The following took place in college. I was 21; she was a 46 year-old divorcee, and a commuter student at my college. We were both campus tour guides for high school seniors visiting the campus. During the training to become Official Campus Tour Guides, we chatted each other up. Neither of us were a part of any of the Greek Life cliques, so we had little more than each other to talk to. She was still quite attractive, but there was no mistaking that she was in her mid-40s. 5'6, sandy blond short bob haircut, carried the extra weight that motherhood and life sometimes packs on some housewives.
One evening, we have dinner together at the campus diner. Somehow we end up back in my room. During this whole time, I learn that there's not many topics that are off-limits for her. She was quite frank about not just her divorce, or raising her 13 year-old son by herself, but about sex. It was kind of refreshing, because girls my age would discuss sex, but their hang-ups would inevitably surface. And here was a woman almost my mother's age discussing hand jobs and eating pussy in a wildly uninhibited manner.
Anyways, we're in my dorm room, which I had to myself for most of the semester. She asks about some CDs in my music collection. I go over to where she's looking. She's positioned herself so that I have to lean across in front of her, and because my elbow only bends in one direction, my arm is pushing right into her breast. I say something with the intention that it will diffuse and brush aside the rudeness of a surreptitious grope. I'll never forget the wicked smile she smiled, saying, "Its okay. It feels nice." I gotta admit, it did feel nice. So I took my time. Perhaps a bit too much time. "You can use your hand, you know." I said, "Is that an invitation, or a request?" to that she replied, "If it were a request, I'd ask you to use your hand." I turn to face her, and we both lean in to each other for a liplock. And I took up the invitation. But only from outside her sweater. And it didn't go farther than that. Not that night.
About a month later, I see her on campus kind of late. She asks if she can stay in my room for the night so she wouldn't have to drive all the way home (her son was already going to be spending the night at a friend's house). I guess so, I said, not sure what the night would bring. She was wearing a pretty low cut v-neck tee under a flannel for warmth, and a long gypsy skirt, which she knew I was a sucker for.
It wasn't long after getting to my room that we picked up where we left off. Her hand went down my pants while I got her naked above the waist. Her breasts were full, round and gorgeous DDs with the thickest nipples I had ever seen. They were as big around as the tip of my index finger. And, apparently, VERY sensitive. She told me that she has come just from having her nipples played with. I was game to try.
The skirt came off revealing a lack of panties. "Oh, I never wear any." For some reason, I found that to be so much hotter than a girl my age going commando, just for the occasion. She had a thin patch of blond-ish pubic hair that did nothing to obscure the slightly parted lips. I wanted to sink my cock into that so badly, but I had no condoms (trying to keep this non-fiction, guys). After manually stimulating her to a very wet orgasm, and while she was still laying on my bed with legs open, she asks, "Can I watch you beat off?", to which I obliged within about 4 pumps to her great delight.
The greatest part was the next morning, she was very agreeable, certainly for her own reasons, to sneaking out of the building so as not to raise eyebrows.
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