I gently squeezed and massaged his cheeks around the head of the dildo and slowly began pushing it into him. He was loosened enough from the previous ...dildo so that his ass accepted the new one, but I could see how much more it had to stretch and I could feel his apprehension under me. I went very slowly and it actually took several minutes for the head to pass his sphincter. He moaned loudly as it slowly began to enter him. I could tell he wasn't relaxing like he normally does but boy was this. I happened to see more than one guy follow me with his eyes as I walked towards a table where I saw a couple gathering their things getting ready to leave. I think I liked the looks I got as it made me sway my hips a bit more than usual.A shorter, stocky drag queen approached me for a cover and told me the proceeds went to a worthy cause.Pam the philanthropist! I smiled inwardly. She gave me a ticket stub and told me to have a wonderful time as everyone here was super friendly and the bar staff. The day before I was going to come home she called in the middle of the day to say and hi and see how that day was going. She started asking a series of strange questions. Things like “When are you going to be back out there?” and “Do you always stay at the same hotel?” I told her that I was going to be out about two months down the road and no... I would be in another hotel next time. “Why do you ask?”“I was thinking about that maintenance guy that you gave my panties and picture to” she. We took the long drive to the drive in with few cold beers and a couple of joints. By the time we got there all of us were feeling pretty loose and ready for the movies to begin. Of course it wasnt too far into the movie that both couples were getting intimate. I watched as Sandys head disappeared in to Dons lap. That was enough set the tone of the rest of the night. When Sandy sat back up licking her lips she looked back at us and winked. Then she reached down and puller her top up and over.