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Late night Oral sex
While I'm in a relationship with my submissive, I do maintain friendships with other boys. We do flirt, but they're respectful, and I considered them both friends.
"Breaking" a submissive means different things to different people. It can mean deep subspace, giving up resistance, emotional catharsis, or extreme breaking that changes people.
I hurt him a little, then sat between his knees, his legs suspended on either side of me. I stroked his cock and teased his hole until he whimpered, until he begged to be fucked.