SHEMALE • BOSS 2,997 videos

Popular Latest Top rated

49:49 53%

Horny latina secretary seduces and dominates her weenie boss

3 years ago

TrannyOne

secretary, boss, office, seduced
41:33 73%

Shes The Boss

3 years ago

TrannyOne

shemale, office, boss
41:08 86%

Shemale Foxy Angel Shows Whos the Boss

5 years ago

TXXX

blowjob, fetish, boss
04:01

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

2 years ago

GetTranny

casting, boss, shemale fucks guy
24:51 55%

Exciting Compilation With the Sexiest Trans Maids Enjoying Their Bosses Dicks

1 year ago

AnySex

stockings, blowjob, big ass, big tits, maid, compilation, small tits
10:32

Fetish femdom lesbian sex in office with busty blonde lesbian boss

9 months ago

xTits

black, femdom, shemale, blowjob, creampie, lesbian, fetish
04:00

Secretary with green hair plays along with shemale boss

5 years ago

PornIdXXX

secretary, boss
27:16 56%

Young Boss exposes his older secretary to a lustful slut!

3 years ago

TrannyOne

mature, secretary, slut, boss, shemale
06:31

Dillon Diaz gets sexual punshment from transgender boss

1 year ago

AShemaleTube

boss
48:39 81%

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

4 years ago

ShemaleZ

stockings, fetish, BDSM, domination, boss
23:13 79%

Stockinged blonde tranny fucks and creampies her ass licking boss

7 years ago

TrannyOne

creampie, boss, anal
35:58 81%

Jaquelin Braxton Takes Down The Boss

6 years ago

ShemaleZ

MILF, big tits, BDSM, boss
16:28 85%

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

3 years ago

TrannyOne

maid, big cock, boss, BBC
06:00 56%

Transsexual office manager got a cock bigger than her bosss

11 years ago

BravoTube

office, boss
12:09 67%

Stunning Trans Boss Bangs Bbc Employee - Jade Venus

2 years ago

ShemaleZ

boss, BBC
29:10 64%

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
07:00 71%

Her boss did not know that she is a shemale

11 years ago

AnyPorn

boss
50:05

Hot Latina Secretaries Abuse And Dominate Their Boss

3 years ago

TrannyOne

shemale, secretary, boss, threesome
04:40 78%

Blonde Ts boss fucks redhead employee

5 years ago

ShemaleZ

boss
21:54 73%

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

6 months ago

TrannyOne

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

Shemale boss fucks deep throat employee

5 years ago

ShemaleZ

boss
24:37 44%

Like a Boss

10 years ago

xHamster

boss, small tits
17:08 81%

Patricia Shows Him Who Is Boss

2 months ago

AShemaleTube

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06:15

Transgendered boss fucks her big tits secretary

3 months ago

AShemaleTube

big tits, boss, secretary
05:09

Corrupted shemale agent fucks guy

4 years ago

BeMyHole

femdom, office, boss
12:50 81%

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

7 months ago

ShemaleTaxi

black, shemale, anal, big ass, blonde, big cock, ass
2:09:24 92%

Shemales bosses

5 years ago

ShemaleZ

uniform, boss, shemale, blowjob
03:54

Trans Babysitter Ava Holt Is Tied Up And Barebacked By Boss

1 year ago

GetTranny

tied, boss, interracial
06:25 65%

Strict boss...! Warning or swallow sperm?

9 months ago

TrannyOne

big ass, amateur, swallow, sperm, boss
04:38 64%

Shemale Boss Whips And Fucks Worker

2 years ago

ShemaleZ

domination, boss
06:24

Trans nanny Itzel Saenz barebacked by boss

1 week ago

ShemaleTaxi

boss
05:03 82%

Busty TS Boss Cums On Auditioner

3 years ago

TrannyOne

boss
25:41

Horny guys fucking hot boss

5 years ago

ShemaleZ

boss
27:51

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

3 years ago

TrannyOne

office, boss
25:56

Big shemale shows guy whos the boss

4 years ago

ShemaleZ

redhead, boss
04:42

Ts Atorney Fucking Busty Blond Boss 5 Min

2 years ago

Upornia

boss
08:35 80%

The boss fucks the little trans maid

1 year ago

JizzBunker

french, bondage, maid, crossdresser, boss, solo
06:24 58%

Strict boss...! Warning or swallow sperm?

1 year ago

xHamster

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05:59 81%

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

4 years ago

HellPorno

office, babe, secretary, boss
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

12 months ago

BeMyHole

latina, big tits, blowjob, boss
02:02

Shemale Boss Fucking A Very Annoying Coworker

12 years ago

AnyPorn

boss
39:55 69%

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

3 years ago

TrannyOne

fat, office, secretary, boss
08:05

Tranny Maid Nicolly Pantoja Gets Her cornhole boned by Her lean Boss

7 months ago

HDSex

stockings, cumshot, shemale
06:01 82%

Strict Boss...! Warning Or Swallow Sperm?

11 months ago

BeMyHole

blowjob, german, short hair, sperm, swallow, cumshot, blonde
19:02 94%

Spray it all over my face boss

10 months ago

TrannyOne

shemale, big cock, boss
21:26 78%

Young Stud Gets Stuffed By Shemale Boss Joanna Jet

1 year ago

AShemaleTube

shemale fucks guy, boss
08:00 83%

Chubby TS maid caught wanking gets anal pounded by boss

3 months ago

SomePorn

chubby, maid, BBW, big tits, caught, heels
11:01

Genderx - Man Banged By Trans Boss To Save His Job

4 years ago

TXXX

gangbang, boss
06:03

She-male tempted by future boss gigantic dick fucking and cumshot

3 months ago

ShemaleTaxi

cumshot
06:15 92%

Raven-haired American shemale gives bald boss a dick

6 years ago

SexVidXXX

blowjob, facial, boss, anal
06:15

Office janitor anal fuck hes shemale boss

3 weeks ago

AShemaleTube

bareback
06:15

Tranny Pixi Lust wears a maid clothes and fuck boss

4 months ago

PornDr

anal, latina, maid
18:27 86%

SHEMALE BOSS FUCKS HER EMPLOYEE

3 years ago

AShemaleTube

big tits, uniform, vintage, boss, shemale fucks guy
05:09 65%

Blond Hair Babe Ts boss fucks redhead employee

5 years ago

XoZilla

latex, anal, fetish, bondage, BDSM, redhead, ladyboy
2:09:24 78%

Shemales bosses

5 years ago

Upornia

shemale, blowjob, boss
21:22 80%

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

3 years ago

TrannyOne

wife, boss
39:33 86%

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

1 year ago

xHamster

blowjob, big cock, seduced, boss, bareback, hotel
12:01

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

1 year ago

AShemaleTube

boss, frottage
06:15

Shemale pool cleaner fucks her hot blonde boss

3 months ago

PornGem

blowjob, shemale and girl, pool
21:00 82%

Secret sheboy Secretary Opens pleasant butt For Boss

6 years ago

ShemaleZ

secretary, boss
12:14 89%

Ana Foxxx Is Extremely Protective Of Her Boss, Which Is Why She Wont Just Let Any Random Candidate Meet Her

6 months ago

BeMyHole

ebony, beauty, interracial, ass licking, shemale and girl, secretary, domination
11:50 67%

GenderX - Trans Boss Fucked in Office after Hours

4 years ago

BeMyHole

office, boss
01:34

Horny boss punish her employee

6 years ago

AnyPorn

boss
06:15

Korra Del Rio Barebacking The Big Cock Boss

5 years ago

TrannyOne

boss
06:10

Big tits tgirl boss Angelina Please anal

3 years ago

TXXX

boss
09:13

Ariel Demure In Dark Tgirl Roots Boss Gigantic Rod In Boar

1 year ago

TXXX

creampie, boss
01:11 80%

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

3 years ago

Upornia

stockings, whore, boss, shemale fucks guy, BDSM
07:05 67%

Submit To Your Boss!

1 year ago

xHamster

mature, stockings, cumshot, boss
05:52

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

4 years ago

BeMyHole

teen anal (18+), nipples, boss
28:42

Boss has her cute tranny ass fucked

4 years ago

ShemaleZ

POV, boss, cute
05:04

Shemale boss anal fucks auditioner

4 years ago

BeMyHole

redhead, short hair, office, panties, boss, stockings
26:59

Babysitter shemale fucks her boss and his friend!

3 years ago

AShemaleTube

big tits, boss
43:56 85%

Secretary gets her pussy plowed by her hung tranny boss

7 years ago

TrannyOne

secretary, boss, MILF
03:50

Shemale boss loves to fuck her male employees at work

4 years ago

YourLust

boss
06:11

TS boss gagging on employee's dick

6 years ago

xHamster

gagging, boss
20:05 80%

Sexy shemale boss fuck visitor

9 years ago

DrTuber

ebony, 18, boss, shemale fucks guy
08:00 69%

Horny Ebony Milf Gets Fucked By Her Trans Boss In The Office - Carla Morelli

4 weeks ago

xShemaleTube

big cock, ebony, big ass, shemale, big tits, office
13:07 87%

Miran’s The Boss!

2 years ago

TXXX

japanese, boss, japanese uncensored, stockings, asian, solo
06:10

Big tits shemale boss Gracie Jane dick sucked and anal rides

2 years ago

TXXX

riding, boss
05:35

Huge-titted super-sexy ladyboy anal fucks boss

5 years ago

HDSex

boss
26:16 72%

Old boss with her tranny secretary

5 years ago

ShemaleZ

mature, creampie, fetish, outdoor, lingerie, uniform, ass to mouth
36:36 67%

Innocent intern guy gets his ass banged by the nasty shemale boss in the office

3 years ago

TrannyOne

office, boss
05:57

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

2 years ago

BeMyHole

stockings, fetish, lingerie, office, blonde, ass, deepthroat
05:32

Tall dominant tranny anal bangs her boss

7 years ago

TXXX

tall, boss
07:40

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

11 months ago

xShemaleTube

boss
32:46

Transgendered Bosses

5 years ago

Upornia

boss
09:56

I Clean Up, I Seduce My Boss And We End Up Fucking Hard

6 months ago

BeMyHole

webcam, creampie, chubby, domination, couple, boss
06:16

Sneaky masturbating MILF assistant pounded by big dick trans boss

5 days ago

AShemaleTube

blowjob
05:57

Sex And Two Busty Transsexual Boss Marissa Minx Barebacking An Employee

3 years ago

BeMyHole

office, clothed, boss
05:52

Victoria Shows Her TS Boss, Kaysei Kei A Good Time

1 month ago

BeMyHole

hardcore, feet, shemale and girl, footjob, blowjob, secretary
06:14

Trans boss let client bareback her ass

3 years ago

AShemaleTube

boss
06:15

I finally fucked my busty ts boss asshole

1 year ago

TrannyGem

interracial, boss
24:49

Huge-chested stellar brunette is my female domination boss

3 months ago

ShemaleMovie

shemale, blowjob, indian, boss
06:10

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

2 years ago

TrannyOne

bareback, boss
06:00

Teen 18+ Maid Kate Zoha Gets Taken By Her Trans Boss - TransRoomates

3 years ago

xShemaleTube

maid
10:10

Stress shemale gets analed by boss to feel relieve

1 month ago

AShemaleTube

shemale
05:58 84%

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

2 years ago

TrannyOne

teen (18+), teen anal (18+), maid, boss
04:37

Big Dick Ts Boss Fucking Employee

3 years ago

ShemaleZ

asian, boss, shemale fucks guy
04:40

Employee anal fucks shemale boss

5 years ago

ShemaleZ

boss
07:14 83%

Horny Secretary Inseminated By Boss!

1 year ago

ShemaleZ

stockings, secretary, boss, cumshot
06:16

Shemale Boss Fucked Her Stud Assistant

1 year ago

GetTranny

boss
04:41

Man employee anal banged by shemale boss

6 years ago

ShemaleZ

domination, boss
07:59 96%

Shemale Boss Karabella Fucks And Creampies The It Guy

2 years ago

GetTranny

stockings, creampie, big ass, fetish, lingerie, tattoo, big cock
06:21

Maid trans nymph barebacked by her boss

2 years ago

ShemaleMovie

maid, boss
15:35

Stacked trans secretary allows her boss to fuck her on his b-day

1 week ago

AnySex

anal, boss
07:02

Black Boss Tranny Breeding White Man

4 years ago

AShemaleTube

boss, shemale fucks guy
09:47

Thick Shemale Secretary Analed By Big Bald Boss

2 weeks ago

BeMyHole

big ass
05:26

Boss blowing man rod to shemale employee

2 years ago

ShemaleTaxi

ladyboy, facial, domination, taxi, boss
05:50

I Watch My Boss Busty Tgirl Wife Shower 6 Min

1 year ago

ShemaleZ

wife, shower, big cock, boss
05:11

Big Tittied Blonde Boss TS Dominated

10 years ago

AShemaleTube

shemale and girl, domination, boss
05:12

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

3 weeks ago

AShemaleTube

shemale, office, boss
41:33 63%

Shes The Boss Kenna James and shemale

4 years ago

Analdin

office, babe, erotic, boss, romantic
12:54

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

3 years ago

AShemaleTube

boss
05:10

Tranny boss in lingerie anal fucks employee

6 years ago

AShemaleTube

boss
27:50 96%

Lady-man hammered By Boss And Secretary

5 years ago

ShemaleZ

secretary, boss, shemale
08:15

Huge tits shemale Brittney Kade gives boss a sloppy present

1 month ago

TXXX

boss, blowjob
05:40

Who is boss?

5 months ago

ShemaleTaxi

big cock
06:00

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

1 year ago

GetTranny

boss
06:15

Leilani Li fucks her horny boss Destiny Mira blowing her mind

3 weeks ago

AShemaleTube

boss, blowjob
06:13

She-male assistant pokes Her Boss

4 years ago

VideoSection

boss

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