About a month later, he was ready to teach me something new. I give him a great deal of credit when it came to teaching me something new. He never "forced" me. He would make a suggestion, but always followed it giving me a way out by saying, "if you want to." Having enjoyed everything he suggested so far I was always willing to do what he asked. This request was a tough one thoough. He wanted me to get completely naked. By now, through our regular conversations, he knew I was embarrassed by my underdevelopment compared to him. So basically he says, "take off your clothes and lay down on the couch on your stomach, if that's cool with you." I really wasn't thrilled at this request so I asked WHY? He said, " I want to try something, but it's cool if you don't want to." His tone sounded like he was disappointed in me. I felt bad so I reluctantly undressed and laid down on the couch. He said, "I'll stop anytime you say, ok?" I said, "ok." He then leaned over the couch placing one leg against the back of the couch and placed his other foot near the edge of the couch closest to my hip. I could feel him lowering himself towards me and just then I felt his hard warm cock laying in the crack of my ass. This caused me to clinch my ass cheeks together tightly. He sat back on my calves some and said, "just relax, I won't hurt you." I trusted him completely and did my best to relax my ass cheeks. He put his hands on my ass cheeks and spread them openly slightly. What he did next was the first time he did something to me that I received pleasure from. He slid his cock right up and down my ass crack rubbing his cock back and forth against my asshole. I was scared as fuck, but found the sensation of his cock rubbing against my asshole so sensual. It was so pleasing I found myself pushing my ass back against him. It had to be quite noticeable because he said, "you like how my dick feels against your ass don't you?" I admitted I did and he snapped back a reply saying, "I knew you would." We did this many times over the next few weeks, but he never once tried to penetrate me. He was completely satisfied with rubbing his cock against my asshole until he was ready for me to flip over so he could fuck my mouth. This was right about the time he began to reveal his aggressive dominate side more along with his dirty talking.