SHEMALE • PROSTATE 293 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

huge dildo, prostate, orgasm, dildo, redhead, 18, toys
34:39 92%

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

1 year ago

ShemaleZ

prostate, big tits, shemale and girl, blonde, cum in mouth, small tits, small cock
16:30 90%

Prostate jerking...

5 years ago

ShemaleTaxi

latex, prostate, taxi, jerking
25:43 89%

Trans nubile got dual ejaculation with vibro

4 years ago

TrannyGem

prostate, teen anal (18+), orgasm, latina, double anal, vibrator, double penetration
39:58 88%

Ts Dr. Chanel Noir: Home Prostate Exam

4 years ago

ShemaleZ

stockings, prostate, big tits, ass licking, exam
36:47 88%

Prostate Exam

2 years ago

AShemaleTube

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16:20 88%

Milk cow prostate cum

3 years ago

ShemaleZ

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18:06 88%

Lovely and bad tranny

7 years ago

TrannyGem

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25:00 86%

Handsfree and prostate cumshots compilation

4 years ago

TrannyOne

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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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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%

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

3 years ago

TrannyGem

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16:24 83%

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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27:29 83%

SDHSERIES - Sissy Diaries Day ten

5 years ago

TrannyGem

prostate, orgasm, BDSM, orgasm compilation, small tits, JOI, sissy
26:05 83%

TRANNY AND HER FIRST-EVER DVP THREEWAY!!

1 year ago

TrannyGem

amateur, mom, shemale, prostate, threesome, massage, chubby
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
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
18:59 80%

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

4 years ago

TrannyGem

prostate, massage, fetish, orgasm, milk, babe, chastity
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

5 months ago

ShemaleTaxi

small cock, anal, prostate, cumshot, riding, toys, taxi
1:57:08 80%

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

2 years ago

ShemaleZ

prostate, asian
16:20 80%

Prostate Milking...

4 years ago

TrannyOne

prostate, milk
17:07 80%

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

4 years ago

TrannyGem

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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
34:36 79%

Prostate compilation

7 years ago

TXXX

prostate, compilation, toys, cumshot compilation
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 76%

SDHSERIES - Sissy Diaries Day trio

4 years ago

TrannyGem

prostate, orgasm, dildo, BDSM, compilation, orgasm compilation, JOI
17:07 75%

Odor prostate wanking JOI 4K

11 months ago

HDSex

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26:06 75%

TRANSGIRL AND HER first DVP three-way!!

1 year ago

ShemaleMovie

prostate, threesome, massage, husband, socks, frottage
32:24 74%

Transgender Aubrey Kate Tears Up Puny Lilly Ford

7 years ago

TrannyGem

handjob, prostate, massage, nipples, masturbation, 69
36:09 74%

Jyosou Bishonen Prostate Lesson Prostate Lesson Mizuki Yukirin Crossdressing Beautiful Boy

1 year ago

XXXDan

amateur, crossdresser, japanese, beauty, shemale, prostate
24:29 73%

Handsfree And Prostate Cumshots Compilation

4 years ago

Upornia

prostate, compilation, cumshot compilation, hands free, solo
35:04 73%

Wonderful tgirl Angel fake penis training

9 months ago

ShemaleMovie

small tits, anal, shemale, prostate, masturbation
15:53 70%

Prostate Massage

8 years ago

ShemaleZ

prostate, massage
21:13 68%

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

1 month ago

HDSex

handjob, shemale, train, prostate, orgasm, BDSM, 18
26:41 67%

Prostate cum 23min12sec

6 years ago

ShemaleZ

prostate, cum in mouth
20:03 67%

Hot Sissygasm Prostate Compilation

4 years ago

AShemaleTube

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25:32 67%

Prostate orgasm

6 years ago

xHamster

prostate, orgasm
36:32 67%

Dame college girl pays an influential instructor for humiliation

1 year ago

ShemaleMovie

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41:31 67%

Naughty Nurse Checks Patients Prostate Wt Her Massive Cock Indoors

3 years ago

BeMyHole

domination, shemale fucks guy, bareback, prostate, nurse
18:29 67%

Pequeño sploog con mi mini bad dragon

4 years ago

TrannyGem

huge dildo, squirt, prostate, orgasm, riding
53:00 67%

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

6 years ago

TrannyGem

prostate, orgasm, machine, orgasm compilation, femboy
1:06:09 63%

Bang The spunk Out Of Him Trans Compilation 1-4

11 months ago

ShemaleTaxi

creampie, prostate, orgasm, creampie compilation, compilation, cumshot compilation, orgasm compilation
45:23 63%

Dani Peterson Prostate Penetration

5 years ago

TXXX

prostate, stockings
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
24:14 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
22:10 60%

All of my prostate milking

1 year ago

AShemaleTube

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

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
19:04 59%

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

5 years ago

TrannyGem

prostate, massage, teen anal (18+), crossdresser, close up, sissy, femboy
49:30 57%

Transsexual SWINGERS three - gig 2

1 year ago

ShemaleMovie

skinny, shemale, lingerie, gangbang, prostate, swinger
51:23 57%

Linzy19's Guide To Chastity

3 years ago

xHamster

prostate, fetish, BDSM, domination, JOI, chastity
18:59 57%

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

4 years ago

TrannyGem

prostate, massage, orgasm, chastity, milk
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
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

3 months ago

XXXVogue

anal, prostate, orgasm, riding, babe, sissy, hands free
18:49 50%

Miruku Aima Prostate Squirt Sex

9 years ago

xHamster

squirt, prostate, ladyboy
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
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
51:27 50%

SweetandHot buttfuck & (pre)cumshow

1 year ago

ShemaleMovie

shemale, femboy, orgasm, big tits, masturbation, prostate
31:30 45%

Compilation shemales cum while anal fuck prostate

8 years ago

TXXX

prostate, creampie compilation, compilation, cum while fucked, masturbation
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
25:15 43%

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
34:36 43%

Prostate compilation

7 years ago

ShemaleZ

prostate, compilation, cumshot, cumshot compilation
15:36 40%

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

7 months ago

ShemaleZ

prostate, doctor, big tits, babe
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

6 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 )

10 months ago

ShemaleMovie

prostate, russian, dildo, compilation, riding, ass, toys
19:59 20%

Wholesome self facial cumshot CEI with futa orc (Expressed reupload+ feral) Chastity feminization Assfuck JOI/

3 years ago

TrannyGem

femdom, creampie, prostate, instruction, facial, shemale and girl, futanari
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]

12 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
41:12

2026 Prostate Orgasm Part 5

5 months ago

$$ FapHouse

orgasm, solo, sissy, amateur, prostate, machine
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
20:21

Kinky Trans Nurse Shows Home Guts Examination!

4 years ago

TrannyGem

prostate, nurse, maid, blowjob
16:27

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

1 month ago

AShemaleTube

prostate, tease, maid, dildo, riding, goth, fleshlight
17:59

Amateur Sissy female dom Compilation two

3 weeks ago

ShemaleMovie

handjob, strapon, prostate, massage, compilation, handjob compilation, sissy
20:03

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

9 months ago

ShemaleTaxi

prostate, orgasm, japanese, machine, penis, taxi, anal orgasm
20:13

Steaming Sissygasm prostate Compilation

1 month ago

ShemaleMovie

compilation, cumshot compilation, crossdresser, amateur, prostate
15:37

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

5 months ago

JizzBunker

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

Prostate Orgasms Galore - Billie Beaumont

8 months ago

$$ FapHouse

black, anal, prostate, couple, interracial, orgasm, tattoo
22:37

Adorable trap femboy climaxes forearms free-for-all from petting mighty wand ( sissy instructing )

4 years ago

TrannyGem

prostate, instruction, massage, russian, orgasm, milk, close up
16:28

Prostate orgasms cumpilation. Personalsin collection vol. 157

2 months ago

AShemaleTube

shemale, cumshot compilation, orgasm, prostate
15:22

Flawless ten hook-up Therapist Fucks Her Clients Ass

10 months ago

ShemaleTaxi

feet, strapon, train, prostate, orgasm, facial, babe
29:42

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

1 month ago

VideoSection

handjob, huge dildo, prostate, massage, BBW, jerking, toys
31:50

Compilation shemales cum while anal poke prostate

1 month ago

ShemaleTaxi

orgasm compilation, orgasm, anal orgasm, compilation, prostate, solo
17:15

Trans Compilation: Prostate Orgasms Galore!

1 year ago

XXXVogue

chinese, orgasm compilation, cumshot compilation, compilation
16:43

Alone Again ShibbySays JOI

1 month 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

1 month ago

ShemaleMovie

huge dildo, prostate, massage, dildo, solo, riding, babe
20:50

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

8 months ago

XXXVogue

prostate, orgasm, japanese, dildo, machine
21:20

Miyuki masturbation

1 year ago

xHamster

prostate, orgasm, japanese, big tits, cumshot, vibrator
21:53

[男の娘 - FULL] アネロスが動きまくってメスイキ！！！(アネロスヒリックス)

2 years ago

TrannyGem

orgasm, anal orgasm, japanese, prostate, japanese massage, massage
31:18

Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie

1 year ago

$$ FapHouse

stockings, french, prostate, massage, redhead, hardcore
20:22

Chanel Noir In Horny Trans Nurse Demonstrates Home Prostate Exam!

5 years ago

ShemaleZ

prostate, nurse, big tits, ass licking, exam, big cock
27:43

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

3 weeks ago

ShemaleMovie

game, crossdresser, prostate, femboy, sissy
20:58

Naomi precum buttfuck pounding

5 months ago

ShemaleMovie

shemale, ebony, dildo, teen (18+), prostate, teen anal (18+)
27:59

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

9 months ago

ShemaleMovie

JOI, massage, futanari, dildo, prostate
35:58

My naughty stepbrother pulverized me after college

10 months ago

ShemaleMovie

small cock, german, anal, prostate, orgasm, shemale and girl, heels
26:35

Denial and Wreck

1 year ago

TrannyGem

cute, POV, prostate, panties, ass, small tits, chastity
15:07

Backside Boned Femboy Shoots A Load Super-Steamy Arms Free-For-All (Opened Up Crevasse Likes)

4 years ago

TrannyGem

train, prostate, hands free, femboy, crossdresser
15:02

Trap Shoots A Load while Railing a Monster Fake Penis

5 years ago

TrannyGem

huge dildo, prostate, monster, penis, cum while fucked
23:51

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

3 years ago

ShemaleTaxi

prostate, milk, vibrator, taxi, femboy, crossdresser
26:40

Nubile transsexual NURSES six - Scene 3

5 years ago

ShemaleTaxi

prostate, doctor, nurse, uniform, spanking, taxi
16:58

Prostate_play - threesome with orgy girl and iron dildo - pt1

5 months ago

VideoSection

shemale, pantyhose, crossdresser, massage, dildo, 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
18:04

Japanese Crossdresser college girl gets drilled by sex machine

1 year ago

ShemaleMovie

prostate, orgasm, japanese, dildo, college, toys, machine

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