SHEMALE • PROSTATE 288 videos

Popular Latest Top rated

17:26 93%

Pretty Trans In Cock Chastity Cage Has An Anal Prostate Orgasm And Cum Explodes While Fucked Hard And Fast With A Huge Dildo Fuck Machine 18 Min

4 years ago

ShemaleZ

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34:39 91%

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

1 year ago

ShemaleZ

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16:30 90%

Prostate jerking...

5 years ago

ShemaleTaxi

latex, prostate, taxi
25:43 89%

Trans nubile got dual ejaculation with vibro

4 years ago

TrannyGem

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36:47 88%

Prostate Exam

2 years ago

AShemaleTube

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39:58 88%

Ts Dr. Chanel Noir: Home Prostate Exam

4 years ago

ShemaleZ

stockings, prostate, big tits, ass licking, exam
18:06 88%

Lovely and bad tranny

7 years ago

TrannyGem

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16:20 87%

Milk cow prostate cum

3 years ago

ShemaleZ

prostate, milk, selfsuck, crossdresser
21:07 86%

Meaty Lush rear entrance delicious woman-boy Jizzes while beaten By Montrous immense muscled lollipop

5 years ago

TrannyGem

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25:00 85%

Handsfree and prostate cumshots compilation

4 years ago

TrannyOne

prostate, cumshot compilation, hands free, compilation, amateur
16:24 85%

Uber-cute massive chubby donk she-male shoots a load while porked by a random XXL meaty man rod

4 years ago

TrannyGem

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26:05 84%

TRANSGENDER PRINCESS AND HER FIRST-EVER DVP THREE WAY!!

2 years ago

TrannyGem

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31:30 83%

Compilation shemales cum while anal fuck prostate

4 years ago

TrannyOne

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25:09 83%

Ladyboy Gold - Jasmine - Pink Prostate Play Bareback HD 720p

7 years ago

ShemaleZ

prostate, ladyboy
26:05 83%

TRANNY AND HER FIRST-EVER DVP THREEWAY!!

1 year ago

TrannyGem

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27:29 83%

SDHSERIES - Sissy Diaries Day ten

5 years ago

TrannyGem

prostate, orgasm, BDSM, orgasm compilation, small tits, JOI, sissy
36:48 82%

Prostate Epiphany With Erica Cherry And Whitney Wright

2 years ago

ShemaleZ

shemale, prostate
15:23 82%

Prostate Massage

6 years ago

ShemaleZ

prostate, massage, tattoo
20:22 81%

Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
34:36 81%

Prostate compilation

7 years ago

TXXX

prostate, compilation, toys, cumshot compilation
25:43 81%

Trans teenie got dual climax with electro-hitachi

4 years ago

TrannyGem

small cock, prostate, orgasm, double anal, electro, vibrator, double penetration
25:20 80%

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

1 year ago

ShemaleMovie

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18:22 80%

Femboy rides plaything dick & cums

4 months ago

ShemaleTaxi

small cock, anal, prostate, dildo, cumshot, riding, toys
16:20 80%

Prostate Milking...

4 years ago

TrannyOne

prostate, milk
17:16 80%

ANGEL’S CUMDUMP COMPILATION - BIG booty prostate wanking, BIG DICK FLESHLIGHT FUCKING & MORE

4 years ago

ShemaleMovie

prostate, BBW, dildo, compilation, machine, fleshlight
18:59 79%

Ladyboy in Manstick Box Heads Horny Wanting to Jizm // Climax Denial

4 years ago

TrannyGem

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17:07 79%

ANGEL’S CUMDUMP COMPILATION - GOOD-SIZED ASS GUTS DRAINING, THICK CHISEL FLESHLIGHT SHAGGING & MORE

4 years ago

TrannyGem

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20:08 78%

TranssexualAngel - Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
23:56 78%

Prostate Stimulation

4 years ago

Upornia

prostate, asian, ladyboy
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
36:18 77%

Introducing You to Anal & Prostate Play

5 years ago

BeMyHole

prostate, solo, jerking, cumshot
45:23 77%

Big breast shemale Dani Peterson Prostate Penetration

5 years ago

Analdin

stockings, prostate, brazil, big tits, ass licking, babe, erotic
25:11 76%

Sissygasm Compilation! Trans Konchaut Bez Ruk Podborka! Prostate Milking

4 years ago

Upornia

prostate, milk, compilation
21:10 75%

SDHSERIES - Sissy Diaries Day trio

4 years ago

TrannyGem

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17:07 75%

Odor prostate wanking JOI 4K

10 months ago

HDSex

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32:24 75%

Transgender Aubrey Kate Tears Up Puny Lilly Ford

7 years ago

TrannyGem

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26:06 75%

TRANSGIRL AND HER first DVP three-way!!

12 months ago

ShemaleMovie

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36:09 74%

Jyosou Bishonen Prostate Lesson Prostate Lesson Mizuki Yukirin Crossdressing Beautiful Boy

1 year ago

XXXDan

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35:04 73%

Wonderful tgirl Angel fake penis training

8 months ago

ShemaleMovie

small tits, anal, shemale, prostate, masturbation
24:29 72%

Handsfree And Prostate Cumshots Compilation

4 years ago

Upornia

prostate, compilation, cumshot compilation, hands free, solo
15:53 70%

Prostate Massage

8 years ago

ShemaleZ

prostate, massage
21:13 67%

PIG PET (2022, Horror film) - female dominance pegging with fisting,prostate jacking and fisting self jizz

2 years ago

ShemaleMovie

strapon, prostate, fisting, short hair, pegging, sissy, hardcore
18:53 67%

Female dominance IDEAS - TOP 10 bonus

2 weeks ago

HDSex

handjob, shemale, train, prostate, orgasm, BDSM, 18
36:32 67%

Dame college girl pays an influential instructor for humiliation

1 year ago

ShemaleMovie

amateur, homemade, prostate, couple, massage, russian, BDSM
26:41 67%

Prostate cum 23min12sec

6 years ago

ShemaleZ

prostate, cum in mouth
41:31 67%

Naughty Nurse Checks Patients Prostate Wt Her Massive Cock Indoors

2 years ago

BeMyHole

domination, shemale fucks guy, bareback, prostate, nurse
20:03 67%

Hot Sissygasm Prostate Compilation

4 years ago

AShemaleTube

prostate, compilation, cumshot compilation, crossdresser, toys
53:00 67%

Compilation legitimate - Smashing Machine - Guts Wanking - Anal Invasion Climax Sissygasm

6 years ago

TrannyGem

prostate, orgasm, machine, orgasm compilation, femboy
25:32 67%

Prostate orgasm

6 years ago

xHamster

prostate, orgasm
18:29 67%

Pequeño sploog con mi mini bad dragon

4 years ago

TrannyGem

huge dildo, squirt, prostate, orgasm, riding
45:23 64%

Dani Peterson Prostate Penetration

5 years ago

TXXX

prostate, stockings
1:06:09 63%

Bang The spunk Out Of Him Trans Compilation 1-4

10 months ago

ShemaleTaxi

creampie, prostate, orgasm, creampie compilation, compilation, big cock, cumshot compilation
17:36 61%

French Maid pulverizes ladyboy

6 years ago

HDSex

french, prostate, maid, crossdresser, sissy
16:42 60%

Aroma Prostate Milking Joi 4k

3 years ago

ShemaleZ

small cock, prostate, big cock, JOI, solo
24:19 60%

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

11 months ago

TrannyGem

mom, femdom, strapon, huge dildo, prostate, orgasm, fisting
24:14 60%

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

1 year ago

TrannyGem

amateur, cute, anal, prostate, massage, orgasm, ass
22:10 60%

All of my prostate milking

1 year ago

AShemaleTube

stockings, crossdresser, mature, prostate
19:04 59%

Young femboy caresses pipe and shoots a load from kneading the rectum ( sissy trap )

4 years ago

TrannyGem

prostate, massage, teen anal (18+), close up, sissy, femboy
19:04 58%

Young Femboy Gropes Cock and Ejaculates from Groping the Butthole ( Sissy Trap )

4 years ago

TrannyGem

cute, teen (18+), prostate, groped, massage, teen anal (18+), milk
51:23 57%

Linzy19's Guide To Chastity

3 years ago

xHamster

prostate, fetish, BDSM, domination, JOI, chastity
49:30 57%

Transsexual SWINGERS three - gig 2

1 year ago

ShemaleMovie

skinny, shemale, lingerie, gangbang, prostate, swinger
18:59 57%

T-Girl in Rod Cell Heads Wild Wanting to Jizm // Climax Denial

4 years ago

TrannyGem

prostate, massage, orgasm, chastity, milk
2:17:13 56%

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
31:39 53%

Compilation t-girls jizm while anal smash prostate

6 years ago

VideoSection

creampie, prostate, creampie compilation
16:16 50%

Fledgling, hd videos, hands free prostate orgasm

1 month ago

XXXVogue

shemale, anal, prostate, orgasm, crossdresser, riding, babe
18:49 50%

Miruku Aima Prostate Squirt Sex

9 years ago

xHamster

squirt, prostate, ladyboy
51:27 50%

SweetandHot buttfuck & (pre)cumshow

1 year ago

ShemaleMovie

shemale, femboy, orgasm, big tits, masturbation, prostate
25:15 50%

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

11 months ago

TrannyGem

handjob, mature, mature anal, prostate, hairy, milk, shy
27:30 50%

The coyote shocked JJ with more than 100 gears. The 7cm thick vibrating anal plug stirred the chrysanthemum point, and finally ejaculated twice continuously, and the thick semen kept flowing to the thighs.

4 years ago

TrannyGem

prostate, electro, vibrator, hands free
28:49 50%

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

2 years ago

TrannyGem

handjob, prostate, orgasm, japanese, toys, anal orgasm, hands free
57:47 45%

Slim femboy wax toyed, prostate massaged and weenie milked by female domination mistress got intense orgasm

2 years ago

ShemaleTaxi

handjob, femdom, massage, orgasm, bondage, BDSM, milk
34:36 43%

Prostate compilation

6 years ago

ShemaleZ

prostate, compilation, cumshot, cumshot compilation
31:30 40%

Compilation shemales cum while anal fuck prostate

8 years ago

TXXX

prostate, creampie compilation, compilation, cum while fucked, masturbation
16:05 40%

Unique Pegging Threesome Adventure with Trans Doll

2 years ago

TrannyOne

femdom, strapon, doll, prostate, threesome, pegging
29:34 29%

2026 Handsfree Orgasms, Prostate Cumshot Part 3

4 months ago

$$ FapHouse

prostate, orgasm, ass, machine, sissy, hands free
54:13 29%

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

1 year ago

XXXVogue

prostate, orgasm, femboy, shemale and girl, dildo
1:53:43 25%

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

8 months ago

ShemaleMovie

prostate, russian, dildo, compilation, riding, ass, toys
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
36:20 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
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
24:24 20%

How to make a good erotic video

2 years ago

xHamster

prostate, orgasm, mexican, erotic, anal orgasm, hands free
20:04 14%

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

10 months ago

TrannyGem

femdom, prostate, instruction, jerking, anime, futanari, JOI
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
17:15

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

1 week ago

ShemaleMovie

huge dildo, prostate, massage, dildo, solo, riding, babe
15:36

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

6 months ago

ShemaleZ

shemale, shemale fucks guy, doctor, babe, big tits, prostate
41:12

2026 Prostate Orgasm Part 5

4 months ago

$$ FapHouse

orgasm, solo, sissy, amateur, prostate, machine
16:43

Alone Again ShibbySays JOI

5 days ago

ShemaleTaxi

massage, JOI, solo, small cock
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, asian, gangbang, group, ass, orgy
20:03

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

7 months ago

ShemaleTaxi

prostate, orgasm, japanese, machine, penis, taxi, anal orgasm
20:21

Kinky Trans Nurse Shows Home Guts Examination!

4 years ago

TrannyGem

prostate, nurse, maid, blowjob
16:28

Prostate orgasms cumpilation. Personalsin collection vol. 157

1 month ago

AShemaleTube

shemale, cumshot compilation, orgasm, prostate
15:37

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

4 months ago

JizzBunker

exam, shemale, anal, doctor, prostate
22:22

Prostate Orgasms Galore - Billie Beaumont

6 months ago

$$ FapHouse

black, anal, prostate, couple, interracial, orgasm, tattoo
31:50

Compilation shemales cum while anal poke prostate

2 weeks ago

ShemaleTaxi

orgasm compilation, orgasm, anal orgasm, compilation, prostate, solo
24:16

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

1 month ago

ShemaleMovie

cum in mouth, shemale, cum in ass, orgasm, massage, beauty, prostate
31:18

Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie

1 year ago

$$ FapHouse

stockings, french, prostate, massage, redhead, hardcore
38:49

You make me perceive magnificent

1 week ago

ShemaleTaxi

taxi, BBW, prostate
20:58

Naomi precum buttfuck pounding

4 months ago

ShemaleMovie

shemale, ebony, dildo, teen (18+), prostate, teen anal (18+)
26:09

Amateur femboy, hard riding, mirror

2 weeks ago

XXXVogue

prostate, femboy, amateur, solo, riding, dildo
20:50

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

7 months ago

XXXVogue

prostate, orgasm, japanese, dildo, machine
36:10

Fabulous arms free anal love

11 months ago

HDSex

big ass, masturbation, machine, toys, prostate
16:23

Miyuki Masturbation 2

2 years ago

xHamster

latex, prostate, orgasm, japanese, masturbation, asian
15:04

Intense Prostate Milking Orgasm

1 year ago

JizzBunker

couple, shemale, milk, prostate
17:15

Trans Compilation: Prostate Orgasms Galore!

1 year ago

XXXVogue

chinese, orgasm compilation, cumshot compilation, compilation
1:57:08

Bokd-273 The Prostate Is Pierced And The Milk Leaks Tok

2 years ago

ShemaleZ

prostate, asian
19:06

Stunning Ts Vibrates Hur Prostate

3 years ago

Upornia

prostate, blonde, vibrator, solo
23:51

Milking my prostate and Getting punctured on an Indiana Jones artifact :three

3 years ago

ShemaleTaxi

prostate, milk, vibrator, taxi, femboy
16:00

Unboxing The Boogeyman dildo! (Sissygasms & Cumplay)

11 months ago

ShemaleMovie

prostate, orgasm, crossdresser, british, toys, sissy
1:08:08

Ultimate Sissy palms Free ejaculation Compilation

1 year ago

ShemaleMovie

sissy, compilation, prostate
23:25

2026 Handsfree Cumshot Prostate Jet. Part 1

5 months ago

$$ FapHouse

amateur, shemale, hands free, prostate
30:57

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

7 months ago

XXXVogue

anal, beauty, JOI, shemale, prostate, piercing
36:09

Introducing U To Anal & Prostate Play

9 months ago

ShemaleZ

shemale, solo, prostate, lingerie
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

10 months ago

ShemaleZ

POV, prostate, orgasm, swallow, erotic, cosplay
17:17

I wanna sense your beefstick way deep in the back of my prostate

2 years ago

TrannyGem

cute, pantyhose, black, creampie, prostate, sissy
20:22

Sexy Excited Trans Nurse Shows Home Prostate Exam!

3 years ago

TrannyOne

prostate, nurse, exam
17:05

Domina Squeezes wad out of his sack. Cock Milking Anal prostate massage

3 years ago

ShemaleTaxi

femdom, prostate, massage, milk, taxi
26:40

Nubile transsexual NURSES six - Scene 3

5 years ago

ShemaleTaxi

prostate, doctor, nurse, uniform, spanking, taxi
27:49

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

8 months ago

ShemaleTaxi

shemale, JOI, futanari, POV
35:58

My naughty stepbrother pulverized me after college

8 months ago

ShemaleMovie

small cock, german, anal, prostate, orgasm, shemale and girl, heels
22:41

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

9 months ago

TrannyGem

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

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