Training Videos - Trans (119,431)

Sissy training 7: big dildos stretching my hole in stockings & suspenders

Sissy training 7: big dildos stretching my hole in stockings & suspenders

Itsrealamateurs 6 days ago

Feminization with chastity cage - task

Feminization with chastity cage - task

Clips4sale 4 years ago

Sissy was fucked and punished by her mistress

Sissy was fucked and punished by her mistress

Pornzona 2 weeks ago

Nicolle & Christian Private Show

62% HD 2:00 / 5:00

Nicolle & Christian Private Show

Flirt4Free 1 year ago

Bella Nightwish Private Show

61% 2:00 / 21:37

Bella Nightwish Private Show

Flirt4Free 6 months ago

FUTA LOVES YOU HARDER: Strap-on POV | MahoganyQen

63% HD 0:10 / 7:28

FUTA LOVES YOU HARDER: Strap-on POV | MahoganyQen

LoyalFans 8 months ago

Erika Oak's Big Inflation

Erika Oak's Big Inflation

XHamster 3 years ago

Self-training No. 75: Milk Enema Endurance Walk

HD 0:39 / 14:41

Self-training No. 75: Milk Enema Endurance Walk

FapHouse 5 months ago

Ryley Rails Edging JOI

Ryley Rails Edging JOI

XHamster 7 months ago

Phone Sex Dommes Dirty Little Sissy SISSY TRAINING ASMR JOI

Phone Sex Dommes Dirty Little Sissy SISSY TRAINING ASMR JOI

XHamster 3 months ago

Crossdresser big anal pussy with tunnel plug

Crossdresser big anal pussy with tunnel plug

XHamster 2 years ago

Oliver Whitee Party on May 11, 2026 - Part 2

61% HD 2:00 / 1:44:39

Oliver Whitee Party on May 11, 2026 - Part 2

Flirt4Free 2 months ago

Sophia Loreen Private Show

HD 2:00 / 15:44

Sophia Loreen Private Show

Flirt4Free 3 weeks ago

Jasmine_dlight & Miss Fair Trade - Pegging & Fisting for a Hungry Shemale Slut

HD 1:01 / 18:35

Jasmine_dlight & Miss Fair Trade - Pegging & Fisting for a Hungry Shemale Slut

FapHouse 1 week ago

DING-DONG PEGGING FEMDOM SISSY MILKING THE MOST GOOD SHOW!!!!

DING-DONG PEGGING FEMDOM SISSY MILKING THE MOST GOOD SHOW!!!!

ShemaleSin 1 week ago

Submissive Asian Ladyboy Anal Casting & Slave Training

Submissive Asian Ladyboy Anal Casting & Slave Training

XHamster 9 months ago

Woman Fucks Her Husband By The Anus #047 Training Sissy Lesbian Dildo

Woman Fucks Her Husband By The Anus #047 Training Sissy Lesbian Dildo

XHamster 1 year ago

Stop! Feminine Sissy's Don't Jerk Off Their Cocks – Sissy Training & Feminisation with Lady Julina

Stop! Feminine Sissy's Don't Jerk Off Their Cocks – Sissy Training & Feminisation with Lady Julina

Pornzona 2 months ago

Strip Dance from Your Little Sissy Femboy Gets Creampied Between Small Tits

Strip Dance from Your Little Sissy Femboy Gets Creampied Between Small Tits

JuicyTrans 1 month ago

4K - Girl Cock Worshipping + Secretary Dress Tearing {TEARING FEST}

66% 4K 0:11 / 23:50

4K - Girl Cock Worshipping + Secretary Dress Tearing {TEARING FEST}

Clips4sale 1 year ago

Lisa the redhead gets destroyed in anal training with TGirl Lucy

Lisa the redhead gets destroyed in anal training with TGirl Lucy

JuicyTrans 1 month ago

NA055 Two mistress , training slave and riding on his face -双女王-调教奴隶,拘束,剃毛,颜面骑乘,虐屌,惨叫

NA055 Two mistress , training slave and riding on his face -双女王-调教奴隶,拘束,剃毛,颜面骑乘,虐屌,惨叫

AShemaleTube 6 years ago

Diaper Sissy Lesson: Chastity Peeing and Fisting

Diaper Sissy Lesson: Chastity Peeing and Fisting

Pornfact 3 months ago

Janny Costa X Roberta Cortez Foot Fetish

55% 0:30 / 14:44

Janny Costa X Roberta Cortez Foot Fetish

Clips4sale 1 year ago

Amannda Skye Party on Jul 3, 2026 - Part 3

4K 2:00 / 1:52:27

Amannda Skye Party on Jul 3, 2026 - Part 3

Camster 2 weeks ago

Inked ftm trans cockridden by a slut

Inked ftm trans cockridden by a slut

Some.Porn 1 year ago

Maya Pegs You POV

55% VR 0:39 / 2:00

Maya Pegs You POV

FapHouse 9 months ago

KitsyMe0w. Greedy lil pup with uber-cute flapping tail cork

KitsyMe0w. Greedy lil pup with uber-cute flapping tail cork

TrannyGem 8 months ago

Training That Fluid Control! (f032)

Training That Fluid Control! (f032)

FapHouse 1 month ago

AB106 Conpletely domesticated kinky sissy slave- face sitting cumshot edging

AB106 Conpletely domesticated kinky sissy slave- face sitting cumshot edging

XHamster 2 years ago

Lianna Lawson - Piggy Princess Training

Lianna Lawson - Piggy Princess Training

AbTranny 4 years ago

Crossdresser takes a long walk

Crossdresser takes a long walk

Pornzona 2 months ago

Sandy Lee Members-Only Show

HD 2:00 / 12:33

Sandy Lee Members-Only Show

Camster 11 years ago

Tranny urgently needs to pee during workout! Perverted Wetting - soaking wet continued training!

Tranny urgently needs to pee during workout! Perverted Wetting - soaking wet continued training!

XHamster 3 years ago

Mattew & Molly Private Show

HD 2:00 / 13:38

Mattew & Molly Private Show

Camster 3 years ago

Futa's Pantyhose Sissy Compilation

HD 0:24 / 47:55

Futa's Pantyhose Sissy Compilation

Clips4sale 2 years ago

Sissy femboy trap squirt self facial anal toy self bang climax training compilation

Sissy femboy trap squirt self facial anal toy self bang climax training compilation

ShemaleSin 1 year ago

Petra,s Valentine date ❤️

Petra,s Valentine date ❤️

XHamster 1 year ago

Mommy’s Oral Fleshlight crushed by massive trans cock while locked in chastity

Mommy’s Oral Fleshlight crushed by massive trans cock while locked in chastity

JuicyTrans 1 month ago

No234 Suspended From a Ladder: Tuck-tuck Pussy Training

HD 0:39 / 11:35

No234 Suspended From a Ladder: Tuck-tuck Pussy Training

FapHouse 3 weeks ago

TRANSGIRL JIZM COMPILATION STAMINA COMPETE PART two - Can you make it to the end ?

TRANSGIRL JIZM COMPILATION STAMINA COMPETE PART two - Can you make it to the end ?

TrannyGem 2 years ago

MAKEUP TRANSFORMATION DEPENDENCY: Makeup Dependency Mesmerize [Power of Makeup] [Makeup] [Makeup Tutorial] [Makeup Transformation] [Transformation Fantasy]

MAKEUP TRANSFORMATION DEPENDENCY: Makeup Dependency Mesmerize [Power of Makeup] [Makeup] [Makeup Tutorial] [Makeup Transformation] [Transformation Fantasy]

Clips4sale 1 year ago

hot trans in chastity takes huge BBC fucking machine & cums

67% 4K 0:14 / 14:23

hot trans in chastity takes huge BBC fucking machine & cums

Clips4sale 1 year ago

Futanari Anal Training - The Stairs of the Goddess.[Anal dildo JOI}

Futanari Anal Training - The Stairs of the Goddess.[Anal dildo JOI}

Eporner 1 year ago

Sophia Loreen Party on Jul 11, 2026 - Part 3

HD 2:00 / 1:08:36

Sophia Loreen Party on Jul 11, 2026 - Part 3

Flirt4Free 1 week ago

Sissy in Chastity: Caught by Mom... While Dildoing in Car!!

50% HD 1:01 / 36:40

Sissy in Chastity: Caught by Mom... While Dildoing in Car!!

FapHouse 4 months ago

blowing pricks compliation and getting a facial cumshot

blowing pricks compliation and getting a facial cumshot

TransTube.tv 1 year ago

Nyl Amazonium Shar Training Wonder Woman and Power Girl Poundtown Intense Orgy

Nyl Amazonium Shar Training Wonder Woman and Power Girl Poundtown Intense Orgy

XHamster 1 year ago

Letting A Futa MILF Stuff Your Hole On Thanksgiving?!

Letting A Futa MILF Stuff Your Hole On Thanksgiving?!

Juicexxx 7 months ago

World Cup Fifa 2026 Brazil Greddy Cluster

World Cup Fifa 2026 Brazil Greddy Cluster

XHamster 4 weeks ago

Crossdresser in spandex catsuit practices sucking cock with a dildo

Crossdresser in spandex catsuit practices sucking cock with a dildo

XHamster 3 years ago

JOI For A Trans Man Part 3 Anal Only

JOI For A Trans Man Part 3 Anal Only

Clips4sale 2 years ago

Centaur Things 3 - (Amy&#039_s Big Wish 3-3) - A Futanari Deertaur Gets Trained In The Art of Breeding!

Premium HD 9:40

Centaur Things 3 - (Amy&#039_s Big Wish 3-3) - A Futanari Deertaur Gets Trained In The Art of Breeding!

XNXXGold 3 months ago

Pathetic Faggot Meltdown: The Laughter Was Real the Whole Time

Pathetic Faggot Meltdown: The Laughter Was Real the Whole Time

Clips4sale 2 months ago

BDSM Punishment Sissy Blaire_18 Spanking Bare Ass. Sissy in chastity belt

BDSM Punishment Sissy Blaire_18 Spanking Bare Ass. Sissy in chastity belt

XHamster 1 year ago

YOUR JOURNEY TO BEING MY COCKSUCKER

63% HD 0:10 / 15:42

YOUR JOURNEY TO BEING MY COCKSUCKER

LoyalFans 3 years ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 10 years ago

Releasing Enemas and Pissing Her Mouth before Pegging Her Ass Clip 2

Releasing Enemas and Pissing Her Mouth before Pegging Her Ass Clip 2

XHamster 7 months ago

JOI Hentai MILF Femboy Cumming on His Cock

JOI Hentai MILF Femboy Cumming on His Cock

XHamster 10 months ago

Play with Us

53% 4K 2:00 / 1:55:10

Flirt4Free 6 months ago

The Cuckold Sissy Holiday Package

The Cuckold Sissy Holiday Package

Pornzona 2 weeks ago

Sissy Femboy Trap Squirt Self Facial Anal Toy Self Fuck Orgasm Training Compilation

Sissy Femboy Trap Squirt Self Facial Anal Toy Self Fuck Orgasm Training Compilation

AbTranny 3 weeks ago

Blonde Trans Samus Cosplay Anal Creampie Blacked and Ass Destroyed by Two Big Black Cocks

Blonde Trans Samus Cosplay Anal Creampie Blacked and Ass Destroyed by Two Big Black Cocks

XHamster 4 months ago

Intens caught in public

Intens caught in public

Pornzona 2 months ago

Trans Goth Sissy Gasps Transformation Gas Into Chastity Dripping Ruin

Trans Goth Sissy Gasps Transformation Gas Into Chastity Dripping Ruin

JuicyTrans 3 months ago

Sissy Loser Humiliation - Femdom - Goddess Alexa

Sissy Loser Humiliation - Femdom - Goddess Alexa

Pornzona 4 months ago

Yoga Freaks: Episode 14

Yoga Freaks: Episode 14

Some.Porn 7 months ago

Sissy Babytgirl94 Extreme Deepthroat Training

Sissy Babytgirl94 Extreme Deepthroat Training

XHamster 1 year ago

Sissy slut training continues

Sissy slut training continues

Pornfact 4 days ago

Trinity CUMSLUT sperm connoisseur

Trinity CUMSLUT sperm connoisseur

XHamster 4 months ago

pain slut puppy solo training session

pain slut puppy solo training session

Pornzona 2 weeks ago

Lola Crystals (TrulyByL) gets pummeled all over room by BIG BLACK COCK

Lola Crystals (TrulyByL) gets pummeled all over room by BIG BLACK COCK

TransTube.tv 1 year ago

Training the Slut Inside You: Mesmerizing HFO [Erotic ASMR] [Training Series Part 2]

Training the Slut Inside You: Mesmerizing HFO [Erotic ASMR] [Training Series Part 2]

Pornzona 1 month ago

Femboy Anal Training

Femboy Anal Training

FapHouse 2 months ago

Maya Spring Private Show

4K 2:00 / 22:10

Maya Spring Private Show

Camster 2 weeks ago

Watch This Sissy Slut Get Her Ass Filled with a Thick Toy - Back View

Watch This Sissy Slut Get Her Ass Filled with a Thick Toy - Back View

XHamster 1 week ago

Troy Khalil Private Show

67% 4K 2:00 / 14:59

Troy Khalil Private Show

Flirt4Free 9 months ago

Trans Greased And Humped No condom

Trans Greased And Humped No condom

TransTube.tv 1 year ago

BBC Sissy Lola Destroyed Gaping on 10in Black Beast

BBC Sissy Lola Destroyed Gaping on 10in Black Beast

JuicyTrans 1 month ago

Foot Job Leads To Fucking

Foot Job Leads To Fucking

XHamster 3 years ago

louise88 best sissy training ever

louise88 best sissy training ever

AShemaleTube 5 years ago

DO YOU WISH YOUR GIRLFRIEND HAD A PEGGING FETISH?

DO YOU WISH YOUR GIRLFRIEND HAD A PEGGING FETISH?

XHamster 1 year ago

Exploring a dark tunnel with a black dildo

Exploring a dark tunnel with a black dildo

XXXShemalePorn 1 year ago

Luccas & Jhordy Private Show

59% HD 2:00 / 10:18

Luccas & Jhordy Private Show

Flirt4Free 10 months ago

Caged up and Lost the Key

Caged up and Lost the Key

FapHouse 4 weeks ago

Bad Dragon Pounding and Gaping - original early cam show by Mistress Mercer

Bad Dragon Pounding and Gaping - original early cam show by Mistress Mercer

Pornzona 2 months ago

Cycling in over 30 degrees! Tranny girl rubs her asshole on the bike!

73% HD 0:25 / 10:26

Cycling in over 30 degrees! Tranny girl rubs her asshole on the bike!

Clips4sale 1 year ago

Rans Ria Bentley Makes Dolly Rotten Snort Cum and Eat Her Void urine

Rans Ria Bentley Makes Dolly Rotten Snort Cum and Eat Her Void urine

ShemaleSin 3 months ago

Fur sissy slut deepthroat and anal dildo ride

Fur sissy slut deepthroat and anal dildo ride

XHamster 9 months ago

waiting patiently like a good girl

61% 0:39 / 27:26

waiting patiently like a good girl

FapHouse 3 years ago

Squeezing a penis into a micro cage

Squeezing a penis into a micro cage

Pornzona 1 week ago

Luke Hardy & Cristian Ford Private Show

66% HD 2:00 / 11:34

Luke Hardy & Cristian Ford Private Show

Flirt4Free 5 months ago

Sophia Loreen Private Show

HD 2:00 / 25:41

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

Large ebony schlong screwing sissy bitch Lola Crystals

Large ebony schlong screwing sissy bitch Lola Crystals

ShemaleSin 3 years ago

Romantic BDSM Lesbians Date Night Pussy Worship ft River Enza - 720p MP4

61% 4K 0:32 / 12:12

Romantic BDSM Lesbians Date Night Pussy Worship ft River Enza - 720p MP4

Clips4sale 2 years ago

Gaymer Workout

HD 0:29 / 21:31

Clips4sale 4 years ago

I came soooo damn hard!

I came soooo damn hard!

FapHouse 1 month ago

4K - Cum explosion of meow girl

67% 4K 0:08 / 29:01

4K - Cum explosion of meow girl

Clips4sale 3 years ago

BIMBOFICATION 101 1080p

BIMBOFICATION 101 1080p

Clips4sale 2 years ago

Female domination on sissy whore in chastity cage

Female domination on sissy whore in chastity cage

XHamster 3 years ago

The beginning of the long weekend.

The beginning of the long weekend.

XHamster 8 months ago

Fag slave humiliation compilation part 8

Fag slave humiliation compilation part 8

XHamster 6 months ago

Spanish Shemale Training Her Ass

Spanish Shemale Training Her Ass

XHamster 4 months ago

Ass to Mouth - Trans MILF Fucked Deep and Made to Taste Her Ass

HD 1:01 / 23:14

Ass to Mouth - Trans MILF Fucked Deep and Made to Taste Her Ass

FapHouse 2 days ago

WEENIE SUCKING CROSSDRESSER

WEENIE SUCKING CROSSDRESSER

ShemaleSin 2 weeks ago

Pegging my sissy bitch in doggy smashing her ass

Pegging my sissy bitch in doggy smashing her ass

XHamster 10 months ago

Sissy Unfathomable Mouth Training by Vibrator Machine

Sissy Unfathomable Mouth Training by Vibrator Machine

ShemaleSin 4 years ago

Hammering Her

Some.Porn 2 years ago

Your Holes Are For My Cock - Kendra James + Ts Slayer, pegging, femdom, bdsm

Your Holes Are For My Cock - Kendra James + Ts Slayer, pegging, femdom, bdsm

Clips4sale 2 years ago

Her Prisoner Part 24 - Sissy Training VII

59% 4K 0:51 / 10:40

Her Prisoner Part 24 - Sissy Training VII

Clips4sale 2 years ago

Carter Rains Private Show

Carter Rains Private Show

Camster 1 week ago

F.U.T.A. inc. Training

F.U.T.A. inc. Training

Eporner 10 months ago

Edging My Sissy Slut With A Fleshlight (He Begs To Cum)

Edging My Sissy Slut With A Fleshlight (He Begs To Cum)

Pornfact 3 days ago

Kinky Bitch - Recaptured Part Nine

63% 4K 0:43 / 12:16

Kinky Bitch - Recaptured Part Nine

Clips4sale 2 months ago

Mama Studio introduces "Training my step nephew to lick a trans for the first-ever time" - Free-for-all

Mama Studio introduces "Training my step nephew to lick a trans for the first-ever time" - Free-for-all

TrannyGem 3 months ago

sentindo no pelo o cuzinho delicioso da solzinha

sentindo no pelo o cuzinho delicioso da solzinha

PornBox 6 months ago

Dildo Dolly 4

58% 0:11 / 11:52

Clips4sale 3 years ago

Purity Sissy Assfucking Teaching Jessica Bloom Anal Invasion Directives

Purity Sissy Assfucking Teaching Jessica Bloom Anal Invasion Directives

TrannyGem 1 year ago

Caged Sissy Clitty Ass Wrecked Sissygasm Cum Gush Ruin

Caged Sissy Clitty Ass Wrecked Sissygasm Cum Gush Ruin

JuicyTrans 3 months ago

BBC & Lingerie Fuckmachine - Huge Orgasm

BBC & Lingerie Fuckmachine - Huge Orgasm

XHamster 1 year ago

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