Secretary Videos - Trans (218)

My New Sissy Secretary

59% HD 0:29 / 11:58

My New Sissy Secretary

Clips4sale 1 year ago

Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

77% 0:11 / 42:29

Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

Sucking Sissy's Cock

Sucking Sissy's Cock

Clips4sale 1 year ago

Tranny Walk & Wetting in hot white jeans !! Pissed in in public!

68% HD 0:30 / 8:03

Tranny Walk & Wetting in hot white jeans !! Pissed in in public!

Clips4sale 2 years ago

TS Office Girl Serena Darkheart - Panty Bulge, Hogtied and Ball Gagged

61% 0:34 / 10:24

TS Office Girl Serena Darkheart - Panty Bulge, Hogtied and Ball Gagged

Clips4sale 10 months ago

the end of a work week

68% 0:30 / 25:46

the end of a work week

Clips4sale 6 months ago

Sissy Sluts Part 1

52% HD 0:10 / 12:49

Sissy Sluts Part 1

LoyalFans 4 years ago

Sexy Sissy Secretary Crossdresser Mind Fuck OCT 2024

61% 0:30 / 8:17

Sexy Sissy Secretary Crossdresser Mind Fuck OCT 2024

Clips4sale 9 months ago

Bimbo Gives Boss A Blowjob

Premium HD 20:12

Bimbo Gives Boss A Blowjob

Clips4sale 1 year ago

I'm so good he cums twice

77% HD 0:43 / 6:24

I'm so good he cums twice

Clips4sale 4 months ago

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

67% HD 0:30 / 58:54

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

Clips4sale 1 year ago

ABH052 Naughty secretary in chastity and a giant squirt

HD 0:30 / 33:34

ABH052 Naughty secretary in chastity and a giant squirt

Clips4sale 4 years ago

Femdom Anal Annihilation: Big Boob Mistress Drains Prostate and Balls with Extreme Anal Fisting Part 5 of 5 (1080p)

66% HD 0:30 / 9:03

Femdom Anal Annihilation: Big Boob Mistress Drains Prostate and Balls with Extreme Anal Fisting Part 5 of 5 (1080p)

Clips4sale 1 year ago

Sissy Club Slut: Deep Throating, Pegging, and More PART 1 OF 2 (1080p)

51% HD 0:30 / 21:43

Sissy Club Slut: Deep Throating, Pegging, and More PART 1 OF 2 (1080p)

Clips4sale 1 year ago

Secretary Gets Extreme Futanari Punishment

55% HD 0:10 / 50:21

Secretary Gets Extreme Futanari Punishment

LoyalFans 1 year ago

Fireworks Fly With Brittney Kade

HD 0:11 / 21:21

Fireworks Fly With Brittney Kade

Clips4sale 3 years ago

Secretary Tied #1 Bed Struggle

65% 0:30 / 1:07

Secretary Tied #1 Bed Struggle

Clips4sale 8 months ago

From secretary to submissive - Intense bondage, CBT & edging + cumshot bonus clip

From secretary to submissive - Intense bondage, CBT & edging + cumshot bonus clip

Clips4sale 1 week ago

Cum On My New Cardigan

Cum On My New Cardigan

Clips4sale 7 months ago

Tania the sexy secretary

Premium HD 19:17

Tania the sexy secretary

Clips4sale 1 year ago

Playful secretary

65% 4K 0:11 / 6:36

Playful secretary

Clips4sale 1 year ago

Let's Fuck My Girlfriend 2: The T4T4W Rough Sex Sequel Anal Threesome Group Sex Doubleteam Eiffel Tower Tag Team

Premium HD 39:20

Let's Fuck My Girlfriend 2: The T4T4W Rough Sex Sequel Anal Threesome Group Sex Doubleteam Eiffel Tower Tag Team

Clips4sale 5 months ago

Kinky Niamh bound, gagged, and edged to orgasm by Jennifer Lunden

58% 0:30 / 17:49

Kinky Niamh bound, gagged, and edged to orgasm by Jennifer Lunden

Clips4sale 7 months ago

Secretary Niamh chairtied and double gagged, with a really tight tape wrap gag over a panties-stuffed ballgag

Secretary Niamh chairtied and double gagged, with a really tight tape wrap gag over a panties-stuffed ballgag

Clips4sale 1 month ago

trans secretary throatfucked by her boss and gets big facial

65% 0:09 / 10:50

trans secretary throatfucked by her boss and gets big facial

Clips4sale 8 months ago

(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)

67% 4K 0:30 / 58:54

(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)

Clips4sale 11 months ago

Sissy Femboy Secretary Interview

67% 0:30 / 15:40

Sissy Femboy Secretary Interview

Clips4sale 8 months ago

(4K) Femdom Anal Annihilation: Full-Length 60-MIN Huge Strap-on Cock, CBT, Extreme Fisting (4K)

66% 4K 0:30 / 1:04:09

(4K) Femdom Anal Annihilation: Full-Length 60-MIN Huge Strap-on Cock, CBT, Extreme Fisting (4K)

Clips4sale 1 year ago

(4K) Sissy Club Slut Part 1 of 2 : Mistress Stellina Trains Sissy for Deep Throating & Fat Cock Pegging (4K)

60% 4K 0:30 / 21:43

(4K) Sissy Club Slut Part 1 of 2 : Mistress Stellina Trains Sissy for Deep Throating & Fat Cock Pegging (4K)

Clips4sale 1 year ago

Skirts For A Sissy Secretary

Skirts For A Sissy Secretary

Clips4sale 6 days ago

Futanari - EXCLUSIVE CLIMAX

49% 4K 0:29 / 19:42

Futanari - EXCLUSIVE CLIMAX

Clips4sale 3 years ago

Latex Rubberdoll working as a Secretary

Latex Rubberdoll working as a Secretary

Clips4sale 3 months ago

My secretary needs to be fucked

67% HD 0:30 / 3:56

My secretary needs to be fucked

Clips4sale 3 months ago

Hot secretary

59% 4K 0:12 / 6:38

Clips4sale 1 year ago

ABH050 Beauty secretary in chastity riding dildo with sexy heels and cum in chastity

71% HD 0:29 / 44:57

ABH050 Beauty secretary in chastity riding dildo with sexy heels and cum in chastity

Clips4sale 4 years ago

ENF : WORKPLACE MISHAP *HD 1080*

58% HD 0:36 / 17:20

ENF : WORKPLACE MISHAP *HD 1080*

Clips4sale 1 year ago

HOME INVASION AWRY: LEATHERGLOVE SMOTHERING

61% 0:11 / 15:44

HOME INVASION AWRY: LEATHERGLOVE SMOTHERING

Clips4sale 1 year ago

Please Be Mean To Me 2

Please Be Mean To Me 2

Clips4sale 1 year ago

Sexy legs business woman

Sexy legs business woman

Clips4sale 4 years ago

Secretary tania

66% 4K 0:10 / 3:15

Secretary tania

Clips4sale 1 year ago

Ball Busting Secretaries Part 2!

58% HD 0:10 / 7:38

Ball Busting Secretaries Part 2!

LoyalFans 3 years ago

No Soliciting Part 2

69% 0:22 / 20:34

No Soliciting Part 2

Clips4sale 6 months ago

Kendra James: Sage Pillar: Stuck at Work Futa - 720

HD 0:30 / 11:33

Kendra James: Sage Pillar: Stuck at Work Futa - 720

Clips4sale 10 months ago

Femdom Anal Annihilation: 60-Minutes of Giant Strap-on Pegging & Deep Fisting Full-Length (1080p)

45% HD 0:30 / 1:04:09

Femdom Anal Annihilation: 60-Minutes of Giant Strap-on Pegging & Deep Fisting Full-Length (1080p)

Clips4sale 1 year ago

Sissy Club Slut: Femdom Fisting, Pegging, Dick Sticking Part 2 of 2 (1080p)

61% HD 0:22 / 29:58

Sissy Club Slut: Femdom Fisting, Pegging, Dick Sticking Part 2 of 2 (1080p)

Clips4sale 1 year ago

Yakiras Secretary Slut (Trans) on TheFlourishFetish

HD 0:10 / 11:56

Yakiras Secretary Slut (Trans) on TheFlourishFetish

LoyalFans 1 month ago

4K - Lewd Home Office EP1

4K 0:10 / 20:44

4K - Lewd Home Office EP1

Clips4sale 3 years ago

OFFICE SISSY AND COLLEAGUE IN BONDAGE

OFFICE SISSY AND COLLEAGUE IN BONDAGE

Clips4sale 1 year ago

Your Secretary's A Homewrecker

HD 0:30 / 21:45

Your Secretary's A Homewrecker

Clips4sale 3 years ago

Femdom Anal Annihilation: Big Boob Mistress with Giant Futa Cock Pegging Tiny Submissive Male Part 4 of 5 (1080p)

HD 0:29 / 13:15

Femdom Anal Annihilation: Big Boob Mistress with Giant Futa Cock Pegging Tiny Submissive Male Part 4 of 5 (1080p)

Clips4sale 1 year ago

It's So Big

68% HD 0:30 / 19:43

Clips4sale 6 months ago

Your Trans Boss's Pink Slip

70% 0:11 / 12:36

Your Trans Boss's Pink Slip

Clips4sale 1 year ago

TS Secretary Anna Sky Bound in Her Blue Satin Blouse

TS Secretary Anna Sky Bound in Her Blue Satin Blouse

Clips4sale 2 years ago

Pleasing the Boss

4K 0:17 / 15:58

Pleasing the Boss

Clips4sale 2 years ago

Sniff my worn pantyhose nylon feet

HD 0:27 / 14:35

Sniff my worn pantyhose nylon feet

Clips4sale 1 year ago

Boss Bitch Secretary Trained To Be A Gape Slut In Anal BDSM

HD 0:29 / 30:57

Boss Bitch Secretary Trained To Be A Gape Slut In Anal BDSM

Clips4sale 3 months ago

Secretary Slut Miss Helena - instead of dictation she gets her own sperm in her face!

60% HD 0:29 / 4:48

Secretary Slut Miss Helena - instead of dictation she gets her own sperm in her face!

Clips4sale 1 year ago

Nylon Teased Chastity Slut (MP4)

57% 0:30 / 17:27

Nylon Teased Chastity Slut (MP4)

Clips4sale 1 year ago

Boss's Perverted Fantasy: Sexy Secretary Trans Findom Ass Worship

55% 0:30 / 7:05

Boss's Perverted Fantasy: Sexy Secretary Trans Findom Ass Worship

Clips4sale 3 months ago

Hot Tgirl Secretary Gets Rough Ass Fuck and Swallows Big Load at Job Interview

4K 0:27 / 18:17

Hot Tgirl Secretary Gets Rough Ass Fuck and Swallows Big Load at Job Interview

Clips4sale 8 months ago

4K - Girl Cock Worshipping + Secretary Dress Tearing {TEARING FEST}

69% 4K 0:11 / 23:50

4K - Girl Cock Worshipping + Secretary Dress Tearing {TEARING FEST}

Clips4sale 5 months ago

secretary caught jerking off

62% HD 0:10 / 39:44

secretary caught jerking off

Clips4sale 2 years ago

Witchy Woman: Trans Blasphemy Goddess Puts Magic Spell On Subby Wiccan Slut

HD 0:10 / 29:15

Witchy Woman: Trans Blasphemy Goddess Puts Magic Spell On Subby Wiccan Slut

Clips4sale 5 months ago

(4K) Femdom Anal Annihilation: Dick-Sticking & XL Strap-On Pegging Part 3 of 5 (4K)

70% 4K 0:30 / 11:02

(4K) Femdom Anal Annihilation: Dick-Sticking & XL Strap-On Pegging Part 3 of 5 (4K)

Clips4sale 11 months ago

Mrs H Cumshot Compilation

74% HD 0:30 / 8:10

Mrs H Cumshot Compilation

Clips4sale 7 months ago

BOUND TO MISS COURT (WMV FORMAT)

BOUND TO MISS COURT (WMV FORMAT)

Clips4sale 1 year ago

BOUND TO MISS COURT (MP4 FORMAT)

BOUND TO MISS COURT (MP4 FORMAT)

Clips4sale 1 year ago

[Erotic Audio] Twilight Blush Ch II

HD 0:30 / 15:06

[Erotic Audio] Twilight Blush Ch II

Clips4sale 2 months ago

I'll Stroke It For You

I'll Stroke It For You

Clips4sale 6 months ago

I Relax On Rita's Couch

I Relax On Rita's Couch

Clips4sale 3 years ago

Friday Night To Myself

Friday Night To Myself

Clips4sale 3 years ago

So Much Cum!!!

HD 0:11 / 12:47

Clips4sale 2 years ago

Crossdresser Cumshots

Crossdresser Cumshots

Clips4sale 7 months ago

The Nightstand II

The Nightstand II

Clips4sale 1 year ago

Cameras, Lipstick, And Precum

Cameras, Lipstick, And Precum

Clips4sale 1 year ago

Panties For Mike

Panties For Mike

Clips4sale 1 year ago

Feet And Cleavage

Feet And Cleavage

Clips4sale 1 year ago

Nylons Make Me Wet

Nylons Make Me Wet

Clips4sale 9 months ago

The Sissy Suckretary Part Two Erotic Short Story

The Sissy Suckretary Part Two Erotic Short Story

Clips4sale 1 year ago

I Cum In A Glass The Sequel Remastered

I Cum In A Glass The Sequel Remastered

Clips4sale 3 years ago

Getting Wet For My Date

66% HD 0:30 / 11:41

Getting Wet For My Date

Clips4sale 6 months ago

By Request Another Date With The Jeep Girl

By Request Another Date With The Jeep Girl

Clips4sale 3 months ago

Skirts For A Sissy Secretary

HD 0:10 / 12:23

Skirts For A Sissy Secretary

LoyalFans 1 week ago

Cum In A Glass III

HD 0:11 / 16:23

Cum In A Glass III

Clips4sale 2 years ago

My Sexy Heels

Clips4sale 3 years ago

Warming Up My Hotel Room

HD 0:11 / 10:34

Warming Up My Hotel Room

Clips4sale 3 years ago

Special Order Panties

Special Order Panties

Clips4sale 2 years ago

Throwback Thursday Episode 4, the never ending orgasm

Throwback Thursday Episode 4, the never ending orgasm

Clips4sale 3 years ago

A Solo Clip For A Big Fan

A Solo Clip For A Big Fan

Clips4sale 3 years ago

Some Alone Time

Premium HD 13:38

Some Alone Time

Clips4sale 3 years ago

I Cum On My Feet

Premium HD 15:45

I Cum On My Feet

Clips4sale 3 years ago

Big Ass Shemale Employee Bottoms Their Way Into a Job

Big Ass Shemale Employee Bottoms Their Way Into a Job

Do You Like My Nylons?

Do You Like My Nylons?

Clips4sale 10 months ago

My Precum Feels So Good On My Pussy

My Precum Feels So Good On My Pussy

Clips4sale 8 months ago

Waiting For Kevin

Waiting For Kevin

Clips4sale 1 year ago

Go Outside And Play

HD 0:11 / 24:05

Go Outside And Play

Clips4sale 2 years ago

Unaware Giantess Secretary Upskirt

Unaware Giantess Secretary Upskirt

Clips4sale 4 years ago

Sandra Gibbons - Leather Locked Secretary (mp4 HD 720)

Sandra Gibbons - Leather Locked Secretary (mp4 HD 720)

Clips4sale 6 months ago

Touching Myself

Touching Myself

Clips4sale 5 months ago

I Drench Myself

HD 0:25 / 13:15

I Drench Myself

Clips4sale 8 months ago

Anal Creampie Workplace Harassment

Premium HD 37:13

Anal Creampie Workplace Harassment

Clips4sale 1 year ago

Oh Diane

Clips4sale 3 years ago

A Hot Motel Solo Shoot

HD 0:11 / 16:28

A Hot Motel Solo Shoot

Clips4sale 3 years ago

Fuck Machine Episode Five

HD 0:11 / 11:29

Fuck Machine Episode Five

Clips4sale 1 year ago

Chairfuck and huge Sperm in my Mouth

Chairfuck and huge Sperm in my Mouth

Clips4sale 1 year ago

Sailor Moon Cosplay Collection

HD 0:19 / 1:12:55

Sailor Moon Cosplay Collection

Clips4sale 2 years ago

Succubus Secretary Pt2

HD 0:30 / 20:29

Succubus Secretary Pt2

Clips4sale 9 months ago

My Red Body Stocking

My Red Body Stocking

Clips4sale 1 year ago

Your Secretary Is Craving Cock

Your Secretary Is Craving Cock

Clips4sale 7 months ago

Thinking Of Will

Thinking Of Will

Clips4sale 3 months ago

COUPLES BONDAGE THERAPY

61% 0:06 / 10:12

COUPLES BONDAGE THERAPY

Clips4sale 2 years ago

The Landscaper Gets A Show

55% 0:11 / 9:24

The Landscaper Gets A Show

Clips4sale 2 years ago

Trans secretary makes her own rules

Trans secretary makes her own rules

Clips4sale 3 years ago

I Am In Love With My New Buttplug

HD 0:11 / 21:32

I Am In Love With My New Buttplug

Clips4sale 3 years ago

Unwrap Me, I'm Yours!

Unwrap Me, I'm Yours!

Clips4sale 3 years ago

My New Fuck Machine Episode II

HD 0:11 / 16:27

My New Fuck Machine Episode II

Clips4sale 3 years ago

Femdom Anal Annihilation: Dick-Sticking & XL Strap-On Pegging Part 3 of 5 (1080p)

HD 0:30 / 11:02

Femdom Anal Annihilation: Dick-Sticking & XL Strap-On Pegging Part 3 of 5 (1080p)

Clips4sale 1 year ago

Tickling My Pussy

Tickling My Pussy

Clips4sale 1 year ago

Sailor Moon Cosplay Collection

HD 0:10 / 1:12:55

Sailor Moon Cosplay Collection

LoyalFans 2 years ago

Cam Show 3 Sexy Smoker Stroker Trans Lola Minaj Smoking WMVHD

Cam Show 3 Sexy Smoker Stroker Trans Lola Minaj Smoking WMVHD

Clips4sale 1 year ago

Related categories

Glamour Elegant High Heels Stockings High Heels Pantyhose Stockings Secretary Anal Classy Office Secretary Desk Assistant Lingerie Teen 18+ Amazon Position Corset Dress Nylon Lingerie Boots Rich Job Interview

Narrow your search

asian secretary office secretary japanese secretary secretary anal secretary stockings boss and secretary german secretary secretary blowjob mature secretary secretary gangbang lesbian secretary real secretary blonde secretary secretary big tits secretary creampie anal secretary hot secretary married secretary secretary threesome ebony secretary

Categories Pornstars

Categories Pornstars

Legal

Terms of Service Privacy Statement Notice and Action Policy (Link Removal) DMCA / Copyright Acceptable Content Policy Digital Services Act 2257

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.

© 2025 Pornmd.com. All rights reserved.