A classic!
Xtasis - Panochitas

TRISTAN KINGSLEY VS RAMON

12:20 initial penetration, great shot of the super tight fit and facial expression looks real, she runs for 40 seconds, lots of exasperations 13:00 a deep stroke, 13:06 real deep she is "Hold On, just hold on one second", I think he is legit opening her up 13:10 he splits her in two and at 13:36 tries to bury it. She is grimacing 13:27 "You have to go a little bit softer" 14:27 he starts pounding almost balls deep, 14:35 "wait. wait, wait" 14:30 he pounds her, great contortions in her face 16:40 she say's it is hurting!

Emma Stoned vs. Bruce Venture Couldn't find a thread here but
MOD EDIT: BROKEN LINK REMOVED

Mini Stalllion vs Damion Dayski, one of the few videos where Mini Stallion actually struggles and flinches, complaining the dick is too big.
Video Link Mini Stallion's Onlyfans

Katerina Kay

Shane Diesel w/ hotwife Anyaxo (orig shared here) Trying to enter she keeps saying "ow", he tries a few times, finally suggests maybe they do a jerk off scene instead. Tries one more time and gets in. Lots of wincing face and she doesn't look comfortable until about halfway. By the end seems relieved scene over.
h265

Sawyer Cassidy with Brickzilla

another one of sawyer cassidy with brickzilla
https://simpcity.su/threads/sawyer-cassidy-sawyercassidy3x.211078/

Tiffany Rayne comes to mind. (no thread) Had to quickly search her up but this was the vid where she struggles with both BBCs the whole vid.
Some timestamps below 9:18 12:40 15:10 16:10

Kylie Richards and Shane Diesel. In an interview she said: "It hurt so bad. I was crying during the scene. After that, I quit porn. I started working as a sales rep at a normal company. I was like no more of that shit. I'm done."
Kylie Richards quits porn

Tia Tanaka - Beaver hunt #3
Around 16:30 subtitles say she couldn't handle the pounding so they finished the scene with a blowjob

erica fontes

Miss_dxxx & girthmasterr

Kit Mercer - Black Ambush
Victoria Hobbs - HotGuysFuck

Danika aka Cort Suicide (Re-up recovery since the crash of ’24)
Gloryholeswallow 1st scene
38:40 - In the Post interview she claims never being with a black guy before, let alone a stranger. First he tries to get it in while in standing doggy, no luck and she laughs "Tight fit" and he agrees and continues trying to fitting it in from behind. 58:26 - A new BBC shows up BJ then he is invited into the booth. 59:49 - She on all fours, he's in immediately - "Oh Fuck", he asks "you alright?", when she says "yeah" he bottoms making her yelp out. 1:00:00 - This guy doesnt fuck around and tells her to spread her knees, not the first time shes been submissive I'm sure, then begins to pound her out from behind 1:00:25 - "You're really deep" "That's what you asked for right?", Pounds the shit out of her for the next 24 mins. Gloryholeswallow 3rd Scene
12:55 - Danika agrees to be strapped down to a bench so she cant "wriggle away", safe word is Pineapple. 15:50 - First BBC enters from behind and she's spit roasted. 16:00 - We can hear her discomfort even though her mouth is full. He's thick, long and that GRIP, wow. He plays with her ass, fingers it and continues to drill her from behind for a few mins. The guys using her mouth switch out. 19:24 - "PINEAPPLE" Safe word used. he slows down, doenst stop and presses in the whole way. "oh god that's going in deep" 23:27 - BBC's switch out, this guy isnt as big, but makes up for it with enthusiasm. 26:16 - While still strapped down she takes the new BBC in her ass. She reaches back to grip his wrist obvious discomfort. 26:48 - "Oh god" she pushes him away, hand behind her pushing on his hip. 27:00 - "We need to stretch it out more first, sorry, i'm just a tight fit" 30:40 - A new cock has been using her pussy with a butt plug in her ass. Time for the cock, "Just be gentle" she begs. 30:50 - Anal 2nd attempt "Ow" she's a trooper, legs are shaking...she takes another anal break and the butt plug is returned. more fucking ensues. 44:35 - She's unstrapped by now, standing and another BBC tries her again from behind. Enjoy