SHEMALE • PROSTATE 305 videos

Popular Latest Top rated

16:31

Miyuki onanism 2-2

2 days ago

HDSex

shemale, cumshot, small cock, japanese, big cock, prostate
20:52

Pink outfit femboy red lipstick 20 minutes of prostate play - numerous postures no forearm cum

3 weeks ago

ShemaleTaxi

orgasm, femboy, amateur, dildo, massage, prostate
16:13

Anal orgasms, unexperienced, shemale hands free cum

1 month ago

XXXVogue

stockings, prostate, orgasm, lingerie, heels, anal orgasm, hands free
25:33

TRANNY EXTREME trio - vignette six

1 month ago

ShemaleMovie

ass, outdoor, prostate
37:37

Prostate Play Rides Dildo in Hardcore Trans Sex Doll Fuck

1 month ago

JizzBunker

amateur, crossdresser, dildo, shemale, prostate, doll
16:00

Sexy Trans Gets Fucked By Doctor During Prostate Exam

2 months ago

AShemaleTube

exam, shemale, prostate, homemade
18:53 50%

Role-play, post-orgasm, female dominance

2 months ago

XXXVogue

handjob, shemale, train, prostate, orgasm, BDSM, compilation
15:57

DEVILS TGIRLS - Doctor Uses His Cock During This Trans Prostate Exam With Kalli Grace

2 months ago

AShemaleTube

big ass, big cock, doctor
16:00

DEVILS TGIRLS - Doctor Uses His Cock During This Trans Prostate Exam With Kalli Grace

2 months ago

AShemaleTube

shemale, prostate
16:00

Kalli Grace Endures Intense Prostate Check from Doctor with Massive Cock Bareback Pounding and Deep Anal Stretching

2 months ago

XXXDan

big cock, shemale, anal, prostate, doctor
16:00

The Devilish Doctor Pounds Kalli Graces Prostate Using His Dick During Hardcore Trans Prostate Exam

2 months ago

XXXDan

doctor, shemale
23:24 55%

Femboy Sorority - Ep 2 (Petite Femboy Prostate Orgasm)

3 months ago

AShemaleTube

anal, prostate, orgasm, sissy, femboy
17:44

ILL STOKE THAT trunk WHILE DEEP IN THEM prostate

3 months ago

ShemaleMovie

shemale, solo, prostate
17:59

Amateur Sissy female dom Compilation two

3 months ago

ShemaleMovie

handjob, strapon, prostate, massage, compilation, handjob compilation, sissy
27:43

Game Over if found out! calm Challenge: Anal Masturbation While Colleague is in the Next apartment

3 months ago

ShemaleMovie

game, crossdresser, prostate, femboy, sissy
16:27

Goth maid femboy dildo riding & fleshlight play - fishnets, prostate tease & messy cum

3 months ago

AShemaleTube

prostate, tease, maid, dildo, riding, goth, fleshlight
29:42

Masturbates off horny latte and fumbles his prostate with a huge dildo

3 months ago

VideoSection

handjob, huge dildo, prostate, massage, BBW, toys, vibrator
20:13

Steaming Sissygasm prostate Compilation

3 months ago

ShemaleMovie

compilation, cumshot compilation, crossdresser, amateur, prostate
16:43

Alone Again ShibbySays JOI

4 months ago

ShemaleTaxi

massage, JOI, solo, small cock, prostate
17:15

Goth femboy deep dildo riding & gape - dark-hued attire, multiple postures and no hands slide out

4 months ago

ShemaleMovie

huge dildo, prostate, massage, dildo, solo, riding, goth
38:49

You make me perceive magnificent

4 months ago

ShemaleTaxi

taxi, BBW, prostate
26:09

Amateur femboy, hard riding, mirror

4 months ago

XXXVogue

prostate, femboy, amateur, solo, riding, dildo
31:50

Compilation shemales cum while anal poke prostate

4 months ago

ShemaleTaxi

orgasm compilation, orgasm, anal orgasm, compilation, prostate, solo
18:53 56%

Female dominance IDEAS - TOP 10 bonus

4 months ago

HDSex

handjob, shemale, train, prostate, orgasm, BDSM, 18
16:28

Prostate orgasms cumpilation. Personalsin collection vol. 157

5 months ago

AShemaleTube

shemale, cumshot compilation, orgasm, prostate
26:09

Raw pussy and anal invasion ejaculations

5 months ago

ShemaleMovie

shemale, anal orgasm
17:18

Miyuki getting off

5 months ago

VideoSection

amateur, cumshot, solo, japanese, shemale, masturbation
24:16

REAL passionate hook-up: Lots of Oral, buttfuck, and an Intense Face Fucking

5 months ago

ShemaleMovie

beauty, prostate, massage, orgasm, cum in mouth, cum in ass
16:13

Student crossdresser desperately tries to cum having a chastity box (cum replay in slow-motion)

5 months ago

ShemaleMovie

orgasm, prostate, chastity
21:19

Transgirl Masterbates in Block Shootout

5 months ago

ShemaleMovie

masturbation, orgasm, prostate
16:16 67%

Fledgling, hd videos, hands free prostate orgasm

6 months ago

XXXVogue

anal, prostate, orgasm, riding, sissy, hands free
17:12

She-male pummel and piss

6 months ago

ShemaleMovie

dildo, shemale fucks guy, thai, prostate
16:58

Prostate_play - threesome with orgy girl and iron dildo - pt1

8 months ago

VideoSection

shemale, pantyhose, crossdresser, massage, dildo, prostate
15:37

TRANSFIXED - Sexy Trans Babe Kalli Grace Gets Fucked By Hot Doctor During Prostate Exam: Porn

8 months ago

JizzBunker

exam, shemale, anal, doctor, prostate
20:58

Naomi precum buttfuck pounding

8 months ago

ShemaleMovie

shemale, ebony, dildo, teen (18+), prostate, teen anal (18+)
41:12

2026 Prostate Orgasm Part 5

8 months ago

$$ FapHouse

prostate, orgasm, masturbation, ass, machine, sissy
18:22 88%

Femboy rides plaything dick & cums

8 months ago

ShemaleTaxi

small cock, anal, prostate, cumshot, riding, toys, taxi
29:34 29%

2026 Handsfree Orgasms, Prostate Cumshot Part 3

8 months ago

$$ FapHouse

prostate, orgasm, ass, machine, sissy, hands free
22:58

[Aneros] practice edible delectation with TEMPO and intense orgasms with HELIX

9 months ago

ShemaleTaxi

ladyboy, massage, prostate
15:34

Miyuki masturbation

9 months ago

ShemaleMovie

toys, shemale, japanese, cumshot, amateur, prostate
23:25

2026 Handsfree Cumshot Prostate Jet. Part 1

9 months ago

$$ FapHouse

amateur, shemale, hands free, prostate
16:29

YES! ravage This Locked Up great girl

9 months ago

ShemaleMovie

prostate, femboy, sissy, machine
15:36 40%

Sexy Trans Babe Gets Fucked By Hot Doctor During Prostate Exam - Kalli Grace

10 months ago

ShemaleZ

prostate, doctor, big tits, babe, exam
20:15

My first sissy climax with Lovense, jiggling like crazy and hands-free

10 months ago

XXXVogue

shemale, sissy, hands free, prostate, vibrator
22:22

Prostate Orgasms Galore - Billie Beaumont

10 months ago

$$ FapHouse

black, anal, prostate, couple, interracial, orgasm, tattoo
15:37

TRANSFIXED - Sexy Trans Babe Kalli Grace Gets Fucked By Hot Doctor During Prostate Exam

11 months ago

XXXDan

prostate, missionary
20:50

Japanese crossdresser Knhr Maki plays with a piston machine for some intense joyride and dry orgasm

11 months ago

XXXVogue

prostate, orgasm, japanese, dildo, machine
32:02

Erected tranny smmys0f1 doggy prostate cum September-30-2021 03-48-35: Porn

11 months ago

XXXDan

shemale, amateur, prostate, dogging
30:57

Training for early climax with ShibbySays JOI featuring pierced tgirl Itsol and anal toys

11 months ago

XXXVogue

anal, beauty, JOI, shemale, prostate, piercing
15:50

Prostate cum on my feet

11 months ago

XXXVogue

shemale, feet, solo, fisting, prostate
19:15

Lazzy luvs a quiet night with her bad dragon faux-cock

11 months ago

TrannyGem

anal, solo, chastity
20:03

BACKSIDE Woman Tiffany Ciskiss Extrem Rectal Emo Bi-Atch Ravages Caboose On Ample Ribbed Fuck Stick

11 months ago

TrannyGem

emo, prostate, dildo, sissy, gape, crossdresser
36:55

Shag my bootie and draining the prostate

11 months ago

ShemaleMovie

big ass, fisting, masturbation, prostate
25:08

Part 1: yam-sized ass-fuck getting off while moaning like an animal. -ToolChannel

11 months ago

HDSex

anal, orgasm, crossdresser, femboy, prostate
20:03 60%

Anal Orgasm by Fucking Machine! Giant fake penis easily Sparks Hands-Free jizm! -ToolChannel

11 months ago

ShemaleTaxi

prostate, orgasm, japanese, machine, penis, taxi, anal orgasm
31:37

Rectal w/ faux-cock untill i cum twice

11 months ago

ShemaleTaxi

shemale, anal, prostate
25:15

Japanese Femboy likes Huge horse Dildo! arms Free Cum in Post-Squirt Anal -ToolChannel

12 months ago

ShemaleMovie

creampie, femboy, dildo, japanese, huge dildo, prostate
15:10

Crossdresser with BIG BLACK COCK fuck stick

1 year ago

TrannyGem

amateur, crossdresser, prostate
21:06

Crossdresser in baby lady sploogs and urinates, then ejaculates repeatedly

1 year ago

HDSex

prostate, dildo, japanese
20:35

[Aneros Helix] asian Femboy Sissygasm: running in rivulets Precum rapture - ToolChannel

1 year ago

ShemaleTaxi

shemale, crossdresser, massage, prostate
27:49

My hottest Friends mother is a Futa?! - scene 1 [Anilingus, Anal Fingering, Blowjob, Tittyfuck JOI]

1 year ago

ShemaleTaxi

shemale, JOI, futanari, POV
24:44

Chinese Femboy bathing suit buttfuck Debut! Deep Male Moans in Climax from Anal Tease-ToolChannel

1 year ago

VideoSection

shemale, femboy, prostate, bath
18:27

Asian femboy Toolchannel takes a massive prostate massager for a ride after a dry orgasm

1 year ago

XXXVogue

shemale, crossdresser, prostate
27:59

My best Friends mother is a Futa - vignette 2 [Anal Exploration, Blowjob Training, Oral Creampie JOI]

1 year ago

ShemaleMovie

JOI, massage, futanari, dildo, prostate, train
35:04 75%

Wonderful tgirl Angel fake penis training

1 year ago

ShemaleMovie

small tits, anal, shemale, prostate, masturbation, train
21:08

Father Rearranges My prostate part two of 2 - FTM Trans Man

1 year ago

ShemaleTaxi

FTM, prostate, orgasm, creampie
1:53:43 25%

Compilation of deep ass-fuck penetrations ( sissy trap femboy anal riding )

1 year ago

ShemaleMovie

prostate, russian, dildo, compilation, riding, ass, toys
35:58

My naughty stepbrother pulverized me after college

1 year ago

ShemaleMovie

small cock, german, anal, prostate, orgasm, shemale and girl, heels
38:45

Lizzy yum - double penetration training, double penetration dildos, anal speculums, power tools.

1 year ago

ShemaleTaxi

train, machine, double penetration, prostate
36:09

Introducing U To Anal & Prostate Play

1 year ago

ShemaleZ

shemale, solo, prostate, lingerie
15:22

Flawless ten hook-up Therapist Fucks Her Clients Ass

1 year ago

ShemaleTaxi

feet, strapon, train, prostate, orgasm, facial, babe
15:33

Blonde femboy lingerie cum, forearms free lil cock squirt

1 year ago

ShemaleMovie

crossdresser, russian, dildo, sissy, femboy, prostate
22:41 83%

Smashed femboy in crimson stocking spreads her taut fuckhole and finishes off palms free-for-all

1 year ago

TrannyGem

cute, prostate, massage, teen anal (18+), riding, ass, hands free
26:38

Denial and demolish

1 year ago

ShemaleMovie

panties, sissy, prostate
24:45

Miyuki masturbation

1 year ago

ShemaleTaxi

solo, japanese, prostate, crossdresser
1:06:09 64%

Bang The spunk Out Of Him Trans Compilation 1-4

1 year ago

ShemaleTaxi

creampie, prostate, orgasm, creampie compilation, compilation, cumshot compilation, orgasm compilation
17:07 76%

Odor prostate wanking JOI 4K

1 year ago

HDSex

POV, solo, JOI, shemale, masturbation, prostate
4:22:41

Male Female In Oots-017 A Doujin Erotic Video Of A Dirty Cosplayer Who Loves Having His Prostate Stimulated By A Big Dick. Anal Masturbation, Deep Throat, Creampie, Swallowing, Female Orgasm, Male Orgasm, Ahegao, Kamarezu, Anal Sex, Pov, Doujin, Cosp

1 year ago

ShemaleZ

prostate, orgasm, swallow, erotic, cosplay
20:04 25%

Albedo helps give you a guts climax [Wholesome] Futa anime porn buttfuck JOI/ [Commission]

1 year ago

TrannyGem

femdom, prostate, instruction, jerking, anime, futanari, JOI
16:35

Ladyboy Crossdresser Mighty assfuck getting off jism many times

1 year ago

TrannyGem

prostate, dildo, femboy
18:12

Watch Me Sit on the Sex Machine and Squirt Prostate Fluid and Urine Multiple Times

1 year ago

$$ FapHouse

homemade, prostate, machine, mature
16:39

Femboys ass-fuck expansion teaching

1 year ago

ShemaleMovie

POV, femboy, prostate
16:00

Unboxing The Boogeyman dildo! (Sissygasms & Cumplay)

1 year ago

ShemaleMovie

prostate, orgasm, crossdresser, british, toys, sissy
24:19 56%

Step mummy drills son-in-law culo and train jizm while being drilled

1 year ago

TrannyGem

mom, femdom, strapon, huge dildo, prostate, orgasm, fisting
36:10

Fabulous arms free anal love

1 year ago

HDSex

big ass, masturbation, machine, toys, prostate
24:06

ыSissygasm from assfucking getting off in sissy breezy with closed joy button in chastity_sc.26

1 year ago

TrannyGem

cumshot, crossdresser, cum in ass, chastity, prostate
26:35

Denial and Wreck

1 year ago

TrannyGem

cute, prostate, panties, ass, small tits, chastity
25:15 33%

Man attempts to get delight while he is locked in a v-card box. Compilation

1 year ago

TrannyGem

handjob, mature, mature anal, prostate, hairy, milk, shy
20:43

Zero 2 lovingly binds up her good guy Bondage petplay hentai Oral & Anal JOI/ (Commission)

1 year ago

ShemaleMovie

big ass, bondage, crossdresser
26:06 80%

TRANSGIRL AND HER first DVP three-way!!

1 year ago

ShemaleMovie

prostate, threesome, massage, husband, socks, frottage
36:32 67%

Dame college girl pays an influential instructor for humiliation

1 year ago

ShemaleMovie

homemade, prostate, couple, massage, russian, BDSM, ass
51:25

Linzy19s Guide To purity

1 year ago

ShemaleMovie

domination, shemale, amateur, prostate
22:23

Cute pretty shemale mega-slut Sasha Earth in tights on bed fucking big butt hard sex toys dildo

1 year ago

ShemaleMovie

cute, huge dildo, prostate, prostitute, toys, tight, femboy
16:37

Femboys Assfuck expansion teaching

1 year ago

TrannyGem

anal, shemale, asian, fisting, prostate
20:04

ASS girl Tiffany Ciskiss Extrem buttfuck Punk Slut Fucks bum On Xxl Ribbed Dildo

1 year ago

ShemaleMovie

prostate, fisting, ass, toys, slut, gape
1:08:08

Ultimate Sissy palms Free ejaculation Compilation

1 year ago

ShemaleMovie

sissy, compilation, prostate
31:18

Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie

1 year ago

$$ FapHouse

stockings, french, prostate, massage, redhead, hardcore
17:44

ILL STOKE THAT prick WHILE DEEP IN THEM prostate

1 year ago

ShemaleTaxi

big cock, prostate
24:14 60%

REAL Spunky Intercourse: Lots of Blow-Job, Ass Fucking, and an Heavy Face Shagging

1 year ago

TrannyGem

cute, anal, prostate, massage, orgasm, ass, cum in mouth
23:10

Insert OK guts chip and jack your puffies. Erection and induce dry orgasm.

1 year ago

VideoSection

stockings, massage, japanese massage
26:05 82%

TRANNY AND HER FIRST-EVER DVP THREEWAY!!

1 year ago

TrannyGem

amateur, mom, shemale, prostate, threesome, massage, chubby
15:59

Best Pegging Compilation With Enchanting ending

1 year ago

ShemaleMovie

teen (18+), pegging, compilation, russian, prostate
26:07

Miyuki onanism

1 year ago

ShemaleMovie

asian, shemale, public, outdoor, stockings, prostate
20:20 40%

Japanese Crossdresser college girl gets pummeled by orgy machine

1 year ago

ShemaleMovie

anal, orgy, prostate, crossdresser, machine
20:03

Sasha Earth have fucky-fucky at home with fuck stick

1 year ago

ShemaleMovie

prostitute, crossdresser, homemade, amateur, BDSM, prostate
18:57 20%

Solo anal milking and masturbation with toys for a pretty transgender beauty

1 year ago

XXXVogue

beauty, ebony, feet, shemale, vibrator, prostate
36:09 71%

Jyosou Bishonen Prostate Lesson Prostate Lesson Mizuki Yukirin Crossdressing Beautiful Boy

1 year ago

XXXDan

amateur, crossdresser, japanese, beauty, shemale, prostate
49:30 57%

Transsexual SWINGERS three - gig 2

1 year ago

ShemaleMovie

skinny, shemale, lingerie, gangbang, prostate, swinger
18:29

See me drizzle and gape ravaging myself with this pearly bbc dildo

1 year ago

ShemaleMovie

pissing, prostate, dildo, british, babe, toys, BBC
15:04

Intense Prostate Milking Orgasm

1 year ago

JizzBunker

couple, shemale, milk, prostate
36:20 20%

Nice girl wants to be a strapon mistress and plumb a dude (spanking, first-ever time, comments at the end)

1 year ago

ShemaleMovie

femdom, teen (18+), strapon, prostate, couple, massage, russian
24:08

Sissygasm from anal onanism in sissy bi-atch with closed clittie in chastity_sc.26

1 year ago

ShemaleMovie

sissy, orgasm, cum in ass, prostate, crossdresser
20:05 20%

Девушка хорошо сосала, ебала страпоном, делала римминг. Много спермы, кончил 2 раза.

1 year ago

ShemaleMovie

public, teen (18+), strapon, prostate, russian, teen anal (18+), outdoor
15:34

ピストンマシンにバックから突かれてトコロテン前と後ろ同時に責められ連続射精｜女子校生制服女装オナニー男の娘｜偽娘慰菊射精 Femboy

1 year ago

ShemaleMovie

japanese, crossdresser, femboy, prostate, dildo
18:04

Japanese Crossdresser college girl gets drilled by sex machine

1 year ago

ShemaleMovie

prostate, orgasm, japanese, college, toys, machine, anal orgasm
20:53

Warm blond maid plays with and pounds mind-blowing ladyboys butt

1 year ago

TrannyGem

prostate, couple, MILF, orgasm, maid, lingerie, uniform
25:20 81%

OUR first-ever TRANS threesome video WITH AVERY ANGEL!!

1 year ago

ShemaleMovie

kissing, bisexual, prostate, threesome, massage, socks, frottage
22:58

[Aneros] practice sweet sensation with TEMPO and heavy orgasms with HELIX

1 year ago

ShemaleMovie

femboy, massage, prostate
18:22

Tear Up my taut Femboi Honeypot

1 year ago

TrannyGem

ass, dildo, femboy, prostate
24:35

Miyuki masturbation

1 year ago

xHamster

amateur, crossdresser, prostate, japanese

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