His Own Personal Exhibitionist Pt. 01

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Shy teen boy watches older lady neighbour.
3.8k words
4.56
27k
51
1

Part 1 of the 3 part series

Updated 06/11/2023
Created 07/01/2022
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Todd had always been a quiet lad, somewhat shy even, especially around girls. He much preferred his own company to hanging around the streets, any friends he had were people who just happened to talk to him at college. Away from college, he had no time for them. Losing his mother when he was only ten years old hadn't helped. His dad was great with him but recently had been out of the house a fair bit.

Almost nineteen years old now, he had actually managed to lose his virginity somehow. A girl from college, Jane, the female version of himself in that she kept herself to herself, and was one of the few girls that Todd could manage to hold a conversation with. He wasn't exactly sure how the conversation turned to it, but they'd agreed to have sex 'to get it over with' so that they could both legitimately say they weren't virgins anymore when teased. It was more fumbling than finesse, neither knowing what to do for the best, the girl crying after they'd finished. Luckily it was tears of relief and joy that she'd done it.

Todd found himself masturbating a lot more after that. He'd always masturbated quite a lot anyway, but now he had mental images to fall back on. Her blonde hair, her small but firm breasts, and her light blonde pubic hair. they still spoke to each other, but never mentioned that again.

Three weeks after that came the time that Todd thought he'd fallen in love. His house was halfway down a hill, on a bend, and walking down the hill towards his house he saw one of his close neighbours. She lived on the other side of the road about three houses up from his own. Todd didn't know her name, but had waved back and smiled if she ever saw him. This time was different.

The weather had been extremely hot for the last week or so, and she was out washing her car on the front-drive. Her blonde hair was fastened back into a loose ponytail, swishing about with the movements of her body. What also swished about with her breasts, hanging down under her, encased in just a white vest top. Although having fleeting glances so as not to be caught staring, Todd couldn't see any bra straps. She turned away a little to clean the hood, her shorts tight and pulled into her buttocks like her arse was eating them, perfectly sculpted around her frame, like they were sprayed on.

He realised that he hadn't seen her husband for a while, he always used to clean the car. Just then she turned and shouted Hi to him, waving her hand that made her heavy breasts jiggle about, her nipples sticking out where wet patches had formed when soapy water had splashed over her. Todd waved back and scurried quickly home, trying to hide his erection bursting from his trousers.

Getting in he shouted out for his dad, even though he knew he'd be at work. As quick as his erection would let him he rushed to his bedroom window, staring out up the street. She was still there, good. Todd quickly dropped his trousers and boxer shorts and tugged at his cock. He stared at her arse, imagining losing his virginity while fucking her from behind. He watched her jiggling breasts, and then she squatted down to clean lower down, her arse pointing straight at him. He quickly looked around for a tissue and grabbed one just in time as his cock erupted. Looking back up he saw she'd stood and turned around, and was looking towards his bedroom window smiling.

That night Todd got lucky again. He'd got into a routine of leaving his lights switched off. He knew reading his various screens using just the light from them wasn't ideal for his eyesight, but however much he loved his dad if he didn't see lights in his room he assumed he was asleep. Not being pestered suited Todd. He'd been scrolling on his phone when he thought he heard a noise outside. Curiosity made him look but he didn't see anything. What he did was notice that the blonde lady was moving around her bedroom in her underwear. Her curtains were still wide open and it was dark enough that she'd switched on her light.

With the angle of the houses up the hill her bedroom was higher than his, something he regretted a little now. While he could see her heavy breasts almost spilling out of her bra, he couldn't see her from the waist down. He noticed her go to the window and look up and down the street, then continue walking around her room. That was going to have to do Todd thought, as he released his cock from his shorts. He watched her walk around a bit more, getting clothes out of her wardrobe, and then he got lucky as she removed her bra. Her newly freed breasts were so much bigger than Janes were. Thinking this was going to be as good as it got he started stroking harder.

He watched as she moved around to the far side of her room, just far enough that he could now see she was only wearing knickers on the bottom half. She bent forward, keeping her legs straight, and slid the knickers down her legs. Her round arse stared at him, nearly tipping him over the edge, but he soon did as she walked out of her bedroom onto her landing, now completely naked for his viewing pleasure. A towel in her hand, she stopped at her bathroom door and stared back towards the bedroom window, directly towards Todd. Todd jumped as his orgasm came at that exact same moment.

Had she seen him? Had she caught him watching? He thought so, but over the next few weeks her appearing naked while he watched became a regular occurrence. He still hadn't seen her husband, and she seemed to be spending more time with fewer clothes on. Although the bedroom window was higher, Todd found that the kitchen window at her house was much better. At the front of her house underneath her bedroom, a large hedge at the front meant she couldn't be seen from the pathway outside her house unless you were by the driveway. The driveway allowed Todd a perfect view of her kitchen, and the night she walked around in there had been the best yet.

Like before, she'd turned on the main light but not shut the blinds. She not only cooked fully naked, with Todd watching on, but she also ate her meal naked and then bent over the kitchen table probably more than she needed to while cleaning it off afterwards. She then sat back on a chair and Todd noticed her head bobbing about and her eyes closed until she opened them suddenly and looked towards Todd's window. She started to lick something off her fingers and then walked away. Todd watched her arse swish out of sight, then a few seconds later her bedroom light came on and she stood in the doorway, looking towards the window while fingering herself.

Todd had never seen a woman doing this and he tried to match her pace but failed. He shot his load into a pre-emptive tissue, still staring at the blonde lady. He watched as her legs started to shake, then her upper body, she opened her mouth wide and slumped to the floor. About a minute later she got up and walked across to her bathroom. When she returned, Todd had closed his curtains.

Todd awoke the following morning with a raging erection, and the inside of his boxer shorts a sticky mess. He knew he'd fallen asleep playing the action back again and again in his head, and then dreaming about it too. Showering and changing, he left the house to go to college. Walking out of his driveway something made him cross over. Walking past her house he noticed a small box on the doorstep, a delivery. Her car had gone, so he knew the parcel would stay there all day. Quickly he walked over and picked up the box, putting it into his backpack. Now he could put a name to the person, a fresh perspective to watching her. Not only that, but he'd also be able to see her up closer when he took the parcel to her.

Getting back from college that afternoon he'd forgotten about the parcel until he started to empty his backpack. His father not being in, he quickly checked over the road. Her car wasn't back yet. He looked at the time, she normally got back in a round twenty minutes. Not that he'd been checking on her, of course. He looked at the box, wondering what was inside. It was a rectangular shape, plain brown cardboard with just an address sticker on it. "Kayleigh Morris' it read. Kayleigh. He liked that name. Saying it to himself bought images into his head of her. He shook the box, no sound.

Curiosity was getting the better of him. She lived at 43, he lived at 34. He could easily open it and then explain he'd not read the name or address as he'd been expecting a delivery too. He quickly picked up some scissors and ran them down the tape sealing the box. Putting his hand in and pulling out the packaging he felt something firm, then dropped the box onto his bed. Surely it wasn't? It couldn't be? But then not seeing her husband about now made a little more sense.

Having fallen out of the box now, a seven-inch dildo stared up at Todd. It was like his own, lifelike in look and colour, even with similar veins along its shaft. It was flat at the bottom, Todd realising it was a suction base. Picking it up he saw something else had fallen out of the box too. He picked it up to see a white lace see-through nightie, and some white stockings fell back onto the bed. He held up the nightie and looked in his mirror. He hoped he could see Kayleigh in these, the sooner the better he thought as he felt his erection growing again.

First though, he needed to take the box back. He would need to speak to her, to explain the reasoning behind him having the box, and then why it was opened. He wasn't looking forward to this but knew he had to. He heard a car outside and looked out to see Kayleigh getting out. No time like the present he thought.

He walked over to her house, box in hand, getting more apprehensive the closer he got. Twice he paused, wondering whether to go back home. He knocked on the door, seeing Kayleigh walking towards him through the glass. She opened the door and smiled at him.

"Hi, you live across the street right?" she asked.

"Yeah, I'm Todd," he said, sheepishly pointing back towards his own house, "I'm sorry to bother you but this parcel got delivered to our house by mistake," he continued.

"Oh, okay, thank you for bringing it over then," Kayleigh smiled, her face changing when she saw the package was opened.

"Erm, yeah. I've been expecting something too, so I didn't know it was for you," he spluttered.

Kayleigh had looked inside the box by now and had seen its contents. She looked up at Todd.

"So, have you looked at what was inside it?" she asked. Todd blushed.

"I'm really sorry, I didn't mean to, I just tipped everything out onto my bed.

Kayleigh picked out the nightie, putting the box down on the floor. She held it in front of her, even with her top on her breasts were heaving against the lace material.

"So, do you like it then?" she asked, a little giggle as she finished asking. Todd blushed again.

"It looks very nice, I'm sure it will fit nicely too," Todd answered.

"And as for the other thing, that needs to be our secret. I've been a little lonely since my husband left," Kayleigh said, her voice almost purring.

"Anyway, thank you again for bringing it over, I might thank you again later, although it looks like you can't wait for it to get dark," Kayleigh laughed, pointing at Todd's crotch.

Todd looked down at his erection trying to burst out of his shorts. Kayleigh still holding the nightie up over her heavy breasts hadn't helped. He muttered an apology, covered his erection with his hands, and started to move off towards his own house.

"Oh, by the way, you can leave the lights off and leave your curtains open as much as you like, but if your landing light is on, or there's a street light shining by your house, I can see you too," Kayleigh laughed, "Maybe you could leave your light on too perhaps?" she continued.

Todd got over to his house, his head playing their conversation over and over. She'd left him in no doubt that she knew he'd been watching her. In that case, it meant she'd been deliberately walking around naked knowing he was watching, doing it specifically for him. Knowing his dad would arrive home soon, he went into the shower where he could masturbate and not be disturbed.

Todd couldn't wait for it to get dark that evening, but when it did he was a little upset. There were no lights on in Kayleigh's house, and her car was gone. He resigned himself to playing computer games to pass the time away, and eventually, he heard a car. Looking out of the window, Kayleigh was home. She got out of her car, turned and looked towards Todd's window, and smiled. Todd saw lights come on through the house, in the kitchen, then the landing, then her bedroom light. She walked into the room, pulling the t-shirt she had been wearing up over her shoulders.

Although he'd seen them a few times now, the sight of Kayleigh's heaving bosom appearing from the confines of her clothes surged through his young body. He felt the blood rush to his groin, watching as she slid down her jeans. The black underwear she had on contrasted nicely against her skin and hair colour. Standing right in front of the window, she checked up and down the street before undoing and discarding her bra. Her hands went to her nipples, tweaking and pulling at them, contented smiles breaking out in between the gasps of pleasure. She paused to point over at Todd's house, then rubbed her hands across the top of her body. Reading her mind, Todd removed his t-shirt.

Kayleigh continued playing with her breasts for a while then turned towards the bed. She momentarily looked towards him, then climbed so she was standing on her bed. Keeping her back to him she slid her knickers down over her arse, letting them slide to her ankles. Reaching around she slid her hand between her arse cheeks, rubbing slowly and gently. She turned her head to look at him, motioning for him to get up too.

Todd stood on his bed, his shorts tenting. Kayleigh motioned him to push them down and taking a deep breath he did so. Although she was in her own house, Kayleigh was only the third girl who'd seen his erect cock. Getting down off her bed, Kayleigh opened her bedside table and took something out. Standing by the window Todd saw the dildo in her hand. She stroked it, simulating wanking it, nodding towards Todd. Realising what she wanted he started to stroke his cock for her. Kayleigh watched for a while, then put the dildo to her mouth and slowly inserted it.

It was all Todd could do not to blow his load there and then. He'd never had a blowjob yet, and seeing this object of his desires doing so even on a fake cock was breathtaking. She matched her pace with his strokes, one hand holding the cock and one tweaking at her nipples. After a while she held her hand up, telling him to stop. Putting the dildo down she put on the white lacy nightie and her white hold-up stockings. She stood by the window again, her large erect nipples poking through the see-through fabric. Putting the dildo back into her mouth, she slurped on it hungrily.

Todd watched on, his strokes getting faster, his grip on his cock tighter until Kayleigh paused and got onto the bed on all fours, her arse facing towards Todd. Looking back over her shoulder she put a thumb up. Todd assumed she was checking he could still see and signalled yes. Reaching a hand behind herself, her back arched as she pushed the dildo into herself. Kayleigh kept looking back over her shoulder until she saw Todd cry out and shoot his load all over his floor. she paused her dildoing, and then Todd watched as she walked out of her bedroom and across the landing.

Damn! He was hoping for a longer show than that, he was angry at himself for not lasting longer, but imagining himself being there instead of the dildo had pushed him over the edge. Suddenly his mood changed as Kayleigh appeared in her kitchen. The lights were brighter in here so Todd had a better view, he could see the contrast in fabric on her nightie, the colour of her nipples showing through the cups, the feint wisp of blonde pubic hair between her legs.

He watched as she walked around the large glass table, seated on heavy-set legs all around it. Getting close to the window she moved a chair, and then stuck the dildo onto the glass. Clambering up onto the table, Kayleigh lay on her back with her legs towards Todd. Hitching them in the air, her hand slid along her pussy a few times and then stroked the dildo, making sure it was covered in her juices. She signalled for Todd to stand up again, smiling seeing his fresh erection as he climbed onto his bed. She squatted above the dildo, teasing her pussy with the very end of it, watching Todd as he started to stroke again.

Kayleigh pushed her hips down and sank onto the dildo, a little at a time, teasing more and more into herself, staring intently at Todd as she did so. She had been enjoying teasing him over the last few weeks, showing herself for him and enjoying him thinking she couldn't see him watching her. It had been a long few weeks since she found out her husband was cheating on her and had kicked him out. While she had found a weird enjoyment out of exhibiting herself to her young neighbour, bringing joy to herself knowing that someone was masturbating over seeing her body, she now found herself longing that the dildo now fully impaled in her wet pussy was Todd lying under her.

Todd was enjoying the view himself. Despite being where they were, he could see how Kayleigh's pussy clung to the dildo as she rode up and down it. Despite being sexually inexperienced he had a good understanding of the basics, but now he stroked absentmindedly as he took in as much as he could. The soft curve of her thighs, the slight bulge where her stocking tops pushed into her flesh, the curve at the bottom of her buttocks as the dildo withdrew, the way her large breasts swung about as she rode harder and faster. Like she'd read his mind, she pulled the lace cups down under her breasts, pushing them upwards more, her cleavage accentuated even more than usual.

Kayleigh concentrated on his cock, trying to match his strokes. she could feel her stomach churning over, her orgasm bubbling up inside herself, and fought the urge to rub at her clit. She tried to prolong as much as possible, to keep this feeling going, but then changed her mind. If he came again first, would he stop watching her momentarily? She wanted to see him cum, to watch him shoot his load knowing it was through watching her, but she had another idea.

Kayleigh leaned back a little more onto one hand, tilting herself to ride the dildo at an angle as she bent backwards more. Now she knew Todd would still be able to watch the dildo sliding in and out of her, and had a hand free for the second part of her plan. Sliding a finger over her clit, she rubbed herself eagerly. She closed her eyes with pleasure but forced them open to see him. Her legs started to quiver as she got closer, her stomach tensing, her body shaking, until she came hard and squirted across the glass surface. She didn't let up, still riding and rubbing through the orgasm, gushing across the table and her stocking-clad feet. Pulling herself off the dildo and lying on the table, her plan worked.

Todd watched as Kayleigh started to shake, her legs trembling. He had a vague idea that she was going to orgasm, but wasn't expecting the several gushes of liquid to flow from her. His strokes got faster, leaning in closer to the window to try to get a better view, until he came, spurt after spurt crashing against his window pane. Still standing in the window, he opened his eyes to his sticky mess and Kayleigh, now standing with her dildo in her hand, smiled and blow a kiss to him. She turned and slowly walked away, giving Todd one last chance to view her round arse, before she turned off the light and left Todd to wipe away his mess.

Todd slept soundly that night, his dreams full of mental images of Kayleigh. He awoke the next morning, a Saturday so no college, to the front door being opened and several voices. He quickly pulled on a t-shirt and went to the top of the stairs. His dad smiled up at him, a redhead about his dad's age smiled up at him.

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