SHEMALE • BOSS 3,423 videos

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08:16 74%

Shemale boss Jade Venus normally does not fuck her employees

2 months ago

KeekAss

handjob, boss, blowjob, ass licking
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
41:33 74%

Shes The Boss

4 years ago

TrannyOne

shemale, office, 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
07:00 73%

Her boss did not know that she is a shemale

11 years ago

AnyPorn

boss
05:59 73%

My Boss Is A Transsexual!

7 years ago

ShemaleZ

domination, boss, shemale fucks guy
23:42 73%

The Boss Adam With Erica Cherry And Sabina Steele

3 years ago

ShemaleZ

threesome, 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

10 months ago

ShemaleZ

kissing, stockings, french, POV, asian, boss
50:05 71%

Hot Latina Secretaries Abuse And Dominate Their Boss

4 years ago

TrannyOne

shemale, secretary, boss, threesome
24:38 71%

Secret doll-twunk gorgeous Assistant Opens saucy assfuck For Manager

5 years ago

TrannyGem

doll, office, boss, ladyboy, cute
06:18 71%

Strict Boss...! Warning Or Swallow Sperm?

1 year ago

ShemaleZ

sperm, swallow, boss
11:36 71%

The Little Sissy Maid Dienstmadchen for The Boss

3 years ago

xHamster

latex, german, maid, boss
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
50:37 71%

Horny Mature Secretary Turns Her Boss Into A Submissive Bitch

4 years ago

BeMyHole

mature anal, office, secretary, boss, shemale fucks guy
29:51 71%

Destiny Mira And Leilani Li - Unscheduled Meeting With The Boss

6 months ago

ShemaleZ

shemale, POV, ebony, cumshot, boss
05:50 70%

Johanna Badine In Latin Milf Shemale Sucked Off And Anals Boss

2 years ago

ShemaleZ

mature, mature anal, boss, shemale fucks guy
08:41 70%

Futanari ebony boss fucking her maid in the ass

4 years ago

TrannyOne

maid, anime, futanari, boss
15:01 70%

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

3 years ago

TXXX

cartoon, futanari, boss, solo
08:01 70%

Pregnant mom and boss's daughter Step Into My Shower

4 years ago

TrannyOne

mom, pregnant, stepmom, shower, boss
06:25 69%

Strict boss...! Warning or swallow sperm?

1 year ago

TrannyOne

big ass, amateur, swallow, sperm, boss
29:28 69%

Indian Boss Fucked Hot Shemale

2 years ago

xHamster

indian, anal, big ass, ladyboy, shemale fucks guy, asian
05:08 68%

Crossdresser takes trannys chopper up his rear end

6 years ago

XoZilla

maid, uniform, boss
05:45 68%

Busty Shemale Boss Gets Her Ass Licked And Barebacked By Bbc

3 years ago

ShemaleZ

amateur, interracial, BBC, boss
15:13 68%

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

3 years ago

Upornia

amateur, teen (18+), asian, maid, crossdresser, sissy, boss
06:16 67%

Mom intern 3some orgy with shemale boss

3 months ago

XoZilla

threesome, orgy, mature, mom, anal, boss
06:15 67%

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

8 months ago

ShemaleZ

stockings, blowjob, maid, lingerie, ass licking, penis, boss
05:19 67%

Ebony Futa Boss Anal Fuck thick bum Maid - Sassycomics.mp4

5 months ago

VideoSection

boots, maid, 3D, anime, futanari, boss
04:40 67%

Blonde Ts boss fucks redhead employee

6 years ago

ShemaleZ

boss
15:51 67%

Cute TS Secretary with Her Boss

10 years ago

TXXX

cute, creampie, secretary, small tits, boss
05:34 67%

BBC boss smacks his humungous booty trans secretary.

2 months ago

ShemaleTaxi

3D, cartoon
12:59 67%

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

11 months ago

ShemaleZ

ebony, big ass, MILF, tattoo, office, boss
36:36 67%

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

4 years ago

TrannyOne

office, boss
11:50 67%

GenderX - Trans Boss Fucked in Office after Hours

5 years ago

BeMyHole

office, boss
34:35 67%

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

7 months ago

ShemaleZ

handjob, threesome, couple, interracial, MILF, facial, ass licking
15:39 67%

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

8 months ago

xHamster

blowjob, office, big cock, secretary, bareback, boss
10:08 67%

Hot Maid TRANS Melyna Merli Fucked By The Boss While His Wife Works - Monster Cock - Yago Ribeiro

12 months ago

BeMyHole

maid, monster, boss, ass licking
11:01 67%

Genderx - Man Banged By Trans Boss To Save His Job

5 years ago

TXXX

gangbang, boss
06:20 67%

Hijab woman get pound three dimensional

1 year ago

TrannyGem

lesbian, arab, cartoon, asian, domination
06:01 66%

Raunchy Slender Boss Shemale Surprised A Muscular Worker With Nataly Gold

4 years ago

HClips

18, surprise, boss
41:33 65%

Shes The Boss Kenna James and shemale

5 years ago

Analdin

office, babe, erotic, boss, romantic
04:39 64%

Shemale boss fucks deep throat employee

6 years ago

ShemaleZ

boss
28:50 64%

Lewd Secretaries gang Up On Their penis Manager

4 years ago

TrannyGem

office, gangbang, secretary, cum in mouth, domination, penis, boss
04:38 64%

Shemale Boss Whips And Fucks Worker

3 years ago

ShemaleZ

domination, boss
05:42 63%

Tall imperious shemale rectal bangs her boss

6 years ago

HDSex

tall, domination
08:12 63%

Trans Maid Pleasures Her New Boss

1 year ago

xHamster

maid, shemale, bareback, beauty, small tits, boss
05:09 62%

Blond Hair Babe Ts boss fucks redhead employee

6 years ago

XoZilla

latex, anal, fetish, bondage, BDSM, redhead, ladyboy
05:35 62%

She-male secretary buttfuck tears up her boss

8 months ago

ShemaleTaxi

hardcore, shemale, boss, ladyboy
26:53 60%

Cute Cunt Serving Her Boss

3 months ago

HClips

cute, shemale, amateur, cumshot
06:16 60%

Big Tits Trans Babysitter Gets A Bj By Boss With Morgan Bailey

2 months ago

PePorn

granny, office
07:33 60%

A Young Miner Trans Was Caught By Surprise When The Boss Began To Pester Her And Hard Fuck Right On The Spot 12 Min

2 years ago

GetTranny

caught, shower, surprise, boss, japanese uncensored
05:36 60%

Transsexual assistant in pantyhose banging boss

3 years ago

ShemaleTaxi

pantyhose, domination, boss, hardcore
12:34 60%

Pink Haired Trans Maid Catches Boss Jerking

3 years ago

TXXX

small cock, maid, caught, 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
06:24 58%

Strict boss...! Warning or swallow sperm?

2 years ago

xHamster

shemale, blowjob, sperm, swallow, boss, shemale fucks guy
15:54 57%

Patty crossdresser I'm your bitch boss

10 months ago

xHamster

mature, stockings, french, crossdresser, masturbation, sissy, boss
11:14 57%

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

6 months ago

ShemaleMovie

handjob, beauty, french, BDSM, prostitute, babe, teacher
22:07 57%

Curvaceous double cock Latina futa dominates and fucks her boss

8 years ago

TrannyOne

domination, futanari, boss, double penetration
27:16 57%

Young Boss exposes his older secretary to a lustful slut!

4 years ago

TrannyOne

mature, secretary, slut, boss, shemale
57:21 56%

Horny latina secretaries enslave and dominate their boss

4 years ago

AShemaleTube

mature, fetish, uniform, cumshot, group, secretary, domination
49:49 56%

Horny latina secretary seduces and dominates her weenie boss

4 years ago

TrannyOne

secretary, boss, office, seduced
42:51 55%

Horny latina secretary gives it to her boss good and hard

4 years ago

AShemaleTube

mature, homemade, secretary, domination, webcam, boss, shemale fucks guy
26:29 55%

Riley Storm Assistant Pummel

5 years ago

TrannyGem

creampie, office, old and young (18+), secretary, boss, anal, amateur
06:58 55%

Sexy secretary Kassondra Raine enjoys sex with boss tranny lady Kelli Lox

5 years ago

BravoTube

secretary, boss
16:02 54%

Dominated By My Female Boss - Indonesian Femdom With Awek Melayu

1 year ago

ShemaleZ

femdom, indonesian, boss
24:51 54%

Exciting Compilation With the Sexiest Trans Maids Enjoying Their Bosses Dicks

1 year ago

AnySex

stockings, big ass, big tits, maid, uniform, compilation, small tits
17:27 53%

Shemale Boss

9 years ago

TXXX

small tits, boss, shemale fucks guy
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

6 months ago

ShemaleZ

shemale, lesbian, asian, crossdresser, shemale and girl, girlfriend, skirt
2:14:08 50%

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

2 months ago

ShemaleZ

shemale, lesbian, POV, threesome, asian, crossdresser, girlfriend
05:05 50%

Secretary fucking with boss in lingerie sex

5 years ago

ShemaleZ

lingerie, secretary, boss
06:09 50%

Trendy trans chief assfucks sissy secretary

3 years ago

TrannyGem

secretary, sissy, boss
29:22 50%

Indian Boss Fucked Hot Shemale

2 years ago

ShemaleZ

indian, teen (18+), boss, shemale fucks guy
12:15 50%

Transfixed - workers Korra Del Rio & Leana Lovings Stop Boss secretary Zariah Aura From Snitching

2 months ago

ShemaleMovie

double anal, handjob
06:00 50%

Ladyboy seduced by future boss big cock fucking and cumshot

6 years ago

TrannyGem

seduced, boss
06:26 50%

Dicky Office Girl Tata Hels Her Boss To Cum

2 years ago

DrTuber

blowjob, POV, ladyboy, office, boss, shemale and girl
55:22 48%

Lesbian training by female boss and used as a toy

2 years ago

JizzBunker

shemale, lesbian, train, japanese, boss, japanese lesbian
2:01:54 47%

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

11 months ago

ShemaleZ

train, anal, threesome, fetish, asian, orgasm, big tits
17:19 47%

Slim ladyboy maid tops her boss

4 years ago

AShemaleTube

homemade, asian, maid, uniform, boss, shemale fucks guy
24:37 44%

Like a Boss

10 years ago

xHamster

boss, small tits
05:11 40%

Big Tittied Blonde Boss TS Dominated

11 years ago

AShemaleTube

shemale and girl, domination, boss
06:15 40%

Raven-haired American Shemale Gives Bald Boss A Dick

3 years ago

ShemaleZ

pakistani, boss
06:15 40%

Trans babysitter bareback fucked by her boss!

5 months ago

AShemaleTube

bareback
05:31 40%

Sometimes You Got To Fuck The Boss With Eva Paradise

2 years ago

ShemaleZ

big cock, boss, shemale fucks guy
08:25 38%

Big-boobed ebony tgirl Leilani Li romping black boss destiny Mira

7 months ago

ShemaleMovie

ebony, black, shemale, secretary
07:47 38%

Super-naughty ladyboy pulverizes her boss to keep her job

3 years ago

ShemaleTaxi

big ass, cartoon, taxi, boss
07:36 33%

TEXT TO SPEECH fellow bosses sa8die in couch

7 months ago

TrannyGem

amateur, mature, mom
08:15 33%

Job interview at free use workplace where the boss is fucked

3 months ago

KeekAss

shemale, shemale and girl, audition
11:13 33%

Chrissina Lovegag In: Ultra Buxom Boss-Lady Bound and Gagged!

3 years ago

TrannyOne

gagging, boss
04:40 30%

Black Ts Boss Fucks Employee In Hotel - Sasha Strokes

4 years ago

ShemaleZ

black, hotel, boss, interracial
06:40 22%

Boss is probing My boundaries : The Thickening

6 months ago

ShemaleMovie

3D, futanari, cartoon, shemale fucks guy, black
07:59 20%

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

2 months ago

xShemaleTube

shemale, lesbian, threesome, asian, crossdresser, seduced, boss
21:34 20%

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

2 months ago

ShemaleTaxi

swinger, spanish, big ass, BBW, office, caught, aunt
05:35 20%

Huge-titted super-sexy ladyboy anal fucks boss

5 years ago

HDSex

boss
10:32 14%

Fetish femdom lesbian sex in office with busty blonde lesbian boss

1 year ago

xTits

femdom, blowjob, lesbian, fetish, big tits, office, natural
25:41 14%

Horny guys fucking hot boss

6 years ago

ShemaleZ

boss
06:40 13%

Big breasted boss ass fucked by fat cock hermaphroditism

3 months ago

ShemaleMovie

big cock, futanari, fat, big tits, machine, boss
15:07 13%

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

7 months ago

Beeg

lesbian, POV, anal, maid, ladyboy, cum in mouth, asshole
01:58

Hot trans girl twerking for her boss

6 days ago

AShemaleTube

big ass, solo, big cock, amateur, masturbation, shemale and girl, homemade
05:54

Trans Maid Is Impressed By Boss Big Cock

1 week ago

BeMyHole

ass, maid, small cock, hardcore, big cock, riding
08:00

Facial Act Sunshyne Monroe Fucks The Boss

5 days ago

xShemaleTube

shemale, facial, shemale fucks guy, interracial
15:02

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

2 weeks ago

AShemaleTube

anal, big ass, blowjob, big cock, boss, shemale
15:18

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

3 weeks ago

SomePorn

shemale, dogging, office, facial, shemale and girl, caught, deepthroat
05:52

Im Rubbing My Dick Ifo My Hot Tgirl Boss

2 weeks ago

BeMyHole

big cock, blowjob, boss
02:38

Horny Latina showing her boss how to masturbate

4 days ago

AShemaleTube

amateur, big cock, sissy, masturbation, homemade, solo
25:16

Pretty Office Trans Cums on Desk

1 year ago

xHamster

asshole, shemale, masturbation, solo, office, boss
08:06

Christian Xxx - He Used To Be The Boss But Not Anymore

1 month ago

ShemaleZ

ass, ass to mouth, bareback, boss, big ass
08:00

Office Boss Lover

1 month ago

xShemaleTube

shemale, amateur, office
07:38

Sissy secretary woring at home gets pegged by femdom boss

4 years ago

AShemaleTube

mature, femdom, redhead, crossdresser, shemale and girl, secretary, pegging
05:06

Huge tits TS Sarina Dominates Her Boss

3 weeks ago

AShemaleTube

boss, shemale fucks guy
05:18

Bearded masculine ass fucking fucked by she-creature boss

2 months ago

ShemaleTaxi

domination, shemale fucks guy, boss
07:39

Kinky ladyboy plumbs her boss to keep her job

2 months ago

ShemaleTaxi

futanari, cartoon, ladyboy, 18, anime
06:16

On Your Knees And Suck Your Tgirl Boss - Big T, Jane Dee And Gracie Jane

3 months ago

ShemaleZ

stockings, shemale, interracial, tattoo, blonde, bareback
06:21

Older shemale boss having anal romp in the office with worker - Nikki perverse

1 month ago

ShemaleMovie

stockings, anal, office
22:18

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

5 months ago

ShemaleMovie

shemale and girl, shemale, boss, maid
08:00

Big Booty Shemale Secretary Gets Fucked By Her Boss

1 year ago

GetTranny

shemale, big ass, big tits, stockings, boss, secretary
03:34

On the desk of Boss

3 years ago

xHamster

mature, secretary, JOI, boss
05:42

Horny Employee And Tranny Boss

1 month ago

Fuxxx

big cock, office, boss
04:00

A Helping Hand: Dale Savage Helps Relieve Stressed Boss Casey Kisses

2 months ago

Fuxxx

BDSM, handjob, boss, office
03:07

I'm Stroking my Boss's Dick under the table

2 years ago

xHamster

public, latex, voyeur, mature anal, MILF, boss
06:15

Bubble butt Thai femboy teen Boss POV handjob and big ass fucking

2 weeks ago

AShemaleTube

amateur, teen (18+), thai, POV, interracial, asian, teen anal (18+)
04:48

Horny Tranny Boss Aubrey Fucks Ruckus

1 month ago

Fuxxx

shemale, boss, office

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