Who did you first jerk off for in person?

For me it was for a 63y/o woman I had chatted to online when I was in my late 20’s. She had never watch a man jerk off, not even her husband. I suppose she was of an age that considered such things ‘dirty’.

We arranged to meet up during her lunch break one day. After picking her up, we drove to a park she knew off and we just sat in my car, windows steaming up, as she watched me stroke off for her until I came, strongly, in my hand.

Very erotic occasion for us both.
For her because she watched a guy younger than her sons jerk off and cum for her during a lunch break, after which she’d have to go back to work wet and horny.
For me, because it was the first time in front of a woman, who half way through my stroking session decided she’d masturbate herself as she watched me stroke off , and then grabbed my hand to lick up my cum when I’d finished.

She’d be in her 80’s now. I wonder sometimes if she’d ever like to watch me again, for old times sake.

it was an old guy in toilets when I was very young I got caught looking at a dirty mag I found

My mom. I was jerkin with my eyes closed, when I opened them my mom was standing over me watching. I was to far gone to stop and just kept on until completion.

I don't think he means who caught you guys but who actually sat and watched. for me it was my cousin.

My wife on many occasions.She got a kick watching me as I shot my wad.

my mom lol

It was my best friend which was my neighbor buddy also. I was 12 and he was 13. We had many good times together.

it was a high school friend. we used to hang out after school and we got into jerking off together.

My younger brother was the first person to watch me jerk off.

My best friend in jr. high school. I was the first to watch him as well.

My friend from junior school, we used to go back to his after school before his parents came home and stand in front of each other masturbating........

Wow that sounds very hot!! PM me

i used to love to wank with old guys in the toilets when I was young, but first time was with my mates

3 female friends, back when I was in high school.

college roommate