PornTube.Today is your ultimate source for a boundless world of porn video content. Dive into a captivating universe filled with porn sissy prostate milking videos that span a multitude of interests, providing endless hours of entertainment and discovery.

Free XXX sissy prostate milking porn videos - PornTube.Today

12:01

Ass Training – My Fat Ass Bitch Gets Her Cum From My Huge Cock

13:14

First prostate massage for my big ass husband with handjob and moaning. strong orgasm. anal milking. - SweetWetElla

06:14

Milking his cock and fuck boyfrined'_s asshole - huge load cumshot

09:18

Anal Prostate Milking Compilation part 31 - INSTITUTION X

05:29

Milking hot ass femboy with a lot of lub

01:00

Why You Should Try Anal Prostate Stimulation

26:27

Hard sissy training to cum hands free - 4 cumming in 1 sex - FULL video

08:44

Sissy Jackie getting pegged again at (Edgewood Erotica on OF)

01:00

9 Procedures Which Must Be Done To All Boys

05:51

Smoking While Prostate Milking My Sissy – Hard Clit & Asshole

06:00

Hottest cumshot from warmest handjob under mistress

09:53

Anal Prostate Milking Compilation part 33 - INSTITUTION X

04:55

Anal Prostate Milking Compilation part 15 - INSTITUTION X

10:18

In order for the boys to obey, they need to be taught a lesson

01:00

Fucking Machine Prostate Milking 4 Orgasms Hands-free Restrained Femdom

06:24

Slowly Fisting While Hot Cum Drips Out Of Him. Beautiful Prostate Orgasm!!!!

05:32

Eating Hot Sissy's Tight Asshole & Tongue Fucking Her Ass

06:17

Have you dreamed about it? Are you happy now? Your ass says thank you to me!

01:36

Pegging you with my 9 inch strapon. Rough fucking in chastity and a leash. Video 3/6

01:00

30 min endurance anal training

04:39

Anal Prostate Milking Compilation part 17 - INSTITUTION X

01:00

PROSTATE VIBRATOR

14:20

Fan request : Lineaiguille mistress makes femboy cum in chastity cage

12:28

Hottest Anal Pegging he's ever had.

06:40

Milking and prostate massage for hottest chubby femboy

05:00

INSTITUTION X: Anal Prostate Milking Compilation part 6

05:00

INSTITUTION X: Anal Prostate Milking Compilation part 7

15:25

Fingering his hot ass

05:28

Wife Giving Prostate Milking With Sex Toy & Spit Moaning Orgasm

04:41

Prostate Milking Tight Ass With Massive Dildo & Wet Handjob With Massive Cumshot

09:20

Milking his sissy clit, femdom prostate milking, making him drink his own cum

01:02

Anal prostate milking is the only way chastity students are allowed to get a release

06:33

Wife Milks Sissy’s Huge Cock – Making Her Squirt From Anal

03:17

How to cum without hands lesson 3 by Mistress Mary! Full version on my Twitter

05:00

INSTITUTION X: Anal Prostate Milking Compilation part 4

02:18

Sissy Gets Anal Training from DominaFire

11:30

Boy cums twice in a row - Prostate femdom massage double cum

11:23

Prostate Orgasm For Straight Guy

19:17

Prostate Massage Cock Milking Cumshot

01:00

How many times would you be able to beat the clock before you get your cock and balls shocked?

05:18

So much cum!

14:04

Mistress helps sissy slut boy to cum on his face after 7 days abstinence

11:14

Prostate Milking with Epic Moaning Orgasm

13:23

Ass getting DESTROYED

15:23

Pegging, Fisting and Playing with his Prostate until he Shoots His Big Load For Me

03:19

How to cum without hands lesson 3 by Mistress Mary!

01:00

I wonder how much cum will he produce before he starts screaming when he fails to cum every 5 min

06:44

I didn't know it was so nice to be a slut. My ass was trembling after anal orgasm. -NO HANDS-

06:53

I couldn't resist and offered it to a friend, well, look at what a sweet ass.

13:29

Sissy BF CUMS IN HIS OWN MOUTH

04:59

Anal Prostate Milking Compilation part 11 - INSTITUTION X

05:50

What a cute ass, you should be fucked! - Orgasm without hands

01:00

Restrained Doggy Style Torment with Anal Probe. How long would you have to be restrained in this predicament to get your brain rendered and start cumming handsfree from anal alone?

10:39

Fuck this sissy's hole until he cums like a girl

18:58

INSTITUTION X: Anal Prostate Milking Compilation part 01

02:20

10 MIN MAX POWER CHALLENGE - SYBIAN PROSTATE ORGASMS Prostate orgasm overload. Sub Tommy rides Sybian. Multiple prostate orgasms make him moan and shake like crazy. Enjoy the view.

05:00

Anal Prostate Milking Compilation part 25 - INSTITUTION X

06:11

Sissy femboy flows like a bitch from her hands

07:25

Sensual Prostate Massage / Came Inside Myself

06:44

This is what you wanted so much. Your ass is in my power now.

04:42

Anal Prostate Milking Compilation part 19 - INSTITUTION X

08:00

Double orgasm from prostate massage and milking with two cum in a row

11:38

Slowly working my hand in his ass. HIS FIRST FISTING!!!

04:57

Anal Prostate Milking Compilation part 13 - INSTITUTION X

01:00

Goddess Jas makes sub cum multiple times with fucking machine

04:59

INSTITUTION X: Anal Prostate Milking Compilation part 10

01:00

20 MIN RUTHLESS PROSTATE OVERSTIMULATION PROCEDURE

01:10

Poor thing just couldn'_t get over the edge of prostate orgasm from the anal hook alone ...after a week of hard edging torment continues one more weekI bet he soon start begging me to attach him to the fucking machine and end this.

06:13

Wife Eats Sissy Babe’s Ass Out & Fingers Her Prostate

08:07

EDGING JOI WITH KEGEL WEIGHTLIFTING + BONUS - DAY #4

05:08

Anal Prostate Milking Compilation part 22 - INSTITUTION X

21:03

PIG PET (2022, Horror film) - Femdom pegging with fisting,prostate milking and fisting self cum

00:20

She fucks my ass with her dildos and I love it

05:00

INSTITUTION X: Anal Prostate Milking Compilation part 5

01:00

Ruthless Machine Prostate Milking At INSTITUTION X - Everyone can cum from anal

05:00

INSTITUTION X: Anal Prostate Milking Compilation part 9

05:29

Anal Prostate Milking Compilation part 21 - INSTITUTION X

05:04

Anal Prostate Milking Compilation part 23 - INSTITUTION X

07:51

Mistress XXXBat having fun with DKing Gape Plug XL

09:44

Anal Prostate Milking Compilation part 34 - INSTITUTION X

09:33

HUGE CUMSHOTS COMPILATION ONLY - LOT OF CUM

01:00

Anal Training

06:26

I convinced a friend to go for it. Look, he's so happy that I own his hole.

05:06

Nasty Horny Wife Giving Wet Handjob While Prostate Milking With Massive Dildo

15:22

Prostate massage

04:59

Anal Prostate Milking Compilation part 12 - INSTITUTION X

06:25

Milking with finger in femboy ass

10:08

Huge load Cumshot after 7 days without sex from Prostate Massage

07:12

This is what you wanted so much. Your ass is in my power now.

05:00

Anal Prostate Milking Compilation part 26 - INSTITUTION X

01:00

Oh Fuck! Oh Yeah! I love it! Please Dont Stop! More!! More!! Ah! Aaah!! AAAA!!!!! OH MY GOD!

14:58

SHE WILL TEACH YOU TO CUM ANALLY

13:26

Locked Orgasm - Prostate cumshot in chastity belt

03:52

Sissy Anal Examination by DominaFire

05:14

Anal Prostate Milking Compilation part 29 - INSTITUTION X

04:55

Anal Prostate Milking Compilation part 20 - INSTITUTION X

55:00

INSTITUTION X - Prostate Milking Anal Training Pspot Orgasm COMPILATION 1-2

06:32

Mistress milking femboy in fishnet with sex machine

01:00

CUM FROM ANAL EVERY 5 MIN OR GET YOUR COCK AND BALLS ELECTROCUTED

08:54

They always say, "I won't like it.” And then they thank me for the best orgasm. (anal virgins)

Immerse yourself in an extensive porn video library that caters to a wide spectrum of sissy prostate milking genres. Whatever your interests, you'll find it here.