SHEMALE • BOSS 392 videos

Popular Latest Top rated

41:39 82%

Shemale foxxy angel shows who is the boss

6 years ago

TrannyOne

boss, blowjob
20:05 81%

Sexy shemale boss fuck visitor

9 years ago

DrTuber

ebony, 18, boss, shemale fucks guy, black
41:08 86%

Shemale Foxy Angel Shows Whos the Boss

6 years ago

TXXX

blowjob, fetish, boss
16:28 84%

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

4 years ago

TrannyOne

maid, big cock, boss, BBC
27:16 57%

Young Boss exposes his older secretary to a lustful slut!

4 years ago

TrannyOne

mature, secretary, slut, boss, shemale
49:49 56%

Horny latina secretary seduces and dominates her weenie boss

4 years ago

TrannyOne

secretary, boss, office, seduced
35:58 81%

Jaquelin Braxton Takes Down The Boss

6 years ago

ShemaleZ

MILF, big tits, BDSM, boss
20:45 90%

TS Boss Joanna Fucks Worker and Cum in his Mouth

3 years ago

TrannyOne

feet, fetish, cum in mouth, boss, lingerie, shemale
41:33 72%

Shes The Boss

4 years ago

TrannyOne

shemale, office, boss
50:05 71%

Hot Latina Secretaries Abuse And Dominate Their Boss

4 years ago

TrannyOne

shemale, secretary, boss, threesome
17:08 78%

Patricia Shows Him Who Is Boss

11 months ago

AShemaleTube

shemale fucks guy, domination, shemale, blowjob, boss
23:13 80%

Stockinged blonde tranny fucks and creampies her ass licking boss

8 years ago

TrannyOne

creampie, boss, anal
48:39 82%

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

5 years ago

ShemaleZ

stockings, fetish, BDSM, domination, boss
29:53

Blonde tranny boss ravages this guys ass in the office

8 years ago

TrannyOne

office, boss, anal
39:10 96%

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
29:10 80%

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

2 years ago

ShemaleZ

big tits, husband, ass licking, cumshot, big cock, boss, brunette
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
18:29 70%

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

3 years ago

xHamster

japanese, boss
2:09:24 93%

Shemales bosses

6 years ago

ShemaleZ

uniform, boss, shemale, blowjob, amateur
17:07 65%

Sexy boss convinces You to Cheat! dame Fyre Femdom Homewrecker

1 year ago

ShemaleTaxi

pantyhose, stockings, femdom, creampie, cheating, office, taxi
24:37 44%

Like a Boss

11 years ago

xHamster

boss, small tits, blowjob
19:29 81%

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

4 years ago

TrannyOne

kissing, office, boss
17:27 53%

Shemale Boss

9 years ago

TXXX

small tits, boss, shemale fucks guy
2:09:24 81%

Shemales bosses

6 years ago

Upornia

shemale, blowjob, boss
19:02 94%

Spray it all over my face boss

1 year ago

TrannyOne

shemale, big cock, boss
17:35 70%

I AM YOUR BOSS

2 years ago

XXXDan

POV, big ass, solo, boss
18:27 84%

SHEMALE BOSS FUCKS HER EMPLOYEE

4 years ago

AShemaleTube

big tits, uniform, vintage, boss, shemale fucks guy, cumshot
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
21:26 86%

Young Stud Gets Stuffed By Shemale Boss Joanna Jet

1 year ago

AShemaleTube

shemale fucks guy, boss
21:56 80%

Scintillating trans queen in black lingerie pounds the skinny guys ass like a boss

4 years ago

TrannyOne

black, shemale, skinny, boss, lingerie, ebony
27:51

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

4 years ago

TrannyOne

office, boss
41:49 93%

Yasmin Lee In Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

1 year ago

ShemaleZ

BDSM, big cock, secretary, cum in mouth, domination, boss, shemale fucks guy
22:07 57%

Curvaceous double cock Latina futa dominates and fucks her boss

8 years ago

TrannyOne

domination, futanari, boss, double penetration
25:56 75%

Big shemale shows guy whos the boss

5 years ago

ShemaleZ

redhead, boss
1:54:07

Shemale Boss Bitch

4 years ago

TrannyOne

fat, BBW, boss
31:45 85%

Stefanie Special gets it deep in the ass

5 years ago

ShemaleZ

shemale, lingerie, ass, femboy, beauty, boss
50:05 64%

Boss gets ganged up on by his sexy employees

5 years ago

BeMyHole

pantyhose, redhead, glasses, group, webcam, boss, shemale fucks guy
24:56 80%

TS lady boss has a new lover

14 years ago

AShemaleTube

boss
43:56 86%

Secretary gets her pussy plowed by her hung tranny boss

8 years ago

TrannyOne

secretary, boss, MILF
18:06 67%

The Boss' Bathroom.

13 years ago

xHamster

bathroom, boss
34:32

Her boss has a suprise for her

6 years ago

TXXX

boss, shemale and girl
15:51 79%

The Secretary and The Boss

3 years ago

TrannyOne

secretary, small tits, boss, shemale
28:10 80%

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

4 years ago

TrannyOne

asian, boss
57:08 66%

Horny Latina Secretaries Enslave And Dominate Their Boss

3 years ago

TrannyOne

BDSM, latina, secretary, 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

7 months ago

ShemaleZ

shemale, lesbian, asian, crossdresser, shemale and girl, girlfriend, skirt
29:30 60%

Marita the boss

8 years ago

AShemaleTube

boss
21:22 79%

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

3 years ago

TrannyOne

wife, boss
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
26:42 71%

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

4 years ago

xHamster

beauty, russian, fisting, old and young (18+), food, secretary, boss
24:51 54%

Exciting Compilation With the Sexiest Trans Maids Enjoying Their Bosses Dicks

2 years ago

AnySex

stockings, big ass, big tits, maid, uniform, compilation, small tits
42:38 48%

Horny Latina Secretary Gives It To Her Boss Good And Hard

4 years ago

BeMyHole

pantyhose, mature anal, office, secretary, webcam, boss, shemale fucks guy
19:49 63%

Black shemale boss fucks her male employee

11 years ago

xHamster

black, boss
26:16 79%

Old boss with her tranny secretary

6 years ago

ShemaleZ

mature, creampie, fetish, outdoor, lingerie, ladyboy, uniform
38:57 80%

Marissa Minx Transgendered Bosses

4 years ago

ShemaleZ

MILF, boss
28:50 57%

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

3 years ago

TrannyOne

secretary, boss
17:27 63%

Shemale Boss

13 years ago

AShemaleTube

boss, shemale fucks guy
20:45

TS Boss Barebacks Guy, Cums on His Face

6 years ago

Upornia

blowjob, cumshot, boss, asian
20:09 94%

Shemale Boss Karabella Fucks And Creampies The It Guy

3 years ago

ShemaleZ

stockings, creampie, fetish, lingerie, big cock, boss, shemale fucks guy
38:55

Sexy boss marissa

6 years ago

TXXX

stockings, boss, shemale fucks guy
27:50 93%

Lady-man hammered By Boss And Secretary

6 years ago

ShemaleZ

secretary, boss, shemale
26:59

Babysitter shemale fucks her boss and his friend!

4 years ago

AShemaleTube

big tits, boss
32:46

Transgendered Bosses

6 years ago

Upornia

boss
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

6 months ago

BeMyHole

handjob, ebony, shemale, POV, anal, chubby, MILF
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

9 months ago

ShemaleZ

threesome, nipples, office, asian, boss
21:28

Danielle Fox Is Tthellos dude Boss

6 years ago

ShemaleZ

boss
20:55 61%

TS boss wants hard sex

14 years ago

AShemaleTube

outdoor, boss
28:42

Boss has her cute tranny ass fucked

5 years ago

ShemaleZ

POV, boss, cute
38:56

Guy Fucks His Tran Boss To Save Job - Marissa Minx

5 months ago

AShemaleTube

boss
24:38 71%

Secret doll-twunk gorgeous Assistant Opens saucy assfuck For Manager

5 years ago

TrannyGem

doll, office, boss, ladyboy, cute
36:36 67%

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

4 years ago

TrannyOne

office, boss
26:13 89%

Boss Spurtingcumshotandcreamyhole

4 years ago

Upornia

asian, ladyboy, boss, POV
24:00

Nearly any messy transgender princess Manager acquires banged In The Office

5 years ago

TrannyGem

lingerie, office, boss
21:15 80%

TS Boss Barebacks Guy, Cums on his Face

7 years ago

TrannyGem

bareback, boss, missionary
41:33 65%

Shes The Boss Kenna James and shemale

5 years ago

Analdin

office, babe, erotic, boss, romantic
24:49

Huge-chested stellar brunette is my female domination boss

1 year ago

ShemaleMovie

shemale, blowjob, indian, boss
21:02

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

1 year ago

TrannyOne

riding, shemale, bareback, anal, boss
28:37

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

4 years ago

TrannyOne

secretary, boss, hardcore, amateur
28:50

Tranny bonks Her Boss In Her Mind

6 years ago

ShemaleZ

boss
20:11 90%

TRANSSEXUAL Lena Kelly Gets Vengeance on Porno Managers Cornhole

5 years ago

TrannyGem

femdom, bondage, babe, ass, reality, boss, shemale
16:57

Stgreetingss manmale Boss

6 years ago

TXXX

blowjob, boss
21:02

Missionary TS Boss Barebacks Guy, Cums On His Face

3 years ago

TrannyOne

boss, missionary
15:36

Problems At The Office Sometime acquire to Please The Boss

5 years ago

ShemaleZ

office, boss
15:02

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

1 month ago

AShemaleTube

anal, big ass, blowjob, big cock, boss, shemale
16:47 81%

Sissy secretary gets fucked in toilets by the Boss

6 years ago

ShemaleZ

toilet, secretary, sissy, boss
21:00 84%

Secret sheboy Secretary Opens pleasant butt For Boss

7 years ago

ShemaleZ

secretary, boss, shemale
2:01:54 49%

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
20:22 81%

Nina Lawless Xxx - Nina Lawless - Smoking Boss Bitch

3 years ago

ShemaleZ

smoking, boss, solo
30:04

Sexy boss fucks with secretary

13 years ago

AShemaleTube

secretary, boss
15:16

Chunky black shemale Paris bangs with her future hung boss

8 years ago

TrannyOne

black, boss
19:24

Girl like me, boss, knows many ways how to please

4 years ago

xHamster

blowjob, boss
39:55 74%

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

4 years ago

TrannyOne

fat, office, secretary, boss
18:31

She got tranny boss

5 years ago

ShemaleMovie

boss
24:30 94%

Boss Overallsandacreampie

4 years ago

ShemaleZ

ladyboy, boss, asian, creampie, POV, shemale
26:46

Maid double crosses her boss.

4 years ago

ShemaleTaxi

maid, taxi, boss, double penetration
25:11

My Transexual Boss - Scene 1

6 years ago

ShemaleZ

boss, ass licking
15:51 67%

Cute TS Secretary with Her Boss

10 years ago

TXXX

cute, creampie, secretary, small tits, boss
39:06 89%

Transgendered Bosses – Huge-Titted TRANSSEXUAL Marissa Minx Sweetie Tears Up Him From Behind At The Office

3 years ago

KeekAss

MILF, office, blonde, boss, shemale fucks guy
39:35

Boss Level

4 years ago

Upornia

big tits, boss
2:09:54

Transgender princesses Bosses

5 years ago

TrannyGem

boss
20:47 86%

Boss Jeanshortscreampieride

4 years ago

TXXX

ladyboy, boss
23:54 73%

Tranny servant and young boss

6 years ago

ShemaleZ

lingerie, uniform, boss, blowjob, mature
15:58 56%

Caught Wanking by Your Tranny Boss

6 months ago

$$ FapHouse

handjob, mature, british, caught, blonde, 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
34:24

Whois Boss.

5 years ago

ShemaleZ

boss, shemale fucks guy
41:22 86%

Maid receives poked By Her Boss

6 years ago

TXXX

maid, uniform, boss
42:43

Zariah Aura In Im The Fucking Boss

7 months ago

ShemaleZ

boss, shemale
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
39:12

Fucking the boss in the office

5 years ago

TrannyOne

office, boss
21:05

TS Boss Barebacks Guy, Cums on His Face

6 years ago

ShemaleZ

boss, bareback
35:00

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

8 months ago

ShemaleTaxi

train, shemale, big cock, couple, boss
57:21 58%

Horny latina secretaries enslave and dominate their boss

4 years ago

AShemaleTube

mature, fetish, uniform, cumshot, group, secretary, domination
28:52

Butthole plowing All Day - Boss Film

7 years ago

ShemaleZ

boss
20:07

Boss receives Double Teamed - Scene 1

7 years ago

ShemaleZ

mature, boss, double penetration
21:55 87%

Suckin my boss

5 months ago

AShemaleTube

ebony, shemale, boss
31:23

Transgendered Bosses 3 - Eva Maxim

2 years ago

ShemaleZ

handjob, big ass, boss
32:51

Transgendered Bosses

5 years ago

TrannyGem

boss
27:34

Banging The Manager

5 years ago

TrannyGem

boss
21:23

[shelady] gigantic Boss Khloe Hart bonks Her Job Applicant.

5 years ago

ShemaleZ

boss
44:41 62%

Shemale fucks hotel boss and squirts his ass

3 years ago

xHamster

handjob, squirt, asian, orgasm, japanese, 18, swallow
26:29 58%

Riley Storm Assistant Pummel

5 years ago

TrannyGem

creampie, anal, office, old and young (18+), secretary, boss

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