Ever cum somewhere you probably shouldnt have?

A couple spring to mind for me.

I was best man in a wedding and had to hang on to the rings for a while. I had a crush on the bride so jerked off using the ring, rubbed it all over my cock and came on it before cleaning it up and giving it back. I would always smile when I saw it on her finger.

I was on a work trip with a female colleague. We were going go out for a walk in the evening but she told me she had forgotten her sunblock. I told her she could use some of mine and I had the opportunity to cum in the top of the tube before I gave it to her. So I got to see her rub my cum into her face and over her arms. I had a raging erection pretty much the whole evening.

Anybody done anything similar?

When we were living with my inlaws I would watch my sis in law in the pool through the bathroom window. I rubbed her toothbrush on my cock and came on it. I washed it off and put it back. I've cum in lots of things!

there has been a few over the years, started early with my sisters panties, I loved them soooo much
on the train - in the main carnage
in my truck
i suppose the place i should not be cuming is in the gf sister

A similar question was asked in another thread so I'll paste my answer across...

I've done this once and I felt kinda bad but it was so so hot. I was in Australia travelling around and staying in hostels. Me and my mate were sharing a room with a few random guys and one super hot girl. We all had to share the same bathroom/shower and I used to love getting a shower after her knowing she'd just been naked where I was stood. I'd always have a wank thinking about it while I showered and one time I was super turned on and I came all over her shampoo bottle (I knew it was hers because she'd asked us not to use it). The thought that she'd pick up her shampoo bottle the next time she got a shower and unknowingly touch my cum was such a turn on. Not done anything like that since but loved it at the time.

Years ago I worked with this hottie who had a bottle of lotion on her desk. One night after everybody went home I jerked off into a condom then emptied it into the bottle. Shook it up to mix my cum into it. It made me so horny to see her using the lotion after that.

When I was a teen I worked with this really bitchy woman but she was kind of hot in a sexy MILF sort of way. One night I was alone and decided to watch some porn and jerk off. I ended up shooting in her coffee cup.

some years back i was fucking the receptionist in our office (back when I actually went to an office sometimes); we'd have sex in the rarely-used office stairwell often but the engineers all took to a 9 hour day schedule with every other Friday off, so I'd come in and we'd fuck in the office, pretty much hit every cubicle thank you very much (small office). First time we had sex in my boss' office i came inside her then took off the condom and carefully wiped cum all over his desk phone (back when ppl had desk phones) using my finger. Not sure if I'll ever scale those heights again but i get a warm feeling remembering it to this day - why's your phone smell funny, GLENN????

A really hot red headed girl was living in an a building just across from my apt. building.Our cars were often parked next to each other. One night I was stroking and went out into the parking lot and squirted my cum all over the door handle of her car. I watched the next morning as she got into her car, so pervy knowing her hand was on my dried spunk.

that would be inappropriate alright especially if your girlfriend found out Haha.

Probably at a 24 hour laundromat at 3:00 am. No one else there, waiting for my clothes to finish in the dryer, so I sat on one of tables, stroked it, and blasted all over the floor and the washing machine in front of me.
Also, just yesterday, I stopped at a local highway plaza, and shot my load all over the wall and floor next to the sink in the bathroom, and left it. I plan on going there and cumming in many spots in that bathroom.

We house and dog sat for my wife's sister a few years back. While the wife was away, I used a one of her sister's thongs to stroke with and came all over that sheer fabric.

The next day, I used my niece's panties.

Washed them and returned them to the respective drawers.