TRANNY • BOSS 203 videos

Popular Latest Top rated

24:30 96%

Boss Overallsandacreampie

4 years ago

ShemaleZ

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

Boss Spurtingcumshotandcreamyhole

4 years ago

Upornia

asian, ladyboy, boss, POV
20:09 93%

Shemale Boss Karabella Fucks And Creampies The It Guy

2 years ago

ShemaleZ

stockings, creampie, big ass, fetish, lingerie, big cock, bareback
27:50 93%

Lady-man hammered By Boss And Secretary

5 years ago

ShemaleZ

secretary, boss, shemale
41:49 93%

Yasmin Lee In Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

11 months ago

ShemaleZ

stockings, asian, BDSM, secretary, cum in mouth, domination, boss
2:09:24 92%

Shemales bosses

5 years ago

ShemaleZ

uniform, boss, shemale, blowjob
22:30 91%

Regina Twist Pleasing The Beautiful Trans Boss

1 year ago

ShemaleZ

ass to mouth, boss, stockings
22:51 89%

Riley Ivy - Beautiful Trans Bareback Anal With Her New Boss

11 months ago

ShemaleZ

beauty, anal, interracial, asian, tattoo, blonde, bareback
39:33 87%

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, anal
22:11 87%

Here we enjoy Boss again getting banged

4 years ago

ShemaleZ

creampie, asian, boss, POV
22:11 87%

Boss Blackbabydoll2creampiescloseupcum

4 years ago

ShemaleZ

creampie, POV, asian, boss, ladyboy, stockings
25:56 86%

Big shemale shows guy whos the boss

5 years ago

ShemaleZ

redhead, boss
41:22 86%

Maid receives poked By Her Boss

5 years ago

TXXX

maid, uniform, boss
41:08 85%

Shemale Foxy Angel Shows Whos the Boss

5 years ago

TXXX

blowjob, fetish, boss
22:07 85%

Boss Boyshortsbikinisocksbarebacking

4 years ago

Upornia

asian, ladyboy, boss
21:00 83%

Secret sheboy Secretary Opens pleasant butt For Boss

7 years ago

ShemaleZ

secretary, boss
24:03 83%

Transgendered Bosses 3 With Dillon Diaz And Gracie Jane

2 years ago

Upornia

stockings, fetish, big tits, lingerie, blonde, boss
36:30 83%

Transgendered Bosses 3 - Kasey Kei

2 years ago

ShemaleZ

shemale, boss
17:36 83%

Sexy maid trying to satisfy her bosses

5 years ago

TXXX

maid, shemale and girl, boss, threesome, amateur
24:42 82%

Trans Love - Scene 4 - Boss Film

6 years ago

ShemaleZ

vintage, skinny, boss, stockings
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
20:47 80%

Boss Jeanshortscreampieride

4 years ago

TXXX

ladyboy, boss
26:28 80%

Shemale Maid nailed By Her shemale Boss

5 years ago

ShemaleZ

shemale, maid, uniform, boss
2:09:24 80%

Shemales bosses

5 years ago

Upornia

shemale, blowjob, boss
38:57 80%

Marissa Minx Transgendered Bosses

4 years ago

ShemaleZ

MILF, boss
20:22 79%

Nina Lawless Xxx - Nina Lawless - Smoking Boss Bitch

3 years ago

ShemaleZ

smoking, boss, solo
23:26 78%

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

4 months ago

ShemaleZ

ebony, shemale, POV, big ass, interracial, MILF, office
33:10 78%

Boss Skimpylingeriehjandstroke

4 years ago

ShemaleZ

POV, boss, asian
16:47 76%

Sissy secretary gets fucked in toilets by the Boss

5 years ago

ShemaleZ

toilet, secretary, sissy, boss
15:01 75%

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

2 years ago

TXXX

cartoon, futanari, boss, solo
26:16 75%

Old boss with her tranny secretary

5 years ago

ShemaleZ

mature, creampie, fetish, outdoor, lingerie, uniform, ass to mouth
23:42 73%

The Boss Adam With Erica Cherry And Sabina Steele

2 years ago

ShemaleZ

threesome, boss
29:28 73%

Indian Boss Fucked Hot Shemale

2 years ago

xHamster

indian, anal, big ass, ladyboy, shemale fucks guy
41:34 71%

Thai Tranny June Gets Washed In The Shower By The Boss

3 years ago

ShemaleZ

thai, redhead, shower, boss, asian, big ass
15:28 71%

My Busty Fit tranny Boss owned my mouth - WickedWhims

1 year ago

xHamster

black, old and young (18+), cartoon, boss, shemale fucks guy, domination
15:13 70%

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+)
29:51 69%

Destiny Mira And Leilani Li - Unscheduled Meeting With The Boss

3 weeks ago

ShemaleZ

shemale, POV, ebony, cumshot, boss
23:54 69%

Tranny servant and young boss

5 years ago

ShemaleZ

lingerie, uniform, boss, blowjob, mature
26:38 69%

Indian Shemale Interview Ends In Fucking The Boss

2 years ago

Upornia

indian, shemale and girl, audition, boss
29:10 67%

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
18:29 67%

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

3 years ago

xHamster

japanese, boss
34:35 67%

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

1 month ago

ShemaleZ

facial, interracial, big cock, threesome, shemale, boss
2:31:17 67%

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

4 months ago

ShemaleZ

kissing, stockings, french, POV, fetish, asian, boss
26:42 65%

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

3 years ago

xHamster

russian, fisting, old and young (18+), food, secretary, boss, gape
44:41 60%

Shemale fucks hotel boss and squirts his ass

2 years ago

xHamster

handjob, squirt, asian, orgasm, japanese, 18, swallow
2:16:10 53%

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

3 weeks ago

ShemaleZ

shemale, lesbian, asian, crossdresser, shemale and girl, girlfriend, skirt
16:02 50%

Dominated By My Female Boss - Indonesian Femdom With Awek Melayu

1 year ago

ShemaleZ

femdom, indonesian, boss
29:22 50%

Indian Boss Fucked Hot Shemale

2 years ago

ShemaleZ

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

Shemale Boss

9 years ago

TXXX

small tits, boss, shemale fucks guy
2:01:54 46%

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

6 months ago

ShemaleZ

shemale, train, anal, threesome, fetish, asian, orgasm
24:37 44%

Like a Boss

10 years ago

xHamster

boss, small tits
15:54 40%

Patty crossdresser I'm your bitch boss

5 months ago

xHamster

mature, stockings, french, crossdresser, masturbation, small tits, sissy
25:41 14%

Horny guys fucking hot boss

5 years ago

ShemaleZ

boss
27:25

Boss Shemale Pov 4

4 days ago

ShemaleZ

shemale, POV, asian
26:13

Boss Shemale Pov 2

5 days ago

ShemaleZ

creampie, POV, shemale, asian
21:24

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

1 week ago

ShemaleZ

big ass, shemale, stockings, ass
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

3 months ago

ShemaleZ

threesome, nipples, office, asian, boss
38:55

Sexy boss marissa

5 years ago

TXXX

stockings, boss, shemale fucks guy
17:01

Candee Lace - Very hot maid services her boss #ROLEPLAY2018

6 years ago

HClips

teen (18+), creampie, POV, maid, blonde, boss
37:14

Latina Secretary And The Boss Have A Naughty Fling

3 years ago

HClips

mature, amateur, latina, secretary, webcam, boss
30:44

Sissy secretary lunchtime fucking by boss

5 years ago

ShemaleZ

secretary, sissy, boss
15:05

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

2 years ago

xHamster

MILF, futanari, boss
18:06

The Boss' Bathroom.

13 years ago

xHamster

bathroom, boss
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

7 months ago

ShemaleZ

fetish, asian, cumshot, gangbang, group, futanari, skirt
27:18

French TS Maid with her Boss Fuck

6 years ago

xHamster

french, maid, small tits, boss, blowjob
19:49

Black shemale boss fucks her male employee

11 years ago

xHamster

black, boss
25:16

Pretty Office Trans Cums on Desk

1 year ago

xHamster

asshole, shemale, masturbation, solo, office, boss
34:31

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

1 month ago

ShemaleZ

big ass, facial, threesome, shemale, big cock, interracial
15:39

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

3 months ago

xHamster

blowjob, office, big cock, secretary, bareback, boss, shemale fucks guy
35:05

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

3 months ago

xHamster

threesome, bareback, couple, blowjob, facial, boss
15:48

Transex Secretary Giving Her Boss

1 year ago

xHamster

blowjob, big ass, brazil, tattoo, secretary, boss
24:47

Nikki North - Transgendered Bosses 3 Scene 1 In 4k

2 years ago

ShemaleZ

lingerie, tattoo, boss
29:25

A Boss Called Her Secretary And Both Got A Superb Fucking Session In Hotel Room

2 years ago

ShemaleZ

secretary, hotel, boss
34:32

Her boss has a suprise for her

5 years ago

TXXX

boss, shemale and girl
23:55

Cute little asian maid tranny fucks the bosses nice cock

11 years ago

xHamster

maid, boss
22:21

Beautiful Trans Bareback Anal With Her New Boss With Riley Ivy

11 months ago

HClips

amateur, beauty, anal, fetish, tattoo, bareback, boss
22:38

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

1 year ago

ShemaleZ

cum in mouth, bathroom, boss, cum in ass
22:26

Chick with dick pounded by her boss

1 year ago

xHamster

stockings, boss, small tits, shemale fucks guy
38:58

Jane Marie In Boss Level

4 years ago

TXXX

boss
39:35

Boss Level

4 years ago

Upornia

big tits, boss
32:46

Transgendered Bosses

5 years ago

Upornia

boss
22:01

Aubrey Kate Boss Wife

5 years ago

TXXX

wife, boss
28:50

Tranny bonks Her Boss In Her Mind

6 years ago

ShemaleZ

boss
1:04:04

Bigg Boss Tamil - Season 2 - DAY 12

6 years ago

xHamster

boss
15:51

Cute TS Secretary with Her Boss

9 years ago

TXXX

cute, creampie, secretary, small tits, boss
40:36

She’s The Boss (shemale fuck girl)

5 years ago

TXXX

uniform, shemale and girl, boss
31:23

Transgendered Bosses 3 - Eva Maxim

2 years ago

ShemaleZ

handjob, big ass, boss
29:18

Ginger Sissy Boss (full Version)

3 years ago

ShemaleZ

redhead, webcam, boss, sissy
34:05

New Boss Office Sex Episode 2

3 years ago

Upornia

big tits, office, boss
27:12

Desi Bengali Real Wife Office Sex With Boss

3 years ago

Upornia

wife, office, boss
19:24

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

4 years ago

xHamster

blowjob, boss
40:52

Asian amateur ladyboy secretary getting fucked by her bosses

4 years ago

xHamster

teen (18+), teen anal (18+), ladyboy, secretary, boss
35:53

Gorgeous TS makes love w/ female co-worker in their Boss s office

5 years ago

TXXX

office, shemale and girl, boss
15:44

Boobed blonde fucks office boss in ass

5 years ago

ShemaleZ

uniform, office, boss, shemale fucks guy
16:57

Stgreetingss manmale Boss

5 years ago

TXXX

blowjob, boss
29:39

Boss And Her Boyfriend nailing Happily

5 years ago

ShemaleZ

boss, boyfriend
20:30

Business shemale - Boss Film

5 years ago

TXXX

blonde, vintage, boss
16:57

Stgreetingss manmale Boss

5 years ago

ShemaleZ

boss
22:16

Being dominated - Boss Film

6 years ago

ShemaleZ

BDSM, vintage, skinny, boss, domination, fetish
25:33

Playgirl In underware acquires Her ass Filled - Boss Film

6 years ago

ShemaleZ

lingerie, boss
21:05

TS Boss Barebacks Guy, Cums on His Face

6 years ago

ShemaleZ

boss, bareback
24:38

Secret lady-twink sexy Secretary Opens yummy anal For Boss

7 years ago

ShemaleZ

secretary, boss
17:09

Tranny boss sucks off her new black employee

10 years ago

xHamster

femdom, bisexual, boss
42:43

Zariah Aura In Im The Fucking Boss

1 month ago

ShemaleZ

boss, shemale
38:25

My Married Boss Fucked Me Like a Slut

7 months ago

xHamster

amateur, cute, anal, big ass, big tits, ass, bareback
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

7 months ago

ShemaleZ

asian, shemale, futanari
16:09

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

10 months ago

ShemaleZ

shemale, blowjob, big ass, outdoor, big tits, redhead, tattoo
43:42

Italian Tranny Boss Manhandles Her Personal Male Sex Slave

11 months ago

ShemaleZ

MILF, BDSM, italian, big cock, blowjob, boss
17:29

BIGGER titt rings to please my new boss.

1 year ago

xHamster

boss, shemale and girl, monster, small cock, prostitute
15:42

Transex Secretary Giving Her Boss

1 year ago

ShemaleZ

shemale, secretary, boss
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
27:34

French Ts Maid With Her Boss Fuck

1 year ago

ShemaleZ

french, maid, vintage, boss
41:38

Thai Tranny June Gets Used Dirty By Boss - BIG COCK

2 years ago

xHamster

thai, boss
38:15

American Tranny Fucks Her Boss In The Butthole

2 years ago

ShemaleZ

redhead, boss
38:14

American tranny fucks her boss in the butthole

2 years ago

xHamster

boss
18:35

Tranny bunny fucks her boss in the ass and squirts horny in her hole

2 years ago

xHamster

squirt, boss
40:36

American boss gets ass fucked by aisa tranny

2 years ago

xHamster

boss
23:02

A BBC Boss, BBC Friend, BBC footballer, and a BBC homie pound wet trans asshole

2 years ago

xHamster

big ass, wet, cartoon, asshole, BBC, boss
16:54

Female Bosses Pegging Sissy

2 years ago

ShemaleZ

domination, pegging, boss, brunette, fetish

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