SHEMALE • PROSTATE 276 videos

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17:12

She-male pummel and piss

1 week ago

ShemaleMovie

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

Prostate_play - threesome with orgy girl and iron dildo - pt1

1 month 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

2 months ago

JizzBunker

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

Naomi precum buttfuck pounding

2 months ago

ShemaleMovie

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

2026 Prostate Orgasm Part 5

2 months ago

$$ FapHouse

orgasm, solo, sissy, amateur, prostate
18:22

Femboy rides plaything dick & cums

2 months ago

ShemaleTaxi

small cock, anal, prostate, dildo, cumshot, riding, toys
29:34 33%

2026 Handsfree Orgasms, Prostate Cumshot Part 3

2 months ago

$$ FapHouse

prostate, asian, orgasm, ass, machine, sissy, hands free
15:34

Miyuki masturbation

3 months ago

ShemaleMovie

toys, shemale, japanese, cumshot, amateur, prostate
22:58

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

3 months ago

ShemaleTaxi

ladyboy, massage, prostate
23:25

2026 Handsfree Cumshot Prostate Jet. Part 1

3 months ago

$$ FapHouse

amateur, shemale, hands free, prostate
16:29

YES! ravage This Locked Up great girl

3 months ago

ShemaleMovie

prostate, femboy, sissy, machine
15:36

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

4 months ago

ShemaleZ

shemale, shemale fucks guy, doctor, babe, big tits, prostate
20:15

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

4 months ago

XXXVogue

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

Prostate Orgasms Galore - Billie Beaumont

4 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

4 months ago

XXXDan

prostate, missionary
20:50

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

5 months ago

XXXVogue

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

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

5 months ago

XXXDan

shemale, amateur, prostate
30:57

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

5 months ago

XXXVogue

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

Prostate cum on my feet

5 months ago

XXXVogue

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

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

5 months ago

TrannyGem

anal, solo, chastity
20:03

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

5 months ago

TrannyGem

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

Shag my bootie and draining the prostate

5 months ago

ShemaleMovie

big ass, fisting, masturbation
25:08

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

5 months ago

HDSex

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

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

5 months ago

ShemaleTaxi

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

Rectal w/ faux-cock untill i cum twice

5 months ago

ShemaleTaxi

shemale, anal, prostate
25:15

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

5 months ago

ShemaleMovie

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

Crossdresser with BIG BLACK COCK fuck stick

6 months ago

TrannyGem

amateur, crossdresser, prostate
21:06

Crossdresser in baby lady sploogs and urinates, then ejaculates repeatedly

6 months ago

HDSex

prostate, dildo, japanese
20:35

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

6 months ago

ShemaleTaxi

shemale, crossdresser, massage
27:49

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

6 months ago

ShemaleTaxi

shemale, JOI, futanari, POV
24:44

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

6 months ago

VideoSection

shemale, femboy, prostate, bath
18:27

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

6 months ago

XXXVogue

shemale, crossdresser, prostate
27:59

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

6 months ago

ShemaleMovie

JOI, massage, futanari, dildo
35:04 73%

Wonderful tgirl Angel fake penis training

6 months ago

ShemaleMovie

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

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

6 months ago

ShemaleTaxi

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

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

6 months ago

ShemaleMovie

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

My naughty stepbrother pulverized me after college

6 months ago

ShemaleMovie

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38:45

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

6 months ago

ShemaleTaxi

train, machine, double penetration
36:09

Introducing U To Anal & Prostate Play

6 months ago

ShemaleZ

shemale, solo, prostate, lingerie
15:22

Flawless ten hook-up Therapist Fucks Her Clients Ass

7 months ago

ShemaleTaxi

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

Blonde femboy lingerie cum, forearms free lil cock squirt

7 months ago

ShemaleMovie

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

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

7 months ago

TrannyGem

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

Denial and demolish

7 months ago

ShemaleMovie

panties, sissy, prostate
24:45

Miyuki masturbation

7 months ago

ShemaleTaxi

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

Bang The spunk Out Of Him Trans Compilation 1-4

8 months ago

ShemaleTaxi

creampie, prostate, orgasm, creampie compilation, compilation, big cock, cumshot compilation
17:07 74%

Odor prostate wanking JOI 4K

8 months ago

HDSex

POV, solo, JOI, shemale, masturbation, prostate
20:04 14%

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

8 months ago

TrannyGem

femdom, prostate, instruction, jerking, anime, futanari, JOI
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

8 months ago

ShemaleZ

POV, prostate, asian, orgasm, swallow, erotic, cosplay
16:35

Ladyboy Crossdresser Mighty assfuck getting off jism many times

8 months ago

TrannyGem

sissy, crossdresser, shemale, anal, dildo, femboy, prostate
18:12

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

8 months ago

$$ FapHouse

homemade, prostate, machine, mature
16:39

Femboys ass-fuck expansion teaching

8 months ago

ShemaleMovie

POV, femboy, prostate
16:00

Unboxing The Boogeyman dildo! (Sissygasms & Cumplay)

8 months ago

ShemaleMovie

prostate, orgasm, crossdresser, british, toys, sissy
24:19 64%

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

8 months ago

TrannyGem

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

Fabulous arms free anal love

9 months 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

9 months ago

TrannyGem

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

Denial and Wreck

9 months ago

TrannyGem

cute, POV, prostate, panties, ass, small tits, chastity
25:15 50%

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

9 months 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)

9 months ago

ShemaleMovie

big ass, bondage, crossdresser
26:06 79%

TRANSGIRL AND HER first DVP three-way!!

9 months ago

ShemaleMovie

prostate, threesome, massage, husband, socks, frottage
36:32 70%

Dame college girl pays an influential instructor for humiliation

10 months ago

ShemaleMovie

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

Linzy19s Guide To purity

10 months 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

10 months ago

ShemaleMovie

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

Femboys Assfuck expansion teaching

10 months ago

TrannyGem

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

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

10 months ago

ShemaleMovie

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

Ultimate Sissy palms Free ejaculation Compilation

10 months ago

ShemaleMovie

sissy, compilation, prostate
31:18

Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie

10 months ago

$$ FapHouse

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

ILL STOKE THAT prick WHILE DEEP IN THEM prostate

10 months ago

ShemaleTaxi

big cock, prostate
24:14 60%

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

10 months ago

TrannyGem

amateur, cute, anal, prostate, massage, orgasm, babe
23:10

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

11 months ago

VideoSection

stockings, massage, japanese massage
26:05 84%

TRANNY AND HER FIRST-EVER DVP THREEWAY!!

11 months ago

TrannyGem

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

Best Pegging Compilation With Enchanting ending

11 months ago

ShemaleMovie

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

Miyuki onanism

11 months ago

ShemaleMovie

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

Japanese Crossdresser college girl gets pummeled by orgy machine

11 months ago

ShemaleMovie

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

Sasha Earth have fucky-fucky at home with fuck stick

11 months ago

ShemaleMovie

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

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

12 months ago

XXXVogue

beauty, ebony, feet, shemale, vibrator, prostate
36:09 73%

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, POV, prostate, dildo, british, babe, toys
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
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
15:04

Intense Prostate Milking Orgasm

1 year ago

JizzBunker

couple, shemale
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, dildo, college, toys, machine
20:53

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

1 year ago

TrannyGem

prostate, couple, MILF, orgasm, maid, dildo, lingerie
25:20 83%

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

1 year ago

ShemaleMovie

kissing, shemale, bisexual, prostate, threesome, massage, socks
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
24:35

Miyuki masturbation

1 year ago

xHamster

amateur, crossdresser, prostate, japanese
19:15 77%

Hands Free Cum with huge Mr Hankeys Cody Cachet dildo

1 year ago

xHamster

huge dildo, anal, prostate, dildo, lingerie, riding, ass
40:25

OfficeSuit, Femboy & AnalMasturbation: The Ultimate masterpiece!

1 year ago

ShemaleMovie

shemale, crossdresser, prostate
20:31

TranssexualAngel - crazy Trans Nurse displays Home prostate Exam!

1 year ago

ShemaleMovie

shemale, big tits, big ass, nurse, exam, prostate
21:20

Miyuki masturbation

1 year ago

xHamster

prostate, orgasm, japanese, big tits, cumshot, vibrator
31:50

Compilation of ladyboys cumming while getting their assholes pounded for prostate pleasure

1 year ago

XXXVogue

asshole, compilation, orgasm compilation, orgasm, prostate
18:22

Femboy fucks toy cock and cums

1 year ago

XXXVogue

dildo, femboy, homemade, cumshot, masturbation
17:15

Trans Compilation: Prostate Orgasms Galore!

1 year ago

XXXVogue

chinese, orgasm compilation, cumshot compilation, compilation
54:13 29%

Naomi, the sexy trans girl, indulges in passionate anal pounding

1 year ago

XXXVogue

prostate, orgasm, femboy, shemale and girl, dildo
23:41

Jewel gets drained and sissygasm multiple times

1 year ago

XXXVogue

homemade
2:00:08

Ichinose Ramu - Waaa-454 Penicli Huge Cock Big Climax! Infinite Piston Of The Prostate, Reason Is Blown Away, Extraordinary Muscle Orgy, Miracle Gal Shemale Is Made To Cum Hard Anal Fuck Ramu Ichinose

1 year ago

ShemaleZ

muscle, prostate, gangbang, group, ass, orgy
22:29

Edging CEI

1 year ago

TrannyGem

amateur, shemale, prostate, milk
22:10 60%

All of my prostate milking

1 year ago

AShemaleTube

stockings, crossdresser, mature, prostate
21:25

Femboy Room31 anal invasion edging

1 year ago

ShemaleMovie

small tits, femboy, masturbation, prostate
51:28

MangoK buttfuck cum from monster dildo

1 year ago

ShemaleMovie

femboy, small cock, monster, prostate
23:18

Slutty gaping femboy and prostate orgasm at the end

1 year ago

XXXDan

prostate, cumshot, femboy, anal, amateur
15:12

4.4 trans prostate orgasm

1 year ago

JizzBunker

orgasm
17:05

Miyuki masturbation

1 year ago

xHamster

latex, prostate, orgasm, japanese, big tits, toys, vibrator
51:27 50%

SweetandHot buttfuck & (pre)cumshow

1 year ago

ShemaleMovie

shemale, femboy, orgasm, big tits, masturbation, prostate
51:30

MangoK jizzes handsfree ass fucking then wanks & cums again

1 year ago

VideoSection

small cock, big tits, hands free
34:39 90%

Sweetie Trans Fucked Like A Wild Girl!!! And Having Prostate Analgasms

1 year ago

ShemaleZ

prostate, big tits, blonde, cum in mouth, small tits
28:30 10%

Can You Treat Your Keyholders Gifts? - Ass-Fuck Have Fun, Feminization, Purity Praise RP

1 year ago

TrannyGem

mom, femdom, prostate, dildo, 18, cartoon, chastity
17:18

No hands cum Holly Hunt fucks her ass with immense faux-cocks until she has a prostate orgasm

1 year ago

ShemaleTaxi

huge dildo, prostate, orgasm, dildo, gape, hands free
2:17:13 50%

Bokd-291 Prostate Is Thrusted Violently And Milk Leaks Out In A Squirting Sex Renka Yuzuki

1 year ago

ShemaleZ

shemale, asian, prostate, stockings, squirt, lingerie
17:17

Hands free cum Holly Hunt fucks her ass with massive dildos until she has a prostate orgasm

1 year ago

xHamster

amateur, prostate, cumshot, dildo, hands free
18:36

Miyuki masturbation

1 year ago

xHamster

masturbation, lingerie, big tits, japanese, prostate
17:20

Sir Drained Me Like A Cow After A Great Guts Mashing

1 year ago

TrannyGem

prostate, chubby, orgasm, dildo, dogging, femboy
17:19

Master Milked Me Like A Cow After A Good Prostate Mashing

1 year ago

PornHub

prostate, asian, amateur, shemale
22:59

005 - Red Miniskirt Aneros Prostate Play - Part 2

1 year ago

JizzBunker

prostate
19:22

Prostate jerking Dec-17-2014

1 year ago

ShemaleMovie

crossdresser
20:22

Miyuki masturbation

1 year ago

xHamster

asian, hands free
28:49 50%

[Japanese Femboy - FULL] Stiff Poke delicate Guts that Palms Free-For-All Spunk to Man Juice Pool!

1 year ago

TrannyGem

handjob, prostate, orgasm, japanese, toys, anal orgasm, hands free

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