To finish the story, the second hook up with a cute and very horney 50 year old redhead divorcie, that occurred after covid started, an untypical tinder experience that involved some delay and sexy zoom meetings, as we figured out that we we adequately quaranteened and were likely to be safe.
After satisfying each other, 2x for me and several for her, she made dinner for me and we talked quite a bit. She had been married for 20 years, had never had kids (career decision), and despite her being an interesting person, cute, and very hot and very vocally multiorgasmic (something I really like) hubby had found a younger woman, so she had hardly had sex, except with her vibrator, in nearly a year, and not much in 2 years.
An hour or two later, the conversation turned more sexy and our hands began to roam. It turned out that she admitted being an anal virgin. She liked anal play with fingers, and had always wondered about it, but her hubby had been very big, and they never succeeded penetrating her with more than fingers. With that conversation, I figured that round 2 was likely to be more kinky. Anyway, kissing led to our hands roaming, then we wound up in a nice 69, which was nice because her lips were totally shaved. She just rolled along, vocally cumming several times as I licked her bright pink, and very juicy pussy. I also took the opportunity to explore her tight, pink butt hole with my finger, which we gave every indication of liking, a lot. Between her vocalizations, she paid good attention to my cock.
I had found, in our previous encounters a few days before and earlier that day, that she liked to sit on my cock and rude me while I kissed either her mouth or sucked her very pale nipples. However, as we ended or 69, she rolled onto her back, and pulled her legs up to her shoulders and said "take my ass".
We didn't have any lube, but she was really wet from our 69, so I slowly rubber the head of my cock into the opening of her pussy, trying to transfer her juices to her butt. She was excited enough, and orgasmic enough that this brought her off again.
With her bottom very wet, I put my cock against her anal opening, and gently pushed. She told me, a couple of times "go slow", but eventually my cock found it's way into her. After a few progressively deeper thrusts, and a bit of waiting I began to stroke into her. It took a minute or two until her face went from a little uncertain to very excited, and she begain saying"oh, yeah, oh yeah". Now, anal sex, because it is a little forbidden, and the idea of taking her cherry was exciting, and because she was very tight, I didn't last long, but I did last long enough that she got to the finish line.
Afterwards, she said it was as good as she expected, but that she could never have done it with someone as big as her ex. Apparently whatever I brought to the bedroom, a healthy average sized cock, was just about right.
I wound up spending the night, with a few other pleasing activities, although we were both becomming a little sore.
Now, this stort is about Tinder, which is designed for quick hookups, and mostly designed for a younger demographic (hopefuly some of you have experiences with Tinder), but I did meet her via Tinder, and it has been a couple of satisfying adventures. At least during the covid thing, I expect that we will hook up with some frequency, as she is very hot. After that, who knows.
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