In previous communications, I've been telling you about my affair with Kathleen, and about how masturbation (in front of her, by her, etc.) was such a big part. For a long time I had a desire to 'get caught' jerking off. I fantasized about a woman, who I didn't know, catching me pleasuring myself. I worried, however, about my family, friends or business associates finding out. So, if I was really going to do it, I determined it had to be when I was out of town on business. I also was not going to place myself in jeopardy of getting arrested by doing it in public. My plan was to get caught by a hotel maid.
I planned to do it on many trips, but never got up the courage. Finally on a trip to St. Louis, I did it. One morning, I stayed in bed until 9 or 9:30 am listening as the housekeeping staff worked their way down the hall. I was on the bed, naked, lightly stroking myself to stay hard and be ready when needed. After a bit, the knock on my door came. 'Housekeeping!' the voice called out while knocking. I remained silent. The door opened and I held my breath as the woman came around the corner of the small entryway into the part of the room where the bed was located. Suddenly, she saw me. 'Oh!' she exclaimed and quickly turned to leave. 'Wait!' I called out, 'don't leave.' The woman turned her head toward me. 'Just stay and watch me,' I said, 'I won't touch you, I just want you to watch me.' The woman said nothing for a few seconds. 'I have to close the door,' she finally said. I hadn't realized that when she entered, she had propped the door open. She walked to the door. I heard her close it, then turn the dead bolt. When she did that I realized she was going to stay. My heart was in my throat!
The woman was about forty-five or fifty and overweight. She had large tits that hung low on her chest. Porn magazines would refer to them as 'floppers.' At one time, fifteen or twenty years age, she was probably attractive. But, now she was simply a woman, a stranger to me, who I was going to masturbate in front of. As I slowly stroked my dick, I asked, 'Do you smoke?' 'Why?' she asked. 'Watching women smoke excites me,' I replied. 'This is a non-smoking room,' she said. 'Please,' I said. The woman pulled a pack of cigarettes from her uniform pocket and lit one. I now began to stroke slightly faster. 'Show me your tits,' I said. 'No!' she said firmly, 'you just finish your business.' 'Please,' I pleaded, 'no one will ever know.' The woman looked over to the window and made sure the shades were completly drawn. Then to my amazement, she unbuttoned her uniform dress, from the waist to the collar and unhooked her bra. When she removed the bra, I was staring at two of the biggest, longest tits I have ever seen. 'Oh, shit!' I called out, 'I'm going to cum!' My dick exploded. I later told Kathleen about jerking off infront of this stranger, but I never revealed that this climax produced more cum than even those that Kathleen had created. When I was finished, I had cum on my face and chest, and my hand was covered. For a few moments I layed on the bed with my eyes closed. When I opened them, the woman had already put her bra back on and buttoned up her dress. She was beginning to walk out, without a word. 'Thank you!' I called out. She stopped and turned her head to me, 'No, baby, thank you.' She left.
I looked for her over the remaining two days I was staying at that hotel, but didn't see her again.
I still think about her.