The Spectator Ch. 03

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Jack and Cindy play a game of Truth or Dare.
3.6k words
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Part 3 of the 3 part series

Updated 10/29/2022
Created 12/11/2014
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Jack finished his hash brown and scooped up the last of his beans. Sitting back in his seat, he stretched causing his jumper to ride up slightly giving Cindy a brief glimpse of the run of downy dark hairs on his stomach that would lead down to his cock. She knew that hangovers always made her horny and today was no exception. The earlier orgasms had now been forgotten as she felt herself feeling aroused again. She wondered what Jacks cock looked like and felt herself moisten at the thought.

"That was a breakfast fit for a king." Jacks voice pulled Cindy back from her horny musings. "For someone so small you sure can put it away yourself.''

Cindy grinned "I have a healthy appetite."

Jack looked at her intently "Í bet you have."

The intensity of the moment disappeared as quickly as it had arrived leaving Cindy feeling momentarily unnerved and excited at the same time. Was that a sexual connotation or was she just allowing her current hangover to mash all rational thought? She thought back to Jack's Truth or Dare question from the previous evening and Cindy sensed that Jack could be dangerous and the thought excited her beyond belief.

"I could almost see Cindy's mind working over time when I reckoned she had a healthy appetite. Of course she wasn't aware that I was watching her play with herself earlier, but the voracious way in which she had used her vibrator had told me everything I needed to know about her. However to look at her now in her pyjamas and her blonde hair in a pony tail you wouldn't think she was naughty. I say naughty, because I was pretty sure her earlier performance in the conservatory had been for my benefit, I just had to find a way of her confirming that to me, but that shouldn't be a problem. I am a master at getting people to confide in me, they tell me their dreams but more importantly their fantasies. You see I am not just a master spectator I am also a proficient fantasy creator. The more someone releases themselves to me, the more intense their experience is it's as simple as that.

As I helped Cindy clear the table, I knew she thought I was a bit edgy and perilous and by her body language I didn't think she would mind one bit. I was looking forward to taking her on a journey she would never forget."

Jack followed Cindy through to the living room. Kneeling in front of the log fire, Cindy lit a pile of logs with an expertise that impressed Jack. Most women wouldn't know how to light a pile of wood if their lives depended on it. Quickly, the logs took light, filling the living room that had been darkened by December morning with a warm amber glow. Standing up, Cindy switched on the fairy lights that adorned the mantelpiece. Her hangover was thankfully abating and as Jack settled himself on her sofa, Cindy hoped he was planning on staying.

"So how was I going to suggest I stayed for a while without sounding like a plank of wood? I hadn't felt so interested in anyone for a very long time. It had been a lot longer than I cared to admit to be honest. Usually, I preferred no strings attached sex and feeling too much interest in one person was alien to me. Not that I was a loner who sneaked around invading peoples privacy I hasten to add.

As Cindy settled herself in the armchair facing me, I decided to deal with the situation head on. I didn't want her to feel uncomfortable or compelled to entertain me, although the thought of Cindy entertaining me in a sexual fashion was exciting me more than I cared to admit. I was aware that total corruption needed to be taken one step at a time. So, I relaxed. To complete a mission, I had to be in total control of the situation to determine success."

"I can go if you want to recuperate alone. I was only calling round to help ease your hangover, I didn't expect breakfast." Jack said, trying to sound as casual as possible

Cindy waved her hand in dismissal. "No seriously, stay. I could do with the company. I don't have anything planned for today, plus I'm feeling better already."

Jack raised his eyebrows. "I take it the grease of the full English breakfast is successfully soaking up last nights alcohol?"

Cindy laughed. "Yeah, something like that, plus your vitamin C dosage has helped. I just feel tired, that must be my liver trying to bring itself back to life."

"Well, feel free to go back to bed if you like, I won't stop you." Jack gave her another of his intense looks before adding, "I wont be offended."

Cindy held his gaze. "I promise you I'm fine."

Suddenly the thought of having Jack wrapped beneath her bedcovers naked entered Cindy's mind. There it was again, the sexual connotation in his voice followed by that really horny slow smile, crossing over Jack's lips; she knew she hadn't imagined it. Jack was flirting with her and it made her feel all warm inside.

"I decided that I needed to determine how much of last night Cindy remembered. As she leant over the armchair to grab her glass of orange juice, her pyjama bottoms started to ride down, slightly showing me the line of her pert bottom. I felt myself feeling instantly aroused. I wanted to pull them down and lick her from back to front. I experienced an overwhelming desire to taste her as she came in my mouth before fucking her hard and throwing her around the bedroom. There has always been something really appealing to me about petite girls, they reminded me of rag dolls, and I hoped Cindy would be as versatile. I stopped the thoughts as quickly as they entered my mind. Back to my mission, did Cindy really remember anything from the night before?"

"Do you remember anything from last night?" Jack casually asked as Cindy readjusted her pyjama bottoms and settled herself back in her seat.

"Of course I remember I wasn't in a totally comatose state was I?"

Jack shook his head. "No. The Truth or Dare game do you remember that?"

Cindy felt a flush of heat run through her from the top of her head to the tip of her toes. "I remember." She conceded. "I remember thinking I can't do a dare because that might have involved me making some kind of movement."

Now it was Jacks turn to laugh. "Don't worry, I wouldn't have asked you to perform anything too ambitious."

"That's a good call." Cindy replied feeling a sudden urge to touch herself. "I remember your truth question if that's what you are getting at."

Cindy twirled her hair in her fingers aware that she had adopted a coquettish look that she was hoping would drive Jack to distraction.

"Did it turn you on?" Jack candidly asked.

Cindy nodded a flush of pink diffusing her face. "It did yes."

As the sexual tension picked up a pace Jack felt more confident about taking things further.

"I was thinking we could play the Truth or Dare game sober. In my opinion and tell me if you beg to differ, but I think it would be the perfect way to spend a Sunday." Jack shrugged as casually as he could muster seeing as his cock was suddenly taking on a life of its own in his jeans at the very thought.

Cindy felt herself stir inside at Jack's suggestion and she couldn't believe how daring she felt in his presence. "That sounds great to me."

"Game on."

"You go first." Cindy tucked her legs beneath her making herself more comfortable. She hadn't been this turned on for many years.

Jack leant over and put his cup of coffee on the small table beside him before sitting back on the sofa. "Okay. Truth or Dare?''

"Truth." Cindy replied.

Jack folded his arms, leaning forward he rested them on his knees and looked intently at Cindy. "When you played with yourself this morning did you know I was watching?"

Cindy shook her head, "No but I was fantasizing you were. Then that thought led to another and another." She paused. "You must have seen the result?''

Jack arched his eyebrow approvingly and nodded, a self satisfied smirk danced across his lips. "I certainly did and it was quite a good show, you made me hard. Have you ever played with yourself in front of someone before?"

Cindy waved her finger at him. "Not telling, then you would be getting two truths for the price of one."

Jack smiled. "You can't blame a man for trying can you? Anyway, it's your turn to ask me."

"Okay, Truth or Dare Jack?"

"I will choose Truth, it's too early in the game and in the morning for me to be accepting dares."

Cindy pursed her lips in thought. "What is the naughtiest thing you ever done? I mean sexually of course."

Jack nodded. "I knew exactly what you meant Cindy."

"I obviously wasn't going to divulge the naughtiest thing I had ever done to Cindy so soon. I didn't want to scare her away before my plan of corrupting her had taken off the ground so to speak. However, I did wonder if possibly I was doing Cindy a disservice. Maybe she wasn't as innocent as she looked. After all, I needed to take into account that she'd imagined me watching her that morning as she'd made herself come. I decided to give her a mild version of events of the first time I corrupted someone. I needed to gauge Cindy's reaction and see how far I could take her, which I hoped was the absolute pinnacle of corruption, I could feel my cock stir at the very thought."

"I can't divulge the naughtiest thing I've done. I believe in taking things slowly, whether you believe that or not is up to you?" Jacks eyes twinkled at her, and his teasing smirk reappeared across his lips.

Cindy blushed. She felt like she'd made a real fool of herself. Jack watched the pink tinge creep across Cindy's cheeks, allowing her to feel a slight moment of embarrassment before bursting out laughing. He leant over and put his hand on her knee causing a thousand volts to surge through her.

"I'm only joking. I'll tell you one of the naughty things I have done but not the naughtiest okay?"

Cindy looked at him and shook her head. "You need to stop teasing me."

Jack lightly stroked her knee with his fingers. "Now, where would the fun be in that? Anyway, I will never be able to stop doing that, it's in my nature and hopefully you will enjoy me teasing you for a while to come yet."

Leaning back on the sofa Jack paused momentarily and looked up at the ceiling as if trying to wrack his brains for a suitable story to tell before looking back at Cindy. He folded his arms to his chest. "Okay, I met a girl at university. She wasn't the prettiest girl on the campus but there was something about her. She dressed a little quirky with striped tights and mismatched skirts and jumpers. On anyone else the outfits would have made them look like a rag bag of mismatched nonsense but Lucy carried the look off with aplomb. She had flaming red hair and creamy, pale skin that only served to enhance her almond shaped green eyes. We started talking one day as we were both sat in the university cafeteria waiting for our lectures. We got on really well and arranged to meet in the bar that evening for a beer. We started seeing each other from then on and after a while, well, three weeks to be exact we slept together. She wasn't very adventurous at first, very much your typical missionary girl; she was really inexperienced and I suppose I found that a bit of a turn on if I'm being honest. Eventually with some coaxing she opened herself up to me in more ways than one. Once I started to introduce her to different things it was like she couldn't get enough.

It was near the end of the semester when we were all due to go home for the summer holidays that she confessed that she had a boyfriend back home."

"Did that bother you?" Cindy asked.

Jack shook his head. "Not really. I was young, dumb and full of come, we'd had our fun and I knew that when I got back home I wouldn't find it difficult to find some other girl who would be willing to entertain me but I found myself wondering what Lucy was going to be like when she got home and started fucking her boyfriend. It was obvious that he would soon be wondering how the hell his innocent girlfriend had gone away to Uni and had returned after suddenly developed a penchant for sucking cock and anal sex. I assumed that before she had left for Uni Lucy's boyfriend had been used to making love in the traditional sense, not having someone bouncing on his cock with her arse. I brought the matter up to her as I watched her pack her suitcase ready to leave the next day. As she hauled her packed suitcase of the bed she placed it at her feet and smiled at me."

"He'll be in for a treat Jack won't he? I'll just tell him that I've grown up and been watching a lot of porn. What the eyes can't see the heart cant grieve over eh?"

I remember thinking at the time that it would be a great sight to see, sweet innocent Lucy of old gone and the new Lucy corrupting her boyfriend with all the stuff we had done. I told her to knock on my door the next morning before she left because I would have a present waiting for her.

Cindy raised her eyebrows and Jack laughed. "I know what you are thinking and it wasn't that kind of present, it was something far more exciting in my opinion than that. Anyway, she agreed and that afternoon I went out shopping. The following morning she knocked on my door as arranged and I gave her the present I had bought. She ripped off the wrapping paper, her eyes shining like a child opening their first Christmas present and there it was, a webcam. She looked at me a little confused and then I explained by reasoning behind this very unromantic gift. I thought she would be reluctant about carrying out my plan at first but then she smiled and bit her lip. She agreed to add me to Skype and let me watch her fuck her boyfriend without him knowing.

I didn't hear off Lucy for around three weeks and I thought she had decided to forget our little arrangement but one night I received her Skype request. I accepted and we chatted, I outlined what I wanted her to do and the plan was very soon all in place."

Cindy could feel herself move into a horny plain that she'd never experienced before. She imagined Jack in his bedroom, lay on his bed wanking as he watched Lucy corrupt her unsuspecting boyfriend. She could literally see the scenario unfold in her mind. She imagined Lucy undressing, her dress slipping to the floor, her body decked out in horny sexy lingerie. Cindy imagined her lying her boyfriend down and taking him in her mouth deep as Jack watched.

"Hello, Earth to Cindy?" Jack's voice interrupted her reverie.

"Sorry, I was just thinking that's all." Cindy's voice trailed away.

Jack smiled. "You were imagining it wasn't you?"

Cindy nodded and bit her finger. God, all she wanted to do now was to fuck Jack. Her pussy was aching to feel him deep inside her. She wanted him to corrupt her like he had obviously corrupted Lucy. That was the only coherent thought that was present in her mind that was a mish mash of images of Jack watching Lucy perform, Lucy fucking and the shock on her unsuspecting boyfriends face.

"The minute Cindy had adopted that faraway gaze in her eyes; I knew she had been imagining it all. I got a kick out of making her use her own imagination, after all, the mind is the most powerful of tools a human possesses. It would have taken the kinky edge off the whole thing if I'd gone into a graphic description of what I watched that night and now was the perfect time for me to see if Cindy would accept my advances."

"Ok, now I've answered your Truth or Dare question Cindy, its your turn. Do you want truth or are you brave enough for a dare?"

Cindy felt her mouth go dry, it was as if all her fluids had gone down South and were pumping out of her pussy.

"Truth." She answered.

Jack looked at her intently. "Do you want to see my cock?"

Cindy nodded. Her heart was banging in her chest as Jack stood up and unzipped his jeans and pulled out his cock, feeling a thrill as he watched Cindy's eyes leave his face and look down, the smile that lit up her face was all he needed to know. Cindy watched as he expertly stroked his thick length. All sense of right and wrong left her in an instant. She wasn't the sleeping around type but Jack with his stories and his Truth or Dare game had opened up something inside her that she never knew existed and was sure would never be closed again if she allowed herself to be part of Jack's world but she didn't care. She felt daring, she felt unbearably horny and for the first time in her life she knew what she wanted.

"I am going to dare you Cindy. A truth and a dare for the price of one but I can be forgiven for being a little cheeky seeing as you can see what you have done to my cock. So, I dare you to come over here and suck me and I want you to imagine that you are being watched."

"I could feel my cock begin to throb as Cindy moved off her chair and made her way across the living room floor on all fours. Her mouth was just begging to be fucked and when she knelt before me I stroked her face as she expectantly opened her mouth. I put cock inside and felt her tongue swirl around the tip before she took my whole length in her mouth in one. The warmth of her mouth my cock felt like it had died and found a whole new Nirvana. She sucked me slowly at first before picking up pace with a hunger that astounded me and encouraged me to thrust my hips in the same rhythm I would use if I had been fucking her pussy. The juices from her mouth slid down my cock and onto my balls. I reached for my mobile phone off the arm of the sofa and moved it into video mode and filmed her as she gagged on my cock before taking it out of her mouth. Slowly she started to wank me, her eyes looking up at me all the time as she did so. I could feel myself reach number eight on my personal coming scale and then I stopped her. I didn't want to come. Not yet."

As Jack pulled his cock away from Cindy she looked up at him, a mist of confusion crossed her elfin features. Jack looked down at her and smiled.

"I don't want to come yet."

Cindy couldn't help but feel a stone of disappointment to drop inside her stomach. She had been so looking forward to Jack fucking her.

Jack put his cock back inside his pants and sat down so his face was close to hers. He leant forward and kissed her, wiping the juices of her cock sucking from her face.

"I want to fuck you. Is that what you want?" He murmured.

Cindy nodded, of course she wanted him to fuck her, she felt like her pussy was ready to explode.

"Do you like the idea of being watched?" Jack asked. His eyes searching hers, he wanted to see honesty from her. There was no point him continuing if Cindy was in any way reticent about the idea. Cindy nodded, right now the way she was feeling the whole street could have been in the house watching Jack fuck her for all she cared.

Jack stood up and pulled Cindy to her feet. He put his arms around her and kissed her, his tongue probing her mouth before expertly finding hers making her feel weak with desire.

"Do you want to go out tonight? There's somewhere I would like to take you. I think you'll love it."

The huskiness in his voice suggested that where he was going to take her would be somewhere she would never forget. Cindy felt a tinge of fear mixed with excitement but her desire to be fucked by Jack meant that there could ever only be one answer. She looked up at him, her eyes

"Mission accomplished, my plan was now in place."

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