SHEMALE • BOSS 406 videos

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39:33

Chanel Santini is the fucking boss

Yesterday

AShemaleTube

shemale
24:13

My Boss Fucks Me in the Office

5 days ago

$$ FapHouse

couple, shemale fucks guy, teen (18+), amateur
16:03

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

1 week ago

AShemaleTube

big cock, shemale and girl, shemale, POV, boss, office
29:29

Latina shemale maid cums while being fucked by her boss ft. Erika Lee: Porn

1 week ago

JizzBunker

brunette, cum while fucked, latina, amateur
16:32

TRANSFIXED - Hot Blonde Boss Jade Venus Gets Assfuced Cum In Mouth From Horny Office s Assistant: Porn

1 week ago

XXXDan

office, public
15:36

My mean boss by Elliotyip futa x male

2 weeks ago

TXXX

big ass, futanari, mature, shemale, cartoon
15:15

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

2 weeks ago

BeMyHole

shemale, secretary, boss, domination
15:39 82%

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

3 weeks ago

SomePorn

ebony, femdom, shemale, creampie, hairy, dogging, tattoo
16:20

TRANSFIXED - Teen Sitter Gets DP Fucked As a Special Going-Away Present By Her Bosses

3 weeks ago

SomePorn

18, threesome, arab, double penetration
16:20

TRANSFIXED - Teen Sitter Gets Fucked DP As Special Going-Away Present By Her Bosses

3 weeks ago

JizzBunker

anal, arab
15:18 60%

Big Dick T-girl Caught Fucking Big Ass Coworker Alexa Chain In Boss Office! - Leah Hayes

3 weeks ago

ShemaleZ

stockings, big ass, tattoo, office, caught, big cock, boss
48:44

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

4 weeks ago

$$ FapHouse

fetish, shemale fucks guy, shemale, ladyboy, domination
15:36

Tranny Hard Time with My Boss

4 weeks ago

$$ FapHouse

cumshot, boss, amateur
22:18

Boss Free Use

1 month ago

AShemaleTube

anal, shemale, boss, blonde
36:38

The Boss! Aubrey Kate Domination

1 month ago

$$ FapHouse

shemale fucks guy, domination
29:42 57%

Ts - Maid Seduces Bosses

1 month ago

ShemaleZ

shemale, threesome, MILF, maid, cumshot, big cock, seduced
15:17

Hot secretary with gigantic donk wants promotion, boss

1 month ago

IcePorn

shemale, bareback, ladyboy, boss, secretary
15:28

Leah Hayes gets caught with big-titted coworker Alexa Chains in the boss office for a wild face-pounding session!

1 month ago

XXXVogue

shemale, cumshot
34:35

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

1 month ago

BeMyHole

blowjob, threesome, couple, dogging, facial, ass licking, deepthroat
15:03

Slutty trans sitter Avery Lust submits her tight hole to her well-endowed boss Michael Del Ray

2 months ago

XXXVogue

riding, shemale fucks guy, big cock
34:40 60%

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

2 months ago

BeMyHole

small cock, shemale, threesome, couple, big tits, dogging, facial
15:02 60%

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

2 months ago

AShemaleTube

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

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

3 months ago

AShemaleTube

shemale, anal, creampie
15:18 93%

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

3 months 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!

3 months ago

XXXDan

shemale and girl, shemale, office, facial
18:04 60%

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

3 months ago

TrannyGem

creampie, big ass, fetish, orgasm, boots, lingerie, latina
15:35

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

3 months ago

XXXDan

office, shemale, secretary
43:53

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

3 months ago

XXXVogue

beauty, blowjob, 18, babe, small tits, boss
29:17 71%

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

3 months ago

ShemaleZ

shemale, shemale and girl, creampie, MILF, office, stockings
16:22

POV: Your Ftm Boss Makes You His Fuck Toy

3 months ago

$$ FapHouse

POV, boss
16:08

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

4 months 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

4 months ago

ShemaleTaxi

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

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

4 months ago

ShemaleTaxi

big cock, shemale
2:14:08 56%

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

4 months ago

ShemaleZ

lesbian, POV, threesome, asian, crossdresser, girlfriend, toys
21:34 20%

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

4 months ago

ShemaleTaxi

swinger, spanish, big ass, BBW, office, caught, aunt
15:10 80%

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

4 months ago

BeMyHole

blowjob, shemale and girl, creampie, 18, boss
15:34

The Boss Gives Blowjobs For Christmas Bonus

5 months ago

HClips

amateur, shemale, boss
26:53 60%

Cute Cunt Serving Her Boss

5 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

5 months ago

ShemaleZ

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

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

5 months ago

ShemaleZ

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

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

5 months ago

$$ FapHouse

ladyboy
21:55 88%

Suckin my boss

6 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

6 months ago

ShemaleTaxi

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

Naughty Secretary Sucked off Company Boss to Promote Herself

6 months ago

$$ FapHouse

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

Chick applying for job tries rock hard to coax the boss

6 months ago

ShemaleMovie

anal, dildo, crossdresser, toys, sissy, boss
2:01:12

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

6 months ago

ShemaleZ

asian, japanese, shemale, stockings, secretary
37:01 57%

Thai maid fucked by shemale boss in the ass

6 months ago

TrannyOne

asian, shemale, thai, maid, boss
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

6 months ago

ShemaleZ

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

Guy Fucks His Tran Boss To Save Job - Marissa Minx

7 months ago

AShemaleTube

boss
15:58 56%

Caught Wanking by Your Tranny Boss

7 months ago

$$ FapHouse

handjob, mature, british, caught, blonde, boss
28:53 85%

He Used to Be the Boss but Not Anymore

7 months ago

$$ FapHouse

mature, mature anal, ass to mouth, cum in mouth, sissy, boss, cum in ass
15:35

We are going to showcase this slut who is boss

7 months ago

ShemaleMovie

domination, POV, slut
27:25 71%

Boss Shemale Pov 4

7 months ago

ShemaleZ

shemale, POV, asian, boss, lingerie
26:13

Boss Shemale Pov 2

7 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

7 months ago

ShemaleZ

big ass, shemale, stockings, ass, colombian
21:29

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

7 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

8 months ago

BeMyHole

handjob, ebony, shemale, POV, chubby, MILF, big tits
22:34

Pleasing the Beautiful Trans Boss

8 months ago

$$ FapHouse

cumshot, bareback, anal, stockings, MILF
22:18

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

8 months ago

ShemaleMovie

shemale and girl, shemale, boss, maid
15:10

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

8 months ago

BeMyHole

blowjob, anal, office, secretary, reality, domination, boss
2:16:10 50%

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

8 months ago

ShemaleZ

shemale, lesbian, asian, crossdresser, shemale and girl, girlfriend, skirt
29:51 72%

Destiny Mira And Leilani Li - Unscheduled Meeting With The Boss

8 months ago

ShemaleZ

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

The Boss Gives Blowjobs for Christmas Bonus

8 months ago

$$ FapHouse

blowjob, shemale, facial
15:06 83%

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

8 months ago

SomePorn

ebony, public, big tits, office, ass, BBC, boss
38:16

Yankee transgender princess fucks her boss in the pink hole

8 months ago

ShemaleMovie

shemale
48:42

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

8 months ago

ShemaleMovie

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

Zariah Aura In Im The Fucking Boss

8 months ago

ShemaleZ

boss, shemale
28:00

Transgendered Bosses Sc2 Foxxy & Draven Navarro

8 months ago

BeMyHole

shemale, hardcore
48:40

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

9 months ago

$$ FapHouse

stockings, french, amateur, boss
29:31

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

9 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

9 months ago

ShemaleZ

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

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

9 months ago

ShemaleZ

handjob, threesome, couple, interracial, MILF, facial, ass licking
35:10

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

9 months ago

ShemaleMovie

couple, big cock, threesome, train
15:07 11%

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

9 months ago

Beeg

lesbian, POV, anal, maid, ladyboy, cum in mouth, asshole
35:00

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

9 months ago

ShemaleTaxi

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

Asian inexperienced she-creature secretary getting poked by her bosses

10 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

10 months ago

AnySex

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

Power Dressing: Channeling Your Inner Boss Babe

10 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

11 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

11 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

11 months ago

xHamster

threesome, bareback, couple, blowjob, facial, boss
23:26 80%

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

11 months ago

ShemaleZ

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

Patricia demonstrates Him Who Is boss

11 months ago

ShemaleMovie

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

Problems at the office sometime need to please the boss

11 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

1 year ago

ShemaleZ

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

Shemale fucks hotel boss and squirts his ass

1 year ago

XXXDan

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

Patricia Shows Him Who Is Boss

1 year ago

AShemaleTube

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

Boss makes trans secretary Anna Rose kneel down for a mouthful

1 year ago

XXXVogue

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

Christina Hearts - The new boss in charge

1 year ago

XXXVogue

boss, crossdresser, creampie, cumshot
15:54 56%

Patty crossdresser I'm your bitch boss

1 year ago

xHamster

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

Huge-chested stellar brunette is my female domination boss

1 year ago

ShemaleMovie

shemale, blowjob, indian, boss
2:01:54 50%

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

1 year ago

ShemaleZ

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

My Married boss penetrated Me Like a cockslut

1 year 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

1 year ago

ShemaleTaxi

stockings, shemale, lingerie, secretary, heels
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, skirt
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

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

riding, shemale, bareback, anal, boss
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

blowjob, outdoor, big tits, redhead, tattoo, riding, ass
39:10 96%

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

1 year ago

BeMyHole

blowjob, anal, big tits, ass licking, jerking, big cock, domination
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 90%

Yasmin Lee In Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

1 year ago

ShemaleZ

asian, BDSM, big cock, secretary, cum in mouth, 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
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
23:11 14%

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

1 year ago

ShemaleMovie

3D, 18, anime, cartoon, futanari, BBC, boss
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

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