Training Videos - Trans (28,088)

Sissy Maid Teaching

Sissy Maid Teaching

TrannyGem 4 years ago

Rock femboy anal training, gaping, and self facial

Rock femboy anal training, gaping, and self facial

Amateur8 2 weeks ago

◆ 3D FUTA Beauty’s First Time Turns Into Intense Pleasure as Toys & Big Cock Bring Her to Orgasm

◆ 3D FUTA Beauty’s First Time Turns Into Intense Pleasure as Toys & Big Cock Bring Her to Orgasm

SleazyNEasy 1 week ago

Cuckold Bf Confession - Sorry for CUCKOLDING you

Cuckold Bf Confession - Sorry for CUCKOLDING you

MenGem 1 year ago

Golden Shower wets my SISSY gurlfriend before FISTING cumshot

Golden Shower wets my SISSY gurlfriend before FISTING cumshot

xHamster 8 months ago

Daddy Loves His Little Fag - Slave Training

Daddy Loves His Little Fag - Slave Training

xHamster 2 years ago

Doll training - dildo gag

Doll training - dildo gag

xHamster 1 month ago

”Milf's Sissy Chastity Training #BratPerversions”

”Milf's Sissy Chastity Training #BratPerversions”

Rainblow 1 week ago

TouchedFetish - Latex Sissy Training - Rubber Crossdresser Husband is humiliated by femdom domina with strapon & paddel - Couple

TouchedFetish - Latex Sissy Training - Rubber Crossdresser Husband is humiliated by femdom domina with strapon & paddel - Couple

xHamster 2 years ago

Redhead Trans Girl Slowly Reveals a Surprise You Didn't Expect

Redhead Trans Girl Slowly Reveals a Surprise You Didn't Expect

xHamster 3 weeks ago

”GENDER X TS cheerleader rides on big black cock - Smash Thompson,Ella Hollywood”

”GENDER X TS cheerleader rides on big black cock - Smash Thompson,Ella Hollywood”

TransHero 4 years ago

”Freaky Sissy Trainers #BratPerversions”

”Freaky Sissy Trainers #BratPerversions”

429Men 1 week ago

”TGIRLS XXX - MILF Eris Jolie On Her Kitchen Masturbates”

”TGIRLS XXX - MILF Eris Jolie On Her Kitchen Masturbates”

LesbianBliss 1 month ago

Sissy bitch cock locked in chastity cum hands free

Sissy bitch cock locked in chastity cum hands free

xHamster 5 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 3 days ago

Gf put her femboy in underwear to observe me fap off

Gf put her femboy in underwear to observe me fap off

TrannyGem 2 years ago

Uber-cute Femboy in Fishnets Teaches his Bulls eye until he Pops on Himself

Uber-cute Femboy in Fishnets Teaches his Bulls eye until he Pops on Himself

5Gays 1 year ago

put two mitts in the booty of her sissy fuckslut. handballing

put two mitts in the booty of her sissy fuckslut. handballing

TrannyGem 2 years ago

Hot Shemale on the Fuck Yeah Machine - Red Pvc & Giant Dildo Depth Training Extreme Deep Anal

Hot Shemale on the Fuck Yeah Machine - Red Pvc & Giant Dildo Depth Training Extreme Deep Anal

xHamster 2 weeks ago

G066 - Cum Swallow Compilation 2

58% 1:01 / 15:24

G066 - Cum Swallow Compilation 2

FapHouse 7 months ago

Trans Ria Bentley Toys Her Ass and Gives JOI in School Uniform

Trans Ria Bentley Toys Her Ass and Gives JOI in School Uniform

xHamster 9 months ago

Anouk Tgirl Wench - Bareback Facefuck BBC Destroys her Sissy Butt and Mouth in 4 hrs - Full Clip

Anouk Tgirl Wench - Bareback Facefuck BBC Destroys her Sissy Butt and Mouth in 4 hrs - Full Clip

SortPorn 3 years ago

CBT and a Footjob

CBT and a Footjob

ShemaleSin 8 months ago

this babemale Ariel trains guy Mmm

this babemale Ariel trains guy Mmm

TrannyGem 6 years ago

Sissy hubby rides wife's bbc strapon

Sissy hubby rides wife's bbc strapon

xHamster 5 months ago

CHASTITY slave CUMS while PEGGING after training with some XXL toys

CHASTITY slave CUMS while PEGGING after training with some XXL toys

xHamster 10 months ago

Drag Queen and Woman Makeover Transformation - Cleavage and Eyeliner

Drag Queen and Woman Makeover Transformation - Cleavage and Eyeliner

xHamster 1 year ago

Dildo Masturbation 3 - S025.1

Dildo Masturbation 3 - S025.1

xHamster 3 weeks ago

Sissy Doll Fucking in a Pegging Date

Sissy Doll Fucking in a Pegging Date

xHamster 3 months ago

feminisation training

feminisation training

ShemaleSin 1 month ago

Santa's little helper Maddy loves riding her big toys and drilling her ass!

Santa's little helper Maddy loves riding her big toys and drilling her ass!

xHamster 1 month ago

Sissy Crossdresser Cuckhold Spanked, Fastened, Gagged, And Chastised By Hawt Femdom Mistresse

Sissy Crossdresser Cuckhold Spanked, Fastened, Gagged, And Chastised By Hawt Femdom Mistresse

BigTitsLust 4 years ago

Piss drinking small penis bisexual sissy cuckold

Piss drinking small penis bisexual sissy cuckold

xHamster 1 year ago

Sissy Wench Jessica Bloom Plowd Hard By Biggest Ebony Weenie On Bang Machine Multiple Anal Sissygasms

Sissy Wench Jessica Bloom Plowd Hard By Biggest Ebony Weenie On Bang Machine Multiple Anal Sissygasms

ShemaleSin 1 week ago

Khloe Kay Anal Training With Huge Dildo

Khloe Kay Anal Training With Huge Dildo

VipTube 2 weeks ago

Woman fucks man with long dildo #300 practicing for lesbian encounter PART 1

Woman fucks man with long dildo #300 practicing for lesbian encounter PART 1

xHamster 11 months ago

Ria Bentley Succumbs to Raw Anal by Gigantic BBC

Ria Bentley Succumbs to Raw Anal by Gigantic BBC

xHamster 1 year ago

Supreme North Anal Slut Training

Supreme North Anal Slut Training

DrTuber 2 weeks ago

Shemale + Shemale Slave Training

Shemale + Shemale Slave Training

BeMyHole 3 years ago

FULL MOVIE Lena Vesper Railed By Hankeys Seahorse Bang Machine

FULL MOVIE Lena Vesper Railed By Hankeys Seahorse Bang Machine

ShemaleSin 3 months ago

Sissy Maid Crossdresser Doxy Amanda Kiss Gets Plugged Bound Up And Abased By Femdom Mastix Nyx

Sissy Maid Crossdresser Doxy Amanda Kiss Gets Plugged Bound Up And Abased By Femdom Mastix Nyx

BigTitsLust 4 years ago

Super Ultimate Compilation

Super Ultimate Compilation

xHamster 5 months ago

Mistress Training Sissy Femboy

Mistress Training Sissy Femboy

xHamster 3 years ago

Small Penis Femboy Pissing and Fucking Her Fat Ass with Cucumber

Small Penis Femboy Pissing and Fucking Her Fat Ass with Cucumber

xHamster 1 week ago

You Won’t Believe Where FUTA MILF Puts That Toy ⁕ 3D Porn

You Won’t Believe Where FUTA MILF Puts That Toy ⁕ 3D Porn

HentaiGem 2 weeks ago

Cross Dresser Training

Cross Dresser Training

SexTubeSpot 7 years ago

Mistress Baton's Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

Mistress Baton's Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

xHamster 1 month ago

Antonella Morena Anal Training With Ass Close Up

Antonella Morena Anal Training With Ass Close Up

ProPorn 2 weeks ago

Desperate Pipe Tramp: Deep Mouth Teaching

Desperate Pipe Tramp: Deep Mouth Teaching

TrannyGem 1 month ago

Transwhore slave has to do it herself and offer ass

Transwhore slave has to do it herself and offer ass

xHamster 2 days ago

HANDS FREE SISSYGASM CUMSHOT from Aneros MGX Syn Trident

HANDS FREE SISSYGASM CUMSHOT from Aneros MGX Syn Trident

xHamster 2 years ago

Edging JOI Ryley Rails

66% HD 1:01 / 5:27

Edging JOI Ryley Rails

FapHouse 2 months ago

Full Crossdressing Transformation

Full Crossdressing Transformation

xHamster 3 years ago

Each one detests u whiteboi, even your headmistress Roxy detests u sissy for BNWO girl scarlett ebony

Each one detests u whiteboi, even your headmistress Roxy detests u sissy for BNWO girl scarlett ebony

ShemaleSin 3 years ago

anal invasion training of a sissy superslut

anal invasion training of a sissy superslut

TransTube.tv 1 year ago

Femboy training part 1: The Back Arch

Femboy training part 1: The Back Arch

Gayhaus 1 year ago

Training A Sissy How To Suck Cock

Training A Sissy How To Suck Cock

BoyFriendTV 5 years ago

Pink sissy bimbo floozy trixie training her holes

Pink sissy bimbo floozy trixie training her holes

ShemaleSin 2 weeks ago

ScarletteLoves - Bi Edition - Futa Training

ScarletteLoves - Bi Edition - Futa Training

VipTube 1 week ago

Get rid of your cock - The Lady of Feminisation gives you sissy cunt a nice cameltoe panty

Get rid of your cock - The Lady of Feminisation gives you sissy cunt a nice cameltoe panty

xHamster 2 years ago

Sissy Instructing Part two

Sissy Instructing Part two

4Gay 5 months ago

Validate Your New Feminine Identity - Gender Transformation

57% HD 1:01 / 21:20

Validate Your New Feminine Identity - Gender Transformation

FapHouse 1 month ago

Supreme North Anal Training In The Hotel Room

Supreme North Anal Training In The Hotel Room

DrTuber 2 weeks ago

Bisex Training and Interracial Homosexual Dream

Bisex Training and Interracial Homosexual Dream

ShemaleSin 2 days ago

Femboy Assfuck Spreading With A Big Node Faux-cock

Femboy Assfuck Spreading With A Big Node Faux-cock

5Gays 10 months ago

Mercedes Trujilo Gets Deepthroat Training Before Riding BBC

Mercedes Trujilo Gets Deepthroat Training Before Riding BBC

Nuvid 2 weeks ago

G094 - Back to Back Swallows!

70% HD 0:39 / 4:38

G094 - Back to Back Swallows!

FapHouse 1 month ago

Sissy Blaire_18 in chastity belt. Dominatrix Nika plays with his balls with a vibrator. Feminized man in pink skirt

Sissy Blaire_18 in chastity belt. Dominatrix Nika plays with his balls with a vibrator. Feminized man in pink skirt

xHamster 9 months ago

Finally all in with 15 inch King Cock dildo

Finally all in with 15 inch King Cock dildo

xHamster 3 months ago

FAPPING MY PROSTATE HANDSFREE JIZM

FAPPING MY PROSTATE HANDSFREE JIZM

GayDudesFucking 2 weeks ago

Sexy Trans Secretary Discipline Encounter With The Boss

Sexy Trans Secretary Discipline Encounter With The Boss

FreePorn8 3 weeks ago

Domme Mercer Sissy Virginity Sub Teased and Humiliated, Denied and Locked in The Vice

Domme Mercer Sissy Virginity Sub Teased and Humiliated, Denied and Locked in The Vice

TransTube.tv 1 year ago

Ultra-naughty Masseuse Latex Glove Fisting with XXL rosebud and GAPE for Sissy Hoe by Mistress Mercer

Ultra-naughty Masseuse Latex Glove Fisting with XXL rosebud and GAPE for Sissy Hoe by Mistress Mercer

TransTube.tv 1 year ago

She Has a Job to Do Before Bedtime

She Has a Job to Do Before Bedtime

xHamster 1 month ago

Happy Ending of the Training

Happy Ending of the Training

xHamster 7 months ago

Slut Training Part 1

62% HD 1:01 / 6:18

Slut Training Part 1

FapHouse 1 year ago

Joni Laws stretches her gap with HANKEYS TOYS Aaron Klein XL and Kthulu XXL

Joni Laws stretches her gap with HANKEYS TOYS Aaron Klein XL and Kthulu XXL

SortPorn 2 months ago

The Only Way A Sissy Should Be Instructed To Jizz

The Only Way A Sissy Should Be Instructed To Jizz

TrannyGem 2 years ago

Cum ride with me

Cum ride with me

xHamster 1 year ago

Huge uncut cock in the mouth close-up , filled the throat with Stepdaddy's sperm!

66% 0:39 / 3:41

Huge uncut cock in the mouth close-up , filled the throat with Stepdaddy's sperm!

FapHouse 2 years ago

Marvelous gothic sissy cutie giant anal gape

Marvelous gothic sissy cutie giant anal gape

ShemaleSin 4 years ago

Slut Training With Adelaide Asterix JOI

Slut Training With Adelaide Asterix JOI

VipTube 2 weeks ago

How About a 35 Minute Video with Fucking - Sucking and Lots of Hot Sexy Fun? Starring Bailey Love - Lexi and Riley. the Training

75% HD 1:01 / 35:10

How About a 35 Minute Video with Fucking - Sucking and Lots of Hot Sexy Fun? Starring Bailey Love - Lexi and Riley. the Training

FapHouse 1 year ago

Mistress streches urethra peehole of her sissy with dilator edging

Mistress streches urethra peehole of her sissy with dilator edging

FapHouse 2 weeks ago

Bad Dragon XL Flint savagely destroys SlutBoyTO's hole

Bad Dragon XL Flint savagely destroys SlutBoyTO's hole

xHamster 7 months ago

Thrall Kelly Jordyn cuffed and to suck Nyxi's dick.

Thrall Kelly Jordyn cuffed and to suck Nyxi's dick.

ShemaleSin 4 years ago

Can I truly get this supah-long plaything all the way in my booty? Emily Adaire's assfuck-bootcamp - day three

Can I truly get this supah-long plaything all the way in my booty? Emily Adaire's assfuck-bootcamp - day three

TrannyGem 10 months ago

Lights, Cameras, Sissy!

Lights, Cameras, Sissy!

ShemaleSin 2 months ago

POV Sissy Deep Throat and Cum Eat Humiliation Domination Striptease While Sucking

67% HD 1:01 / 23:05

POV Sissy Deep Throat and Cum Eat Humiliation Domination Striptease While Sucking

FapHouse 3 months ago

Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI

Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI

xHamster 1 year ago

Huge hands free cumshot sissygasm

Huge hands free cumshot sissygasm

xHamster 1 year ago

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

Wondrous Fem Dom and Mature Shemale Predominate and Fem a Sissy

TrannyGem 4 years ago

Humiliating Cock Sucking Training For Sissy

Humiliating Cock Sucking Training For Sissy

AbTranny 6 years ago

FAT BOOTY Sissy rides dildo HARD with CREAMY GAPE

FAT BOOTY Sissy rides dildo HARD with CREAMY GAPE

xHamster 3 years ago

Wifey makes vid of sissy hubby romping himself in the backside like a tramp.

Wifey makes vid of sissy hubby romping himself in the backside like a tramp.

Gayhub 5 months ago

Sissy in ebony vinyl

Sissy in ebony vinyl

Gayhaus 2 months ago

Making My Cock Explode

Making My Cock Explode

ShemaleSex 14 hours ago

Urethral Tube Stimulation with Chastity Cage

Urethral Tube Stimulation with Chastity Cage

xHamster 3 months ago

”Daisy Taylor wears miniskirt without panties on the train! This makes Johnny horny as fuck!”

”Daisy Taylor wears miniskirt without panties on the train! This makes Johnny horny as fuck!”

429Men 1 week ago

Sasha de Sade Housemaid Strapon Training With Saskia

Sasha de Sade Housemaid Strapon Training With Saskia

Nuvid 1 week ago

Lick Cummies Movie

Lick Cummies Movie

Transvids.tv 1 year ago

Supreme North Anal Slut Training

Supreme North Anal Slut Training

DrTuber 1 week ago

Chinese shelady In Public instruct

Chinese shelady In Public instruct

TrannyGem 5 years ago

Wife's Imposed Feminization: Hormones, Ball Removal, Permanent Makeup, Penis Reduction & More!

Wife's Imposed Feminization: Hormones, Ball Removal, Permanent Makeup, Penis Reduction & More!

FapHouse 1 month ago

Sissy Whore Practice Deepthroat Fellatio Training Sucking Sex toy

Sissy Whore Practice Deepthroat Fellatio Training Sucking Sex toy

ShemaleSin 11 months ago

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

57% 1:01 / 9:30

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

FapHouse 6 months ago

Booty Smashed Femboy Pops Super Hot Forearms Free-For-All (Opened Up Crevasse Luvs)

Booty Smashed Femboy Pops Super Hot Forearms Free-For-All (Opened Up Crevasse Luvs)

TrannyGem 4 years ago

Futanari Jessie from Pokemon

Futanari Jessie from Pokemon

xHamster 4 months ago

Brunette TS Saki Cruise broken in by Charlotte Sartre with rough fucking

Brunette TS Saki Cruise broken in by Charlotte Sartre with rough fucking

UrGayPorn 6 months ago

Two dominating girlfriends and fucking a common sissy slut

Two dominating girlfriends and fucking a common sissy slut

xHamster 9 months ago

Auntie caught her perverted sissy stepson masturbating on her clothes !!!

Auntie caught her perverted sissy stepson masturbating on her clothes !!!

xHamster 1 year ago

”A Gym Just For Us 2”

”A Gym Just For Us 2”

TransHero 1 month ago

Chastity cage after a week of sissy training, dreaming of a daddy's cock

Chastity cage after a week of sissy training, dreaming of a daddy's cock

xHamster 2 years ago

Sissy Cheating Anjali Facefuck By Sir

Sissy Cheating Anjali Facefuck By Sir

TrannyGem 8 months ago

Lesbian Shemale Making Love in Japanese College Uniform

63% 1:01 / 35:44

Lesbian Shemale Making Love in Japanese College Uniform

FapHouse 11 months ago

Having a Hard Time 6: Shemale Jane's HJ From Jessica & BJ From Rachel

66% HD 1:01 / 14:39

Having a Hard Time 6: Shemale Jane's HJ From Jessica & BJ From Rachel

FapHouse 2 weeks ago

Sissy Intense Anal Fucking with Rockhard Monstercock

Sissy Intense Anal Fucking with Rockhard Monstercock

xHamster 1 month ago

Trans Ria Bentley Trains Stepdaughter Eden Espi For Anal Sex 7 Min

Trans Ria Bentley Trains Stepdaughter Eden Espi For Anal Sex 7 Min

AbTranny 3 months ago

Is this an anal invasion fucktoy or a traffic cone? Emily Adaire's anal invasion-bootcamp - day 8

Is this an anal invasion fucktoy or a traffic cone? Emily Adaire's anal invasion-bootcamp - day 8

TrannyGem 3 years ago

sexy sissy whore is being anal fucked by daddy

sexy sissy whore is being anal fucked by daddy

xHamster 1 year ago

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