It was 2 a.m. Linda was not a fanatical clean-freak, or a wanna-wash-washer woman, nor was she fond of doing chores in the middle of the night. What L...nda was, however, was a devoted dare-devil, a desperate taker and giver of dares.The 19 year old medical secretary had been taking and giving dares in person and on-line for years, ever since she was a high school freshman. In those early days they were sort of childish stunts reflective of the social milieu of classroom and extracurricular. The head of his cock felt huge as it pressed against my virgin hole. Try as I did I could not relax at first but when I finally did the head of his cock popped into my ass and I understood what he meant about the pain. I wanted him to stop so bad but I had not been fair to him, I had no reason to expect he would take it easy on me…fair is fair. I also understood the pleasure he was feeling and how hard it is to control yourself when you first break into that dark pit. I grunted as he pushed. Tom felt awkward with his jeans and plaid shirt with the sleeves rolled up. It was all he had, but it was clean and Ellen never said anything. Ellen’s family didn’t have much, but Tom’s family was poor and that bothered him. There was very little money and what money Tom had, he worked hard for. It had taken him months to make enough to purchase the red Ford Pickup that had seen better days. Ellen ran down the steps of the porch and jumped inside the truck on the passenger side. She leaned over. I stroked my dick and contemplated what I was about to do. I realized I better get it over quick or I would chicken out.I got on my knees behind Derek and walked into position. I wanted to ask him if he had had anything in there before, but knowing Amanda she'd probably strapped on a dildo and fucked him with it.I put one hand on his hip and the other on my dick and pushed it at his anus. When my dick head was against it I put my hand on his other hip and pushed gently.I was afraid to push too.