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Why is his needing money a factor he'll be 40 soon. It's not your job to fix his shortcomings, and trust me, this will bite you in the azz It's not exactly prostitution but similar proposition.
yea, any person trying to guilt/manipulate you into having sex is not a person you want to be in a relationship with. he should've respected your no instead of pouting and acting like a child
that behavior would honestly be a deal breaker for me