Transgender • US
Live Sex
Premium
Videos
Categories
Pornstars
Channels
photos
First Time Crossdressing Porn Videos
4360 Results
Free Videos
Short Videos
Premium Videos
Photos
Sissy First
Men Crossdressing
Crossdressing Party
Crossdressing Transformation
Crossdressing Story
First Time Taboo
First Time Dressed
Couple First Time
TS First Time
Crossdressing Sissy
First Time POV
First Time Dildo
Crossdressing Humiliation
Crossdressing Hentai
Crossdressing Fantasy
Crossdressing Daddies
First Time Pegging
First Time Fisting
Teen First Time
Trans First
HD
Full HD
4K
VR
Best Videos
01:24
The Sissy Market - Webshop for Sissies
Sissy Joyce
10.3K views
12:36
BF demolishes my young femboy bussy (2025 Remaster)
Prettyboi2000x
222.4K views
08:12
Sissy Dressup Party Sissy Joyce & Sasha De Sade
Sissy Joyce
304.1K views
08:12
The Sissy Maid Process
Pure Ts
57.4K views
21:54
My trans-ass gets creampied by my teacher - prettyboi2000x
Prettyboi2000x
135.1K views
25:35
Vintage BB Crossdresser - Repost
167K views
08:37
Does Megan deserve BBC?
S
Sissymeganx
6.1K views
05:26
First anal- ladyboy fucks curious hetero for the first time
Ladyboy69
40.6K views
16:07
Sissy #3: Feminize Yourself
913.4K views
10:09
I Wanted to Be Fucked to My Ass
SandyPastime578
54.8K views
20:30
Trans Slut With Big Ass Gets Fucked By Trans Beauty - prettyboi2000x
Prettyboi2000x
253.3K views
42:30
Triple X pt1
1.4M views
07:57
The photographer fucked me.And cum in my ass
WanidaCrossdresser
173.5K views
11:10
Trans mum is ready for your cock!
TashaS
13.5K views
15:15
Nervous Trans Bottom Babe Tries Topping Petite Trans Sorority Hottie
GenderX
597.9K views
55:33
sam_cdsissy sissy crossdresser masturbating and cumming
63K views
08:36
Straight Guy Arrives After Party and Finds a Beautiful Trans Girl
MarilyDaniela
2M views
04:11
Huge Sissy Schoolgirl's Cock Explodes Through Friend's Mom's Shiny Gray Pantyhose
PantyhoseJuicyCummer
25.5K views
07:01
Princess Bunnie: Crossdresser MILF masturbating
Princess Bunnie
79.6K views
01:00
Bad carpal tunnel
94.8K views
08:12
Stepsister Has a Surprise for Me
John Sanders
2M views
Relevant Short videos
first time crossdressing :P
2K views
First time going out like a sissy slut !
CrossBoy with Mommy clothes
88.1K views
Sissy plays with anal plug for the first time | Clip 1
9.3K views
First Time I Go 100% Balls Deep on This One 42cm, 16 Inch
b
boobyb0y
7.1K views
skinny teen femboy getting fucked first time | Clip 1
F
Fembaby
6.6K views
Samara Coxxx training her sissy pussy with a dildo for the first time
Samara Coxxx
7K views
01:20
POV Taking Cute Sissy's Virginity on the First Date - full vid on LayneLovee Manyvids
Layne Love
68.9K views
05:20
I turned my straight roommate intro trans wife
CutePinkUnicorn
1.1M views
01:00
Favors
396K views
04:21
Crossdresser in Adult video booth
268.1K views
07:38
Submissive Bottom Receives Rough Sex From Goth Femdom
Cailey Katts
549.6K views
16:00
TRANSFIXED - Megan Mistakes Loses Virginity To Jade Venus In Sweet First Time Trans Fuck
Transfixed
424.5K views
08:12
Trained to Be a Submissive Slut
Pure Ts
71.6K views
05:43
He Met a Cute Chinese Crossdresser in a Tiny Skirt
MTFXXXVIDS
11.9K views
01:50
Sissy Kanisa, How Such a Good Sissy Take a Pee
SissyKanisa
6.1K views
13:12
Be A Slutty Sissy
30K views
11:12
Trans gets fucked at motel by a DL guy
Valentina Royale
75.3K views
08:12
Dating a mature crossdresser
Pure Ts
612.7K views
02:37
Breed me daddy
298.4K views
06:08
My straight roommate turned out to be a Trans
CutePinkUnicorn
29.6K views
02:07
Sissy Shelby Wants You To Give Her More Cock
Sissy Shelby Kiss
6.2K views
03:22
Step Bro Foxy Alex Caught Trying on Mom's Clothes & Will Do Anything to Keep It Secret
Andre Stone
285.6K views
08:12
Cheating on Her Boyfriend
Pure Ts
287.3K views
05:32
Making out with a sexy Crossdresser
Becoming Femme
1M views
07:55
He Wants to Show off His New Sissy Persona
Pure Ts
14.2K views
08:12
My First Flip Fuck with Mtf Giselle Driller
Jason With Women - Masculine Jason
586.2K views
08:48
blonde sissy fucks herself with a dildo in a chastity belt
yourprettykate
51.7K views
00:53
Deanerys costume party
167K views
15:39
Ru ts
222K views
02:56
Girl with big girldick cums in small panties
Louise_Meow
113K views
02:32
Hot Trans Babe Fucks Virgin Roommate
Cailey Katts
287.8K views
05:20
Feminine Femboy in Sexy Lingerie with a Prominent Clit
MTFXXXVIDS
296.1K views
Previous page
Next page
1
2
3
4
5
6
...
42
...
80
80
Porn Related to First Time Crossdressing
Crossdresser Submission
Young Crossdressers
Male to Female Transformation
Crossdress POV
Cosplay Shemale
Kassy Slutty
See Through Lingerie
Sissychristine
Anonymous Sissy
Crossdressed Flight Attendant
Tricked Into Trap
Nylon Foot Tease
Sissyjess
Breeding Bitch
Gay Sissyboy Leaked
Crotchless Pantyhose
Inexperienced
Sissyslut Jenny
Horny Slut
Cross Dressing Faggot
Related Channels
#99
Brat Perversions
#384
Almost Female
#378
Join My Fans
#228
Skylar Adams xxx
#154
Shinys Bound SluTS
#224
The Tgirl Pass
#383
Lina Cavalli
#347
Trans Friend
View all
Switch to Straight Porn
Switch to Gay Porn