Role Play

52 videos in this category

52 videos sit under the Role Play category — one of the collections that make up the AllTransTube catalog. Related categories include Amateur, Transgender, Blowjob.

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Top in Role Play

Standout picks from deeper in this collection.

Part two of attempting trans for the 1st time- You deep-throat her doll fuck-stick, she rails you til you jizm1:36
Trans Female trains you to deep-throat dinky, beginning soft but then predominant you and humping your face4:30

BBC Daemon Loki Breeds Femboy Trap Nun in Chastity — Amateur

BBC Daemon Loki Breeds Femboy Trap Nun in Chastity

#Amateur #Guy Fucks Shemale

16 October 2026

What a ridiculous slave! Fucks himself with a champagne bottle and cums in his face! — Amateur

What a ridiculous slave! Fucks himself with a champagne bottle and cums in his face!

#Amateur #Shemale Fucks Guy

14 October 2026

Sissy Training — Amateur

26 September 2026

Boss Records Asian Trans Assistant Getting Creampied - TGIRLS HOUSE — Amateur

Boss Records Asian Trans Assistant Getting Creampied - TGIRLS HOUSE

#Amateur #Guy Fucks Shemale

24 September 2026

Pulling Rank: Dirty Hot Cop Melanie Brooks Fucks Evidence Room Boy — Amateur

Pulling Rank: Dirty Hot Cop Melanie Brooks Fucks Evidence Room Boy

#Amateur #Big Tits

23 September 2026

Step Bro Foxy Alex Caught Trying on Mom's Clothes & Will Do Anything to Keep It Secret — Interracial

Step Bro Foxy Alex Caught Trying on Mom's Clothes & Will Do Anything to Keep It Secret

#Interracial #Creampie

16 September 2026

Your Trans Girlfriend Jessica Bloom Thanks You for New High Heels - Big Dick Edging And Cumshot — Amateur

Your Trans Girlfriend Jessica Bloom Thanks You for New High Heels - Big Dick Edging And Cumshot

#Amateur #Shemale Fucks Guy

16 September 2026

Princess Bunnie: Naughty Maid Sneaks off to Masturbate — Amateur

Princess Bunnie: Naughty Maid Sneaks off to Masturbate

#Amateur #Shemale Fucks Guy

7 September 2026

Anal Room Service with Mistress Lilith — Amateur

Anal Room Service with Mistress Lilith

#Amateur #Shemale Fucks Guy

28 August 2026

JOI & Cum Countdown with Horny Transgirl — Amateur

JOI & Cum Countdown with Horny Transgirl

#Amateur #Big Tits

22 August 2026

blowjob amateur — Bareback

blowjob amateur

#Bareback #Mature

16 August 2026

ASMR Trans GF gives JOI and Cum Countdown — Amateur

ASMR Trans GF gives JOI and Cum Countdown

#Amateur #Shemale Fucks Guy

13 August 2026

Picking Up Big Cock Asian Trans On The Beach - TGIRLS HOUSE — Amateur

Picking Up Big Cock Asian Trans On The Beach - TGIRLS HOUSE

#Amateur #Shemale Fucks Guy

12 August 2026

Vintage fantasy trans porn star Vicki Richter — Amateur

Vintage fantasy trans porn star Vicki Richter

#Amateur #Shemale Fucks Guy

8 August 2026

Suck Jessica Bloom's Trans Cock - Large Buttplug Training + Swallow My Load Then Your Own CEI — Amateur

Suck Jessica Bloom's Trans Cock - Large Buttplug Training + Swallow My Load Then Your Own CEI

#Amateur #Shemale Fucks Guy

5 August 2026

TS Cumslut Elf Fucked Hard By Santa - Ass to Mouth And Facial Jessica Bloom — Amateur

TS Cumslut Elf Fucked Hard By Santa - Ass to Mouth And Facial Jessica Bloom

#Amateur #Shemale Fucks Guy

2 August 2026

Woman is God's masterpiece, especially when she has the devil in her — Amateur

Woman is God's masterpiece, especially when she has the devil in her

#Amateur #Shemale Fucks Guy

3 June 2026

TRANS ANGELS - Smoking Hot Nurse Miran Gives Gabriel A Naughty Treatment He Will Never Forget — Amateur

TRANS ANGELS - Smoking Hot Nurse Miran Gives Gabriel A Naughty Treatment He Will Never Forget

#Amateur #Bareback

31 May 2026

She-masculine Janice Wants to Go to the Store but There's A Bump in Her Mini-mini-skirt — Cumshot

She-masculine Janice Wants to Go to the Store but There's A Bump in Her Mini-mini-skirt

#femboy #big dick

27 May 2026

Punk Tgirl Binds Down Her Roomie and Uses Him — Amateur

Punk Tgirl Binds Down Her Roomie and Uses Him

27 May 2026

Step brutha-in-law has his way with trans step stepsister-in-law — Big Ass

Step brutha-in-law has his way with trans step stepsister-in-law

#sissy #transgender

27 March 2026

Lonely Midwestern Punk Doll Attempts Out Fresh App... DickDash! — Creampie

Lonely Midwestern Punk Doll Attempts Out Fresh App... DickDash!

22 March 2026

Taking My Chaste Sissy Stupid Damsels Pegging V-card with My Cord-on in Restrain bondage by Domina Mercer — Hardcore

Taking My Chaste Sissy Stupid Damsels Pegging V-card with My Cord-on in Restrain bondage by Domina Mercer

#sissy #feminization

22 March 2026

I got the technician visit to check my washing machine and ended up fucking beautiful TRANS GIRL — anal

I got the technician visit to check my washing machine and ended up fucking beautiful TRANS GIRL

#anal #Big Tits

20 March 2026

Sweet bimbo girl dancing — Amateur

Sweet bimbo girl dancing

#Amateur #Shemale Fucks Guy

15 March 2026

joi horny shemale with huge cock fuck fleshlight and cumshot in your face — Amateur

joi horny shemale with huge cock fuck fleshlight and cumshot in your face

#Amateur #Shemale Fucks Guy

13 March 2026

Slave White Boy Deep-mouths Fuck-stick Before Getting Wrecked By Serena Cocoa’s Beef whistle For The Very first-ever Time — Amateur

Slave White Boy Deep-mouths Fuck-stick Before Getting Wrecked By Serena Cocoa’s Beef whistle For The Very first-ever Time

25 February 2026

Trans Step Daughter JoI - Please Cum For Me Step Daddy, Your Baby Girl Needs Both Our Cum - Jessica Bloom — Amateur

Trans Step Daughter JoI - Please Cum For Me Step Daddy, Your Baby Girl Needs Both Our Cum - Jessica Bloom

#Amateur #Big Cock

20 February 2026

Your Best Friend's Asian Trans Girlfriend Didi Divina Really Wants Your Cum — Amateur

Your Best Friend's Asian Trans Girlfriend Didi Divina Really Wants Your Cum

#Amateur #Interracial

20 February 2026

horny sporty shemale with big cock dominant cum in your face and fucks her fleshlight hard — Amateur

horny sporty shemale with big cock dominant cum in your face and fucks her fleshlight hard

#Amateur #Shemale Fucks Guy

16 February 2026

PUNISHMENT — Ebony

16 February 2026

Horse Cock Kimber Strokes Huge Cumshot — Amateur

Horse Cock Kimber Strokes Huge Cumshot

#Amateur #Big Tits

14 February 2026

Boss fucks the ass of delicious trans secretary — Amateur

Boss fucks the ass of delicious trans secretary

#Amateur #Shemale Fucks Guy

14 February 2026

Mistress Holly makes you ruin your orgasm and lick up your own cum JOI CEI trailer — Amateur

Mistress Holly makes you ruin your orgasm and lick up your own cum JOI CEI trailer

#Amateur #Big Tits

13 February 2026

Adorable diminutive trans stepsis helps step step-brother-in-law with his “problem” — Amateur

Adorable diminutive trans stepsis helps step step-brother-in-law with his “problem”

13 February 2026

Ultra-cute tgirl plows herself in the family barn — Amateur

Ultra-cute tgirl plows herself in the family barn

#big ass #blonde

8 February 2026

Jessica Bloom Edges Her Hard Cock And Begs For Your Dick - Dildo Riding Anal Orgasm — Amateur

Jessica Bloom Edges Her Hard Cock And Begs For Your Dick - Dildo Riding Anal Orgasm

#Amateur #Shemale Fucks Guy

7 February 2026

Trans Damsel takes Immense Trunk like a mega-cockslut — Amateur

Trans Damsel takes Immense Trunk like a mega-cockslut

#anal #doggystyle

7 February 2026

Femboy masturbates in skirt and tights teasing you JOI countdown — Amateur

Femboy masturbates in skirt and tights teasing you JOI countdown

#Amateur #Shemale Fucks Guy

31 January 2026

TRANS ANGELS - Officer Chanel Santini Cannot Resist Getting Fucked With Hot Prisoner Kimberlee — Amateur

TRANS ANGELS - Officer Chanel Santini Cannot Resist Getting Fucked With Hot Prisoner Kimberlee

#Amateur #Bareback

26 January 2026

Trans Femdom Jessica Bloom Edges And Milks Her Huge Cock While Humiliating You SPH — Amateur

Trans Femdom Jessica Bloom Edges And Milks Her Huge Cock While Humiliating You SPH

#Amateur #Shemale Fucks Guy

26 January 2026

Fit Tgirl rails her faux-cock then her Dominatrix — Big Ass

Fit Tgirl rails her faux-cock then her Dominatrix

#tgirl #roleplay

26 January 2026

GenderXFilms - Naughty Nurse Checks Patients Prostate wt Her Massive Cock — Amateur

GenderXFilms - Naughty Nurse Checks Patients Prostate wt Her Massive Cock

#Amateur #Bareback

26 January 2026

Trans Nymph makes her BOYFRIEND blow her shaft & shoots a load in his facehole while she plays Movie Games — Amateur

Trans Nymph makes her BOYFRIEND blow her shaft & shoots a load in his facehole while she plays Movie Games

#blowjob #cum in mouth

26 January 2026

GROOBYGIRLS: Kristen's Kitchen Fuck (HOT!) — Amateur

GROOBYGIRLS: Kristen's Kitchen Fuck (HOT!)

#Amateur #Guy Fucks Shemale

26 January 2026

Trans Egirl Cucks GIRLFRIEND And Gets Her To Join In - Feat, PuppygirlXO — Blowjob

Trans Egirl Cucks GIRLFRIEND And Gets Her To Join In - Feat, PuppygirlXO

#femboy #blonde

26 January 2026

Trans Damsel entices you to try nymph penis after your breakup- Inexperienced real couple Homemade Roleplay — Amateur

Trans Damsel entices you to try nymph penis after your breakup- Inexperienced real couple Homemade Roleplay

24 January 2026

Trans gal Carrie rails BIG BLACK COCK Faux-cock — Hardcore

Trans gal Carrie rails BIG BLACK COCK Faux-cock

24 January 2026

Emo Tgirl Trusses Down Her Roommate and Uses Him — Amateur

Emo Tgirl Trusses Down Her Roommate and Uses Him

24 January 2026

Step-brother-in-law Didn't Believe I Was A Vrigin-Petite Trans Stepsis Raunchy Inner jizz shot — Creampie

Step-brother-in-law Didn't Believe I Was A Vrigin-Petite Trans Stepsis Raunchy Inner jizz shot

24 January 2026