SHEMALE • PROSTATE 305 videos

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34:39 92%

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

2 years ago

ShemaleZ

stockings, small cock, prostate, big tits, blonde, cum in mouth, small tits
17:26 90%

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

5 years ago

ShemaleZ

huge dildo, prostate, orgasm, dildo, redhead, 18, toys
16:30 90%

Prostate jerking...

5 years ago

ShemaleTaxi

latex, prostate, taxi, jerking
16:20 89%

Milk cow prostate cum

3 years ago

ShemaleZ

prostate, milk, selfsuck, crossdresser
39:58 89%

Ts Dr. Chanel Noir: Home Prostate Exam

4 years ago

ShemaleZ

stockings, prostate, big tits, ass licking, exam
36:47 89%

Prostate Exam

2 years ago

AShemaleTube

blowjob, prostate, shemale and girl, cumshot, masturbation, exam
21:07 88%

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
18:06 88%

Lovely and bad tranny

7 years ago

TrannyGem

prostate, orgasm, redhead, masturbation, reality, vibrator, hands free
18:22 88%

Femboy rides plaything dick & cums

8 months ago

ShemaleTaxi

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25:00 86%

Handsfree and prostate cumshots compilation

4 years ago

TrannyOne

prostate, cumshot compilation, hands free, compilation, amateur
25:43 86%

Trans nubile got dual ejaculation with vibro

4 years ago

TrannyGem

teen (18+), prostate, teen anal (18+), orgasm, latina, double anal, vibrator
27:29 83%

SDHSERIES - Sissy Diaries Day ten

5 years ago

TrannyGem

prostate, orgasm, BDSM, orgasm compilation, small tits, JOI, sissy
31:30 83%

Compilation shemales cum while anal fuck prostate

4 years ago

TrannyOne

prostate, 18, creampie compilation, compilation, cum while fucked
25:09 83%

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

7 years ago

ShemaleZ

prostate, ladyboy
22:41 83%

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

1 year ago

TrannyGem

cute, prostate, massage, teen anal (18+), riding, ass, hands free
26:05 83%

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

3 years ago

TrannyGem

mom, shemale, prostate, massage, chubby, wife, MILF
26:05 82%

TRANNY AND HER FIRST-EVER DVP THREEWAY!!

1 year ago

TrannyGem

amateur, mom, shemale, prostate, threesome, massage, chubby
36:48 82%

Prostate Epiphany With Erica Cherry And Whitney Wright

2 years ago

ShemaleZ

shemale, prostate
15:23 82%

Prostate Massage

6 years ago

ShemaleZ

prostate, massage, tattoo
34:36 81%

Prostate compilation

7 years ago

TXXX

prostate, compilation, toys, cumshot compilation
16:24 81%

Uber-cute massive chubby donk she-male shoots a load while porked by a random XXL meaty man rod

5 years ago

TrannyGem

cute, anal, prostate, chubby, orgasm, anal orgasm, cum while fucked
25:20 81%

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

1 year ago

ShemaleMovie

kissing, bisexual, prostate, threesome, massage, socks, frottage
20:22 81%

Horny Trans Nurse Demonstrates Home Prostate Exam!

5 years ago

TrannyOne

prostate, nurse, exam
25:43 81%

Trans teenie got dual climax with electro-hitachi

4 years ago

TrannyGem

prostate, orgasm, double anal, electro, vibrator, double penetration
36:18 80%

Introducing You to Anal & Prostate Play

6 years ago

BeMyHole

prostate, solo, jerking, cumshot
26:06 80%

TRANSGIRL AND HER first DVP three-way!!

1 year ago

ShemaleMovie

prostate, threesome, massage, husband, socks, frottage
22:37 80%

Adorable trap femboy climaxes forearms free-for-all from petting mighty wand ( sissy instructing )

4 years ago

TrannyGem

prostate, instruction, massage, russian, orgasm, milk, close up
1:57:08 80%

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

3 years ago

ShemaleZ

prostate, asian
23:56 80%

Prostate Stimulation

4 years ago

Upornia

prostate, asian, ladyboy
15:35 80%

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
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 78%

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

4 years ago

TrannyGem

prostate, massage, fetish, orgasm, milk, babe, chastity
20:08 78%

TranssexualAngel - Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
25:11 78%

Sissygasm Compilation! Trans Konchaut Bez Ruk Podborka! Prostate Milking

4 years ago

Upornia

prostate, milk, compilation
45:23 78%

Big breast shemale Dani Peterson Prostate Penetration

6 years ago

Analdin

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21:10 77%

SDHSERIES - Sissy Diaries Day trio

4 years ago

TrannyGem

prostate, orgasm, dildo, BDSM, compilation, orgasm compilation, JOI
19:15 76%

Hands Free Cum with huge Mr Hankeys Cody Cachet dildo

1 year ago

xHamster

huge dildo, anal, prostate, dildo, lingerie, riding, ass
17:07 76%

Odor prostate wanking JOI 4K

1 year ago

HDSex

POV, solo, JOI, shemale, masturbation, prostate
35:04 75%

Wonderful tgirl Angel fake penis training

1 year ago

ShemaleMovie

small tits, anal, shemale, prostate, masturbation, train
17:07 75%

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

4 years ago

TrannyGem

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32:24 74%

Transgender Aubrey Kate Tears Up Puny Lilly Ford

7 years ago

TrannyGem

handjob, prostate, massage, nipples, masturbation, 69
24:29 72%

Handsfree And Prostate Cumshots Compilation

4 years ago

Upornia

stockings, prostate, compilation, cumshot compilation, hands free
18:29 71%

Pequeño sploog con mi mini bad dragon

4 years ago

TrannyGem

huge dildo, squirt, prostate, orgasm, riding
53:00 71%

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

6 years ago

TrannyGem

prostate, orgasm, machine, orgasm compilation, femboy
36:09 71%

Jyosou Bishonen Prostate Lesson Prostate Lesson Mizuki Yukirin Crossdressing Beautiful Boy

1 year ago

XXXDan

amateur, crossdresser, japanese, beauty, shemale, prostate
26:41 70%

Prostate cum 23min12sec

6 years ago

ShemaleZ

prostate, cum in mouth
15:53 70%

Prostate Massage

8 years ago

ShemaleZ

prostate, massage
16:16 67%

Fledgling, hd videos, hands free prostate orgasm

6 months ago

XXXVogue

anal, prostate, orgasm, riding, sissy, hands free
36:32 67%

Dame college girl pays an influential instructor for humiliation

1 year ago

ShemaleMovie

homemade, prostate, couple, massage, russian, BDSM, ass
41:31 67%

Naughty Nurse Checks Patients Prostate Wt Her Massive Cock Indoors

3 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
16:41 67%

Sissy Slut Bess wrecks her boipussy with beer bottle before squirting a massive load

3 years ago

xHamster

squirt, cumshot, sissy, anal orgasm, prostate, bottle
21:13 64%

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
1:06:09 64%

Bang The spunk Out Of Him Trans Compilation 1-4

1 year ago

ShemaleTaxi

creampie, prostate, orgasm, creampie compilation, compilation, cumshot compilation, orgasm compilation
28:49 64%

[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
16:42 63%

Aroma Prostate Milking Joi 4k

3 years ago

ShemaleZ

small cock, prostate, big cock, JOI, solo
45:23 63%

Dani Peterson Prostate Penetration

5 years ago

TXXX

prostate, stockings
20:03 60%

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

11 months ago

ShemaleTaxi

prostate, orgasm, japanese, machine, penis, taxi, anal orgasm
27:30 60%

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, femboy, crossdresser
24:14 60%

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

1 year ago

TrannyGem

cute, anal, prostate, massage, orgasm, ass, cum in mouth
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 )

5 years ago

TrannyGem

prostate, massage, teen anal (18+), close up, sissy, femboy
17:36 58%

French Maid pulverizes ladyboy

7 years ago

HDSex

french, prostate, maid, crossdresser, sissy
19:04 58%

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

5 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
25:32 57%

Prostate orgasm

6 years ago

xHamster

prostate, 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
18:53 56%

Female dominance IDEAS - TOP 10 bonus

4 months ago

HDSex

handjob, shemale, train, prostate, orgasm, BDSM, 18
24:19 56%

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

1 year ago

TrannyGem

mom, femdom, strapon, huge dildo, prostate, orgasm, fisting
2:17:13 56%

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

2 years ago

ShemaleZ

shemale, asian, prostate, stockings, squirt, lingerie
23:24 55%

Femboy Sorority - Ep 2 (Petite Femboy Prostate Orgasm)

3 months ago

AShemaleTube

anal, prostate, orgasm, sissy, femboy
18:49 53%

Miruku Aima Prostate Squirt Sex

9 years ago

xHamster

squirt, prostate, ladyboy
31:39 53%

Compilation t-girls jizm while anal smash prostate

6 years ago

VideoSection

creampie, prostate, creampie compilation
18:53 50%

Role-play, post-orgasm, female dominance

2 months ago

XXXVogue

handjob, shemale, train, prostate, orgasm, BDSM, compilation
51:27 50%

SweetandHot buttfuck & (pre)cumshow

1 year ago

ShemaleMovie

shemale, femboy, orgasm, big tits, masturbation, prostate
34:36 50%

Prostate compilation

7 years ago

ShemaleZ

prostate, compilation, cumshot, cumshot compilation
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
31:30 42%

Compilation shemales cum while anal fuck prostate

8 years ago

TXXX

prostate, creampie compilation, compilation, cum while fucked, masturbation
15:36 40%

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

10 months ago

ShemaleZ

prostate, doctor, big tits, babe, exam
20:20 40%

Japanese Crossdresser college girl gets pummeled by orgy machine

1 year ago

ShemaleMovie

anal, orgy, prostate, crossdresser, machine
54:13 38%

Naomi, the sexy trans girl, indulges in passionate anal pounding

1 year ago

XXXVogue

prostate, orgasm, femboy, shemale and girl, dildo
25:15 33%

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

1 year ago

TrannyGem

handjob, mature, mature anal, prostate, hairy, milk, shy
29:34 29%

2026 Handsfree Orgasms, Prostate Cumshot Part 3

8 months ago

$$ FapHouse

prostate, orgasm, ass, machine, sissy, hands free
1:53:43 25%

Compilation of deep ass-fuck penetrations ( sissy trap femboy anal riding )

1 year ago

ShemaleMovie

prostate, russian, dildo, compilation, riding, ass, toys
20:04 25%

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

1 year ago

TrannyGem

femdom, prostate, instruction, jerking, anime, futanari, JOI
24:24 20%

How to make a good erotic video

2 years ago

xHamster

mature, prostate, orgasm, mexican, anal orgasm, hands free
19:59 20%

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

4 years ago

TrannyGem

femdom, creampie, prostate, instruction, facial, shemale and girl, futanari
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
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
20:05 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
21:53 20%

[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

prostate, massage, orgasm, sissy, anal orgasm, cosplay, japanese massage
28:30 10%

Can You Treat Your Keyholders Gifts? - Ass-Fuck Have Fun, Feminization, Purity Praise RP

2 years ago

TrannyGem

mom, femdom, prostate, dildo, 18, cartoon, chastity
41:12

2026 Prostate Orgasm Part 5

8 months ago

$$ FapHouse

prostate, orgasm, masturbation, ass, machine, sissy
15:04

Intense Prostate Milking Orgasm

1 year ago

JizzBunker

couple, shemale, milk, prostate
22:22

Prostate Orgasms Galore - Billie Beaumont

10 months ago

$$ FapHouse

black, anal, prostate, couple, interracial, orgasm, tattoo
20:22

Sexy Excited Trans Nurse Shows Home Prostate Exam!

3 years ago

TrannyOne

prostate, nurse, exam
16:13

Anal orgasms, unexperienced, shemale hands free cum

4 weeks ago

XXXVogue

stockings, prostate, orgasm, lingerie, heels, anal orgasm, hands free
20:50

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

11 months ago

XXXVogue

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

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

12 months ago

ShemaleMovie

creampie, femboy, dildo, japanese, huge dildo, prostate
16:28

Prostate orgasms cumpilation. Personalsin collection vol. 157

5 months ago

AShemaleTube

shemale, cumshot compilation, orgasm, prostate
17:15

Trans Compilation: Prostate Orgasms Galore!

1 year ago

XXXVogue

chinese, orgasm compilation, cumshot compilation, compilation
34:23

TSCHX Cumshot 30:31 & Prostate Cum 32:15

9 years ago

xHamster

prostate
15:25

Sort Of BEHIND-THE-SCENES - Sissy Lucy Ass Fucking Pounding On The Boning Machine

2 years ago

TrannyGem

behind the scenes, anal orgasm, mature
20:52

Pink outfit femboy red lipstick 20 minutes of prostate play - numerous postures no forearm cum

2 weeks ago

ShemaleTaxi

orgasm, femboy, amateur, dildo, massage, prostate
37:37

Prostate Play Rides Dildo in Hardcore Trans Sex Doll Fuck

1 month ago

JizzBunker

amateur, crossdresser, dildo, shemale, prostate, doll
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, prostitute, toys, tight, femboy
31:18

Spanking Gorgeous Trans Balls, and Hardcore Prostate Massage + Creampie

1 year ago

$$ FapHouse

stockings, french, prostate, massage, redhead, hardcore
20:58

Naomi precum buttfuck pounding

8 months ago

ShemaleMovie

shemale, ebony, dildo, teen (18+), prostate, teen anal (18+)
27:59

My best Friends mother is a Futa - vignette 2 [Anal Exploration, Blowjob Training, Oral Creampie JOI]

1 year ago

ShemaleMovie

JOI, massage, futanari, dildo, prostate, train
1:08:08

Ultimate Sissy palms Free ejaculation Compilation

1 year ago

ShemaleMovie

sissy, compilation, prostate
20:22

Miyuki masturbation

2 years ago

xHamster

asian, hands free, prostate
26:32

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

6 years ago

TrannyGem

prostate, teen anal (18+), cum in ass
20:13

Steaming Sissygasm prostate Compilation

3 months ago

ShemaleMovie

compilation, cumshot compilation, crossdresser, amateur, prostate
30:57

Training for early climax with ShibbySays JOI featuring pierced tgirl Itsol and anal toys

11 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

1 year ago

ShemaleZ

prostate, orgasm, swallow, erotic, cosplay
20:22

Chanel Noir In Horny Trans Nurse Demonstrates Home Prostate Exam!

5 years ago

ShemaleZ

prostate, nurse, big tits, ass licking, exam, big cock
20:59

The ladyboy That Takes It In The Fanny - gig 1

5 years ago

ShemaleTaxi

public, voyeur, prostate, nylon, hardcore, asian
16:20

Prostate Milking...

5 years ago

xHamster

latex, prostate, orgasm, milk, anal orgasm

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