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Dating Disasters
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Straight Male / 50
Why I Left Behind The Best Blowjobs In The World, Part 1
So this is about a date which went very right in many ways, and wrong in some others. It’s an experience I will always be glad I had, and always feel ambivalent about.
A few years ago I was in graduate school, and feeling a bit isolated in a new city as I didn’t quite connect closely with any of my fellow students, nor easily with anyone outside it. I joined a local social group to meet people, and eventually a woman there showed some interest in my studies, several times asking me to summarize some of my work. After a few weeks she asked if I’d be interested in going “around the town” with her and her female roommate one Saturday night. It wasn’t my usual thing, but I had little better to do so I agreed. I soon learned that this basically meant I was their designated driver while they went barhopping and trying to pick up guys more to their style than I was, and over the course of the night concluded that the woman really had no interest in me or my studies as such, but had identified me as someone they could string along for this service.
We ended up at a nightclub in a large mall, where everyone was drinking beer and enjoying silly music, and seeing that the two ladies would be occupied there a while, I drifted into the hall and an adjoining, quieter venue. Here my story really begins, for a slightly older black woman, Callie, soon struck up a conversation with me. We were both alone, but her interest in me seemed more genuine, and I felt she wanted to actually talk to me as such, not just because I was conveniently alone like her. She said she occasionally went there on weekend evenings, perhaps to meet someone, perhaps just to have some time away from raising her two children (then in their early teens, just old enough to be left alone for a few hours). She did night-shift custodial work at a health center, which explained why she was up so late on her weekend. In many ways her background was very different from mine, yet she was highly intelligent, and I suspect probably could have gone farther in life but for some difficult circumstances which I only gradually learned more about, and which I was privileged enough to avoid through no merit of my own. In short, she had suffered abuse and economic hardship, but had a persevering spirit which kept her going, and brought her to introducing herself to yet another stranger that night. I can’t say she was stunningly beautiful, yet she had a disarming charm about her, a light that shone through her eyes and her speech which moved me. Certainly I’m no George Clooney myself, and my own introverted interests turn many people off, but Callie seemed to really care about me despite our different backgrounds and lives.
We talked for at least two hours, there and out in the quieter hall, until I finally confirmed that my rides were ready to go home soon. We wanted to talk more, but Callie had nothing to write on, and I didn’t have a cell phone back then. She had a checkbook though, and tore off the corner of one check with her name and address, saying that she feared I would lose it or just decide not to call, but I assured her I would. I took my ladies back to my place, and when they sobered up enough to drive home they did. I’ll admit, I had some dim hopes earlier of a threesome with them, but clearly that was nowhere in the offing; what I got in the end was in many ways better though, despite a few issues which arose later.
I called Callie the next day, which delighted her, and after talking some more she invited me to pick her up outside her apartment and take her back to my place. Here we share more of our histories; her recent move from another state, her past relationships almost exclusively with white men, her determination to keep looking for something better for herself while taking care of her children; while I shared my long search for a partner while rejecting anyone whose values or lifestyles weren’t sufficiently compatible with my rather focused ones.
It was a warm summer day, so we ended up lounging on my king-sized bed under a ceiling fan. There was definitely a physical attraction, and I wanted to touch her, so I offered a massage, which she gratefully accepted. Rubbing her back and hips through her clothing was fun for both of us, and something she definitely needed after the labor of her weekday job.
After massaging her a while, I had an uncomfortable tenting in my underwear, so I finally reached down to loosen my penis. I felt comfortable telling her directly that I had gotten excited from touching her and had done this to relieve the pressure, but that “I’m not expecting you to do anything about it” and continued rubbing her. She expressed gratitude for my directness about this, but after a minute did roll back in my direction to face me, or rather my body, since I had been rubbing her left hip from behind and her face was closer to my feet. She saw my erect penis and said something admiring about it, appreciating that I wasn’t aggressive but mater-of-fact about my being turned on by touching her body. After a couple minutes she asked “can I touch it?” I said she could, and enjoyed feeling her hand on my hardness. She compared it favorably in length to others she had seen, and kept touching it as if she was exploring and trying to understand it, rather than trying to excite it further—which actually was exactly the kind of treatment I found extremely exciting. She also began talking about how she enjoyed penises, and very often gave her partners oral sex. She asked me if I enjoyed receiving oral sex, and I said I did, that indeed it was my favorite sex act.
I was not surprised, then, when she asked “can I put it in my mouth?” I let her do this, and watched studiously as she began slowing tasting me, gingerly feeling out my rigid organ with her soft lips. After a couple minutes she stopped and asked how it felt. I assured her it felt good, and that I would enjoy more of that. Thence began at least an hour of an on and off cock sucking session in various positions; on our sides as we began, 69 with me on top, standing with her sitting in front of me, or me sitting on her face, and countless other variations. She kept her clothes on the entire time, while I gradually stripped for greater comfort and access. I even asked if she wanted to strip or for me to pleasure her, but she said she’d rather just do this, which made her feel peaceful and happy. I wasn’t about to object. Eventually I wanted to cum, so I asked if she was comfortable with semen in her mouth; she was, so I sat over her on the bad and after some more ball and cock sucking, I jerked off onto her tongue, letting her again envelop my penis to clean it off.
She stayed for at least another hour as we caressed, cuddled, and talked about life, but eventually I had to take her back home so she could prepare for working her night shift. I thought about her a bit during the week before our next date at her apartment, where we watched a movie on her small TV set after her kids had gone to bed. I actually had to watch this same movie again a few years later, absorbing almost none of it that night, because we quickly got distracted. I sat on a chair, Callie on the floor in front of me; I was soon massaging her shoulders, which soon led to the same excitement as our first date. She picked up quickly when I exposed my hard penis, and turned around to start sucking me. Here I learned something I somehow didn’t observe on our first date: that she could deep-throat me with absolutely no difficulty, pressing and holding her lips all the way onto my pelvis. I also started guiding her head and soon found her encouraging me, so I began pumping her mouth up and down my shaft without reserve. The movie played on as I enjoyed the rhythmic sensations, finally pulling her hard into my belly as I ejaculated strongly down her throat. We tried to watch the movie a little longer, but soon I was excited again by the thought of her powers, and I fucked her mouth for at least another half-hour before cumming once more into her hot throat.
This was amazing; I had never been deep-throated before, and almost never found a woman who let me pump her head up and down my cock; Callie could do both easily. We had several more dates where I was able to enjoy her oral skills, but sadly they also revealed the limitations of our relationship. Her kids were often around when I came by on later visits, but the main problem was her schedule; we could only meet in the evenings, when I soon ran out of energy and she was just getting started. Hence, we could never sleep together, and after ejaculating, I often had to go home, precisely when she was hoping to see more of me. We also started running out of things to talk about. On one of my last visits, she said she didn’t think I was able to cum, but I wanted to keep fucking her mouth anyway and felt I would cum eventually; realizing that I resented her for not trying harder made me realize that I was using her sexually. We also fucked that time, though without either cumming, and my constant desire for more one-sided pleasure also made me feel guilty. I vacillated about this several times, twice essentially telling her we couldn’t go on, only for her to invite me to enjoy time with her again, but finally I simply ghosted her and we drifted away.
See part 2 for follow-up.
A few years ago I was in graduate school, and feeling a bit isolated in a new city as I didn’t quite connect closely with any of my fellow students, nor easily with anyone outside it. I joined a local social group to meet people, and eventually a woman there showed some interest in my studies, several times asking me to summarize some of my work. After a few weeks she asked if I’d be interested in going “around the town” with her and her female roommate one Saturday night. It wasn’t my usual thing, but I had little better to do so I agreed. I soon learned that this basically meant I was their designated driver while they went barhopping and trying to pick up guys more to their style than I was, and over the course of the night concluded that the woman really had no interest in me or my studies as such, but had identified me as someone they could string along for this service.
We ended up at a nightclub in a large mall, where everyone was drinking beer and enjoying silly music, and seeing that the two ladies would be occupied there a while, I drifted into the hall and an adjoining, quieter venue. Here my story really begins, for a slightly older black woman, Callie, soon struck up a conversation with me. We were both alone, but her interest in me seemed more genuine, and I felt she wanted to actually talk to me as such, not just because I was conveniently alone like her. She said she occasionally went there on weekend evenings, perhaps to meet someone, perhaps just to have some time away from raising her two children (then in their early teens, just old enough to be left alone for a few hours). She did night-shift custodial work at a health center, which explained why she was up so late on her weekend. In many ways her background was very different from mine, yet she was highly intelligent, and I suspect probably could have gone farther in life but for some difficult circumstances which I only gradually learned more about, and which I was privileged enough to avoid through no merit of my own. In short, she had suffered abuse and economic hardship, but had a persevering spirit which kept her going, and brought her to introducing herself to yet another stranger that night. I can’t say she was stunningly beautiful, yet she had a disarming charm about her, a light that shone through her eyes and her speech which moved me. Certainly I’m no George Clooney myself, and my own introverted interests turn many people off, but Callie seemed to really care about me despite our different backgrounds and lives.
We talked for at least two hours, there and out in the quieter hall, until I finally confirmed that my rides were ready to go home soon. We wanted to talk more, but Callie had nothing to write on, and I didn’t have a cell phone back then. She had a checkbook though, and tore off the corner of one check with her name and address, saying that she feared I would lose it or just decide not to call, but I assured her I would. I took my ladies back to my place, and when they sobered up enough to drive home they did. I’ll admit, I had some dim hopes earlier of a threesome with them, but clearly that was nowhere in the offing; what I got in the end was in many ways better though, despite a few issues which arose later.
I called Callie the next day, which delighted her, and after talking some more she invited me to pick her up outside her apartment and take her back to my place. Here we share more of our histories; her recent move from another state, her past relationships almost exclusively with white men, her determination to keep looking for something better for herself while taking care of her children; while I shared my long search for a partner while rejecting anyone whose values or lifestyles weren’t sufficiently compatible with my rather focused ones.
It was a warm summer day, so we ended up lounging on my king-sized bed under a ceiling fan. There was definitely a physical attraction, and I wanted to touch her, so I offered a massage, which she gratefully accepted. Rubbing her back and hips through her clothing was fun for both of us, and something she definitely needed after the labor of her weekday job.
After massaging her a while, I had an uncomfortable tenting in my underwear, so I finally reached down to loosen my penis. I felt comfortable telling her directly that I had gotten excited from touching her and had done this to relieve the pressure, but that “I’m not expecting you to do anything about it” and continued rubbing her. She expressed gratitude for my directness about this, but after a minute did roll back in my direction to face me, or rather my body, since I had been rubbing her left hip from behind and her face was closer to my feet. She saw my erect penis and said something admiring about it, appreciating that I wasn’t aggressive but mater-of-fact about my being turned on by touching her body. After a couple minutes she asked “can I touch it?” I said she could, and enjoyed feeling her hand on my hardness. She compared it favorably in length to others she had seen, and kept touching it as if she was exploring and trying to understand it, rather than trying to excite it further—which actually was exactly the kind of treatment I found extremely exciting. She also began talking about how she enjoyed penises, and very often gave her partners oral sex. She asked me if I enjoyed receiving oral sex, and I said I did, that indeed it was my favorite sex act.
I was not surprised, then, when she asked “can I put it in my mouth?” I let her do this, and watched studiously as she began slowing tasting me, gingerly feeling out my rigid organ with her soft lips. After a couple minutes she stopped and asked how it felt. I assured her it felt good, and that I would enjoy more of that. Thence began at least an hour of an on and off cock sucking session in various positions; on our sides as we began, 69 with me on top, standing with her sitting in front of me, or me sitting on her face, and countless other variations. She kept her clothes on the entire time, while I gradually stripped for greater comfort and access. I even asked if she wanted to strip or for me to pleasure her, but she said she’d rather just do this, which made her feel peaceful and happy. I wasn’t about to object. Eventually I wanted to cum, so I asked if she was comfortable with semen in her mouth; she was, so I sat over her on the bad and after some more ball and cock sucking, I jerked off onto her tongue, letting her again envelop my penis to clean it off.
She stayed for at least another hour as we caressed, cuddled, and talked about life, but eventually I had to take her back home so she could prepare for working her night shift. I thought about her a bit during the week before our next date at her apartment, where we watched a movie on her small TV set after her kids had gone to bed. I actually had to watch this same movie again a few years later, absorbing almost none of it that night, because we quickly got distracted. I sat on a chair, Callie on the floor in front of me; I was soon massaging her shoulders, which soon led to the same excitement as our first date. She picked up quickly when I exposed my hard penis, and turned around to start sucking me. Here I learned something I somehow didn’t observe on our first date: that she could deep-throat me with absolutely no difficulty, pressing and holding her lips all the way onto my pelvis. I also started guiding her head and soon found her encouraging me, so I began pumping her mouth up and down my shaft without reserve. The movie played on as I enjoyed the rhythmic sensations, finally pulling her hard into my belly as I ejaculated strongly down her throat. We tried to watch the movie a little longer, but soon I was excited again by the thought of her powers, and I fucked her mouth for at least another half-hour before cumming once more into her hot throat.
This was amazing; I had never been deep-throated before, and almost never found a woman who let me pump her head up and down my cock; Callie could do both easily. We had several more dates where I was able to enjoy her oral skills, but sadly they also revealed the limitations of our relationship. Her kids were often around when I came by on later visits, but the main problem was her schedule; we could only meet in the evenings, when I soon ran out of energy and she was just getting started. Hence, we could never sleep together, and after ejaculating, I often had to go home, precisely when she was hoping to see more of me. We also started running out of things to talk about. On one of my last visits, she said she didn’t think I was able to cum, but I wanted to keep fucking her mouth anyway and felt I would cum eventually; realizing that I resented her for not trying harder made me realize that I was using her sexually. We also fucked that time, though without either cumming, and my constant desire for more one-sided pleasure also made me feel guilty. I vacillated about this several times, twice essentially telling her we couldn’t go on, only for her to invite me to enjoy time with her again, but finally I simply ghosted her and we drifted away.
See part 2 for follow-up.
