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39. He isn't the Only One Winning
Last Updated:
2024-06-27 23:34:43Related chapters
Guilty Pleasure 40. His Lost Stress-ball
It was one of the random days in the office when a naughty idea sparked into Will’s brain. So, he called Anna into his cabin in a hurry. As soon as she got his call, she almost ran to see him as his voice sounded stern. “What’s wrong, Mr. Johnson?” Anna asked as she entered his office to see Will, sitting at his desk looking very upset and stressed about something.He tried to hide the smirk which was threatening to appear on his face. “Something is terribly wrong. Have you seen my stress-ball?" He asked her anxiously.She frowned because she had noticed that he almost always had a red rubber ball in his hand, squeezing it repeatedly to keep himself calm and collected.Anna tried to think, if she had noticed it anytime soon. "No, sir, I haven't. Do you want me to have a look around and see if I can find it for you?""Yes, Miss. Fox, it's very important that I lay my hands on it, I can't focus on my work without it. It’s very essential."She nodded her head and for the next half an ho
Last Updated : 2024-06-28Guilty Pleasure 41. Why so Tight!?
Will reached across his car and grabbed Anna’s cheeks and pulled her face closer to him. He smashed his lips with hers and began to kiss her mercilessly, forcing his tongue into her mouth. He was tasting each corner of her mouth, not giving her any chance to kiss him back even though she was trying her best to match his level. He used his other hand to grab her whole neck and pull her across the car until she was on top of her. “Will is literally manhandling me! Manhandling the way I wanted him to, the way I have always thought of, the way I have imagined after reading the books he has in his red room. He has no idea that I have read them when he is away, hopefully he never finds out anyway. When he pulled me across the car, I was a bit startled as he held my throat and I struggled to breath for about 5 seconds.Fuck! How the hell the man is so damn sexy! So irresistible and alluring at the same time!”Anna’s mind was busy thinking all this while she could feel Will’s hard against h
Last Updated : 2024-06-30Guilty Pleasure 42. His Feelings
Anna had a strong feeling stuck in her stomach, stronger than ever that she had to cum, but it felt like it was something more. Will reached to her pussy and played with it. “Ahh…. Master… Ohhhh…” She began to scream his name. She couldn't help screaming her lungs out. She herself was not sure about what she must be mumbling but she was completely lost in the pleasure. “Yes, cum for me, babygirl! Cum!” Will breathed out speaking quickly as if he was waiting for her to cum first but it was so heavy on her. He also fumbled with his words as he was breathing heavily, gasping for air but it couldn’t stop him from doing his job. She closed her eyes tightly and her mouth was parted, trying to grab some air, still whimpering beneath him. “Ohh… Ahhh…. Urghhh…. Ahhhh…. Ummm…. Ohhhhh….”“Cum for me, my little whore! Fuck!” He started yelling at her in frustrationWill pulled her up by her hair and made her walk till the couch which was on the other corner of the room. Then he pushed her ches
Last Updated : 2024-07-01Guilty Pleasure 43. His Will
Will stood a few feet away from Anna, sipping his drink and staring at her chest rising up and down. A mischievous grin was adoring his face as he thought about what he was going to do to her. He couldn’t deny the thrill that ran through him as he thought over the possibilities. But his personal whore was different, she wanted pain and he was going to show her that she couldn’t manipulate him, he was still the one in charge. It was clear what she was expecting, what she wanted. She was trying hard to pull the blindfold off her face. Will finished the drink in a go, stood behind her and yanked her blonde hair harshly. Anna gasped and stilled when she felt his finger probing her ass, slick with lube, but she didn't resist. He held her firmly by the back of her neck, waiting for her to start thrashing around again, but she stayed still. She whimpered as he slid the plug in and cried out at the loss of contact when he removed his hands from her body.“Be ready for the night. When I retur
Last Updated : 2024-07-02Guilty Pleasure 44. Babygirl is Horny
“Can we go a little bit slower?” Anna clutched the seat tightly with her one hand and the other hand was holding Will’s hand. "Wherever we are going…..” She was getting scared as he merely dodged the looking glass of a parked car. Will laughed but it was different from his usual laughters. It sounded more like a boyish one and filled with excitement. He was enjoying driving his sports car after a long time.Anna stared at his face, noticing his expression keenly. She found him grinning which got a smile on her face too. It was the first time she noticed him smiling like this, else most of the time it was a fake or formal one. She decided that she could withstand a little speed if he was happy. She couldn’t help admiring the shine on his face. She had made peace with the speed until he almost ran a woman and her cat over, who were out on a blissful walk by the side of the road. The woman shrieked in fear and Anna screamed, covering her face with her palms inside the car. She removed
Last Updated : 2024-07-03Guilty Pleasure 45. His Forbidden Guilty Feelings
“But you didn’t say I can’t tempt you.” Anna bit down on her lips and trailed a finger down her body until it came to a stop on her soaking core. "Instead you encouraged me a few minutes back, remember? I won't stop you if you decide to change your mind." She tantalizingly rubbed her pussy, giving him a challenging look. She was in a mood to be a brat again today. "But if you don't, you're free to watch. I’m giving you a live show.”Will was stunned. He always knew her as his most obedient submissives. He always loved that submission of her, but he also enjoyed the way sometimes this bratty side of her came out and she left no stone unturned to tease him and get into his nerves. Not to mention he enjoyed the aftermath too, when he punished her for breaking the rules and disobeying him. He moved his gaze back to Anna.She parted her thighs as far as she could and continued to rub her pussy, throwing back her head in pleasure and her eyes were shut tightly. For once, he looked down at h
Last Updated : 2024-07-04Guilty Pleasure 46. Treat Like Other Submissives
Anna was impatiently tapping her feet on the ground, occasionally stealing glances at the tall man sitting beside her, who was paying no attention to her, instead busy in his i-pad with a wine glass in his hand and his face was devoid of any emotion. She sighed as she felt Will was oblivious of her presence. "You've been going easy on me." Anna said suddenly, breaking the painful silence of the room and Will raised his head to look at her, his eyebrow raised ever so slightly as if asking her to explain. “Have you ever been this soft towards any of your other submissives? Then why me?” She saw the muscles of his jaw tightened, but he still managed to keep his face away from showing any expression. She got up, walked near him and stood right in front of him. “Though you don’t say, but I know that you don't fuck me like your other submissives." Anna looked straight into Will’s eyes. She didn’t even have a moment to squeal as Will almost jumped out of his place and grabbed her throat,
Last Updated : 2024-07-05Guilty Pleasure 47. She Found Joy in Pain
A silk cloth was wrapped around Anna's eyes, turning the world around her into darkness. She gulped, trying to make herself comfortable on the surprisingly soft bed on which she was currently sprawled across with her hands and feet tied to the bedposts. Will had seen everything, yet she felt too exposed, embarrassed and helpless as she lay there, waiting for him to touch her.Anna couldn't see anything, but she could hear everything happening around her. There was a little rustling sound beside her which disappeared after a moment. Then, she heard it again. It was loud and there was no mistaking it. The scratch quickly turned into a silent hissing sound of fire and she felt her breath stuck her in her throat, gasping for air. It was lighter as far as she could recognise. He had lighted something and she knew well what it was.“Master!” It came out no less than a whisper and sounded more like a plea, but she didn't know what she was pleading for. “I’m here, babygirl.” Will’s voice wa
Last Updated : 2024-07-06
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Guilty Pleasure Epilogue
Anna wrapped her hand around Will’s waist, making him smile. She sure loved cuddling. He moved her hands gently, pushing himself off the bed. He looked back at her with a content smile.“She's so beautiful and she's mine and I love her so much.”Staring at the time, Will’s eyes widened. He had just thirty minutes to get everything done so he rushed to the kitchen, made a simple dish, scattered roses as fast as he could all over the floor and bed. When he was done, he placed the food tray on the bed and held the flower bouquet in his hands."Darling?" He called her but she didn't budge, so he called her again.Anna groaned, pulling the pillow closer to her bo
Guilty Pleasure 80. Getting the Reward or Not
Anna laid still, eager for the punishment to begin. Her stomach was churning with butterflies and her heart was racing. She was both eager and cautious to experience the punishment. Will would never do anything to intentionally hurt her, so she pushed the cautious side away.Will brought her out of her trance with a harsh slap on her right ass cheek. It was hard, not showing any mercy. Anna stiffened before relaxing as the pain subsided. She exhaled, her fists clenched around the bedsheet and she began to count. He hummed, and gave her another blow. This time it was on her left ass cheek with the exact same force he used on her right.Pain. That was all she seemed to be feeling right now.He spread her legs a little for a
Guilty Pleasure 79. A Deal
"My little daredevil!” Will nodded his head. "The night isn't going to end any time soon. I would never leave my giri unsatisfied."He was rubbing Anna’s thighs who was already aroused from the previous encounter. Her panties were sticky and she was both hungry and needy. This caused her to close her legs swiftly, pressing them together to create friction. Will chuckled and pulled her legs apart. She whimpered and was annoyed by the way he was taunting her. Her body both craved his touch and she needed to cum."Soon, baby, soon.” Will said. He always seemed to have a trick up his sleeve. Every trick he had up his sleeve usually resulted in either pleasure or painful pleasure for her. Will
Guilty Pleasure 78. Daredevil Gives A Blowjob
“Are you fine?” Will asked in a concerned tone. “You’re sweating. Are you feeling unwell? Do you want me to reschedule?”Anna immediately nodded in no. “No. No. There's nothing wrong with me.”He shook his head, beginning to drive. She was excited to find out what he had planned and where he was taking her. While they were driving to their destination, Will filled in the silence by making small talk."Are you sure, you’re fine?"Anna sighed. "If you want me to be completely honest, I'm very nervous." She admitted, laughing.
Guilty Pleasure 77. Preparation for the Date
The week flew by quickly and Anna found herself getting ready for her first real date with Will. He and Anna had gone out a lot, as colleagues, maybe as friends with benefits, but never as lovers or a couple, hence why she called 'real date.Friends with benefits...That made her wonder, what exactly were they? Will never asked her to be his girlfriend or admitted clearly about having any sort of feeling for her, so she knew they weren't in a relationship. That’s why Anna just took this as they were both more than friends but not in a relationship. The sub and dom relationship was a long forgotten one as both had broken all the rules and went way past that.Yes, it was a bit confusing, wasn't it?
Guilty Pleasure 76. When's the Date?
"So when's our date?" Anna asked.With a warm smile on his face, Will turned to face her. "This weekend."Anna nodded with a thought that it was on the next sunday and she would have an entire week to pick a perfect outfit. She smiled at him. "So what shall I wear? What are we doing? Where are you taking me?"His eyes shot open as he heard her continuous questions. He threw his head back and laughed, seeing her desperation. "Ummm….. Wear something comfortable. As for the rest of your questions, you don’t need to worry about anything else, babygirl." He said, basically shrugging her off from asking further questions.
Guilty Pleasure 75. Isn't It Enough?
"I'm not gonna fuck you in a fucking hallway." Will groaned, more to himself.Anna looked into his eyes, waiting for his next move. Her breath came in short as his warm lips touched her nose, melting all her doubts and cautiousness in one stroke. Leaning in, she picked up her face to kiss him but little did she know that the intentions he had with her were far from the soft touch he had shown her. He simply picked her up and walked inside a room on the other end of the hallway and threw her on the bed.One of Will’s hands came down on her throat, forcing her back on the bed as Anna tried to sit. She gasped, closing her eyes to relish the feeling of his fingers closing in around her throat. The effect went straight to her stomach, and suddenly she was bereft of words. He loosened his hold and trac
Guilty Pleasure 74. Hallway
“Is it bad that I actually want him to do exactly what he just said to me?”Anna could feel Will’s glare on the side of her face but she chose to ignore it again. This man had some sort of obsession with always staring at her and she couldn’t deny not liking it."Don't stare at me like that." Anna dared to whisper.Will smirked and stepped closer to her, reducing the little space between them. "Am I not allowed to stare at what is mine?" His deep husky voice made her shiver.He was right, she was, there's no room for argument there, he had already made it pretty clear. He always kept it c
Guilty Pleasure 73. Burning Needs
Will and Anna drove home in almost silence. A song playing on the radio was the only sound in the car.Anna watched the city lights flash by as Will weaved in and out of the heavy city traffic. She kept thinking of things to say, but couldn’t muster the willpower to actually speak them out loud. She was afraid that she would say the wrong thing and ruin everything, so instead she stayed quiet.The feeling that blossomed when he kissed her stretched between them like an invisible string. She could not quite put her finger on it, but in that moment she swore she felt something between them changed. It wasn't the kiss that did it, Dod knows there had been plenty of physical interaction between them in the past months.No, it was the look in his eyes when he pu
