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52. It's Her Night
Last Updated:
2024-07-12 23:42:17Related chapters
Guilty Pleasure 53. Asking for A Date
"Are you alright? Can I keep going?" Will checked to see if Anna was ready for the rest of tonight.“Yes, master.” Anna arched her back. “Please, don't tease me.” She pleaded. Will let out a breathy laugh and pecked her lips. "Whatever my girl asks for, she gets."Then he didn't wait anymore and pushed himself inside her in a go. Her walls immediately squeezed him so hard that it was almost painful. He threw his head back and let out a groan. He waited there for a few seconds, allowing Anna to get used to his size. Sometimes he wondered how she was still so tight.Will looked at Anna. Her eyes were shut and she had fisted the bed cover tightly in her grip. She was breathing heavily. “Open your eyes, babygirl. Look at me.” Anna slowly opened her eyes and made eye contact with him. Then he began to move slowly all the way in until his whole length was inside of her. He pulled all the way back out and repeated this action, making both of them comfortable and ready for the ride of the
Last Updated : 2024-07-13Guilty Pleasure 54. Sexting
The bed dipped under Anna’s weight as she just jumped on it with her phone after having a shower. Currently she didn't have much work as Will was working from home, so she only had to check files and arrange online meetings, sometimes keeping track of the office work. She was surely loving it like this. It was not because she had to work less, but because she was getting to spend more time with Will. She was getting to explore the sides of him which no one ever got to see. She was glad for that. For a change, Will had gone out to attend some meeting, leaving Anna alone at home. She was not required, so he asked her to stay back and rest. Once he left, Anna showered and fell on the bed. She was feeling so lazy that she didn't even try to take out her clothes and wear them. She only wrapped the wet towel around her body which was damping the bed cover. Anna rolled her eyes and sighed before throwing the towel away too. Then she was lying naked on the bed. She grabbed her phone from th
Last Updated : 2024-07-14Guilty Pleasure 55. The Dinner Party
The smoke from the hair curler surrounded Anna’s face. As she was done with her work, she kept the machine aside and stepped back to admire her work. For the first time in a long while, she felt her hair looked manageable. She brushed the long wavy strands of her hair one last time.“Done!”Anna was wearing a maroon velvet dress with queen anna neck and bishop sleeves. The perfect waves of her hair and the red lipstick she had put on made her look like she was ready to be featured on a magazine cover.“I hope the dress is okay.” She said to herself as still a doubt lingered in her heart. She sighed and stood up on her black stilettos and inspected her reflection in the mirror. The maroon dress reached a little below of her thighs and even though it was not too short, something about wearing it to a formal dinner did not sit well with her. Fiddling with her fingers, she bit her lips.Anna was thinking whether to change or not that’s when Alexa facetimed her. As soon as she received th
Last Updated : 2024-07-17Guilty Pleasure 56. He is Jealous!
"Get away from her.”Anna was feeling weak on her knees from before, but she felt weaker at Will’s voice, cold and deep, threatening to cut through her skin. She stood there as both the rivals stood face to face, both standing at the same height and same scowl on their faces."What the fuck do you think you were doing?" Will’s voice was no less than a thunder while his eyes were busy glaring at Oscar. The latter did not seem fazed at all. "I was only showing her the washroom." Oscar shrugged his shoulders. "But then she tripped over her own heels and so obviously I caught her.""You had your hands all over her body, Mr. Brown." Will growled in a stern tone. "And you think I'll believe you?"Behind him, Anna opened her mouth to confirm that what Oscar was saying was true, but before she could say a word, a sweet voice called out to Oscar and they turned back. "What are you three doing over here?" George Brown, Oliver Brown’s father held the arms of his son. "Is there a problem?"The
Last Updated : 2024-07-18Guilty Pleasure 57. A Challenge
“I want to see her tears.”Will looked at Anna’s face which was flowing with pleasure after the orgasm crashed through her frail body. But he wanted to wipe it off. She looked too tempting like that, when she had surrendered herself completely to him, but he had some other plan for the time being. He was not giving to give in to her pleasure anymore.“Master, please…..” Anna almost begged, arching her back and gripping the bedsheet tightly to fight the ache between her thighs. “I… I need you more, master. Please.”He smirked and pulled his fingers out of her. Then slowly and very measurably, he filled her up with his length. It was so excruciatingly overwhelmi
Last Updated : 2024-08-01Guilty Pleasure 58. Jealousy?
“If you’re looking for a challenge, then you’re gonna have it, my little slut!”As Will thought this, his unconscious mind reminded him of something else.“Or maybe not. I should have backed down.”They stood separately among a large crowd, but his eyes remained fixed on Anna. Standing amidst the crowd and bright shiny lights, Will realized how luscious and heavenly beautiful Anna looked even when her makeup was gone and she was standing with a bare face and natural curl. He also noticed how everyone around was stealing glances of her.Especially the male audience of the group…..
Last Updated : 2024-08-02Guilty Pleasure 59. What's Mine is Mine
Although Anna knew her destination, yet her heart couldn't help leaping as she saw the familiar building of Will’s penthouse come into sight. The drive till now had been unusually quiet as she was busy praying that he didn't hit anyone. It was a miracle that he actually didn't hit anyone, after all his speed was too rash. Anna had to clutch the seat belt tightly to make herself steady so that she didn't fly out of her seat.Will parked his car and they both stepped down from the car before Anna followed him inside the building with her stomach heavy with the anticipation which was about to come her way.He didn't bother till they reached their flat, let alone their room. He grabbed Anna by her neck once the door of the elevator closed and smashed his lips with hers. Anna gasped as she was not ready for it. But she g
Last Updated : 2024-08-03Guilty Pleasure 60. Arranging the Punishment
That evening when Will returned home, he found the house dark, only the dim lights were on. He called out Anna’s name a few times, but didn't hear anything from her. He walked inside their bedroom, loosening the tie around his neck and folding his sleeves, when his gaze fell on the mirror. He noticed a note was stuck there. He sighed, knowing it must be another of Anna's surprises. It got a smile on his face. Without wasting a moment, he pulled it off and after reading it, Will directly walked to the red room.Anna was shivering with anticipation as her plan was to have another memorable night, not that she didn't have one just last night. Still she was eager to be fucked by Will like there was no tomorrow. She was waiting impatiently for him to return and take her. She closed all the lights and waited for him in the red room after leaving a note for him, saying she would be waiti
Last Updated : 2024-08-05
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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
