Peeping by the Pool

After dropping out of high school at the age of 18, Ryan had nothing better to do than hang out, peeping through the fence that separated his families property from the neighbor's back yard. The best thing about peeping was the neighbor herself, a tall, voluptuous woman in her forties. He knew her name was Marian and she was divorced, lived by herself in the house and spent a good part of almost every summer afternoon sunning herself by her pool or swimming. Seeing Marian in her bathing suit was quite erotic in itself, but sometimes she would swim or sunbathe topless and when she did, it would make all of Ryan's time and trouble completely worth his while, at least to his way of thinking.

At first, he had tried to peep directly through the fence, until he realized that he was visible to her when he did that. The fence was chain link with laths woven into it and, although it gave him an excellent view of the lounge that Marian used, she could see him too, and would quickly leave if he was next to the fence.

Ryan had solved that problem by setting up a peeping station in the wooden shed that his parents used to store the lawn mower and other lawn and garden tools. Using a hole saw, he had cut a small, round hole in the side that abutted the fence, giving him a perfect view of the lounge. When he was not peeping, the hole was plugged with the small piece of wood that had been removed. It was directly behind where the lawnmower was usually placed so that if anybody happened to glance at the interior of the shed, the plugged hole would not be visible.

It was a hot afternoon and Ryan expected Marian to use the lounge and maybe the pool so he went to the back yard and walked straight to the shed door. By approaching like that, nobody could see him through the fence. He entered the shed, closing the door behind himself, and got as comfortable as he could before removing the plug from the hole and peering through.

He smiled at the sight that met his eyes. There she was, thirty feet away, standing by the lounge in the bathing suit that covered her large breasts and shapely hips and ass. Her hair was long and dark brown and her visible skin was well tanned. Ryan was well aware from previous peeping that the skin hidden by the top of the two piece suit was much lighter, and he hoped to see some of it that day. What he really wanted was for all of the untanned skin to be on display but that had never happened and he didn't even dare hope it ever would. Even the thought of the possibility made his cock start to stiffen; he decided that, whether he saw a tit show or not, he would probably jack off just before leaving the shed.

At first, nothing happened. The object of his surveillance simply lay on her back, her eyes covered by dark glasses. Having nothing better to do, Ryan waited patiently at his station. After a few minutes, his patience was rewarded as his sexy neighbor sat up, reached behind herself and unhooked her bathing suit top. As he watched avidly, she peeled off the garment and fondled her breasts briefly, giving Ryan a clear view of the prettiest tits he had ever seen. She only sat up for a few seconds before lying on her back again but it was enough to give him a hard-on as stiff as any he had ever had.

His cock almost seemed to be trying to rip through his pants at the sight of the sexy woman lying down with her big, firm tits pointing into the air. Ryan quickly unzipped his fly and pulled out his cock. As he watched her resume caressing her breasts and playing with her nipples, he fantasized being there with her. He had heard from some of his buddies how older divorced women like Marian were always trying to get young guys like him to fuck them but so far she had resisted the urge they said she would have. He would be ready when she finally gave in to what he thought of as her needs but until then, jacking off while staring at her tits was what he had to settle for. He knew he would cum, maybe more than once, and he wrapped his handkerchief around his cock so it didn't squirt onto the floor and leave sticky, smelly evidence of what he had been doing.

The object of Ryan's lust didn't stay on her back very long. Instead, she turned onto her side facing toward him, draping her upper arm over the side of her head while her other hand continued fondling her tits. He wondered if she was actually masturbating because he couldn't understand why a woman would do such a thing when there was a young stud next door who would be willing to fuck her if she would only ask him. Besides, he had heard that women used a fake cock to do that.

After only a few minutes of lying on her side, she sat up again and got to her feet. Ryan relished the view again of her breasts, especially the way they swayed as she started pushing down the tight-fitting bottom part of her bathing suit. After he realized what she was doing, Ryan's eyes were riveted on the paler skin that was being exposed. As the garment was pushed clear of her hips and ass and allowed to fall to the ground, his hand pumped harder. Staring at the sexiest thing he had ever seen, the tits and pussy of his voluptuous neighbor, completely naked and standing thirty feet away, Ryan ejaculated into his handkerchief.

His heart and his breathing calmed back down after a few minutes and Ryan returned to his spy hole. Marian was lying on her right side again, still naked, playing with her tits again. As he watched, her hand moved from there to her pussy, reaching down almost between her legs and starting to rub. Oh! How he wished his cock could somehow trade places with her fingers, even for a few seconds. Open-mouthed, he watched what she was doing and how her big tits and the rest of her body were squirming in unison with the movements of her supremely lucky right hand. She really was masturbating, he realized, and he quietly railed at her for depriving both him and herself of the great sex they could be sharing.

At 18 years of age, Ryan had a fast recovery period, especially when he was gazing at something as erotic as sexy Marian, naked and playing with her pussy. His cock wasn't fully hard yet but it was hard enough for him to wrap his handkerchief around it again and start stroking while peering intently through the hole in the shed wall. As he watched and stroked, the woman on the lounge rolled over onto her back to continue her fun. Seconds later, both hands were at her pussy and she was rocking back and forth, her tits bouncing, while she pleasured herself.

Ryan was doing the same thing for himself, his cock fully erect and his right hand almost a blur as he pumped back and forth. The view through the peephole got better and better as Marian leaned forward and Ryan could tell she had started thrusting her fingers in and out of her pussy. Not only could he see her, he could hear her almost as well through the loosely fitted boards. The sound had been going on for some time but at first, he hadn't known what it was, until he realized she was moaning, like what some of his friends had told him women did when they were almost ready to cum. Despite the powerful visual and aural stimulus, cumming for the second time in such a short period would take longer, even for a young man. Ryan didn't care; he was having too much fun to want to hurry it anyhow.

"Uh! Uh! Uh!" Marian whimpered suddenly and loudly. Seconds later, she arched her back and her body seemed to spasm. After that, her movements stopped and she lay quietly. Ryan was not at all knowledgeable on female sexuality but he was quite sure that she had just cum. Even as he was wishing that it had been his cock that had caused that wonderful event, he felt his pleasure welling up inside his body and overflowing into his groin. Abruptly, he climaxed, grunting once and again filling his handkerchief with semen.

Ryan considered that day to have been quite possibly the best in his life. Although he was probably through jacking off until he went to bed that night, he had enjoyed two of his best climaxes ever. Even better, the sight of his voluptuous neighbor buck-naked and seeing and hearing her cum from playing with her pussy and finger-fucking herself would give him something to fantasize about for many nights of jacking off. Life felt good to Ryan.

*

Thank you for reading this story. I hope you had as much fun as Ryan did, and as he expects to have in the future. For the other side of what I described, see "Fingers by the Pool" which should be posted within a day of this story.

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.