Frustrated
I agreed in doing it, as long he made me a blowjob and let me cum on his mouth. This guy never have done nothing like this and he was uncertain about the blowjob, but 100% in getting my cock deep in the ass.
After some more messages, he finally decided in blowing me but I wouldn't cum on his mouth.
We met after two days on a cheap hotel room and he was really nervous about it.
I assured him that I wouldn't push my cock down the throat and cum inside.
He seated on the couch with the eyes closed and waiting to feel my cock in his lips. I started by using my big mushroom head as a lipstick and told him to start to kiss it and slowly start sucking it like a ice cream and let it go inside until he couldn't more. He clearly had no experience and asked me to basically do everything. I could feel my cock head beating in the back of his head but just ask him to suck my mushroom until I cum right on his face. Something that he wasn't expecting but didn't seem to care.
After washing the face he took a good look at my cock and started having doubts that he could handle everything deep inside the ass.
I grabbed my lube bottle and put that big ass in position to be penetrated. That butthole was indeed super tight and I knew that this is going to take time to get the hole relaxed and with enough lube to make sure my big mushroom head would go inside automatically. I explained that he needed to relax and let my fingers start to open the door. The moment he felt his hole getting stretched by my cock going inside he started panican and wanted to stop. I told him to hold on my cock inside him. I tried going full on, but he couldn't stand the pain. He rapidly got dressed and until run out the door. It was a frustrating moment... I barely got 10 cm inside and the blue pill was kicking in.
He never replied to my messages since then.


