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Dating Disasters
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Straight Male / 50
Movie And A Facial
Over 10 years ago I was working in a small, remote city in the midwest, on a job which I knew wouldn't last more than a couple of years. So I didn't make a lot of connections there, and spent much of my free time getting books and movies from the public library. The staff there got to know me as a regular and in my second year one of the women handed me my videos adding that she loved to watch and talk about movies and would like to hear my thoughts on what I watched sometime. I didn't think I was going to stay much longer, but I figured a date wouldn't hurt so I gave her my number. She was at least five years my senior, white, with dark curly black hair, and I honestly didn't find her very attractive, but I appreciated her forwardness.
She called me within a day and I invited her over to my place, where I talked about my movie interests (drama, history, comedy) and shared some insights on a few films. We also talked about our broader lives; mine was very academic, hers had been more limited, with a bad marriage she escaped and a string of retail jobs after high school.
One of the things I talked about was how movies can present big concepts and serve as reference points to explain complex issues, or break the ice on some that are otherwise hard to broach. For instance, I praised The Whole Wide World for its portrayal of how Robert Howard was caught up in his "rough" view of fantasy behavior, including sex, which he both wanted to somehow make real in his actual life but also was certain no one else (least of all Renee Zellweger's character) could accept if he implemented it in reality, when all the while she was making it pretty clear that she might really be open to that after all and he should give it a try. That led to a discussion of secret sexual fantasies that we all kept inside ourselves and both wanted to act on and were afraid of what others would think. She said she really didn't have any, but knew men (and other women) sometimes did. I was a bit shy or coy at first and said she probably wasn't ready to hear mine, but she said something reassuring and said it would be safe with her, the worst she could say was no. I told her I loved blowjobs and facials, the visual sight of my cock in a mouth or my cum on a woman's face. She said that didn't seem that unusual though she said she almost never got a facial, at least not intentionally. She asked me more about that and I explained that it was always part of my fantasy life, and as much of my real sex life as it could be, and that I once even gave a woman a facial without any other sex. She said this was interesting and that she had sometimes watched men masturbate but never on her face.
It was late so she soon went home but we made plans to watch some movies at her place on Saturday. We had some dinner and talked about the week, then went to the living room floor as she had no couch, just a bunch of floor pillows. I sat up against the wall while she lay on the floor with her head propped up. We watched some English drama whose name I forget, but things got interesting as I rubbed her shoulder, head, and then face. She held my hand as I touched her, which felt very erotic. I put my hand on her cheek and she leaned into it. Well I got pretty hard and so soon unzipped my pants to release my cock and started stroking it, Fortunately the movie was almost over so I just held it there until the credits started to roll and then started jacking in earnest. I was hoping for a blowjob of course but she didn't make any move to do that so I just started rubbing my cock lightly against her face. She said nothing but let me keep doing it for a long time. Finally I repositioned myself more to the side of her head so I could aim my cum at her face better, and also could just barely touch her lips on certain strokes. She mostly sat still, but gave me just one or two slight glances as if just to "check in" though without any clear expression on her face. Finally I felt the rush of imminent flow and gasped as my cum began to spurt onto her face, with 3 strong squirts followed by a few weaker pulses and drips. Several big globs covered her left cheek and a corner of her lips, with a bit on her nose and a dab on her forehead as well. She was mostly staring into space quite still, and then looked at me and asked me how it felt. I told her it was wonderful and thanked her for letting me do that, then asked how she felt. "Doesn't do much for me" she said, "but I'm glad you enjoyed yourself." We didn't talk much more, but I kept looking at her face and enjoying the sight of my cum all over her. She finally asked "is there anything else you want to do," and I asked her to sit up so I could stand over her and rub my face with her cock, catching the dripping cum and spreading it around. I rubbed it across her lips a few times, and this made me harder again so I held it there for a bit. She then sucked me a little bit for a few minutes, though she confessed she didn't think she was very good at blowjobs. And she wasn't, but getting sucked by a woman whose face you just came on is a treat no matter how it's done, so I thanked her and then helped her clean up. We talked for another half hour, not about sex at all, and then I left. I thought that might be our last date, but we got together two more times before I had to break it to her that I was leaving the city. She wished me well and said she hoped I found more opportunities to spread my wild roughness around.
She called me within a day and I invited her over to my place, where I talked about my movie interests (drama, history, comedy) and shared some insights on a few films. We also talked about our broader lives; mine was very academic, hers had been more limited, with a bad marriage she escaped and a string of retail jobs after high school.
One of the things I talked about was how movies can present big concepts and serve as reference points to explain complex issues, or break the ice on some that are otherwise hard to broach. For instance, I praised The Whole Wide World for its portrayal of how Robert Howard was caught up in his "rough" view of fantasy behavior, including sex, which he both wanted to somehow make real in his actual life but also was certain no one else (least of all Renee Zellweger's character) could accept if he implemented it in reality, when all the while she was making it pretty clear that she might really be open to that after all and he should give it a try. That led to a discussion of secret sexual fantasies that we all kept inside ourselves and both wanted to act on and were afraid of what others would think. She said she really didn't have any, but knew men (and other women) sometimes did. I was a bit shy or coy at first and said she probably wasn't ready to hear mine, but she said something reassuring and said it would be safe with her, the worst she could say was no. I told her I loved blowjobs and facials, the visual sight of my cock in a mouth or my cum on a woman's face. She said that didn't seem that unusual though she said she almost never got a facial, at least not intentionally. She asked me more about that and I explained that it was always part of my fantasy life, and as much of my real sex life as it could be, and that I once even gave a woman a facial without any other sex. She said this was interesting and that she had sometimes watched men masturbate but never on her face.
It was late so she soon went home but we made plans to watch some movies at her place on Saturday. We had some dinner and talked about the week, then went to the living room floor as she had no couch, just a bunch of floor pillows. I sat up against the wall while she lay on the floor with her head propped up. We watched some English drama whose name I forget, but things got interesting as I rubbed her shoulder, head, and then face. She held my hand as I touched her, which felt very erotic. I put my hand on her cheek and she leaned into it. Well I got pretty hard and so soon unzipped my pants to release my cock and started stroking it, Fortunately the movie was almost over so I just held it there until the credits started to roll and then started jacking in earnest. I was hoping for a blowjob of course but she didn't make any move to do that so I just started rubbing my cock lightly against her face. She said nothing but let me keep doing it for a long time. Finally I repositioned myself more to the side of her head so I could aim my cum at her face better, and also could just barely touch her lips on certain strokes. She mostly sat still, but gave me just one or two slight glances as if just to "check in" though without any clear expression on her face. Finally I felt the rush of imminent flow and gasped as my cum began to spurt onto her face, with 3 strong squirts followed by a few weaker pulses and drips. Several big globs covered her left cheek and a corner of her lips, with a bit on her nose and a dab on her forehead as well. She was mostly staring into space quite still, and then looked at me and asked me how it felt. I told her it was wonderful and thanked her for letting me do that, then asked how she felt. "Doesn't do much for me" she said, "but I'm glad you enjoyed yourself." We didn't talk much more, but I kept looking at her face and enjoying the sight of my cum all over her. She finally asked "is there anything else you want to do," and I asked her to sit up so I could stand over her and rub my face with her cock, catching the dripping cum and spreading it around. I rubbed it across her lips a few times, and this made me harder again so I held it there for a bit. She then sucked me a little bit for a few minutes, though she confessed she didn't think she was very good at blowjobs. And she wasn't, but getting sucked by a woman whose face you just came on is a treat no matter how it's done, so I thanked her and then helped her clean up. We talked for another half hour, not about sex at all, and then I left. I thought that might be our last date, but we got together two more times before I had to break it to her that I was leaving the city. She wished me well and said she hoped I found more opportunities to spread my wild roughness around.
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