Straight Male / 55
Fling With Permission
My wife Jessica and I just took a trip out west, and along the way I reconnected with a woman I rented a room from years earlier in a different state. Peggy was a beautiful dusty blonde, with ever a shapely face, now aging gracefully, but had always had relationship problems. She admitted she had mental health issues at times, though I never say signs of that, but they contributed to stability issues even though she had many long-term friends. I always secretly wanted to fuck her, but never got the chance. I knew we weren't really each other's type, but I always hoped there would be some change for a fling even if nothing long term could come of it.
When they met, Jessica identified with Peggy immediately and became friends, finding all kind of commonalities in their mutual cynicism, sarcasm, and issues with various people who brought them down, as well as delight in certain kinds of humor. She's always been accommodating of my needs and we've sometimes talked about my getting on with another lady, especially as a threesome. Well, Peggy causally mentioned that she was totally straight, so that was out, but this wasn't an absolute barrier. At one point she mentioned having a dry spell dating and missing some dick, and Jessica pretty quickly suggested me as a "no strings attached" option. Peggy laughed but quickly saw that she was serious, as was I, and while this seemed embarrassing at first, later that evening she confessed that this might work, though it had to be just the two of us. Jessica was fine with that and so I went to our rented bedroom with Peggy.
We kissed and fondled a little, but when I asked if she was ready to fuck she quickly said she was comfortable skipping the preliminaries and getting right to it. With a no-nonsense style she got naked and with only a quick compliment on my hardening dick, which she gave a little tug, she got on her knees doggy style. Her pussy looked puffy, furry, and soft, and I felt very animalistic approaching her from behind, I needed no help getting hard and sliding into her wet hole. Grabbing her ass cheeks and thrusting in, hearing her moan, and seeing her cute, tiny asshole in the middle of a luscious round butt, was driving me wild. I told her that I was afraid I would cum too quickly, and she asked if I ever stayed hard after cumming. I said I might with the right situation, and she quickly pulled away and turned around to suck on my dick. This was amazing and unexpected, even more so when she asked where I wanted to cum. "On your face?" "OK then," she grinned as if now in possession of a long-unknown secret, like she had my sexual number after all this time. Soon she had me about to explode in her mouth, and pulled back to jerk me off all over her pale face. Several white streams went from her forehead to her cheeks, and she made sure to get a good bit right across her lips.
After a few more slow pulls to get more cum out of me and wipe it onto her face, she laid back and told me to fuck her again. I slid back inside, missionary style this time, and she crooned in appreciation as I gazed at her cum-coated face and her beautiful delicious tits, which I fondled and occasionally bent down to suck. This was the perfect view to keep me hard, and I lasted much longer this time, enough for her to have at least one very strong orgasm and a few minor shakes of pleasure. She kept saying things like "this is so good, I'm amazed we're doing this." I too found it remarkable that we could connect this way after all this time. Perhaps it could only happen on vacation when I had another partner, so we knew there was little risk of entanglement.
Eventually I tired and pulled out, but I told her it wasn't over, and bent down to eat her out. She liked this a bit, but told me she was exhausted and couldn't come again, so I quit and we cuddled a while, after she finally wiped her face clean. Eventually we dressed and announced to Jessica our success, getting congratulations from her on pleasing each other while she got some work done. She's a little less sexual than I so this was a wonderful win-win experience for us all. We're now over a thousand miles from Peggy, but I know we'll be more taking trips out west again before too long....
When they met, Jessica identified with Peggy immediately and became friends, finding all kind of commonalities in their mutual cynicism, sarcasm, and issues with various people who brought them down, as well as delight in certain kinds of humor. She's always been accommodating of my needs and we've sometimes talked about my getting on with another lady, especially as a threesome. Well, Peggy causally mentioned that she was totally straight, so that was out, but this wasn't an absolute barrier. At one point she mentioned having a dry spell dating and missing some dick, and Jessica pretty quickly suggested me as a "no strings attached" option. Peggy laughed but quickly saw that she was serious, as was I, and while this seemed embarrassing at first, later that evening she confessed that this might work, though it had to be just the two of us. Jessica was fine with that and so I went to our rented bedroom with Peggy.
We kissed and fondled a little, but when I asked if she was ready to fuck she quickly said she was comfortable skipping the preliminaries and getting right to it. With a no-nonsense style she got naked and with only a quick compliment on my hardening dick, which she gave a little tug, she got on her knees doggy style. Her pussy looked puffy, furry, and soft, and I felt very animalistic approaching her from behind, I needed no help getting hard and sliding into her wet hole. Grabbing her ass cheeks and thrusting in, hearing her moan, and seeing her cute, tiny asshole in the middle of a luscious round butt, was driving me wild. I told her that I was afraid I would cum too quickly, and she asked if I ever stayed hard after cumming. I said I might with the right situation, and she quickly pulled away and turned around to suck on my dick. This was amazing and unexpected, even more so when she asked where I wanted to cum. "On your face?" "OK then," she grinned as if now in possession of a long-unknown secret, like she had my sexual number after all this time. Soon she had me about to explode in her mouth, and pulled back to jerk me off all over her pale face. Several white streams went from her forehead to her cheeks, and she made sure to get a good bit right across her lips.
After a few more slow pulls to get more cum out of me and wipe it onto her face, she laid back and told me to fuck her again. I slid back inside, missionary style this time, and she crooned in appreciation as I gazed at her cum-coated face and her beautiful delicious tits, which I fondled and occasionally bent down to suck. This was the perfect view to keep me hard, and I lasted much longer this time, enough for her to have at least one very strong orgasm and a few minor shakes of pleasure. She kept saying things like "this is so good, I'm amazed we're doing this." I too found it remarkable that we could connect this way after all this time. Perhaps it could only happen on vacation when I had another partner, so we knew there was little risk of entanglement.
Eventually I tired and pulled out, but I told her it wasn't over, and bent down to eat her out. She liked this a bit, but told me she was exhausted and couldn't come again, so I quit and we cuddled a while, after she finally wiped her face clean. Eventually we dressed and announced to Jessica our success, getting congratulations from her on pleasing each other while she got some work done. She's a little less sexual than I so this was a wonderful win-win experience for us all. We're now over a thousand miles from Peggy, but I know we'll be more taking trips out west again before too long....
- That's Juicy! 30
- Remove It! 2
