The Spectator Ch. 01

Story Info
Jack prepares to take Cindy to the pinnacle of corruption.
2.2k words
3.88
14k
7
0

Part 1 of the 3 part series

Updated 10/29/2022
Created 12/11/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Cindy had caught a glimpse of The Spectator on the very first day she moved into her cottage in the archetypal English village of Stoneleigh. Surrounded by its undulated hills and breath taking countryside, Cindy felt like she had finally sound somewhere she could sincerely call home.

She'd been in the shower to blast away the damn dust and cobwebs that had clung to her fair, pale skin as she'd tried to clean the cottage so it could at least pass for being inhabitable. Stepping out of the shower, she'd suddenly realised that she'd forgotten to bring her bath towel. As the December chill whipped against her skin causing her nipples to harden like flesh coloured bullets, she berated herself for being so careless. She had no choice but to quickly leg it across the landing to the bedroom and grab the towel off the bed. As she wrapped it quickly around her tiny frame, she glanced out of the bedroom window and looked at the house that was back to back with her. She watched the blinds that donned the bedroom window briefly flicker before shutting again. Cindy quickly bent down, she really should have put up her bedroom curtains and she made a mental note to make sure it was her next job of the evening, the last thing she needed was to attract the attentions of the village's resident Peeping Tom.

"I don't like the term Peeping Tom, it conjures up in my mind images of a man dressed in seventies flare, a dodgy moustache using binoculars to peer into women's bedrooms. I like to refer to myself as a voyeur, an observer, a spectator. Not a hidden spectator I hasten to add. I like my subjects to be fully aware of my presence. Some people don't like it, some people love it, like anything in life, sometimes you win and sometimes you lose."

Cindy hadn't thought too much about that day when she had seen her neighbours blinds briefly flicker, she'd been far too busy settling into her new abode. One Saturday afternoon as she wrestled putting up a particularly awkward pine shelf in the kitchen, Cindy's cursing was interrupted by the sound of the doorbell. Pushing her blonde hair back into its hair band, she quickly checked her reflection in the hallway mirror, rubbing a splash of paint off her pert nose, Cindy opened the door.

"I thought I would welcome you to the neighbourhood." The guy handed Cindy a card and a box of fresh cream cakes.

"Thanks. That's so kind of you." Cindy suddenly felt overwhelmed and a tad self conscious. She paused and a tiny pink flush of embarrassment crept over her cheeks. "Sorry, I don't know your name.''

"Jack. My name is Jack." He extended his hand. Cindy shoved the card under her arm and took his hand in hers.

"I only moved in a couple of days ago." Cindy explained, not really knowing what she was expected to do right now.

"Well, you've done quite a bit to the place since you moved in, the garden for a start looks miles better and the Christmas tree is really cute. This place went to rack and ruin when old Bill died which was a shame really because he'd always taken great care of it."

Jack flashed Cindy a smile and there was a momentary awkward silence that Cindy felt compelled to break.

"Why don't you come in? I'll make a pot of tea and we can share these cakes if you like."

Jack flashed her a friendly grin. "That would be wonderful, thanks."

"I don't go for a particular type of woman. Being a voyeur I think means that it's not the other person you are attracted to per se, it's the fact you are watching when you shouldn't be and watching people do things they strictly shouldn't be doing. I think it was Cindy's wholesomeness that appealed to me and the glimpse I'd had of her slightly boyish figure that day when she'd moved in had piqued my interest. Close up, she was even more attractive to me than I could have ever really imagined. I think it was the way her freckles were smattered across her cute nose and the slightly crooked smile that made her look incredibly cute. She was smaller than my usual type too in height and in the breast department but she did something to me, I think deep down I was hoping that she was as horny as she looked."

"So have you lived round here long?" Cindy asked as she handed Jack a mug of steaming hot tea.

"I've lived here around ten years. I came here when I was twenty five with my first wife, but sadly we divorced and I've lived on my own ever since. I must be getting old and set in my ways.''

"Don't be silly, thirty five isn't old." Cindy smiled at him and noticed that actually there was something about Jack that made him attractive. He wasn't good looking in the traditional sense. His brown eyes were a little too close together and his hair was shoulder length and in need of a trim but his smile was wide and friendly and it was obvious that he looked after himself. His waist was trim and his shoulders wide, he was clearly no stranger to the gym. If asked the question would she, wouldn't she? The answer would be yes, she definitely would.

"Telling me thirty five isn't old is a bit rich coming from someone who can't possibly be a day over twenty six." Jack sipped his tea and gazed at Cindy intently causing her cheeks to flood with a bright pink blush.

"Actually, I'm thirty." Cindy grabbed the box of cream cakes. She motioned for Jack to follow. "Come on, let's sit in the conservatory"

"So Cindy took me through to the conservatory and we sat and drank our tea and devoured the cream cakes like any quintessential English couple. She told me she had a few jobs that needed doing to complete her move and I offered to help. She was delighted of course and that afternoon a new friendship was sealed. Cindy was easy to be around and just the same as some villages were missing an idiot, Stoneleigh had been devoid of a decent looking woman under the age of sixty for a good many years. I had a feeling that Cindy and I were going to get on well, hopefully very well indeed."

Cindy watched as Jack managed to finally put up her shelving unit. She'd invited him to stay for dinner and as she resumed chopping the garlic she had to admit that she fancied Jack. There was a presence about him that made her feel warm inside.

That evening after they had eaten and the dishes had been washed and put away they both retired to the conservatory and shared a bottle of crisp, bottle of Chardonnay.

"Thanks for helping me today, I really do appreciate it."

Jack took a sip of his wine. "Absolutely my pleasure, what more could a man ask for? A lovely meal, the best prawn linguine I've had in a while by the way and the company of a beautiful woman to wile away the evening with."

Cindy felt herself go warm at Jack's compliment. Pushing her legs beneath her, she brushed down her skirt.

"Flattery will get you every where Jack."

Jack topped up his glass with wine and grinned at her. "I hope so."

"As Cindy pulled her knees beneath her as she made herself comfortable, her skirt had risen and I'd caught just a glimpse of her white lace knickers or was she wearing a thong? Either way, just that tiny glimpse had made my cock stir to a semi hard on that I hoped wasn't going to extend into a full blown affair or that would have been quite embarrassing. You see, for me sometimes a tiny glimpse of something gets my rocks off better than when a woman has her assets on show. I liked an air of mystery and Cindy had provided me with that.

Ever since the first time I'd met her I had been wondering about her small, pert breasts. Were her nipples a soft pink or a dark brown? Did she shave her pussy completely or leave a nice little strip? How did she make herself come and what exactly made her come? That was the question that had been regularly assisting my wanks. I imagined Cindy bringing herself off. Watching women masturbate was just one of the many things that I found horny. If they were aware of me watching them even better, but sometimes I liked to think I'd gone unnoticed."

"That's my bedroom." Jack pointed at the house that was directly back to back with Cindy's. Cindy followed the direction of Jack's finger and realised that his bedroom blinds had been the ones she had seen flicker the day that she had moved in.

"Oh right." Cindy couldn't think of anything else to say, mainly because her mind had suddenly started to race, had Jack seen her naked that day? She didn't know whether to feel embarrassed or excited.

"Yeah, so you better watch what you are doing, you never know when I might be watching you.' Jacks eyes twinkled and as Cindy's eyes widened to saucer size proportions Jack threw back his head and laughed. "I'm teasing you, don't worry, I'm not a pervert."

Cindy leaned forward and moved a stray hair out of Jack's eyes. "What a shame." She murmured before sitting back on the settee.

"When she had said what a shame,'' I felt the familiar stirring in my loins. I didn't know if it was the wine talking although admittedly Cindy had only had two glasses. Either way, all I knew was my gentlemanly nature had drifted away like tumbleweed in a storm. Her comment had put a wax seal on the does she fancy me, doesn't she contract and I did what any other man would do in that situation, I went back home for some more wine."

Cindy couldn't remember the last time she had played Truth or Dare. Then again, after the wine she'd consumed that evening she was lucky she could still remember her own name. She opted for Truth because a Dare might involve actually having to stand up and she didn't know if she was even capable of doing that.

"Have you ever let anyone watch you as you fuck? Either you have invited them to watch or you have sensed someone uninvited watching you?"

Cindy shook her head. "No, I can't say I have, not a bad thought though is it?"

The words were out of her mouth before she could stop them and normally she would have been mortified but the wine had stripped away any of her inhibitions. "I actually think I might like that."

"So not only did she fancy me she liked the idea of being watched which is like all my birthdays, Christmases and orgies arriving all at once. There was just one slight and obvious hiccup; Cindy was pissed out of her head. I hold my hands up, I'd been the one to provide the nectar from the drunken Gods but I hadn't banked on Cindy being fully compos mentis one minute discussing the benefits of pureed garlic as opposed to chopping her own to admitting that she too had voyeuristic tendencies. I wanted to get her a bit squiffy and relaxed enough that I might be able to make a move but I'm not the kind of guy to take advantage of a woman who isn't fully in control. I like a woman to know exactly know what they are doing and like what they are doing, after all, isn't that the biggest turn on of all?"

Jack handed Cindy a cup of black coffee. "Here, drink this it might sober you up a little.''

Cindy's head lolled to one side slightly as she laughed. "I'm not drunk,'' She slurred, knocking the TV remote control off the chair arm onto the floor.

"Yes you are now sit up properly.'' Jack put the coffee cup on the table and gently pulled Cindy's arm so she could sit up straighter. She did as she was bid and looked at Jack, her eyes trying to focus.

"I'm ok, really yam.'' Her lips dropped to one side in an attempt to appear petulant.

"Right, you're not drunk, but you're still drinking this coffee okay?''

"I waited while she drank her coffee and by the time I was leaving, Cindy was curled up on the chair asleep and snoring.

That evening I couldn't sleep. I lay awake thinking of Cindy's revelation that she wouldn't mind someone watching her as she was getting fucked. As I stroked my cock, I enjoyed the feel of it getting hard as I knew exactly what I was going to do. I was going to embark on a mission. The operation would start gentle at first before building to the penultimate, sexual crescendo. I was going to engage on the task of corrupting Cindy. My cock glistened with pre cum at the very thought as I continued to wank, I brought myself to a climax before stopping again. I liked to tease myself and by the time I fucked Cindy, I wanted my balls to be full of come.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Neighborly Husband shares beautiful wife with older black neighbor.in Interracial Love
My Mom's Disgusting Boyfriend How my mom's bf ultimately seduced me.in NonConsent/Reluctance
You Can Go Home Again She destroyed his life. Can she build it back again?in Loving Wives
IWillSubmit38 Pt. 01 He chose to drug and take her to protect her from herself.in NonConsent/Reluctance
Choices She made hers, and I made mine.in Romance
More Stories