Straight Male / 54
Hot Girl In Co-op
I had sex with just one woman as a university undergraduate, then started dating another woman, Lana, who was very cute but had very conservative ideas and feelings about sex. We slept together platonically every few weeks, and kissed passionately, but we never took off our underwear and she got sharp with me the few times we even talked about the possibility of sex.
The next year I moved a couple hundred miles for graduate school, and soon moved into a housing coop near campus. It was very politically liberal, with nudity allowed in public areas and was strongly pro-LGBT. Still, more than half the residents were heterosexual undergraduates, with a few graduate students.
About mid-way through the year I got invited to a massage session by Kim, one of the younger women there, she and her closest friend Hanna also invited a second man, Jim, from outside the coop, and soon we were all naked rubbing each other with peanut oil. After a while Kim started talking about how oil was also good for anal sex, and how it was safe with younger men and couldn't lead to pregnancy, etc. Kim then said something to Hanna I didn't quite catch, and the two of them excused themselves to the bathroom for about 15 minutes. When they came back the more experienced Kim said that they were both ready for anal sex, though warned us that it was Hanna's first time. It was my first time too, though Jim and Kim had both done this before with other people. So the starting pairs were Kim and I, and Jim and Hanna, but after a few minutes we all switched--I'm guessing because Hanna had told Kim she was more interested in me. Both Kim and Hanna had tight assholes, but positioned themselves on all fours for easier entry, and I loved feeling my cock go into their butts. I'm pretty sure Hanna didn't orgasm, but the rest of us all did, and Kim's was particularly expressive and vocal, as she told Jim to fuck her butt over and over while she gasped.
Well, that was a fun night, but it wasn't long before Kim was asking me over to her room one or more nights a week when she was feeling horny, I think just because I was available. We got into a routine, where I would fuck her ass, with her either on all fours, or me in a chair or edge of a bed, her sitting on me and facing away so she could slide her ass up and down around my cock while she fingered herself. Every time she orgasmed I could feel her asshole clench and that always led me to orgasm. More than once I fucked her ass doggy style, and just held still for several minutes while she squirmed and developed her orgasm, then came when I started to feel her butt clench around my dick.
I never told Lana about this, even though she once came to visit, though she actually stayed with other friends in town and wouldn't even stay overnight with me, though we had done that many times the previous year. I felt alone, and while I enjoyed her company more, I didn't want to stop fucking Kim. Kim and I didn't have much in common other than the sex, and often it felt mechanical, but it was still good. Hanna knew we were fucking, and didn't seem to care. She even came to watch us once, but didn't participate. I eventually got my degree and moved out of town for a job, and other than a few cursory messages lost all contact with the coop girls. But I never regretted this initiation.
The next year I moved a couple hundred miles for graduate school, and soon moved into a housing coop near campus. It was very politically liberal, with nudity allowed in public areas and was strongly pro-LGBT. Still, more than half the residents were heterosexual undergraduates, with a few graduate students.
About mid-way through the year I got invited to a massage session by Kim, one of the younger women there, she and her closest friend Hanna also invited a second man, Jim, from outside the coop, and soon we were all naked rubbing each other with peanut oil. After a while Kim started talking about how oil was also good for anal sex, and how it was safe with younger men and couldn't lead to pregnancy, etc. Kim then said something to Hanna I didn't quite catch, and the two of them excused themselves to the bathroom for about 15 minutes. When they came back the more experienced Kim said that they were both ready for anal sex, though warned us that it was Hanna's first time. It was my first time too, though Jim and Kim had both done this before with other people. So the starting pairs were Kim and I, and Jim and Hanna, but after a few minutes we all switched--I'm guessing because Hanna had told Kim she was more interested in me. Both Kim and Hanna had tight assholes, but positioned themselves on all fours for easier entry, and I loved feeling my cock go into their butts. I'm pretty sure Hanna didn't orgasm, but the rest of us all did, and Kim's was particularly expressive and vocal, as she told Jim to fuck her butt over and over while she gasped.
Well, that was a fun night, but it wasn't long before Kim was asking me over to her room one or more nights a week when she was feeling horny, I think just because I was available. We got into a routine, where I would fuck her ass, with her either on all fours, or me in a chair or edge of a bed, her sitting on me and facing away so she could slide her ass up and down around my cock while she fingered herself. Every time she orgasmed I could feel her asshole clench and that always led me to orgasm. More than once I fucked her ass doggy style, and just held still for several minutes while she squirmed and developed her orgasm, then came when I started to feel her butt clench around my dick.
I never told Lana about this, even though she once came to visit, though she actually stayed with other friends in town and wouldn't even stay overnight with me, though we had done that many times the previous year. I felt alone, and while I enjoyed her company more, I didn't want to stop fucking Kim. Kim and I didn't have much in common other than the sex, and often it felt mechanical, but it was still good. Hanna knew we were fucking, and didn't seem to care. She even came to watch us once, but didn't participate. I eventually got my degree and moved out of town for a job, and other than a few cursory messages lost all contact with the coop girls. But I never regretted this initiation.
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