I was 18 or 19, slightly chubby, bottom heavy, starting community college while living with my mother. She was a traditional minimum wage worker who didn't enter the workforce until my dad died when I was 16ish. We are renting a guy's second home and he was over explaining that he's going to have to evict us if we kept missing payments. During the conversation my grindr notification sounds. Mom didn't know the sound but he certainly did as he was eyeball fucking me the rest of the time. As soon as he goes back out to his car he messages me and explains he would put us back to zero if I play with him. He wasn't exactly handsome but he was far from ugly and in decent shape. I said yes and he picked me up from college the next day. I was nervous and felt dirty on the drive but he told me to put my hands in his pants and I instantly forgot the why and was only focused on but I wanted to do with his cock. Ultimately he was very gentle starting out and it felt like a casual hookup but yeah, in the end he fucked the absolute shit out of me. Ended up going to his place every three or four weeks, eventually forgot about the nature of the terms and was just hooking up with him