SHEMALE • BOSS 390 videos

Popular Latest Top rated

34:40

Hot Trans Couple Fucked And Facialed By Hunk Boss - Jade Venus, Kasey Kei

1 week ago

BeMyHole

small cock, shemale, threesome, couple, big tits, dogging, facial
15:02

GENDERX FILMS - Slutty Trans Sitter Offers Up Her Tight Huge Cocked Boss

1 week ago

AShemaleTube

anal, big ass, blowjob, big cock, boss, shemale
2:00:59

(WAAA 480 RM) The Perverted Sexual Harassment Boss She Hates

2 weeks ago

AShemaleTube

shemale, anal, creampie
15:18

TRANSFIXED - Big Dick T-Girl Leah Hayes CAUGHT with Big Ass Coworker Alexa Chain In BOSS OFFICE!

2 weeks ago

SomePorn

shemale, dogging, office, facial, shemale and girl, caught, deepthroat
15:19

TRANSFIXED - Big Dick T-Girl Leah Hayes CAUGHT Fucking Big Ass Coworker Alexa Chain In BOSS OFFICE!

2 weeks ago

XXXDan

shemale and girl, shemale, office, facial
18:04

This boss tongues marika ferreiras bulls eye before boinking her stiff in heeled footwear and underwear

3 weeks ago

TrannyGem

creampie, fetish, orgasm, boots, lingerie, latina, blonde
15:35

TRANSFIXED - Sexy Secretary Brittney Kade Gets FREE-USE Fucked At The Office For Boss s Birthday: Porn

1 month ago

XXXDan

office, shemale, secretary
43:53

Youthful trans cutie gets a hard pounding from her boss while on the job

1 month ago

XXXVogue

beauty, blowjob, ladyboy, 18, babe, small tits, boss
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
16:22

POV: Your Ftm Boss Makes You His Fuck Toy

1 month ago

$$ FapHouse

POV, boss
16:08

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

1 month ago

ShemaleZ

ass licking, shemale, cum in mouth, cum in ass, office, big ass
23:04

A bbc boss, BBC Friend, BBC footballer, and a BBC homie pound wet trans anus

1 month ago

ShemaleTaxi

ebony, cartoon, big ass, BBC, anime
15:32

Big arse Maid Facialized After bouncing On Boss massive Cock - MAMACITAZ

2 months ago

ShemaleTaxi

big cock, shemale
2:14:08 50%

Ktb-099 My Crossdressing Lesbian Diary With My Girlfriend My Female Boss Saw Me Having Crossdressing Lesbian Fun With My Girlfriend At Work And Seduced Me! I Ended Up Being Used As A Toy By The Two Of Them And Being Flowers

2 months ago

ShemaleZ

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21:34 20%

Aunt Judys XXX - BBW boss nymph Montse Swinger Gets Caught jacking at the Office

2 months ago

ShemaleTaxi

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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
15:34

The Boss Gives Blowjobs For Christmas Bonus

2 months ago

HClips

amateur, shemale, boss
26:53 60%

Cute Cunt Serving Her Boss

2 months ago

HClips

cute, shemale, amateur, cumshot
37:24 77%

Pimp Blue And Anal Fingering - A Young Miner Trans Was Caught By Surprise When The Boss Began To Pester Her And Hard Fuck Right On The Spot 38 Min

3 months ago

ShemaleZ

surprise, shemale, asian, caught, anal
22:25

Aphrodite Adams In Transroommate - Slut Trans Maid Served By Her Boss Bareback

3 months ago

ShemaleZ

lingerie, shemale, stockings, maid, slut
20:54

Big Tit Latina Shemale Marcella Anal Fucked by Boss and Get Cumshot

3 months ago

$$ FapHouse

ladyboy
21:55 87%

Suckin my boss

3 months ago

AShemaleTube

ebony, shemale, boss
21:31 80%

My boss is transgender, she comes home highly angry and pounds my butt with her big cock Salome Gil

3 months ago

ShemaleTaxi

big cock, shemale, amateur, big ass
17:51

Naughty Secretary Sucked off Company Boss to Promote Herself

4 months ago

$$ FapHouse

big ass, brazil, BBW, tattoo, latina, 18, secretary
19:39

Chick applying for job tries rock hard to coax the boss

4 months ago

ShemaleMovie

anal, dildo, crossdresser, toys, sissy, boss
37:01 57%

Thai maid fucked by shemale boss in the ass

4 months ago

TrannyOne

asian, shemale, thai, maid, boss
2:01:12

Dass-658 Arrogant Shemale Secretary Gets Flowers By Her Boss And Gives Him Anal Entertainment Renka Yuzuki

4 months ago

ShemaleZ

asian, japanese, shemale, stockings, secretary
2:30:27

Dass-528 When I Get , My Boss Gives Me A Sticky French Kiss And Makes Me Cum Again And Again With Marina Ikeda And Ikeda Marina

4 months ago

ShemaleZ

lingerie, shemale, asian, french, stockings
38:56

Guy Fucks His Tran Boss To Save Job - Marissa Minx

4 months ago

AShemaleTube

boss
15:58 56%

Caught Wanking by Your Tranny Boss

4 months ago

$$ FapHouse

handjob, mature, british, caught, blonde, boss
28:53 84%

He Used to Be the Boss but Not Anymore

5 months ago

$$ FapHouse

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15:35

We are going to showcase this slut who is boss

5 months ago

ShemaleMovie

domination, POV, slut
27:25 60%

Boss Shemale Pov 4

5 months ago

ShemaleZ

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26:13

Boss Shemale Pov 2

5 months ago

ShemaleZ

creampie, POV, shemale, asian, boss
21:24

My Boss Is Transgender, She Comes Home Very Angry And Fucks My Ass With Her Big Cock With Salome Gil

5 months ago

ShemaleZ

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21:29

My boss is transgender, she comes home very angry and fucks my ass with her big cock Salome Gil

5 months ago

XXXDan

18, big cock, shemale, amateur, latina
23:35 88%

Horny Ebony Milf Gets Fucked By Her Big Titted Big Cock Trans Boss In The Office, Swallows All Her Cum - Carla Morelli And Lizzy Laynes

5 months ago

BeMyHole

ebony, shemale, POV, anal, chubby, MILF, big tits
22:18

My boss is a transgender she comes home very angry and fucks my arse with his ginormous pink cigar salome gil

5 months ago

ShemaleMovie

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22:34

Pleasing the Beautiful Trans Boss

5 months ago

$$ FapHouse

cumshot, bareback, anal, stockings
15:10

Sexy Secretary Brittney Kade Gets FREE-USE Fucked At The Office For Bosss Birthday

5 months ago

BeMyHole

blowjob, anal, office, secretary, reality, domination, boss
2:16:10 52%

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
15:30 80%

The Boss Put His Trans Secretary On His Knees And Gave Her A Mouthful - Anna Rose

6 months ago

BeMyHole

amateur, blowjob, glasses, secretary, boss, brunette
29:51 71%

Destiny Mira And Leilani Li - Unscheduled Meeting With The Boss

6 months ago

ShemaleZ

shemale, POV, ebony, cumshot, boss
15:40

The Boss Gives Blowjobs for Christmas Bonus

6 months ago

$$ FapHouse

blowjob, shemale, facial
38:16

Yankee transgender princess fucks her boss in the pink hole

6 months ago

ShemaleMovie

shemale
15:06 83%

TRANSFIXED - Horny Leilani Li SNEAKS Big Cock Inside Boss Destiny Miras Pussy! OFFICE CREAMPIE

6 months ago

SomePorn

ebony, public, creampie, big tits, office, ass, BBC
48:42

C4 Film (april 20, 2025) the boss Is a slut on a flick Conference with Her Banker.

6 months ago

ShemaleMovie

handjob, beauty, french, train, lingerie, BDSM, crossdresser
42:43

Zariah Aura In Im The Fucking Boss

6 months ago

ShemaleZ

boss, shemale
28:00

Transgendered Bosses Sc2 Foxxy & Draven Navarro

6 months ago

BeMyHole

shemale, hardcore
48:40

C4 Film (april 20, 2025) the Boss Is a Slut on a Video Conference with Her Banker.

6 months ago

$$ FapHouse

stockings, french, amateur, boss
29:31

Latina she-creature maid cums while being pounded by her boss

6 months ago

ShemaleMovie

shemale, amateur, big ass, brazil
34:31

Kasey Kei, Jade Venus And Rodrigo Amor In Hot Trans Couple Fucked & Facialed By Hunk Boss 35 Min

6 months ago

ShemaleZ

small cock, threesome, couple, interracial, facial, blonde, big cock
34:35 67%

Jade Venus And Kasey Kei - Hot Trans Couple Fucked & Facialed By Hunk Boss

7 months ago

ShemaleZ

handjob, threesome, couple, interracial, MILF, facial, ass licking
15:07 13%

Salome Gil, Porn Asmr Reaction, Transgender Boss Fucks Her Maids Asshole - W...

7 months ago

Beeg

lesbian, POV, anal, maid, ladyboy, cum in mouth, asshole
35:10

Hot Trans Couple fucked & caked By hunk Boss - Jade Venus, Kasey Kei - GenderXFilms

7 months ago

ShemaleMovie

couple, big cock, threesome
35:00

Hot Trans Couple romped & frosted By cub Boss - Jade Venus, Kasey Kei - GenderXFilms

7 months ago

ShemaleTaxi

train, shemale, big cock, couple, boss
40:53

Asian inexperienced she-creature secretary getting poked by her bosses

7 months ago

ShemaleMovie

homemade, anal, 18, shemale and girl, secretary, boss
15:35

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

8 months ago

AnySex

anal, boss, stockings, secretary, office
23:08

Power Dressing: Channeling Your Inner Boss Babe

8 months ago

XXXDan

cumshot compilation, crossdresser, big cock, dress, shemale, teen (18+)
2:01:39

Waaa-480 The Perverted Sexual Harassment Boss She Hates Teases Her Nipples And Makes Her Erect Penis Stick Out! A Shemale Office Lady, Shiori Hirate, Is Humiliated And Made To Cum Over And Over Again

8 months ago

ShemaleZ

threesome, nipples, office, asian, boss
15:39 67%

TRANSFIXED - Sexy Secretary Brittney Kade Gets FREE-USE Fucked At The Office For Boss's Birthday

8 months ago

xHamster

blowjob, office, big cock, secretary, bareback, boss
35:05

Hot Trans Couple Fucked & Facialed By Hunk Boss - Jade Venus, Kasey Kei - GenderXFilms

8 months ago

xHamster

threesome, bareback, couple, blowjob, facial, boss
23:26 79%

Lizzy Laynez And Carla Morelli In Horny Ebony Milf Gets Fucked By Her Big Titted Big Cock Trans Boss In The Office, Swallows All Her Cum Lizzy Laynes 24 Min

9 months ago

ShemaleZ

ebony, shemale, POV, big ass, interracial, MILF, office
17:17

Patricia demonstrates Him Who Is boss

9 months ago

ShemaleMovie

boss, shemale fucks guy, blowjob, domination, BDSM
16:06

Problems at the office sometime need to please the boss

9 months ago

JizzBunker

mature, amateur, mature anal, office, boss
2:31:17 71%

Dass-528 When I Get , My Boss Gives Me A Sticky French Kiss And Makes Me Cum Again And Again - Ikeda Marina And Marina Ikeda

9 months ago

ShemaleZ

kissing, stockings, french, POV, asian, boss
44:41

Shemale fucks hotel boss and squirts his ass

9 months ago

XXXDan

big ass, pissing, hotel, shemale, boss
17:08 78%

Patricia Shows Him Who Is Boss

10 months ago

AShemaleTube

shemale fucks guy, domination, shemale, blowjob, boss
16:02

Boss makes trans secretary Anna Rose kneel down for a mouthful

10 months ago

XXXVogue

secretary, amateur, homemade, POV, boss
39:05 83%

Christina Hearts - The new boss in charge

10 months ago

XXXVogue

boss, crossdresser, creampie, cumshot
15:54 57%

Patty crossdresser I'm your bitch boss

10 months ago

xHamster

mature, stockings, french, crossdresser, masturbation, sissy, boss
24:49

Huge-chested stellar brunette is my female domination boss

10 months ago

ShemaleMovie

shemale, blowjob, indian, boss
2:01:54 47%

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

11 months ago

ShemaleZ

train, anal, threesome, fetish, asian, orgasm, big tits
38:27 71%

My Married boss penetrated Me Like a cockslut

11 months ago

ShemaleMovie

beauty, black, blowjob, big tits, maid, tattoo, crossdresser
15:06

TRANSSENSUAL - Personal secretary Chad Diamond Gets A filthy blowjob From His Hot Boss Lena Kelly

12 months ago

ShemaleTaxi

stockings, shemale, lingerie, secretary, heels
38:25

My Married Boss Fucked Me Like a Slut

1 year ago

xHamster

amateur, cute, anal, big ass, ass, bareback, slut
2:33:44

Mia B - 328 Ruisa Tsuzuki, A Futanari Female Boss Who Was Demented From A Defenseless Tight Skirt That Turned Up With An Erection

1 year ago

ShemaleZ

asian, shemale, futanari
2:34:10

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

1 year ago

ShemaleZ

fetish, asian, gangbang, group, futanari, skirt, boss
21:54

Shemale Porn Video My Boss Is A Transgender She Comes Home Very Angry And Fucks My Ass With His...

1 year ago

TrannyOne

big ass, shemale, anal, big cock, boss
21:02

Shemale Porn Video Missionary TS Boss Barebacks Guy, Cums On His Face

1 year ago

TrannyOne

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16:17

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

1 year ago

TrannyOne

riding, public, outdoor, shemale, 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
28:10

Shemale Porn Video Sexy Asian tranny pleases her boss as she pounds his ass nice and hard

1 year ago

TrannyOne

69, shemale, asian, boss, hardcore
27:33 91%

Shemale Porn Video Fuck My Boss

1 year ago

TrannyOne

anal, shemale, boss, hardcore
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
16:09

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

1 year ago

ShemaleZ

shemale, blowjob, big ass, outdoor, big tits, redhead, tattoo
39:10 95%

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

1 year ago

BeMyHole

blowjob, big tits, ass licking, jerking, big cock, domination, seduced
15:52

The boss put the secretary on her knees and brought his penis to her mouth - Anna Rose

1 year ago

PornHub

teen anal (18+), secretary
43:42

Italian Tranny Boss Manhandles Her Personal Male Sex Slave

1 year ago

ShemaleZ

MILF, BDSM, italian, big cock, blowjob, boss
41:49 93%

Yasmin Lee In Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

1 year ago

ShemaleZ

stockings, asian, BDSM, big cock, secretary, cum in mouth, domination
22:51 90%

Riley Ivy - Beautiful Trans Bareback Anal With Her New Boss

1 year ago

ShemaleZ

beauty, anal, interracial, asian, tattoo, blonde, bareback
22:21

Beautiful Trans Bareback Anal With Her New Boss With Riley Ivy

1 year ago

HClips

amateur, beauty, anal, tattoo, bareback, boss
44:06

Italian Tranny Boss Manhandles Her Personal Male Sex Slave

1 year ago

PornHub

italian
19:02 94%

Spray it all over my face boss

1 year ago

TrannyOne

shemale, big cock, boss
17:29

BIGGER titt rings to please my new boss.

1 year ago

xHamster

boss, shemale and girl, monster, small cock, prostitute
40:52

Asian amateur ladyboy secretary gets fucked by her bosses

1 year ago

JizzBunker

ladyboy, shemale, asian, boss, secretary
21:55 61%

TS secretary fucks her boss

1 year ago

AShemaleTube

shemale, blowjob, secretary, cum in mouth, boss, shemale fucks guy
23:11 14%

A BBC Boss, BBC buddy, BBC footballer, and a BBC homie pulverize humid trans asshole

1 year ago

ShemaleMovie

big ass, 3D, 18, anime, cartoon, futanari, BBC
15:20 17%

Djinn - Martha is a spunk dumpster - vannesa had to do stuff with her old boss

1 year ago

ShemaleMovie

boss, handjob, shemale
25:16

Pretty Office Trans Cums on Desk

1 year ago

xHamster

asshole, shemale, masturbation, solo, office, boss
15:42

Transex Secretary Giving Her Boss

1 year ago

ShemaleZ

shemale, secretary, boss
15:48

Transex secretary giving it to her boss

1 year ago

XXXDan

shemale, blowjob, anal, cumshot, secretary, boss
17:07

Help, My big-chested boss Is A Secret domme - MYLF Femdom

1 year ago

ShemaleTaxi

BBW, boss
15:24

Boss Makes Her Accountant kiss Her bum - Daisy Ducati

1 year ago

ShemaleTaxi

facesitting, taxi, kissing, boss
15:48

Transex Secretary Giving Her Boss

1 year ago

xHamster

blowjob, big ass, brazil, tattoo, secretary, boss
17:07 64%

Sexy boss convinces You to Cheat! dame Fyre Femdom Homewrecker

1 year ago

ShemaleTaxi

pantyhose, stockings, femdom, creampie, cheating, office, taxi
24:07

Female Boss seduce blonde teenager to all girl fuck-fest with Strap-on at work

1 year ago

ShemaleTaxi

teen (18+), strapon, orgasm, uniform, shemale and girl, seduced, boss
21:26 86%

Young Stud Gets Stuffed By Shemale Boss Joanna Jet

1 year ago

AShemaleTube

shemale fucks guy, 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
17:27

Shemale Boss

1 year ago

TrannyOne

boss
16:02 54%

Dominated By My Female Boss - Indonesian Femdom With Awek Melayu

1 year ago

ShemaleZ

femdom, indonesian, 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
29:16

Domino Presley Goes To Her Husband's Boss Michael DelRay And Fucks Him To Let Her Husband Go Home Early - TRANS ANGELS

1 year ago

xHamster

husband, 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
27:34

French Ts Maid With Her Boss Fuck

2 years ago

ShemaleZ

french, maid, vintage, boss
18:04

This boss eats marika ferreiras butt hole before shagging her rigid in heeled footwear and undergarments

2 years ago

KeekAss

ass licking, boss, heels
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
26:46

Maid dual crosses her boss.

2 years ago

ShemaleMovie

maid, BDSM, boss
22:26

Chick with dick pounded by her boss

2 years ago

xHamster

stockings, boss, small tits, shemale fucks guy
55:22 48%

Lesbian training by female boss and used as a toy

2 years ago

JizzBunker

shemale, lesbian, train, japanese, boss, japanese lesbian

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