Painful First Anal Porn Videos Free Videos Short videos Premium Videos Photos Did you mean painfull first anal? Best Videos 02:35 Sissy cums too early and gets punished with rough fucking 2.1M views 04:12 Selfuking Papiricoo 38.5K views 10:36 Fucking of a Lifetime - Variety Itsol Rodrigo Amor 3.4M views 29:58 Trans Girl plays with an 18 cm Dildo for the first time, Moans from pain but ends up liking it Succubo16 LaRicura16 11.2K views 16:52 3 anal orgasm and hot creampie for skinny trans whore ActorFab 1.9M views 01:28 First try for new plug and a bit bigger Sanne 9.2K views 06:01 I'll fill your asshole with cum to overflowing MrNastyXavier 1.9M views 13:12 Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune Fiona Fortune 218.3K views 04:05 Another straight boy turned by Elizabeth Stewart Elizabeth Stewart 3.1M views 07:53 Painting tranny 656.8K views 03:01 Don't do this to me! I do not like it! 737.3K views 21:53 Hunter boyfriend gave the pain of in the bathroom Redroseromance 2.1M views 05:06 Daddy Milks Trans Girl Prostate Gray Perrier 341.3K views 10:05 Sexy Asian Big Cock Shemale likes to fuck and give pain to big Ass Porn Star Magic Michel deep anal Legacy Mess 101.5K views 03:20 Sissy Cums Too Early And Gets Punished With Rough Fucking. 967.1K views 03:30 Sfmnewbie delicious tasty pussy swallowing huge big giant cock sweet pleasure painful gaping pussy hardcore intense ass thirsty HatanoMiwa 402.7K views 03:06 Shemale Anatomy 2.8M 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 274.9K views 01:05:06 Long Anal Session for Hurting Emma Tied to the Bench ActorFab 271.7K views 36:28 Pain Slut Kira Twistedrama 100.2K views 02:20 When you Don't Want Anymore But Master Still Gives You 981.3K views 04:04 Sfmnewbie delicious and painful intense anal sex hot big ass tasty swallowing big dick anal sweet intense pleasure gaping ass HatanoMiwa 108.1K views 10:03 Can't handle it 140.7K views 16:47 Kitsy - Paddled & caned (a severe spanking in strappado with anal hook) Kitsy Meow 160.8K views 08:12 I Fuck a Beautiful 19-year-old Trans Girl with a Big Dick barbanegrazponto1onepov 2.1M views 01:15:03 Pain and Pleasure Part 2 261.7K views 01:51 Bitch boy can't take her monster cock but she doesn't stop 951.4K 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 00:46 Well almost straight? 446.5K views 51:35 Pain and pleasure, chastity and lust, Part 1 126.2K views 04:08 She fucks him so hard he can't take it, very dominant shemal 310.1K views 03:20 she puts her bikini aside and fucks him in painful doggy 214.8K views 02:20 First timer can't take it at first try, then he takes it all 1.9M views 02:05 Compilation with Weekly Episodes from the pain whore Alina alinanightsky 64.5K views 29:33 Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie Ria_Bentley 2.5M views 02:37 DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM 231.9K views 37:09 Hostel Surprise 3.1M views 01:33 fucking my femboy slave sissy slut painful anal 131.3K views 01:16 Dude takes a tranny painal 169.2K views 02:20 116 min degrading of bdsm sissy pain whore Alina alinanightsky 80.1K views 01:25 Getting fucked for the first time 82.9K views 18:39 Spiked Chastity Cage Torment - Sissy Maids Self Bondage Derek6699 101.1K views 01:14 He Doesn't want to get Fucked Bareback by Her... 876.2K views 17:38 Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots Derek6699 74.9K views 01:57 He Couldn't Handle Her 394.2K views 07:10 Redhead Asian shemale all covered in pain gets fucked Extreme Ladyboys 74.2K views 04:25 travesti amateur 1.7M views Back 1 2 3 4 5 6 ... 80 Next Straight search results Gay search results