Emma spent the day indulging in something she hadn't done in years—absolutely nothing. She sat by the pool, took a dip in the hot tub and even had a nap in the afternoon. It felt odd to head down for dinner by herself, but she figured it was either that or eat alone in her room. She conversed politely again through dinner, many of the guests the same as those she had spoken with the previous night. Though she was afraid it may become a habit, she indulged in a couple of glasses of wine again this evening, enjoying the relaxing sensation that spread throughout her body in response. When the meal was finished, she excused herself from the table and left for her suite to wait until Michael was finished with whatever was occupying so much of his time.
She hadn't expected Michael to be waiting in their suite when she walked in, but he was there, sitting across from the man she had seen him speaking with at dinner the evening prior. The lights were dimmed in the room and the two spoke quietly, looking comfortable and relaxed on the sofas. “Good evening, Em,” Michael spoke up as she entered the living room. “Hey there,” she replied to Michael, while nodding politely to his guest. “I'd like to introduce you to Ethan. He'll be joining us this evening,” he said smoothly. “Hello Ethan,” she replied. “And what is it exactly we have planned for this evening,” Emma teased lightly, having no way of knowing what Michael had in mind. “Well, Em. You remember the talk we had earlier today? Remember how you told me you trust me?” he queried. “Yes, of course. Why?” Now she was entirely perplexed. Michael nodded almost imperceptibly to Ethan and Ethan rose from the sofa in response and came to stand in front of Emma. “You're very beautiful, Emma,” Ethan began. “Thank you,” she responded uncomfortably, turning to Michael with a puzzled expression on her face. “Now is when I need you to trust me, Em,” he responded.
She wasn't sure if it was the wine, the strange situation or a combination of both that left Emma feeling confused and a little off-balance, so she didn't think to resist when Ethan closed the distance between them and began caressing her arms. But, when his hands began to trail over her hips and toward her ass, she stiffened. “Em, it's OK. Just let your body relax,” Michael spoke up, seeing her body's response. Ethan's hands continued to wander over Emma's body, back to her waist and moving up over her fabric-covered tits. She was trying to focus her attention on Michael's words, but the situation seemed rather absurd, and she didn't know exactly what his intent was at the moment.
She moved away from Ethan slightly until his fingers grazed over her nipples and squeezed gently. A moan escaped her lips. “That's it, Em. Just let go,” Michael coached. One of Ethan's hands remained on one of Emma's tits, as the other moved behind her neck to loosen the tie that held her halter dress. A quick tug and the tie gave way, and the dress fell to the floor. Tonight, she had decided to don the naughty lingerie, so she stood before him in a satin bra, thong and garter belt. Ethan returned his free hand to Emma's nipple, squeezing again gently through the satin. She tried to stifle another moan and then both of his hands squeezed her tits more firmly than she had anticipated. God, it felt good. Emma had never considered herself into rough play, but the firm way Ethan was squeezing her tits felt incredible.
Seemingly out of nowhere, Michael's hands were at her back, unhooking the clasp of her bra. It fell to the floor to join her dress and his hands reached around to replace Ethan's hands on her tits. Ethan leaned forward and sucked one of her nipples into his mouth as Michael's hands continued to squeeze her tits. After a moment, Ethan began to trail kisses downward, across her stomach, along her hips and down her thighs. She shivered and Michael's hands began to follow Ethan's trail down her body as he pressed firmly up against her from behind. Michael's fingers reached her clit before Ethan, and he rubbed slowly, making her press her pussy against his hand in search of more. He moved his fingers along her slit, spreading her lips open wide. He leaned her upper body back further against him, tilting her pussy upward and making it easy for Ethan to lean in and run his tongue along her open lips. Wicked sensations coursed through her body. Emma knew she should resist; this was something no proper woman would ever consider, never mind be standing naked in the middle of.
A moment later, Ethan stopped and spread out on the floor in front of her, and Michael guided her on top, arranging her pussy directly above Ethan's face. Michael pressed her down gently, and Ethan's tongue came out to lick her pussy lips once again. Without warning, he plunged his tongue deep in her pussy, thrusting in and out as fast as he could. Emma moaned loud and pressed down further to allow Ethan's tongue to penetrate deeper. Michael came around to stand in front of Emma, but before he could guide her head to his massive cock, she opened her mouth and took it in greedily. She had never really considered herself an expert at the task, but she had always enjoyed the feel of a cock in her mouth; the hard length, surrounded by such smoothness. She pressed further, trying to take the entire length of him into her mouth, sucking as hard as she could as Michael's cock thrust against the back of her throat. As Ethan continued to tongue fuck her pussy, she was wild with desire, grinding her pussy against his mouth and sucking the cock in her mouth with everything she had. In less than a minute, she could feel the pressure mounting until she began to cum, screaming against Michael's cock in her mouth.
Michael withdrew while he still could. He gently grasped Emma from beneath the arms and turned her around to sit on Ethan's face while facing his cock. Michael slowly guided Emma forward from the small of her back until Ethan's cock was poised at her lips. Instead of taking him in all at once, she stuck out her tongue and licked along the length of his cock while Ethan's lips latched onto Emma's clit and began to suck hard. No one had ever done that to her before, and she could not have anticipated the incredible sensations that coursed through her body in response. It was exquisite. In no time at all, she was fighting another orgasm as she opened her mouth and took Ethan's cock inside. He thrust upward to meet her, fucking her mouth with his cock as her body arched wildly and she lost the battle, cumming hard against his mouth. Ethan didn't stop, he continued sucking her clit hard and already Emma could feel her body revving up again. In the next moment, Michael was kneeling behind her. He shoved his cock into her pussy hard while Ethan kept pressure on her clit. She didn't know how it could happen so soon, but between the feel of a cock in her cunt and a mouth on her clit, Emma started to cum yet again, screaming loud enough to wake the entire deck.
When Michael withdrew, she thought it was over; she sucked hard on Ethan's cock, bobbing her head up and down, not ready to give up the cock in her mouth just yet. But, a moment later, Michael lifted her from beneath the arms again and helped her to straddle Ethan's cock. He didn't have to press her down this time, she slid down on his cock easily and began to ride up and down slowly. And then Michael was back. This time, he rubbed a lubed-up finger against her tiny ass hole. She should have resisted; that place was not intended for sex, she knew. But she was too far gone, enraptured with pleasure to resist now. Michael's finger slid into her ass slowly, and he moved it in and out, lubing it up with her own wetness. He withdrew and lifted her off Ethan's cock only to plunge his cock into her pussy briefly. When he withdrew, he forced her back down on Ethan's cock as he lined his up with her ass hole and began to thrust forward gently. The head of his cock slipped inside and he waited for Emma to relax. And then he was sliding the entire length of his cock inside her ass, stopping once he was fully inside to let her adjust again. He began to thrust slowly as she rode the cock beneath her in tandem. And then the she picked up her pace, fucking both cocks faster and faster. Michael spread Emma's ass cheeks to shove as deep inside her ass as he could. The sensation of her pussy and ass being filled and fucked at the same time was incredible, and Emma began to cum hard, spasming around Ethan's cock, provoking his own orgasm as he pulled out to cum all over her pussy. A few more thrusts and Michael was done for too, and he shot his load deep inside her ass.
Michael withdrew and lay down on the floor like he had the previous evening. Emma
collapsed beside him; her entire body felt like gelatin and she was afraid her hands and knees wouldn't support her much longer. As Michael wrapped his arms around Emma, Ethan stood, slipped on his clothes and left the suite quietly, happy to see the Emma looking so relaxed in his buddy's arms. “But man, she was an amazing fuck!” he thought to himself with a smile.
Michael was quiet at first, experiencing a moment of uncertainty in the aftermath of his great plan. But then, Emma propped her trembling elbows up on his chest, “Why did you do that, Michael?” she asked. The question did not seem accusatory to Michael, simply curious and a little uncertain herself. “I wanted you to be able to experience a whole different side of sex; the side that is all about letting absolutely every inhibition go and enjoying what's there to the fullest. I knew I couldn't really have you, until you were all there for you to offer,” he explained. “Are you OK with that?” he asked. “It was incredible, Michael. I had no idea sex could be like that—that I could be like that,” she responded, still amazed by her own participation in the evening's events. She smiled realizing just how naughty it turned out she could be, and she realized that she was grateful to Michael for bringing this realization about. “You know, I'm kind of wondering what other unorthodox ideas you may have to help make sex a comfortable and natural thing...”
THE END
Billionaire Stepbrother
Chapter 1
Cathleen woke up with a pounding headache. She knew that she wouldn’t be able to party like that for another couple weeks. Final exams were right around the corner and it was definitely time to buckle down. Trying to finish school and run her own business was a lot harder than she had ever imagined.
But she was happy that she had proved the naysayers in her life wrong. So many people, especially her mother, had tried to tell her that she was taking on too much responsibility and she would probably end up burning out before she completed school. NYU was demanding enough. Who in their right mind would consider adding to that heavy academic burden the responsibility of running a cupcake business?
“I don’t see why you can’t find a job at some high-end bakery somewhere,” her mother had said on more than one occasion. “You’ve always felt the need to do things on your own. I just don’t understand it.”
Cathleen would shake her head and bite her tongue whenever her mother began complaining about the choices that she was making. She loved her mother but they were very different people and that was something that they were just going to have to accept about each other.
Her mother, who was about to be married for a third time, couldn’t stand to be without a man in her life. But it seemed like the minute a new man came into her life she began doing everything in her power to make his life hell, insuring that he would soon leave her. And that’s what often happened.
Maybe watching her mother’s relationship troubles had given Cathleen her strong desire for independence. She couldn’t see herself submitting to a man. She relished her freedom and independence far too much.
“No woman truly wants to be alone and independent,” her mother would tell her. “You just haven’t found the right man that’s all. But when you do, you will have no problem submitting to him. Trust me.”
“Sure. Whatever you say mom,” Cathleen would respond with a snicker.
She was scheduled to meet her mother for brunch in the West Village at 11. She had an hour to get in the shower and head out the door. Being late would just give her mother another excuse to begin nagging her about working too hard, burning the candle at both ends and all of that stuff. She already had pounding headache. The last thing she needed was a morning lecture. She would have preferred to cancel the meeting but she would have felt bad about standing her mother up at the last minute.
“I was beginning to worry about you,” Cathleen’s mother said. “You’re almost ten minutes late. I was about to start making calls.”
Cathleen sighed and sat down at the cafe table. Le Parisien was one of the hipper and more expensive eateries in the West Village, precisely the kind of place that Cathleen’s mother loved to be seen in.
“I’m fine, mom. You know how the subway can be sometimes.”
“Are you sure that you didn’t spend the night with a boy? You seem a bit hungover.”
Cathleen frowned and looked away. This was one of her mother’s favorite topics: Cathleen’s love life or lack thereof.
Her best strategy in these sorts of moments was to switch the subject to her mother’s romantic life and these days that meant the up and coming wedding to Warren Daughtery, owner of one of New York’s most prestigious Real Estate companies: Daughtery Properties.
This would be her mother’s second marriage in the last five years and her third overall.
“How are things progressing with the wedding? You guys haven’t called it off yet, right?”
Cathleen’s mother cocked her head to the side and stared at her sharply. Her light green eyes hadn’t lost their intensity after all these years. The lines around her mouth and eyes revealed that she had lived a life of fun and adventure. Summers in Paris, winters in Argentina and Brazil. She was a woman who loved to stay on the move. She also loved to shuffle men in and out of her life. As she approached fifty, her mother still had a sexual magnetism capable of attracting men decades younger than herself.
“No, we haven’t decided to break it off. Thank you very much. And I don’t see why you can’t just be happy for me.”
“I am happy for you but—”
“You don’t know anything about love. If you did you wouldn’t be so cynical.”
“Mom, you’ve known this man for eight months.”
“That’s not true. I’ve known Warren for almost twenty years. He was a friend of your father’s.”
The word father made Cathleen tremble. It had been almost ten years since he had died suddenly while they were on vacation in Cancun.
“Don’t you think that there’s something wrong about marrying a man who used to be friends with dad?”
Her mother’s face turned bright red. Cathleen felt bad for pushing the subject. She knew that her mother still held herself responsible for her father’s sudden death even though the doctors had repeatedly assured her that she was not responsible. Even if he hadn't stopped taking his medication during the trip he might still have suffered a heart attack. There was just no way to predict those sorts of things.
“I’m sorry, mom. I’m just really stressed right now with school and the business. It’s definitely more work than I had expected.”
A slight smile crossed the older woman’s lips. “You see, your mother isn’t always nagging you just to be a pest.”
“I know,” Cathleen said, reaching across the table and putting her hand on top of her mother’s.
“And there’s one more thing, I forgot to tell you,” Cathleen’s mother said, her eyes lighting up with excitement.
“What?”
“You’re going to meet your stepbrother this week.”
“Do I have to?”
“Yes, you do. In just a couple of months we’re all going to be a family.”
“Is he flying in?” Cathleen asked.
“No, silly,” her mother said. “He lives on the Upper East Side.”
Cathleen repeated the words the Upper East Side a couple times under her breath. She probably shouldn't have been surprised that her newest stepsibling was a spoiled, rich kid. That made sense given his father’s wealth. But there was just something so intimidating about the Upper East Side. That was old money territory, home to New York’s wealthiest families. It was a part of the city that she rarely visited. And when she did make her way up there, she never felt comfortable.
“Great,” Cathleen said with a snicker. “So I have to spend time with a spoiled brat this weekend instead of preparing for exams.”
“Don’t be so quick to judge him. You might end up of liking him.”
After they finished their meal and mimosas, Cathleen said goodby
e to her mother and they promised meet again the next week. Cathleen was glad that she hadn’t cancelled. It felt good to spend time with her mother. Even though the nagging could be annoying at times it was still nice to know that at least she had someone in her life who cared enough about her to stay on her case.
It was Saturday evening and she wanted nothing more than to head out with her friends. But she had two finals and an essay hanging over her head. And then there was the little problem of running her growing cupcake business, Indulgence Cupcakes.
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