SHEMALE • BOSS 342 videos

Popular Latest Top rated

20:11 94%

TRANSSEXUAL Lena Kelly Gets Vengeance on Porno Managers Cornhole

3 years ago

TrannyGem

femdom, bondage, babe, ass, reality, boss
20:45 94%

TS Boss Joanna Fucks Worker and Cum in his Mouth

2 years ago

TrannyOne

feet, fetish, cum in mouth, boss, lingerie, shemale
27:50 93%

Lady-man hammered By Boss And Secretary

4 years ago

ShemaleZ

secretary, boss
20:09 92%

Shemale Boss Karabella Fucks And Creampies The It Guy

1 year ago

ShemaleZ

stockings, creampie, fetish, lingerie, big cock, boss, shemale fucks guy
27:33 89%

Fuck My Boss

3 years ago

BeMyHole

beauty, dogging, ass licking, shaving, slut, boss
22:11 88%

Here we enjoy Boss again getting banged

3 years ago

ShemaleZ

creampie, asian, boss
41:33 88%

Shes The Boss

2 years ago

TrannyOne

shemale, office, boss
16:16 86%

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

10 months ago

BeMyHole

public, shemale, outdoor, latina, ass licking, shemale and girl, riding
21:22 85%

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

2 years ago

TrannyOne

wife, boss
41:08 84%

Shemale Foxy Angel Shows Whos the Boss

4 years ago

TXXX

blowjob, fetish, boss
34:33 83%

Shemale boss and female secretary have some amazing sex together

4 years ago

TrannyOne

secretary, boss
23:13 83%

Stockinged blonde tranny fucks and creampies her ass licking boss

6 years ago

TrannyOne

creampie, boss
17:36 82%

Sexy maid trying to satisfy her bosses

4 years ago

TXXX

maid, shemale and girl, boss
48:39 82%

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

3 years ago

ShemaleZ

stockings, fetish, BDSM, domination, boss
19:29 80%

Horny lad gets his sweet butt drilled hard by his TS boss in the office

2 years ago

TrannyOne

kissing, office, boss
15:13 80%

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

2 years ago

Upornia

asian, maid, crossdresser, sissy, boss
16:28 79%

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

2 years ago

TrannyOne

maid, big cock, boss, BBC
20:05 79%

Sexy shemale boss fuck visitor

8 years ago

DrTuber

ebony, 18, boss, shemale fucks guy
23:42 79%

The Boss Adam With Erica Cherry And Sabina Steele

1 year ago

ShemaleZ

threesome, boss
35:58 79%

Jaquelin Braxton Takes Down The Boss

5 years ago

ShemaleZ

MILF, big tits, BDSM, boss
16:47 75%

Sissy secretary gets fucked in toilets by the Boss

4 years ago

ShemaleZ

toilet, secretary, sissy, boss
2:09:24 74%

Shemales bosses

4 years ago

Upornia

shemale, blowjob, boss
20:22 74%

Nina Lawless Xxx - Nina Lawless - Smoking Boss Bitch

2 years ago

ShemaleZ

smoking, boss
40:45 73%

Sasha jacks romps the hotel boss

3 years ago

ShemaleTaxi

taxi, BBC, hotel, boss
17:16 73%

Facial Act Sunshyne Monroe Fucks The Boss

2 years ago

BeMyHole

couple, facial, condom, shaving, boss, shemale fucks guy
15:51 71%

The Secretary and The Boss

2 years ago

TrannyOne

secretary, small tits, boss, shemale
17:35 70%

I AM YOUR BOSS

10 months ago

XXXDan

POV, big ass, solo, boss
15:28 69%

My Busty Fit tranny Boss owned my mouth - WickedWhims

10 months ago

xHamster

black, old and young (18+), cartoon, boss
15:21 68%

Bulky handyman repairman and his boss in a workshop during work at mboa. Exclusivity on XVIDEOS

1 year ago

ShemaleTaxi

ebony, public, teen (18+), bisexual, orgasm, gangbang, bareback
20:22 67%

Boss hogg and XL Xar - tranny takes creampie from huge dildo

1 year ago

PornHub

huge dildo, dildo, sissy, boss, crossdresser
57:08 66%

Horny Latina Secretaries Enslave And Dominate Their Boss

2 years ago

TrannyOne

BDSM, latina, secretary, domination, boss
26:16 65%

Old boss with her tranny secretary

4 years ago

ShemaleZ

mature, fetish, outdoor, lingerie, uniform, ass to mouth, secretary
20:55 63%

TS boss wants hard sex

13 years ago

AShemaleTube

outdoor, boss
22:07 62%

Curvaceous double cock Latina futa dominates and fucks her boss

6 years ago

TrannyOne

domination, futanari, boss, double penetration
41:33 61%

Shes The Boss Kenna James and shemale

3 years ago

Analdin

office, babe, erotic, boss, romantic
39:55 60%

Horny boss gets his old fat ass banged hard by the horny TS secretary

2 years ago

TrannyOne

fat, office, secretary, boss
44:41 59%

Shemale fucks hotel boss and squirts his ass

1 year ago

xHamster

handjob, squirt, asian, orgasm, japanese, 18, swallow
27:16 58%

Young Boss exposes his older secretary to a lustful slut!

2 years ago

TrannyOne

mature, secretary, slut, boss
42:51 57%

Horny latina secretary gives it to her boss good and hard

3 years ago

AShemaleTube

homemade, secretary, domination, webcam, boss, shemale fucks guy
26:29 56%

Riley Storm Assistant Pummel

3 years ago

TrannyGem

creampie, office, old and young (18+), secretary, boss
17:27 55%

Shemale Boss

8 years ago

TXXX

small tits, boss
24:35 53%

Hot curvy MILFs amazing lesdom porn clip

3 years ago

Analdin

lesbian, chubby, MILF, bondage, babe, boss, brunette
55:22

Lesbian training by female boss and used as a toy

8 months ago

JizzBunker

shemale, lesbian, train, japanese, boss, japanese lesbian
42:29

Yasmin Lee Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

1 month ago

AShemaleTube

asian, shemale fucks guy, shemale, big cock, secretary
21:55

TS secretary fucks her boss

1 week ago

AShemaleTube

shemale fucks guy, cum in mouth, blowjob, secretary, shemale, amateur
39:33

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

3 months ago

xHamster

blowjob, big cock, seduced, boss
17:07

Sexy boss convinces You to Cheat! dame Fyre Femdom Homewrecker

1 month ago

ShemaleTaxi

pantyhose, femdom, shemale, creampie, office, stockings
49:49

Horny latina secretary seduces and dominates her weenie boss

2 years ago

TrannyOne

secretary, boss
20:20

Hot BDSM Boss Plugs and Disciplines Bimbo Secretary for Mistakes

2 years ago

PornHub

train, fetish, bondage, BDSM, babe, secretary, slut
40:45

Sasha strokes and The motel boss

4 years ago

ShemaleMovie

shemale and girl, big cock, hotel, boss
43:56

Secretary gets her pussy plowed by her hung tranny boss

6 years ago

TrannyOne

secretary, boss
21:53

Amateur Sex My Boss Is A Transgender She Comes Home Very Angry And Fucks My Ass With His Big Cock Salome Gil

11 months ago

BeMyHole

shemale, anal, maid, blonde, boss, shemale fucks guy
50:05

Hot Latina Secretaries Abuse And Dominate Their Boss

2 years ago

TrannyOne

shemale, secretary, boss
26:03

Mature Shemale Secretary Seduces Boss

Yesterday

PornHub

MILF, shemale, mature, mature anal, cartoon
15:20

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

2 weeks ago

ShemaleMovie

boss, handjob, shemale
26:38

Indian Shemale Interview Ends In Fucking The Boss

1 year ago

Upornia

indian, shemale and girl, audition, boss
26:42

Young Boss Tests His Mature Secretary's Cunt For Strength!

2 years ago

xHamster

mature, russian, fisting, old and young (18+), food, secretary, slut
24:07

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

2 months ago

ShemaleTaxi

teen (18+), strapon, orgasm, uniform, shemale and girl, seduced, cosplay
16:02

Dominated By My Female Boss - Indonesian Femdom With Awek Melayu

4 months ago

ShemaleZ

femdom, indonesian, boss
43:44

Sissy Caption Story: Bosses Orders

1 year ago

ShemaleTaxi

ebony, blowjob, secretary, taxi, sissy, boss
50:05

Boss gets ganged up on by his sexy employees

3 years ago

BeMyHole

pantyhose, redhead, glasses, group, webcam, boss, shemale fucks guy
21:26

Young Stud Gets Stuffed By Shemale Boss Joanna Jet

2 months ago

AShemaleTube

shemale fucks guy, boss
26:10

S..Vegas Bitch Boss

4 days ago

AShemaleTube

ladyboy, vintage, big cock, anal
29:10

Michael Del Ray, Del Ray And Domino Presley In Goes To Her Husbands Boss And Fucks Him To Let Her Husband Go Home Early

4 months ago

ShemaleZ

shemale, big tits, husband, ass licking, cumshot, big cock, boss
29:28

Indian Boss Fucked Hot Shemale

1 year ago

xHamster

indian, anal, big ass, asian, ladyboy, boss
23:54

Tranny servant and young boss

4 years ago

ShemaleZ

lingerie, uniform, boss
2:09:24

Shemales bosses

4 years ago

ShemaleZ

uniform, boss
41:39

Shemale foxxy angel shows who is the boss

4 years ago

TrannyOne

boss
25:16

Pretty Office Trans Cums on Desk

3 weeks ago

xHamster

asshole, shemale, masturbation, solo, office, boss
24:51

Exciting Compilation With the Sexiest Trans Maids Enjoying Their Bosses Dicks

5 months ago

AnySex

stockings, big ass, big tits, maid, compilation, boss
18:06

Ebony secretary must learn how to serve a big dick of her futanari MILF boss

1 year ago

AnySex

MILF, secretary, futanari, boss
24:37

Like a Boss

9 years ago

xHamster

boss, small tits
23:11

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

2 weeks ago

ShemaleMovie

big ass, 3D, 18, anime, cartoon, futanari, BBC
22:30

Regina Twist Pleasing The Beautiful Trans Boss

10 months ago

ShemaleZ

ass to mouth, boss, stockings
50:37

Horny secretary has her way with the boss

2 years ago

TrannyOne

office, secretary, boss
38:57

Marissa Minx Transgendered Bosses

3 years ago

ShemaleZ

MILF, boss
31:23

Transgendered Bosses 3 - Eva Maxim

11 months ago

ShemaleZ

handjob, big ass, boss
29:22

Indian Boss Fucked Hot Shemale

12 months ago

ShemaleZ

indian, teen (18+), boss
17:19

Slim ladyboy maid tops her boss

2 years ago

AShemaleTube

maid, uniform, boss, shemale fucks guy
42:38

Horny Latina Secretary Gives It To Her Boss Good And Hard

3 years ago

BeMyHole

pantyhose, mature anal, office, secretary, webcam, boss
25:20

My transsexual boss

3 years ago

ShemaleMovie

creampie, boss
18:29

Japanese Boss Lady want to know how well the new intern fucks

1 year ago

xHamster

japanese, boss
26:13

Boss Spurtingcumshotandcreamyhole

3 years ago

Upornia

asian, ladyboy, boss
28:42

Boss has her cute tranny ass fucked

3 years ago

ShemaleZ

POV, boss
26:28

Shemale Maid nailed By Her shemale Boss

4 years ago

ShemaleZ

shemale, maid, uniform, boss
28:50

Lewd Secretaries gang Up On Their penis Manager

3 years ago

TrannyGem

office, gangbang, secretary, cum in mouth, domination, penis, boss
15:48

Transex Secretary Giving Her Boss

1 month ago

xHamster

anal, shemale fucks guy, blowjob, shemale, secretary, big ass
18:50

My boss is a futanari

7 months ago

AShemaleTube

futanari, boss
37:14

Latina Secretary And The Boss Have A Naughty Fling

2 years ago

HClips

mature, latina, big cock, secretary, webcam, boss
24:30

Boss Overallsandacreampie

3 years ago

ShemaleZ

ladyboy, boss
29:53

Blonde tranny boss ravages this guys ass in the office

6 years ago

TrannyOne

office, boss
18:06

The Boss' Bathroom.

12 years ago

xHamster

bathroom, boss
17:54

How to Turn Your Boss Into a Bimbo

2 months ago

PornHub

solo, boss
22:38

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

6 months ago

ShemaleZ

cum in mouth, bathroom, boss, cum in ass
25:26

Fucking my wild horny big tits boss in the office

1 year ago

TrannyOne

big tits, office, boss
15:01

FUTANARI MILF Fucks Herself AND Futa Boss Assfucks HARD on a Plane - SO MUCH CUM - Amys Big Wish S01-4-5

1 year ago

TXXX

cartoon, futanari, boss
27:51

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

2 years ago

TrannyOne

office, boss
18:27

SHEMALE BOSS FUCKS HER EMPLOYEE

2 years ago

AShemaleTube

big tits, uniform, vintage, boss, shemale fucks guy
28:37

Sexy Horny Secretaries Make Their Boss Service Their Dicks And Eat Cum

2 years ago

TrannyOne

secretary, boss, hardcore
30:44

Sissy secretary lunchtime fucking by boss

4 years ago

ShemaleZ

secretary, sissy, boss
20:45

TS Boss Barebacks Guy, Cums on His Face

4 years ago

Upornia

blowjob, cumshot, boss
34:32

Her boss has a suprise for her

4 years ago

TXXX

boss
21:53

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

9 months ago

BeMyHole

maid, office, shemale and girl, boss
25:37

Maid For Her Boss

2 years ago

Upornia

stockings, maid, boss
28:50

Sexy horny secretaries make their boss service their dicks and eat cum

2 years ago

TrannyOne

secretary, boss
36:36

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

2 years ago

TrannyOne

office, boss
22:11

Boss Blackbabydoll2creampiescloseupcum

3 years ago

ShemaleZ

creampie, POV, asian, boss
24:42

Trans Love - Scene 4 - Boss Film

4 years ago

ShemaleZ

vintage, skinny, boss
17:01

Candee Lace - Very hot maid services her boss #ROLEPLAY2018

4 years ago

HClips

teen (18+), creampie, POV, maid, blonde, boss
18:04

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

6 months ago

KeekAss

ass licking, boss
26:46

Maid dual crosses her boss.

7 months ago

ShemaleMovie

maid, BDSM, boss
36:30

Transgendered Bosses 3 - Kasey Kei

11 months ago

ShemaleZ

shemale, boss
15:10

UTANARI milf nails Herself AND Futa Boss Assfucks HARD on a Plane - SO MUCH cum - Amys Big Wish S01-4-5

1 year ago

ShemaleTaxi

cartoon, futanari, boss, gape
26:59

Babysitter shemale fucks her boss and his friend!

2 years ago

AShemaleTube

big tits, boss
27:12

Desi Bengali Real Wife Office Sex With Boss

2 years ago

Upornia

wife, office, boss
40:52

Asian amateur ladyboy secretary getting fucked by her bosses

3 years ago

xHamster

teen (18+), teen anal (18+), ladyboy, secretary, boss
23:37

Khloe Hart & Christian - Bareback Boss

3 years ago

BeMyHole

bareback, boss
32:51

Transgendered Bosses

3 years ago

TrannyGem

boss
32:46

Transgendered Bosses

4 years ago

Upornia

boss
23:11

3some large O Party - Boss Film

4 years ago

ShemaleZ

handjob, party, group, boss

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