At age 17, I lost my (gay/anal) virginity to a guy via casual encounters. He gave me directions to his hotel near the airport with details all the way down to which set of stairs to walk up. The level of detail creeped me out, so I chose my own route through the hotel. Knocked on his door & he let me in. Wanted to know why I didn't go the way he described. It was an odd start to the evening. He had thrown a towel over the desk lamp which provided some soft mood lighting. He was was older than me, buff, and looked Mediterranean. Looked just like his pictures, actually. He went in immediately for a kiss, but I pulled away. Just sex, I told him. We both undressed. He had a huge cock that I just wanted to play around with, bury my face in, and generally enjoy. He pretty much just wanted to stick it in my butt and I obliged. He positioned me like he wanted and tried sticking it in. Virgin ass can be awfully hard to penetrate and this guy wasn't being patient at all. He asked if this was my first time. "No. Of course not!" I told him. But I'm sure he could tell otherwise. He managed to get inside me and started thrusting mercilessly. I accidentally kicked a lamp off the bedside table with my involuntary flailing - had never had such an awesome sexual encounter. He came, but I didn't. He politely blew me to completion. I cleaned up, dressed, and was ready to leave. I commented on his folded scrubs sitting in his suitcase. Asked if he's a doctor or a nurse. Instead of being honest, he conflated his job into being some high-risk nuclear assignment. "So you fix nuclear imaging equipment?" He stuck to his bullshit description instead. Before leaving, he said he'd call me when he comes into town in a month. He never called or emailed.
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