First Time Videos - Trans (705)

His First Taste

67% 0:29 / 6:41

His First Taste

Clips4sale 1 year ago

Bretts Frist Trans Female fuck - 53 min

59% HD 0:48 / 53:34

Bretts Frist Trans Female fuck - 53 min

DarkCruising 3 years ago

TsAnnaCum4 first time anal JenissenJ

65% HD 0:28 / 35:37

TsAnnaCum4 first time anal JenissenJ

Clips4sale 1 year ago

Big Dick Ginger Tgirl eats his ass and begs to be covered in cum

57% 0:35 / 12:40

Big Dick Ginger Tgirl eats his ass and begs to be covered in cum

Clips4sale 4 months ago

Snowball Scene

62% 0:29 / 23:08

Clips4sale 2 years ago

18 Year Old Trans Girl's First Time On Camera

59% HD 0:10 / 41:02

18 Year Old Trans Girl's First Time On Camera

LoyalFans 3 weeks ago

Fucked by Your Femboy Bride Bisexual Encouragement

61% HD 0:24 / 16:27

Fucked by Your Femboy Bride Bisexual Encouragement

Clips4sale 2 years ago

CLARINHA - vol 01 - (mp4)

HD 0:13 / 14:21

CLARINHA - vol 01 - (mp4)

Clips4sale 1 month ago

latino straight boy used raw by latina transexueuel 2

latino straight boy used raw by latina transexueuel 2

PornBox 2 years ago

My First Time Meeting Hot Trans Giselle Driller

63% HD 0:10 / 34:22

My First Time Meeting Hot Trans Giselle Driller

LoyalFans 3 weeks ago

Shy Trans Femboy Loses Virginity

51% 0:17 / 9:17

Shy Trans Femboy Loses Virginity

Clips4sale 8 months ago

Instantly Smitten

HD 0:10 / 25:53

Instantly Smitten

LoyalFans 3 weeks ago

Neptune Bound Breathplay HOM w Plastic Bag 1280

64% HD 0:11 / 13:19

Neptune Bound Breathplay HOM w Plastic Bag 1280

Clips4sale 3 years ago

Wife Satisfies Your Craving for Cock

49% HD 0:30 / 18:47

Wife Satisfies Your Craving for Cock

Clips4sale 3 years ago

Nikki Montero and Alis Deepthroat BDSM the punisher slut and Nikki for the first time is a submissive bitch, lots of sexy pain

HD 0:11 / 14:17

Nikki Montero and Alis Deepthroat BDSM the punisher slut and Nikki for the first time is a submissive bitch, lots of sexy pain

Clips4sale 3 years ago

Foot Slave Tastes Cum for 1st Time!

66% 0:29 / 9:07

Foot Slave Tastes Cum for 1st Time!

Clips4sale 7 months ago

Addicted to her big black dick and thick cum

69% 0:26 / 12:20

Addicted to her big black dick and thick cum

Clips4sale 8 months ago

SOFHIA - vol 01 - (mp4)

HD 0:15 / 18:26

SOFHIA - vol 01 - (mp4)

C4S 8 months ago

Nice to Meet You: Mari Ayanami is Tied and Dominated by Freshie Juice (Japanese Language only)

60% 0:30 / 42:13

Nice to Meet You: Mari Ayanami is Tied and Dominated by Freshie Juice (Japanese Language only)

Clips4sale 8 months ago

futa friend lovingly takes your pegging virginity - SD - wmv

69% 0:29 / 32:16

futa friend lovingly takes your pegging virginity - SD - wmv

Clips4sale 2 years ago

trans slut spitroasted by BBC sex machine takes a big load

69% 0:17 / 10:08

trans slut spitroasted by BBC sex machine takes a big load

Clips4sale 11 months ago

TRANS WOMAN COUPLE SWAP

72% HD 0:24 / 18:42

TRANS WOMAN COUPLE SWAP

TEA AND TRANSCENDENCE

60% 0:20 / 18:10

TEA AND TRANSCENDENCE

Clips4sale 1 year ago

male cocks are tiny! first time with futa gf condom comparison

male cocks are tiny! first time with futa gf condom comparison

LoyalFans 1 year ago

My Second Time With Cute 18 Year Old Trans Girl - Facial

46% 0:10 / 15:43

My Second Time With Cute 18 Year Old Trans Girl - Facial

Clips4sale 1 year ago

Sarah Alexis' First Double Anal

54% HD 0:11 / 43:44

Sarah Alexis' First Double Anal

Clips4sale 1 year ago

First time with a new electrostimulator

63% 0:25 / 17:28

First time with a new electrostimulator

Clips4sale 4 years ago

Chloe Corrupt Fucks Sydney Screams - 1080 MP4

60% HD 0:29 / 21:40

Chloe Corrupt Fucks Sydney Screams - 1080 MP4

Clips4sale 3 years ago

Ember Snow- TS Fuck w Eva Maxim Pt. 1

61% HD 0:10 / 8:01

Ember Snow- TS Fuck w Eva Maxim Pt. 1

LoyalFans 1 year ago

transitioned beauty

57% 0:30 / 29:05

transitioned beauty

Clips4sale 7 months ago

18 Year Old Trans Girl's First Time On Camera

57% 0:13 / 41:01

18 Year Old Trans Girl's First Time On Camera

Clips4sale 1 year ago

Submissive White Tgirl gives Sloppy Blowjob & gets Destroyed by BBC till she begs for his cum (4k)

68% 4K 0:24 / 32:08

Submissive White Tgirl gives Sloppy Blowjob & gets Destroyed by BBC till she begs for his cum (4k)

Clips4sale 1 month ago

First Time Crossdressing: Lingerie Shopping to Hotel Room JOI CEI No Humiliation Gentle Femdom Jerk Off Instructions Butt Plug Prostate Play

46% 0:30 / 17:59

First Time Crossdressing: Lingerie Shopping to Hotel Room JOI CEI No Humiliation Gentle Femdom Jerk Off Instructions Butt Plug Prostate Play

Clips4sale 7 months ago

Futa Step-Mommy Catches You Spying WMV

68% 0:22 / 19:03

Futa Step-Mommy Catches You Spying WMV

Clips4sale 9 months ago

Getting filled by Alice

HD 0:10 / 15:20

Getting filled by Alice

LoyalFans 11 months ago

Infidelity with the Futa Next Door

66% HD 0:30 / 56:08

Infidelity with the Futa Next Door

Clips4sale 9 months ago

Shemale Lizzy Laynez is my stepbrother's girlfriend and fucks the big ass and busty Milf Silvana Lee

54% HD 0:10 / 33:31

Shemale Lizzy Laynez is my stepbrother's girlfriend and fucks the big ass and busty Milf Silvana Lee

LoyalFans 1 year ago

RUBBER PETS MATCH MAKERS

55% HD 0:10 / 26:24

RUBBER PETS MATCH MAKERS

LoyalFans 1 year ago

My New Sissy Anal Slut

HD 0:10 / 25:13

My New Sissy Anal Slut

LoyalFans 2 years ago

The Sissy Crossdresser Bareback 4

46% 0:11 / 34:00

The Sissy Crossdresser Bareback 4

Clips4sale 3 years ago

Turning You Bi - Sydney Screams & FtM Jaq Quicksilver Teach You How to Suck Cock & Make You Bi for Fxxk Buck's Large Load - Bisexual Encouragement, Make Me Bi, Handjobs - HD 1080 WMV

HD 0:22 / 11:39

Turning You Bi - Sydney Screams & FtM Jaq Quicksilver Teach You How to Suck Cock & Make You Bi for Fxxk Buck's Large Load - Bisexual Encouragement, Make Me Bi, Handjobs - HD 1080 WMV

Clips4sale 2 months ago

Nice To Meet You! with Mari Ayanami UNCENSORED

72% HD 0:10 / 42:13

Nice To Meet You! with Mari Ayanami UNCENSORED

LoyalFans 6 months ago

Step-Sisters Share A Bed! Trans Lesbian Threesome

53% 0:30 / 35:47

Step-Sisters Share A Bed! Trans Lesbian Threesome

Clips4sale 2 years ago

Ball Busting with Mistress Synthia Strong

64% HD 0:10 / 6:06

Ball Busting with Mistress Synthia Strong

LoyalFans 10 months ago

First Time Feminization With A New Pegging Slut

HD 0:10 / 25:18

First Time Feminization With A New Pegging Slut

LoyalFans 2 years ago

Brynn Michaels Kitchen Fuck

Brynn Michaels Kitchen Fuck

Clips4sale 1 year ago

BODY SWAP - YOUR GAY LOVER WAKES UP as TABITHAXXX

HD 0:10 / 28:13

BODY SWAP - YOUR GAY LOVER WAKES UP as TABITHAXXX

LoyalFans 1 year ago

Brynn Michaels Kitchen Fuck

HD 0:10 / 10:54

Brynn Michaels Kitchen Fuck

LoyalFans 1 year ago

Sucking Off Your Futa Step-Mommy with CEI

57% 4K 0:30 / 9:17

Sucking Off Your Futa Step-Mommy with CEI

Clips4sale 1 year ago

Pansexual Threesome with MILF Rebecca Moore + Hot TS Jasmine Lotus

70% 0:31 / 32:28

Pansexual Threesome with MILF Rebecca Moore + Hot TS Jasmine Lotus

Clips4sale 1 year ago

TRANS HEAVEN WITH HAVEN ROSE

54% 0:11 / 30:46

TRANS HEAVEN WITH HAVEN ROSE

C4S 2 years ago

Mistress Sophie Spanks and Fucks Me

66% HD 0:30 / 14:37

Mistress Sophie Spanks and Fucks Me

Clips4sale 3 years ago

Trans-Mommy Natalie Carnot's Panty Sniffing Puppy Boy mobile

57% HD 0:13 / 14:10

Trans-Mommy Natalie Carnot's Panty Sniffing Puppy Boy mobile

Clips4sale 9 months ago

Yasmine Lee: The Ass Fucking Masseuse cums in his mouth

59% 0:25 / 20:24

Yasmine Lee: The Ass Fucking Masseuse cums in his mouth

Clips4sale 8 months ago

Man Pegged and FISTED by Two Dominants - Jaq Quicksilver and Cosmicbroccoli - Cis man subjected to strapon sex pegging and fisting by dual domination femdom in BDSM threesome - 720p mp4

55% HD 0:29 / 1:01:33

Man Pegged and FISTED by Two Dominants - Jaq Quicksilver and Cosmicbroccoli - Cis man subjected to strapon sex pegging and fisting by dual domination femdom in BDSM threesome - 720p mp4

Clips4sale 1 year ago

first time anal

61% 0:30 / 16:52

first time anal

Clips4sale 11 months ago

P1 HALLOWEEN BLACK AND ORANGE LATEX CATSUIT TWINK LATEX FEMMEBOI SUB NEXT LEVEL SUBMISSION DEEPTHROAT

HD 0:21 / 10:20

P1 HALLOWEEN BLACK AND ORANGE LATEX CATSUIT TWINK LATEX FEMMEBOI SUB NEXT LEVEL SUBMISSION DEEPTHROAT

Clips4sale 9 months ago

Step-Son Sucks Off Futa Step-Mommy with CEI

51% 4K 0:30 / 9:17

Step-Son Sucks Off Futa Step-Mommy with CEI

Clips4sale 5 months ago

TS Venus Makes Darling Say Awe with Her Cock in This Medical Role Play

62% 0:11 / 52:08

TS Venus Makes Darling Say Awe with Her Cock in This Medical Role Play

Clips4sale 1 year ago

First Time Hooking Up with Roxxie Moth - 720 MP4

62% HD 0:29 / 21:42

First Time Hooking Up with Roxxie Moth - 720 MP4

Clips4sale 3 years ago

Tonight's Girlfriend

55% HD 0:10 / 33:19

Tonight's Girlfriend

LoyalFans 1 year ago

Sissy Pegging

61% 0:14 / 6:27

Clips4sale 2 months ago

Mistress Susi & Friends - Suck Our 3 Cocks - 4K

Mistress Susi & Friends - Suck Our 3 Cocks - 4K

Clips4sale 2 years ago

bottoming never felt so good

57% 0:11 / 28:31

bottoming never felt so good

Clips4sale 1 year ago

Your first time swallowing cum

62% 0:30 / 11:59

Your first time swallowing cum

Clips4sale 2 years ago

Nice To Meet You: Sounding, Edging and Facesitting with Mari Ayanami UNCENSORED

47% 0:30 / 42:12

Nice To Meet You: Sounding, Edging and Facesitting with Mari Ayanami UNCENSORED

Clips4sale 6 months ago

Training his ass for the first time

Training his ass for the first time

C4S 1 month ago

***fucking the hot ts slut LilithFux with TS Domme Petiteabbie***

61% 0:36 / 31:56

***fucking the hot ts slut LilithFux with TS Domme Petiteabbie***

Clips4sale 2 years ago

(HOT) Mel Fire's first time with a TS girl

63% HD 0:29 / 14:52

(HOT) Mel Fire's first time with a TS girl

Clips4sale 5 months ago

TRANS HEAVEN WITH HAVEN ROSE TS

50% 0:11 / 30:46

TRANS HEAVEN WITH HAVEN ROSE TS

Clips4sale 2 years ago

Need my BF's Dad To Fuck Me Right!

68% HD 0:30 / 25:24

Need my BF's Dad To Fuck Me Right!

Clips4sale 3 years ago

Fucking This Huge Ass Trans Girl A Year Later - Creampie

56% HD 0:10 / 18:57

Fucking This Huge Ass Trans Girl A Year Later - Creampie

LoyalFans 3 weeks ago

Suck Your First Trans Cock at the Gloryhole

76% 0:30 / 8:25

Suck Your First Trans Cock at the Gloryhole

Clips4sale 1 year ago

First Time Fucking A Trans Girl

4K 0:14 / 11:08

First Time Fucking A Trans Girl

Clips4sale 2 years ago

Swingers Party , Part 2 - Transexual Raw

63% HD 0:10 / 27:46

Swingers Party , Part 2 - Transexual Raw

LoyalFans 2 years ago

TRANS GIRL'S 1ST TIME WITH A WOMAN

HD 0:10 / 17:13

TRANS GIRL'S 1ST TIME WITH A WOMAN

LoyalFans 10 months ago

GF Dick Fucks U

HD 0:29 / 17:07

GF Dick Fucks U

Clips4sale 9 months ago

Our 1st Transsexual Threesome

61% HD 0:10 / 15:35

Our 1st Transsexual Threesome

LoyalFans 2 years ago

Victoria's New TV Slave - WMV - 1920

Victoria's New TV Slave - WMV - 1920

Clips4sale 1 year ago

Valkyrie Acid First Time Feet Tickling with Bratty Tickles - Tall Girl Overwhelmed By Foot Tickling With Long Nails

Valkyrie Acid First Time Feet Tickling with Bratty Tickles - Tall Girl Overwhelmed By Foot Tickling With Long Nails

LoyalFans 4 months ago

Creampie Water: TS jerks off and cums in the Ocean (Underwater 4k)

59% 4K 0:23 / 16:14

Creampie Water: TS jerks off and cums in the Ocean (Underwater 4k)

Clips4sale 2 months ago

Shemale Ananda First Time Full Domination - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - SPECIAL PRICE: 34 MINUTES FOR US$ 19,99!

69% HD 0:30 / 33:50

Shemale Ananda First Time Full Domination - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - SPECIAL PRICE: 34 MINUTES FOR US$ 19,99!

Clips4sale 11 months ago

Fucking my Fleshlight for the first time!

Fucking my Fleshlight for the first time!

Sissy Body Switch

48% 0:26 / 14:54

Sissy Body Switch

Clips4sale 2 years ago

CUMMING INSIDE KALLI GRACE

60% HD 0:23 / 21:58

CUMMING INSIDE KALLI GRACE

Clips4sale 10 months ago

4K - HUGE CUM LOAD on black lace lingerie

69% 4K 0:08 / 17:29

4K - HUGE CUM LOAD on black lace lingerie

Clips4sale 2 years ago

Karabella Creampies the Virgin Bell Boy

65% 4K 0:11 / 15:06

Karabella Creampies the Virgin Bell Boy

First time with a new electrostimulator (wmv)

51% 0:25 / 17:28

First time with a new electrostimulator (wmv)

Clips4sale 4 years ago

Futa Step-Mommys Blowjob & Cum Eating Instruction

71% 4K 0:30 / 9:17

Futa Step-Mommys Blowjob & Cum Eating Instruction

Clips4sale 1 year ago

The Sissy Crossdresser Bareback 2

70% HD 0:11 / 47:25

The Sissy Crossdresser Bareback 2

Clips4sale 3 years ago

Teaching a cuck bitch how to fuck

66% 0:33 / 24:51

Teaching a cuck bitch how to fuck

Clips4sale 4 years ago

Full Mouth Gag Device Bondage Submissive Tgirl Shock Collar Pain Slut Training

66% HD 0:30 / 13:38

Full Mouth Gag Device Bondage Submissive Tgirl Shock Collar Pain Slut Training

Clips4sale 6 months ago

ADVANCED CROSSDRESSING BETA - Crossdressing Training [Crossdresser] [Crossdress] [Transgender] [How To Crossdress] [Female Clothes] [Dressing Up] [Femme] [Fem Woman]

55% 0:30 / 44:24

ADVANCED CROSSDRESSING BETA - Crossdressing Training [Crossdresser] [Crossdress] [Transgender] [How To Crossdress] [Female Clothes] [Dressing Up] [Femme] [Fem Woman]

C4S 10 months ago

trans girl fucks a girl for the first time - Emily Adaire TS

58% 4K 0:55 / 10:05

trans girl fucks a girl for the first time - Emily Adaire TS

Clips4sale 3 years ago

New Girl Jodie Sevendee Agrees to Self Bondage

48% 0:30 / 9:24

New Girl Jodie Sevendee Agrees to Self Bondage

Clips4sale 3 months ago

Futanari - EXCLUSIVE CLIMAX

49% 4K 0:29 / 19:42

Futanari - EXCLUSIVE CLIMAX

Clips4sale 3 years ago

Sissy Spitroasted and filled with cum by BBC & Muscle Mommy

65% 0:34 / 24:39

Sissy Spitroasted and filled with cum by BBC & Muscle Mommy

Clips4sale 4 months ago

Futa Step-Mommy Catches You Spying

68% 0:22 / 19:03

Futa Step-Mommy Catches You Spying

Clips4sale 9 months ago

TS Ruby Bunny Chairtied in Her School Uniform

77% 0:39 / 15:06

TS Ruby Bunny Chairtied in Her School Uniform

Clips4sale 2 years ago

Cock Curious Roommate Bi Encouragement POV

63% HD 0:26 / 12:14

Cock Curious Roommate Bi Encouragement POV

Clips4sale 2 years ago

Sarah Alexis Gangbang

66% 0:52 / 31:38

Sarah Alexis Gangbang

Clips4sale 9 months ago

P2 HALLOWEEN BLACK & ORANGE LATEX CATSUIT TWINK LATEX FEMMEBOI SUB NEXT LEVEL SUBMISSION DEEPTHROAT

79% HD 0:21 / 10:25

P2 HALLOWEEN BLACK & ORANGE LATEX CATSUIT TWINK LATEX FEMMEBOI SUB NEXT LEVEL SUBMISSION DEEPTHROAT

Clips4sale 9 months ago

The Shemale Servant *4K*

64% 4K 0:08 / 6:16

The Shemale Servant *4K*

Clips4sale 3 years ago

The Sissy Crossdresser 10 Bareback

44% 0:30 / 44:51

The Sissy Crossdresser 10 Bareback

Clips4sale 7 months ago

4K 0:30 / 21:47

Brand New Trans Cutie Pixie Pond Fucked By A Man For the First Time Ever

Clips4sale 1 week ago

Dani M Love in Her "Sailor Moon" Outfit Tries Bondage Modeling!

53% HD 0:27 / 23:53

Dani M Love in Her "Sailor Moon" Outfit Tries Bondage Modeling!

Clips4sale 3 years ago

TS Counselor: Suck Your First Cock

TS Counselor: Suck Your First Cock

Clips4sale 4 years ago

The Date His First Time Discovering His GirlFriend Has A HUGE COCK

61% 0:11 / 28:50

The Date His First Time Discovering His GirlFriend Has A HUGE COCK

CDNY1 Cute Japanese CD Nanami Bound and Gagged in Windbreaker Part1 (MP4)

73% 0:11 / 17:35

CDNY1 Cute Japanese CD Nanami Bound and Gagged in Windbreaker Part1 (MP4)

Clips4sale 2 years ago

Pimped in the gay club

57% HD 0:15 / 13:42

Pimped in the gay club

Clips4sale 3 years ago

Too Hot to Handle in Denmark

52% HD 0:10 / 17:09

Too Hot to Handle in Denmark

LoyalFans 2 years ago

Rubber Female Mask Crossdresser Gets Fucked by Strap-on in Midair! Anal Fisting!

65% HD 0:11 / 36:30

Rubber Female Mask Crossdresser Gets Fucked by Strap-on in Midair! Anal Fisting!

Clips4sale 3 years ago

Imposed Feminization and Double Domination

50% HD 0:30 / 58:28

Imposed Feminization and Double Domination

Clips4sale 7 months ago

Ava Holt Footjob And Frot

68% HD 0:11 / 23:43

Ava Holt Footjob And Frot

C4S 2 years ago

Pumping my dick in heels and stockings

HD 0:10 / 22:07

Pumping my dick in heels and stockings

Clips4sale 2 years ago

Turning You Bi - Sydney Screams & FtM Jaq Quicksilver Teach You How to Suck Cock & Make You Bi for Fxxk Buck's Large Load - Bisexual Encouragement, Make Me Bi, Handjobs - HD 1080 MP4

63% HD 0:22 / 11:39

Turning You Bi - Sydney Screams & FtM Jaq Quicksilver Teach You How to Suck Cock & Make You Bi for Fxxk Buck's Large Load - Bisexual Encouragement, Make Me Bi, Handjobs - HD 1080 MP4

Clips4sale 2 months ago

Making You Happy - Ninania Star & Sydney Screams in Collaboration with QueerCrush - HD 1080 WMV

HD 0:27 / 31:13

Making You Happy - Ninania Star & Sydney Screams in Collaboration with QueerCrush - HD 1080 WMV

Clips4sale 1 year ago

Your TS Date Jerks Off in the Restaurant

42% 0:11 / 8:15

Your TS Date Jerks Off in the Restaurant

Clips4sale 2 years ago

Itzel Saenz First Footjob

65% HD 0:11 / 27:31

Itzel Saenz First Footjob

C4S 2 years ago

Nosy Neighbours: Fucking The Sugar that Lives Next Door

Nosy Neighbours: Fucking The Sugar that Lives Next Door

C4S 2 years ago

1 2 3 4 5

705 results found

Related categories

Gay Teen 18+ Adorable Cute Teen Orgasm 18+ Young Cum In Mouth 18+ Creampie Teen 18+ Adorable Teen 18+ Teen Cum In Mouth 18+ Uncut Dick Cum Inside Teen 18+ Teen Blowjob 18+ Hardcore Teen 18+ Pre-Cum Snowballing Dick Teen Blonde 18+ Horny Teen 18+ Young 18+ Brunette Teen 18+ Hairless

Narrow your search

first time with tranny straight first time first time anal first time bottom trans first time first time straight straight guy first time trans fucks guy first time anal first time his first time sissy first time amateur first time first time trans first time big cock femboy first time 18+ teen first time anal 18+ pegging first time first time cum in mouth first time pov real first time

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.