I have found a few on Uflash.com (if it is even still up)-- where a guy is jacking in his hotel and maid walks in---and stays to watch. Or is jacking in car and someone stays to watch. Rare, but cool. With the new changes in rules regarding what can be shown, though, might be seeing less of it-- When you think about it, it can be considered a sexual assault---even if the other person stays to watch.
This was a fun one to see.
Favorite - Roommate walks in when he is cumming - ThisVid.com
 
My wife, several girlfriends and a friend that I jerked off and came with a fw times in HS.

Mostly guys from high school. Love showing off how much of my fuckwad i can blast on my pecs and abs and over my shoulder.
 
Some buddies when I was at school, my best bud, I should also add my father walked in on me while I was in the middle of an intense wank no cum but he gave me the birds and bees talk all the while I'm holding my hard dick LMAO
 
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Outside of relationships, a massage therapist. Legit massage, but drape was just a small towel, which was gone well before the end.

When the massage was over, she said, "okay" and when I looked at her, she put her finger on her mouth and said, "shhh."
She rolled back my foreskin, from the tip, gave a few gentle strokes, then she took my hand and put it on me to have me stroke it slowly with her hand over mine to get me going. She let go and stood to the side and watched me finish, doing the "shhh" thing again as I was getting close. She cleaned my chest with tissues after.
 
Outside of relationships, a massage therapist. Legit massage, but drape was just a small towel, which was gone well before the end.

When the massage was over, she said, "okay" and when I looked at her, she put her finger on her mouth and said, "shhh."
She rolled back my foreskin, from the tip, gave a few gentle strokes, then she took my hand and put it on me to have me stroke it slowly with her hand over mine to get me going. She let go and stood to the side and watched me finish, doing the "shhh" thing again as I was getting close. She cleaned my chest with tissues after.

Lol, when I was reading this I was like, "did he go to the same woman?"

Almost exactly the same here. Now in a 120min massage she actually only does 30mins massage and we do 90mins of other stuff.
 
My spouse
My dad
my brothers
a few sports buddies in high school
a few buddies in the navy when we were in the barracks/ship billets
a couple of doctors
a couple of frat brothers in college
a couple of ex-girlfriends


How did a couple of doctors come to see you jerk off and cum??