TRANNY • BOSS 1,150 videos

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24:30 96%

Boss Overallsandacreampie

4 years ago

ShemaleZ

ladyboy, boss, asian, creampie, POV
41:49 94%

Yasmin Lee In Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

10 months ago

ShemaleZ

stockings, asian, BDSM, secretary, cum in mouth, domination, boss
12:27 94%

OOPSIE - Security Kasey Kei Caught Boss Izzy Wilde Fucking New Hire In Elevator & Wanna Join Them

1 year ago

TXXX

creampie, threesome, caught, masturbation, bareback, boss
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
2:09:24 92%

Shemales bosses

5 years ago

ShemaleZ

uniform, boss, shemale, blowjob
06:11 91%

My TS boss just totally put her dick in my face

2 years ago

TXXX

blowjob, ass to mouth, big cock, teacher, boss
05:35 91%

Blowing the gigantic cock of the boss to get the job - Blowjob Interview! - HQ 3D Animation

3 months ago

xHamster

3D, big cock, shemale, romanian, audition, boss
07:42 91%

Amy's Big Wish - Mandy Bear - Futanari Boss Fucks Some Ass Really Hard!

2 years ago

xHamster

creampie, cartoon, futanari, boss
05:09 90%

Shemale Boss Fucks Deep Throat Employee

3 years ago

ShemaleZ

stockings, fetish, interracial, asian, BDSM, deepthroat, domination
12:09 90%

Trans Maid Cant Resist Bosses Dick Micheal - Natalie Stone And Del Ray

3 years ago

HClips

stockings, small cock, maid, boss, small tits
22:51 89%

Riley Ivy - Beautiful Trans Bareback Anal With Her New Boss

10 months ago

ShemaleZ

beauty, anal, interracial, asian, tattoo, blonde, bareback
13:07 87%

Miran’s The Boss!

2 years ago

TXXX

japanese, boss, japanese uncensored, stockings, asian, solo
22:11 87%

Here we enjoy Boss again getting banged

4 years ago

ShemaleZ

creampie, asian, boss, POV
08:09 86%

Your Boss Is a Homewrecker

10 months ago

xHamster

solo, amateur, cheating, 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, big cock, seduced, boss, bareback, hotel
22:11 86%

Boss Blackbabydoll2creampiescloseupcum

4 years ago

ShemaleZ

creampie, POV, asian, boss, ladyboy, stockings
04:55 86%

Tanned tranny boss punishes teacher

5 years ago

HClips

teacher, boss
25:56 86%

Big shemale shows guy whos the boss

5 years ago

ShemaleZ

redhead, boss
14:34 86%

Ts Boss Fucks Her Employee In The Office With Joanna Jet

2 years ago

Upornia

office, bareback, boss, shemale fucks guy
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
13:16 83%

Big Booty Shemale Secretary Gets Fucked By Her Boss

9 months ago

ShemaleZ

secretary, big ass, shemale
05:36 83%

Trans Maid Emma Ink Fucks Her Married Boss's Virgin Ass

12 months ago

xHamster

homemade, couple, boss, shemale fucks guy, maid
06:15 83%

My big tits TS boss put her dick in my face

2 years ago

TXXX

ass to mouth, big cock, bareback, boss
05:43 83%

Shemale boss Franchezka fucking cleaning lady Nickey Huntsman

10 years ago

TXXX

boss
11:00 83%

My horny asian transgender boss is fucking me in her office

1 year ago

TXXX

asian, office, secretary, boss, small tits
24:03 83%

Transgendered Bosses 3 With Dillon Diaz And Gracie Jane

2 years ago

Upornia

stockings, fetish, big tits, lingerie, blonde, boss
15:00 83%

TRANSFIXED - OFFICE MS. CONDUCT - Hot Trans Boss Jade Venus And Jane Wilde Fuck In Front Of The Staff!

2 years ago

TXXX

office, boss
07:14 83%

Horny Secretary Inseminated By Boss!

1 year ago

ShemaleZ

stockings, secretary, boss, cumshot
12:34 83%

GenderXFilms - Trans Maid Can't Resist Boss’s Dick

3 years ago

xHamster

small cock, maid, shower, boss
17:36 83%

Sexy maid trying to satisfy her bosses

5 years ago

TXXX

maid, shemale and girl, boss, threesome, amateur
12:17 82%

TRANSFIXED - Employees Korra Del Rio & Leana Lovings Stop Boss' Assistant Zariah Aura From Snitching

1 year ago

xHamster

shemale, blowjob, shemale and girl, boss
04:41 82%

Ts Atorney With Big Cock Fuck Milf Boss - Venus Lux

3 years ago

ShemaleZ

MILF, shemale and girl, boss
21:00 82%

Secret sheboy Secretary Opens pleasant butt For Boss

7 years ago

ShemaleZ

secretary, boss
07:19 82%

Horny secretary inseminated by boss!

1 year ago

xHamster

secretary, boss
24:42 82%

Trans Love - Scene 4 - Boss Film

5 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
06:15 81%

Secretary ladyboy with big tits Tata anal pleases her boss

4 years ago

xHamster

teen (18+), teen anal (18+), ladyboy, secretary, boss, cum in mouth
2:09:24 80%

Shemales bosses

5 years ago

Upornia

shemale, blowjob, boss
14:46 80%

Doctor Boss

5 years ago

TXXX

doctor, boss
09:30 80%

Latina Trans Maid Succumbs To Boss Weenie

9 months ago

HClips

amateur, latina, big cock, boss, maid
01:11 80%

Big Boss Becomes Dungeon Anal Whore With Corbin Dallas And Jessica Fox

3 years ago

Upornia

stockings, whore, boss, shemale fucks guy, BDSM
38:57 80%

Marissa Minx Transgendered Bosses

3 years ago

ShemaleZ

MILF, boss
04:39 80%

Shemale boss anal fucks busty redhead

5 years ago

ShemaleZ

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04:41 80%

Shemale Atorney Anal Fucks Milf Boss With Venus Lux

3 years ago

ShemaleZ

MILF, shemale and girl, boss
15:13 79%

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+)
05:45 79%

Trans Babysitter Gets Anal Fucked By Her Boss With Gianna Rivera

1 year ago

TXXX

blonde, boss
05:45 79%

Shemale Babysitter Is Anal Fucked By Her Boss With Lucia Matthews

1 year ago

ShemaleZ

small cock, anal, boss
06:15 78%

Secretary ladyboy with big tits Tata pleases her boss with anal sex

4 years ago

TXXX

teen (18+), teen anal (18+), ladyboy, secretary, boss, asian
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

2 months ago

ShemaleZ

ebony, shemale, POV, big ass, interracial, MILF, office
05:40 78%

Kate Zoha - Petite Trans Babysitter Sucks And Anal By Her Boss

3 years ago

ShemaleZ

small cock, cumshot, boss
33:10 78%

Boss Skimpylingeriehjandstroke

4 years ago

ShemaleZ

POV, boss, asian
20:22 77%

Nina Lawless Xxx - Nina Lawless - Smoking Boss Bitch

3 years ago

ShemaleZ

smoking, boss, solo
13:29 77%

Mateo Tomas - Heteroflexible - Cute Femboy Maid Katie Lingeries Tight Ass Gets Used By Straight Boss

1 year ago

ShemaleZ

cute, maid, boss, femboy
05:41 77%

Horny Boss Asslicks And Barebacks The Blonde Tgirl - Emma Rose

3 years ago

TXXX

small cock, ass licking, boss, big cock
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
05:59 74%

My Boss Is A Transsexual!

6 years ago

ShemaleZ

domination, boss, shemale fucks guy
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
26:16 72%

Old boss with her tranny secretary

5 years ago

ShemaleZ

mature, creampie, fetish, outdoor, lingerie, uniform, ass to mouth
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
13:08 70%

TRANSFIXED - Security Kasey Kei & Boss Izzy Wilde Almost Caught Fucking New Hire In Office Elevator

10 months ago

xHamster

caught, shemale and girl, creampie, big ass, office
05:10 70%

Deepthroat Loving Ts Secretary Enjoys 69 With Boss In Office

2 years ago

ShemaleZ

office, 69, deepthroat, secretary, cum in mouth, boss
04:40 70%

Blonde Ts boss fucks redhead employee

5 years ago

ShemaleZ

boss
05:50 70%

Johanna Badine In Latin Milf Shemale Sucked Off And Anals Boss

1 year ago

ShemaleZ

mature, mature anal, boss, shemale fucks guy
07:05 69%

Submit To Your Boss!

1 year ago

xHamster

mature, stockings, cumshot, boss
08:35 69%

Boss Fucks Petite Trans Maid

1 year ago

xHamster

amateur, anal, maid, crossdresser, sissy, boss
26:38 69%

Indian Shemale Interview Ends In Fucking The Boss

2 years ago

Upornia

indian, shemale and girl, audition, boss
05:45 68%

Busty Shemale Boss Gets Her Ass Licked And Barebacked By Bbc

3 years ago

ShemaleZ

amateur, interracial, BBC, boss
34:35 67%

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

1 week ago

ShemaleZ

facial, interracial, big cock, threesome, shemale
23:54 67%

Tranny servant and young boss

5 years ago

ShemaleZ

lingerie, uniform, boss, blowjob, mature
12:09 67%

Stunning Trans Boss Bangs Bbc Employee - Jade Venus

2 years ago

ShemaleZ

boss, BBC
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

3 months ago

ShemaleZ

kissing, stockings, french, POV, fetish, asian, 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
06:18 67%

Strict Boss...! Warning Or Swallow Sperm?

1 year ago

ShemaleZ

sperm, swallow, boss
18:29 65%

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

2 years ago

xHamster

japanese, boss
26:42 64%

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

3 years ago

xHamster

russian, fisting, old and young (18+), food, secretary, boss, gape
15:28 64%

My Busty Fit tranny Boss owned my mouth - WickedWhims

1 year ago

xHamster

black, old and young (18+), cartoon, boss, shemale fucks guy, domination
12:59 64%

Carla Morelli - Horny Ebony Milf Gets Fucked By Her Trans Boss In The Office

4 months ago

ShemaleZ

ebony, big ass, MILF, tattoo, office, ass, boss
04:38 64%

Shemale Boss Whips And Fucks Worker

2 years ago

ShemaleZ

domination, boss
05:09 64%

Boss Cums In Her Employees Mouth

3 years ago

ShemaleZ

cum in mouth, domination, boss, cumshot
04:39 64%

Shemale boss fucks deep throat employee

5 years ago

ShemaleZ

boss
12:13 64%

TRANSFIXED - Employees Korra Del Rio & Leana Lovings Stop Boss' Assistant Zariah Aura From Snitching

1 year ago

TXXX

threesome, big cock, boss
06:01 64%

Raunchy Slender Boss Shemale Surprised A Muscular Worker With Nataly Gold

3 years ago

HClips

18, surprise, boss
08:12 63%

Trans Maid Pleasures Her New Boss

1 year ago

xHamster

maid, shemale, bareback, beauty, small tits
05:45 60%

Kenna James And Natalie Mars In Tgirl Boss Licks And Fuck Secretary

3 years ago

TXXX

secretary, boss
06:20 60%

Kasey Kei, Izzy Wilde And Big T - Milf Fucked By Tgirl Boss N Ts Security

1 year ago

ShemaleZ

stockings, MILF, shemale and girl, boss
44:41 59%

Shemale fucks hotel boss and squirts his ass

2 years ago

xHamster

handjob, squirt, asian, orgasm, japanese, 18, swallow
06:24 58%

Strict boss...! Warning or swallow sperm?

1 year ago

xHamster

shemale, blowjob, sperm, swallow, boss, shemale fucks guy
16:02 57%

Dominated By My Female Boss - Indonesian Femdom With Awek Melayu

1 year ago

ShemaleZ

femdom, indonesian, boss
04:00 55%

Casey Kisses & Dale Savage in A Helping Hand: Dale Savage Helps Relieve Stressed Boss Casey Kisses - KINK

4 years ago

TXXX

kissing, 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

4 months ago

ShemaleZ

shemale, train, anal, threesome, fetish, asian, orgasm
29:22 50%

Indian Boss Fucked Hot Shemale

1 year ago

ShemaleZ

indian, teen (18+), boss
08:12 50%

Pretty Office Trans Cums on Desk

1 year ago

xHamster

masturbation, solo, shemale, asshole
17:27 50%

Shemale Boss

9 years ago

TXXX

small tits, boss, shemale fucks guy
24:37 44%

Like a Boss

10 years ago

xHamster

boss, small tits
06:37 44%

Crossdresser lady boss is here

5 years ago

xHamster

ladyboy, boss, crossdresser
05:42 42%

My boss s shemale wife seduced me

4 years ago

ShemaleZ

wife, seduced, boss
15:54 40%

Patty crossdresser I'm your bitch boss

3 months ago

xHamster

mature, stockings, french, crossdresser, masturbation, small tits, sissy
06:15 40%

Raven-haired American Shemale Gives Bald Boss A Dick

3 years ago

ShemaleZ

pakistani, boss
06:00 17%

Mirans The Boss - TGirlJapan

4 years ago

TXXX

boss, masturbation, asian, solo
25:41 14%

Horny guys fucking hot boss

5 years ago

ShemaleZ

boss
08:15

Ill Just Replace Boss Canceled Dick Appointment

3 days ago

ShemaleZ

big cock, shemale and girl, ebony, blowjob
06:15

Fucks Her Horny Boss With Destiny Mira And Lei Lani

1 week ago

ShemaleZ

boss, ebony
34:31

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

5 days ago

ShemaleZ

big ass, facial, threesome, shemale, big cock, interracial
06:03

Gorgeous Tbabe Pool Cleaner Analed By Her Boss

5 days ago

ShemaleZ

shemale, bareback, anal
08:15

Shemale Secretary Fucking Her Lady Boss

6 days ago

ShemaleZ

ebony, ass licking, shemale and girl, boss, lingerie, secretary
05:46

Busty Milf Intern Has An Anal Threesome With Big Ass Tranny Boss 6 Min With Kasey Kei, Summer Hart And Izzy Wilde

5 days ago

ShemaleZ

anal, stockings, MILF
06:03

Black Dude Suck Ts Boss Shemeat And Fuck Her Ass

1 week ago

ShemaleZ

big tits, black, stockings
08:06

Beautiful Trans Bareback Anal With Her New Boss

9 months ago

ShemaleZ

tattoo, shemale, beauty, lingerie, boss
06:15

Lucky Boss Gets His Penis Sucks By His Helpful Maid With Große Titten

1 month ago

ShemaleZ

stockings, blowjob, maid, lingerie, ass licking, penis, boss
05:08

My boss realized I wasn't a woman

3 months ago

xHamster

couple, bondage, BDSM, group, orgy, domination, 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

6 months ago

ShemaleZ

fetish, asian, cumshot, gangbang, group, futanari, skirt
08:15

Lei Lani - Busty Ebony Tgirl Fucking Black Boss

2 weeks ago

ShemaleZ

boss, ebony, shemale, stockings, shemale and girl, black
08:06

Jade Venus - Beautiful Trans Girl Fucked Hard By Her Boss

3 years ago

TXXX

teen (18+), boss, beauty
05:05

Secretary fucking with boss in lingerie sex

5 years ago

ShemaleZ

lingerie, secretary, boss

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