Emily and Steve Part 9

"Hey, I want you to fuck me," I said.

"Do you have a car?" he asked, looking around.

"Not tonight. Just take me over in the bushes there, tear my pants down and rape my ass. I want you to punish me. Make me hurt," I said.

The guy looked at me funnily, but then said he'd do it for one hundred. I pulled out five twenty dollars bills and gave it to him as I started to wander over to the bushes.

Before the tranny had even followed me into the bushes, I had my pants around my ankles, and was bent over against a tree. I spread my ass cheeks and ordered him to fuck me hard and fast.

The tranny stood behind me and hiked up his skirt. I could hear him playing with himself as he took a condom out of its packet. Once he was hard enough and had the condom on, he entered my ass.

He was big, much bigger than Emily had been, and not at all gentle. He pushed in me, and I shuddered with pain. That was fine though, for it was pain I wanted to feel. The tranny started pushing into me hard and fast. I started to relax, and the pain started to turn to just discomfort, and then surprisingly to pleasure. I opened up, and soon shivers of pleasure were pulsing from my ass. It was causing my cock to stand up at attention. I soon found myself reaching down and jacking myself off as the tranny continued to pound away at my tight asshole.

"Do you like that?" he asked me.

"Yes," I whimpered. I did. I suddenly felt an intense desire to have more of this. I wanted more cocks in my ass. I had never felt that way before. The feeling welled up in me, and I found myself spurting my load against the tree and the tranny pounded hard and fast. Once I was done, the tranny took off the condom, tucked away his cock, pulled down his dress and walked away.

I was left in the bushes, my pants around my ankles, feeling both strangely satisfied but at the same time empty.

* * *

On Monday evening, I thought it would be best to clear the air between Emily and I. My plan was to lay everything out on the table and see how we can make it work. I went to the gym first to work off any nervous energy and anger, and so when I arrived home, Emily was already sitting on the couch. I walked over and sat down.