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I believe this to be the first time. I know he has even gone as far as to blur a girls ass in a thong to make sure not to risk being de-monetized. This is also the first "feature-length" video he has done.
 
I am working on uploading 1080p - I will update this comment with a link when it is done.
I have added a 1080p version to the above link.
 
The current lady in his life is doing a whole lot of slipping this video... guess money's getting tight.

 
Recent "crew". Bobby has a knack for finding crew with porn credentials!

Sarah Lorbeer @sarahlorbr @sarahlr.fit

Jennifer Brown @jenniferbrownakajb

Evellyn Singleton @evsingleton

Katiejo "KJ" Carter @katiejo @kj_persuasion @asianbambichick
 
Can someone find porn those credentials have especially for Sarah and Jennifer?
 
Some girls from Sailing Doodles history this thread has missed:

Chelsea Hagan (left the boat after only a week after partying with friends without Bobby and breaking her arm when a golf cart overturned)
On Only Fans as @sweetcheeks227
https://simpcityopen.com/threads/69999/
https://www.instagram.com/hookd_on_chelz/?hl=en

Nicole aka Coley_jens ex US military who was thrown off the boat by Bobby a few years back in Belize
https://simpcityopen.com/posts/490383/
https://www.instagram.com/coley_jens/?hl=en
On Only Fans and Fansly as @coley_jens

Lauryn Stewart aka Lost_Lauryn, ex sailor, fitness girl and now biker chick who sailed on the electric cat last year in Thailand
https://simpcityopen.com/threads/93378/
https://coomer.st/onlyfans/user/lost_lauryn
https://www.youtube.com/@Lost_Lauryn

Taylor Francis aka Taylor's Travels, Bobby's main squeeze from 5 years ago.
https://www.reddit.com/r/Taylor_Francis/
https://www.instagram.com/taylorfrancis_/?hl=en
https://www.youtube.com/@TaylorsTravels

Willa Prescott aka willavanillaaa, a model who has visited the boat two or three times
https://simpcityopen.com/threads/56080/
 
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