Loosening him up before shoving a dick inside was what you were supposed to do for a partner. Marco was not a barbarian. That was good to hear. "I fingered him for a bit while jerking him off. Tassos was panting and moaning finally. I was doing it for 8 minutes at least. First, I used 2 fingers. Then I moved up to 3. After he came, I gave him a minute to relax. He told me to put it in." he recounted. It sounded like things had been a success. I gestured for him to keep going. "What happened next?" I asked him. He was totally red in the face now. "I was right there! But by the time I got out my briefs, I was totally soft. Nothing worked!" Marco whined. I could only shrug my shoulders. "Drinking can cause that effect in some men. I would try to do it sober next time you meet up. Tassos got off this time, so I doubt that he'll complain." I said. It was his first time at the end of the day. Some guys fuck it up. Marco would live and learn from the experience. "What if the same thing happens again!?" he asked. "If it happens again, completely sober, you just aren't attracted to him bottoming, Marco."
Discussing it during the dinner did seem to stick in his mind. Marco was a very willful and determined person. It did not surprise me that he would take the initiative here at all. It did surprise he that he did not try to brute force the way he wanted. He probably had to switch gears when Tassos was not getting hard enough to penetrate. This was something that Marco wanted. He looked at me. "Do you really think I should go for it again!?" he asked. "If you tried really hard and it still didn't work, maybe you might need to come to a decision. Still, I know that you really like him. You can give it one more try." I replied. At the end of the day, I wanted what was best for Marco. If it was not meant to be, it was fine. They would have come to the decision after discovering they were not right for each other. Nothing could be done at that point. There were always more fish in the sea. People spawned in when they were needed. I had no doubts Marco would be alright. He had looks, money, influence and the most hot tempered personality of his siblings. He'd make his own way through this if needed.
Now that we had our chat, it was time to get back. People would certainly be wondering where we were. Marco still had to dry his tears. Once he was ready, I escorted a composed mob doctor back to where everyone was. His brothers were concerned about his well being. Dante took a back seat to Rocco and Carlo. The 3 of them had lived together their whole lives. Dante had only recently started getting to know his older brothers. That was totally on me. I did not want to hurt Daphne. Having her son hanging around the illegitimate children of my mistresses was not something that she would be comfortable with. Even now, she did want to know anything about it. They all were allowed to meet up and socialize. They worked together now. Daphne had to be aware of this, but there was nothing that she could do. They were now second generation mafiosos. It made them adults in the eyes of the criminal underworld. I would look out for them and they would be massive assets going forward. Believe it or not, I was the patriarch of their new Nesta Family. People looked to me for guidance.
