Transgender • US
Straight
Gay
Transgender
Videos
Photos
Short videos
Users
Live Sex
Premium
Videos
Pornstars
Channels
Anal Pain Compilation Porn Videos
Free Videos
Short videos
Premium Videos
Photos
HD
Full HD
4K
VR
Best Videos
02:05
Compilation with Weekly Episodes from the pain whore Alina
alinanightsky
65.7K views
02:20
116 min degrading of bdsm sissy pain whore Alina
alinanightsky
80.1K views
13:53
Newest Scene Compilation (with new Stuff) incl. Anal, Gaping, Nipple Pain, Humiliation, Sissy, BDSM, Trans, Denise Humain
Denise Humain
3.4K views
03:41
Fifty Shades of FUCKED UP!! Advance Preview Trailer!!
Cyanide Mistress Of Darkness
10.5K views
07:34
BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
FapHouse
5.8K views
23:11
Denise Humain in bath Final hard self spanking and nipple pain
Denise Humain
8.6K views
08:00
BDSM TS Sissy Slave Rough Sex Compilation - Shemales Fucked Hard with Fetish Toys
FapHouse
6.3K views
35:14
Transsexual
MIMEROMOLE
3.4K views
17:28
Denise Humain Scene Mix (Anal, Nipple, Blowjob)
Denise Humain
4.3K views
02:44
White Stockis and Red Pain Toes
FapHouse
just added
05:12
Wax running in bathtub with thermal imaging camera
Mr_High_Heels_2025
just added
05:00
Sweet Anal Pain for Solo Sissy CD
Regina Blasegern
11.5K views
00:57
cd tranny getting anal pain pounding by fucking machine
Sasha Earth
11.9K views
06:57
Hot CD loves the anal pain she's giving herself by destroying her ass with large dildo(WARNING HOT VIDEO!!)
Dope Slut
3.2K views
01:48
1 Painful Fuck Session. Shemale Big Cock Fuck a Guy, AAIIGRR
975.1K views
13:12
Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
Fiona Fortune
221.7K views
21:53
Hunter boyfriend gave the pain of in the bathroom
Redroseromance
2.2M views
10:05
Sexy Asian Big Cock Shemale likes to fuck and give pain to big Ass Porn Star Magic Michel deep anal
Onlyfans
102.9K views
03:30
Sfmnewbie delicious tasty pussy swallowing huge big giant cock sweet pleasure painful gaping pussy hardcore intense ass thirsty
HatanoMiwa
406.5K views
10:28
Teen Gets Her 1st Painful Screaming Anal But Let Her Finish
101.7K views
10:53
The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
alinanightsky
276.8K views
04:04
Sfmnewbie delicious and painful intense anal sex hot big ass tasty swallowing big dick anal sweet intense pleasure gaping ass
HatanoMiwa
109.2K views
36:28
Pain Slut Kira
FapHouse
101.7K views
01:15:03
Pain and Pleasure Part 2
261.7K views
16:47
Kitsy - Paddled & caned (a severe spanking in strappado with anal hook)
Kitsy Meow
162.3K views
06:08
Tranny Barbie can't take the BBC and tries to get away but he keeps fucking my ass hard - amateur shemale - Candy Ass Sissy
Candy Ass Sissy
66.4K views
51:35
Pain and pleasure, chastity and lust, Part 1
127.2K views
02:37
DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM
233.4K views
01:33
fucking my femboy slave sissy slut painful anal
132.1K views
18:39
Spiked Chastity Cage Torment - Sissy Maids Self Bondage
Derek6699
102.2K views
17:38
Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots
Derek6699
74.9K views
07:10
Redhead Asian shemale all covered in pain gets fucked
Extreme Ladyboys
74.2K views
03:04
25 min of abuse and hard use for the pain whore Alina
alinanightsky
53.9K views
02:55
The sissy pain whore Alina show her skills in self-humiliation and deep throating with dildo
alinanightsky
28.9K views
18:18
Anal fist fuck faggot love to feel the pain in the ass
Nicole Montero
144.3K views
16:17
some fun kitty playtime
Kittykisses96
21.3K views
06:06
My patient was complaining of pain in his leg, so I treated him to butt tea at my office desk
Nathalia Fontes
112.6K views
17:02
Thick Anal Viring Gets Her 1st Time Very PAinful & Begging
59.2K views
01:34
A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
alinanightsky
41.7K views
14:26
Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
FapHouse
43.1K views
08:37
Black blow up spiked butt plug for my S&M Daddies!
Victoria Lecherri
44.1K views
07:30
Redhead asian trans all covered in pain ass fucked
Extreme Ladyboys
15.8K views
10:11
Extreme Anal Insertion Two Foot Long XXL Anal Slink
Onlyfans
45.6K views
07:15
School Uniform Painful Dragon Dildo Fuck
PrincessKitti3
470 views
01:04
Up Close Painful Femboy Dildo Practice
Khatara Shikiku
6.1K views
06:12
Young Goth Trans Does Painful Anal
Khatara Shikiku
9.2K views
51:35
Pain and Pleasure
91.2K views
Next page
1
2
3
4
5
6
...
41
...
80
80
Searches Related to Anal Pain Compilation
Painful Anal Sex
Ass Fingering Compilation
Three Minutes of Anal Hell
Trap Compilation
In English
Dildo Compilations
Ex Hamster
Cd Orgy Group
An Endless Masterpiece Part 1
Fucking Very Very Hard
My Anal Sex
Extreme Sissy
Doctor's Office
Big Cock Pain
Fuck Machine Cams
2 Minute Stress Reliever
Puckering Asshole Orgasm
A Guide to Sissification Beginner
Traps Compilation
Shemale Doggystyle View From Bottom
Straight search results
Gay search results