Victoria's Secrets Ch. 02

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Tommy gives Vicky a helping hand, and gets one in return.
12.5k words
4.72
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Part 2 of the 2 part series

Updated 06/09/2023
Created 02/09/2020
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Satyr81
Satyr81
140 Followers

Lying in his bed, Tommy stared at the pages in front of him. But for all his attempts at reading, the book might as well have been written in Greek. It wasn't that it was a difficult book to read, in fact he had read it a few times before. Tonight his mind just refused to focus; he was a bundle of impatience, nervousness, and guilt.

Brushing his medium length brown hair out of his eyes, he sat up and peeked out his window at the large double window of the neighboring house. It was still dark.

For a little over a month now he had been spying on his neighbor, Mrs. Victoria Madison. She had been their neighbor for years, and Tommy had always found her attractive. From her fit, supple legs to her enormous chest, to her platinum blonde hair; every part of her aroused him. She had been a prominent figure in his masturbatory fantasies for a couple of years now, so when he had noticed her blinds wide open one night as she changed for bed, he couldn't help but watch.

It had been amazing, watching her slowly drop her business clothes to the floor until she was in nothing but a matching set of panties and a bra. That night, and for several after, she had stopped at her underwear and then gone out of sight to finish changing. But for Tommy, it was enough to fuel his imagination as he lay in bed stroking his cock to thoughts of his voluptuous neighbor.

Then one night a week later, she didn't stop at her underwear. Standing beside the window, her work clothes pooled at her feet, Mrs. Madison reached back and unclasped her bra, dropping it to the floor. For the first time Tommy saw her impressive breasts, so large and round. And topping them both were large round nipples; hard, pink little nubs at their center. As he stroked himself, Mrs. Madison just stood by the window, turning this way and that, as if checking herself out in a mirror.

From then on, Mrs. Madison's displays seemed to escalate every few days. She began taking longer and longer to check herself out in the mirror. And her underwear seemed to get sexier, from plain bikini bottoms to thongs and lacy boy shorts. Some nights she even left her heels on while checking herself out. Those were Tommy's favorite nights, at least at first. Then she started touching her breasts, kneading them in her small hands, pulling on her nipples, teasing the little nubs with her fingertips - after that Tommy didn't really notice what she wore on her feet. All he knew was that watching this amazing, mature, sexy woman as he stroked his hard cock was the highlight of his days.

Then, on the previous Monday things had gone even further. She had been wearing nothing but a tiny black g-string as she looked herself over in the mirror. Her breasts heaved as she breathed deeply in response to the way her hands toyed with her tits. As she stood there, her left hand crept down her body to the tiny black triangle covering her sex. Tommy had never seen anything like it, but he still knew what he was watching as her fingers slipped beneath the fabric, pushing it out as her finger played with herself. Her hand began to move quickly, the wide-mouthed expression of pleasure on her face was unmistakable even from the distance between their houses.

As Tommy watched Mrs. Madison pleasure herself, he couldn't hold back the pressure building from his own self-love. Grabbing the towel he kept nearby, he erupted, spewing rope after rope of sticky cum into the towel as he groaned quietly. When his mind refocused on the scene across the small yard separating the two houses, his busty neighbor was still at it. Her mouth moving as if yelling something, her hand on her tits squeezing one of her large breasts tightly as the hand between her legs moved at a wild pace. Suddenly her body froze, her eyes shutting and expression strained. Weakly she dropped to her knees for a moment before standing and quickly lowering the blinds.

She had never lowered the blinds like that before, and suddenly all the pangs of guilt Tommy had been feeling over the weeks returned in a rush. What if she suspected? What if she saw him? What if she told his parents?

But now it was Friday and he hadn't seen her since that night, her blinds had remained closed. She didn't always forget to leave the blinds open, so at first he wasn't too concerned. But for most of a week? He was certain he had been caught, somehow, even though he always kept his own lights off. Still, she hadn't told his parents, so that was probably a good sign.

But was it over? Would ever get to see her again? What right did he have to be upset if he didn't? He was invading her privacy, it was a horrible thing he was doing. But it felt so good; while he was disgusted with his behavior, he was also hoping, praying, that her bedroom light would turn on so he could see her one more time.

With these thoughts flooding his brain, there was just no way to focus on the book in his hands. Giving up, he tossed it to the ground and tried to accept the fact that it was over, and he should be grateful for what he had gotten. He still had his memories, he thought as he slipped a hand beneath the elastic band of his boxers. As he ran his fingers over his swelling cock, reaching down further to run circles over his balls, the light across the yard came on, Mrs. Madison's room easily visible.

A second later, she appeared by the window, sending Tommy's heart into overdrive. He was having trouble breathing as he watched her begin to unbutton the purple silk blouse she had worn to work that day. Her hands slowly moving from one button to another, gliding over the fabric concealing her round breasts.

Tommy was so surprised that he nearly forgot to turn off his own light. Turning around he double checked to make sure his door was locked; and then he turned off the lamp by his bed, throwing his room into darkness. As his light winked out, he thought he caught her glancing towards his window and he was filled with panic.

The anxiety of being caught quickly vanished as Mrs. Madison returned to unbuttoning her blouse. Taking deep, slow breaths, Tommy slipped out of his boxers, his cock growing firm just from the anticipation.

Please touch yourself again, Mrs. Madison. Maybe remove your panties this time? God, I just want to see her pussy.

With the purple blouse undone, she dropped it from her arms, displaying her large chest. The black, low cut, lace bra holding her breasts left a vast amount of tit flesh exposed to his gaze. And as she reached back to unclasp her bra, her breasts jutted out further, causing Tommy to tighten his grip on his hardening manhood. Tightly fisting his cock, he slowly worked his hand up and down, his foreskin rubbing back and forth over the ridge of his cockhead, until Mrs. Madison's bra finally fell free.

Her magnificent, full breasts now fully exposed, Tommy released a breath he hadn't realized he was holding, and he relaxed his grip on his cock. Moving his hand up and down more freely, he ran it over the throbbing, silken head, a bead of precum catching on his palm as a small wave of pleasure washed through him. However, unlike previous nights where Mrs. Madison had played with her tits, tonight she went straight to her black skirt, letting it drop to the ground.

Black lace boy shorts held her round ass, which Tommy imagined gripping in his hands as his mouth nibbled at her large nipples. His hand stroked faster when he saw her slip her thumbs in the band of them. Was tonight the night? Would he finally see her pussy?

In his excitement his breathing became shallow and quick, his cock growing harder. Turning away from the window, Mrs. Madison bent over at the waist, her legs together, ass in the air as she lowered the boy shorts to the floor.

Tommy couldn't be sure at this distance, but he could have sworn he saw her pussy lips peeking out from between her legs as she bent over. But real or imagined, he was sure that ass was real. He let out a quiet moan as he tried to calm himself. His cock and balls desperately wanted to cum, but he desperately wanted to see what more was in store for him that night.

His brain won out and for the moment he managed to relax slightly. But it was short lived, his pace quickening again as the busty blonde laid across her bed, legs spread and pointed towards the windows. There it was, what he had been waiting for. Stroking hard and fast, Tommy's gaze was locked on the slit between Mrs. Madison's legs. Just above it sat a neatly trimmed patch of dark hair. Hair that was soon hidden by her hand as she reached down, her small, feminine fingers slipping up and down her slit.

Tommy wanted to groan out loud, but held back from fear. The very real fear that his parents might hear him, but also the irrational fear that if he made any noise his neighbor would hear him and stop. It was crazy, but with his brain fried by lust and his hand stroking his large angry cock closer and closer to an orgasm, there was no room in his mind for being rational.

Mrs. Madison's hips bucked up off the bed as a pair of her fingers pushed deep inside her pussy. And as Tommy watched the carnal display of his mature neighbor fucking her own fingers, all he could think of was what it would feel like if it was his own cock thrusting into her slit. Imagining himself there on the bed with her, his hair hanging down as he looked into her blue eyes; her huge tits pressing up against him as he rocked against her; his thick, hard cock milked tightly by her wet pussy.

"Oh... shiiit..." he moaned, as he doubled over as if in pain; and it nearly did border on pain, that complete bliss as his cock began to spew a load of cum. Semen shot from the tip, some dripping onto his hand as it continued stroking through his powerful orgasm. But most of it sprayed across the carpet and wall beneath the window sill.

Blinking, Tommy's mind finally cleared enough for him to realize what had happened.

"Oh fuck!" he cursed.

Does cum leave stains on painted walls? It's painted white, so it should be ok, right?

Unsure, but terrified of the possibilities, he grabbed for the towel under his bed. Making quick work of his hand and cock, he tried to get up the cum from the carpet and wall. Carpet cleaner, he realized, was what he needed. He'd have to sneak downstairs and get it after his parents were asleep.

Sitting back on the floor, he rested his back on the side of his bed, trying to calm his nerves. This is what happens, he scolded himself. This is what happens when you take things too far. He shouldn't have been watching her in the first place, especially something so private. He had violated her privacy. He deserved to get caught. And he swore that if he got away with it, he would never, ever do it again.

Eventually, however, his curiosity overwhelmed his guilt and he peeked up through the window once more. Mrs. Madison still lay on her bed, her breasts heaving deeply, her hand laying across her pussy, completely still. Then she stirred; rising from the bed, she moved over to the window. Her beautiful nakedness was on complete display as she looked directly at him through the window.

"Oh... fuck..." Tommy swore as he ducked down. His room was completely dark, so she couldn't see in, right? Surely she hadn't seen him.

His heart pounding in his chest, Tommy lay there, imagining scenarios in which she confronted him, or told his parents, or called the police, or notified the admissions board of the university he was attending in the Fall. Every possibility crazier than the last. But none as wild as the scenario that would play out that weekend.

*****

The next morning, Tommy sat at the circular breakfast table in the family kitchen. His dad had taken his sister Kara out to a gymnastics meet earlier, so he was sitting alone, nursing a headache from poor sleep and chewing on cold pizza when his mom entered the kitchen.

Pouring herself a cup of coffee, his plump mom sat down across from him in her big puffy blue robe and stirred sugar into her mug.

"You're up early, mister."

"Couldn't sleep," he mumbled around a mouthful of cold pizza.

"Worried about starting college?" she asked, concern clear in her voice.

"Mmm hmm," he replied, refusing to meet her face.

"Well you don't need to be. You'll do great. Your dad and I are so proud of you," she said, the smile on her face evident in her voice, even though Tommy couldn't look at her. And while her words had been meant to encourage him, they only made the pangs of guilt dig deeper.

His head shot up as the phone rang. Hopping up, his mom grabbed the cordless phone and answered it as she sat back down.

"Oh, hello Victoria. How are you?"

Tommy's breath caught as he realized his mom was talking to Mrs. Madison. Was this it? The thing that had kept him up all night - was it coming true?

"I see..." his mom said, her voice emotionless as she looked across the table at him.

Tommy hoped that his mom couldn't make out the small sweat that had broken out on his forehead and hands. Not that it would matter once Mrs. Madison was done telling her how he had been spying on her.

"You know what," his mom said suddenly, "maybe it would be best if you talked to Thomas directly. He's right here next to me."

Handing him the phone, his mother mouthed, "Be polite," at him as he took the cordless phone in his shaking, sweaty hand.

"Uh, hello?" he croaked out nervously.

"Hey there Tommy," said the sultry, southern voice on the other end of the line. "I need a little favor and I was hoping you could come over and help me out. It won't take long, and I'll be happy to pay you for your time. I was thinking, sixty bucks?"

"I, umm, I don't really know..." he began, confused by the turn of events. She wasn't calling to rat him out? Maybe she really hadn't seen him after all. But could he stand to be around the woman he had spent the last night wanking off to in his room as he peeked on her own intimate moment?

The decision was made for him, however, when he looked across the table at his mother who was frowning and nodding her head.

"Yeah," he blurted out, "I mean, yes, I don't think I have anything going on today."

"Great!" Mrs. Madison exclaimed, "It won't take long, I promise. Can you come by just after lunch?"

"Sure. I'll see you then," he replied, his voice finally returning to normal.

Hanging up, he felt like a huge weight had been lifted from him. If she wanted to curse him out or tell his parents, surely she wouldn't have sounded so eager and happy, right?

*****

The rest of the morning seemed to fly by as Tommy got himself together, did a little reading, and generally spent the morning doing what most eighteen year-olds do on a Saturday morning - nothing.

After a light lunch, Tommy pulled on his shoes and headed next door. Mrs. Madison's pale blue house seemed to loom over him as he approached it, his throat going dry as he thought back to what he had been doing the night before. He tried to calm his breathing, but it didn't really help; and his joints felt stiff and unresponsive as he reached for the doorbell.

Waiting for an answer he tapped his foot, more from nervousness than impatience. But before long the door flew open, and he couldn't help but be a bit stunned by the sight. Mrs. Madison wore a tight green t-shirt, with a deep v-neck that showed a hint of her deep cleavage. From the way the shirt was pulled tight across her body, Tommy would have sworn it was a size too small. Not only did the shirt not reach the top of her small denim shorts, but the shirt was so tight he could make out her bra straps and her nipples as they pressed against the cotton shirt.

"Come on in, now," she told him, her accent heavy.

Looking up, Tommy worried he had been staring at her breasts and felt his face flush as he looked into her big blue eyes framed by heavy black eyeliner. But if she had noticed, she didn't seem to mind; her wide mouth was drawn up into a smile.

Stepping inside, Tommy gazed around the room. It was a living room, clearly, from the long leather sofa and easy chair facing a medium sized flat screen TV. Mounted along the walls were pictures, most of them included Mrs. Madison when she was younger and a man who seemed a bit older than she was.

"Was this your husband," he asked, pointing at one of the pictures.

Pushing back a strand of platinum blonde hair over her ear, Mrs. Madison walked over beside him.

"Yes, he was. He passed away right after we bought this house, but before we could move in. That was..." her voice trailed off longingly for a moment, "just over five years now."

"I'm sorry," Tommy replied, unsure of how else to respond.

"Oh, I miss him, terribly," she said, "but I've also learned to move on. I dwelled on my loss long enough, so lately I've been trying to make the most of the time I have.

"But enough dawdlin'. You must be wondering why I asked you over."

"Yeah, kind of."

"Well, I just needed some help. I recently ordered a big TV to go down here and wanted that TV moved up to my room so there was space when it's delivered this evening."

Tommy frowned slightly. Sixty dollars to move a TV that she should have no problem lifting?

"You seem a bit confused," she said sweetly, her hand resting lightly on his arm. "But I think you'll see why I need your help if you follow me upstairs."

Still uncertain, Tommy was more than happy to watch her swaying ass in the tight fitting jean shorts as she climbed the steps in front of him. Reaching the upper floor, she led him to a bedroom on the far end of the house. It was a small bedroom with light green walls, a short dresser sat against one wall and a queen bed against the far wall, framed by a pair of bedside tables. On the dresser sat a small, much older TV.

"I need this one down to the garage. The bigger one from my bedroom moved into here, and the one from downstairs into my room."

"Sounds easy enough, sixty bucks still seems a bit high though."

"Oh, don't worry. I heard you're heading off to college soon and I know you'll need the money. Think of it as a graduation gift."

Shrugging, he walked over to the TV to disconnect it from the wall. "Alright then," he said with a grin, "I guess I should get started."

Getting the TV out of the guest room was a pain, the old TV was heavy for its small size, and it was just big enough to be too big to carry comfortably down the stairs. By the time Tommy managed to get it into the garage, his hands were red, his back was sore and he had started to sweat. The TV from Mrs. Madison's bedroom was the worst though. It was smaller than the TV downstairs, but was still an old CRT model with a thick glass front. He'd ended up needing her help just to get it down the hallway from one bedroom to the other. But before he knew it, he was carrying the flat screen from downstairs up to her bedroom.

Backing away from the TV, Mrs. Madison turned it on, clasping her hands in delight when the picture and sound came through clear on the first try. As she checked out the TV, Tommy looked around her room. Sure enough, there was a large standing mirror in the corner next to her window. He could see his own window out of hers, and in the daylight he could see right in. He began to sweat even more, his nerves kicking in.

You can only see in because of the sunlight, at night the room would be too dark to see, he reassured himself. It wasn't very successful.

Turning around, he was stunned to see Mrs. Madison bent over next to the bed, legs straight, ass in the air. Suddenly she straightened, a purse in her hand. Opening it she dug around, her face frowning slightly.

"Well, shoot," she finally said. "I just know I had sixty on me, but now I can only find forty."

"That's more than enough," Tommy replied.

"No, no, I promised you more," she replied, her voice turning soft. "And more is what you're going to get. Now if I can't pay you the money..." Her voice trailed off as she stepped close to him. He was suddenly aware of the fact that she was actually a few inches taller than him. He was short for his age, and while he may have weighed a good bit more than her, her height gave her eyes a predatory gleam.

Satyr81
Satyr81
140 Followers