SHEMALE • PROSTATE 293 videos

Popular Latest Top rated

34:36 80%

Prostate compilation

7 years ago

TXXX

prostate, compilation, toys, cumshot compilation
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
26:05 83%

TRANNY AND HER FIRST-EVER DVP THREEWAY!!

1 year ago

TrannyGem

amateur, mom, shemale, prostate, threesome, massage, chubby
20:22 81%

Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
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
26:05 84%

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

2 years ago

TrannyGem

mom, shemale, prostate, massage, chubby, wife, MILF
17:07 75%

Odor prostate wanking JOI 4K

11 months ago

HDSex

POV, solo, JOI, shemale, masturbation, prostate
41:12

2026 Prostate Orgasm Part 5

5 months ago

$$ FapHouse

orgasm, solo, sissy, amateur, prostate, machine
25:11 76%

Sissygasm Compilation! Trans Konchaut Bez Ruk Podborka! Prostate Milking

4 years ago

Upornia

prostate, milk, compilation
15:36 40%

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
20:13

Steaming Sissygasm prostate Compilation

2 weeks ago

ShemaleMovie

compilation, cumshot compilation, crossdresser, amateur, prostate
24:29 73%

Handsfree And Prostate Cumshots Compilation

4 years ago

Upornia

prostate, compilation, cumshot compilation, hands free, solo
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
36:09 74%

Jyosou Bishonen Prostate Lesson Prostate Lesson Mizuki Yukirin Crossdressing Beautiful Boy

1 year ago

XXXDan

amateur, crossdresser, japanese, beauty, shemale, prostate
39:58 88%

Ts Dr. Chanel Noir: Home Prostate Exam

4 years ago

ShemaleZ

stockings, prostate, big tits, ass licking, exam
36:18 77%

Introducing You to Anal & Prostate Play

5 years ago

BeMyHole

prostate, solo, jerking, cumshot
45:23 63%

Dani Peterson Prostate Penetration

5 years ago

TXXX

prostate, stockings
16:28

Prostate orgasms cumpilation. Personalsin collection vol. 157

1 month ago

AShemaleTube

shemale, cumshot compilation, orgasm, prostate
20:08 78%

TranssexualAngel - Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
18:53 73%

Female dominance IDEAS - TOP 10 bonus

1 month ago

HDSex

handjob, shemale, train, prostate, orgasm, BDSM, 18
1:06:09 63%

Bang The spunk Out Of Him Trans Compilation 1-4

11 months ago

ShemaleTaxi

creampie, prostate, orgasm, creampie compilation, compilation, big cock, cumshot compilation
18:49 50%

Miruku Aima Prostate Squirt Sex

9 years ago

xHamster

squirt, prostate, ladyboy
21:10 75%

SDHSERIES - Sissy Diaries Day trio

4 years ago

TrannyGem

prostate, orgasm, dildo, BDSM, compilation, orgasm compilation, JOI
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
22:22

Prostate Orgasms Galore - Billie Beaumont

7 months ago

$$ FapHouse

black, anal, prostate, couple, interracial, orgasm, tattoo
26:41 67%

Prostate cum 23min12sec

6 years ago

ShemaleZ

prostate, cum in mouth
36:32 67%

Dame college girl pays an influential instructor for humiliation

1 year ago

ShemaleMovie

amateur, homemade, prostate, couple, massage, russian, BDSM
16:42 60%

Aroma Prostate Milking Joi 4k

3 years ago

ShemaleZ

small cock, prostate, big cock, JOI, solo
51:27 50%

SweetandHot buttfuck & (pre)cumshow

1 year ago

ShemaleMovie

shemale, femboy, orgasm, big tits, masturbation, prostate
26:06 75%

TRANSGIRL AND HER first DVP three-way!!

1 year ago

ShemaleMovie

prostate, threesome, massage, husband, socks, frottage
18:22 80%

Femboy rides plaything dick & cums

5 months ago

ShemaleTaxi

small cock, anal, prostate, cumshot, riding, toys, taxi
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
49:30 57%

Transsexual SWINGERS three - gig 2

1 year ago

ShemaleMovie

skinny, shemale, lingerie, gangbang, prostate, swinger
35:04 73%

Wonderful tgirl Angel fake penis training

9 months ago

ShemaleMovie

small tits, anal, shemale, prostate, masturbation
34:36 43%

Prostate compilation

6 years ago

ShemaleZ

prostate, compilation, cumshot, cumshot compilation
31:30 83%

Compilation shemales cum while anal fuck prostate

4 years ago

TrannyOne

prostate, 18, creampie compilation, compilation, cum while fucked
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
1:08:08

Ultimate Sissy palms Free ejaculation Compilation

1 year ago

ShemaleMovie

sissy, compilation, prostate
20:22

Sexy Excited Trans Nurse Shows Home Prostate Exam!

3 years ago

TrannyOne

prostate, nurse, exam
20:03 67%

Hot Sissygasm Prostate Compilation

4 years ago

AShemaleTube

prostate, compilation, cumshot compilation, crossdresser, toys
25:00 85%

Handsfree and prostate cumshots compilation

4 years ago

TrannyOne

prostate, cumshot compilation, hands free, compilation, amateur
17:36 61%

French Maid pulverizes ladyboy

6 years ago

HDSex

french, prostate, maid, crossdresser, sissy
32:24 74%

Transgender Aubrey Kate Tears Up Puny Lilly Ford

7 years ago

TrannyGem

prostate, massage, nipples, 69, masturbation, shemale
36:10

Fabulous arms free anal love

11 months ago

HDSex

big ass, masturbation, machine, toys, prostate
45:23 77%

Big breast shemale Dani Peterson Prostate Penetration

5 years ago

Analdin

stockings, prostate, brazil, big tits, ass licking, babe, erotic
16:16 50%

Fledgling, hd videos, hands free prostate orgasm

2 months ago

XXXVogue

anal, prostate, orgasm, crossdresser, riding, babe, sissy
16:20 88%

Milk cow prostate cum

3 years ago

ShemaleZ

prostate, milk, selfsuck, crossdresser
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

cute, anal, prostate, chubby, orgasm, anal orgasm, cum while fucked
19:06

Stunning Ts Vibrates Hur Prostate

3 years ago

Upornia

prostate, blonde, vibrator, solo
18:06 88%

Lovely and bad tranny

7 years ago

TrannyGem

prostate, orgasm, redhead, masturbation, reality, vibrator, hands free
1:57:08 80%

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

2 years ago

ShemaleZ

prostate, asian
25:32 67%

Prostate orgasm

6 years ago

xHamster

prostate, orgasm
16:13

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

2 months ago

ShemaleMovie

orgasm, prostate, chastity
38:49

You make me perceive magnificent

1 month ago

ShemaleTaxi

taxi, BBW, prostate
26:35

Denial and Wreck

1 year ago

TrannyGem

cute, POV, prostate, panties, ass, small tits, chastity
31:30 45%

Compilation shemales cum while anal fuck prostate

8 years ago

TXXX

prostate, creampie compilation, compilation, cum while fucked, masturbation
29:42

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

2 weeks ago

VideoSection

handjob, huge dildo, prostate, massage, BBW, jerking, toys
27:43

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

1 week ago

ShemaleMovie

game, crossdresser, prostate, femboy, sissy
22:51

TRANNY extreme 4 - gig trio

4 years ago

ShemaleTaxi

prostate, ass licking, deepthroat, taxi
21:19

Transgirl Masterbates in Block Shootout

2 months ago

ShemaleMovie

masturbation, orgasm, prostate
25:09 83%

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

7 years ago

ShemaleZ

prostate, ladyboy
49:39

Ts SWINGERS trio - sequence 2

5 years ago

ShemaleTaxi

swinger, prostate, gangbang, skinny
16:43

Alone Again ShibbySays JOI

3 weeks ago

ShemaleTaxi

massage, JOI, solo, small cock, prostate
25:20 80%

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

1 year ago

ShemaleMovie

kissing, bisexual, prostate, threesome, massage, socks, frottage
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
20:21

Kinky Trans Nurse Shows Home Guts Examination!

4 years ago

TrannyGem

prostate, nurse, maid, blowjob
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
15:22

Flawless ten hook-up Therapist Fucks Her Clients Ass

9 months ago

ShemaleTaxi

feet, strapon, train, prostate, orgasm, facial, babe
51:25

Linzy19s Guide To purity

1 year ago

ShemaleMovie

domination, shemale, amateur, prostate
35:58

My naughty stepbrother pulverized me after college

9 months ago

ShemaleMovie

small cock, german, anal, prostate, orgasm, shemale and girl, heels
31:18

Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie

1 year ago

$$ FapHouse

stockings, french, prostate, massage, redhead, hardcore
20:03

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

8 months ago

ShemaleTaxi

prostate, orgasm, japanese, machine, penis, taxi, anal orgasm
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
36:09

Introducing U To Anal & Prostate Play

9 months ago

ShemaleZ

shemale, solo, prostate, lingerie
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
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
23:42

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

7 years ago

ShemaleZ

prostate, milk
17:15

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

4 weeks ago

ShemaleMovie

huge dildo, prostate, massage, dildo, solo, riding, babe
34:23

TSCHX Cumshot 30:31 & Prostate Cum 32:15

8 years ago

xHamster

prostate
36:47 88%

Prostate Exam

2 years ago

AShemaleTube

blowjob, prostate, shemale and girl, cumshot, masturbation, exam
17:05

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

3 years ago

ShemaleTaxi

femdom, prostate, massage, milk, taxi
41:31 67%

Naughty Nurse Checks Patients Prostate Wt Her Massive Cock Indoors

2 years ago

BeMyHole

domination, shemale fucks guy, bareback, prostate, nurse
16:05 40%

Unique Pegging Threesome Adventure with Trans Doll

2 years ago

TrannyOne

femdom, strapon, doll, prostate, threesome, pegging
18:11

Asian Crossdresser student gets humped by sex machine

2 years ago

ShemaleTaxi

student, japanese, dildo, prostate
24:16

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

2 months ago

ShemaleMovie

beauty, prostate, massage, orgasm, cum in mouth, cum in ass
22:44

Dildo Precum Milk Prostate

5 years ago

ShemaleZ

prostate, dildo, milk, toys
24:45

Miyuki masturbation

10 months ago

ShemaleTaxi

solo, japanese, prostate, crossdresser
23:56 78%

Prostate Stimulation

4 years ago

Upornia

prostate, asian, ladyboy
15:53 70%

Prostate Massage

8 years ago

ShemaleZ

prostate, massage
16:58

Prostate_play - threesome with orgy girl and iron dildo - pt1

4 months ago

VideoSection

shemale, pantyhose, crossdresser, massage, dildo, prostate
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
16:27

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

1 week ago

AShemaleTube

prostate, tease, maid, dildo, riding, goth, fleshlight
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
51:28

MangoK buttfuck cum from monster dildo

1 year ago

ShemaleMovie

femboy, small cock, monster, prostate
24:35

Miyuki masturbation

1 year ago

xHamster

amateur, crossdresser, prostate, japanese
17:59

Amateur Sissy female dom Compilation two

6 days ago

ShemaleMovie

strapon, sissy, crossdresser, amateur, compilation, prostate, handjob
20:58

Naomi precum buttfuck pounding

4 months ago

ShemaleMovie

shemale, ebony, dildo, teen (18+), prostate, teen anal (18+)
25:43 89%

Trans nubile got dual ejaculation with vibro

4 years ago

TrannyGem

prostate, teen anal (18+), orgasm, latina, double anal, vibrator, sissy
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
58:42

Poke the prostate ②　Sayuki-Kana

4 years ago

TXXX

prostate, japanese
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
34:23

Cumshot 30:31 prostate cum 32:15

8 years ago

TXXX

prostate
29:12

Bonnie_Bell Prostate Tickler Jackoff Cums urinates All Over Herself

6 years ago

ShemaleZ

prostate
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
33:53

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

6 years ago

TXXX

prostate, amateur
15:37

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

7 months ago

XXXDan

prostate, missionary
51:23 57%

Linzy19's Guide To Chastity

3 years ago

xHamster

prostate, fetish, BDSM, domination, JOI, chastity
23:25

2026 Handsfree Cumshot Prostate Jet. Part 1

5 months ago

$$ FapHouse

amateur, shemale, hands free, prostate
25:15

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

8 months ago

ShemaleMovie

creampie, femboy, dildo, japanese, huge dildo, prostate
25:28

TGIRLS GONE insane 1 - gig four

6 years ago

HDSex

prostate, dogging, facial, ass licking, jerking, bikini
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
31:39 53%

Compilation t-girls jizm while anal smash prostate

6 years ago

VideoSection

creampie, prostate, creampie compilation
26:32

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

6 years ago

TrannyGem

prostate, teen anal (18+), cum in ass
17:12

She-male pummel and piss

3 months ago

ShemaleMovie

dildo, shemale fucks guy, thai, prostate
15:22

Perfect 10 Sex Therapist penetrates Her Clients bum

2 years ago

ShemaleMovie

shemale, babe, prostate, strapon
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
20:28

Chinese Crossdresser schoolgirl gets ravaged by sex machine

3 years ago

ShemaleTaxi

prostate, japanese, chinese, machine, taxi, crossdresser
16:20

Prostate Milking...

5 years ago

xHamster

latex, prostate, orgasm, milk, anal orgasm

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