SHEMALE • PROSTATE 271 videos

Popular Latest Top rated

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
31:30 90%

Compilation shemales cum while anal fuck prostate

3 years ago

TrannyOne

prostate, creampie compilation, compilation, cum while fucked, creampie
39:58 89%

Ts Dr. Chanel Noir: Home Prostate Exam

4 years ago

ShemaleZ

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

Prostate Exam

2 years ago

AShemaleTube

blowjob, prostate, shemale and girl, cumshot, masturbation, exam
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
18:06 88%

Lovely and bad tranny

6 years ago

TrannyGem

prostate, orgasm, redhead, masturbation, reality, vibrator, hands free
26:05 84%

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

2 years ago

TrannyGem

mom, shemale, prostate, massage, chubby, wife, MILF
26:05 84%

TRANNY AND HER FIRST-EVER DVP THREEWAY!!

8 months ago

TrannyGem

amateur, mom, shemale, prostate, threesome, massage, chubby
25:00 82%

Handsfree and prostate cumshots compilation

4 years ago

TrannyOne

prostate, cumshot compilation, hands free, compilation, amateur
36:48 82%

Prostate Epiphany With Erica Cherry And Whitney Wright

2 years ago

ShemaleZ

shemale, prostate
20:22 81%

Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
25:20 81%

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

10 months ago

ShemaleMovie

kissing, shemale, bisexual, prostate, threesome, massage, socks
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
17:07 80%

Odor prostate wanking JOI 4K

5 months ago

HDSex

POV, solo, JOI, shemale, masturbation, 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
15:23 80%

Prostate Massage

6 years ago

ShemaleZ

prostate, massage, tattoo
16:20 80%

Prostate Milking...

4 years ago

TrannyOne

prostate, milk
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
27:29 78%

SDHSERIES - Sissy Diaries Day ten

4 years ago

TrannyGem

prostate, orgasm, BDSM, orgasm compilation, JOI, anal orgasm
17:07 78%

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

3 years ago

TrannyGem

huge dildo, prostate, BBW, compilation, machine, cumshot compilation, hands free
20:08 78%

TranssexualAngel - Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
25:09 78%

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

7 years ago

ShemaleZ

prostate, ladyboy
16:20 78%

Milk cow prostate cum

3 years ago

ShemaleZ

prostate, milk, selfsuck, crossdresser
23:56 78%

Prostate Stimulation

3 years ago

Upornia

prostate, asian
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 75%

Sissygasm Compilation! Trans Konchaut Bez Ruk Podborka! Prostate Milking

3 years ago

Upornia

prostate, milk, compilation
21:10 75%

SDHSERIES - Sissy Diaries Day trio

4 years ago

TrannyGem

prostate, orgasm, dildo, BDSM, compilation, orgasm compilation, JOI
26:06 75%

TRANSGIRL AND HER first DVP three-way!!

7 months ago

ShemaleMovie

prostate, threesome, massage, husband, socks, frottage
35:04 75%

Wonderful tgirl Angel fake penis training

3 months ago

ShemaleMovie

small tits, anal, shemale, prostate, masturbation
34:36 74%

Prostate compilation

6 years ago

TXXX

prostate, compilation, toys, cumshot compilation
32:24 74%

Transgender Aubrey Kate Tears Up Puny Lilly Ford

6 years ago

TrannyGem

prostate, massage, nipples, 69, masturbation, shemale
19:15 73%

Hands Free Cum with huge Mr Hankeys Cody Cachet dildo

11 months ago

xHamster

huge dildo, anal, prostate, dildo, lingerie, riding, ass
36:09 71%

Jyosou Bishonen Prostate Lesson Prostate Lesson Mizuki Yukirin Crossdressing Beautiful Boy

9 months ago

XXXDan

amateur, crossdresser, japanese, beauty, shemale, prostate
24:29 70%

Handsfree And Prostate Cumshots Compilation

4 years ago

Upornia

prostate, compilation, cumshot compilation, hands free, solo
36:32 70%

Dame college girl pays an influential instructor for humiliation

7 months ago

ShemaleMovie

amateur, homemade, blowjob, prostate, couple, massage, russian
36:18 70%

Introducing You to Anal & Prostate Play

5 years ago

BeMyHole

prostate, solo, jerking, cumshot
15:53 70%

Prostate Massage

7 years ago

ShemaleZ

prostate, massage
20:03 67%

Hot Sissygasm Prostate Compilation

4 years ago

AShemaleTube

prostate, compilation, cumshot compilation, crossdresser, toys
26:41 67%

Prostate cum 23min12sec

6 years ago

ShemaleZ

prostate, cum in mouth
51:23 67%

Linzy19's Guide To Chastity

3 years ago

xHamster

prostate, fetish, BDSM, domination, JOI, chastity
25:32 67%

Prostate orgasm

5 years ago

xHamster

prostate, orgasm
18:59 67%

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

3 years ago

TrannyGem

prostate, massage, orgasm, chastity, milk
41:31 67%

Naughty Nurse Checks Patients Prostate Wt Her Massive Cock Indoors

2 years ago

BeMyHole

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

Pequeño sploog con mi mini bad dragon

3 years ago

TrannyGem

huge dildo, squirt, prostate, orgasm, riding
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
1:06:09 61%

Bang The spunk Out Of Him Trans Compilation 1-4

5 months ago

ShemaleTaxi

creampie, prostate, orgasm, creampie compilation, compilation, big cock, cumshot compilation
45:23 61%

Dani Peterson Prostate Penetration

4 years ago

TXXX

prostate, stockings
16:42 60%

Aroma Prostate Milking Joi 4k

2 years ago

ShemaleZ

small cock, prostate, big cock, JOI, solo
25:15 60%

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

7 months ago

TrannyGem

handjob, mature, mature anal, prostate, hairy, milk, compilation
53:00 60%

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

6 years ago

TrannyGem

prostate, orgasm, machine, orgasm compilation, femboy
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
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
24:19 57%

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

6 months ago

TrannyGem

mom, femdom, strapon, huge dildo, prostate, orgasm, fisting
49:30 57%

Transsexual SWINGERS three - gig 2

10 months ago

ShemaleMovie

skinny, shemale, lingerie, gangbang, prostate, swinger
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
17:36 56%

French Maid pulverizes ladyboy

6 years ago

HDSex

french, prostate, maid, crossdresser, sissy
31:39 53%

Compilation t-girls jizm while anal smash prostate

5 years ago

VideoSection

creampie, prostate, creampie compilation
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
51:27 50%

SweetandHot buttfuck & (pre)cumshow

1 year ago

ShemaleMovie

shemale, femboy, orgasm, big tits, masturbation, prostate
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
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

1 year ago

TrannyOne

femdom, strapon, doll, prostate, threesome, pegging
54:13 33%

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 )

4 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

9 months 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)

10 months ago

ShemaleMovie

femdom, teen (18+), strapon, prostate, couple, massage, russian
24:24 20%

How to make a good erotic video

2 years ago

xHamster

prostate, orgasm, mexican, erotic, anal orgasm, hands free
20:05 20%

Девушка хорошо сосала, ебала страпоном, делала римминг. Много спермы, кончил 2 раза.

10 months ago

ShemaleMovie

public, teen (18+), strapon, prostate, russian, teen anal (18+), outdoor
20:04 14%

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

6 months ago

TrannyGem

femdom, prostate, instruction, big tits, jerking, anime, futanari
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
29:34

2026 Handsfree Orgasms, Prostate Cumshot Part 3

4 days ago

$$ FapHouse

anal, sissy, amateur, orgasm, hands free, cumshot, solo
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
15:36

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

1 month ago

ShemaleZ

shemale, shemale fucks guy, doctor, babe, big tits, prostate
22:22

Prostate Orgasms Galore - Billie Beaumont

2 months ago

$$ FapHouse

black, anal, prostate, couple, interracial, orgasm, tattoo
20:03

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

3 months ago

ShemaleTaxi

prostate, orgasm, japanese, machine, penis, taxi, anal orgasm
16:20

Prostate Milking...

5 years ago

xHamster

latex, prostate, orgasm, milk, anal orgasm
23:25

2026 Handsfree Cumshot Prostate Jet. Part 1

2 weeks ago

$$ FapHouse

amateur, shemale, hands free
22:23

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

7 months ago

ShemaleMovie

cute, beauty, huge dildo, prostate, dildo, prostitute, babe
36:10

Fabulous arms free anal love

6 months ago

HDSex

big ass, masturbation, machine, toys, prostate
31:18

Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie

8 months ago

$$ FapHouse

amateur, stockings, french, prostate, massage, redhead, hardcore
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, gangbang, group, ass, orgy
19:06

Stunning Ts Vibrates Hur Prostate

3 years ago

Upornia

prostate, blonde, vibrator, solo
15:34

Miyuki masturbation

2 weeks ago

ShemaleMovie

toys, shemale, japanese, cumshot, amateur
27:49

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

3 months ago

ShemaleTaxi

shemale, JOI, futanari, POV
22:41

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

5 months ago

TrannyGem

cute, prostate, massage, teen anal (18+), riding, ass, toys
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, close up, sensual
29:12

Bonnie_Bell Prostate Tickler Jackoff Cums urinates All Over Herself

6 years ago

ShemaleZ

prostate
20:15

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

1 month ago

XXXVogue

shemale, sissy, hands free, prostate, vibrator
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
15:22

Flawless ten hook-up Therapist Fucks Her Clients Ass

4 months ago

ShemaleTaxi

feet, strapon, prostate, orgasm, facial, babe, ass
20:21

Kinky Trans Nurse Shows Home Guts Examination!

4 years ago

TrannyGem

prostate, nurse, maid, blowjob
18:27

Asian femboy Toolchannel takes a massive prostate massager for a ride after a dry orgasm

3 months ago

XXXVogue

shemale, crossdresser, prostate
31:50

Compilation of ladyboys cumming while getting their assholes pounded for prostate pleasure

1 year ago

XXXVogue

asshole, compilation, orgasm compilation, orgasm, prostate
17:15

Trans Compilation: Prostate Orgasms Galore!

1 year ago

XXXVogue

chinese, orgasm compilation, cumshot compilation, compilation
17:18

No hands cum Holly Hunt fucks her ass with immense faux-cocks until she has a prostate orgasm

1 year ago

ShemaleTaxi

huge dildo, prostate, orgasm, dildo, masturbation, gape, hands free
16:42

Cumdump Compilation - Big Booty Prostate Milking Big Dick Fleshlight Fucking & More

3 years ago

Upornia

prostate, milk, compilation, fleshlight
16:00

Unboxing The Boogeyman dildo! (Sissygasms & Cumplay)

6 months ago

ShemaleMovie

prostate, orgasm, crossdresser, british, toys, sissy, femboy
26:35

Denial and Wreck

6 months ago

TrannyGem

cute, POV, prostate, panties, ass, small tits, chastity
24:08

Sissygasm from anal onanism in sissy bi-atch with closed clittie in chastity_sc.26

10 months ago

ShemaleMovie

sissy, orgasm, cum in ass, prostate
18:22

Femboy fucks toy cock and cums

1 year ago

XXXVogue

dildo, femboy, homemade, cumshot, masturbation
18:11

Asian Crossdresser student gets humped by sex machine

2 years ago

ShemaleTaxi

student, japanese, dildo, prostate
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
19:49

Lovely lil trap rectal instructing

4 years ago

TrannyGem

train, prostate, instruction, riding
26:32

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

5 years ago

TrannyGem

prostate, teen anal (18+), cum in ass
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
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

6 months ago

ShemaleZ

POV, prostate, asian, orgasm, swallow, erotic, cosplay
15:09

Prostate milking leads to a mind-blowing ejaculation -

7 months ago

NuVid

milk, prostate
20:53

Warm blond maid plays with and pounds mind-blowing ladyboys butt

10 months ago

TrannyGem

prostate, couple, MILF, orgasm, maid, dildo, lingerie
17:17

Hands free cum Holly Hunt fucks her ass with massive dildos until she has a prostate orgasm

1 year ago

xHamster

amateur, prostate, cumshot, dildo, hands free
1:57:08

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

2 years ago

ShemaleZ

prostate, asian
41:26

Naughty Nurse Checks Patients Prostate Wt Her Massive Cock

2 years ago

BeMyHole

big tits, ass licking, small cock
41:53

GenderXFilms - Naughty Nurse Checks Patients Prostate wt Her Massive Cock

2 years ago

xHamster

prostate, shemale fucks guy
21:57

Prostate milking with cum cupcake

2 years ago

JizzBunker

pissing, prostate, fetish, orgasm, milk, vibrator
20:22

Sexy Excited Trans Nurse Shows Home Prostate Exam!

2 years ago

TrannyOne

prostate, nurse, exam

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