Transgender • US
Straight
Gay
Transgender
Videos
Photos
Short videos
Users
Live Sex
Premium
Videos
Pornstars
Channels
Short First Crossdressing Steps Porn Videos
11552 Results
Free Videos
Short videos
Premium Videos
Photos
Pink Wicked Crossdresser Slut Shows Her Tiny Puffy Boobs and Plays with Anal Plug
Melinda James
149 views
Trans gender dude bang his baby. | Clip 1
Badman4606
just added
Crossdresser talking to Step Daddy ans a CD trying to really get them to come over and play, make our, Suck cock, lick asshole | Clip 1
MadisonCD2025
69 views
First time going out like a sissy slut !
CrossBoy with Mommy clothes
69.4K views
Nady's very first selfacial
Nady-So
4.9K views
Let Me Be Your First Femboy
mothplayboy
5K views
Sissy in negative chastity cage
Sissy_Boy_Anna
11.1K views
Teen Femboy Masturbation Anal
Fembaby
3.4K views
Emotional moment from "Sissy plays with anal plug for the first time"
Vejenity
3.8K views
Lara Anal POV with Lots of Cum
EvolutionLFN
4.4K views
Samara Coxxx training her sissy pussy with a dildo for the first time
3.8K views
First Time I Go 100% Balls Deep on This One 42cm, 16 Inch
boobyb0y
2.5K views
Trans Taking an Anal Virginity
Mistress Jodie May
5.2K views
AshleyJayTS Dildo Deepthroat (first video appearance)
AshleyJayTS
2.5K views
Indian Transgender Sexy Dildo Fuck in Shower
The Sultry Seductress
3.6K views
Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm
Sissy Candy
2.9K views
Emotional moment from "Tgirl Riley anally used and pleasured on a first date"
Tgirl Riley
1.9K views
Iconic moment from "Tgirl Riley anally used and pleasured on a first date"
Tgirl Riley
2K views
I Want to Share This Grumpy Ass That Is on the Floor.
Apple00001
2.4K views
Get Into My Asshole
SandyPastime578
440 views
Key moment from "skinny teen femboy getting fucked first time"
Fembaby
1.3K views
Key moment from "Tgirl Riley anally used and pleasured on a first date"
Tgirl Riley
1.2K views
Bring Us Holes, Silkbone. or We'll Fuck Yours!
Mistress Jodie May
1.3K views
Epic moment from "Redhead sissy first using a sex-machine. This is a sweet gift from a fan"
Sonechka25
2.3K views
An Arab effeminate throws from behind | Clip 3
SmolBoimimi
1.4K views
First Time in a White Swimsuit...i Was Humiliated by Being Given a Lot of Instructions in a Limited Distribution
KANAe
2.6K views
Memorable moment from "BIG ASS Blonde BBW Hot Ladyboy Big Butt Booty Sissy Femboy Model Crossdresser Cosplayer"
Crossdresserkitty
866 views
Nyl Love on First Bite Destroying Tight Tasty Pussy Big Ass Tasty Intense Fucking Tight Pussy Swallowing Cum
Hatanoxxxmiwa
1.7K views
Our First Date
Cassandra Lovit
783 views
Sissy's first Creampie
Nikita Pink
2.3K views
Must-see moment from "First Time trying Split Screen with the Endoscope in my Dick - Full Video on manyvids and Fansly"
Lina Free
1.1K views
gorgeous crossdresser takes her first real dick
Pure Ts
1.2K views
Stunning moment from "Style Secrets: Unveiling the Crossdresser's Closet"
Crossdresserkitty
712 views
Amazing soft tiny clit sissygasm | Clip 2
Cindy Belfast
912 views
Extended Cut of My Fat Trans Ass Gets Fucked by a Black Cock for the First Time.
fermerino
1.9K views
Iconic moment from "I had my first sex, he came inside me :("
cd_aysemmm
1.8K views
I Can't Wait to Be Your Sexy Sissy Hot Bitch
SandyPastime578
359 views
Sexy Crossdresser sucks and talks to Daddy | Clip 1
MadisonCD2025
486 views
PorchaeTS takes 13 inch cock and cums hard with multiple no handed orgasms. | Clip 1
PorchaeTS
654 views
Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 8
Bailey Wilde
1.3K views
Memorable moment from "Femboy anal creampie"
Nolyneoz
1.2K views
Spectacular moment from "A horny bitch riding a huge dildo experienced her first sissygasm, squirted massively and sucked"
Harinni
1.8K views
Very Hard and Beautiful Anal Sex with a 20cm Dildo
nickyjem
485 views
I Wanted Get Fucked
SandyPastime578
266 views
Trans Slut With Big Ass Gets Fucked By Trans Beauty - prettyboi2000x | Clip 1
Prettyboi2000x
877 views
Trans Cosplayer gets tight ass destroyed and moans in pleasure (2025 Remaster) | Clip 2
Prettyboi2000x
571 views
Jaw-dropping moment from "FIRST SISSYGASM Chastity Slut Misty Cane Cums in her Cage with vibrating wand"
MistyCane
1K views
first video
crossysophie
1.3K views
Next page
1
2
3
4
5
6
...
41
...
80
80
Straight search results
Gay search results