Encouragement Videos - Trans (1,623)

Naught Girl Wants Daddy's Cum- PrincessHaze

Naught Girl Wants Daddy's Cum- PrincessHaze

FapCat 3 years ago

Busty shemale in a hot bikini faps her thick cock

Busty shemale in a hot bikini faps her thick cock

SleazyNEasy 9 months ago

Wife Experience Jerk Off Encouragement

Wife Experience Jerk Off Encouragement

XVideos 2 years ago

River Lynn sent to Crystal Thayer for training

River Lynn sent to Crystal Thayer for training

FapCat 1 week ago

3087 icy sexy trans fucked raw by aaron and romntik

HD 0:30 / 22:19

3087 icy sexy trans fucked raw by aaron and romntik

PornBox 1 year ago

Wife Gets Black Dick Too Creamy so Hubby Encourages her to Clean it WITH HER MOUTH! Please Comment!

Wife Gets Black Dick Too Creamy so Hubby Encourages her to Clean it WITH HER MOUTH! Please Comment!

Ebony8 5 years ago

Lick Spit off My Toes LOSER! Trans Step-sis Makes You Clean Cum Spit And Feet - Jessica Bloom JOI

Lick Spit off My Toes LOSER! Trans Step-sis Makes You Clean Cum Spit And Feet - Jessica Bloom JOI

xHamster 4 months ago

Transwoman Jerks Her Big Cock To Sissygasm

Transwoman Jerks Her Big Cock To Sissygasm

FapCat 1 year ago

Generous Donation

HD 0:39 / 15:20

Generous Donation

FapHouse 1 year ago

Suck Bailey Jays Cock FEMDOM MASTURBATION INSTRUCTION

Suck Bailey Jays Cock FEMDOM MASTURBATION INSTRUCTION

XVideos 9 years ago

Eyes On Her - S34:E11

Eyes On Her - S34:E11

Hoes.tube 2 years ago

Hot Trans Being Naughty On Cam

Hot Trans Being Naughty On Cam

Tranny.one 3 years ago

9481 텔레 BT982 presume DOUBLE 시로 발생 femin

9481 텔레 BT982 presume DOUBLE 시로 발생 femin

4KPorn 1 month ago

Casey and Kat Take Everything 2 at SweetFemdom

Casey and Kat Take Everything 2 at SweetFemdom

XVideos 2 years ago

Husband&#039_s panty fashion show

Husband&#039_s panty fashion show

XVideos 3 years ago

Swallow Your Cum Sissy! CEI Encouragement Compilation - Jessica Bloom

Swallow Your Cum Sissy! CEI Encouragement Compilation - Jessica Bloom

XVideos 1 month ago

Cross Dress and Fuck Him - Ellie Rowyn

Cross Dress and Fuck Him - Ellie Rowyn

XVideos 7 months ago

TS Femdom Dildo Encouragement Suck my Dick Sissy POV Rollplay With Jessica Bloom

TS Femdom Dildo Encouragement Suck my Dick Sissy POV Rollplay With Jessica Bloom

XVideos 2 years ago

Chastity Sissy Slut Anal Orgasm Encouragement - Jessica Bloom

Chastity Sissy Slut Anal Orgasm Encouragement - Jessica Bloom

XVideos 1 year ago

Aussie TS Babe Sasha De Sade

Aussie TS Babe Sasha De Sade

Eporner 2 months ago

O MACHO CHEGOU E MOSTROU A SURPRESINHA

O MACHO CHEGOU E MOSTROU A SURPRESINHA

XVideos 6 months ago

Jerking Off Your Tiny Dick With Step-Mommy Ellie Rowyn

Jerking Off Your Tiny Dick With Step-Mommy Ellie Rowyn

XVideos 2 months ago

Sissy Training - Sissygasm Encouragement Jessica Bloom Compilation

Sissy Training - Sissygasm Encouragement Jessica Bloom Compilation

XVideos 3 years ago

TRANSFIXED - Christy Love Encourages Trans Clients To Fuck During Nude Massage

TRANSFIXED - Christy Love Encourages Trans Clients To Fuck During Nude Massage

XVideos 3 years ago

The Cum Stealing Femboy Witch

The Cum Stealing Femboy Witch

XVideos 2 years ago

KAREN KATASTROPHE

KAREN KATASTROPHE

TransTube.tv 11 months ago

Giving it to the neighbor in the backyard with just panties on

Giving it to the neighbor in the backyard with just panties on

XVideos 1 year ago

MistyBubbleWush's Guide to Sissy Training (2024)

MistyBubbleWush's Guide to Sissy Training (2024)

xHamster 1 year ago

futa ex gf will take you back if you worship her - full video on Veggiebabyy Manyvids

futa ex gf will take you back if you worship her - full video on Veggiebabyy Manyvids

XVideos 2 years ago

Corset Confinement - Futa Sissy ASMR Discipline Session | METAVULGAR ASMR JOI

Corset Confinement - Futa Sissy ASMR Discipline Session | METAVULGAR ASMR JOI

XVideos 1 week ago

JockPussy: Thick Declan Gray feels like nailed rough

JockPussy: Thick Declan Gray feels like nailed rough

GayPorn.video 2 years ago

Pan College Fuckfest

Pan College Fuckfest

Some.Porn 1 month ago

chastity office bitch spitroasted and quadruple creampied - full video on Veggiebabyy Manyvids

chastity office bitch spitroasted and quadruple creampied - full video on Veggiebabyy Manyvids

xHamster 11 months ago

La culeo a travesti y saco semen parte 6 final

La culeo a travesti y saco semen parte 6 final

XVideos 1 year ago

Jessica Bloom's Sissy Slut Academy Introduction Interview

Jessica Bloom's Sissy Slut Academy Introduction Interview

xHamster 3 years ago

JockPussy - Jock Jay James next to Tommy Tanner fingering

JockPussy - Jock Jay James next to Tommy Tanner fingering

IceGayPorn 2 years ago

Transgender women Aubrey Kate & Chelsea Marie fuck Pierce Paris!

Transgender women Aubrey Kate & Chelsea Marie fuck Pierce Paris!

StarWank 1 year ago

Took my sissy on holiday and pegged her

Took my sissy on holiday and pegged her

xHamster 8 months ago

Eat My Futa Asshole

66% HD 0:39 / 10:38

Eat My Futa Asshole

FapHouse 1 month ago

Transgender women Aubrey Kate & Chelsea Marie fuck Pierce Paris!

Transgender women Aubrey Kate & Chelsea Marie fuck Pierce Paris!

HQBang 1 year ago

I Bet My Chisel is Larger Than Yours!

I Bet My Chisel is Larger Than Yours!

TransTube.tv 11 months ago

JockPussy: Tommy Tanner plowed by uncut cock Tanner in shower

JockPussy: Tommy Tanner plowed by uncut cock Tanner in shower

GayPorn.video 2 years ago

The Internet is Making You HOMO ft Goddess Colleen

The Internet is Making You HOMO ft Goddess Colleen

TransTube.tv 9 months ago

pov massage and pussy eating for your huge cock futa wife - full video on Veggiebabyy Manyvids

pov massage and pussy eating for your huge cock futa wife - full video on Veggiebabyy Manyvids

xHamster 3 months ago

Strapon Sissy Encouragement

HD 0:39 / 10:36

Strapon Sissy Encouragement

FapHouse 3 months ago

Shemales Chelsea Marie and Aubrey Kate having anal threesome with Pierce

Shemales Chelsea Marie and Aubrey Kate having anal threesome with Pierce

Fapnado 3 years ago

TGIRLS.XXX: I Love a Girl in Denims

TGIRLS.XXX: I Love a Girl in Denims

xHamster 1 year ago

JockPussy: Super juicy Declan bareback begging

JockPussy: Super juicy Declan bareback begging

GayPornoTube 2 years ago

The "Gay-for-pay" Truth: You're Homosexual ft Trans Female dom

The "Gay-for-pay" Truth: You're Homosexual ft Trans Female dom

TransTube.tv 8 months ago

You're HOMO for Large Nads ft Queen Colleen

You're HOMO for Large Nads ft Queen Colleen

TransTube.tv 10 months ago

Black Crossdresser Getting Ass Pounded By Fuck Machine Until Having Prostate Orgasme

Black Crossdresser Getting Ass Pounded By Fuck Machine Until Having Prostate Orgasme

xHamster 2 months ago

Petite Slim Blonde Trap Strokes her Cute Pink Boy Clit

Petite Slim Blonde Trap Strokes her Cute Pink Boy Clit

Eporner 1 year ago

Promise me all ur loads 2022 Trans JOI

Promise me all ur loads 2022 Trans JOI

xHamster 3 years ago

My Yoga Instructor - S1:E2

My Yoga Instructor - S1:E2

Hoes.tube 2 years ago

Wife Discovers Sissy Spouse

Wife Discovers Sissy Spouse

MatureTubeHere 10 months ago

JockPussy - Tanner with Tommy Tanner in the douche

JockPussy - Tanner with Tommy Tanner in the douche

GayVids 1 year ago

Adorable Brunette TS Alisa

Adorable Brunette TS Alisa

Eporner 2 months ago

TS PMV - Physical — Dua Lipa Encourages You to Jerk Off

TS PMV - Physical — Dua Lipa Encourages You to Jerk Off

BeMyHole 4 years ago

Lonely Goddess of love Crystal Thayer and the goddess of lust River Lynn meets

Lonely Goddess of love Crystal Thayer and the goddess of lust River Lynn meets

Sheshaft 2 weeks ago

Friends Come First - S1:E5

Friends Come First - S1:E5

Hoes.tube 2 years ago

EXCITED FOR ME - muscle boi teaches u the essentials of being a WENCH for PRIDE

EXCITED FOR ME - muscle boi teaches u the essentials of being a WENCH for PRIDE

ShemaleSin 1 year ago

Splendid trans goddess giving bisexous encouragement

Splendid trans goddess giving bisexous encouragement

TransTube.tv 9 months ago

FalconStudios.com: Getting Off next to defined gymnast

FalconStudios.com: Getting Off next to defined gymnast

UrGayPorn 1 year ago

6th part - mommy turns you into a sissy

6th part - mommy turns you into a sissy

xHamster 1 year ago

Trap In Black Stockings Stroking Her Thick Penis

Trap In Black Stockings Stroking Her Thick Penis

Pornwhite 1 year ago

FTM Femboys Tear Up While Dad Films and Provides encouragement trio

FTM Femboys Tear Up While Dad Films and Provides encouragement trio

TrannyGem 2 years ago

Transsexual Tease Tyra Scotts Ultimate Dildo Delight

Transsexual Tease Tyra Scotts Ultimate Dildo Delight

4KPorn 3 weeks ago

Sissy Training - Sissygasm Encouragement Jessica Bloom Compilation

Sissy Training - Sissygasm Encouragement Jessica Bloom Compilation

TransTube.tv 5 months ago

Trap In Black Stockings Stroking Her Thick Cock

Trap In Black Stockings Stroking Her Thick Cock

Katestube 1 year ago

Seductive Surrender Hoe 4

Seductive Surrender Hoe 4

Hoes.tube 3 weeks ago

Hot TS Sienna Grace steaming hot scene with beautiful babe Mandy Muse

Hot TS Sienna Grace steaming hot scene with beautiful babe Mandy Muse

Tranny.one 6 years ago

Smokin' mistresse Shelly

Smokin' mistresse Shelly

ShemaleSin 1 year ago

2550 jess royan fuck draw by estelle and aaron

66% HD 0:30 / 26:08

2550 jess royan fuck draw by estelle and aaron

PornBox 11 months ago

Ramon Nomar spanks Trans Aubrey Kate during hardcore ass pumping penetration

Ramon Nomar spanks Trans Aubrey Kate during hardcore ass pumping penetration

Fapnow 2 years ago

Extreme Closeup Cumslut Encouragement

Extreme Closeup Cumslut Encouragement

FapHouse 9 months ago

Gigantic Bap Trans Humps Gym Slave's Culo while he's in restrain bondage - Lucy Hart - Powerful

Gigantic Bap Trans Humps Gym Slave's Culo while he's in restrain bondage - Lucy Hart - Powerful

TransTube.tv 9 months ago

Lonely Goddess of love Crystal Thayer and the goddess of lust River Lynn meets

Lonely Goddess of love Crystal Thayer and the goddess of lust River Lynn meets

Yeswegays 2 weeks ago

Trans Foot Fetish - Cum Eating Instructions Jessica Bloom JoI CEI

Trans Foot Fetish - Cum Eating Instructions Jessica Bloom JoI CEI

ShemaleSin 3 years ago

gang bang in sauna with stratgh and transexuel

gang bang in sauna with stratgh and transexuel

PissVids 1 year ago

Cross Dress For Your Boss: Public Humiliation Dirty Talk & Crossdressing Encouragement

Cross Dress For Your Boss: Public Humiliation Dirty Talk & Crossdressing Encouragement

xHamster 2 years ago

FalconStudios: Plump and horny crossdresser rimming

FalconStudios: Plump and horny crossdresser rimming

GayPornoTube 3 years ago

TS Female domination Fake-sausage Encouragement Deep-throat my Penis Sissy POINT OF VIEW Rollplay

TS Female domination Fake-sausage Encouragement Deep-throat my Penis Sissy POINT OF VIEW Rollplay

TransTube.tv 9 months ago

Aussie Transgender hot girl Sasha de Sade

Aussie Transgender hot girl Sasha de Sade

Trashreality 1 year ago

Hunny Bunnies - S5:E10

Hunny Bunnies - S5:E10

Hoes.tube 2 years ago

bareback complete amator french porn video homemade with french twink wit big cock fucked anal by their straight frienc curious for rough sex, exihb or public cruising

HD 0:30 / 18:34

bareback complete amator french porn video homemade with french twink wit big cock fucked anal by their straight frienc curious for rough sex, exihb or public cruising

PornBox 2 years ago

ZZCast Keiran Inside The House

ZZCast Keiran Inside The House

Hoes.tube 1 year ago

sneaker domination for jordan by scally boy dominant with jogging and sport fetish outfitd

sneaker domination for jordan by scally boy dominant with jogging and sport fetish outfitd

AnalVids 2 years ago

the sexy transboy ftm billy vega used by romantik in paris by daddy

HD 0:30 / 21:23

the sexy transboy ftm billy vega used by romantik in paris by daddy

PornBox 2 years ago

Total Story of Gamer Man Sissified and Corrupted

Total Story of Gamer Man Sissified and Corrupted

TrannyGem 8 months ago

GROOBY.CLUB: EMMY ANGELES IS FEELING NAUGHTY!

GROOBY.CLUB: EMMY ANGELES IS FEELING NAUGHTY!

Fapnado 1 year ago

Holly Michaels Cast Alina Li Ep8 - S4:E4

Holly Michaels Cast Alina Li Ep8 - S4:E4

Hoes.tube 2 years ago

EBONY-TRANSSEXUALS: The Devil is in the Details

EBONY-TRANSSEXUALS: The Devil is in the Details

ShemaleSin 1 year ago

Horny Ladyboy Jerking Her Monster Shecock On Cam

Horny Ladyboy Jerking Her Monster Shecock On Cam

FapCat 1 year ago

bareback bukkake with transexuel in sauna

bareback bukkake with transexuel in sauna

PissVids 1 year ago

Blow job POV with encouragement

HD 1:01 / 11:16

Blow job POV with encouragement

FapHouse 2 years ago

NEGAO BRASILEIRO COMENDO HOMEM TRANS COM BUCETA PELA PRIMEIRA VEZ

NEGAO BRASILEIRO COMENDO HOMEM TRANS COM BUCETA PELA PRIMEIRA VEZ

XVideos 4 months ago

blond femboy fucke draw by straight curiouis

HD 0:30 / 14:11

blond femboy fucke draw by straight curiouis

PornBox 1 year ago

Jerk Off With Me Vibes XXX

Jerk Off With Me Vibes XXX

ShemaleSin 1 year ago

Encourages You To Jerk Off

Encourages You To Jerk Off

its.PORN 6 months ago

Sissy Loser Encouraged by Alpha Beauties to Clean there Cum Filled Condoms Pathetic Loser

Sissy Loser Encouraged by Alpha Beauties to Clean there Cum Filled Condoms Pathetic Loser

ShemaleSin 4 years ago

4633 jess oryan fucked raw by straigh arb big cock

HD 0:30 / 14:58

4633 jess oryan fucked raw by straigh arb big cock

PornBox 4 months ago

Shemale wants you deep in her ass

Shemale wants you deep in her ass

MyLust 5 years ago

This Might Be the HOTTEST JOI CLIP YOU’VE EVER SEEN!!!

This Might Be the HOTTEST JOI CLIP YOU’VE EVER SEEN!!!

ShemaleSin 4 years ago

Become a cock-sucking sissy and worship your Mistress in femdom fetish

Become a cock-sucking sissy and worship your Mistress in femdom fetish

Jizzberry 3 years ago

Jessica Bloom Big Trans Cock Tease JOI CEI Edging with Fleshlight Self Suck and Cumplay

HD 0:39 / 24:46

Jessica Bloom Big Trans Cock Tease JOI CEI Edging with Fleshlight Self Suck and Cumplay

FapHouse 10 months ago

Shemale With A Huge Cock Gets Wild

Shemale With A Huge Cock Gets Wild

Eporner 3 years ago

Heshe Jerking Off And Dildoing Her Ass

Heshe Jerking Off And Dildoing Her Ass

Sheshaft 5 years ago

Horny blonde tranny desires anal intercourse with a shemale friend

Horny blonde tranny desires anal intercourse with a shemale friend

FapCat 7 months ago

Brunette Casey Calvert eats cum after passionate ass banging

Brunette Casey Calvert eats cum after passionate ass banging

FapCat 1 month ago

part 2: strap on sucking and chastity pegging with FLR GF - full video on Veggiebabyy Manyvids

part 2: strap on sucking and chastity pegging with FLR GF - full video on Veggiebabyy Manyvids

xHamster 2 months ago

Tranny KORRA DEL RIO: FREAKY DILDO GAPING!

Tranny KORRA DEL RIO: FREAKY DILDO GAPING!

TransHero 1 year ago

Sensual Shemale Enjoys Jerking Off Her Johnson On Chair

Sensual Shemale Enjoys Jerking Off Her Johnson On Chair

Pornwhite 6 months ago

Big Crazy Sexy Melons - S4:E5

Big Crazy Sexy Melons - S4:E5

Hoes.tube 2 years ago

Gingerhead Tranny Faps Her Cock To Sissygasm

Gingerhead Tranny Faps Her Cock To Sissygasm

FapCat 9 months ago

Jock Conditioning For The Closeted Faggot

Jock Conditioning For The Closeted Faggot

ShemaleSin 1 year ago

STEPBROTHERS UNBELIEVABLY MASSIVE COCK WILL LEAVE YOU SPEECHLESS! S37E2

STEPBROTHERS UNBELIEVABLY MASSIVE COCK WILL LEAVE YOU SPEECHLESS! S37E2

CrazyPorn 3 months ago

TGIRLS XXX - Ayesha Green Erotic Solo Masturbation In Sofa

TGIRLS XXX - Ayesha Green Erotic Solo Masturbation In Sofa

Trashreality 5 months ago

TBabe fucks her cis chick roommate after her unsuccessful date - Lena Moon & Skylar Snow

TBabe fucks her cis chick roommate after her unsuccessful date - Lena Moon & Skylar Snow

TransHero 3 years ago

Shemale Goddess Fapping Her Huge Dick

Shemale Goddess Fapping Her Huge Dick

Katestube 7 months ago

Sissygasm Guide & How A Wonderful Doxy Cleans Up Jessica Bloom

Sissygasm Guide & How A Wonderful Doxy Cleans Up Jessica Bloom

ShemaleSin 3 years ago

3 4 5 6 7

1,623 results found

Related categories

Compilation Orgasm Jerk Off Encouragement Solo Masturbation Thai Solo Horny Amateur MILF Solo Squirt Messy Facials Jerking Off Public Handjob Handjob Mom Squirt Anal Jizz Cum Swallow Compilation Premature Ejaculation Blowjob & Cumshot Beautiful Girl Nerdy Teen 18+ Cum Drenched Asian Anal

Narrow your search

jerk off encouragement bi encouragement sissy encouragement gay encouragement encouragement pov bisexual encouragement cum eating encouragement cum encouragement joi encouragement encouragement mom masturbation encouragement jerk off encouragement mom jerk off instructions masturbation encouragement jerk off encouragement ass jerkoff encouragement mom encouragement jerk off encouragement step sister british encouragement step sister encouragement encouragement step sister

Categories Pornstars

Categories Pornstars

Legal

Terms of Service Privacy Statement Notice and Action Policy (Link Removal) DMCA / Copyright Acceptable Content Policy Digital Services Act 2257

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.

© 2025 Pornmd.com. All rights reserved.