1. My first time with a man, when I was over 50


    Date: 8/17/2016, Categories: True Story, Anal, Bisexual, First Time, Gay, Author: bennybest, Source: sexstories.com

    My sex with a man – the first time. It had been a long week of sales calls, it was Thursday night and one more day to go before heading home. I had taken a hotel in the middle of the city, most central to my customers, on a quiet side street. For years, when travelling alone, I've had a little private ceremony, celebrating myself. Tonight I needed a pick up before venturing out for dinner. My trusty dildo was in the bag. I rinsed my rear with my water bulb, lubed myself and proceeded to have anal sex, all on my own. This little procedure had, with time, almost become a routine. I was a married man and never sought sex with any other women for my entire married life. But wanking off with a dildo inside me felt good and seemed totally harmless. Eating in the hotel was not on my agenda. Unfortunately, many hotel dining rooms are either outrageously expensive, or serve awfully mediocre food, or sometimes both. “Where is the nearest restaurant?” “One half block down the street.” That sounded convenient and off I went. Sure enough there it was. The menu displayed outside seemed varied and reasonably priced. I stepped in. There was an armed guard standing just inside the door. Oops, this must be a really dangerous area of town. I feel safe to be here, not that I have ever thought about dining under the eyes of a man with a gun before. The place was near full. I was offered to sit with two ladies. “Sure, come sit with us.” We had an amicable discussion about this and that and then ...
    we moved on to relationships. They were good friends, lesbians and lovers. It gradually dawned on me, innocent me, this is a restaurant that caters to the gay community. I have never had much to do with lesbians before so I must admit, I asked a few rather personal questions about sex and relationships in general. The TV was showing the news over the bar. After dinner, I decided to linger at the bar, have a last beer, watch the news and then return to my hotel. There was a young man sitting next to me. We started talking about the news. He told me that he was, 27, an amateur swimmer, and in the bar waiting for his girlfriend to come pick him up after work. She'd call him when she was ready to come. His girlfriend would be late tonight and it was quite clear he would be there for a while. This was an intriguing situation. Perhaps he was gay? I have never really met a gay man in private. Well, since we were in a gay bar, why not ask? I asked him if he'd like to come to my room, I could serve him a rum and Coke. “That's a good idea, drinks are expensive here,” he said. The walk was very short to the front door of the hotel. I felt a little guilty as we rode the elevator, I don't think I had ever had a visitor in my hotel room before. We seated us by the little table and I proceeded to mix our drinks. I stood against the desk with my back towards him. As I turned around, I was stunned. There he was, stark naked with an erect dick pointing straight at me. I caught myself, released ...
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