SHEMALE • BOSS 3,423 videos

Popular Latest Top rated

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
19:02 94%

Spray it all over my face boss

1 year ago

TrannyOne

shemale, big cock, boss
24:30 94%

Boss Overallsandacreampie

4 years ago

ShemaleZ

ladyboy, boss, asian, creampie, POV, shemale
27:50 93%

Lady-man hammered By Boss And Secretary

6 years ago

ShemaleZ

secretary, boss, shemale
06:15 93%

Raven-haired American shemale gives bald boss a dick

6 years ago

SexVidXXX

blowjob, facial, boss, anal
07:19 93%

Horny secretary inseminated by the boss!

1 year ago

XXXDan

beauty, german, big tits, secretary, boss, deepthroat
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
2:09:24 92%

Shemales bosses

6 years ago

ShemaleZ

uniform, boss, shemale, blowjob, amateur
06:15 92%

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

2 years ago

AShemaleTube

ebony, boss, interracial, anal
08:14 92%

Marvelous French transsexual teen Riding Her Boss Actorfab

6 months ago

ShemaleMovie

teen (18+), shemale, french, spanking, riding, boss
20:11 92%

TRANSSEXUAL Lena Kelly Gets Vengeance on Porno Managers Cornhole

5 years ago

TrannyGem

femdom, bondage, babe, ass, reality, boss
06:10 92%

Small tits trans maid Claire Tenebrarum barebacked by boss

3 years ago

AShemaleTube

maid, boss, small cock, small tits
05:20 91%

TS atorney with immense manstick bang MILF boss

1 year ago

ShemaleMovie

shemale, blowjob, creampie, anal, MILF, BDSM, ladyboy
22:30 91%

Regina Twist Pleasing The Beautiful Trans Boss

2 years ago

ShemaleZ

ass to mouth, boss, stockings
12:09 90%

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

3 years ago

HClips

stockings, small cock, maid, boss, small tits
05:10 90%

Tranny boss in lingerie assfucking fucks employee

6 years ago

Analdin

fetish, ladyboy, office, domination, boss
22:51 90%

Riley Ivy - Beautiful Trans Bareback Anal With Her New Boss

1 year ago

ShemaleZ

beauty, anal, interracial, asian, tattoo, blonde, bareback
26:13 89%

Boss Spurtingcumshotandcreamyhole

4 years ago

Upornia

asian, ladyboy, boss, POV
09:30 89%

Latina Trans Maid Succumbs To Boss Weenie

1 year ago

HClips

amateur, latina, big cock, boss, maid
13:04 89%

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

3 years ago

ShemaleTaxi

money, facesitting, shemale and girl, taxi, skirt, boss
27:33 88%

Fuck My Boss

4 years ago

BeMyHole

beauty, dogging, ass licking, shaving, slut, boss
07:38 88%

Bosses Stepdaughter Wants My Trans Dick

1 year ago

BeMyHole

cute, beauty, dogging, ass licking, shemale and girl, glasses, boss
12:06 88%

Threesome Orgy With Trans Nurse and Her mommy Boss - LeWood

2 years ago

XoZilla

mom, threesome, nurse, riding, 69, orgy, boss
08:04 88%

Trans Maid Kaela Luna Wants to Be Used by Her New Boss

5 months ago

AShemaleTube

cumshot, shemale, maid, blowjob
08:09 88%

Your Boss Is a Homewrecker

1 year ago

xHamster

solo, amateur, cheating, boss, masturbation
08:36 88%

Japanese Boss Finds Out The Cute New Hire Has A Girly Dick, And Cums All Over It

3 years ago

ShemaleZ

cute, japanese, boss, small cock
22:11 88%

Here we enjoy Boss again getting banged

5 years ago

ShemaleZ

creampie, asian, boss, POV
06:15 88%

Mesmerizing Natalie Mars fucks in sexy stockings with boss

4 years ago

AShemaleTube

cum in mouth, boss
21:55 87%

Suckin my boss

3 months ago

AShemaleTube

ebony, shemale, 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, anal, big cock, seduced, bareback, hotel, boss
13:07 86%

Miran’s The Boss!

3 years ago

TXXX

japanese, boss, japanese uncensored, stockings, asian, solo
14:46 86%

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

1 week ago

TheyAreHuge

creampie, public, missionary, big cock, black, boss, BBC
43:56 86%

Secretary gets her pussy plowed by her hung tranny boss

8 years ago

TrannyOne

secretary, boss, MILF
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
21:26 86%

Young Stud Gets Stuffed By Shemale Boss Joanna Jet

1 year ago

AShemaleTube

shemale fucks guy, boss
13:16 86%

Big Booty Shemale Secretary Gets Fucked By Her Boss

1 year ago

ShemaleZ

secretary, big ass, shemale, boss
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
24:03 86%

Transgendered Bosses 3 With Dillon Diaz And Gracie Jane

2 years ago

Upornia

amateur, stockings, fetish, big tits, lingerie, blonde, boss
05:41 86%

Jade Venus - Maid Trans Woman Gets Her Ass Barebacked By Her Boss Big Cock

3 years ago

ShemaleZ

maid, boss
07:14 86%

Horny Secretary Inseminated By Boss!

2 years ago

ShemaleZ

stockings, secretary, boss, cumshot
04:53 86%

Tranny boss goddess anal fucks employee

5 years ago

BeMyHole

boss, shemale fucks guy
12:48 86%

BBC guy fucks latina trans boss for promotion

2 years ago

AnySex

big ass, interracial, latina, office, BBC, boss
15:10 86%

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

2 years ago

ShemaleTaxi

office, taxi, boss, shemale and girl, beauty
41:22 86%

Maid receives poked By Her Boss

6 years ago

TXXX

maid, uniform, boss
06:04 86%

Dominant Shemale Boss Fucks Favorite Employee

6 years ago

ShemaleZ

mature, boss
41:08 85%

Shemale Foxy Angel Shows Whos the Boss

6 years ago

TXXX

blowjob, fetish, boss
06:16 85%

Ladyboy amateur teen beauty Boss anal fucked bareback after pecker sucking

3 years ago

TrannyOne

teen (18+), teen anal (18+), boss, beauty, shemale, amateur
02:41 85%

Rigid3d D3d Buttercoat Intense Office Threesome: Hot Slut Fucked by Two Huge Cocks, Deep Throat & Anal with My Bosses

7 months ago

$$ FapHouse

anal, 3D, boss
28:53 84%

He Used to Be the Boss but Not Anymore

5 months ago

$$ FapHouse

mature, mature anal, ass to mouth, cum in mouth, sissy, boss, cum in ass
21:00 84%

Secret sheboy Secretary Opens pleasant butt For Boss

7 years ago

ShemaleZ

secretary, boss
17:36 84%

Sexy maid trying to satisfy her bosses

6 years ago

TXXX

maid, shemale and girl, boss, threesome, amateur, shemale
02:18 83%

Shemale Boss PMV

1 month ago

AShemaleTube

blowjob, threesome, latina, compilation, group, cum in mouth, boss
05:09 83%

Corrupted shemale agent fucks guy

5 years ago

BeMyHole

femdom, office, boss
05:07 83%

Tranny Aubrey Kate Gets Her Dick Sucked

1 year ago

BeMyHole

anal, blowjob, facial
06:49 83%

Black Boss Tranny Breeding White Man

5 years ago

BeMyHole

redhead, boss, black, shemale fucks guy
06:21 83%

Maid trans nymph barebacked by her boss

3 years ago

ShemaleMovie

maid, boss
05:25 83%

Futa-boss surprised subordinate with her big

6 years ago

AShemaleTube

futanari, surprise, boss, shemale and girl
39:05 83%

Christina Hearts - The new boss in charge

10 months ago

XXXVogue

boss, crossdresser, creampie, cumshot
04:42 83%

Ts Atorney Fucking Busty Blond Boss 5 Min

3 years ago

Upornia

boss
05:20 83%

Black TS boss ravages worker in motel

3 years ago

ShemaleTaxi

black, domination, hotel, boss
05:07 83%

Redhead boss rides prick to TS employee

5 years ago

Analdin

office, facial, riding, boss, domination
04:41 83%

Ts Atorney With Big Cock Fuck Milf Boss - Venus Lux

4 years ago

ShemaleZ

MILF, shemale and girl, boss
18:27 83%

SHEMALE BOSS FUCKS HER EMPLOYEE

4 years ago

AShemaleTube

big tits, uniform, vintage, boss, shemale fucks guy, cumshot
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
35:58 82%

Jaquelin Braxton Takes Down The Boss

6 years ago

ShemaleZ

MILF, big tits, BDSM, boss
08:35 82%

The boss fucks the little trans maid

1 year ago

JizzBunker

french, bondage, maid, crossdresser, boss, solo
05:12 82%

The filth part #2 - submissive Maid gets nailed doggystyle on balcony by her horny futa boss

2 years ago

ShemaleTaxi

public, outdoor, maid, cartoon, futanari, boss
05:03 82%

Busty TS Boss Cums On Auditioner

4 years ago

TrannyOne

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
06:15 81%

Secretary ladyboy with big tits Tata anal pleases her boss

5 years ago

xHamster

teen (18+), teen anal (18+), ladyboy, secretary, boss, cum in mouth
07:00 81%

Kinky Transsexual Boss Joanna Jet Fucking Blonde Babe Sarah Vandella

11 years ago

AnyPorn

boss
2:09:24 81%

Shemales bosses

6 years ago

Upornia

shemale, blowjob, boss
20:05 81%

Sexy shemale boss fuck visitor

9 years ago

DrTuber

ebony, 18, boss, shemale fucks guy, black
20:22 81%

Nina Lawless Xxx - Nina Lawless - Smoking Boss Bitch

3 years ago

ShemaleZ

smoking, boss, solo
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
06:57 80%

Shemale Porn Video Horny Secretary Inseminated By Boss!

1 year ago

TrannyOne

shemale, german, anal, secretary
05:18 80%

Ladyboy boss porks blowage employee

1 month ago

ShemaleTaxi

stockings, blowjob, domination, boss, ladyboy
29:17 80%

Office Milf Gets Her Pussy Fucked By Her Trans Boss With Ariel Demure And Megan Mistakes

1 month ago

ShemaleZ

shemale, shemale and girl, creampie, MILF, office
05:07 80%

Shemale anal pounds boss in Femdom

1 month ago

AShemaleTube

big cock, shemale fucks guy, shemale, femdom
06:15 80%

How about you fucking your shemale boss

2 weeks ago

AShemaleTube

shemale, anal, boss
08:16 80%

I walked in on my boss naked trans wife

4 months ago

AShemaleTube

boss, wife
38:58 80%

Jane Marie In Boss Level

4 years ago

TXXX

boss
07:59 80%

Miab-328 A Futanari Female Boss Gets Through Her Unprotected Tight Skirt That Was Turned Up By An Erection Ruisa Tsukizuki

1 year ago

GetTranny

futanari, japanese, gangbang, skirt, asian
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
06:42 80%

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

5 years ago

BeMyHole

ass to mouth, natural, dress, boss
06:11 80%

Office ladyboy tramp Tata allows Boss Too Much

6 months ago

ShemaleTaxi

pissing, shemale fucks guy, pantyhose, office, secretary, upskirt
15:10 80%

My Trans Boss Fucks Me For Being A Bad Employee - Salome Gil

2 months ago

BeMyHole

blowjob, shemale and girl, creampie, 18
06:56 80%

Horny Secretary Inseminated By Boss!

2 years ago

BeMyHole

mature, german, mature anal, anal, glasses, secretary, 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
06:00 80%

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

3 years ago

TXXX

maid, boss
38:57 80%

Marissa Minx Transgendered Bosses

4 years ago

ShemaleZ

MILF, boss
26:28 80%

Shemale Maid nailed By Her shemale Boss

6 years ago

ShemaleZ

shemale, maid, uniform, boss
24:56 80%

TS lady boss has a new lover

14 years ago

AShemaleTube

boss
26:37 80%

Brunette Asian tranny gets ordered by the boss to shove her big cock balls deep in his ass

5 years ago

BeMyHole

nipples, heels, dress, boss, kissing
26:16 80%

Old boss with her tranny secretary

6 years ago

ShemaleZ

mature, creampie, fetish, outdoor, lingerie, ladyboy, uniform
05:58 80%

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

3 years ago

TrannyOne

teen (18+), teen anal (18+), maid, boss
23:13 80%

Stockinged blonde tranny fucks and creampies her ass licking boss

8 years ago

TrannyOne

creampie, boss, anal
21:22 79%

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

3 years ago

TrannyOne

wife, boss
05:41 79%

Horny Boss Asslicks And Barebacks The Blonde Tgirl - Emma Rose

4 years ago

TXXX

small cock, ass licking, boss, big cock
08:00 79%

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

1 year ago

GetTranny

cute, stockings, maid, facial, old and young (18+), bareback, 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
12:41 79%

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

2 years ago

BeMyHole

handjob, beauty, blowjob, money, big tits, dogging, facesitting
07:16 79%

Sexy Thai-khmer maid with big balls abuse her boss

10 months ago

AShemaleTube

homemade, stockings, thai, maid, ladyboy, uniform, boss
17:08 78%

Patricia Shows Him Who Is Boss

10 months ago

AShemaleTube

shemale fucks guy, domination, shemale, blowjob, boss
08:06 78%

Beautiful Trans Bareback Anal With Her New Boss

1 year ago

ShemaleZ

tattoo, shemale, beauty, lingerie, boss
06:15 78%

Transgendered boss fucks her big tits secretary

11 months ago

AShemaleTube

big tits, boss, secretary
06:01 78%

Shemale maid buttfucked by tranny boss

4 years ago

TrannyOne

maid, heels, boss
22:38 78%

My Boss Fucks My Ass And Sucks My Cock In The Bathroom

2 years ago

ShemaleZ

cum in mouth, bathroom, boss, cum in ass
08:00 77%

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

8 months ago

xShemaleTube

ebony, shemale, big ass, MILF, big tits, office, big cock
14:46 76%

Doctor Boss

6 years ago

TXXX

doctor, boss
12:09 76%

Stunning Trans Boss Bangs Bbc Employee - Jade Venus

3 years ago

ShemaleZ

boss, BBC
11:51 75%

Perfect brunette serving her boss

3 weeks ago

AShemaleTube

boss, amateur
11:30 75%

Lady Boss - Boss Lady Gets More Than She Bargained For

1 month ago

ShemaleZ

stockings, ebony, big tits, creampie, shemale, boss
06:31 75%

Dillon Diaz gets sexual punshment from transgender boss

1 year ago

AShemaleTube

boss
12:41 75%

Bitch Gabi serving her boss ActorFab

8 months ago

AShemaleTube

cumshot, amateur, big ass, bareback, lingerie, boss
07:05 75%

Submit To Your Boss!

1 year ago

xHamster

mature, stockings, cumshot, 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
25:56 75%

Big shemale shows guy whos the boss

5 years ago

ShemaleZ

redhead, boss
13:00 75%

Beautiful Trans Bareback Anal with Her New Boss

1 year ago

AShemaleTube

blowjob, shemale, bareback, anal, beauty, boss
06:15 75%

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

5 years ago

TXXX

teen (18+), teen anal (18+), ladyboy, secretary, boss, asian

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