SHEMALE • BOSS 3,442 videos

Popular Latest Top rated

‹1 2 3 4 5 ›

13:00 75%

Beautiful Trans Bareback Anal with Her New Boss

1 year ago

AShemaleTube

blowjob, shemale, bareback, anal, beauty, boss
06:15 75%

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

5 years ago

TXXX

teen (18+), teen anal (18+), ladyboy, secretary, boss, asian
08:16 74%

Shemale boss Jade Venus normally does not fuck her employees

3 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
05:59 73%

My Boss Is A Transsexual!

7 years ago

ShemaleZ

domination, boss, shemale fucks guy
07:00 73%

Her boss did not know that she is a shemale

11 years ago

AnyPorn

boss
23:42 73%

The Boss Adam With Erica Cherry And Sabina Steele

3 years ago

ShemaleZ

threesome, boss
26:28 73%

Shemale Maid nailed By Her shemale Boss

6 years ago

ShemaleZ

shemale, maid, uniform, boss
29:51 72%

Destiny Mira And Leilani Li - Unscheduled Meeting With The Boss

6 months ago

ShemaleZ

shemale, POV, ebony, cumshot, 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
06:18 71%

Strict Boss...! Warning Or Swallow Sperm?

1 year ago

ShemaleZ

sperm, swallow, boss
12:46 71%

Babysitter Luna Love Fucks Divorced Boss - GenderX

5 years ago

xHamster

teen anal (18+), boss, teen (18+)
24:38 71%

Secret doll-twunk gorgeous Assistant Opens saucy assfuck For Manager

5 years ago

TrannyGem

doll, office, boss, ladyboy, cute
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
06:16 70%

Mom intern 3some orgy with shemale boss

4 months ago

XoZilla

threesome, orgy, mature, mom, anal, 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
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
08:41 70%

Futanari ebony boss fucking her maid in the ass

4 years ago

TrannyOne

maid, anime, futanari, boss
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
04:40 67%

Blonde Ts boss fucks redhead employee

6 years ago

ShemaleZ

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
05:34 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
15:51 67%

Cute TS Secretary with Her Boss

10 years ago

TXXX

cute, creampie, secretary, small tits, boss
05:19 67%

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

6 months ago

VideoSection

boots, maid, 3D, anime, futanari, 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
10:08 67%

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

1 year 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
15:39 67%

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

9 months ago

xHamster

blowjob, office, big cock, secretary, bareback, 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
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
15:54 63%

Patty crossdresser I'm your bitch boss

10 months ago

xHamster

mature, stockings, french, crossdresser, masturbation, sissy, boss
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
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
05:36 60%

Transsexual assistant in pantyhose banging boss

3 years ago

ShemaleTaxi

pantyhose, domination, boss, hardcore
06:24 58%

Strict boss...! Warning or swallow sperm?

2 years ago

xHamster

shemale, blowjob, sperm, swallow, boss, shemale fucks guy
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
27:16 57%

Young Boss exposes his older secretary to a lustful slut!

4 years ago

TrannyOne

mature, secretary, slut, boss, shemale
22:07 57%

Curvaceous double cock Latina futa dominates and fucks her boss

8 years ago

TrannyOne

domination, futanari, boss, double penetration
26:29 56%

Riley Storm Assistant Pummel

5 years ago

TrannyGem

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

2 years ago

AnySex

stockings, big ass, big tits, maid, uniform, compilation, small tits
2:14:08 53%

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
17:27 53%

Shemale Boss

9 years ago

TXXX

small tits, boss, shemale fucks guy
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

6 months ago

ShemaleZ

shemale, lesbian, asian, crossdresser, shemale and girl, girlfriend, skirt
29:22 50%

Indian Boss Fucked Hot Shemale

2 years ago

ShemaleZ

indian, teen (18+), boss, shemale fucks guy
06:09 50%

Trendy trans chief assfucks sissy secretary

3 years ago

TrannyGem

secretary, sissy, boss
05:05 50%

Secretary fucking with boss in lingerie sex

6 years ago

ShemaleZ

lingerie, secretary, 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
06:00 50%

Ladyboy seduced by future boss big cock fucking and cumshot

6 years ago

TrannyGem

seduced, boss
12:15 50%

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

2 months ago

ShemaleMovie

double anal, handjob
55:22 50%

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
06:15 40%

Raven-haired American Shemale Gives Bald Boss A Dick

3 years ago

ShemaleZ

pakistani, boss
05:11 40%

Big Tittied Blonde Boss TS Dominated

11 years ago

AShemaleTube

shemale and girl, domination, 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

8 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

4 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
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
06:40 13%

Big breasted boss ass fucked by fat cock hermaphroditism

4 months ago

ShemaleMovie

big cock, futanari, fat, big tits, machine, boss
01:58

Hot trans girl twerking for her boss

2 weeks ago

AShemaleTube

homemade, creampie, solo, masturbation, big cock, boss
05:54

Trans Maid Is Impressed By Boss Big Cock

3 weeks ago

BeMyHole

ass, maid, small cock, hardcore, big cock, riding
05:01

BBC Boss Spanks His BIG ASS Trans Secretary.

1 week ago

BeMyHole

boss, interracial, BBC, shemale, secretary, big cock, spanking
15:02

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

3 weeks ago

AShemaleTube

anal, big ass, blowjob, big cock, boss, shemale
05:52

Im Rubbing My Dick Ifo My Hot Tgirl Boss

3 weeks ago

BeMyHole

big cock, blowjob, boss
06:15

Boss caught TS babysitter having sex in his house

1 week ago

AShemaleTube

boss, caught
08:00

Facial Act Sunshyne Monroe Fucks The Boss

2 weeks ago

xShemaleTube

shemale, facial, shemale fucks guy, interracial
25:16

Pretty Office Trans Cums on Desk

1 year ago

xHamster

asshole, shemale, masturbation, solo, office, boss
05:07

TS dominates her boss in office affair

5 days ago

AShemaleTube

shemale, bareback, shemale fucks guy, blowjob
04:00

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

2 months ago

Fuxxx

BDSM, handjob, boss, office
05:18

Bearded masculine ass fucking fucked by she-creature boss

3 months ago

ShemaleTaxi

domination, shemale fucks guy, 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

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

1 week ago

GetTranny

boss, outdoor, hardcore, public
10:00

Ebony shemale shows her white bf who is the boss

1 month ago

AShemaleTube

compilation, shemale fucks guy, interracial, homemade, ebony
13:57

Cis Boss Gets Public Free Use Creampied

2 months ago

AShemaleTube

creampie, public
22:18

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

6 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
07:59

Aphrodite Adams - Bimbo Transgender Maid Served By Her Boss Bareback

2 days ago

PePorn

big cock, shemale, nylon, bareback
02:38

Horny Latina showing her boss how to masturbate

1 week ago

AShemaleTube

amateur, big cock, sissy, masturbation, homemade, solo
05:57

TS Izzy Wilde Barebacks Coworker As Boss Fucks Her In 3some

3 years ago

BeMyHole

stockings, fetish, lingerie, office, blonde, ass, deepthroat

Popular Latest Top rated

‹1 2 3 4 5 ›

Popular categories

Other free porn sites

All models were 18 years of age or older at the time of depiction. ShemaleMap.com has a zero-tolerance policy against illegal pornography.

Disclaimer: ShemaleMap.com is just a search engine. All links and thumbnails displayed on this website are added automatically. We do not own, produce, host or upload any videos displayed on this website, we only link to them.
To remove physical video file please contact owner of the website where it hosted. To remove the link and thumbnail from this website please use the report button () which is located under each video.

ShemaleMap.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering.

Copyright © 2022 ShemaleMap.com. All rights reserved. | Abuse