SHEMALE • PROSTATE 271 videos

Popular Latest Top rated

45:23 77%

Big breast shemale Dani Peterson Prostate Penetration

5 years ago

Analdin

stockings, prostate, brazil, big tits, ass licking, babe, erotic
20:22 81%

Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
34:36 74%

Prostate compilation

6 years ago

TXXX

prostate, compilation, toys, cumshot compilation
26:05 84%

TRANNY AND HER FIRST-EVER DVP THREEWAY!!

8 months ago

TrannyGem

amateur, mom, shemale, prostate, threesome, massage, chubby
17:07 80%

Odor prostate wanking JOI 4K

6 months ago

HDSex

POV, solo, JOI, shemale, masturbation, prostate
25:11 75%

Sissygasm Compilation! Trans Konchaut Bez Ruk Podborka! Prostate Milking

3 years ago

Upornia

prostate, milk, compilation
39:58 89%

Ts Dr. Chanel Noir: Home Prostate Exam

4 years ago

ShemaleZ

stockings, prostate, big tits, ass licking, exam
15:36

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

1 month ago

ShemaleZ

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26:05 84%

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

2 years ago

TrannyGem

mom, shemale, prostate, massage, chubby, wife, MILF
36:09 71%

Jyosou Bishonen Prostate Lesson Prostate Lesson Mizuki Yukirin Crossdressing Beautiful Boy

9 months ago

XXXDan

amateur, crossdresser, japanese, beauty, shemale, prostate
45:23 61%

Dani Peterson Prostate Penetration

4 years ago

TXXX

prostate, stockings
29:34

2026 Handsfree Orgasms, Prostate Cumshot Part 3

5 days ago

$$ FapHouse

anal, sissy, amateur, orgasm, hands free, cumshot, solo
21:13 66%

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

2 years ago

ShemaleMovie

shemale, strapon, prostate, fisting, short hair, pegging, sissy
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
18:49 50%

Miruku Aima Prostate Squirt Sex

9 years ago

xHamster

squirt, prostate, ladyboy
1:06:09 61%

Bang The spunk Out Of Him Trans Compilation 1-4

6 months ago

ShemaleTaxi

creampie, prostate, orgasm, creampie compilation, compilation, big cock, cumshot compilation
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
17:36 56%

French Maid pulverizes ladyboy

6 years ago

HDSex

french, prostate, maid, crossdresser, sissy
20:08 78%

TranssexualAngel - Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
22:22

Prostate Orgasms Galore - Billie Beaumont

2 months ago

$$ FapHouse

black, anal, prostate, couple, interracial, orgasm, tattoo
34:39 89%

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

1 year ago

ShemaleZ

stockings, prostate, big tits, blonde, cum in mouth, small tits
36:18 70%

Introducing You to Anal & Prostate Play

5 years ago

BeMyHole

prostate, solo, jerking, cumshot
16:42 60%

Aroma Prostate Milking Joi 4k

2 years ago

ShemaleZ

small cock, prostate, big cock, JOI, solo
35:04 75%

Wonderful tgirl Angel fake penis training

3 months ago

ShemaleMovie

small tits, anal, shemale, prostate, masturbation
26:06 75%

TRANSGIRL AND HER first DVP three-way!!

7 months ago

ShemaleMovie

prostate, threesome, massage, husband, socks, frottage
24:29 70%

Handsfree And Prostate Cumshots Compilation

4 years ago

Upornia

prostate, compilation, cumshot compilation, hands free, solo
49:30 57%

Transsexual SWINGERS three - gig 2

10 months ago

ShemaleMovie

skinny, shemale, lingerie, gangbang, prostate, swinger
26:41 67%

Prostate cum 23min12sec

6 years ago

ShemaleZ

prostate, cum in mouth
36:03 43%

New Tgirl Series Part I. Beautiful Trans Maria

2 years ago

ShemaleZ

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51:27 50%

SweetandHot buttfuck & (pre)cumshow

1 year ago

ShemaleMovie

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16:24 88%

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

4 years ago

TrannyGem

cute, anal, prostate, chubby, orgasm, anal orgasm, cum while fucked
20:22

Sexy Excited Trans Nurse Shows Home Prostate Exam!

2 years ago

TrannyOne

prostate, nurse, exam
20:03 67%

Hot Sissygasm Prostate Compilation

4 years ago

AShemaleTube

prostate, compilation, cumshot compilation, crossdresser, toys
19:15 73%

Hands Free Cum with huge Mr Hankeys Cody Cachet dildo

11 months ago

xHamster

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25:00 82%

Handsfree and prostate cumshots compilation

4 years ago

TrannyOne

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34:36 43%

Prostate compilation

6 years ago

ShemaleZ

prostate, compilation, cumshot, cumshot compilation
31:30 91%

Compilation shemales cum while anal fuck prostate

3 years ago

TrannyOne

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32:24 74%

Transgender Aubrey Kate Tears Up Puny Lilly Ford

6 years ago

TrannyGem

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36:32 70%

Dame college girl pays an influential instructor for humiliation

7 months ago

ShemaleMovie

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1:08:08

Ultimate Sissy palms Free ejaculation Compilation

8 months ago

ShemaleMovie

sissy, compilation, prostate
1:57:08

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

2 years ago

ShemaleZ

prostate, asian
25:20 81%

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

10 months ago

ShemaleMovie

kissing, shemale, bisexual, prostate, threesome, massage, socks
18:06 88%

Lovely and bad tranny

6 years ago

TrannyGem

prostate, orgasm, redhead, masturbation, reality, vibrator, hands free
19:06

Stunning Ts Vibrates Hur Prostate

3 years ago

Upornia

prostate, blonde, vibrator, solo
16:29

YES! ravage This Locked Up great girl

1 month ago

ShemaleMovie

prostate, femboy, sissy, machine
25:32 67%

Prostate orgasm

5 years ago

xHamster

prostate, orgasm
31:18

Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie

8 months ago

$$ FapHouse

amateur, stockings, french, prostate, massage, redhead, hardcore
49:39

Ts SWINGERS trio - sequence 2

4 years ago

ShemaleTaxi

swinger, prostate, gangbang, skinny
22:51

TRANNY extreme 4 - gig trio

4 years ago

ShemaleTaxi

prostate, ass licking, deepthroat, taxi
31:30 40%

Compilation shemales cum while anal fuck prostate

8 years ago

TXXX

prostate, creampie compilation, compilation, cum while fucked, masturbation
30:57

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

2 months ago

XXXVogue

anal, beauty, JOI, shemale, prostate, piercing
28:49 57%

[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
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)

1 year ago

TrannyGem

orgasm, anal orgasm, japanese, prostate, japanese massage
20:21

Kinky Trans Nurse Shows Home Guts Examination!

4 years ago

TrannyGem

prostate, nurse, maid, blowjob
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
36:48 82%

Prostate Epiphany With Erica Cherry And Whitney Wright

2 years ago

ShemaleZ

shemale, prostate
34:23

TSCHX Cumshot 30:31 & Prostate Cum 32:15

8 years ago

xHamster

prostate
25:09 78%

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

7 years ago

ShemaleZ

prostate, ladyboy
41:31 67%

Naughty Nurse Checks Patients Prostate Wt Her Massive Cock Indoors

2 years ago

BeMyHole

domination, shemale fucks guy, bareback, prostate, nurse
17:17

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

1 year ago

TrannyGem

cute, pantyhose, black, creampie, prostate, sissy
22:10

All of my prostate milking

1 year ago

AShemaleTube

stockings, crossdresser, mature, prostate
17:05

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

3 years ago

ShemaleTaxi

femdom, prostate, massage, milk, taxi
36:10

Fabulous arms free anal love

6 months ago

HDSex

big ass, masturbation, machine, toys, prostate
36:47 88%

Prostate Exam

2 years ago

AShemaleTube

blowjob, prostate, shemale and girl, cumshot, masturbation, exam
20:15

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

1 month ago

XXXVogue

shemale, sissy, hands free, prostate, vibrator
16:05 40%

Unique Pegging Threesome Adventure with Trans Doll

1 year ago

TrannyOne

femdom, strapon, doll, prostate, threesome, pegging
24:14 60%

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

8 months ago

TrannyGem

amateur, cute, anal, prostate, massage, orgasm, babe
23:56 78%

Prostate Stimulation

3 years ago

Upornia

prostate, asian
23:42

Milking my prostate and Getting impaled on an Indiana Jones artifact :3

6 years ago

ShemaleZ

prostate, milk
20:50

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

2 months ago

XXXVogue

prostate, orgasm, japanese, dildo, machine
18:11

Asian Crossdresser student gets humped by sex machine

2 years ago

ShemaleTaxi

student, japanese, dildo, prostate
20:22

Chanel Noir In Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

ShemaleZ

prostate, nurse, big tits, ass licking, exam, big cock
27:29 78%

SDHSERIES - Sissy Diaries Day ten

4 years ago

TrannyGem

prostate, orgasm, BDSM, orgasm compilation, JOI, anal orgasm
15:53 70%

Prostate Massage

7 years ago

ShemaleZ

prostate, massage
31:37

Rectal w/ faux-cock untill i cum twice

3 months ago

ShemaleTaxi

shemale, anal, prostate
17:26 92%

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
18:59 81%

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

3 years ago

TrannyGem

prostate, big ass, massage, fetish, orgasm, milk, babe
26:32

Sheylla Wandergirlt Jizzes Firm W/ Rod in her Fuck-Hole

5 years ago

TrannyGem

prostate, teen anal (18+), cum in ass
58:42

Poke the prostate ②　Sayuki-Kana

4 years ago

TXXX

prostate, japanese
20:28

Chinese Crossdresser schoolgirl gets ravaged by sex machine

2 years ago

ShemaleTaxi

prostate, japanese, chinese, machine, taxi, crossdresser
22:44

Dildo Precum Milk Prostate

5 years ago

ShemaleZ

prostate, dildo, milk, toys
21:08

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

3 months ago

ShemaleTaxi

FTM, prostate, orgasm, creampie
16:00

Unboxing The Boogeyman dildo! (Sissygasms & Cumplay)

6 months ago

ShemaleMovie

prostate, orgasm, crossdresser, british, toys, sissy, femboy
36:09

Introducing U To Anal & Prostate Play

4 months ago

ShemaleZ

shemale, solo, prostate, lingerie
34:23

Cumshot 30:31 prostate cum 32:15

8 years ago

TXXX

prostate
15:22

Flawless ten hook-up Therapist Fucks Her Clients Ass

4 months ago

ShemaleTaxi

feet, strapon, prostate, orgasm, facial, babe, ass
29:12

Bonnie_Bell Prostate Tickler Jackoff Cums urinates All Over Herself

6 years ago

ShemaleZ

prostate
33:53

TSCHX sex cream flow thirty:31 Prostate cum 32:15

6 years ago

TXXX

prostate, amateur
31:39 53%

Compilation t-girls jizm while anal smash prostate

5 years ago

VideoSection

creampie, prostate, creampie compilation
16:41

Sissy Slut Bess wrecks her boipussy with beer bottle before squirting a massive load

2 years ago

xHamster

squirt, cumshot, sissy, anal orgasm, prostate, bottle
15:23 80%

Prostate Massage

6 years ago

ShemaleZ

prostate, massage, tattoo
21:10 75%

SDHSERIES - Sissy Diaries Day trio

4 years ago

TrannyGem

prostate, orgasm, dildo, BDSM, compilation, orgasm compilation, JOI
16:30

Prostate jerking...

4 years ago

ShemaleTaxi

latex, prostate, taxi
17:16 79%

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

3 years ago

ShemaleMovie

prostate, big ass, BBW, dildo, compilation, machine, fleshlight
41:49

GenderXFilms - super-naughty Nurse Checks Patients prostate wt Her yam-sized Cock

2 years ago

ShemaleTaxi

prostate, doctor, big cock
25:28

TGIRLS GONE insane 1 - gig four

6 years ago

HDSex

prostate, dogging, facial, ass licking, jerking, bikini
16:20 78%

Milk cow prostate cum

3 years ago

ShemaleZ

prostate, milk, selfsuck, crossdresser
20:20

Japanese Crossdresser college girl gets pummeled by orgy machine

9 months ago

ShemaleMovie

anal, orgy, prostate, crossdresser, machine
24:45

Miyuki masturbation

5 months ago

ShemaleTaxi

solo, japanese, prostate, crossdresser
16:23

Miyuki Masturbation 2

1 year ago

xHamster

latex, prostate, orgasm, japanese, masturbation, asian
21:07

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

5 years ago

TrannyGem

muscle, prostate, monster, anal orgasm, cum while fucked
41:53

GenderXFilms - Naughty Nurse Checks Patients Prostate wt Her Massive Cock

2 years ago

xHamster

prostate, shemale fucks guy
26:28

Tall anal fucktoys up her prostate

4 years ago

ShemaleTaxi

tall, prostate, hardcore
51:23 67%

Linzy19's Guide To Chastity

3 years ago

xHamster

prostate, fetish, BDSM, domination, JOI, chastity
16:30

Prostate milking & 1st wham-banger Jan-08-2013

13 years ago

xHamster

prostate, milk
20:57

[lunn]prostate Milking Challenge. Head-moving Plug Masturbation

4 years ago

HClips

prostate, milk, asian
15:01

Asian Crossdresser student uniform is faux-cock masturbation

2 years ago

ShemaleTaxi

student, japanese, prostate
18:29 67%

Pequeño sploog con mi mini bad dragon

3 years ago

TrannyGem

huge dildo, squirt, prostate, orgasm, riding
16:20

Prostate Milking...

5 years ago

xHamster

latex, prostate, orgasm, milk, anal orgasm
19:33

THE new TGIRL three - gig 4

5 years ago

ShemaleMovie

prostate, missionary
17:04

Sasha Earth shemale russian whore submissive fuck on the bed at home with anal sex toys in the ass dildo

3 years ago

xHamster

prostate, russian, whore
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
15:10

Crossdresser with BIG BLACK COCK fuck stick

3 months ago

TrannyGem

amateur, crossdresser, prostate
15:22

Perfect 10 Sex Therapist penetrates Her Clients bum

1 year ago

ShemaleMovie

shemale, babe, prostate, strapon
15:15

Multiple Prostate Orgasms For My Lingerie Clad Ass

1 year ago

HClips

asian, lingerie, shemale, prostate, handjob
23:51

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

3 years ago

ShemaleTaxi

prostate, milk, vibrator, taxi, femboy
23:18

Slutty gaping femboy and prostate orgasm at the end

1 year ago

XXXDan

prostate, cumshot, femboy, anal, amateur
34:23

TSCHX sex cream flow thirty:31 & Prostate cum 32:15

7 years ago

ShemaleZ

prostate
25:43 80%

Trans teenie got dual climax with electro-hitachi

4 years ago

TrannyGem

prostate, orgasm, double anal, electro, vibrator, double penetration, small cock
25:19

アネロスとオナホで大量射精する男の娘

3 years ago

ShemaleTaxi

prostate, taxi, fleshlight

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