Training Videos - Trans (124,004)

Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow Clip 1

Sissy gothic cow with red hair and in chastity rides a big black dildo on her pillow Clip 1

XHamster 10 months ago

HER FIST REALL BIG BLACK COCK PT 2

HER FIST REALL BIG BLACK COCK PT 2

TransTube.tv 2 years ago

SUBMISSIVE ASIAN LADYBOY SLAVE TRAINING &amp_ ANAL CASTING

Premium HD 38:31

SUBMISSIVE ASIAN LADYBOY SLAVE TRAINING &amp_ ANAL CASTING

XVideosRed 4 months ago

Bi Encouragement Let's Watch Shemale Porn

43% HD 1:01 / 17:37

Bi Encouragement Let's Watch Shemale Porn

FapHouse 4 months ago

Adele & Eccatelina Private Show

62% HD 2:00 / 4:57

Adele & Eccatelina Private Show

Flirt4Free 3 years ago

sissypov - ash steele be a good girl and the cutest femboi in the world

sissypov - ash steele be a good girl and the cutest femboi in the world

TransDoe 2 years ago

sissypov - bunny summers transgirl beta bedtime fantasy

sissypov - bunny summers transgirl beta bedtime fantasy

TransDoe 2 years ago

Viky Miller & Tatiana Gonzales Private Show

Viky Miller & Tatiana Gonzales Private Show

Camster 1 year ago

Railing big dinky with nip vibration

Railing big dinky with nip vibration

TrannyGem 3 years ago

becoming femme - riley jay being a hot blonde is so much fun porn video

becoming femme - riley jay being a hot blonde is so much fun porn video

TransDoe 1 year ago

男娘用巨大的假JJ满足自己空虚的菊穴疯狂喷精

男娘用巨大的假JJ满足自己空虚的菊穴疯狂喷精

ShemaleSin 1 year ago

Sophia Loreen Party on Sep 8, 2026 - Part 4

4K 2:00 / 49:05

Sophia Loreen Party on Sep 8, 2026 - Part 4

Flirt4Free 1 week ago

Sissy goth in latex self bondage with giant plug and cock gagball Clip 2

Sissy goth in latex self bondage with giant plug and cock gagball Clip 2

XHamster 10 months ago

Orgasm Addiction Fingering

63% HD 0:11 / 11:36

Orgasm Addiction Fingering

Clips4sale 4 years ago

2B's Corruption Comics JOI (Futa, Assplay, Breathplay, Facesitting, Oral-Sex, CEI, Sissy Training)

2B's Corruption Comics JOI (Futa, Assplay, Breathplay, Facesitting, Oral-Sex, CEI, Sissy Training)

ShemaleSin 5 years ago

Femdom Mommy Mistress Milks Bound Sissy Crossdresser

Femdom Mommy Mistress Milks Bound Sissy Crossdresser

Eporner 7 years ago

Shemale Mistress Trains her new Pet

Shemale Mistress Trains her new Pet

Tranny.one 4 years ago

Caught in the Act (Sissy caption Story)

Caught in the Act (Sissy caption Story)

ShemaleSin 5 years ago

That’s What Happened in the New Slave Welcome Room

38% HD 1:01 / 8:02

That’s What Happened in the New Slave Welcome Room

FapHouse 2 years ago

TRANSFIXED - EMT Jade Venus Saves Businessman Roman Todd's Sex Life During Training

TRANSFIXED - EMT Jade Venus Saves Businessman Roman Todd's Sex Life During Training

Some.Porn 1 year ago

Suck Girl Cock and beg her Sperm

46% 0:16 / 7:24

Suck Girl Cock and beg her Sperm

Clips4sale 2 years ago

Pretty Sissy Crossdresser SPUNKS from giving a FELLATIO

Pretty Sissy Crossdresser SPUNKS from giving a FELLATIO

TransTube.tv 1 year ago

Becoming the Perfect Mindless Cum Dump - MULTIPLE CUM POINTS

HD 0:25 / 33:03

Becoming the Perfect Mindless Cum Dump - MULTIPLE CUM POINTS

C4S 19 hours ago

4K - Twintail girl cum hard twice

4K 0:08 / 25:29

4K - Twintail girl cum hard twice

Clips4sale 3 years ago

Chastity Sissy Maid Service Training With Ria Bentley

Chastity Sissy Maid Service Training With Ria Bentley

Amateur8 10 months ago

TGIRL DRILLS A FURRY RAVE FEMBOY

TGIRL DRILLS A FURRY RAVE FEMBOY

TransTube.tv 1 year ago

SISSY MAKER From House Maid To Bimbo

55% HD 0:18 / 19:58

SISSY MAKER From House Maid To Bimbo

Clips4sale 2 years ago

French trans Morgane Marks spanked and fucked in the ass

73% 0:30 / 23:19

French trans Morgane Marks spanked and fucked in the ass

Clips4sale 1 year ago

GayAsianNetwork - Muscle Tristan Tran 18 yr old pounding video

GayAsianNetwork - Muscle Tristan Tran 18 yr old pounding video

GayMenSexTube 2 years ago

Trannies in training - (Episode #01)

Trannies in training - (Episode #01)

AShemaleTube 1 year ago

Sissy Slut Anal Destruction

46% HD 1:01 / 19:58

Sissy Slut Anal Destruction

FapHouse 1 year ago

Sex Training Trans Baby Cumshot Compilation Handjob

Sex Training Trans Baby Cumshot Compilation Handjob

XHamster 4 months ago

Christian & Elvis & Aron Private Show

Christian & Elvis & Aron Private Show

Flirt4Free 3 years ago

TS Carmen Lecturers Turns A TOP into HER BOTTOM

TS Carmen Lecturers Turns A TOP into HER BOTTOM

TransTube.tv 2 years ago

2 shemales for a very hard whipping

2 shemales for a very hard whipping

ManPorn 7 years ago

Mistress Fucks Slave and Makes Him Cum 5 Times! - Full Movie!

63% HD 1:01 / 1:42:16

Mistress Fucks Slave and Makes Him Cum 5 Times! - Full Movie!

FapHouse 1 year ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 10 months ago

Micky Mackenzie Private Show

56% HD 2:00 / 5:38

Micky Mackenzie Private Show

Flirt4Free 12 years ago

Another Transgender Slut Training Herself To Suck Her Own Thicc Cock, AI Generated

Premium HD 1:23

Another Transgender Slut Training Herself To Suck Her Own Thicc Cock, AI Generated

XVideosRed 10 months ago

Sissy Femme Sandy in a little fufu clip

Sissy Femme Sandy in a little fufu clip

XHamster 2 years ago

Naughty List: Mom's Sissy Slut for Santa

67% HD 0:10 / 20:00

Naughty List: Mom's Sissy Slut for Santa

LoyalFans 4 years ago

Projectile Spraying Cummies in Virginity, lil' plums SLAPPED, & Turning the Pummel Machine to its MAX

Projectile Spraying Cummies in Virginity, lil' plums SLAPPED, & Turning the Pummel Machine to its MAX

TrannyGem 2 years ago

Thomas Jasper Private Show

Thomas Jasper Private Show

Flirt4Free 4 days ago

Alexxa A Private Show

HD 2:00 / 27:45

Alexxa A Private Show

Camster 3 weeks ago

this kitty get's played with and ruined with oral cumshot

this kitty get's played with and ruined with oral cumshot

XXXShemalePorn 8 years ago

Basic Rules 4 a novice slut - No Puppy Chow Today

Basic Rules 4 a novice slut - No Puppy Chow Today

Clips4sale 1 year ago

Sissy Training After First Time Feminization

Sissy Training After First Time Feminization

XHamster 2 years ago

Sissygasm Contest Day 1 - Sissy Trap Man Rails Faux-Cock

Sissygasm Contest Day 1 - Sissy Trap Man Rails Faux-Cock

TrannyGem 4 years ago

Joanna's Softcore Dance Live Fetish Corset Leather trousers Sissy Biotch Gimp

Joanna's Softcore Dance Live Fetish Corset Leather trousers Sissy Biotch Gimp

TrannyGem 2 years ago

The Sissygasm

XHamster 1 year ago

Huge hands free cumshot sissygasm Clip 1

Huge hands free cumshot sissygasm Clip 1

XHamster 1 year ago

SISSY SLUT BIMBO MESMERIZE

59% HD 0:10 / 13:20

SISSY SLUT BIMBO MESMERIZE

LoyalFans 2 years ago

Jolly Sin Rough Anal Training with Thai Ladyboy MILF Slut Gets Creampie

Jolly Sin Rough Anal Training with Thai Ladyboy MILF Slut Gets Creampie

AveXXX 3 days ago

Sissy husband dressed up, bent over and pegged in his worthless ass

Sissy husband dressed up, bent over and pegged in his worthless ass

XHamster 3 years ago

Vladasexytrans Streched Hole and Play with Anal

Vladasexytrans Streched Hole and Play with Anal

FapHouse 1 year ago

Tgirl Teaches Sissy Arabic Tgirl To Inhale Her Weenie - POINT OF VIEW

Tgirl Teaches Sissy Arabic Tgirl To Inhale Her Weenie - POINT OF VIEW

TrannyGem 3 years ago

pounding nympho stepsister

pounding nympho stepsister

XXXShemalePorn 2 months ago

Dont just be a Butt Slut. Become a Throat Slut too! Give him 2 Holes to Fuck like its a Pussy. Deepthoat Training.

Dont just be a Butt Slut. Become a Throat Slut too! Give him 2 Holes to Fuck like its a Pussy. Deepthoat Training.

XHamster 2 years ago

Lola Frina shoots cum every time something gets inside her shemale ass

Lola Frina shoots cum every time something gets inside her shemale ass

MyLust 2 years ago

Sissy Boi’s Tiny Cock Is Caged Whilst Spreading Their Ass Cheeks and Fucking Their Worthless Ass

67% HD 1:01 / 21:45

Sissy Boi’s Tiny Cock Is Caged Whilst Spreading Their Ass Cheeks and Fucking Their Worthless Ass

FapHouse 7 months ago

Lola Crystals taking BIG BLACK COCK backshots by freakymandingo

Lola Crystals taking BIG BLACK COCK backshots by freakymandingo

TransTube.tv 1 year ago

Perseo & Dafne Private Show

HD 2:00 / 20:57

Perseo & Dafne Private Show

Camster 1 year ago

Petra's fifth training

Petra's fifth training

ShemaleSin 1 year ago

Rope bondage, shibari. Dominatrix Nika ties up her Sissy Blaire_18 with ropes and plays with her slender body.

Rope bondage, shibari. Dominatrix Nika ties up her Sissy Blaire_18 with ropes and plays with her slender body.

XHamster 9 months ago

Futa Step-Mommy & GF Blowjob Encouragement with CEI

4K 0:30 / 10:51

Futa Step-Mommy & GF Blowjob Encouragement with CEI

Clips4sale 11 months ago

Sissy Training with Mistress

Sissy Training with Mistress

TrannyGem 7 years ago

Mistress Scar training Sissy Loren compilation

Mistress Scar training Sissy Loren compilation

XHamster 1 year ago

Self-Training No95 Wearing Sanitary Napkins and Tampons and Walking Exposed Part 2

Self-Training No95 Wearing Sanitary Napkins and Tampons and Walking Exposed Part 2

XHamster 7 months ago

Alizzz Storm Private Show

50% 4K 2:00 / 32:57

Alizzz Storm Private Show

Flirt4Free 1 year ago

Pegging the Sissy Slut Hard

Pegging the Sissy Slut Hard

Clips4sale 1 year ago

Huge hands free cumshot sissygasm

Huge hands free cumshot sissygasm

XHamster 2 years ago

Censored porn for beta sissies - FEMDOM JOI

Censored porn for beta sissies - FEMDOM JOI

XHamster 1 year ago

Trans Doll Luvs Riding

Trans Doll Luvs Riding

GayDudesFucking 8 months ago

TRAINING OF MY TS SLAVEGIRL PT 2

59% HD 0:10 / 7:00

TRAINING OF MY TS SLAVEGIRL PT 2

LoyalFans 2 years ago

Gelding Compilation - Effects of Castration, Bilateral Orchiectomy, Goth Girl Reacts

Gelding Compilation - Effects of Castration, Bilateral Orchiectomy, Goth Girl Reacts

Clips4sale 10 months ago

Ladyboy Jizzing hump female dominance domina, Pulverize cunt Sissy

Ladyboy Jizzing hump female dominance domina, Pulverize cunt Sissy

TrannyGem 2 years ago

Jill Pill Gapes Her Ass with Huge Dildo

Jill Pill Gapes Her Ass with Huge Dildo

XHamster 7 months ago

Large Butt Trans Dva Booty Clapping, Wedgie and Anal Gape with Inflatable Sex tool after Flogging her Ass

Large Butt Trans Dva Booty Clapping, Wedgie and Anal Gape with Inflatable Sex tool after Flogging her Ass

ShemaleSin 1 month ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 6 days ago

Huge Ass Shemale Wonder Whore Massive Anal Creampie after being Extreme Anal Gaped with Anal Plug

Huge Ass Shemale Wonder Whore Massive Anal Creampie after being Extreme Anal Gaped with Anal Plug

XHamster 3 weeks ago

Basketball Twinks Bareback in Locker Room After Practice

Basketball Twinks Bareback in Locker Room After Practice

Gay3X 2 years ago

Clit Fucking My Trans Girlfriend in the Ass

Clit Fucking My Trans Girlfriend in the Ass

XHamster 1 month ago

I'll Make You My Perfect Sissy Girlfriend

I'll Make You My Perfect Sissy Girlfriend

Clips4sale 2 years ago

Sniff My Latex Arse & Pussy Ball Kicking CBT, Scent Fetish & Human Furniture Degradation

Sniff My Latex Arse & Pussy Ball Kicking CBT, Scent Fetish & Human Furniture Degradation

XHamster 2 months ago

GOONTARD FOR SHEMALE BIMBOS

63% HD 0:10 / 33:34

GOONTARD FOR SHEMALE BIMBOS

LoyalFans 1 year ago

Cute Blonde Trans Girl Jerks Off Her Big Dick While Talking Dirty

Cute Blonde Trans Girl Jerks Off Her Big Dick While Talking Dirty

Tranny.one 2 years ago

AB067 Foot Worship - Femdom training two sissy 恋足调教-女装娘奴化训练

AB067 Foot Worship - Femdom training two sissy 恋足调教-女装娘奴化训练

AShemaleTube 4 years ago

Camilla Fists and Fucks TS Luna Snow with a Strap-on

66% 0:39 / 18:31

Camilla Fists and Fucks TS Luna Snow with a Strap-on

FapHouse 2 years ago

Sissy Riding a Huge Dildo and Pumps Her Dick with Penispump

61% HD 0:39 / 4:00

Sissy Riding a Huge Dildo and Pumps Her Dick with Penispump

FapHouse 7 months ago

sissypov - clarice darling patiently waiting for her alpha

sissypov - clarice darling patiently waiting for her alpha

TransDoe 2 years ago

Domme Feminizes Then Fucks Sissy

Domme Feminizes Then Fucks Sissy

XHamster 2 months ago

Anal Training Jessica Bloom Caged & Uncaged Sissygasms

70% HD 1:01 / 27:07

Anal Training Jessica Bloom Caged & Uncaged Sissygasms

FapHouse 1 year ago

First-Ever Time Railing Her Faux-Cock In A FuFu Clamp

First-Ever Time Railing Her Faux-Cock In A FuFu Clamp

TrannyGem 2 years ago

Deeper Down the Rabbit Hole

Deeper Down the Rabbit Hole

FapHouse 2 months ago

SISSY TRAINING ON MY BBC

50% 4K 0:28 / 26:26

SISSY TRAINING ON MY BBC

Clips4sale 2 years ago

Mike Swift & David Golden Private Show

HD 2:00 / 59:21

Mike Swift & David Golden Private Show

Flirt4Free 4 weeks ago

Francis Malice Cheerleader 1h Anal Casting Part 1

Francis Malice Cheerleader 1h Anal Casting Part 1

XHamster 2 years ago

Corrine Dittmann Private Show

Corrine Dittmann Private Show

Flirt4Free 3 months ago

The Seductive Twist: Daisy Taylor's Rebellious Massage Adventure

The Seductive Twist: Daisy Taylor's Rebellious Massage Adventure

Fapnado 2 years ago

Sissy Slut Cock Sucking Encouragement with Holly Lou

Sissy Slut Cock Sucking Encouragement with Holly Lou

XHamster 1 month ago

Sexy Trans Gooner Pissing After Anal Fucked and Ass Gaped with Monster Dildo and Creampie

Sexy Trans Gooner Pissing After Anal Fucked and Ass Gaped with Monster Dildo and Creampie

XHamster 4 months ago

Dimitri Caruso Private Show

HD 2:00 / 19:52

Dimitri Caruso Private Show

Flirt4Free 3 years ago

Nylon Sissy Slave - Candle Boxxx HDMP4

37% 0:14 / 13:03

Nylon Sissy Slave - Candle Boxxx HDMP4

Clips4sale 2 years ago

Gloryhole Bitch *FULL-HD*

43% HD 0:03 / 3:59

Gloryhole Bitch *FULL-HD*

Clips4sale 4 years ago

Sissy Bitch Fucked by My Strap-on #FemdomRAW

Sissy Bitch Fucked by My Strap-on #FemdomRAW

XHamster 3 years ago

Femboy thighjobs go ULTRA-KINKY

Femboy thighjobs go ULTRA-KINKY

Gayhub 1 year ago

Unshaved Sissy Milky Masculine Boot on Head Compares Spunk-Pump with Banana and Carrot

Unshaved Sissy Milky Masculine Boot on Head Compares Spunk-Pump with Banana and Carrot

GayCK 6 years ago

Amanda trains her aperture on an XXL toy!

Amanda trains her aperture on an XXL toy!

ShemaleSin 1 week ago

Mistress Ruby's first time fucking a T-Girl

Mistress Ruby's first time fucking a T-Girl

Clips4sale 1 year ago

Teen shocked by teacher and sexy ts getting fucked xxx Analmal Training

Teen shocked by teacher and sexy ts getting fucked xxx Analmal Training

Eporner 3 years ago

Goddess Pussy Worship - Brat Perversions

Goddess Pussy Worship - Brat Perversions

XHamster 2 years ago

Sissy Training Sucking Miss Shell's Futa Cock (UHD WMV)

63% HD 0:26 / 14:00

Sissy Training Sucking Miss Shell's Futa Cock (UHD WMV)

Clips4sale 2 years ago

Inked ftm trans cockridden by a slut

Inked ftm trans cockridden by a slut

Some.Porn 2 years ago

Tiny Sissy Fucked by Daddy Dong King Part 2

Tiny Sissy Fucked by Daddy Dong King Part 2

FapHouse 4 months ago

Playing-white Annete129

Playing-white Annete129

XHamster 1 year ago

Corrine Dittmann Private Show

Corrine Dittmann Private Show

Camster 3 months ago

Prego Sissy Femboy Trap - Clyster - Inflated abdomen

Prego Sissy Femboy Trap - Clyster - Inflated abdomen

TrannyGem 3 years ago

Slutpuppy Training

Slutpuppy Training

ShemaleSin 5 years ago

Stefania Mafra Worships My Feet And Gags On Them (HD1080 MP4)

Stefania Mafra Worships My Feet And Gags On Them (HD1080 MP4)

Clips4sale 3 years ago

TRANS CUTIES - Glamorous Ella Nova And Tranny Natalie Mars End Yoga Class In Hawt Anal Training Session

TRANS CUTIES - Glamorous Ella Nova And Tranny Natalie Mars End Yoga Class In Hawt Anal Training Session

ShemaleSin 3 months ago

46 47 48 49 50

124,004 results found

Related categories

Leashed Challenge Humiliation Edging Cage Handcuffed Master Maledom Superhero Blindfolded Slave Training In Control Prison Submissive Tied Up Spanked Worship Electrified Collar Jail

Narrow your search

sissy training anal training dildo training bdsm training bbc training cock training deepthroat training faggot training slave training blowjob training cum training sissy anal training femboy training 18+ shemale training throat training bi training tranny training training anal slut training training slave

Categories Pornstars

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.