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Answer (1 of 6): The biggest cumshot for me was probably when me and my girlfriend were masturbating together (she lives long distance at this moment in time so we usually sext) but yeah, at the time she was rubbing her pussy and thrusting her fingers in and out for me which led her to orgasming.
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Biggest cumshot, as in most volume of cum, was with the girl whom I dated for nearly 6 years. It was one of the first times we tried bondage. I had her tied to the bed in doggy position. She was screaming, saying dirty things, telling me to use her like a fuck toy, etc. It was hot. When the time came, I pulled out and came all over her back.
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