He tried to pimp me out but now just wants to date me?

So i met this guy and his friend, i figured they looked a bit extreme with tattoos and stuff but it was okay. We went for drinks and i spent the night at his friends place.. no sex. I got a long really well with the friend.

So i got the friends number and he started texting me, next thing i know im being asked if i want to work for him. He told me details of how it worked. I declined and said im not interested.

But lately he started texting me how he misses me and all this lovey stuff.. its been about 8 months since he asked me to work for him.

What should i think of this? Hes asked me a couple times to hang out with him again but i declined.. so..

Is it all him grooming me to try and ask me to work for him again? He knows i have a good job and im not super poor.. im not the stereotype of what youd pick as a girl who would do work like that..