All time? Has to be the excellent Tiffany Mynx. One of the best cocksuckers ever and a wonderful ass.
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She did a lot of quality work for Elegant Angel in the 90's when she was just starting out, and in the mid 00's made a comeback that I probably prefer to her older work most days. Highly recommend for those of you not familiar!
Recent years: Kendra Spade. From her amateur scenes at NVG and CCHD to her mainstream career, she brought so much energy and passion to her scenes. Always seemed to be genuinely enjoying her self and had the most expressive face. Her scene with Sloan Harper at WLT and with Alina at Girlsway are my favorites.
For her 90's stuff, pretty much anything she did for Patrick Collins at Elegant Angel is top notch and still easy to find. I'm kind of partial to her stuff from Extreme Associates, that was probably her hottest stuff, but there are no digital copies of any of their work, so you'd have to track down DVD's, which are pricey.
Her newer stuff for Jonni Darkko is excellent. Check out Tiffany & Cumpany.
Interesting question. A lot of competition here from stars in different eras: Seka, Veronica Hart, Kay Parker, Loni Sanders, Christy Canyon, Ona Zee, Hyapatia Lee, Taija Rae, Debi Diamond, Nina Hartley, Aurora Snow, Sasha Gray, Tianna, Sharon Mitchell, Amber Lynn, Gauge, Jenna Haze, Dee Williams, Faye Reagan, Stoya, Janet Mason, Jenna Doll, Ruth Blackwell, Hazel Moore and hundreds more.
But I was probably at my horniest in the mid 90s and for an extended period I jerked off a ridiculous number of times to the sumptuous Stephanie Swift!
This question is almost impossible. But in the old days when I only had one VHS tape of porn, it would've been the scene with KC Williams vs Randy West. I jerked off to that scene countless times. It was a compilation porn tape titled "Plastic Fantastic Fuckers". Each scene involved a vibrator. KC Williams was the only lady to take the cum shot in the mouth. Unbelievably cute too.
jst to name a few no particular order but if i had to pick two Shyla Stylez and Ava Addams Shyla Stylez (RIP) Nikki Benz Miss lexa Carmela Bing Abigail Mac Ariella Ferrera Rachel Starr Ava Addams Peta Jensen Julia Ann Cali Carter Brandi Love Rachel RoXXX
There was time when I jerked off to Gianna Michaels a lot, then Audrey Bitoni, Peta Jensen, Keisha Grey, Cali Carter, Mia Malkova and Gabbie Carter etc, but I have no idea who has made me cum the most all time...