Cheating Destiny

This is part 3 in a series.

CHEATING DESTINY

It was a Friday afternoon and Destiny was just finishing up in her office when her boss walked in. Lou Anne was the one who had started the party planning service six years ago and had hired Destiny right out of college. She was in her late thirties now and had built this company from scratch. Even though she was now successful enough to take a step back and hire more people to do her job she never slowed down. She loved meeting and taking on new clients and all the running around that came with it. However, today Lou Anne had come to Destiny to talk about the very opposite.

"Hey Destiny, I just wanted to remind you that I'm leaving for my family reunion in a few minutes, and I won't be back until Tuesday. Are you still good to meet with that bride about her wedding on Monday?"

"Yes, I'm good to go. I've got all the wedding information right here on my desk and I promise to make you proud," Destiny said with a laugh. Normally, Destiny was the numbers girl. She took care of the accounting and most of her business with clients consisted of making sure their bills were paid. She rarely met with clients or had anything to do with the actual events they planned. However, she had been with the company since the beginning and was more than capable of handling a meeting here and there.

"I have no doubt that you will," Lou Anne said. "And it's straightforward. The bride just wants to go over the schedule and make sure everything and everyone is ready. Just ask her if there is anything else she needs and make certain all her deposits have cleared."

"I've got all that information right here. I guarantee you can trust me. Go and have a good time at your reunion. And I'll see you on Tuesday."

"Alright, I know you've got it handled. Enjoy your weekend and I'll see you Tuesday," said Lou Anne and then walked out of Destiny's office.

Destiny was only in the office for a few more minutes herself. She briefly went over the wedding file just to make sure everything was accounted for before filing it away for Monday. The wedding of Gwendolyn Adams and Harold Preston. Everything looked straight forward and according to Destiny's spreadsheet paid for. The meeting on Monday shouldn't be too complicated. All she really needed to do was double-check the bride's itinerary and see if there were any last-minute changes. She shut down her computer, grabbed her purse and headed out of the building. She needed to get home and change. She was going clubbing tonight with her friends. Last Sunday she and the rest of her friends had seen Leo off at the airport wishing him safe travels and lots of adventure. He had escaped Tia just as he said he would by moving out of his apartment and staying in a hotel his last night in town. Destiny and all of her friends had promptly blocked her on their phones and fortunately since Tia had never taken an interest in being friends with any of them, she had no idea where any of them lived or worked.

Tonight, they would all go out for some fun and dancing. Destiny showered and put on her favorite dress. It was red, short and had halter straps which were extremely flattering on her. Her hair was dried and curled, and her makeup done. Destiny had to admit that she looked damn good that night.

She had a fabulous night drinking and dancing. Plenty of men looked at her their admiration obvious but none approached her. Eventually she hugged and said goodnight to Tess, the last of her friends to leave. Destiny was alone in the club. She was going to leave soon but wanted to stay for one last drink. She ordered a martini at the bar, cooling down a bit now that she was off the dance floor. She was just taking a rather large swallow when she heard a voice say, "You are the most beautiful girl here tonight." She looked to her left and saw a very attractive man standing next to her. His next sentence was to the bartender to ask for a beer which he paid for immediately instead of putting it on a tab. He took a swig out of the bottle before addressing her again.

"I'm sorry, I know that's not much of a pickup line, but it is the truth. You are absolutely stunning. And I know this is incredibly forward, but the truth is I hate playing games so I'm just gonna put this out there. If you are interested, I would love nothing more than to spend the night fucking you senseless."

Destiny nearly choked on her martini. Was this guy serious? She stared at him in disbelief. "Are you joking with me? You can't really expect that to work, can you? I don't even know you."

Destiny looked him in the eye searching for any sign that this was a joke. But she could see none. He stared back nonchalantly without even twitching. He was an incredibly handsome man. Dark brown hair and piercing blue eyes. His nose was straight, and he had an aura of confident intelligence. He was a man accustomed to getting what he wanted, of that she was certain. And tonight, he wanted her.

The guy laughed. "I assure you I am not joking. And maybe this approach will work and maybe it won't. That is entirely up to you. Like I already stated, I hate games, so I won't play them with you. No, we don't know each other but that doesn't matter to me. I am not looking to date you. The only relationship I want from you is sex. I'm not ashamed to say it and be honest about it. I saw you tonight and you took my breath away. I want to fuck you. Hard. And I hope you say, yes."

Destiny couldn't deny that she was tempted. Just the fact that he had so boldly asked her had her a bit hot. But she couldn't go through with it, could she? It just felt wrong. Not to mention dirty.

She took a large swallow of her martini before replying. "You're very arrogant to approach me this way. However, I do like your confidence."

"I am a man not afraid to go after what I want. The worst thing that happens tonight is you say no and we go our separate ways. If you do come with me though I can guarantee to make it worth it. I do want to pleasure you so please don't think that I'm being completely selfish. I promise if you say yes, I will make your body scream in pleasure."

Destiny took another gulp to help her suddenly dry mouth. This guy was persuasive, no doubt about it. He was exceptionally hot and fit. One of the best-looking guys she had seen tonight. It would just be sex, nothing more. He was very clear about that, but Destiny wasn't looking for a relationship right now anyway.

"I won't go to your place. Nor will I bring you to mine. I don't know you well enough for that. If you want me, you can take me to a hotel."

"Absolutely," he replied. I'm actually new to the city and haven't moved to a permanent place yet. I'm currently living in a hotel not far from here." He paused and looked her straight in the eye. "So, does this mean, your answer is yes?"

Destiny could hardly believe herself. Somehow this felt wrong, but she was so turned on she couldn't help it. Then again, was being picked up at a bar by a stranger worse than paying a sex worker? She had already done that and had no regrets. Destiny appreciated the way he confidently approached her and put his cards on the table. No bullshit or lies. No promises he would never keep. This was exactly what she wanted. She hadn't actually had sex since her night with her mystery man. What she had done with Leo was great, but Destiny couldn't deny that she had been craving a real cock since she had taken her first one. And this guy was promising to deliver. She wanted him and she wanted him badly. "Yes," Destiny replied. "Yes, I'll spend the night with you."

The man grinned and he was so beautiful that Destiny's stomach flipped. "Wonderful," he said. "I promise your body won't regret it. I'm Tyler by the way."

Destiny laughed, only now realizing that they hadn't exchanged names. "Destiny," she told him."

"A beautiful name. It suits you." Destiny blushed. "Are you ready to go," Tyler asked her?

Destiny downed the last bit of martini in her glass. "I'm ready," she replied. She grabbed her purse. Tyler took her hand and led her out of the club. They walked out onto the sidewalk and turned left. "We'll go just over here," Tyler said. Destiny was surprised. There was a hotel just three buildings down, but it was one of the nicest, most expensive in the city. They quickly made their way over and into the lobby. She followed him into the elevator but was too nervous to even notice what floor he selected. The doors opened and Destiny followed him out and down a long hallway. When he stopped and opened the door to the room, he gestured to her to enter first. She walked inside and saw a beautiful suite. It looked designed for royalty decorated in purple and gold. As she walked further into the giant sitting room, she put her purse down on the coffee table and looked shyly at Tyler. He smiled walking over to her and kissed her gently. Destiny was a bundle of nerves. She was essentially about to have sex with another stranger although this time she knew his name and could see his face. Tyler pulled his lips away from hers and gently moved them to softly kiss her forehead. He placed his palms on the sides of her face and said, "Relax. I promise everything will be ok."

He then took her hand and led her to the end of the room where there was a partially opened door. Opening it the rest of the way Tyler led Destiny inside the most beautiful bedroom she had ever seen. Three of the walls were nothing but floor to ceiling windows and for the first time Destiny realized how high up they were. The view was incredible, overlooking the entire city all lit up in the night sky. And right in the middle of the dark room was an enormous bed facing the far wall so as you fell asleep you could look out to the night and the other skyscrapers reaching towards the heavens. Tyler suddenly started kissing the back of her shoulders and neck and rubbing his hands up and down her hips. Destiny realized that sleep was something she would probably get very little of this night.

Destiny turned in his arms. She then wrapped her arms around his neck and began to kiss him passionately. He opened his mouth to hers, Destiny slid her tongue inside his. He moaned in pleasure while unzipping the back of her dress. It fell to her feet and Destiny stepped out of it while also pulling his shirt over his head. Once his shirt was tossed to the floor Destiny took a step back to look at him. His body was amazing. Rich muscles and hard pecs. Beautiful abs that were partially covered by his jeans. He had no hair on his chest at all, which was a little disappointing to Destiny. She had always liked a man with a bit of hair on his chest. But what did it matter, Destiny thought to herself? She wasn't dating this guy, just fucking him. They had been very clear about that.

Then Destiny noticed that while she had been studying him, Tyler had been studying her as well. She was standing in front of him in a strapless bra and matching thong. Her shiny black heels completed the look. Judging by his slightly labored breathing and the obvious lust in his eyes he certainly liked what he saw too. Tyler then kicked his shoes off and Destiny unhooked his belt. She then unsnapped the button and pulled down his zipper. Tyler took over pulling his jeans and boxers off in one movement. Destiny didn't hesitate. She had been dying to try her newly acquired oral skills on someone. Leo had told her she was an expert before leaving and she wanted to test that out on someone new.

She lowered herself to her knees rubbing her body against his on her way down. She then took his partially hard member in her right hand and gently kissed the head. He was long, and although she wouldn't describe his dick as skinny, he wasn't as thick as Leo. She knew he expected her to start sucking on it immediately but instead she slowly stroked it with her hand and placed her mouth tenderly on his balls. She ran her tongue down the middle of them and then slowly took his right ball in her mouth. He gasped out loud and put his hands behind his head. She continued to suck on his ball while stroking his shaft with her hand. He panted heavily while she gently sucked and licked his ball. When she felt like he was ready she took her mouth away only to then suck his left ball into her mouth. The sounds he was making made her giddy, knowing that he was loving what she was doing to him. She was also getting incredibly wet between her own legs. After just a bit she thought she had tortured him enough and moved her mouth from his ball and finally took his shaft into her mouth. "Fuck," he cried, as Destiny moved her mouth up and down his now fully erect penis while still pumping with her hand. Fully erect, he was incredibly long. She licked and nibbled with her teeth, eliciting moans and curses from his lips. He was getting so worked up that he started pumping his dick into her mouth and Destiny took all of it down her throat. After her weekend with Leo, Destiny had bought some popsicles to practice taking something long and thick down her throat. And the practice had paid off. She didn't gag even once. He was obviously getting close to cumming and Destiny was getting ready to pull him out so he could spray her chest when he unexpectedly pulled himself out. He grabbed Destiny by her shoulders to pull her to her feet and quickly removed her bra and underwear. Tyler quickly led her to the bed and told her to get into doggy position.

Destiny did as she was told, hoping he didn't notice her slight hesitation. She had never had sex in this position and wasn't sure what to expect. Still, she kicked off her shoes and climbed on the bed lying her head on a pillow and sticking her ass high in the air. She thought Tyler would take her immediately, but he surprised her by gently licking her pussy. Destiny gasped and closed her eyes in pleasure. Neither her mystery man nor Leo had orally pleasured her in this position, and it was a slightly different sensation. The air could touch her vagina, so she had the feeling of both heat and cool at the same time. "Oh yes," Destiny sighed. "That feels so good." Tyler continued to lick her most sensitive spot and inserted a finger inside of her. He rubbed against her g-spot and almost before Destiny realized it was happening an orgasm was overtaking her body. She cried out in pleasure bucking her hips against Tyler's mouth and finger.

As she was coming back to earth Tyler said, "Don't move." He quickly moved over to the nightstand. There he fished a condom out of the drawer, ripped it open and slid it on his dick. In just a few steps he was back behind her and lining his cock up to her dripping pussy. She felt the head of his cock slip inside her where he paused for a second then he pushed in a bit more. He'd push and then pause to give her a moment to adjust and then push in some more. It wasn't too long before his entire length was inside of her. Once he was completely sheathed, he grabbed her by her hips and asked, "Are you ready? Because I'm not going to be gentle. I'm going to fuck the hell out of you and have you screaming in minutes."

Destiny actually shivered. Was she ready for this? The answer was, "Absolutely. Do it." He didn't hesitate even a second. The moment she replied he pulled out to the tip and slammed back into her. Hard. Harder than she had ever felt. She cried out a single, "Oh," before he pulled out and slammed back into her again. He didn't even attempt to go slow. He pounded into her fast and hard. In and out, in and out. He'd pull out almost all the way and then smash back in. The fast pace had her close to a climax in no time. After what felt like just a minute, or two Destiny was panting in orgasm. "Oh Yes! Don't Stop! Don't Stop! Ohhhhhh!"

Destiny tried to catch her breath, but it was difficult. Tyler was still behind her pounding away. If she had thought, he might slow down after making her cum she couldn't have been more wrong. Instead of slowing down to let her recover he instead started pounding even harder. And faster. How he was moving that fast was beyond Destiny's comprehension. She didn't think it humanly possible. Being taken from behind was a different feeling completely. He hit spots in her she had never felt before and Destiny was grunting fiercely. Having a condom felt different too. It was slick and slid in and out easily. Unlike with her mystery man, who rode her bare, and she could feel the heat of his member.

Tyler pounded her like a jackhammer. He hit her g-spot repeatedly, his heavy balls slapping her clit each time he pushed in. It was almost more sensation than Destiny could handle. She was overstimulated to the point it was almost painful. And just when Destiny thought she couldn't take it anymore her climax erupted and took over her entire body. She screamed out loud unable to form any words. It was loud and very unladylike. If she had been able to form a coherent thought in her head, she probably would have been worried about others hearing her though the walls. But Destiny couldn't think. She was only able to feel, and she could feel this orgasm in the very tips of her toes to the hairs in her scalp. She didn't know if she would ever come down to earth.

Even though Tyler was still going strong behind her Destinys strength was spent. She collapsed on the bed panting heavily, her head spinning. Tyler pulled out of her, and she felt him moving behind her. He gently grabbed her hips and pulled her ass in the air, higher than it was before. Destiny then felt the tip of his cock begin to prod at her asshole. And suddenly she was out of her sexual daze and wide awake.

"Tyler, please don't. I've never done that before," she said in a panic.

"Shhhhh...It's ok. Just give it a try. If you hate it, I'll stop immediately, I promise. But I think you'll love it."

He continued to toy with his cock and her ass, but he didn't penetrate. He was waiting for her to either give him the go ahead or stop it. Destiny didn't know what to do. This was definitely not something she had planned on nor something she had ever considered. Up until just a few weeks ago her biggest thought had been about losing her virginity. Anal hadn't even been on her radar. But here was an opportunity. Did she want to lose her anal cherry? She could feel the tip of Tyler's member still gently rubbing against her ass. Destiny took a deep breath. She wanted to experience everything. How else would she ever really know herself, what she liked and disliked? She wasn't sure she was ready. But she was going for it, nonetheless.

"Ok. Let's try it," she heard her voice saying. It was quiet and with a slight tremor in it.

"Don't forget to keep breathing," Tyler said, and Destiny could feel him start to push. Destiny could feel her body trying to resist so she took a calming breath and attempted to relax. Destiny was happy for Tyler's length vs. girth. She felt so tight she couldn't imagine taking one that was thicker. Tyler slowly penetrated her, just a little at a time and Destiny focused on her breathing. It wasn't too long, however, before Destiny felt his balls on her ass and she knew he was all the way inside her.

It was a bit odd and slightly uncomfortable but not as bad as what she had feared. Tyler stayed still for several seconds letting her adjust. Then he pulled out a bit before pumping back in. And that's how he went for a bit. He'd pull out a little at a time before pushing back in, each time pulling out a bit further than the last. Soon he had caught a rhythm and before Destiny realized it, he was pulling out to the tip and pushing his entire shaft back in. It wasn't long before Destiny was not just tolerating being anally penetrated but enjoying it. Once her body adjusted to the feeling of his member in her ass it willingly accepted it. She was feeling tingles in nerves she had never felt before and she smiled to herself in satisfaction. "Yes," Destiny thought to herself. "Yes, I want to experience this. I want to know this feeling."