SHEMALE • PROSTATE 280 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
34:39 90%

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

1 year ago

ShemaleZ

prostate, big tits, blonde, cum in mouth, small tits
16:30 90%

Prostate jerking...

5 years ago

ShemaleTaxi

latex, prostate, taxi
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
39:58 88%

Ts Dr. Chanel Noir: Home Prostate Exam

4 years ago

ShemaleZ

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

Prostate Exam

2 years ago

AShemaleTube

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

Lovely and bad tranny

7 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 84%

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

2 years ago

TrannyGem

mom, shemale, prostate, massage, chubby, wife, MILF
25:00 84%

Handsfree and prostate cumshots compilation

4 years ago

TrannyOne

prostate, cumshot compilation, hands free, compilation, amateur
16:24 84%

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
26:05 83%

TRANNY AND HER FIRST-EVER DVP THREEWAY!!

11 months ago

TrannyGem

amateur, mom, shemale, prostate, threesome, massage, chubby
25:20 83%

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
16:20 83%

Milk cow prostate cum

3 years ago

ShemaleZ

prostate, milk, selfsuck, crossdresser
31:30 83%

Compilation shemales cum while anal fuck prostate

4 years ago

TrannyOne

prostate, creampie compilation, compilation, cum while fucked, creampie, shemale
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
27:29 81%

SDHSERIES - Sissy Diaries Day ten

4 years ago

TrannyGem

prostate, orgasm, BDSM, orgasm compilation, small tits, JOI, sissy
25:43 81%

Trans teenie got dual climax with electro-hitachi

4 years ago

TrannyGem

small cock, prostate, orgasm, double anal, electro, vibrator, double penetration
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

4 years ago

ShemaleMovie

prostate, BBW, dildo, compilation, machine, fleshlight
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
17:07 79%

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

4 years ago

TrannyGem

huge dildo, prostate, BBW, milk, compilation, machine, cumshot compilation
34:36 79%

Prostate compilation

6 years ago

TXXX

prostate, compilation, toys, cumshot compilation
26:06 79%

TRANSGIRL AND HER first DVP three-way!!

10 months ago

ShemaleMovie

prostate, threesome, massage, husband, socks, frottage
20:08 78%

TranssexualAngel - Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
23:56 78%

Prostate Stimulation

4 years ago

Upornia

prostate, asian, ladyboy
45:23 77%

Big breast shemale Dani Peterson Prostate Penetration

5 years ago

Analdin

stockings, prostate, brazil, big tits, ass licking, babe, erotic
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
25:11 76%

Sissygasm Compilation! Trans Konchaut Bez Ruk Podborka! Prostate Milking

4 years ago

Upornia

prostate, milk, compilation
32:24 75%

Transgender Aubrey Kate Tears Up Puny Lilly Ford

6 years ago

TrannyGem

prostate, massage, nipples, 69, masturbation, shemale
36:18 75%

Introducing You to Anal & Prostate Play

5 years ago

BeMyHole

prostate, solo, jerking, cumshot
17:07 74%

Odor prostate wanking JOI 4K

9 months ago

HDSex

POV, solo, JOI, shemale, masturbation, prostate
21:10 73%

SDHSERIES - Sissy Diaries Day trio

4 years ago

TrannyGem

prostate, orgasm, dildo, BDSM, compilation, orgasm compilation, JOI
36:09 73%

Jyosou Bishonen Prostate Lesson Prostate Lesson Mizuki Yukirin Crossdressing Beautiful Boy

1 year ago

XXXDan

amateur, crossdresser, japanese, beauty, shemale, prostate
35:04 73%

Wonderful tgirl Angel fake penis training

7 months ago

ShemaleMovie

small tits, anal, shemale, prostate, masturbation
15:53 70%

Prostate Massage

8 years ago

ShemaleZ

prostate, massage
24:29 69%

Handsfree And Prostate Cumshots Compilation

4 years ago

Upornia

prostate, compilation, cumshot compilation, hands free, solo
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
24:19 67%

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

9 months ago

TrannyGem

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36:32 67%

Dame college girl pays an influential instructor for humiliation

11 months ago

ShemaleMovie

amateur, homemade, prostate, couple, massage, russian, BDSM
26:41 67%

Prostate cum 23min12sec

6 years ago

ShemaleZ

prostate, cum in mouth
20:03 67%

Hot Sissygasm Prostate Compilation

4 years ago

AShemaleTube

prostate, compilation, cumshot compilation, crossdresser, toys
25:32 67%

Prostate orgasm

6 years ago

xHamster

prostate, orgasm
18:59 67%

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

4 years ago

TrannyGem

prostate, massage, orgasm, chastity, milk
18:29 67%

Pequeño sploog con mi mini bad dragon

4 years ago

TrannyGem

huge dildo, squirt, prostate, orgasm, riding
41:31 67%

Naughty Nurse Checks Patients Prostate Wt Her Massive Cock Indoors

2 years ago

BeMyHole

domination, shemale fucks guy, bareback, prostate, nurse
45:23 64%

Dani Peterson Prostate Penetration

5 years ago

TXXX

prostate, stockings
17:36 61%

French Maid pulverizes ladyboy

6 years ago

HDSex

french, prostate, maid, crossdresser, sissy
1:06:09 61%

Bang The spunk Out Of Him Trans Compilation 1-4

9 months ago

ShemaleTaxi

creampie, prostate, orgasm, creampie compilation, compilation, big cock, cumshot compilation
16:42 60%

Aroma Prostate Milking Joi 4k

3 years ago

ShemaleZ

small cock, prostate, big cock, JOI, solo
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

11 months ago

TrannyGem

amateur, cute, anal, prostate, massage, orgasm, babe
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
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
49:30 57%

Transsexual SWINGERS three - gig 2

1 year ago

ShemaleMovie

skinny, shemale, lingerie, gangbang, prostate, swinger
51:23 57%

Linzy19's Guide To Chastity

3 years ago

xHamster

prostate, fetish, BDSM, domination, JOI, chastity
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
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
25:15 50%

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

10 months ago

TrannyGem

handjob, mature, mature anal, prostate, hairy, milk, shy
28:49 50%

[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
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

2 years ago

TrannyOne

femdom, strapon, doll, prostate, threesome, pegging
29:34 33%

2026 Handsfree Orgasms, Prostate Cumshot Part 3

3 months ago

$$ FapHouse

prostate, orgasm, ass, machine, sissy, hands free
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 )

7 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

1 year ago

XXXVogue

beauty, ebony, feet, shemale, vibrator, prostate
20:05 20%

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

1 year 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
36:20 20%

Nice girl wants to be a strapon mistress and plumb a dude (spanking, first-ever time, comments at the end)

1 year ago

ShemaleMovie

femdom, teen (18+), strapon, prostate, couple, massage, russian
20:04 14%

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

9 months ago

TrannyGem

femdom, prostate, instruction, jerking, anime, futanari, JOI
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
16:16

Fledgling, hd videos, hands free prostate orgasm

2 weeks ago

XXXVogue

shemale, anal, prostate, orgasm, crossdresser, riding, babe
24:16

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

1 week ago

ShemaleMovie

cum in mouth, shemale, cum in ass, orgasm, massage
41:12

2026 Prostate Orgasm Part 5

3 months ago

$$ FapHouse

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

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

4 months ago

ShemaleZ

shemale, shemale fucks guy, doctor, babe, big tits, prostate
21:19

Transgirl Masterbates in Block Shootout

1 week ago

ShemaleMovie

masturbation, orgasm, prostate
16:20

Prostate Milking...

5 years ago

xHamster

latex, prostate, orgasm, milk, anal orgasm
15:37

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

2 months ago

JizzBunker

exam, shemale, anal, doctor, prostate
18:22

Femboy rides plaything dick & cums

3 months ago

ShemaleTaxi

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

Prostate Orgasms Galore - Billie Beaumont

5 months ago

$$ FapHouse

black, anal, prostate, couple, interracial, orgasm, tattoo
20:58

Naomi precum buttfuck pounding

2 months ago

ShemaleMovie

shemale, ebony, dildo, teen (18+), prostate, teen anal (18+)
20:03

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

6 months ago

ShemaleTaxi

prostate, orgasm, japanese, machine, penis, taxi, anal orgasm
2:37:18

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

2 years ago

ShemaleZ

asian, prostate
17:15

Trans Compilation: Prostate Orgasms Galore!

1 year ago

XXXVogue

chinese, orgasm compilation, cumshot compilation, compilation
27:49

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

6 months ago

ShemaleTaxi

shemale, JOI, futanari, POV
15:33

Blonde femboy lingerie cum, forearms free lil cock squirt

7 months ago

ShemaleMovie

crossdresser, russian, dildo, sissy, femboy, prostate
1:08:08

Ultimate Sissy palms Free ejaculation Compilation

11 months ago

ShemaleMovie

sissy, compilation, prostate
31:18

Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie

11 months ago

$$ FapHouse

stockings, french, prostate, massage, redhead, hardcore
22:44

Dildo Precum Milk Prostate

5 years ago

ShemaleZ

prostate, dildo, milk, toys
34:23

Cumshot 30:31 prostate cum 32:15

8 years ago

TXXX

prostate
16:13

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

1 week ago

ShemaleMovie

orgasm, prostate, chastity
16:58

Prostate_play - threesome with orgy girl and iron dildo - pt1

2 months ago

VideoSection

shemale, pantyhose, crossdresser, massage, dildo, prostate
20:50

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

5 months ago

XXXVogue

prostate, orgasm, japanese, dildo, machine
25:15

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

6 months ago

ShemaleMovie

creampie, femboy, dildo, japanese, huge dildo, prostate
22:41

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

8 months ago

TrannyGem

cute, prostate, massage, teen anal (18+), riding, ass, toys
19:59

Wholesome self facial cumshot CEI with futa orc (Expressed reupload+ feral) Chastity feminization Assfuck JOI/

3 years ago

TrannyGem

femdom, prostate, instruction, facial, shemale and girl, futanari, JOI
15:35

Female Dominance cd sissy rectal traning. Fake Penis railing and sissygasm(forearms free-for-all ejaculation)

4 years ago

TrannyGem

femdom, train, prostate, riding, penis, pegging, hands free
15:07

Backside Boned Femboy Shoots A Load Super-Steamy Arms Free-For-All (Opened Up Crevasse Likes)

4 years ago

TrannyGem

train, prostate, hands free, femboy, crossdresser
17:23

He Bangs Flashlight I Pulverizing His Arse.Mary Virgin

4 years ago

TrannyGem

strapon, prostate, wife, pegging, fleshlight
35:35

Lovely Vladasexytrans cam dp and jizz hands free

5 years ago

ShemaleMovie

prostate, russian, teen anal (18+), asshole, gape, hands free, double penetration
23:25

2026 Handsfree Cumshot Prostate Jet. Part 1

3 months ago

$$ FapHouse

amateur, shemale, hands free, prostate
21:08

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

7 months ago

ShemaleTaxi

FTM, prostate, orgasm, creampie
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

9 months ago

ShemaleZ

POV, prostate, asian, orgasm, swallow, erotic, cosplay
15:04

Intense Prostate Milking Orgasm

1 year ago

JizzBunker

couple, shemale, milk
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
41:53

GenderXFilms - Naughty Nurse Checks Patients Prostate wt Her Massive Cock

2 years ago

xHamster

prostate, shemale fucks guy
58:42

Poke the prostate ②　Sayuki-Kana

4 years ago

TXXX

prostate, japanese
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

4 months ago

XXXVogue

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

Flawless ten hook-up Therapist Fucks Her Clients Ass

7 months ago

ShemaleTaxi

feet, strapon, train, prostate, orgasm, facial, babe
16:00

Unboxing The Boogeyman dildo! (Sissygasms & Cumplay)

9 months ago

ShemaleMovie

prostate, orgasm, crossdresser, british, toys, sissy

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