SHEMALE • BOSS 3,492 videos

Popular Latest Top rated

06:31 73%

Dillon Diaz gets sexual punshment from transgender boss

2 years ago

AShemaleTube

boss
06:16 57%

Do You Have A Big Swinging Dick My Boss? - Jade Venus

1 month ago

ShemaleZ

stockings, blowjob, interracial, big tits, ass licking, big cock, boss
05:35 67%

She-male secretary buttfuck tears up her boss

10 months ago

ShemaleTaxi

hardcore, shemale, boss, ladyboy
06:16 67%

Mom intern 3some orgy with shemale boss

5 months ago

XoZilla

threesome, orgy, mature, mom, anal, boss
06:15 93%

Raven-haired American shemale gives bald boss a dick

6 years ago

SexVidXXX

blowjob, facial, boss, anal
08:35 80%

The boss fucks the little trans maid

2 years ago

JizzBunker

french, bondage, maid, crossdresser, boss, solo
06:15

I finally fucked my busty ts boss asshole

1 year ago

TrannyGem

interracial, boss
10:02

Damn Maid! My Boss Almost Caught Me After Cumming

7 months ago

$$ FapHouse

maid, latina, caught, cumshot, big cock, boss
14:46 89%

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

2 months ago

TheyAreHuge

public, office, big cock, babe, BBC, boss, missionary
08:01

I walked in on my boss naked trans wife

6 months ago

SunPorno

anal, big ass, big cock, shemale, ass, boss
41:08 86%

Shemale Foxy Angel Shows Whos the Boss

6 years ago

TXXX

blowjob, fetish, boss
10:37 87%

Ebony tranny office boss fucking a dude

1 month ago

AShemaleTube

office, ebony, shemale fucks guy, homemade, boss
15:17

Hot secretary with gigantic donk wants promotion, boss

1 month ago

IcePorn

shemale, bareback, ladyboy, boss
16:28 84%

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

4 years ago

TrannyOne

maid, big cock, boss, BBC
06:08

Fucking my horny TS boss in her office

2 weeks ago

AShemaleTube

office, blowjob, boss, bareback
27:16 56%

Young Boss exposes his older secretary to a lustful slut!

4 years ago

TrannyOne

mature, secretary, slut, boss, shemale
49:49 57%

Horny latina secretary seduces and dominates her weenie boss

4 years ago

TrannyOne

secretary, boss, office, seduced
06:00 48%

Transsexual office manager got a cock bigger than her bosss

12 years ago

BravoTube

office, boss
35:58 81%

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
12:09 78%

Stunning Trans Boss Bangs Bbc Employee - Jade Venus

3 years ago

ShemaleZ

boss, BBC
07:59 95%

Shemale Boss Karabella Fucks And Creampies The It Guy

3 years ago

GetTranny

creampie, fetish, lingerie, tattoo, big cock, ass, bareback
41:33 73%

Shes The Boss

4 years ago

TrannyOne

shemale, office, boss
17:08 78%

Patricia Shows Him Who Is Boss

11 months ago

AShemaleTube

shemale fucks guy, domination, shemale, blowjob, boss
23:13 80%

Stockinged blonde tranny fucks and creampies her ass licking boss

8 years ago

TrannyOne

creampie, boss, anal
50:05 71%

Hot Latina Secretaries Abuse And Dominate Their Boss

4 years ago

TrannyOne

shemale, secretary, boss, threesome
04:01

Trans Secretary Fucks Her Boss

4 months ago

PornGem

boss, blowjob, secretary
05:35 90%

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

12 months ago

xHamster

3D, big cock, shemale, romanian, audition, 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
04:40 67%

Blonde Ts boss fucks redhead employee

6 years ago

ShemaleZ

boss
05:01

Busty trans boss Lena Kelly is anal fucked by her assis

2 weeks ago

AShemaleTube

anal, boss
10:07

Teen Whore TS Kitty In Cage Anal Destroyed By Her Boss ActorFab

4 days ago

BeMyHole

amateur, BDSM, teen anal (18+), whore, 18, bareback, beauty
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 67%

Shemale boss fucks deep throat employee

6 years ago

ShemaleZ

boss
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
02:18 83%

Shemale Boss PMV

3 months ago

AShemaleTube

blowjob, threesome, latina, compilation, group, cum in mouth, boss
29:42 50%

Ts - Maid Seduces Bosses

2 weeks ago

ShemaleZ

shemale, threesome, MILF, maid, cumshot, big cock, seduced
08:15

As your boss I think you need to fuck me

4 days ago

AShemaleTube

shemale, interracial
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
2:09:24 93%

Shemales bosses

6 years ago

ShemaleZ

uniform, boss, shemale, blowjob, amateur
05:18 84%

Ladyboy boss porks blowage employee

2 months ago

ShemaleTaxi

stockings, blowjob, domination, boss, ladyboy
08:00

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

3 weeks ago

xShemaleTube

bareback, shemale fucks guy, cum in mouth, boss
05:03 83%

Busty TS Boss Cums On Auditioner

4 years ago

TrannyOne

boss
12:56

Demons T gals - Trans babysitter Aubrey Kate Gets Assfucked By Her Boss For Some Extra Cash

1 year ago

ShemaleTaxi

money, facesitting, skirt, boss
05:22

Bbc shemale fucks handcuffed boss

3 weeks ago

PornGem

domination, ebony, bondage, big cock, boss
09:37

Dream LatinTranny serving her boss like perfect subwhore

5 days ago

AShemaleTube

amateur, interracial
06:15

Lola Morena getting disciplined by her sexy hot boss Ana Foxx

3 days ago

AShemaleTube

big cock
05:41

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

11 months ago

ShemaleTaxi

shemale, boss
05:18 67%

Bearded masculine ass fucking fucked by she-creature boss

4 months ago

ShemaleTaxi

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

How about you fucking your shemale boss

2 months ago

AShemaleTube

shemale, anal, boss
24:37 44%

Like a Boss

11 years ago

xHamster

boss, small tits, blowjob
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
08:04 86%

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

7 months ago

AShemaleTube

blowjob, threesome, big cock, wet, cum in mouth, tight, boss
2:09:24 81%

Shemales bosses

6 years ago

Upornia

shemale, blowjob, boss
05:07

Stunning Shemale Boss Fucking Worker

3 years ago

GetTranny

boss
03:12

Shemale Boss Cums

13 years ago

AShemaleTube

18, cumshot, boss
06:15 78%

Transgendered boss fucks her big tits secretary

1 year ago

AShemaleTube

big tits, boss, secretary
19:02 94%

Spray it all over my face boss

1 year ago

TrannyOne

shemale, big cock, boss
13:13

Pool Boy Came In Save His Shemale Boss

1 week ago

AShemaleTube

blowjob, boss
02:02

Shemale Boss Fucking A Very Annoying Coworker

13 years ago

AnyPorn

boss
27:51

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

4 years ago

TrannyOne

office, boss
06:15

Big boobs curvy Asian ladyboy pounded by BWC boss in her office

5 days ago

AShemaleTube

big ass, shemale, interracial, big cock, office, bareback
04:53 86%

Tranny boss goddess anal fucks employee

5 years ago

BeMyHole

boss, shemale fucks guy
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
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
06:01 67%

Raunchy Slender Boss Shemale Surprised A Muscular Worker With Nataly Gold

4 years ago

HClips

18, surprise, boss
12:54

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

3 years ago

AShemaleTube

boss
06:10

Big tits shemale Jamie Page anal rides on her boss his dick

12 years ago

AShemaleTube

riding, boss
05:12

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

10 months ago

AShemaleTube

shemale, office, boss
05:09 63%

Blond Hair Babe Ts boss fucks redhead employee

6 years ago

XoZilla

latex, anal, fetish, bondage, BDSM, redhead, ladyboy
05:03 80%

Busty TS Ginger Boss Anal Fucks Man

4 years ago

BeMyHole

redhead, boss, shemale fucks guy
05:11

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

8 months ago

AShemaleTube

boss
06:00

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

2 years ago

GetTranny

boss
25:56 75%

Big shemale shows guy whos the boss

5 years ago

ShemaleZ

redhead, boss
22:07 57%

Curvaceous double cock Latina futa dominates and fucks her boss

8 years ago

TrannyOne

domination, futanari, boss, double penetration
24:56 80%

TS lady boss has a new lover

14 years ago

AShemaleTube

boss
06:14

The end of a work week with big titty boss Binxi Banks getting some action

3 days ago

XXXVogue

shemale, shemale fucks guy, sissy, british, stockings
08:15

Butler serves busty shemale boss in every way including anal

10 months ago

AShemaleTube

shemale, big cock, boss, big tits
05:26

Boss blowing man rod to shemale employee

3 years ago

ShemaleTaxi

ladyboy, facial, domination, taxi, boss
08:06

Guy Fucks Trans Boss To Save His Job With Pierce Paris And Marissa Minx

2 months ago

ShemaleZ

ass, boss
05:39

Safada Couldnt Resist The Boss (complete In Red)

3 days ago

BeMyHole

creampie, cumshot, amateur
11:50 67%

GenderX - Trans Boss Fucked in Office after Hours

5 years ago

BeMyHole

office, boss
05:59 83%

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

5 years ago

HellPorno

office, babe, secretary, boss, shemale and girl
03:50

Shemale boss loves to fuck her male employees at work

5 years ago

YourLust

boss
12:09

Wild office boss Harinni goes crazy and obliterates a huge dildo with her sharp high heels, taking it deeper inside

3 days ago

XXXVogue

black, boss, sissy, japanese, dildo, huge dildo, footjob
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
43:56 86%

Secretary gets her pussy plowed by her hung tranny boss

8 years ago

TrannyOne

secretary, boss, MILF
21:22 79%

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

3 years ago

TrannyOne

wife, boss
05:11 40%

Big Tittied Blonde Boss TS Dominated

11 years ago

AShemaleTube

shemale and girl, domination, boss
15:39 80%

TRANSFIXED - T-Girl Lola Morena DISCIPLINED By Femdom Boss Ana Foxxx After Office Mishap!

4 days ago

SomePorn

creampie, ebony, femdom, hairy, shemale
2:16:10 51%

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

7 months ago

ShemaleZ

shemale, lesbian, asian, crossdresser, shemale and girl, girlfriend, skirt
06:24

Trans sitter buttfuck drilled while her boss is out

2 days ago

ShemaleTaxi

shemale, shemale fucks guy
06:15

Sexy hot boss Ana Foxx disciplining her employee Lola Morena

3 days ago

AShemaleTube

big cock
38:57 80%

Marissa Minx Transgendered Bosses

4 years ago

ShemaleZ

MILF, boss
13:07 86%

Miran’s The Boss!

3 years ago

TXXX

japanese, boss, japanese uncensored, stockings, asian, solo
26:16 79%

Old boss with her tranny secretary

6 years ago

ShemaleZ

mature, creampie, fetish, outdoor, lingerie, ladyboy, uniform
05:04

Shemale boss anal fucks auditioner

5 years ago

BeMyHole

redhead, short hair, office, panties, boss, stockings
05:32

Tall dominant tranny anal bangs her boss

8 years ago

TXXX

tall, boss
11:39

Very freaky employee gets anally railed by his shemale boss

7 years ago

TrannyOne

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

7 years ago

xHamster

gagging, boss
08:16 76%

Shemale boss Jade Venus normally does not fuck her employees

4 months ago

KeekAss

handjob, boss, blowjob, ass licking
05:57 67%

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

3 years ago

BeMyHole

stockings, fetish, lingerie, office, blonde, ass, deepthroat
20:05 81%

Sexy shemale boss fuck visitor

9 years ago

DrTuber

ebony, 18, boss, shemale fucks guy, black
07:14 86%

Horny Secretary Inseminated By Boss!

2 years ago

ShemaleZ

stockings, secretary, boss, cumshot
13:16 88%

Big Booty Shemale Secretary Gets Fucked By Her Boss

1 year ago

ShemaleZ

secretary, big ass, shemale, boss
06:24

Huge-boobed tequila t-girl Demi D hottest sucking and analed by boss

10 months ago

ShemaleTaxi

anal, boss
05:52

Im Rubbing My Dick Ifo My Hot Tgirl Boss

2 months ago

BeMyHole

big cock, blowjob, boss
09:13 67%

Ariel Demure In Dark Tgirl Roots Boss Gigantic Rod In Boar

2 years ago

TXXX

creampie, boss
05:47

Michael Del Ray, Natalie Stone And Big Boss - Trans Maid Is Impressed By Boss Big Cock

1 month ago

ShemaleZ

big cock, small cock, 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
06:25 60%

Tgirl4You.com - Trans nanny Gaby B rectal screws her boss

1 month ago

ShemaleMovie

shemale fucks guy, blowjob, shemale, boss, handjob, kissing
04:39

Tranny boss anal fuck pervert employee

6 years ago

ShemaleZ

domination, boss
05:28

Shemale chef assfuck plumbs trussed boss

3 years ago

ShemaleTaxi

blowjob, bondage, domination, boss
06:16

Worker porks bosses transgender wifey after cornering him with evidence

4 days ago

KeekAss

shemale, wife
04:40

Employee anal fucks shemale boss

6 years ago

ShemaleZ

boss
06:25

Bubble bootie Thai femboy teenage Boss POV handjob and big ass porking

4 days ago

ShemaleMovie

big ass, shemale fucks guy, femboy, handjob, POV, ladyboy
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

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