SHEMALE • PROSTATE 275 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 91%

Compilation shemales cum while anal fuck prostate

4 years ago

TrannyOne

prostate, creampie compilation, compilation, cum while fucked, creampie
34:39 90%

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
39:58 89%

Ts Dr. Chanel Noir: Home Prostate Exam

4 years ago

ShemaleZ

stockings, prostate, big tits, ass licking, exam
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
21:07 86%

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
26:05 85%

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!!

9 months ago

TrannyGem

amateur, mom, shemale, prostate, threesome, massage, chubby
25:00 83%

Handsfree and prostate cumshots compilation

4 years ago

TrannyOne

prostate, cumshot compilation, hands free, compilation, amateur
25:20 82%

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

11 months ago

ShemaleMovie

kissing, shemale, bisexual, prostate, threesome, massage, socks
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
25:43 80%

Trans teenie got dual climax with electro-hitachi

4 years ago

TrannyGem

small cock, prostate, orgasm, double anal, electro, vibrator, sissy
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 80%

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
18:59 79%

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

4 years ago

TrannyGem

prostate, big ass, massage, fetish, orgasm, milk, babe
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 76%

Sissygasm Compilation! Trans Konchaut Bez Ruk Podborka! Prostate Milking

3 years ago

Upornia

prostate, milk, compilation
34:36 75%

Prostate compilation

6 years ago

TXXX

prostate, compilation, toys, cumshot compilation
17:07 75%

Odor prostate wanking JOI 4K

6 months ago

HDSex

POV, solo, JOI, shemale, masturbation, prostate
19:15 75%

Hands Free Cum with huge Mr Hankeys Cody Cachet dildo

1 year ago

xHamster

huge dildo, anal, prostate, dildo, lingerie, riding, ass
26:06 75%

TRANSGIRL AND HER first DVP three-way!!

8 months ago

ShemaleMovie

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

Wonderful tgirl Angel fake penis training

4 months ago

ShemaleMovie

small tits, anal, shemale, prostate, masturbation
32:24 75%

Transgender Aubrey Kate Tears Up Puny Lilly Ford

6 years ago

TrannyGem

prostate, massage, nipples, 69, masturbation, shemale
21:10 74%

SDHSERIES - Sissy Diaries Day trio

4 years ago

TrannyGem

prostate, orgasm, dildo, BDSM, compilation, orgasm compilation, JOI
36:18 73%

Introducing You to Anal & Prostate Play

5 years ago

BeMyHole

prostate, solo, jerking, cumshot
36:09 71%

Jyosou Bishonen Prostate Lesson Prostate Lesson Mizuki Yukirin Crossdressing Beautiful Boy

10 months ago

XXXDan

amateur, crossdresser, japanese, beauty, shemale, prostate
24:29 71%

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

8 months ago

ShemaleMovie

amateur, homemade, prostate, couple, massage, russian, BDSM
15:53 70%

Prostate Massage

7 years ago

ShemaleZ

prostate, massage
51:23 67%

Linzy19's Guide To Chastity

3 years ago

xHamster

prostate, fetish, BDSM, domination, JOI, chastity
26:41 67%

Prostate cum 23min12sec

6 years ago

ShemaleZ

prostate, cum in mouth
41:31 67%

Naughty Nurse Checks Patients Prostate Wt Her Massive Cock Indoors

2 years ago

BeMyHole

domination, shemale fucks guy, bareback, prostate, nurse
20:03 67%

Hot Sissygasm Prostate Compilation

4 years ago

AShemaleTube

prostate, compilation, cumshot compilation, crossdresser, toys
18:29 67%

Pequeño sploog con mi mini bad dragon

3 years ago

TrannyGem

huge dildo, squirt, prostate, orgasm, riding
18:59 67%

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

3 years ago

TrannyGem

prostate, massage, orgasm, chastity, milk
25:32 67%

Prostate orgasm

5 years ago

xHamster

prostate, orgasm
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
45:23 63%

Dani Peterson Prostate Penetration

5 years ago

TXXX

prostate, stockings
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
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
24:14 60%

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

9 months ago

TrannyGem

amateur, cute, anal, prostate, massage, orgasm, babe
53:00 60%

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

6 years ago

TrannyGem

prostate, orgasm, machine, orgasm compilation, femboy
22:10 60%

All of my prostate milking

1 year ago

AShemaleTube

stockings, crossdresser, mature, prostate
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+), masturbation, close up, sissy, femboy
17:36 59%

French Maid pulverizes ladyboy

6 years ago

HDSex

french, prostate, maid, crossdresser, sissy
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
19:04 57%

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

4 years ago

TrannyGem

cute, prostate, groped, massage, teen anal (18+), milk, crossdresser
24:19 56%

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

7 months ago

TrannyGem

mom, femdom, strapon, huge dildo, prostate, orgasm, fisting
31:39 53%

Compilation t-girls jizm while anal smash prostate

6 years ago

VideoSection

creampie, prostate, creampie compilation
18:49 50%

Miruku Aima Prostate Squirt Sex

9 years ago

xHamster

squirt, prostate, ladyboy
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
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
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 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 )

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

10 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)

11 months 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.

11 months 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]

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 weeks ago

$$ FapHouse

prostate, asian, orgasm, ass, machine, sissy, hands free
20:58

Naomi precum buttfuck pounding

1 week ago

ShemaleMovie

shemale, ebony, dildo, teen (18+)
41:12

2026 Prostate Orgasm Part 5

2 weeks ago

$$ FapHouse

orgasm, solo, sissy, amateur, prostate
15:36

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

2 months ago

ShemaleZ

shemale, shemale fucks guy, doctor, babe, big tits, prostate
18:22

Femboy rides plaything dick & cums

3 weeks ago

ShemaleTaxi

amateur, small cock, anal, prostate, dildo, cumshot, riding
15:37

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

6 days ago

JizzBunker

exam, shemale, anal
22:22

Prostate Orgasms Galore - Billie Beaumont

2 months ago

$$ FapHouse

black, anal, prostate, couple, interracial, asian, orgasm
17:15

Trans Compilation: Prostate Orgasms Galore!

1 year ago

XXXVogue

chinese, orgasm compilation, cumshot compilation, compilation
31:18

Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie

9 months ago

$$ FapHouse

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

Sexy Excited Trans Nurse Shows Home Prostate Exam!

3 years ago

TrannyOne

prostate, nurse, exam
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
36:10

Fabulous arms free anal love

7 months ago

HDSex

big ass, masturbation, machine, toys, prostate
23:25

2026 Handsfree Cumshot Prostate Jet. Part 1

1 month ago

$$ FapHouse

amateur, shemale, hands free
1:57:08

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

2 years ago

ShemaleZ

prostate, asian
19:06

Stunning Ts Vibrates Hur Prostate

3 years ago

Upornia

prostate, blonde, vibrator, solo
58:42

Poke the prostate ②　Sayuki-Kana

4 years ago

TXXX

prostate, japanese
15:22

Flawless ten hook-up Therapist Fucks Her Clients Ass

5 months ago

ShemaleTaxi

feet, strapon, prostate, orgasm, facial, babe, ass
15:02

Trap Finishes Off while railing a Monster Fake Penis

4 years ago

TrannyGem

huge dildo, prostate, monster, penis, cum while fucked
32:02

Erected tranny smmys0f1 doggy prostate cum September-30-2021 03-48-35: Porn

3 months ago

XXXDan

shemale, amateur, prostate
22:23

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

8 months ago

ShemaleMovie

cute, beauty, huge dildo, prostate, dildo, prostitute, babe
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
29:41

Jerks off horny latte and massages his prostate with a fat dildo

3 years ago

xHamster

fat, prostate, massage, jerking
17:05

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

3 years ago

ShemaleTaxi

femdom, prostate, massage, milk, taxi
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
20:59

The ladyboy That Takes It In The Fanny - gig 1

5 years ago

ShemaleTaxi

public, voyeur, prostate, nylon, hardcore
20:15

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

2 months 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

3 months ago

XXXVogue

prostate, orgasm, japanese, dildo, machine
24:08

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

11 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
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
15:50

Prostate cum on my feet

3 months ago

XXXVogue

shemale, feet, solo, fisting
36:09

Introducing U To Anal & Prostate Play

5 months ago

ShemaleZ

shemale, solo, prostate, 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
22:58

[Aneros] practice edible delectation with TEMPO and intense orgasms with HELIX

1 month ago

ShemaleTaxi

ladyboy, massage
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
26:35

Denial and Wreck

7 months ago

TrannyGem

cute, POV, prostate, panties, ass, small tits, chastity
51:25

Linzy19s Guide To purity

8 months ago

ShemaleMovie

domination, shemale, amateur, prostate
1:08:08

Ultimate Sissy palms Free ejaculation Compilation

8 months ago

ShemaleMovie

sissy, compilation, prostate
23:47

[Japanese Femboy - FULL] Protracted Popshot of Palms Free-For-All Jism and Mitt Job !

1 year ago

TrannyGem

prostate, orgasm, sissy, anal orgasm, hands free, cosplay
35:56

My horny stepbrother fucked me after school

2 years ago

xHamster

german, prostate, shemale and girl, anal orgasm
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

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