Training Videos - Trans (117,484)

Sissy bounces on monster schlong in the shower

Sissy bounces on monster schlong in the shower

ShemaleSin 1 week ago

Sissy Wife Licks Bull's Creampie Out Of My Panties

Sissy Wife Licks Bull's Creampie Out Of My Panties

xHamster 2 years ago

Latex Doll Milking Training Chapter 2

42% HD 1:01 / 13:58

Latex Doll Milking Training Chapter 2

FapHouse 5 months ago

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

xHamster 4 months ago

Crossdress get fuck in a van

Crossdress get fuck in a van

WebcamBros 1 week ago

Turning the Hetero you into a HOMOSEXUAL sissy Cumslut

Turning the Hetero you into a HOMOSEXUAL sissy Cumslut

TrannyGem 4 years ago

Facefuck Training of my submissive girlfriend

59% 0:39 / 7:10

Facefuck Training of my submissive girlfriend

FapHouse 1 month ago

Dreamscape trio

Dreamscape trio

Transvids.tv 3 weeks ago

Luziatv Anal Compilation Ii, Breaking My Ass, Swallowing Milk,

Luziatv Anal Compilation Ii, Breaking My Ass, Swallowing Milk,

xHamster 1 week ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 2 days ago

Maya Spring Private Show

Maya Spring Private Show

Camster 3 days ago

Teen chastity slave is fucked until gape her hole

Teen chastity slave is fucked until gape her hole

xHamster 1 year ago

Charlotte X Aria - Training Her Throat for a Futa Dick

Charlotte X Aria - Training Her Throat for a Futa Dick

3DPornDude 1 month ago

Mtof Femboy to Bimbo Transformation and Training to Be Bimbo Cumslut

51% HD 0:39 / 7:00

Mtof Femboy to Bimbo Transformation and Training to Be Bimbo Cumslut

FapHouse 1 year ago

Hermaphrodite chick fucks her cis bestie

Hermaphrodite chick fucks her cis bestie

XGroovy 1 year ago

What If I Had A Penis

59% HD 0:10 / 12:01

What If I Had A Penis

LoyalFans 3 weeks ago

Step Mommy Trains You How to Be A Sissy Cock Sucker (Humiliation) Jessica Bloom

Step Mommy Trains You How to Be A Sissy Cock Sucker (Humiliation) Jessica Bloom

Itsrealamateurs 2 weeks ago

Painful ruined orgasm cbt for my bondaged sub sissy whore

Painful ruined orgasm cbt for my bondaged sub sissy whore

xHamster 5 years ago

Sasha Earth fucks her big ass with sex toys and plays solo at home

Sasha Earth fucks her big ass with sex toys and plays solo at home

xHamster 4 years ago

Anal Fisting and Fucking with a Dildo to a Powerful Orgasm

HD 0:39 / 1:00:03

Anal Fisting and Fucking with a Dildo to a Powerful Orgasm

FapHouse 2 years ago

Goddess Kyaa & River Enza in Gape Training 1

Goddess Kyaa & River Enza in Gape Training 1

Some.Porn 1 year ago

World Cup Fifa 2026 Brazil Greddy Cluster

HD 0:39 / 10:49

World Cup Fifa 2026 Brazil Greddy Cluster

FapHouse 3 days ago

New 2024 - Miss Me?

New 2024 - Miss Me?

xHamster 2 months ago

Emily Rose Ts teaches his sissy maid how to pleasure himself with a French maid's help

Emily Rose Ts teaches his sissy maid how to pleasure himself with a French maid's help

GayX 1 month ago

Black Boy Got Turn on by His Coach at the Training Section

Black Boy Got Turn on by His Coach at the Training Section

xHamster 3 months ago

Nastya Blue Private Show

HD 2:00 / 43:00

Nastya Blue Private Show

Camster 2 years ago

TS Slut milking

HD 0:15 / 14:32

TS Slut milking

IWantClips 1 year ago

Sophia Loreen Private Show

HD 2:00 / 18:12

Sophia Loreen Private Show

Flirt4Free 5 days ago

A guy fucks his ass with a dildo

A guy fucks his ass with a dildo

xHamster 8 months ago

Hardcore Sissy Training & Handjob Instructions!

Hardcore Sissy Training & Handjob Instructions!

xHamster 1 month ago

White trans femboy gargle jack and smooch huge monster big black cock suck off energetically

White trans femboy gargle jack and smooch huge monster big black cock suck off energetically

4Gay 1 year ago

Sissy training for your feminization

58% HD 0:39 / 7:27

Sissy training for your feminization

FapHouse 3 years ago

Shemale with brilliant udders jizz shot on her brilliant trans figure

Shemale with brilliant udders jizz shot on her brilliant trans figure

TransTube.tv 1 year ago

Mature Mistress teaches two sissies how to be good cocksuckers

Mature Mistress teaches two sissies how to be good cocksuckers

Tranny.one 9 years ago

TRANSSEXUAL Sissy Super-Bitch Raunchy Pound inbetween Honeypot and Weenie

TRANSSEXUAL Sissy Super-Bitch Raunchy Pound inbetween Honeypot and Weenie

TrannyGem 5 years ago

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

Fat Ass Femboy Raven Asshole Gaped, Creampie and Cuming After Intense Anal Sex with BBC Dildo

xHamster 2 months ago

Becoming Her

xHamster 1 month ago

hot submissive tgirl slut hired to take down dictation drink piss eat ass swallow cum

57% HD 0:35 / 20:42

hot submissive tgirl slut hired to take down dictation drink piss eat ass swallow cum

PornBox 1 year ago

Turning My Boyfriend Into A Sissy

Turning My Boyfriend Into A Sissy

xHamster 4 weeks ago

poke machine deep rectal teaching and molten jizzing ( femboy sissy trap cd )

poke machine deep rectal teaching and molten jizzing ( femboy sissy trap cd )

TrannyGem 4 years ago

Luke Hardy & Cristian Ford Party on Jun 3, 2026 - Part 3

4K 2:00 / 41:40

Luke Hardy & Cristian Ford Party on Jun 3, 2026 - Part 3

Flirt4Free 3 weeks ago

Bi Encouragement Let's Watch Shemale Porn

47% HD 1:01 / 17:37

Bi Encouragement Let's Watch Shemale Porn

FapHouse 1 month ago

Sissy bitch boi Jes Brinch

Sissy bitch boi Jes Brinch

xHamster 3 months ago

I make a pact

xHamster 2 months ago

Rans Ria Bentley Makes Dolly Rotten Snort Cum and Eat Her Piss

Rans Ria Bentley Makes Dolly Rotten Snort Cum and Eat Her Piss

xHamster 2 months ago

Perv Nasty Bessy

Perv Nasty Bessy

xHamster 1 month ago

Spandex Girl Wanking Teaching two Preview

Spandex Girl Wanking Teaching two Preview

Gayhub 1 month ago

Natacha whore from Lyon fucked like a bitch

Natacha whore from Lyon fucked like a bitch

xHamster 2 months ago

Can Barely Stand Anymore... My Legs Are Still Shaking After That

74% 0:39 / 6:20

Can Barely Stand Anymore... My Legs Are Still Shaking After That

FapHouse 3 months ago

The Incantation – Halloween Exclusive

The Incantation – Halloween Exclusive

TrannyGem 1 year ago

Sophia Loreen Party on Apr 25, 2026 - Part 3

53% HD 2:00 / 1:59:26

Sophia Loreen Party on Apr 25, 2026 - Part 3

Flirt4Free 2 months ago

Femdom Humiliate Asian Sissy

61% HD 0:39 / 7:23

Femdom Humiliate Asian Sissy

FapHouse 3 months ago

Jhordy & Maxx Private Show

69% HD 2:00 / 5:03

Jhordy & Maxx Private Show

Flirt4Free 10 months ago

AB108 BadGirl FoxBae Training - Drink,screwing machine,Shemale hentai,Femdom

AB108 BadGirl FoxBae Training - Drink,screwing machine,Shemale hentai,Femdom

ShemaleSin 1 year ago

Maskedloki BBC breed trans sissies (Compilation)

Maskedloki BBC breed trans sissies (Compilation)

xHamster 2 years ago

John Deep in New Taxi Driver

John Deep in New Taxi Driver

Some.Porn 2 years ago

Sexy cd is fucked by machine all evening. Training my anus til its soggy and open.

Sexy cd is fucked by machine all evening. Training my anus til its soggy and open.

xHamster 2 weeks ago

Patricia Wolford - Machine self anal training

Patricia Wolford - Machine self anal training

xHamster 11 months ago

The Hot Rabbit 🐰

The Hot Rabbit 🐰

WebcamBros 8 months ago

Femdom Real Pair female domination pegging & ding-dong headmistress & sissy cuck feminization FULL episode

Femdom Real Pair female domination pegging & ding-dong headmistress & sissy cuck feminization FULL episode

FreePorn8 1 year ago

Sissy Verwandlung

Sissy Verwandlung

aShemaleTube 3 years ago

Femboy Gape Compilation #2 fart-gapes

Femboy Gape Compilation #2 fart-gapes

xHamster 4 months ago

Sophia Loreen Private Show

HD 2:00 / 18:12

Sophia Loreen Private Show

Camster 5 days ago

Tgirl And Her Hot BFF Learning The Joys Of Anal

Tgirl And Her Hot BFF Learning The Joys Of Anal

Eporner 1 year ago

Merciless Hotel Throatfuck Marathon, angle 2

55% HD 1:01 / 12:35

Merciless Hotel Throatfuck Marathon, angle 2

FapHouse 1 week ago

”TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!”

”TGIRLS HOOKUP: Nyxi Deemed Worthy Enough To Cum!”

Zatube 1 year ago

The Sissy Latex Fuckdoll Oral and Anal by Mistress

71% 1:01 / 12:26

The Sissy Latex Fuckdoll Oral and Anal by Mistress

FapHouse 1 year ago

Blindfolded sissy slut training

Blindfolded sissy slut training

xHamster 2 years ago

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 14

Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 14

xHamster 1 year ago

Making My Cock Explode

Making My Cock Explode

xHamster 7 months ago

Sissified Husband Gets Her Ass Pounded and Fed Her Own Cum

HD 0:39 / 17:52

Sissified Husband Gets Her Ass Pounded and Fed Her Own Cum

FapHouse 9 months ago

YOUR JOURNEY TO BEING MY COCKSUCKER

69% HD 0:10 / 15:42

YOUR JOURNEY TO BEING MY COCKSUCKER

LoyalFans 3 years ago

Step Bro Gets Caught Dressing Up

Step Bro Gets Caught Dressing Up

xHamster 3 years ago

Wank off While I jism on Your Face Sissy Fag - Jessica Bloom Humilation Jerk Off Instructions

Wank off While I jism on Your Face Sissy Fag - Jessica Bloom Humilation Jerk Off Instructions

TrannyGem 2 years ago

Trans Sissy Whore tutored by Mastix Murmur compilation

Trans Sissy Whore tutored by Mastix Murmur compilation

Amateur8 6 months ago

Sophia Loreen Private Show

HD 2:00 / 18:03

Sophia Loreen Private Show

Camster 4 days ago

Hawt Trans Beauty Fucked in Every Room of the House by TS Chick - Sexy Trans Lesbian Sex

Hawt Trans Beauty Fucked in Every Room of the House by TS Chick - Sexy Trans Lesbian Sex

Dafreeporn 7 months ago

Patric & Simon & Frederick Private Show

53% HD 2:00 / 11:22

Patric & Simon & Frederick Private Show

Flirt4Free 2 years ago

Femdom POV: Blowing Smoke and Humiliating My Cuck Ex Ep 1

Femdom POV: Blowing Smoke and Humiliating My Cuck Ex Ep 1

xHamster 1 month ago

Jose & Richard Private Show

58% HD 2:00 / 21:33

Jose & Richard Private Show

Flirt4Free 1 month ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 1 week ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 5 days ago

Two Sissy Twinks Fucked Me Raw Until I Loved Their Creampies

Two Sissy Twinks Fucked Me Raw Until I Loved Their Creampies

GayPornWatch 2 days ago

Master & Ithan Private Show

54% HD 2:00 / 9:40

Master & Ithan Private Show

Flirt4Free 1 year ago

Femboy Gape Compilation #2 fart-gapes

61% HD 1:01 / 6:11

Femboy Gape Compilation #2 fart-gapes

FapHouse 5 months ago

Paulo & Jose & Sander Private Show

64% HD 2:00 / 11:56

Paulo & Jose & Sander Private Show

Flirt4Free 2 weeks ago

Hawt Trans Sissy Maid Groans with LARGE Sextoy - HD VID Beauty Femboy Cosplayer Gets Impure with Ass Toy

Hawt Trans Sissy Maid Groans with LARGE Sextoy - HD VID Beauty Femboy Cosplayer Gets Impure with Ass Toy

ShemaleSin 1 year ago

Sophia Loreen Party on Jun 23, 2026 - Part 4

HD 2:00 / 35:23

Sophia Loreen Party on Jun 23, 2026 - Part 4

Camster 2 days ago

Sissy Trained w Girl Cock ft Ava Venom

65% HD 0:10 / 20:20

Sissy Trained w Girl Cock ft Ava Venom

LoyalFans 1 year ago

Trans Physical Therapist Ria Bentley Works Wonders On BBC Patient

Trans Physical Therapist Ria Bentley Works Wonders On BBC Patient

xHamster 1 year ago

Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow

Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow

xHamster 8 months ago

AB104 Fuckfest fucktoy tester surrender (Japanese and English subtitles)

AB104 Fuckfest fucktoy tester surrender (Japanese and English subtitles)

TransTube.tv 1 year ago

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

60% HD 0:10 / 14:58

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

LoyalFans 7 months ago

Slut Training Cum Eating 2

Slut Training Cum Eating 2

Itsrealamateurs 3 weeks ago

my husband turns his pathetic cock into a pretty pussy

my husband turns his pathetic cock into a pretty pussy

Tranny.one 1 year ago

Bonnie Boombelle Private Show

4K 2:00 / 14:58

Bonnie Boombelle Private Show

Flirt4Free 1 week ago

transangels - jessy dubai maya woulfe and roman todd ts filthy kinkfest with dominant besties

transangels - jessy dubai maya woulfe and roman todd ts filthy kinkfest with dominant besties

TransDoe 2 years ago

BBC TRAINING WITH CERJOY Clip 1

BBC TRAINING WITH CERJOY Clip 1

xHamster 8 months ago

Submissive Ladyboy Maria Anal Casting Slave Training By Ts Dominant

Submissive Ladyboy Maria Anal Casting Slave Training By Ts Dominant

getTranny 4 months ago

Trainning Is Nympho Trans Stepsis

Trainning Is Nympho Trans Stepsis

Eporner 1 week ago

First Day as Trans Sissy Sex Slave - Gangbang Training

First Day as Trans Sissy Sex Slave - Gangbang Training

xHamster 2 weeks ago

Marily Daniela Private Show

Marily Daniela Private Show

Flirt4Free 2 years ago

Training Nympho Hot Ts Stepsister Not To Dress Like Slut And To Take Big Cock

Training Nympho Hot Ts Stepsister Not To Dress Like Slut And To Take Big Cock

AbTranny 2 days ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 days ago

She's Going to Get Her Ass Fucked in the Kitchen

She's Going to Get Her Ass Fucked in the Kitchen

xHamster 11 months ago

Petra in virgin white

Petra in virgin white

BigTitsLust 1 week ago

Xxl Dildo Training Mr Hankey Toys, Greedy Cluster, Topped Toys, Kink3d and Kink_wear

Xxl Dildo Training Mr Hankey Toys, Greedy Cluster, Topped Toys, Kink3d and Kink_wear

xHamster 4 months ago

Crossdressing sissy nikki rails again

Crossdressing sissy nikki rails again

TrannyGem 4 years ago

River Enza's step-sister is a filthy slut who loves to drill and gag on a hard cock

River Enza's step-sister is a filthy slut who loves to drill and gag on a hard cock

TrannyMovs 2 weeks ago

Training My Mouth

Training My Mouth

ShemaleSin 6 days ago

Ryan743 loose hole getting spread open

Ryan743 loose hole getting spread open

xHamster 1 month ago

Dungeon Bondage Trans Gets Anal Training

Dungeon Bondage Trans Gets Anal Training

FapHouse 2 months ago

Paulo & Jose & Sander Private Show

57% HD 2:00 / 6:07

Paulo & Jose & Sander Private Show

Flirt4Free 2 weeks ago

(523) Sissygasm: Crossdresser with Anal Plug and Wand Vibrator - Zoulette (1080p, WMV)

HD 0:20 / 11:09

(523) Sissygasm: Crossdresser with Anal Plug and Wand Vibrator - Zoulette (1080p, WMV)

Clips4sale 1 year ago

Trans Angel Ella Nova and Tgirl Natalie Mars get into a steamy reverse

Trans Angel Ella Nova and Tgirl Natalie Mars get into a steamy reverse

AnalRZ 1 week ago

4K - Ichigo Femboy Pervert Panties Sucking + Cum Swallowing Play ~Ichigo x Strawberry Festival~

4K 0:18 / 18:09

4K - Ichigo Femboy Pervert Panties Sucking + Cum Swallowing Play ~Ichigo x Strawberry Festival~

Clips4sale 4 months ago

I Gave My Trans Girlfriend a Lot of Oral Sex After Training and She Came.

I Gave My Trans Girlfriend a Lot of Oral Sex After Training and She Came.

xHamster 2 months ago

Man Transformed Into Woman to Go Clubbing

Man Transformed Into Woman to Go Clubbing

xHamster 2 weeks ago

BIG BLACK COCK Bangs Sex-positive she-creature adult movie star onlyfans alexiakessel1

BIG BLACK COCK Bangs Sex-positive she-creature adult movie star onlyfans alexiakessel1

TransTube.tv 1 year ago

becomingfemme - harlee chanel workplace distraction with sissy training

becomingfemme - harlee chanel workplace distraction with sissy training

TransDoe 2 years ago

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