Straight Male / 39
Four Girlfirends
For a few months last year I had four girlfriends, all unknown to each other. Each filled different roles in my life. This was hardly my ideal; I wished that one woman could be all for me, or barring that, that they knew their limitations and accepted my addressing certain needs with other partners. But this was not so, and I accepted a compromise. In retrospect I was somewhat lucky that they not only never met or found out about each other, but never even really generated a scheduling conflict. But actually each had busy lives and couldn't see me that often, which was part of the problem; I was more available than any of them were, so I could make far more time for each of them than any one of them could, or did, for me. So I was making lemonade out of lemons, so to speak.
I met Amy at a part-time job. She was shy, inexperienced woman 10 years my junior; blonde, very cute, and slightly roundish in face and body. She had barely had any sex, and didn't have any with me. But I loved talking to her, watching movies together, and just hanging out, and after months of tentative dating got to kissing and touching passionately. Sometimes we would this in the back row of a second-run theater in the neighborhood, feeling especially sexy about being sneaky in a semi-public way. At her apartment, we would often get excited, touching and necking with each other passionately, Amy often either closing her eyes to limit the overwhelming sensation, or staring at me with amazement and joy...and then she would call it off saying she needed to control herself. Hence i often went home with some sexual frustration, though in many ways she was the one woman I wanted the most, if only she could open up to me, and her own desires, at a more physical level. She was very intelligent, but a bit socially awkward--as was I, which was certainly part of our mutual attraction. She was a little religious (I was not), but that almost never came up in conversation so I could never tell if it would be a problem, though it was clear that limits on physical activity would be.
I met Glinda through a social club; she had brown hair, an average build, and sharp, penetrating eyes. She pursued me more than I her, but there was definitely mutual attraction. I feared from the beginning that it could not work, however, and we would break up with frustration, the more so the further along we went. She was more religious than I and wanted kids, which I did not. She may not have had too much more experience than Amy did, but was far more forward in talking about sex, and liked to tease me and others. She even talked about a fantasy of flashing truckers on the highway with her generous tits, though I don't know if she ever actually did this. But she made it very clear that she didn't do intercourse or oral sex when dating, possibly not even before marriage although maybe if she was engaged, which she never had been. But she was also very intelligent, and we could talk about many things easily: sex, politics, literature, and philosophy. She was also extremely good at kissing, the best I had met in a long time, and had a unique talent for sucking on my nipples. This usually leaves me indifferent, but something about Glinda's licking sent me into quivering ecstasy. A couple of times she let me jerk off while either sucking her tits, or while she sucked on my nipples, but that's as far as we ever got.
Margaret was a slightly larger woman I met through a dating site. We had less in common, and she had some slightly weird beliefs about alternative medicine which didn't sit well with me. But we enjoyed some movies together, and she made more time to visit me than any of the other women I was with that year. She was also the only one who ever slept with me, and asked to come over once every week or two, always politely checking rather than assuming or insisting up it, though I was usually up for it. The relationship quickly turned physical, though again with limits: she never took off her panties, or even pants I think, but we kissed and I especially loved playing with her enormous breasts. I soon learned that she gave excellent handjobs, and our evening usually ended with me on my back, supported by her legs as she sat upright on the bed, while she jacked me off to a powerful orgasms, often involving some tit-fucking. She had strong hands and arms, and never got tired no matter how long it took, so I loved relaxing and watching her do her work on me, sometimes even continuing our talk about other topics while she gradually brought me off, then getting quiet just toward the end as I focused on the looming orgasm I was about to have all over her hands. The most she would let me do for her was to reach under her pants and rub her to an orgasm, which she enjoyed but didn't usually ask for. Every time I did that though, she would follow this by giving me head, which she otherwise never did. Unfortunately she wasn't very good at blowjobs though, so when she did this I would have to hold her head to pump it up and down on my cock--which fortunately she was ok with--until I came into her mouth. This only happened maybe a third of the time though, so I had far more orgasms than she had, which she seemed fine with. We didn't talk much about sex, and she seemed a little reticent about it so I never found out why she was so shy about having her genitals seen or licked, while being so eager to have a few limited kinds of sex.
I met Brenda also through a social club, indeed the same one I met Glinda through, though they didn't really know each other. We surely had the least in common, but I found her appealing, and she was clearly both sexually active and single at the moment, so I invited her over for a movie one night. She was blonde, but I suspect not naturally so, and had a slightly plump body, not as large as Margaret but still with substantial breasts. During the film we took turns massaging each other's shoulders, and she remove her bra and lifted her shirt so I could do her upper back more thoroughly. Afterwards she lay down on my bed for a more extended massage, and her top clothes quickly came completely off while I rubbed her down with baby oil. She responded very sensually, encouraging me to touch her more gingerly and even to give her light kisses around her back, which drove her wild. I gradually pulled down her loose pants and underwear to reveal the crack of her butt, and licked and kissed her there too, which drove her crazy. I considered licking her ass, but before I got there she got up and said it was my turn; she told me to lie back while she unzipped me and started fiercely sucking on my cock. I laid back and watched her as if I was indifferent or testing her out, though I immediately could tell she was very good at this. It was especially exciting to have her basically insist upon this without my asking her, as I could look at it more objectively and impassively in a sense. After 10 minutes or so I told her that if she didn't stop I was going to cum in her mouth, and she lifted up just long enough to say "I want you to," then plunged back down upon my shaft. She sucked deliciously on me with her slippery but firm lips, and soon I was squirting strongly into her mouth. I complimented her skills, but she said that that wasn't even one of her best blowjobs. I thought this might be false modesty, but a couple weeks later we had a second date, going through the exact same routine of movie, shoulder rubs, back massage, and a blowjob, but her second was indeed noticeably better than the first, though I couldn't say how or why. Brenda never asked for more, and we never kissed or slept together, which was somehow itself exciting as I was basically getting free blowjobs without any effort or commitment, even though I would certainly have given her more sexual contact or pleasure if she asked for it.
I later moved out of town, ending all these relationship, but months later Brenda emailed me out of the blue and, among other things, surprised me with the news that she loved anal sex, and thought about me fucking her ass on her visits, though this was now impossible. I don't know why she didn't ask for that, though perhaps she feared it would have turned me off (it would not have). So now I too fantasize about how that night might have gone if I had pulled her slacks even lower and greased up her asshole to fuck, again without ever kissing her, though I certainly wouldn't have done so without asking if she liked it and would have feared offending her with the question without knowing more. Of course if I did that I would've spent my cum in her butt and missed out on those fantastic blowjobs, so I can't say which I would rather have had (obviously the only good answer is: more of both!)
I usually met Amy at her apartment, while I went to Margaret's apartment just once, and occasionally met Glinda in a public venue; otherwise the women always came to my place, but never close together in time. I think maybe once though I got one of Brenda's blowjobs the day before one of Margaret's sleepovers, and felt deliciously guilty holding her overnight in the bed I got blown on just 24 hours earlier by someone who could suck me so much better than she could.
My ideal? Well, again, all in one woman would be great. Barring that, they should all have gotten along and loved me in their own ways. I would love to have had Brenda sucking my cock while Margaret curdled my balls in her hands and rubbed her tits across me, with Glinda sucking and touching my nipples while Amy kissed me passionately until I came from their mutual ministrations, caressing Amy and Glinda's heads while my genitals were serviced by the larger girls. But that was not to be, so I made the best of things that I could.
I met Amy at a part-time job. She was shy, inexperienced woman 10 years my junior; blonde, very cute, and slightly roundish in face and body. She had barely had any sex, and didn't have any with me. But I loved talking to her, watching movies together, and just hanging out, and after months of tentative dating got to kissing and touching passionately. Sometimes we would this in the back row of a second-run theater in the neighborhood, feeling especially sexy about being sneaky in a semi-public way. At her apartment, we would often get excited, touching and necking with each other passionately, Amy often either closing her eyes to limit the overwhelming sensation, or staring at me with amazement and joy...and then she would call it off saying she needed to control herself. Hence i often went home with some sexual frustration, though in many ways she was the one woman I wanted the most, if only she could open up to me, and her own desires, at a more physical level. She was very intelligent, but a bit socially awkward--as was I, which was certainly part of our mutual attraction. She was a little religious (I was not), but that almost never came up in conversation so I could never tell if it would be a problem, though it was clear that limits on physical activity would be.
I met Glinda through a social club; she had brown hair, an average build, and sharp, penetrating eyes. She pursued me more than I her, but there was definitely mutual attraction. I feared from the beginning that it could not work, however, and we would break up with frustration, the more so the further along we went. She was more religious than I and wanted kids, which I did not. She may not have had too much more experience than Amy did, but was far more forward in talking about sex, and liked to tease me and others. She even talked about a fantasy of flashing truckers on the highway with her generous tits, though I don't know if she ever actually did this. But she made it very clear that she didn't do intercourse or oral sex when dating, possibly not even before marriage although maybe if she was engaged, which she never had been. But she was also very intelligent, and we could talk about many things easily: sex, politics, literature, and philosophy. She was also extremely good at kissing, the best I had met in a long time, and had a unique talent for sucking on my nipples. This usually leaves me indifferent, but something about Glinda's licking sent me into quivering ecstasy. A couple of times she let me jerk off while either sucking her tits, or while she sucked on my nipples, but that's as far as we ever got.
Margaret was a slightly larger woman I met through a dating site. We had less in common, and she had some slightly weird beliefs about alternative medicine which didn't sit well with me. But we enjoyed some movies together, and she made more time to visit me than any of the other women I was with that year. She was also the only one who ever slept with me, and asked to come over once every week or two, always politely checking rather than assuming or insisting up it, though I was usually up for it. The relationship quickly turned physical, though again with limits: she never took off her panties, or even pants I think, but we kissed and I especially loved playing with her enormous breasts. I soon learned that she gave excellent handjobs, and our evening usually ended with me on my back, supported by her legs as she sat upright on the bed, while she jacked me off to a powerful orgasms, often involving some tit-fucking. She had strong hands and arms, and never got tired no matter how long it took, so I loved relaxing and watching her do her work on me, sometimes even continuing our talk about other topics while she gradually brought me off, then getting quiet just toward the end as I focused on the looming orgasm I was about to have all over her hands. The most she would let me do for her was to reach under her pants and rub her to an orgasm, which she enjoyed but didn't usually ask for. Every time I did that though, she would follow this by giving me head, which she otherwise never did. Unfortunately she wasn't very good at blowjobs though, so when she did this I would have to hold her head to pump it up and down on my cock--which fortunately she was ok with--until I came into her mouth. This only happened maybe a third of the time though, so I had far more orgasms than she had, which she seemed fine with. We didn't talk much about sex, and she seemed a little reticent about it so I never found out why she was so shy about having her genitals seen or licked, while being so eager to have a few limited kinds of sex.
I met Brenda also through a social club, indeed the same one I met Glinda through, though they didn't really know each other. We surely had the least in common, but I found her appealing, and she was clearly both sexually active and single at the moment, so I invited her over for a movie one night. She was blonde, but I suspect not naturally so, and had a slightly plump body, not as large as Margaret but still with substantial breasts. During the film we took turns massaging each other's shoulders, and she remove her bra and lifted her shirt so I could do her upper back more thoroughly. Afterwards she lay down on my bed for a more extended massage, and her top clothes quickly came completely off while I rubbed her down with baby oil. She responded very sensually, encouraging me to touch her more gingerly and even to give her light kisses around her back, which drove her wild. I gradually pulled down her loose pants and underwear to reveal the crack of her butt, and licked and kissed her there too, which drove her crazy. I considered licking her ass, but before I got there she got up and said it was my turn; she told me to lie back while she unzipped me and started fiercely sucking on my cock. I laid back and watched her as if I was indifferent or testing her out, though I immediately could tell she was very good at this. It was especially exciting to have her basically insist upon this without my asking her, as I could look at it more objectively and impassively in a sense. After 10 minutes or so I told her that if she didn't stop I was going to cum in her mouth, and she lifted up just long enough to say "I want you to," then plunged back down upon my shaft. She sucked deliciously on me with her slippery but firm lips, and soon I was squirting strongly into her mouth. I complimented her skills, but she said that that wasn't even one of her best blowjobs. I thought this might be false modesty, but a couple weeks later we had a second date, going through the exact same routine of movie, shoulder rubs, back massage, and a blowjob, but her second was indeed noticeably better than the first, though I couldn't say how or why. Brenda never asked for more, and we never kissed or slept together, which was somehow itself exciting as I was basically getting free blowjobs without any effort or commitment, even though I would certainly have given her more sexual contact or pleasure if she asked for it.
I later moved out of town, ending all these relationship, but months later Brenda emailed me out of the blue and, among other things, surprised me with the news that she loved anal sex, and thought about me fucking her ass on her visits, though this was now impossible. I don't know why she didn't ask for that, though perhaps she feared it would have turned me off (it would not have). So now I too fantasize about how that night might have gone if I had pulled her slacks even lower and greased up her asshole to fuck, again without ever kissing her, though I certainly wouldn't have done so without asking if she liked it and would have feared offending her with the question without knowing more. Of course if I did that I would've spent my cum in her butt and missed out on those fantastic blowjobs, so I can't say which I would rather have had (obviously the only good answer is: more of both!)
I usually met Amy at her apartment, while I went to Margaret's apartment just once, and occasionally met Glinda in a public venue; otherwise the women always came to my place, but never close together in time. I think maybe once though I got one of Brenda's blowjobs the day before one of Margaret's sleepovers, and felt deliciously guilty holding her overnight in the bed I got blown on just 24 hours earlier by someone who could suck me so much better than she could.
My ideal? Well, again, all in one woman would be great. Barring that, they should all have gotten along and loved me in their own ways. I would love to have had Brenda sucking my cock while Margaret curdled my balls in her hands and rubbed her tits across me, with Glinda sucking and touching my nipples while Amy kissed me passionately until I came from their mutual ministrations, caressing Amy and Glinda's heads while my genitals were serviced by the larger girls. But that was not to be, so I made the best of things that I could.
