Training Videos - Trans (90,040)

TRANSSEXUAL Willow Hammerz - I'm a sissy mega-bitch for BIG BLACK COCK

TRANSSEXUAL Willow Hammerz - I'm a sissy mega-bitch for BIG BLACK COCK

TrannyGem 6 months ago

Every Country Has Sissy Maids

Every Country Has Sissy Maids

xHamster 6 months ago

Throat training

Throat training

xHamster 2 years ago

Wanda Snake Private Show

4K 2:00 / 10:46

Wanda Snake Private Show

Flirt4Free 6 months ago

Alexxa A Private Show

HD 2:00 / 11:23

Alexxa A Private Show

Flirt4Free 6 days ago

Cum in your Wife's sexy Panties (mov)

Cum in your Wife's sexy Panties (mov)

Clips4sale 4 years ago

Lady Becky Teaches Sissy Slut Michelle to Masturbate in a Propper Way

HD 1:01 / 48:52

Lady Becky Teaches Sissy Slut Michelle to Masturbate in a Propper Way

FapHouse 2 years ago

Big Ass Trans Raven Anal Gaped and Bred after Riding Bbc Fat Dildo

Big Ass Trans Raven Anal Gaped and Bred after Riding Bbc Fat Dildo

xHamster 2 months ago

Hole Stretching, Spanking, and Wax Play w Mia &amp; Bia

Hole Stretching, Spanking, and Wax Play w Mia &amp; Bia

Clips4sale 2 years ago

Smallish Plaything in Brown Sphincter and Milking with Maturbator! Sissification of Quinne

Smallish Plaything in Brown Sphincter and Milking with Maturbator! Sissification of Quinne

TrannyGem 4 years ago

JOI For The Feminized Sissies Clit: POV, Chastity, Crossdressing, Edging, CEI And Cum Count Down

HD 0:59 / 14:35

JOI For The Feminized Sissies Clit: POV, Chastity, Crossdressing, Edging, CEI And Cum Count Down

Clips4sale 1 year ago

Nathaly Rose & Lizz Grant Private Show

Nathaly Rose & Lizz Grant Private Show

Flirt4Free 1 week ago

Sissy Fem Princess Calls You Out

Sissy Fem Princess Calls You Out

TrannyGem 9 months ago

Jasmine Dlight - Extreme Anal Training with John Thomas Xl Depth Trainer 30inches Full Dildo

Jasmine Dlight - Extreme Anal Training with John Thomas Xl Depth Trainer 30inches Full Dildo

xHamster 2 months ago

Rebeccah Gibson Private Show

HD 2:00 / 14:47

Rebeccah Gibson Private Show

Flirt4Free 1 month ago

Sissy Hope is really horny, gets fucked by a huge dildo and rubs her little clitty with vibrator.

Sissy Hope is really horny, gets fucked by a huge dildo and rubs her little clitty with vibrator.

xHamster 4 years ago

double end dildo compilation

double end dildo compilation

AnalVids 1 year ago

Sissygasm From Fat Dick I the Ass

Sissygasm From Fat Dick I the Ass

xHamster 3 weeks ago

This chab Not fast Became a Very Nice Hotty

This chab Not fast Became a Very Nice Hotty

ShemaleSin 3 months ago

He Used to Be the Boss but Not Anymore

He Used to Be the Boss but Not Anymore

FapHouse 9 months ago

Sissyfication Feminization Hotwife Sissy instructing Lesson one - When your wifey is with her paramour

Sissyfication Feminization Hotwife Sissy instructing Lesson one - When your wifey is with her paramour

TrannyGem 7 months ago

Brunette hair trans is training deepthroat

Brunette hair trans is training deepthroat

ShemaleSin 4 months ago

Teaching my sissy cunt with my Xxl Black Fuck Stick

Teaching my sissy cunt with my Xxl Black Fuck Stick

TrannyGem 3 years ago

Lady Alice Compilation 07 Mesmerizing Beautiful (mesmerize Version) View Originals by Subscription 4K Uhd 60 Fps HDR

Lady Alice Compilation 07 Mesmerizing Beautiful (mesmerize Version) View Originals by Subscription 4K Uhd 60 Fps HDR

xHamster 2 years ago

Instruction from the trainer No6 Exposure masturbation in the parking lot in front of the store

Instruction from the trainer No6 Exposure masturbation in the parking lot in front of the store

xHamster 5 months ago

I Need It Deep

xHamster 5 months ago

HornyEmpressKay - TRANSSEXUAL Kay screws her BITCH in his splendid donk

HornyEmpressKay - TRANSSEXUAL Kay screws her BITCH in his splendid donk

TrannyGem 4 years ago

Beth Kinky - Sexy got domina trains her shemale horseman pt1 HD

Beth Kinky - Sexy got domina trains her shemale horseman pt1 HD

XVideos 5 years ago

Come and see the nurse, don't be afraid of it. A Taspe Ye Ye... VaneSsaBiTCHx PariSChienne Trvprod91

Come and see the nurse, don't be afraid of it. A Taspe Ye Ye... VaneSsaBiTCHx PariSChienne Trvprod91

xHamster 2 weeks ago

pegging mistress compilation

pegging mistress compilation

AnalVids 9 months ago

Trans Domme Breaks In Sissy Slave With Cruel Cuckold Training – Full Audio

Trans Domme Breaks In Sissy Slave With Cruel Cuckold Training – Full Audio

HihentaiPorn 9 months ago

Tiny Femboy Training His Little Hole With HUGE Dildo

Tiny Femboy Training His Little Hole With HUGE Dildo

xHamster 3 years ago

Anal Bang Machine Compilation 1

Anal Bang Machine Compilation 1

ShemaleSin 1 year ago

Phat ass crossdresser let her mistress peg her with strap on

Phat ass crossdresser let her mistress peg her with strap on

XGroovy 1 year ago

It's This Sissy Milkboy's First Time

HD 0:39 / 17:35

It's This Sissy Milkboy's First Time

FapHouse 1 year ago

Mikes Hanon Private Show

Mikes Hanon Private Show

Flirt4Free 5 years ago

BRAZZERS Exxtra - 69 at the gym athletic european Chloe Lamour

BRAZZERS Exxtra - 69 at the gym athletic european Chloe Lamour

HDPornVideosTV 3 years ago

Stretching out my sissy's boipussy with my huge big black cock

Stretching out my sissy's boipussy with my huge big black cock

xHamster 2 months ago

Training of a Submissive Bitch, Fisting and Gape in the Pussy

Training of a Submissive Bitch, Fisting and Gape in the Pussy

xHamster 2 weeks ago

Chastity Keys Frozen in Cum Cubes Lottery to Find for Unlock

Chastity Keys Frozen in Cum Cubes Lottery to Find for Unlock

xHamster 1 year ago

Stivens & Fredy & Stuard Private Show

66% HD 2:00 / 9:52

Stivens & Fredy & Stuard Private Show

Flirt4Free 2 years ago

Neko Starlightfemboy Gape Training In Nylon Stockings

Neko Starlightfemboy Gape Training In Nylon Stockings

IcePorn 2 months ago

Sissy Training From The Best (wmv)

Sissy Training From The Best (wmv)

Clips4sale 4 years ago

Trans Mistress Foxxy Trains Submissive Sherman Maus With BDSM Fisting And Huge Cock

Trans Mistress Foxxy Trains Submissive Sherman Maus With BDSM Fisting And Huge Cock

Eporner 4 months ago

Trans spunk profusely after a ravage in the urethra

Trans spunk profusely after a ravage in the urethra

TrannyGem 10 months ago

Sissy Secretary with Elle Eros

Sissy Secretary with Elle Eros

FapHouse 1 year ago

Sissy taunting her encaged clitty till she fails NNN

Sissy taunting her encaged clitty till she fails NNN

TrannyGem 7 months ago

Lady Alice 12 Part 06

Lady Alice 12 Part 06

FapHouse 2 years ago

Pegging Your Ass like a Fleshlight - Gwen Adora BBW Femdom POV Strap On - hd mp4

HD 0:29 / 10:37

Pegging Your Ass like a Fleshlight - Gwen Adora BBW Femdom POV Strap On - hd mp4

Clips4sale 3 years ago

”Dominant TS Foxxy trains Sherman Maus with assfucking play”

”Dominant TS Foxxy trains Sherman Maus with assfucking play”

StarWank 9 months ago

Petra,s 6th training

Petra,s 6th training

xHamster 1 year ago

TS makes cummie

Premium HD 5:32

TS makes cummie

XVideosRed 2 years ago

sissypov - aliza breeze sissy slut loves dick

sissypov - aliza breeze sissy slut loves dick

TransDoe 2 years ago

Trapped by a SheMale

41% HD 0:15 / 7:04

Trapped by a SheMale

Clips4sale 2 years ago

TRANSSEXUAL Willow Hammerz - 2023 Mega-Bitch of the Yr

TRANSSEXUAL Willow Hammerz - 2023 Mega-Bitch of the Yr

TrannyGem 6 months ago

Huge 9in Dildo Fucking Compilation Vol.4

Huge 9in Dildo Fucking Compilation Vol.4

xHamster 9 months ago

Sloppy Ding-Dong Deepthroat Face Banging for Sissy Bitch by Bare FemDom Mistresse with Massive Blue Jock

Sloppy Ding-Dong Deepthroat Face Banging for Sissy Bitch by Bare FemDom Mistresse with Massive Blue Jock

ShemaleSin 5 years ago

Colombian Boys Private Show

66% HD 2:00 / 8:54

Colombian Boys Private Show

Flirt4Free 9 months ago

Valentin & Harris Private Show

Valentin & Harris Private Show

Flirt4Free 4 years ago

Daily cross dresser training ruined climax joi with s1monreilly

Daily cross dresser training ruined climax joi with s1monreilly

ManPorn 3 years ago

Best fuck she's ever had

HD 0:10 / 12:00

Best fuck she's ever had

LoyalFans 2 years ago

Sissy Submission - Latex Lover's Diaper Gag ASMR - full version on patreon.com/metavulgar

Sissy Submission - Latex Lover's Diaper Gag ASMR - full version on patreon.com/metavulgar

ShemaleSin 7 months ago

Madison Feel Private Show

Madison Feel Private Show

Flirt4Free 2 years ago

Babe, TransMommy needs your backside again

Babe, TransMommy needs your backside again

TrannyGem 2 years ago

Strapon Worship and Pegging

Premium HD 18:57

Strapon Worship and Pegging

xnxxGold 3 years ago

Сквирт оргазм сочная задница с анальными игрушками шлюха фембой компиляция

Сквирт оргазм сочная задница с анальными игрушками шлюха фембой компиляция

xnxxGold 9 months ago

Sestina Shay August Compilation - Anal, Riding, Big Dildos, Masturbation, Gushing Orgasm

Sestina Shay August Compilation - Anal, Riding, Big Dildos, Masturbation, Gushing Orgasm

Pornzona 1 month ago

Ellyn Shemale Goza Showing Her Feet In floor

Ellyn Shemale Goza Showing Her Feet In floor

xHamster 3 years ago

Begging Fucked with a Big Cock Using My Hot Socks

4K 2:00 / 13:05

Begging Fucked with a Big Cock Using My Hot Socks

Flirt4Free 2 months ago

Buy your ticket and let me show you my sexual skills! To start let me get undressed to you and jerk my big cock like a semental.

Buy your ticket and let me show you my sexual skills! To start let me get undressed to you and jerk my big cock like a semental.

Flirt4Free 4 years ago

The Underpants My Stepsister Stole and Dressed, Ride

The Underpants My Stepsister Stole and Dressed, Ride

FapHouse 1 week ago

1 Way! Promo FUTANARI 3D

1 Way! Promo FUTANARI 3D

Eporner 5 years ago

BRAZILIAN TRANS SLAVE TRAINING &amp_ ANAL FISTING

Premium HD 32:52

BRAZILIAN TRANS SLAVE TRAINING &amp_ ANAL FISTING

XVideosRed 4 months ago

Maid cleans teachers palace

Maid cleans teachers palace

TrannyGem 2 years ago

Trained Shemale Slave Takes Extreme Anal Punishment

Trained Shemale Slave Takes Extreme Anal Punishment

BigTitsTokyo 2 years ago

Damsel yelling after vibrating her urethra with a toy❗bougie Getting Off

Damsel yelling after vibrating her urethra with a toy❗bougie Getting Off

TrannyGem 1 year ago

Sissy Sky in lingerie and chastity daof anal training with multiple dildos and cum once hands free and again right after

Sissy Sky in lingerie and chastity daof anal training with multiple dildos and cum once hands free and again right after

xHamster 2 years ago

Sofi Betancourt Private Show

HD 2:00 / 26:50

Sofi Betancourt Private Show

Flirt4Free 2 years ago

Ass pleasing punishment

Ass pleasing punishment

FapHouse 7 years ago

Sissy Joyce needs to get milked

Sissy Joyce needs to get milked

ShemaleSin 4 years ago

Nelly Gale Private Show

65% 4K 2:00 / 17:43

Nelly Gale Private Show

Flirt4Free 2 weeks ago

Bratty African Model Seduces Producer & Sucks His Thick Cock at Home Casting!

Bratty African Model Seduces Producer & Sucks His Thick Cock at Home Casting!

xHamster 1 year ago

How's the Cumshot From Your Angle Zack?

37% HD 0:39 / 6:30

How's the Cumshot From Your Angle Zack?

FapHouse 7 months ago

Sissy in Chastity Filled with Two Beer Enemas, One at the Door

Sissy in Chastity Filled with Two Beer Enemas, One at the Door

xHamster 4 months ago

Charming Joshua & Colin Fury Private Show

56% HD 2:00 / 28:03

Charming Joshua & Colin Fury Private Show

Flirt4Free 3 years ago

Big Ass Stepmom Destroys Trans Daughter's Boy Pussy in Slut Training

Big Ass Stepmom Destroys Trans Daughter's Boy Pussy in Slut Training

JuicyTrans 4 days ago

Anon bbc ate my booty so precious I felt guilty

Anon bbc ate my booty so precious I felt guilty

ShemaleSin 3 years ago

Gos CD enjoying her black dildo

Gos CD enjoying her black dildo

xHamster 1 year ago

Daily Ride Anal Training 2

Daily Ride Anal Training 2

xHamster 3 years ago

Training You to Be My Sissy

Training You to Be My Sissy

xHamster 8 months ago

SISSY MILKING CUMSHOTS

Premium HD 1:23

SISSY MILKING CUMSHOTS

Sheer 1 year ago

Emotional moment from "Compile VANesSaBITCHxx photos SEXxLive 2023"

Emotional moment from "Compile VANesSaBITCHxx photos SEXxLive 2023"

xHamster 6 months ago

New video of me latex slut AlexaLatexwhore from the beginning of 2022

New video of me latex slut AlexaLatexwhore from the beginning of 2022

xHamster 3 years ago

hotty spanked cute butt in public

hotty spanked cute butt in public

ShemaleSin 9 months ago

Camilo Monttoya Private Show

4K 2:00 / 15:01

Camilo Monttoya Private Show

Flirt4Free 5 days ago

Alexxa A Private Show

HD 2:00 / 10:42

Alexxa A Private Show

Flirt4Free 1 week ago

2 Sissy Latex Nurses Getting Pegged in Chastity by MILF Lisa

HD 1:01 / 36:16

2 Sissy Latex Nurses Getting Pegged in Chastity by MILF Lisa

FapHouse 2 years ago

Worthless Sissy Scrubbing Filthy Floor

Worthless Sissy Scrubbing Filthy Floor

xHamster 9 months ago

Hijab Maid

xHamster 4 months ago

I like it rough now fuck my hairy pussy and ts dominates xxx Analmal Training

I like it rough now fuck my hairy pussy and ts dominates xxx Analmal Training

Eporner 5 years ago

Memorable moment from "Dominatrix Mistress April - Slave Rosie gets vacuumed"

Memorable moment from "Dominatrix Mistress April - Slave Rosie gets vacuumed"

xHamster 7 months ago

Petite Big Ass Trans Gwen Anal Fucking Herself with Black Monster Dildo

Petite Big Ass Trans Gwen Anal Fucking Herself with Black Monster Dildo

xHamster 2 months ago

Pegged in Pink - Sissy Pegging POV

Pegged in Pink - Sissy Pegging POV

xHamster 1 year ago

Big tits blonde transsexual EMT trainer Jade Venus fucking her student

Big tits blonde transsexual EMT trainer Jade Venus fucking her student

Pornicom 2 weeks ago

Strapon Fuck on Web Sission

Strapon Fuck on Web Sission

xHamster 8 months ago

Taunted Trans Doll Purity and Anal Invasion Have Fun

Taunted Trans Doll Purity and Anal Invasion Have Fun

TrannyGem 2 years ago

Nyxi Leon Does a Hot Solo with Her New Rubberized Chastity

Nyxi Leon Does a Hot Solo with Her New Rubberized Chastity

FapHouse 1 year ago

Sucking Small Penis

Sucking Small Penis

xHamster 4 weeks ago

White Sissy Virginity Instructing (Smash Machine)

White Sissy Virginity Instructing (Smash Machine)

TrannyGem 6 months ago

Hole Training

Eporner 1 year ago

Punishing The Sissy Maid

68% HD 0:28 / 29:34

Punishing The Sissy Maid

Clips4sale 2 years ago

Sissy Slut Late Evening Supper

Sissy Slut Late Evening Supper

xHamster 1 year ago

Crossdresser try on panties

Crossdresser try on panties

xHamster 4 weeks ago

Zayra Ross Private Show

Zayra Ross Private Show

Flirt4Free 2 weeks ago

Sissy crossdresser masturbating cum eating playing cock flapping balls tucked Femboy masturbation Sissygasm Asspussy

Sissy crossdresser masturbating cum eating playing cock flapping balls tucked Femboy masturbation Sissygasm Asspussy

xHamster 3 years ago

Latex gimp pegged

Latex gimp pegged

ShemaleSin 3 months ago

Big-Boobed sissy get's smashed by her boink machine while locked in her plane v-card cell

Big-Boobed sissy get's smashed by her boink machine while locked in her plane v-card cell

TrannyGem 11 months ago

Permanent Feminization ft Goddess Colleen

Permanent Feminization ft Goddess Colleen

TransTube.tv 1 year ago

Sissy Kanisa in Sexy Purple Nightwear Ep1

Sissy Kanisa in Sexy Purple Nightwear Ep1

xHamster 3 months ago

Assfucking Instructing for my Sissy Mega-Bitch

Assfucking Instructing for my Sissy Mega-Bitch

TrannyGem 6 years ago

65 66 67 68 69

90,040 results found

Related categories

Chastity Cage Cage Chastity Leashed Slave Training Dungeon Slave Humiliation Bondage Edging Dominatrix Latex Submissive Chastity Belt Suspension Slave Bondage Orgasm Spanked Whip Rubber Bound

Narrow your search

sissy training anal training dildo training slave training femdom training sissy anal training cuckold training fisting training slut training chastity training deepthroat training sub training femboy training 18+ femdom anal training stamina training training anal training slave bbc training gay training blowjob training

Categories Pornstars

Categories Pornstars

PornMD: A Porn Search Engine.

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.

© 2026 Pornmd.com. All rights reserved.

© 2026 Pornmd.com. All rights reserved.