SHEMALE • PROSTATE 288 videos

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34:36 81%

Prostate compilation

7 years ago

TXXX

prostate, compilation, toys, cumshot compilation
34:39 91%

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

1 year ago

ShemaleZ

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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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20:22 81%

Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
26:05 83%

TRANNY AND HER FIRST-EVER DVP THREEWAY!!

1 year ago

TrannyGem

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41:12

2026 Prostate Orgasm Part 5

4 months ago

$$ FapHouse

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17:07 75%

Odor prostate wanking JOI 4K

10 months ago

HDSex

POV, solo, JOI, shemale, masturbation, prostate
26:05 84%

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

2 years ago

TrannyGem

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25:11 76%

Sissygasm Compilation! Trans Konchaut Bez Ruk Podborka! Prostate Milking

4 years ago

Upornia

prostate, milk, compilation
15:36

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

6 months ago

ShemaleZ

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16:28

Prostate orgasms cumpilation. Personalsin collection vol. 157

1 month ago

AShemaleTube

shemale, cumshot compilation, orgasm, prostate
18:53 67%

Female dominance IDEAS - TOP 10 bonus

2 weeks ago

HDSex

handjob, shemale, train, prostate, orgasm, BDSM, 18
24:29 72%

Handsfree And Prostate Cumshots Compilation

4 years ago

Upornia

prostate, compilation, cumshot compilation, hands free, solo
39:58 88%

Ts Dr. Chanel Noir: Home Prostate Exam

4 years ago

ShemaleZ

stockings, prostate, big tits, ass licking, exam
45:23 64%

Dani Peterson Prostate Penetration

5 years ago

TXXX

prostate, stockings
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
20:08 78%

TranssexualAngel - Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
18:49 50%

Miruku Aima Prostate Squirt Sex

9 years ago

xHamster

squirt, prostate, ladyboy
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

cute, anal, prostate, chubby, orgasm, anal orgasm, cum while fucked
2:17:13 56%

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

1 year ago

ShemaleZ

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1:06:09 63%

Bang The spunk Out Of Him Trans Compilation 1-4

10 months ago

ShemaleTaxi

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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
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
21:10 75%

SDHSERIES - Sissy Diaries Day trio

4 years ago

TrannyGem

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36:18 77%

Introducing You to Anal & Prostate Play

5 years ago

BeMyHole

prostate, solo, jerking, cumshot
38:49

You make me perceive magnificent

1 week ago

ShemaleTaxi

taxi, BBW, prostate
26:41 67%

Prostate cum 23min12sec

6 years ago

ShemaleZ

prostate, cum in mouth
18:22 80%

Femboy rides plaything dick & cums

4 months ago

ShemaleTaxi

small cock, anal, prostate, dildo, cumshot, riding, toys
22:22

Prostate Orgasms Galore - Billie Beaumont

6 months ago

$$ FapHouse

black, anal, prostate, couple, interracial, orgasm, tattoo
36:32 67%

Dame college girl pays an influential instructor for humiliation

1 year ago

ShemaleMovie

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51:27 50%

SweetandHot buttfuck & (pre)cumshow

1 year ago

ShemaleMovie

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49:30 57%

Transsexual SWINGERS three - gig 2

1 year ago

ShemaleMovie

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16:16 50%

Fledgling, hd videos, hands free prostate orgasm

1 month ago

XXXVogue

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34:36 43%

Prostate compilation

6 years ago

ShemaleZ

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35:04 73%

Wonderful tgirl Angel fake penis training

8 months ago

ShemaleMovie

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19:04 58%

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

4 years ago

TrannyGem

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36:03 41%

New Tgirl Series Part I. Beautiful Trans Maria

3 years ago

ShemaleZ

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16:42 60%

Aroma Prostate Milking Joi 4k

3 years ago

ShemaleZ

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31:30 83%

Compilation shemales cum while anal fuck prostate

4 years ago

TrannyOne

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26:06 75%

TRANSGIRL AND HER first DVP three-way!!

12 months ago

ShemaleMovie

prostate, threesome, massage, husband, socks, frottage
19:15 77%

Hands Free Cum with huge Mr Hankeys Cody Cachet dildo

1 year ago

xHamster

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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

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25:00 85%

Handsfree and prostate cumshots compilation

4 years ago

TrannyOne

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36:10

Fabulous arms free anal love

11 months ago

HDSex

big ass, masturbation, machine, toys, prostate
1:08:08

Ultimate Sissy palms Free ejaculation Compilation

1 year ago

ShemaleMovie

sissy, compilation, prostate
45:23 77%

Big breast shemale Dani Peterson Prostate Penetration

5 years ago

Analdin

stockings, prostate, brazil, big tits, ass licking, babe, erotic
32:24 75%

Transgender Aubrey Kate Tears Up Puny Lilly Ford

7 years ago

TrannyGem

prostate, massage, nipples, 69, masturbation, shemale
17:36 61%

French Maid pulverizes ladyboy

6 years ago

HDSex

french, prostate, maid, crossdresser, sissy
19:06

Stunning Ts Vibrates Hur Prostate

3 years ago

Upornia

prostate, blonde, vibrator, solo
1:57:08

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

2 years ago

ShemaleZ

prostate, asian
18:06 88%

Lovely and bad tranny

7 years ago

TrannyGem

prostate, orgasm, redhead, masturbation, reality, vibrator, hands free
31:30 40%

Compilation shemales cum while anal fuck prostate

8 years ago

TXXX

prostate, creampie compilation, compilation, cum while fucked, masturbation
25:32 67%

Prostate orgasm

6 years ago

xHamster

prostate, orgasm
16:20 87%

Milk cow prostate cum

3 years ago

ShemaleZ

prostate, milk, selfsuck, crossdresser
22:51

TRANNY extreme 4 - gig trio

4 years ago

ShemaleTaxi

prostate, ass licking, deepthroat, taxi
25:20 80%

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

1 year ago

ShemaleMovie

kissing, shemale, bisexual, prostate, threesome, massage, socks
25:09 83%

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

7 years ago

ShemaleZ

prostate, ladyboy
16:13

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

1 month ago

ShemaleMovie

orgasm, prostate, chastity
49:39

Ts SWINGERS trio - sequence 2

5 years ago

ShemaleTaxi

swinger, prostate, gangbang, skinny
20:21

Kinky Trans Nurse Shows Home Guts Examination!

4 years ago

TrannyGem

prostate, nurse, maid, blowjob
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
23:25

2026 Handsfree Cumshot Prostate Jet. Part 1

5 months ago

$$ FapHouse

amateur, shemale, hands free, prostate
51:25

Linzy19s Guide To purity

1 year ago

ShemaleMovie

domination, shemale, amateur, prostate
15:22

Flawless ten hook-up Therapist Fucks Her Clients Ass

9 months ago

ShemaleTaxi

feet, strapon, train, prostate, orgasm, facial, babe
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
16:58

Prostate_play - threesome with orgy girl and iron dildo - pt1

3 months ago

VideoSection

shemale, pantyhose, crossdresser, massage, dildo, prostate
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
31:18

Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie

1 year ago

$$ FapHouse

stockings, french, prostate, massage, redhead, hardcore
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
24:45

Miyuki masturbation

10 months ago

ShemaleTaxi

solo, japanese, prostate, crossdresser
36:48 82%

Prostate Epiphany With Erica Cherry And Whitney Wright

2 years ago

ShemaleZ

shemale, prostate
21:19

Transgirl Masterbates in Block Shootout

1 month ago

ShemaleMovie

masturbation, orgasm, prostate
51:28

MangoK buttfuck cum from monster dildo

1 year ago

ShemaleMovie

femboy, small cock, monster, prostate
27:29 83%

SDHSERIES - Sissy Diaries Day ten

5 years ago

TrannyGem

prostate, orgasm, BDSM, orgasm compilation, small tits, JOI, sissy
23:42

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

6 years ago

ShemaleZ

prostate, milk
20:58

Naomi precum buttfuck pounding

4 months ago

ShemaleMovie

shemale, ebony, dildo, teen (18+), prostate, teen anal (18+)
24:35

Miyuki masturbation

1 year ago

xHamster

amateur, crossdresser, prostate, japanese
34:23

TSCHX Cumshot 30:31 & Prostate Cum 32:15

8 years ago

xHamster

prostate
41:31 67%

Naughty Nurse Checks Patients Prostate Wt Her Massive Cock Indoors

2 years ago

BeMyHole

domination, shemale fucks guy, bareback, prostate, nurse
36:47 88%

Prostate Exam

2 years ago

AShemaleTube

blowjob, prostate, shemale and girl, cumshot, masturbation, exam
16:05 40%

Unique Pegging Threesome Adventure with Trans Doll

2 years ago

TrannyOne

femdom, strapon, doll, prostate, threesome, pegging
15:53 70%

Prostate Massage

8 years ago

ShemaleZ

prostate, massage
23:56 78%

Prostate Stimulation

4 years ago

Upornia

prostate, asian, ladyboy
22:44

Dildo Precum Milk Prostate

5 years ago

ShemaleZ

prostate, dildo, milk, toys
18:11

Asian Crossdresser student gets humped by sex machine

2 years ago

ShemaleTaxi

student, japanese, dildo, prostate
17:05

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

3 years ago

ShemaleTaxi

femdom, prostate, massage, milk, taxi
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
31:50

Compilation shemales cum while anal poke prostate

2 weeks ago

ShemaleTaxi

orgasm compilation, orgasm, anal orgasm, compilation, prostate, solo
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
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
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
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
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
2:37:18

Nvh-008 Poke Deep Into The Prostate With A Real Cock! B

2 years ago

ShemaleZ

asian, prostate
58:42

Poke the prostate ②　Sayuki-Kana

4 years ago

TXXX

prostate, japanese
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
29:12

Bonnie_Bell Prostate Tickler Jackoff Cums urinates All Over Herself

6 years ago

ShemaleZ

prostate
16:35

Ladyboy Crossdresser Mighty assfuck getting off jism many times

10 months ago

TrannyGem

prostate, dildo, femboy
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
18:59 79%

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

4 years ago

TrannyGem

prostate, massage, fetish, orgasm, milk, babe, chastity
15:22

Perfect 10 Sex Therapist penetrates Her Clients bum

2 years ago

ShemaleMovie

shemale, babe, prostate, strapon
26:32

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

6 years ago

TrannyGem

prostate, teen anal (18+), cum in ass
22:23

Cute pretty shemale mega-slut Sasha Earth in tights on bed fucking big butt hard sex toys dildo

1 year ago

ShemaleMovie

cute, huge dildo, prostate, dildo, prostitute, toys, tight
25:43 89%

Trans nubile got dual ejaculation with vibro

4 years ago

TrannyGem

prostate, teen anal (18+), orgasm, latina, double anal, vibrator, sissy
16:00

Unboxing The Boogeyman dildo! (Sissygasms & Cumplay)

11 months ago

ShemaleMovie

prostate, orgasm, crossdresser, british, toys, sissy
20:28

Chinese Crossdresser schoolgirl gets ravaged by sex machine

3 years ago

ShemaleTaxi

prostate, japanese, chinese, machine, taxi, crossdresser
31:39 53%

Compilation t-girls jizm while anal smash prostate

6 years ago

VideoSection

creampie, prostate, creampie compilation
25:28

TGIRLS GONE insane 1 - gig four

6 years ago

HDSex

prostate, dogging, facial, ass licking, jerking, bikini
16:29

YES! ravage This Locked Up great girl

5 months ago

ShemaleMovie

prostate, femboy, sissy, machine
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
15:23 82%

Prostate Massage

6 years ago

ShemaleZ

prostate, massage, tattoo
16:20

Prostate Milking...

5 years ago

xHamster

latex, prostate, orgasm, milk, anal orgasm
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
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
26:35

Denial and Wreck

11 months ago

TrannyGem

cute, POV, prostate, panties, ass, small tits, chastity

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