my mom has caught me couple times-- and then she caught me one time doing something else i can not say in this chat as it is ask a straight man but if wanna know and its ok with originator of this question ill say it--if not then private is cool--have a great day
 
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Every girlfriend, boyfriend, random hook-up, the teenage guy along the road when I was a student, various folks in toilets / cruising grounds.
 
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How did her boss see you jerking off...?
A girlfriend, her friends, and her male boss. Members of a drawing group. A photographer. Attendees at various parties. A fuck buddy.
 
How did her boss see you jerking off...?
I’d go out with my GF and a few of her work friends and he’d join us so he got to be regular one of the group. Got invited to a pool party at his house. Late into the party GF mentions I modeled for drawing parties. Some of the guests dared me to get naked so I did. Later GF and two friends (fairly drunk by that time) kept asking me do a jerk show for them. We went around the side of the house where there was an outside shower. I started my show in the shower then moved over to a kind of outdoor recliner-bed. A few other guests and her boss wandered over and stayed to watch. Major turn on being shown off to GF’s coworkers. Huge splashy climax.