After we (me and my gf) were 2 weeks apart, we started kissing and groping as soon as we could, she started jerking me off and I started massaging her clit And fingered her until she orgasmed. Then she sit on my cock and fucked herself for a while and told me she want me to sit on chair. There she did some naked lapdance for me, until she sit on my cock and rode me again. I was already so close, but wanted to finger her some more, so I moved her on my knee and fingered her, while she grabbed my hard cock, but didnt jerk it, she just hold my cock in her hand, while I fingered her. It didnt took long until I felt her getting close to another orgasm. I fingered her and when she started orgasming, I just cummed with her, only with her hand holding my cock. Út was one of biggest orgasms we ever had together.

Not exactly an expected cumshot but I once masturbated to the 1986 Fender gutiars catalog

Probably too niche a subject for a lot of replies. Everyone's had a classic wank, I can't think of a single unexpected cumshot. Maybe I'm weird.

I had been dating my girlfriend (later wife) for about a month and I was introducing her to my parents. We eventually went into my childhood bedroom and she pushed me onto the bed and started grabbing my cock until I was hard. She undid my pants and started to suck the life out of me. It was nice but I never came from oral before. She kept sucking and stroking like never before and eventually I could feel I was on the edge but figured I wouldn't cum. She took my cock out of her mouth and started stroking me aggressively in a way I didn't expect and told me "What's wrong, never get sucked off in your childhood bed before?" And for whatever reason this sent me over the edge and while my cock was being stroked by her, I came ridiculously hard. I had to shoot off from a laying position at least four feet that my wife went from whispering to almost going cross eyed from following my shot in the air and with surprise saying "W....wow!"

I found a sex video of a girl, that was exactly identical to my wife. I came so much it ended on my computer screen and in my keyboard.

>>953800928
The first time my sister made me cum from grinding. We were in my bedroom while both parents were at work. She was wearing just her underwear and I had just boxers on. She was grinding her vag into my boner while I sucked her nips and pulled her into me. When I busted it felt like I let go of ten ropes into my boxers. There was like a full measuring cup worth of jizz I had to clean up.