I remember the first time I saw someone getting fucked in the ass. I stumbled across one of my brother's porn videos one day. My curiosity got the better of me and I decided to look at it. It looked so painful, yet she looked like she was enjoying it. I was shocked, turned on, and embarrased all at the same time. I became hooked, and soon watching his dirty videos became my guilty pleasure, and especially the anal scenes. It got to to the point where I wouldn't even watch straight sex, I just skipped right to the anal. As I watched the scenes, I would finger my ass, too afraid that I might actually enjoy myself. After all, I was only sixteen. As I got older, I worked my way up to putting my finger in my ass, and then dildos of varying sizes. Still, I was afraid to let anyone pop my anal cherry, although I liked to fantasize about it with strangers online. Then I met a man online. His name was Thomas. He was a police officer, and he was much older than me(I'm nineteen). We met in a chat room. Soon we were having our own private conversation. First we talked small talk, like, "What do you do for a living? How old are you? Where do you live? How tall are you? How much do you weigh? What ethnicity are you?" But I was feeling bold, and so I asked him bluntly, "So, have you ever fucked a girl in the ass?"
"All the time", he replied.
"Tell me about it", I begged.
"Why? Do you want to be fucked in the ass?"
I had to pause for a moment. In the course of conversation it was discovered that we live only hours away from each other. I knew what this was leading to. If I told him yes, he would want to arrange a meeting. Was I really ready for that?
"Yes, I do. I'd really like that. I've been curious for a while--"
"Maybe we should meet. Why don't you take the train to my house?"
I agreed. He gave me his address and phone number and it was agreed that I would come to his house the very next Saturday. I couldn't believe what I was getting into. Still, I was excited and chose to wear a skirt with no panties. The whole train ride I was terribly nervous and as I arrived at his apartment, my nerves were jumping. I rang his doorbell. He answered right away. I took a quick appraisal of his looks. I had seen his picture, and he was even more handsome than what I had thought. He was 5'11", had dark brown hair and eyes. He was very muscular, on account of his work. He towered over my tiny 4'11", 105 lb frame.
"Hi." My voice squeaked. He didn't say anything in reply, he just caressed my face softly, then placed his hand firmly on the back of my neck. He pushed me toward him roughly and kissed me deeply. He was a little rough with me, but I liked it. He shut the door behind me.