SHEMALE • PROSTATE 1,405 videos

Popular Latest Top rated

13:40 95%

MILF doctor does a great prostate massage and pussy treatment for a cute tranny in her office

2 years ago

AnySex

cute, blowjob, prostate, doctor, massage, MILF, big tits
11:16 94%

Steamy Ass Fucking Climax Compilation of Ultra-Cute Punk Femboy ( Sissygasm Trap Arms Free-For-All )

4 years ago

TrannyGem

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02:01 94%

I cant help it when Ive got a man meat up my bootie

3 years ago

TrannyGem

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01:22 94%

Fembaby pops a big load while getting her prostate pounded

4 years ago

TrannyOne

prostate, asian
03:21 94%

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2 years ago

TrannyGem

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06:23 94%

Im So Close! She Doesnt Even Realise Shes Jism

1 year ago

TrannyGem

squirt, prostate, massage, orgasm, BDSM, milk, machine
05:50 92%

Permitted To Jizz Only From Ass Fucking

1 year ago

TrannyGem

squirt, prostate, massage, orgasm, cuckold, machine, anal orgasm
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

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05:26 92%

Aly gives herself a prostate massage

8 years ago

ShemaleZ

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09:07 91%

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1 year ago

xHamster

pantyhose, stockings, teen (18+), prostate, fetish, orgasm, uniform
04:54 91%

TS doctor examines prostate to patient

5 years ago

BeMyHole

prostate, doctor, gloves, shemale fucks guy
04:27 91%

The Only Way A Sissy Should Be Instructed To Jizz

2 years ago

TrannyGem

prostate, instruction, orgasm, machine, sissy, anal orgasm, hands free
05:21 90%

Sissy rails Monster faux-cock & finishes off Hands Free With Anal Creampie

2 years ago

ShemaleTaxi

feet, huge dildo, orgasm, dildo, monster, hands free
02:01 90%

When youve been edging for too long

4 months ago

TrannyGem

prostate, massage, fetish, orgasm, crossdresser, masturbation, machine
39:58 89%

Ts Dr. Chanel Noir: Home Prostate Exam

3 years ago

ShemaleZ

stockings, prostate, big tits, ass licking, exam
04:24 89%

Underwear dressed in femboy blows a load 3 times in a row

3 years ago

TrannyGem

amateur, homemade, prostate, orgasm, crossdresser, cumshot, masturbation
12:43 89%

Tranny Jenissen Tries New Vibrator Having A Prostate Orgasm

4 years ago

ShemaleZ

prostate, orgasm, solo, vibrator, webcam
07:37 89%

I love opening my ass with my dildo and cumming without touching my dick, uff I had a delicious prostate orgasm

2 years ago

xHamster

beauty, prostate, orgasm, dildo, latina, toys
06:27 89%

Machine Porked Till She Pops In Her Underpants 4K

1 year ago

TrannyGem

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07:06 88%

Variety Itsol In Cums Hard While Milking Her Prostate

2 years ago

ShemaleZ

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25:43 88%

Trans nubile got dual ejaculation with vibro

3 years ago

TrannyGem

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04:40 88%

Fucking Hole!! Mistress Training Prostate Orgasm Compilation

3 years ago

ShemaleZ

stockings, femdom, teen (18+), train, prostate, orgasm, fisting
05:17 88%

Jessica Bloom Ass-Fuck Instructing Innocence Sissy Biotch

1 year ago

TrannyGem

cute, huge dildo, prostate, instruction, massage, orgasm, dildo
36:47 88%

Prostate Exam

1 year ago

AShemaleTube

blowjob, prostate, shemale and girl, cumshot, masturbation, exam
05:51 88%

Chastity Sissy spunkslut Trains Her rectum And swallows Her Own Cum, Multiple Prostate Orgasms

11 months ago

ShemaleMovie

train, prostate, orgasm, fisting, dildo, crossdresser, british
31:30 88%

Compilation shemales cum while anal fuck prostate

3 years ago

TrannyOne

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34:39 88%

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
18:06 88%

Lovely and bad tranny

6 years ago

TrannyGem

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13:02 88%

Trap Having Joy with a Thick Long Cucumber

4 years ago

TrannyGem

huge dildo, prostate, orgasm, hands free
05:14 88%

Prostate climaxes cumpilation. Personalsin bevy vol. 5

2 years ago

ShemaleTaxi

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05:26 87%

Amazing Prostate Orgasms Cumshots Compilation K

2 years ago

ShemaleZ

prostate, orgasm, compilation, toys, cumshot compilation, orgasm compilation
16:24 86%

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

4 years ago

TrannyGem

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13:55 86%

Deutsche dünne teenager amateur transe Celine Dijjon wird ass-fuck gefingert bis zum orgasmus

1 year ago

ShemaleMovie

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05:57 86%

Screwing Her Clamped Honeypot Till She Jizzes Rigid

2 years ago

TrannyGem

prostate, chastity, hands free, massage, insertion
09:55 86%

Prostate Fist Orgasm

4 years ago

HClips

prostate, orgasm, fisting, solo
10:03 86%

Shemale receives asslick and prostate massage

11 years ago

xHamster

femdom, prostate, massage
06:30 86%

Uber-Cute femboy whines while taking a guts vibro

1 year ago

TrannyGem

prostate, femboy
06:27 85%

Powerful Sounding Till She Spunks Rock-Hard

3 years ago

TrannyGem

prostate, massage, hands free
17:07 85%

Odor prostate wanking JOI 4K

4 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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07:08 84%

Variety Itsol Cums Hard While Milking Her Prostate

2 years ago

BeMyHole

feet, cute, prostate, milk, nipples, jerking
05:08 84%

Prostate Orgasms Cumpilation. Personalsin Collection Vol. 88

3 years ago

ShemaleZ

prostate, orgasm, cumshot compilation, orgasm compilation, solo, compilation
09:14 84%

SDHSERIES - Sissy Diaries Day six

4 years ago

TrannyGem

prostate, orgasm, dildo, BDSM, compilation, orgasm compilation, JOI
02:45 84%

Femboy in crimson spectacular gimp costume CUMpilation! Spunk from ass fucking, handballing and soles

1 year ago

TrannyGem

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07:17 83%

Chastity Sissy F Machine Milking - Jessica Bloom jisms no-hands And guzzles Cum

1 year ago

ShemaleMovie

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06:15 83%

Prostate orgasms cumpilation. Personalsin collection vol. 47

5 years ago

AShemaleTube

prostate, orgasm, cumshot compilation
02:04 83%

Blessed sissygasm from mechanical BIG BLACK COCK

9 months ago

TrannyGem

cute, squirt, prostate, big ass, orgasm, milk, crossdresser
11:12 83%

Сolombian prostate cum

8 years ago

AShemaleTube

prostate
07:41 83%

Diversity Itsol spunks stiff while milking her prostate

2 years ago

ShemaleTaxi

feet, small cock, prostate
11:20 83%

Prostate Orgasm For Bf Try No Touch

3 years ago

Upornia

prostate, orgasm
12:22 83%

Shiri Allwood In Tgirl Plugged Femboy Prostate Orgasm And Self-facial On Cam

3 years ago

ShemaleZ

prostate, orgasm, facial, cumshot, femboy
26:05 83%

TRANNY AND HER FIRST-EVER DVP THREEWAY!!

7 months ago

TrannyGem

amateur, mom, shemale, prostate, threesome, massage, chubby
10:41 82%

Sapphic Stepsisters Love to Pound each other in the Bum

4 years ago

TrannyGem

teen (18+), creampie, strapon, lesbian, prostate, russian, teen anal (18+)
07:19 82%

Deep Sounding Into Her Bladder Until She spunks

1 year ago

ShemaleTaxi

orgasm, shemale, insertion, prostate
25:00 82%

Handsfree and prostate cumshots compilation

4 years ago

TrannyOne

prostate, cumshot compilation, hands free, compilation, amateur
06:22 82%

He Cums so Hot during femdom prostate pegging fucking x

3 months ago

TrannyOne

prostate, amateur, shemale, femdom, pegging
20:22 82%

Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
09:38 82%

Small Dicked Shemale Massages Guys Prostate

7 years ago

TrannyGem

small cock, prostate, massage, small tits, shemale fucks guy
06:15 82%

Erica Cherry tries prostate stimulation 2

2 years ago

PornGem

kissing, small cock, prostate
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
27:29 81%

SDHSERIES - Sissy Diaries Day ten

4 years ago

TrannyGem

prostate, orgasm, BDSM, orgasm compilation, JOI, anal orgasm
05:59 81%

Hot Milf And Cum Twice In In A Row Like A Slutty Whore! Ruined Handjob Milking With Prostate Massage!

2 years ago

ShemaleZ

handjob, massage, BDSM, prostate, couple
13:04 81%

Cuteboy Spunk Compilation - 57 gifs, 25 Uber-Cute Femboy Ejaculations

4 years ago

TrannyGem

prostate, orgasm, cumshot compilation, orgasm compilation, skirt, cosplay, femboy
07:06 80%

Her reward For Taking Her Hormones Like a excellent gal

2 months ago

ShemaleTaxi

prostate, massage
06:28 80%

Femboy outdoors nutting with large but cork

4 years ago

TrannyGem

public, prostate, outdoor, orgasm, 18, femboy
10:52 80%

Prostate exam went wrong...

3 years ago

MyLust

prostate, exam
06:00 80%

TS doctor examining a patients prostate

3 years ago

PornGem

prostate, doctor
04:21 80%

Hardcore nonstop Assfucking hard to make me a big load of squirt

2 years ago

xHamster

pissing, stockings, squirt, prostate, orgasm, anal orgasm
06:53 80%

Prostate Bodyrub And Suckjob

3 years ago

ShemaleZ

prostate, ass licking, webcam
09:40 80%

Nano Prostate Toy

3 years ago

ShemaleZ

latex, prostate, asian
11:04 80%

Multiple Prostate Orgasms in Chastity Jessica Bloom Sissy Milking

2 years ago

xHamster

prostate, orgasm, milk, british, chastity
10:05 80%

Girl Fuck Sissy Cumshot Compilation From Prostate Massage Homemade

3 years ago

ShemaleZ

mature, prostate, massage, compilation, cumshot compilation, sissy
15:23 80%

Prostate Massage

6 years ago

ShemaleZ

prostate, massage, tattoo
07:09 80%

Shemale Porn Video Variety Itsol Cums Hard While Milking Her Prostate

1 year ago

TrannyOne

amateur, shemale, prostate, small tits
02:05 80%

乙弯突破

5 months ago

TrannyGem

asian, shemale, teen (18+), orgasm, teen anal (18+)
25:43 79%

Trans teenie got dual climax with electro-hitachi

3 years ago

TrannyGem

prostate, orgasm, double anal, electro, vibrator, double penetration
08:34 79%

Female dom dominatrix fucks bitch sissy ass, double jizz anal orgasm

5 months ago

ShemaleMovie

shemale, strapon, prostate, orgasm, ladyboy, double anal, crossdresser
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
07:38 79%

Icumfromanal - Cum-Shot Compilation

4 months ago

TrannyGem

teen (18+), huge dildo, prostate, massage, fetish, teen anal (18+), orgasm
05:25 79%

Ultimate Prostate Orgasm Compilation: The Filthiest Collection Yet!

2 years ago

AnySex

prostate, orgasm, compilation, erotic, orgasm compilation
01:53 79%

HANDS FREE PROSTATE ORGASM

7 years ago

xHamster

prostate, orgasm, hands free
13:25 79%

Petite young shemale getting fabulous prostate massage

1 year ago

PornLib

shemale, prostate, massage
13:54 79%

Getting Closer to the base of my Seahorse Knob

4 years ago

TrannyGem

huge dildo, prostate, orgasm, dildo, monster, hands free
25:20 79%

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

9 months ago

ShemaleMovie

kissing, shemale, bisexual, prostate, threesome, massage, socks
06:14 78%

TS Dr. Chanel Noir: Home Prostate Exam, Scene #01

4 years ago

TXXX

prostate, exam
10:12 78%

Sissy crossdresser rails a faux-cock ejaculates and gets ass fucking ejaculation (poke tramp culo)

4 years ago

TrannyGem

train, prostate, massage, dildo, solo, sissy, anal orgasm
36:18 78%

Introducing You to Anal & Prostate Play

5 years ago

BeMyHole

prostate, solo, jerking, cumshot
25:09 78%

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

6 years ago

ShemaleZ

prostate, ladyboy
07:04 78%

Kim Carta Pokes A Prostate

11 years ago

xHamster

prostate, black, shemale fucks guy
05:59 78%

Anal Fingering Prostate Orgasm Surprise Cum Shot Coving Her Sex Face & Mouth

3 years ago

ShemaleZ

anal, prostate, orgasm, surprise
05:02 78%

Abby Kitty - Abh052 Elegant Ladyboy In Chastity Prostate Massage And Incontinence Twice 人妖秘书贞操锁前列腺按摩失禁潮吹

4 years ago

ShemaleZ

prostate, massage, chastity
16:20 78%

Milk cow prostate cum

2 years ago

ShemaleZ

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

Prostate Stimulation

3 years ago

Upornia

prostate, asian
08:52 77%

Multiplicity Itsol porks her brains out

2 years ago

TrannyGem

small cock, prostate, massage, fetish, orgasm, milk, shemale and girl
17:07 77%

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

3 years ago

TrannyGem

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45:23 77%

Big breast shemale Dani Peterson Prostate Penetration

5 years ago

Analdin

stockings, prostate, brazil, ass licking, babe, erotic, cum in mouth
07:35 77%

How to have a prostate orgasm

1 year ago

AShemaleTube

amateur, solo, sissy, prostate, femboy
04:45 77%

Self prostate massage makes brain out sissygasm

3 years ago

TrannyOne

prostate, massage
12:42 77%

Poke machine deep rectal teaching and molten jizzing ( femboy sissy trap cd )

4 years ago

TrannyGem

train, prostate, dildo, machine, sissy
02:47 76%

Fuck Machine - Leg Shaking Hands Free Orgasm! Prostate Cum

7 years ago

AShemaleTube

prostate, orgasm, machine, hands free
07:47 76%

Sissyfication Vol.4 by Sonechka25 (instructions on How to Achieve a gal dump for a gal with a Penis).mp4

4 months ago

ShemaleTaxi

amateur, stockings, prostate, instruction, orgasm, dildo, cuckold
10:27 76%

Shemale Cumshot Prostate Compilation

6 years ago

xHamster

teen (18+), prostate, teen anal (18+), compilation, cumshot, masturbation, cumshot compilation
07:28 76%

Asian sissy femboy squirt hands-free multiple time

9 months ago

xHamster

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08:59 76%

Transgirl plow guts ejaculation two

4 years ago

TrannyGem

prostate, orgasm, anal orgasm
05:20 76%

Prostate ejaculations cumpilation. Personalsin bevy vol. 140

2 years ago

VideoSection

homemade, prostate, cumshot, cumshot compilation, shemale, close up
34:36 76%

Prostate compilation

6 years ago

TXXX

prostate, compilation, toys, cumshot compilation
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, ladyboy, compilation, orgasm compilation
06:15 75%

TS Dr. Chanel Noir: Home Prostate Exam, Scene #01

6 months ago

TXXX

big ass, prostate, ass, 18
20:08 75%

TranssexualAngel - Horny Trans Nurse Demonstrates Home Prostate Exam!

4 years ago

TrannyOne

prostate, nurse, exam
10:23 75%

Femboy Deep Rails a Thick Fuck Stick and Loves ( Sissy Trap CD Penetrate TRANSSEXUAL Woman )

4 years ago

TrannyGem

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04:28 75%

Taking It On All 4S Gets Her Every Time

1 year ago

TrannyGem

orgasm, chastity, machine
10:47 75%

Colby Tears Up Lena Kelly

4 years ago

TrannyGem

muscle, prostate, missionary
03:11 75%

Prostate milking and huge cum

7 years ago

TXXX

prostate, milk
07:20 75%

Sissy Femboy In Crimson Running In Rivulets Precum - Railing Massive Black Fucktoy

3 years ago

TrannyGem

pantyhose, train, prostate, crossdresser, insertion, slut, anal orgasm
07:33 75%

JK制服男の娘ピストンマシンに犯されて精液お漏らし #Japanese Crossdresser student gets nailed by bang-out machine

3 years ago

ShemaleTaxi

prostate, student, japanese, machine
08:55 74%

Finest She-Male Sissy Jizm Compilation

9 months ago

TrannyGem

amateur, femdom, prostate, massage, fetish, orgasm, ladyboy
32:24 74%

Transgender Aubrey Kate Tears Up Puny Lilly Ford

6 years ago

TrannyGem

prostate, massage, nipples, 69, masturbation, shemale
12:53 74%

Joey enjoys prostate milking

1 year ago

AShemaleTube

prostate, milk
08:14 74%

Emma Rose - Prostate Exam) By Bbc

3 years ago

ShemaleZ

prostate, exam, BBC

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