SHEMALE • BOSS 3,011 videos

Popular Latest Top rated

20:11 96%

TRANSSEXUAL Lena Kelly Gets Vengeance on Porno Managers Cornhole

4 years ago

TrannyGem

femdom, anal, big ass, bondage, babe, ass, reality
27:50 96%

Lady-man hammered By Boss And Secretary

5 years ago

ShemaleZ

secretary, boss, shemale
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
24:30 95%

Boss Overallsandacreampie

4 years ago

ShemaleZ

ladyboy, boss, asian, creampie, POV
26:13 94%

Boss Spurtingcumshotandcreamyhole

4 years ago

Upornia

asian, ladyboy, boss, POV
19:02 94%

Spray it all over my face boss

10 months ago

TrannyOne

shemale, big cock, boss
2:09:24 92%

Shemales bosses

5 years ago

ShemaleZ

uniform, boss, shemale, blowjob
06:15 91%

Raven-haired American shemale gives bald boss a dick

6 years ago

SexVidXXX

blowjob, facial, boss, anal
06:10 91%

Small tits trans maid Claire Tenebrarum barebacked by boss

3 years ago

AShemaleTube

maid, boss
06:15 90%

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

1 year ago

AShemaleTube

ebony, boss
05:35 90%

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

2 months ago

xHamster

3D, big cock, shemale, romanian, audition, boss
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
27:33 89%

Fuck My Boss

4 years ago

BeMyHole

beauty, dogging, ass licking, shaving, slut, boss
22:51 88%

Riley Ivy - Beautiful Trans Bareback Anal With Her New Boss

9 months ago

ShemaleZ

beauty, anal, interracial, asian, tattoo, blonde, bareback
13:04 88%

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

2 years ago

ShemaleTaxi

money, facesitting, shemale and girl, taxi, skirt, boss
22:11 87%

Here we enjoy Boss again getting banged

4 years ago

ShemaleZ

creampie, asian, boss, POV
12:06 87%

Threesome Orgy With Trans Nurse and Her mommy Boss - LeWood

2 years ago

XoZilla

mom, threesome, nurse, riding, 69, orgy, boss
06:15 87%

Mesmerizing Natalie Mars fucks in sexy stockings with boss

4 years ago

AShemaleTube

cum in mouth, boss
13:07 87%

Miran’s The Boss!

2 years ago

TXXX

japanese, boss, japanese uncensored, stockings, asian, solo
08:09 86%

Your Boss Is a Homewrecker

10 months ago

xHamster

solo, amateur, cheating, boss
07:38 86%

Bosses Stepdaughter Wants My Trans Dick

10 months ago

BeMyHole

cute, beauty, dogging, tattoo, ass licking, shemale and girl, domination
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
06:16 86%

Ladyboy amateur teen beauty Boss anal fucked bareback after pecker sucking

3 years ago

TrannyOne

teen (18+), teen anal (18+), boss, beauty, shemale
06:49 86%

Black Boss Tranny Breeding White Man

4 years ago

BeMyHole

redhead, boss, black, shemale fucks guy
41:08 86%

Shemale Foxy Angel Shows Whos the Boss

5 years ago

TXXX

blowjob, fetish, boss
12:48 86%

BBC guy fucks latina trans boss for promotion

1 year ago

AnySex

big ass, interracial, latina, office, BBC, boss
18:27 86%

SHEMALE BOSS FUCKS HER EMPLOYEE

3 years ago

AShemaleTube

big tits, uniform, vintage, boss, shemale fucks guy
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
43:56 85%

Secretary gets her pussy plowed by her hung tranny boss

7 years ago

TrannyOne

secretary, boss, MILF
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
16:58 83%

Boss futanari

5 months ago

AShemaleTube

amateur, futanari, shemale, boss
13:16 83%

Big Booty Shemale Secretary Gets Fucked By Her Boss

8 months ago

ShemaleZ

secretary, big ass, shemale
24:03 83%

Transgendered Bosses 3 With Dillon Diaz And Gracie Jane

2 years ago

Upornia

stockings, fetish, big tits, lingerie, blonde, boss
07:14 83%

Horny Secretary Inseminated By Boss!

1 year ago

ShemaleZ

stockings, secretary, boss, cumshot
07:59 83%

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

5 months ago

GetTranny

futanari, japanese, gangbang, skirt, asian
15:00 83%

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

2 years ago

TXXX

office, boss
04:53 83%

Tranny boss goddess anal fucks employee

4 years ago

BeMyHole

boss, shemale fucks guy
17:36 83%

Sexy maid trying to satisfy her bosses

5 years ago

TXXX

maid, shemale and girl, boss, threesome, amateur
08:00 83%

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
06:01 82%

Strict Boss...! Warning Or Swallow Sperm?

11 months ago

BeMyHole

blowjob, german, short hair, sperm, swallow, cumshot, blonde
04:41 82%

Ts Atorney With Big Cock Fuck Milf Boss - Venus Lux

3 years ago

ShemaleZ

MILF, shemale and girl, boss
21:00 82%

Secret sheboy Secretary Opens pleasant butt For Boss

7 years ago

ShemaleZ

secretary, boss
05:03 82%

Busty TS Boss Cums On Auditioner

3 years ago

TrannyOne

boss
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
35:58 81%

Jaquelin Braxton Takes Down The Boss

6 years ago

ShemaleZ

MILF, big tits, BDSM, 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
06:15 81%

Secretary ladyboy with big tits Tata anal pleases her boss

4 years ago

xHamster

teen (18+), teen anal (18+), ladyboy, secretary, boss
05:59 81%

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

4 years ago

HellPorno

office, babe, secretary, 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
14:46 80%

Doctor Boss

5 years ago

TXXX

doctor, boss
08:35 80%

The boss fucks the little trans maid

1 year ago

JizzBunker

french, bondage, maid, crossdresser, boss, solo
21:22 80%

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

3 years ago

TrannyOne

wife, boss
09:30 80%

Latina Trans Maid Succumbs To Boss Weenie

8 months ago

HClips

amateur, latina, big cock, boss, maid
05:09 80%

Corrupted shemale agent fucks guy

4 years ago

BeMyHole

femdom, office, boss
38:57 80%

Marissa Minx Transgendered Bosses

3 years ago

ShemaleZ

MILF, 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
20:05 80%

Sexy shemale boss fuck visitor

9 years ago

DrTuber

ebony, 18, boss, shemale fucks guy
15:10 80%

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
17:08 80%

Patricia Shows Him Who Is Boss

2 months ago

AShemaleTube

shemale fucks guy, domination, shemale, blowjob, boss
23:13 79%

Stockinged blonde tranny fucks and creampies her ass licking boss

7 years ago

TrannyOne

creampie, boss, anal
15:13 79%

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

3 years ago

Upornia

asian, maid, crossdresser, sissy, boss, teen (18+)
07:00 79%

Kinky Transsexual Boss Joanna Jet Fucking Blonde Babe Sarah Vandella

11 years ago

AnyPorn

boss
06:57 79%

Shemale Porn Video Horny Secretary Inseminated By Boss!

7 months ago

TrannyOne

shemale, german, anal, secretary
07:16 79%

Sexy Thai-khmer maid with big balls abuse her boss

3 months ago

AShemaleTube

homemade, stockings, thai, fetish, maid, ladyboy, uniform
2:09:24 78%

Shemales bosses

5 years ago

Upornia

shemale, blowjob, boss
06:15 78%

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

4 years ago

TXXX

teen (18+), teen anal (18+), ladyboy, secretary, boss, asian
21:26 78%

Young Stud Gets Stuffed By Shemale Boss Joanna Jet

1 year ago

AShemaleTube

shemale fucks guy, boss
08:01 78%

Pregnant mom and boss's daughter Step Into My Shower

3 years ago

TrannyOne

mom, pregnant, stepmom, shower, boss
06:56 77%

Horny Secretary Inseminated By Boss!

1 year ago

BeMyHole

mature, german, mature anal, anal, glasses, secretary, boss
05:41 77%

Horny Boss Asslicks And Barebacks The Blonde Tgirl - Emma Rose

3 years ago

TXXX

small cock, ass licking, boss, big cock
20:22 76%

Nina Lawless Xxx - Nina Lawless - Smoking Boss Bitch

3 years ago

ShemaleZ

smoking, boss, solo
12:41 75%

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
05:59 74%

My Boss Is A Transsexual!

6 years ago

ShemaleZ

domination, boss, shemale fucks guy
41:33 73%

Shes The Boss

3 years ago

TrannyOne

shemale, office, boss
21:54 73%

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

7 months ago

TrannyOne

big cock, shemale, amateur, anal, boss
23:42 73%

The Boss Adam With Erica Cherry And Sabina Steele

2 years ago

ShemaleZ

threesome, boss
13:00 73%

Beautiful Trans Bareback Anal with Her New Boss

10 months ago

AShemaleTube

blowjob, shemale, bareback, anal, beauty, boss
08:00 72%

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

1 month ago

xShemaleTube

big cock, ebony, big ass, shemale, big tits, office, boss
26:16 72%

Old boss with her tranny secretary

5 years ago

ShemaleZ

mature, creampie, fetish, outdoor, lingerie, uniform, ass to mouth
07:00 71%

Her boss did not know that she is a shemale

11 years ago

AnyPorn

boss
06:01 71%

Shemale maid buttfucked by tranny boss

3 years ago

TrannyOne

maid, heels, boss
50:37 71%

Horny Mature Secretary Turns Her Boss Into A Submissive Bitch

3 years ago

BeMyHole

mature anal, office, secretary, boss, shemale fucks guy
06:31 70%

Dillon Diaz gets sexual punshment from transgender boss

1 year ago

AShemaleTube

boss
04:40 70%

Blonde Ts boss fucks redhead employee

5 years ago

ShemaleZ

boss
05:50 70%

Johanna Badine In Latin Milf Shemale Sucked Off And Anals Boss

1 year ago

ShemaleZ

mature, mature anal, boss, shemale fucks guy
07:05 69%

Submit To Your Boss!

1 year ago

xHamster

mature, stockings, cumshot, 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
05:08 68%

Crossdresser takes trannys chopper up his rear end

5 years ago

XoZilla

maid, uniform, boss
05:45 68%

Busty Shemale Boss Gets Her Ass Licked And Barebacked By Bbc

3 years ago

ShemaleZ

amateur, interracial, BBC, boss
12:09 67%

Stunning Trans Boss Bangs Bbc Employee - Jade Venus

2 years ago

ShemaleZ

boss, BBC
11:50 67%

GenderX - Trans Boss Fucked in Office after Hours

4 years ago

BeMyHole

office, boss
06:18 67%

Strict Boss...! Warning Or Swallow Sperm?

1 year ago

ShemaleZ

sperm, swallow, boss
36:36 67%

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

3 years ago

TrannyOne

office, boss
05:09 65%

Blond Hair Babe Ts boss fucks redhead employee

5 years ago

XoZilla

latex, anal, fetish, bondage, BDSM, redhead, ladyboy
06:25 65%

Strict boss...! Warning or swallow sperm?

9 months ago

TrannyOne

big ass, amateur, swallow, sperm, boss
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
12:59 64%

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

3 months ago

ShemaleZ

ebony, big ass, MILF, tattoo, office, ass, boss
04:38 64%

Shemale Boss Whips And Fucks Worker

2 years ago

ShemaleZ

domination, boss
04:39 64%

Shemale boss fucks deep throat employee

5 years ago

ShemaleZ

boss
28:50 64%

Lewd Secretaries gang Up On Their penis Manager

4 years ago

TrannyGem

office, gangbang, secretary, cum in mouth, domination, penis, boss
06:01 63%

Raunchy Slender Boss Shemale Surprised A Muscular Worker With Nataly Gold

3 years ago

HClips

18, surprise, boss
05:42 63%

Tall imperious shemale rectal bangs her boss

5 years ago

HDSex

tall, domination
41:33 63%

Shes The Boss Kenna James and shemale

4 years ago

Analdin

office, babe, erotic, boss, romantic
08:12 63%

Trans Maid Pleasures Her New Boss

11 months ago

xHamster

maid, shemale, bareback, beauty, small tits
12:41 60%

Bitch Gabi serving her boss ActorFab

4 weeks ago

AShemaleTube

cumshot, amateur, big ass, bareback, lingerie, boss
41:34 60%

Thai Tranny June Gets Washed In The Shower By The Boss

3 years ago

ShemaleZ

thai, redhead, shower, boss, asian, big ass
06:24 58%

Strict boss...! Warning or swallow sperm?

1 year ago

xHamster

shemale, blowjob, sperm, swallow, boss, shemale fucks guy
22:07 57%

Curvaceous double cock Latina futa dominates and fucks her boss

7 years ago

TrannyOne

domination, futanari, boss, double penetration
16:02 57%

Dominated By My Female Boss - Indonesian Femdom With Awek Melayu

1 year ago

ShemaleZ

femdom, indonesian, boss
27:16 55%

Young Boss exposes his older secretary to a lustful slut!

3 years ago

TrannyOne

mature, secretary, slut, boss, shemale
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
06:58 55%

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

5 years ago

BravoTube

secretary, boss
42:51 54%

Horny latina secretary gives it to her boss good and hard

3 years ago

AShemaleTube

mature, homemade, secretary, domination, webcam, boss, shemale fucks guy
49:49 53%

Horny latina secretary seduces and dominates her weenie boss

3 years ago

TrannyOne

secretary, boss, office, seduced
26:29 52%

Riley Storm Assistant Pummel

4 years ago

TrannyGem

creampie, office, old and young (18+), secretary, boss
2:01:54 52%

Waaa-441 Shemale Gal Ol Gets Harassed By Kneading Her Penis! Two Slutty Bosses Train Her To Orgasm With Anal Sex! Ram Ichinose - Hatano Yui, Yui Ichinose And Otsuki Hibiki

4 months ago

ShemaleZ

shemale, train, anal, threesome, fetish, asian, orgasm
29:22 50%

Indian Boss Fucked Hot Shemale

1 year ago

ShemaleZ

indian, teen (18+), boss
17:27 50%

Shemale Boss

9 years ago

TXXX

small tits, boss, shemale fucks guy
06:26 50%

Dicky Office Girl Tata Hels Her Boss To Cum

2 years ago

DrTuber

blowjob, POV, ladyboy, office, boss, shemale and girl

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