Secretary Videos - Trans (6,945)

HOT Trans Assistant Lets Boss Freeuse On His Bday - Cliff Jensen, Brittney Kade

HOT Trans Assistant Lets Boss Freeuse On His Bday - Cliff Jensen, Brittney Kade

XVideos 1 year ago

Trans Woman Boss Analed By Guy Secretary

Trans Woman Boss Analed By Guy Secretary

AbTranny 10 months ago

Secretary Masturbates, Pees, Fucks A Toy and Cums At Office

Secretary Masturbates, Pees, Fucks A Toy and Cums At Office

XVideos 1 year ago

Stressed and overworked Secretary suck hung Futanari studhorse to destress // VRChat Fur Oral ERP

Stressed and overworked Secretary suck hung Futanari studhorse to destress // VRChat Fur Oral ERP

ShemaleSin 10 months ago

Stressed out boss gets his secretary's helping hand, mouth, and wet pussy

Stressed out boss gets his secretary's helping hand, mouth, and wet pussy

Some.Porn 11 months ago

Melissa Stratton wears lingerie to screw married boss

Melissa Stratton wears lingerie to screw married boss

Some.Porn 11 months ago

Crossdresser in Cum-filled Shoes

HD 0:39 / 11:18

Crossdresser in Cum-filled Shoes

FapHouse 10 months ago

Hot Busty Office Shemale Babe Jerks at Live Cam

Hot Busty Office Shemale Babe Jerks at Live Cam

MyLust 5 years ago

My TS Secretary Is Craving For My Big Dick

My TS Secretary Is Craving For My Big Dick

BeMyHole 10 months ago

MESMERIZED - OFFICE MS. CONDUCT - Jane Wilde, Ariel Demure, Emma Rose, Kira Noir, And Ember Snow

MESMERIZED - OFFICE MS. CONDUCT - Jane Wilde, Ariel Demure, Emma Rose, Kira Noir, And Ember Snow

TrannyGem 10 months ago

Crossdresser secretary in a cute flower dress for summer

Crossdresser secretary in a cute flower dress for summer

XVideos 1 year ago

Your Secretary Is Craving Cock

Your Secretary Is Craving Cock

Clips4sale 1 year ago

RHT hose and pink doxy boots

RHT hose and pink doxy boots

ShemaleSin 1 year ago

Black boss orders her ebony TS secretary Leilani Li to bang her darksome cunt

Black boss orders her ebony TS secretary Leilani Li to bang her darksome cunt

ShemaleSin 1 year ago

Shemale Secretary Thaysa Carvalho Strokes At Work

Shemale Secretary Thaysa Carvalho Strokes At Work

Dafreeporn 1 year ago

Cockhungry nanny pounded by boss

Cockhungry nanny pounded by boss

Some.Porn 10 months ago

”T-girl Yasmin Lee humiliates her sexist boss Lucas Knight with her shaft”

”T-girl Yasmin Lee humiliates her sexist boss Lucas Knight with her shaft”

Trashreality 10 months ago

Горячий фембой Hattabi4ik сквирт удовольствие

Горячий фембой Hattabi4ik сквирт удовольствие

XNXXGold 1 year ago

cd femboy in secretary outfit first time using anal til cumming

cd femboy in secretary outfit first time using anal til cumming

RedTube Unknown

Ebony FUTA enjoying her New Secretary riding her BIG BLACK COCK - 3D Animation. Clip 1

Ebony FUTA enjoying her New Secretary riding her BIG BLACK COCK - 3D Animation. Clip 1

XHamster 1 year ago

Hung Trans Girl Secretary Job Interview - Jessica Bloom

Hung Trans Girl Secretary Job Interview - Jessica Bloom

XHamster 1 year ago

TS secretary with huge jugs cums inside her skirt

TS secretary with huge jugs cums inside her skirt

AShemaleTube 1 year ago

Busty Business - S16:E10

Busty Business - S16:E10

Some.Porn 1 year ago

USA-Tob084

Some.Porn 1 year ago

This Beautiful Babe has Huge Tits and a Pretty face, with a Mouth that Knows How to Blowjob

Premium HD 1:14:54

This Beautiful Babe has Huge Tits and a Pretty face, with a Mouth that Knows How to Blowjob

Sheer 2 years ago

ADRIAN ROSE - New Recruit

ADRIAN ROSE - New Recruit

Some.Porn 1 year ago

Hung Trans Gal Secretary Job Interview - Jessica Bloom

Hung Trans Gal Secretary Job Interview - Jessica Bloom

ShemaleSin 11 months ago

Trans secretary gets barebacked by her bald boss

Trans secretary gets barebacked by her bald boss

YepTube 1 year ago

AB101 Dirty officer was trained in hell by assistant -Ten vibrators淫荡女上司被下属地狱调教-十颗跳蛋,极限高潮

AB101 Dirty officer was trained in hell by assistant -Ten vibrators淫荡女上司被下属地狱调教-十颗跳蛋,极限高潮

AShemaleTube 1 year ago

Sexy secretary in tan stockings and miniskirt cums for your pleasure

HD 1:01 / 16:15

Sexy secretary in tan stockings and miniskirt cums for your pleasure

FapHouse 3 years ago

Hot Lauryn May pussy eaten by horny stud

HD 1:01 / 20:40

Hot Lauryn May pussy eaten by horny stud

FapHouse 4 years ago

Futa girl harassing co-worker

60% 1:01 / 11:17

Futa girl harassing co-worker

FapHouse 3 years ago

Crossdressing secretary cums in her panties

66% HD 1:01 / 12:05

Crossdressing secretary cums in her panties

FapHouse 5 years ago

Naughty secretary 6

HD 1:01 / 16:24

Naughty secretary 6

FapHouse 6 years ago

Hot secretary in red gets ass fucked by her boss

HD 1:01 / 26:27

Hot secretary in red gets ass fucked by her boss

FapHouse 7 years ago

Plaid office skirt with a black half slip

Plaid office skirt with a black half slip

XHamster 1 year ago

Close Up Cumshot

Close Up Cumshot

Clips4sale 1 year ago

Naughty secretary apprentice gets big cock in her ass

Naughty secretary apprentice gets big cock in her ass

An4lPorn 2 years ago

The secretary is a slut

The secretary is a slut

XHamster 1 year ago

Sissy Secretary: Submissive Male Feminized Into Bimbo for Job Interview, Learns How to Pee Like a Girl, Bonus Pegging & Fisting

52% HD 1:01 / 8:31

Sissy Secretary: Submissive Male Feminized Into Bimbo for Job Interview, Learns How to Pee Like a Girl, Bonus Pegging & Fisting

FapHouse 1 year ago

Crossdresser Secretary Tease

Crossdresser Secretary Tease

FapHouse 1 year ago

sissy shemale Sofija 2025 dump

sissy shemale Sofija 2025 dump

XHamster 1 year ago

Sexy Blonde Softcore

Sexy Blonde Softcore

Some.Porn 1 year ago

”My transgender assistant gives me birthday ass pumping”

”My transgender assistant gives me birthday ass pumping”

HQBang 1 year ago

Sissy Secretary Big Cum

57% HD 0:39 / 0:46

Sissy Secretary Big Cum

FapHouse 1 year ago

Sissy Foot Fetish Job Interview Clip - Footjob And Fellatio Training Chastity Floozy Jessica Bloom

Sissy Foot Fetish Job Interview Clip - Footjob And Fellatio Training Chastity Floozy Jessica Bloom

ShemaleSin 1 year ago

TS Knockout Bianca Meirelles Unloads for Machine

TS Knockout Bianca Meirelles Unloads for Machine

Some.Porn 1 year ago

video of application as horny secretary girl 2 ride hug

video of application as horny secretary girl 2 ride hug

Eporner 1 year ago

Crossdressing secretary

Crossdressing secretary

ShemaleSin 1 year ago

72 the Secretary Is Back! Deepthroating Huge Cocks and Fuckin'em so Deep! - Beingboth

HD 0:39 / 27:37

72 the Secretary Is Back! Deepthroating Huge Cocks and Fuckin'em so Deep! - Beingboth

FapHouse 1 year ago

Tbabe Boss Kasey Kei Fucks Her Hot Secretary

Tbabe Boss Kasey Kei Fucks Her Hot Secretary

BeMyHole 1 year ago

Secretary - Red Skirt

63% HD 0:08 / 0:39

Secretary - Red Skirt

FapHouse 1 year ago

Amateur gloryhole DILF banged in private home after BJ

Amateur gloryhole DILF banged in private home after BJ

Some.Porn 1 year ago

Machine-fucked trans in solo affair

Machine-fucked trans in solo affair

Some.Porn 1 year ago

”Ebony tbabe Leilani Li fucks her boss”

”Ebony tbabe Leilani Li fucks her boss”

4Wank 1 year ago

The Secretaries Threesome

The Secretaries Threesome

Some.Porn 1 year ago

Horny Secretary

Horny Secretary

FapHouse 1 year ago

”Transgender assistant fucking her lady boss”

”Transgender assistant fucking her lady boss”

4Wank 1 year ago

Ladyboy secretary mouth and assfucked bareback

Ladyboy secretary mouth and assfucked bareback

Analdin 1 year ago

Hot Crossdresser's Slow Punishment

62% HD 0:39 / 19:59

Hot Crossdresser's Slow Punishment

FapHouse 1 year ago

Slutty Secretary Tranny Grazyeli Silva fucked by 2 cocks with DAP

Premium HD 48:58

Slutty Secretary Tranny Grazyeli Silva fucked by 2 cocks with DAP

Sheer 2 years ago

Tranny secretary messy masturbation

Tranny secretary messy masturbation

AShemaleTube 1 year ago

Big-tits TS Foxxy fist fucked the gaping asshole of brunette Marcelo

Big-tits TS Foxxy fist fucked the gaping asshole of brunette Marcelo

Sheshaft 1 year ago

Thinking Of Will

Thinking Of Will

Clips4sale 1 year ago

Tranny Ping gets butt plugged by soapy dick

Tranny Ping gets butt plugged by soapy dick

XHamster 1 year ago

Lascivious TS secretary Kasey Kei gives her boss a oral inside his office.In return,her boss licks her booty 1st to makes it juicy

Lascivious TS secretary Kasey Kei gives her boss a oral inside his office.In return,her boss licks her booty 1st to makes it juicy

ShemaleSin 1 year ago

Horny Little Secretary Touching Herself

HD 0:39 / 14:28

Horny Little Secretary Touching Herself

FapHouse 1 year ago

”Heavy office slut with glasses licked & loved”

”Heavy office slut with glasses licked & loved”

ThePornstar 1 year ago

Office Anal With Busty Ladyboy Secretary

Office Anal With Busty Ladyboy Secretary

BeMyHole 1 year ago

Petite TS secretary craves for boss big hard dick

Petite TS secretary craves for boss big hard dick

AShemaleTube 1 year ago

Office Rivals a Porn Game Where I Fuck a Office Worker in the Office in the Ass

HD 1:01 / 1:31:08

Office Rivals a Porn Game Where I Fuck a Office Worker in the Office in the Ass

FapHouse 1 year ago

”MyTinyWish: Bored belle tempts her boss into hard assfucking on the couch”

”MyTinyWish: Bored belle tempts her boss into hard assfucking on the couch”

ThePornstar 1 year ago

Corporate boss savagely drills his transgender secretary Brittney Kade

Corporate boss savagely drills his transgender secretary Brittney Kade

Fetishpapa 1 year ago

Your Secretary

AShemaleTube 1 year ago

this babemale Supah captivating t-model Assistant porked!

this babemale Supah captivating t-model Assistant porked!

TransTube.tv 1 year ago

Horny Secretary

HD 1:01 / 12:16

Horny Secretary

FapHouse 1 year ago

Horny Secretary

Horny Secretary

FapHouse 1 year ago

Crossdresser Begs and Jerks off in Humiliation

Crossdresser Begs and Jerks off in Humiliation

FapHouse 1 year ago

Crossdresser Begs and Jerks off in Humiliation

Crossdresser Begs and Jerks off in Humiliation

FapHouse 1 year ago

I ran into Matt and his brother Tom, as they were traveling through the city. They did a Buddies movie together, before Matt moved on and Tom stayed in Atlanta for a while. Both are very quiet and difficult to read.

I ran into Matt and his brother Tom, as they were traveling through the city. They did a Buddies movie together, before Matt moved on and Tom stayed in Atlanta for a while. Both are very quiet and difficult to read.

Some.Porn 1 year ago

Boss gives his big booty trans secretary his long thick long BBC

Boss gives his big booty trans secretary his long thick long BBC

XHamster 4 years ago

Sissygasm at the Office

Sissygasm at the Office

TrannyGem 4 years ago

Frustrated shemale boss Natalie Mars fucked teen secretary Kenna James

Frustrated shemale boss Natalie Mars fucked teen secretary Kenna James

Pervclips 3 years ago

Shemale secretary fucked in the office

Shemale secretary fucked in the office

VivaTube 5 years ago

Sensual sexy secretary mastubation and cumshot

HD 0:39 / 18:30

Sensual sexy secretary mastubation and cumshot

FapHouse 3 years ago

Transgender secretary gets horny in the office, shooting her thick load

Transgender secretary gets horny in the office, shooting her thick load

FapHouse 3 years ago

”Introverted secretary getting screwed by tranny boss - Kenna James & Natalie Mars”

”Introverted secretary getting screwed by tranny boss - Kenna James & Natalie Mars”

Faptor 3 years ago

Big boobs Asian t-girl secretary Tata anal fucked in the office

Big boobs Asian t-girl secretary Tata anal fucked in the office

Tranny.one 4 years ago

Huge tits secretary gets fucked

Huge tits secretary gets fucked

Tranny.one 4 years ago

Pantyhose Ts Tgirl Alina Pantyhose Sex With Fan And Cum Hard

Pantyhose Ts Tgirl Alina Pantyhose Sex With Fan And Cum Hard

Tranny.one 4 years ago

Office secretary

Office secretary

ShemaleSin 4 years ago

Shemale boss licks and fucks new secretary applicants pussy

Shemale boss licks and fucks new secretary applicants pussy

Pornwhite 3 years ago

Sexy Girl Masturbates Wet Pussy With Sex Toys In Office

Premium HD 13:42

Sexy Girl Masturbates Wet Pussy With Sex Toys In Office

XNXXGold 4 years ago

In secretary's uniform

In secretary's uniform

XHamster 3 years ago

More camming stream for you guys :)

More camming stream for you guys :)

XHamster 4 years ago

I Am In Love With My New Buttplug

HD 0:11 / 21:32

I Am In Love With My New Buttplug

Clips4sale 4 years ago

Transsexual Secretary Nutty Ass Barebacked And Blows Dick

Transsexual Secretary Nutty Ass Barebacked And Blows Dick

Eporner 3 years ago

My Teen Secretary No Panty in Office

My Teen Secretary No Panty in Office

ShemaleSin 3 years ago

Secretary - Aphrodite Adams

Secretary - Aphrodite Adams

XNXXGold 3 years ago

The Landscaper Gets A Show

55% 0:11 / 9:24

The Landscaper Gets A Show

Clips4sale 3 years ago

Full Version - Big Ass Shemale Employee Bottoms Their Way Into a Job - Wickedwhims

Full Version - Big Ass Shemale Employee Bottoms Their Way Into a Job - Wickedwhims

XHamster 3 years ago

corporate training 3d futanari animation

corporate training 3d futanari animation

PornOne 4 years ago

Sarah shows what satin wrap skirts are good for

Sarah shows what satin wrap skirts are good for

XHamster 3 years ago

My Young Secretary Opened her Tits

My Young Secretary Opened her Tits

XHamster 2 years ago

Kellystar518 in Who's That Girl?

Kellystar518 in Who's That Girl?

XHamster 2 years ago

PASSIVE TRANSVESTITE OF BRAZIL

Premium HD 25:28

PASSIVE TRANSVESTITE OF BRAZIL

XNXXGold 4 years ago

Can I go to an application meeting like this? fullversion

Can I go to an application meeting like this? fullversion

XHamster 3 years ago

Korra Del Rio`s Bubble Butt Shemale Threesome: Female Orgasms, Shemale Sex & Woman-on-Woman Action!

Korra Del Rio`s Bubble Butt Shemale Threesome: Female Orgasms, Shemale Sex & Woman-on-Woman Action!

XXXShemalePorn 3 years ago

Shemale boss analed by guy secretary

Shemale boss analed by guy secretary

Fetishpapa 3 years ago

”T-girl office slut Melanie Brooks taking shaft in office”

”T-girl office slut Melanie Brooks taking shaft in office”

ThePornstar 1 year ago

I'm Showing My Sexy Black Lingerie and Body

I'm Showing My Sexy Black Lingerie and Body

FapHouse 1 year ago

My Young Secretary Opened Her Tits

My Young Secretary Opened Her Tits

FapHouse 2 years ago

My Young Secretary Is Very Horny

My Young Secretary Is Very Horny

FapHouse 2 years ago

Naughty Secretary Here

Naughty Secretary Here

FapHouse 2 years ago

Cummies & Milking

Cummies & Milking

FapHouse 3 years ago

Full Version - Big Ass Shemale Employee Bottoms Their Way Into a Job - Wickedwhims

HD 1:01 / 13:04

Full Version - Big Ass Shemale Employee Bottoms Their Way Into a Job - Wickedwhims

FapHouse 3 years ago

Nuttytouch Appetizing Naughty Secretary Playing with Her Succulent Huge Fat Ass Sweet Ass Thirsty for Black Cock

Nuttytouch Appetizing Naughty Secretary Playing with Her Succulent Huge Fat Ass Sweet Ass Thirsty for Black Cock

FapHouse 1 year ago

Mat-ProVid011

Some.Porn 1 year ago

Horny Ts Secretary Gets Barebacked By Her Bald

Horny Ts Secretary Gets Barebacked By Her Bald

GetTranny 1 year ago

Bisex tattooed anal loving MILF fucked in office

Bisex tattooed anal loving MILF fucked in office

Some.Porn 1 year ago

26 27 28 29 30

6,945 results found

Related categories

Corset High Heels Stockings Glamour Stockings Pantyhose Elegant Garter Belts Clothed Sex Boots High Heels Shoe Nylon Desk British Stockings Secretary Anal Lace Uniform Lingerie Teen 18+ Lingerie Asian Stockings

Narrow your search

secretary anal big ass secretary office secretary secretary boss asian secretary secretary glasses blonde secretary latina secretary secretary teen 18+ secretary stockings secretary solo milf secretary vintage secretary ebony secretary secretary pov secretary threesome secretary bbc italian secretary ai generated secretary japanese secretary

Categories Pornstars

Categories Pornstars

Parents

Pornmd.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Pornmd.com. All rights reserved.

© 2026 Pornmd.com. All rights reserved.