony shemale lures her boss to suck her big Tcock in the office

5 years ago

BeMyHole

office, skirt, boss, close up

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