Good for Seconds and Thirds

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This story is a sequel to “Peeping by the Pool” and describes what happened that night.

Ryan went to bed but he had no thought of sleeping, at least not for a while. His mind was too occupied with thoughts of Marian, the voluptuous woman who lived next door. That afternoon, peeping through the hole he had cut in the storage shed in the back yard, he had seen her sunbathing, totally nude, and masturbating by her swimming pool. It had been, by far, the most erotic thing he had ever seen. He was acquainted with a few girls or women who were probably better looking, maybe even sexier, but he had never seen their tits or pussies.

He knew he never would, either. As a red-haired 18 year old high school dropout, short and fat and clumsy, no female would ever approach him with romantic ideas. To make it worse, he was so painfully shy that even the thought of approaching a girl made him tremble and break out in a cold sweat. One of his most painful memories was a girl in his high school looking down her nose and laughing at him when he dared to approach her, making his stomach clench so tightly that he had to run into the boys’ room to vomit. He had dropped out of school that same day, unable to stand the ridicule, which had begun immediately.

But he had seen Marian’s tits and pussy. He had seen them just that afternoon from a distance of thirty feet. Not only had he seen these private parts, he had seen her playing with them, stroking her tits and squeezing her nipples and fucking her pussy with her finger. He had already canlı bahis şirketleri jacked off twice, while he was watching her, but the thought of what he had seen was giving him a hard-on again.

After cumming into his handkerchief twice that afternoon, Ryan dropped it into the dirty clothes hamper and got a clean one from his dresser. With thoughts of the sexy Marian swirling through his mind, he wrapped the handkerchief around his cock and stroked it tentatively. It felt good. The feeling he got was even better than it had been the first time that afternoon when he had been so turned on by what suddenly presented itself to him that he had hardly pumped his cock at all before cumming. It felt better than the second time too because his cock hadn’t been fully hard that time, but the sight of Marian finger-fucking herself was so hot that he needed to jack off again.

The night was warm so Ryan was covered only by a sheet, and he pushed that down below his knees. His cock was protruding through the fly of his underwear but he decided to take off the garment so he would be just as naked as Marian had been. That thought, of something in common with her, sent a pleasurable thrill through his body. Jacking off was more fun when he was naked anyhow, so he peeled off his shorts. Unencumbered by clothing, he lay on his back, slowly stroking his cock up and down with visions of his naked neighbor frolicking through his mind.

The thought he had entertained earlier entered his mind again. Some of his friends had canlı kaçak iddaa told him how women in their forties, like Marian, who lived alone, like Marian did, were always looking for young men to fuck them. Some of them bragged that they had done that with a lot of older, lonely women, and it had been so much fun, and the women had been so happy. Ryan would have been willing to provide that service for his neighbor if she were only to ask him. Even though he was short and fat and homely, it shouldn’t matter to her. She was, after all, old enough to be his mother. Since he was right next door, he couldn’t imagine why she didn’t invite him into her home on some pretense, and then into her bed. Surely, she must know he could give her more than she could ever get from finger-fucking herself.

“I could really give it to her and make her feel good,” he told himself. Maybe it would be so good she would want me to come over a couple of times a week. Maybe she would even want to suck me off!” Ryan had heard those same friends talking about that, and how some of the older women liked to do it, and how much fun it was. He knew for sure he wanted to find out.

The thought of fucking his voluptuous neighbor and maybe being sucked off by her, combined with the vivid memory of her naked body was making Ryan’s cock throb in his hand. The intense pleasure was spreading through his body as he increased the speed of his hand. He was panting and his heart was pumping hard from his exertions but it felt so good! Everything felt so good, canlı kaçak bahis especially his cock in the hand that he imagined was actually Marian’s pussy or her mouth.

The muscles in his body seemed to be pulling everything toward his hard cock as he felt the pleasure welling up, concentrated there. He sighed and his body jerked as he climaxed, his semen gushing out and quickly soaking the handkerchief he was using. Completely relaxed, satisfied but still knowing something was lacking, Ryan lay quietly until his breathing and heart rate returned to normal and his erection shriveled.

When he was ready, he went to the bathroom and urinated, flushing out the cum that had remained in his cock. After using it to wipe himself off, the wet handkerchief joined the previously used one in the laundry hamper. Ryan returned to bed.

He was ready for sleep, but before he dropped off, he decided on a course of action. It just wasn’t right that he should have to jack off like he just had, and Marian should not have to get herself off with her fingers. There was so much they could do for each other, and he wished she knew it as well as he did. He was just going to have to figure out a way to tell her, and he would have to do it soon.

Thank you for reading this story. I hope you had more fun than Ryan did and as much as he hopes to have with Marian. I like writing stories on this site but I like it a lot more when I know that people are reading and enjoying them. That’s why I always appreciate it when readers take the time to express their opinions by voting. Like most other writers on Literotica, I practically live for feedback from readers, either public comments or email to me. Such comments help me to write more and better stories, and I respond to them whenever I can.