Transgender • US
Straight
Gay
Transgender
Videos
Photos
Short videos
Users
Live Sex
Premium
Videos
Pornstars
Channels
Short Painful Penetration Porn Videos
1295 Results
Free Videos
Short videos
Premium Videos
Photos
Linda asian ts pain with champagne and big dildo. (sample)
Lindaasian-ts
7.8K views
Key moment from "Hunter boyfriend gave the pain of in the bathroom"
Redroseromance
11.1K views
Pressing a giant plug out of my anus
Charlotte Wilde
4.5K views
FUCKING MY HOLE WITH A BOTTLE
youngtightcutie
2.2K views
Slut cd using stiging nettles.
Amy-leigh8969
2.6K views
Emotional moment from "How to Give Pain and Pleasure to a Big Sissy Cock"
MyLolaTrav
697 views
School Uniform Painful Dragon Dildo Fuck
FapHouse
720 views
pain and pleasure desire to be in pain
Alexia_mtf
197 views
Memorable moment from "Hunter boyfriend gave the pain of in the bathroom"
Redroseromance
1.1K views
Ifetfuc chastity devices and ball stretching toys. Humiliation as he is turned to a sissy for mistress. Painful.
iFetFuc
3.6K views
More pain on my account
FapHouse
1.2K views
Thrilling moment from "A sissy tortures her buttocks severely with nettles, ties up her balls, dildoes herself and makes herself cum with the vibrator"
MyLolaTrav
443 views
Captivating moment from "some fun kitty playtime"
Kittykisses96
630 views
Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes! | Clip 1
Denise Humain
690 views
Emotional moment from "How to torture a beautiful sissy cock"
MyLolaTrav
413 views
Sissy Denise: Nipple torture with combination pliers – Live until the end | Clip 1
Denise Humain
263 views
Epic moment from "Working on Sissy Slave Denise Humain Nipples for hours Part 1"
Denise Humain
696 views
Must-share moment from "Painful Anal Stretching With Facial"
Chantal Fouet
409 views
Memorable moment from "Painful Anal Stretching With Facial"
Chantal Fouet
544 views
A naughty housemaid with ripped black pantyhose tried the thickest dildo into her sissy pussy and moaned with pain and joy | Clip 1
Harinni
207 views
A naughty housemaid with ripped black pantyhose tried the thickest dildo into her sissy pussy and moaned with pain and joy | Clip 2
Harinni
230 views
Thrilling moment from "Working on Sissy Slave Denise Humain Nipples for hours Part 1"
Denise Humain
665 views
Iconic moment from "Working on Sissy Slave Denise Humain Nipples for hours Part 1"
Denise Humain
847 views
Beautiful sissy pleasures herself with nipple clamps, nettles and a dildo, then makes herself cum with her vibrator | Clip 1
MyLolaTrav
295 views
Sissy Denise: Tied Nipples Tortured with Rough Round Brushes | Clip 3
Denise Humain
just added
Stunning moment from "Painful Anal Stretching With Facial"
Chantal Fouet
375 views
Spectacular moment from "FtM boy punished for being lazy"
479 views
Epic moment from "Plugged sissy, nipple clamps, caged dick whips her ass and cock with nettles before making herself cum with the vibro"
MyLolaTrav
509 views
Spectacular moment from "Plugged sissy, nipple clamps, caged dick whips her ass and cock with nettles before making herself cum with the vibro"
MyLolaTrav
372 views
Unforgettable moment from "Urethral sounding and vibration of a caged and bound shemale"
MyLolaTrav
385 views
Epic moment from "BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys"
Denise Humain
492 views
Sissy Denise: Tied Nipples Tortured with Rough Round Brushes | Clip 2
Denise Humain
71 views
Pathetic Maid Apology Riding Crop Self Punishment | Clip 2
FapHouse
107 views
Must-share moment from "Sissy with nipple clamps ties up her cock and makes herself cum hard with the vibrator"
MyLolaTrav
326 views
Sissy Denise: Tied Nipples Tortured with Rough Round Brushes | Clip 1
Denise Humain
73 views
Must-share moment from "How a Tgirl severely punishs her big cock."
MyLolaTrav
319 views
Emotional moment from "BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys"
Denise Humain
629 views
Unforgettable moment from "Hunter boyfriend gave the pain of in the bathroom"
Redroseromance
671 views
Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes! | Clip 2
Denise Humain
320 views
Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes! | Clip 3
Denise Humain
442 views
Epic moment from "How a Tgirl severely punishs her big cock."
MyLolaTrav
464 views
Spectacular moment from "How a Tgirl severely punishs her big cock."
MyLolaTrav
400 views
Powerful moment from "How to Give Pain and Pleasure to a Big Sissy Cock"
MyLolaTrav
405 views
Pathetic Maid Apology Riding Crop Self Punishment | Clip 1
FapHouse
98 views
Newest Scene Compilation (with new Stuff) incl. Anal, Gaping, Nipple Pain, Humiliation, Sissy, BDSM, Trans, Denise Humain | Clip 1
Denise Humain
292 views
White Stockis and Red Pain Toes
FapHouse
123 views
Ts kamayiabrooks 11in BBC TRANNY COCK
KarleyMilani
392.3K views
DOUBLE DILDO in MY HOLES
Lola Spais
50.7K views
Next page
1
2
3
4
5
6
...
14
...
27
27
Searches Related to Painful Penetration
Extreme Insertion
First Time Painful Anal
Brutal BBC Fucks CD
Post Orgasm Torture
Accidental Cum in Mouth
Amateur Painal Homemade
Hardcore Rough Sex
Uncut Shemale Cock
Please Stop
Relentless Pounding
Begging for Creampie
Double Penetration
Dick Too Big
Rectal Prolapse
Extremely Large Penis
Uncensored
Black Boy Screams
No Mercy
Sissy Crying
Huge Insertions
Straight search results
Gay search results