Tim's Peeping Education

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He spies on an older woman gets more than he expected.
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A thrill coursed through his body, and he pedaled even faster. He was really going to do it, if he didn’t lose his nerve and chicken out. Tim turned onto the right street and his pulse quickened just from the sight of his friend’s house. Pulling up in front, he looked around to see if anyone was watching. Seeing nobody, he let himself through the gate and into the backyard. If challenged, he would say that he was there to swim with Matt, although he didn’t expect it to be necessary. He knew that there wasn’t anyone home.

Quietly, he closed the gate behind him and parked his bike against the empty house. His heart was beating in his chest as he walked across the back lawn toward the neighbor’s fence. Silently, he crouched down and peeked through the knothole that Matt had shown him. As expected, a towel was laid out next to the neighbor’s pool, along with a pair of sunglasses and a battery-powered CD player. Tim checked his watch- according to Matt, the show was just about to start. His friend said that it happened at roughly the same time on both Saturday and Sunday.

Upstairs, Lauren was just about to return to her towel when something caught her eye out the bedroom window. Looking closer, she saw a teenager walking across her neighbor’s backyard toward her fence. She started to look away, but then remembered that the Gilmans were on vacation, so there wouldn’t be anyone home. Looking again, she thought the kid looked familiar, like one of Matt Gilman’s friends. Yeah, she thought, I’ve seen him around. Her sense of concern dissipating, she became curious about what he was doing over there. He went over to her fence and hunkered down, moving his head around like he was trying to....look through the fence. Still curious, she looked to her own yard for explanations, like a lost baseball or something. She didn’t see anything like that. The only thing anywhere near him on her side of the fence was her towel and tanning stuff, but he couldn’t be interested....

The thought made her lightheaded, so she looked closer. Yes, he looked like he was getting comfortable at whatever hole or crack he was looking through, and he kept looking behind him nervously, like he was doing something he shouldn’t. Well.... a smile flashed across her lips as a thrill ran though her. So he wanted a show, did he?

Tim froze and held his breath as he heard the back door open and close. Matt’s neighbor walked out to the towel, and Tim quietly gasped for air, his eyes widening. In all their talks, Matt always lamented the fact that his neighbor always wore a one-piece swimsuit, and not something more exotic. This beauty, that Tim had only seen in polite company, fully dressed, was walking toward him in the skimpiest bikini he had ever seen. His girlfriend would never wear something so revealing, despite his pleas. He struggled to remember her name as his mind whirled in circles and his swim trunks became tight. Remembering her name seemed really important, although he didn’t know why. Lauren. Lauren was her name. His heart was beating so hard that he was sure she could hear it from her tanning spot, fifteen feet away. Thankfully, she turned on the CD player beside her. It was something relaxing, and she lay down on her back, spreading her long brown hair out above her. She put on the sunglasses and lay still. He eyed her closely, the hair, the face, the wonderfully upthrust breasts, trim belly, softly curved hips, shapely legs, and back to the barely-covered crotch. His breathing deepened, and his hand strayed to the hardness in his swim shorts.

After ten minutes or so, she turned over, presenting a new visual feast to his hungry eyes. He loved the way her breasts squished out from under her, admired the toned back, dwelled long on the perfect ass, and mentally ran his hands all the way down her legs to those delicious toes. He remembered the first time he met her. He and Matt had been tossing a football around in the street, and, when challenged, had thrown the ball as hard as he could. That turned out to be onto a neighbor’s roof, and, as the one who threw the ball, it was up to him to get it back. He went up to the door and rang the bell nervously. Expecting a surly senior citizen, the door opened, and he found himself staring into the deep brown eyes of a beautiful woman. Later, upon reflection, he would guess that she was in her late twenties, but at that moment, such cognitive thought escaped him. Right then and there, he was nearly stricken mute. Eventually, he was able to mumble enough to explain his errand, and she went back and threw it over the fence into the front yard. Then, months later, when Matt told him about the peeking hole, he knew that he had to see for himself.

Her motion roused him from his daydream. She turned over again and reached for the sunscreen.

Lauren was as aroused as she had ever been. It was so deliciously naughty to tease this poor horny teenager. She could imagine him over there, on the other side of the fence, staring at her with wide eyes. She wondered if he was hard from looking at her, and the thought made her thighs involuntarily squeeze together. Turning her head slightly, she was able to look over at the fence through her sunglasses. Sure enough, there was a knothole about the size of a quarter about three feet above the ground. She lifted the sunscreen bottle and squeezed some out into her hand. In her mind, she could see him going home after watching her, going straight to his room, stiff as a board. He would lock the door, pull his swim trunks down to his ankles, and start rubbing his stiff young prick, thinking about her. In just a few minutes, he would come everywhere, thinking about her tits and pussy and mouth.

Coming back to reality, she slowly rubbed the creamy white sunscreen over her legs. Slowly, making a show of it, she massaged it onto the tops of her breasts, imagining that it was actually his come, delivered after giving him his first blowjob and making him beg for release. She wondered how his young cream would taste. Just to give him something to remember, she gave her nipples a quick tweak through the bikini top, and they immediately rose to attention under the fabric. Laying down on her back, she began a new fantasy of seduction…

Tim was having trouble seeing straight. He was trying to be quiet, but the sight before his eyes had him nearly panting. He followed her every movement as she lazily rubbed sunscreen onto that beautiful body, even her tits! He knew that he was probably imagining things, but he could swear that she gave her nipples a quick pinch before laying back down. Pinch or no, those nipples were standing straight up now. If he even touched his dick at this point, he was going to mess his shorts. The tangible hotness of this woman, and the excitement of secretly spying on her was giving him an erection of incredible proportions. He watched with rapt attention as her breasts rose and fell with every breath. It didn’t occur to him that her breathing was faster than that of a relaxed person. He also liked how she occasionally squeezed her legs together, although he didn’t know what that meant, either.

Lauren was torn between continuing to torment the horny boy and going inside and giving herself a good working over with her favorite vibrator. She was so horny that it was all she could do not to reach into her bikini bottoms and Jill off right there. But how often did she have the chance to tease a tasty, inexperienced boy like this? It was intoxicating.

Deciding to up the ante, Lauren reached behind her head and untied the string holding her bikini top up. With deliberate slowness, she pulled the strings down, peeling the patches of fabric from her breasts. An audible gasp came from behind the fence, and a rush of heat hit her pussy. He had to be glued to the peephole. In her mind, she was looking down at the situation from above the fence, seeing her erotic display and his furtive peeping.

What if I did?, she thought. What if I took him into my house and fucked his young brains out? When the mind is overcome by alcohol, or drugs, or in this case, hormones, rationalizations for anything rapidly spring to mind. Nobody would know, and I’ve always wanted to do something like that.

Seriously considering the possibility excited her even more, but silent doubts kept her from acting.

Then she heard it. A rhythmic squishing sound from the other side of the fence, almost drowned out by the music from her CD player. He was actually playing with himself while watching her. This was the final straw for her horny subconscious. Higher reasoning went silent. She pulled up and retied the bikini top, and got shakily to her feet. Looking down at her towel, she could see the wet spot where her juices had soaked through her bikini and pooled on the towel.

Turning quickly, she walked toward the peephole. Frantically, Tim tried to pull his shorts up over his impossibly hard cock, but to no avail. Scrambling back from the fence, he stood up and turned his back to the subject of his lust. His adrenaline was rushing, and his instinct was to sprint for his bike and get out of there. Oh god, he thought, this can’t be happening. I am going to be in so much trouble…his eyes closed as he prepared for the worst. She would call him a pervert, then contact his parents, and maybe even the police for good measure. In those few seconds, he steeled himself to face the music.

Lauren, dripping with lust, called over the fence. He turned around, still stiff in his shorts, but looking like he was on the verge of tears. Well, she knew how to fix that. She told him to go around to her front door… because there was something she needed his help with. He wandered off toward the front gate with a profoundly confused look on his face. On the way, he pulled his shirt down over his erection, trying to hide it as best he could.

She was there to meet him at the front door, still dressed in the loosely tied bikini. Unable to meet her gaze, he shuffled inside when invited. As soon as the door closed, she wasted little time.

“What’s your name?” She asked.

“Tim,” he answered quietly.

Stepping well into his personal space, she said, “Well, Tim, we have quite a problem here. You could get in real trouble for peeking at people like that. Fortunately for you, I’ll let you make it up to me.”

He met her gaze for the first time, and was immediately helpless in the sexual power of her eyes.

“I need you to scratch an itch for me…with this.” She suddenly reached forward and grasped the hard cock under his shorts. “Is that okay?”

Too shocked and aroused to respond, he nodded jerkily, eyes wide with disbelief, lust, and excitement.

“Good. Then take those shorts off. The shirt, too.”

In ten seconds, he was standing in her living room naked. She stepped back and looked him up and down. Not bad, around fifteen, a yummy youthful muscle tone, and adorably innocent blue eyes. Perfect. And then there was his cock, sticking out in front of him as he tried, unsuccessfully, to hide it behind his hands. Returning to her position right in front of him, she pulled his hands to his sides for a better look.

And it looked delicious. Her mind was filled with ways she could play with that cock, but first things first. She had to see what that cock tasted like. Sinking to her knees, she took him into her mouth in a quick gulp, still holding his hands at his sides. He gasped at the feeling of her mouth around his dick- he’d never felt anything like it. After only a minute, he could feel himself approaching climax. Practically mute to this point, he tried to warn her about what was about to happen, but couldn’t get a warning out before he started coming into that warm, wet, amazing mouth.

As soon as she knew what was about to happen, she reached for his ass, pulling him into the back of her throat. He shot what felt like a gallon of come, and almost collapsed afterward. The desperate noises he made were so hot, it was clear that she’d given him the first blowjob of his life. He leaned against the wall, panting, momentarily spent.

Lauren wasn’t having any of that. “Now”, she said, “it’s time for you to return the favor.” She led him by the hand to her couch, where she finally removed her bikini. His eyes followed her every move, lingering on her breasts. Putting her hands on his shoulders, she pushed him down to a kneeling position in front of her couch, and then sat down before him. Looking him in the eye, she asked, “Have you ever eaten a girl?”

He shook his head. His girlfriend hardly let him even touch her down there, let alone want it kissed. Now, right in front of his eyes, was a pussy more beautiful and sexy than any he had seen in his dad’s magazines. It was glistening and full.

She pointed to a spot at the top of her pussy. “This is my clit. This is where you lick.” Then she pointed lower, to the hole itself. “This is my pussy. This is where you put your finger when I tell you. Okay?”

He nodded and leaned forward. Being eager and inexperienced, he tongue-kissed her clit the way he kissed his girlfriend’s mouth- big, clumsy tongue that seemed to be everywhere but where she wanted it. She reached down and grabbed him by the back of the hair. Pulling away, he looked up at her.

“Easy cowboy. Slow and gentle. Pretend you’re polishing a delicate little egg, and you don’t want it to break. Now… back to it.” She pulled his face back into her crotch, and he did much better this time, using a slow, rhythmic stroke that hit her clit just right. Looking down at his young face buried between her legs, she felt that almost-coming fire in her system. Now to see if the boy could follow instructions.

“Now… a finger…. In my pussy.” He hesitantly put a finger in her pussy, and, not knowing what to do with it after that, left it sitting limply inside of her. As close as she was, she wanted her come to be really, really good, so she gave more instruction.

Catching his eye, she showed him a finger-waggling motion and said two breathless words: “Do this.”

Following her directions, he immediately, he started fingering her G-spot. That’s all it took, and she went over the edge into orgasm. She had time to mutter, “don’t stop until I say…”, and then dissolved into a fit of grunts, moans and screams as her hands pulled his face harder into her pussy.

When she started to come down from the orgasmic high, she told him to stop and let him out of the death grip that she’d had on him with her hands and legs. He wiped his face of her juices, which coated him from chin to eyebrows, and smiled. She pulled him up into a tight embrace, kissed him, and proceeded to lick his face clean.

The combination of the tactile contact of her tongue and the fact that she was licking her juices (her juices!!!) made his young cock spring back to life. It thumped against her thigh as she finished cleaning him up.

“What’s this?”, she asked, reaching down to grab hold of his eager tool. He blushed and looked away.

“Well, I know just where to put it. Come with me...” She took his hand and led him upstairs.

Once in her bedroom, she pushed him back onto her bed. He stared up at her with wide, hungry eyes as his hard cock waved in the air. She leaned down to give him a few teasing licks, and then moved up to straddle him. He wiggled his hips and thrust around, but she kept his cock pressed between them.

“Ah Ah…not yet,” she whispered. She teased him mercilessly, letting the head of his cock brush past the entrance to her dripping pussy, but not letting him inside. His breathing became more rapid and his eyes closed as he desperately tried to push his throbbing, virgin rod into her. She relished the noises when he started to moan and whimper, rubbing his cock against her clit.

Finally, she reached down and positioned his young prick to enter her soaked box. Ever so slowly, she impaled herself on him, watching the his face turn from agony to ecstasy. When she settled on his crotch, he looked like he might pass out from the pleasure. She started to slowly move up and down on his cock, and his eyes flew open, watching her. His hands went to her swinging breasts and began to toy with her nipples.

Lauren increased the pace of her hips until she was bouncing his body off the bedsprings, using him as her personal fuck toy. Bracing herself with a hand on his chest, she reached between her legs to finger her clit. Tim was mesmerized by the sight of her bouncing up and down on his cock, and couldn’t believe the incredible pleasure that she was giving him. He moved his hands to her hips and held on as he continued to enjoy the ride of his life.

As he watched her tits bounce with each down thrust, he felt his balls get tingly again, and this time was able to get out a warning, “I’m gonna come…” before being overtaken by an even harder orgasm than before, bucking against her like an animal and screaming to the heavens.

The sight of this delicious teenage boy under her, back arched, firing his load into her pussy as she took his virginity was all it took for Lauren to come hard herself, her hand flying on her clit. She bucked back against him just as hard, her yell joining his as they lost themselves in a wash of pure pleasure.

She collapsed on top of him, and became aware of several yummy sensations. His half-hard, throbbing cock still jammed up her pussy… their combined juices dripping down her thighs… his panting and moaning under her… the taste of his sweat on her lips… the trembling in his legs from the good workout that she’d given him. Moving up to his face, she kissed him softly.

“Pretty good for a beginner,” she said, and got up from the bed.

They toweled themselves off, and she led him down to his clothes in the living room. He got dressed, and she put on a short, silky robe. Lauren walked him to the door, kissed him again, and said, “I think your technique still needs a little work. Same time tomorrow?”

THE END

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5 Comments
KDLitKDLit8 months ago

Truly a delightful fantasy of mine. Thank you for writing it down.

petitesampetitesamalmost 8 years ago

Very nice, I totally 'Jilled-off' to that one! x

AnonymousAnonymousalmost 20 years ago
More!

Need another about when his friend returns... ;-))

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