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If you wanted to do something new sexually with the person you’re seeing/dating would you ask or just go for it and see how they react?

Angiee____
Long story short, My friend has been seeing this guy/dating for a few months and like most people who date, they have gotten to those intimate moments. They were going for it one day and she says originally they were just gonna do it the traditional way and not in the way he ended up doing it. She found herself in a awkward and sort of uncomfortable position when he attempted to penetrate a different hole than usual. She said he didn’t get far in because obviously she noticed the difference in the feeling and had him stop. She said he just laughed/smirked it off and eventually Did it the normal/right way but it’s weird because I thought most guys asked before attempting that.
If you wanted to do something new sexually with the person you’re seeing/dating would you ask or just go for it and see how they react?
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