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Anything Goes
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Straight Male / 49
My Young Pets
A couple decades ago I had been living in one city for several years but moving out of it in about six months to attend graduate school. I was dating a woman in town who I good sex with--she gave great blowjobs, enjoyed anal, came powerfully when I went down on her, and we also enjoyed intercourse after I got a vasectomy. But she was a little flakey with new-age ideas which turned me off a bit because I was a very hard-nosed naturalist, so I occasionally looked to see who else was available.
Online--I think using Matchmaker--I started talking to a 16-year old girl, Dree, about poetry. She actually turned 17 before we met, and was legal age in this state anyway, but this still felt risque as I was almost 30. She talked about being somewhat attracted to women and men both, but didn't have much experience yet. I wanted to meet her badly but she put me off a bit so I'm not sure we would have met except for a coincidence. I am obsessed with blowjobs, mostly getting them of course, but often wondered what it would be like to give one (I had done this a couple times, but didn't fully enjoy the whole experience perhaps because of the people involved, and wanted to try it again). So I also answered the ad of a young man, George, whose profile expressed some interest in some books I had read, and told him bluntly about my interests. I didn't expect to hear back from him at all, but then Dree wrote me a couple days later and asked about this, as it turned out that she and George were friends and were sharing data about their dating explorations. I said this was a good sign that we should all meet, and suggested a venue a few blocks from my house. It turned out to be closed at the time I suggested, so after we met out front I biked back home as they drove there, and we hung out in my living room.
Both Dree and George were a bit overweight, but young and jovial. They shared that they had few friends their age, partly because of their sexuality--George being gay, and Dree being uncertain about her orientation--and partly because they each recently switched to the same school from elsewhere, and perhaps also just being a little different personality-wise from others, and not fully accepted by their parents, though they each lived at home. I assured them that they could consider my house a safe space, if they felt comfortable with me. We then talked a bit more about sex, and I was again blunt about my interests, also mentioning that if I were to have oral sex with a man I'd feel more comfortable with a woman present, to make the experience feel less completely homosexual, if that makes sense, and more of just a side exploration. Dree said that sounded cool, and George was up for it, so soon I kneeled in front of him to take his dick out of his pants. It was small and soft, but I slowly sucked it up to about 4" long as Dree watched. I asked her to watch as closely as possible, and to talk to me about what she was seeing, dirty if possible. She smiled and laughed, enjoying her role, and asked me if I liked being a cock sucker, and having a man's dick in my mouth, and so forth. I told her she could touch me and she started talking about how sexy my strong bicyclist's legs looked, touching both them and my face a little bit, never touching George's dick (they were not attracted to each other and had no sexual interest in each other at any point), but feeling my muscles move as I sucked him off. I loved this and really got into this amazing satisfaction of a long-held fantasy. It didn't take long for George to grunt a little and start ejaculating into my mouth, which I found a little weird, but for Dree's sake I tried to make it look as pleasant as possible, and swallowed as much of his cum as I could.
After I cleaned up a bit we talked about the experience and I thanked George for his willingness. He then asked if i wanted one, and I decided I'd try it; again, I had accepted bj's from men a couple times, but never came in a man's mouth before. I unzipped on the couch and he sat on the floor to suck me while Dree sat next to me and kissed me, letting my fondle and suck her boobs, and so forth. She looked down a couple times but was mostly focused on my face, and I also found it more erotic to look at her than at George, though the feeling of his mouth was very exciting. Finally I looked deeply into Dree's eyes and she looked back with enormous interest as I starting to cum into George's mouth, gripping her tightly and plaintively gasping with joy.
We talked a bit more while I wound down, and Dree watched my dick much more now as it was still semi-hard and hanging out so I could stay comfortable. I thanked them enormously for what they did for me, and they both said they enjoyed it.
They soon had to go, but they came back a couple times again. First I talked about anal play, and how I wanted to be sucked while my asshole was licked. At first Dree was in front and George behind me, as he was more familiar with ass play. This was Dree's first blowjob but she was very good at it. I turned around for a while and had them reverse roles, but then turned again and Dree finished me by taking a huge spurt of cum across her closed lips (she wasn't quite ready for swallowing yet).
Dree then ame by herself once, and gave me a fantastic blowjob on the same couch, this time taking my load into her mouth. Then they both came back and I was feeling even more frisky, so I asked George if he would penetrate me anally--a completely new experience for me--while Dree sucked on me. Again they were up for that, so I got on top of Dree in a 69 position, but with most of her clothes still on, while George sat on his knees behind me and fucked my lubed-up asshole. It was both painful at times and mind-blowing; I both wanted it to stop every second and wanted it to go on forever. I don't ever remember being as hard as I was in Dree's mouth, as if George's hardness was filing up my own cock and doubling its rigidity. It felt both like forever and just a couple minutes before I began squirting into Dree's mouth, and the orgasmic pulsing of my asshole must have also excited George who then started pumping his semen into me.
Even when I was being fucked I felt like I was totally in control, almost using these two kids for my pleasure. I really enjoyed the experience, but confess that I thought of them at times as my high schooler toys, kids I got to play with occasionally to explore my fantasies. It never went further; Dree never took off most of her clothes or let me go down on or fuck her, and I had no interest in penetrating George. A few months later I moved out of town, and only saw Dree once year later, while George (no longer her friend) vanished altogether. Maybe it wouldn't have lasted had I stuck around, but I am glad I got the chance to sow some of my wilder oats around with these willing friends.
Online--I think using Matchmaker--I started talking to a 16-year old girl, Dree, about poetry. She actually turned 17 before we met, and was legal age in this state anyway, but this still felt risque as I was almost 30. She talked about being somewhat attracted to women and men both, but didn't have much experience yet. I wanted to meet her badly but she put me off a bit so I'm not sure we would have met except for a coincidence. I am obsessed with blowjobs, mostly getting them of course, but often wondered what it would be like to give one (I had done this a couple times, but didn't fully enjoy the whole experience perhaps because of the people involved, and wanted to try it again). So I also answered the ad of a young man, George, whose profile expressed some interest in some books I had read, and told him bluntly about my interests. I didn't expect to hear back from him at all, but then Dree wrote me a couple days later and asked about this, as it turned out that she and George were friends and were sharing data about their dating explorations. I said this was a good sign that we should all meet, and suggested a venue a few blocks from my house. It turned out to be closed at the time I suggested, so after we met out front I biked back home as they drove there, and we hung out in my living room.
Both Dree and George were a bit overweight, but young and jovial. They shared that they had few friends their age, partly because of their sexuality--George being gay, and Dree being uncertain about her orientation--and partly because they each recently switched to the same school from elsewhere, and perhaps also just being a little different personality-wise from others, and not fully accepted by their parents, though they each lived at home. I assured them that they could consider my house a safe space, if they felt comfortable with me. We then talked a bit more about sex, and I was again blunt about my interests, also mentioning that if I were to have oral sex with a man I'd feel more comfortable with a woman present, to make the experience feel less completely homosexual, if that makes sense, and more of just a side exploration. Dree said that sounded cool, and George was up for it, so soon I kneeled in front of him to take his dick out of his pants. It was small and soft, but I slowly sucked it up to about 4" long as Dree watched. I asked her to watch as closely as possible, and to talk to me about what she was seeing, dirty if possible. She smiled and laughed, enjoying her role, and asked me if I liked being a cock sucker, and having a man's dick in my mouth, and so forth. I told her she could touch me and she started talking about how sexy my strong bicyclist's legs looked, touching both them and my face a little bit, never touching George's dick (they were not attracted to each other and had no sexual interest in each other at any point), but feeling my muscles move as I sucked him off. I loved this and really got into this amazing satisfaction of a long-held fantasy. It didn't take long for George to grunt a little and start ejaculating into my mouth, which I found a little weird, but for Dree's sake I tried to make it look as pleasant as possible, and swallowed as much of his cum as I could.
After I cleaned up a bit we talked about the experience and I thanked George for his willingness. He then asked if i wanted one, and I decided I'd try it; again, I had accepted bj's from men a couple times, but never came in a man's mouth before. I unzipped on the couch and he sat on the floor to suck me while Dree sat next to me and kissed me, letting my fondle and suck her boobs, and so forth. She looked down a couple times but was mostly focused on my face, and I also found it more erotic to look at her than at George, though the feeling of his mouth was very exciting. Finally I looked deeply into Dree's eyes and she looked back with enormous interest as I starting to cum into George's mouth, gripping her tightly and plaintively gasping with joy.
We talked a bit more while I wound down, and Dree watched my dick much more now as it was still semi-hard and hanging out so I could stay comfortable. I thanked them enormously for what they did for me, and they both said they enjoyed it.
They soon had to go, but they came back a couple times again. First I talked about anal play, and how I wanted to be sucked while my asshole was licked. At first Dree was in front and George behind me, as he was more familiar with ass play. This was Dree's first blowjob but she was very good at it. I turned around for a while and had them reverse roles, but then turned again and Dree finished me by taking a huge spurt of cum across her closed lips (she wasn't quite ready for swallowing yet).
Dree then ame by herself once, and gave me a fantastic blowjob on the same couch, this time taking my load into her mouth. Then they both came back and I was feeling even more frisky, so I asked George if he would penetrate me anally--a completely new experience for me--while Dree sucked on me. Again they were up for that, so I got on top of Dree in a 69 position, but with most of her clothes still on, while George sat on his knees behind me and fucked my lubed-up asshole. It was both painful at times and mind-blowing; I both wanted it to stop every second and wanted it to go on forever. I don't ever remember being as hard as I was in Dree's mouth, as if George's hardness was filing up my own cock and doubling its rigidity. It felt both like forever and just a couple minutes before I began squirting into Dree's mouth, and the orgasmic pulsing of my asshole must have also excited George who then started pumping his semen into me.
Even when I was being fucked I felt like I was totally in control, almost using these two kids for my pleasure. I really enjoyed the experience, but confess that I thought of them at times as my high schooler toys, kids I got to play with occasionally to explore my fantasies. It never went further; Dree never took off most of her clothes or let me go down on or fuck her, and I had no interest in penetrating George. A few months later I moved out of town, and only saw Dree once year later, while George (no longer her friend) vanished altogether. Maybe it wouldn't have lasted had I stuck around, but I am glad I got the chance to sow some of my wilder oats around with these willing friends.
