Karena Simmons knew that as Office Manager, she’d had every right to make the decision to hire a new Office Whore for Chad and take on his current one, Reina, as her new assistant. She also knew that Chad had agreed to all of that during a moment of utter confusion over how to handle his feelings for her. Feelings that Chad didn’t even realize he had, Karena thought. She had never meddled in his love life before now. But then, she had never seen him so completely out of his element over a woman before now. So, when he called her office to try to discuss Reina, she lied and said she had a meeting and she couldn’t talk right now. Perhaps later?

Chad Stephens had been her boss and her best friend for the past 10 years. During that time, she had seen him be successful in business, generous in his community, and miserable in his love/sex life. It was puzzling, to most people, that he didn’t have someone in his life. He was impossibly handsome, with dark brown hair and eyes to match. He had a well-toned body with a nice-looking ass (even though she was a lesbian, she could still admire a guy’s ass). Plus, his voice could make a woman’s panties slide right off of her. So why didn’t some amazing female swoop in and snatch him up?

Karena knew the answer to that question. He knew how to fuck women; he just didn’t know how to love them. Chad lacked the ability to express his feelings to a woman. She’d known that from the start. She actually slept with him for three months, before she admitted that she preferred women in her bed, because she cared about him so much. She knew his heart was fragile. She thought she could help him figure out how to feel, but in the end, he stayed emotionally stagnant and they ended that relationship somehow as best friends.

She’d watched him as he closed himself off every time a woman came even close to scratching the surface of his emotions. So, as much as she knew that she could have Reina to herself, not just as her assistant but as her bedmate, she also knew that it would crush Chad and likely end their friendship.

She’d listened to Reina cry yesterday and realized that it was the poor girl’s heart that was aching. Yes, she was visibly shaken by rough anal sex with Chad, but it was clear that her feelings hurt more than her ass.

So Karena did what any good friend would do, she set things up to force both of their hands. She knew that Chad wasn’t ready to give up Reina; now he only had three days to figure that out. She also knew that, while Reina might be extremely angry and hurt, she wanted very much to be more than just his Office Whore.

The few times that Chad did wander out of his office for the remainder of the day, he looked like a lost puppy. Savannah, the girl that Karena had hired to be the new Office Whore, was so apparently so dense that she didn’t even seem to notice his misery. She tried striking up conversations with him, but he ignored her efforts. Karena knew that as hard as it was to see him so unhappy, this was the only way to push him into realizing he wanted Reina just as much as she wanted him.

The next morning, Reina had mixed feelings when she arrived at work. On one hand, she was excited to receive a promotion to Karena’s assistant and she would be learning a lot more about the company and business in general. On the other hand, however, it hurt to see a tall, slender blonde occupying her old desk already. She knew that meant her chances with Chad were over. She’d live somehow, she told herself.

Chad arrived at work a few minutes late. He had hoped Reina would be in Karena’s office when he got there so he could slip by her. However, as he walked past Karena’s door, he bumped right into Reina, practically knocking her over.

“Oh my gosh, Reina, I’m so sorry. Are you ok?” Chad asked penitently. He touched her arm gently, “I didn’t mean to hurt you. I would never do so on purpose.”

They both knew he wasn’t apologizing for just bumping into her now. He looked a little sleep deprived, Reina thought, but so was she. She wanted to be angry at him still, but he looked so remorseful, she didn’t have it in her heart to be cross with him. She simply gave him a strained smile and said, “It’s ok, really, I’m fine.”

The uncomfortable silence that followed made both of them feel awkward. It was Reina who broke that silence by saying, “Thanks for agreeing to my transfer to be Karena’s assistant. I’m sure that Savannah will do great in my old position. She seems very nice.” Then she turned and walked away, leaving Chad feeling abandoned.

He walked quietly back to his office, giving Savannah only a nod when she said good morning. Once he was sitting at his desk, he turned on his computer and couldn’t resist opening the video of him and Reina from last Friday. He put it on half speed and watched himself make love to her in slow motion. Then he forced himself to watch yesterday’s video all the way through this time and winced while he saw himself take her ass roughly. The first hard thrust had been an accident. But that didn’t excuse the plethora of thrusts that came after. Then he saw what he didn’t see at the time, tears streaming quietly down her face because she didn’t want to disappoint him by using her safe word to make him stop.

It was difficult to reconcile the fact that he had that been so oblivious and inconsiderate; that the same man who had, according to Karena, made Reina see God in the shower had been the devil himself as he had pumped his cock into her like a rutting bull.

He had three day to make things right. Shouldn’t be too difficult, right? He wanted to ask Karena for advice, but she seemed hell-bent on avoiding him right now.

Chad looked at the list of tasks he hadn’t requested yet from Reina and decided to pick one and call her into his office. If they couldn’t talk to each other, at least their bodies could.

When Reina’s phone rang, she answered tentatively, “Yes, Chad, what can I do for you?”

“Reina, I need you to come to my office please; Task 6,” he said calmly.

“But I…” Reina started to object, when Chad cut her short.

“Reina, the agreement I made with Karena was that I could still call you in to my office until Savannah is ready,” he said, his voice a little shaky.

“Yes, of course,” she replied, unsure of just which Chad she would encounter today. But as he was still her boss, she prepared to go to his office and let him slip his cock between her full, round tits.

As she walked past Savannah, Reina smiled and said hello and chuckled a little to herself. Good luck doing a Task 6 with those tiny breasts, she thought to herself. Then she chided herself internally for being so catty. She was just jealous, she realized. Not of Savannah herself, but of the fact that soon she’d be taking Reina’s place on Chad’s couch.

When she walked into his office, Chad noticed that she had a dress on today and would, therefore, need to be naked for this Task 6 session. It made his cock hard to watch her undress. As she drew the dress up past her hips, he saw she was wearing panties. He was about to reprimand her, but stopped himself when he realized that she’d probably worn them to spite him. Let her be angry, he thought, she certainly had every right to be. So instead, he simply asked, “Take off your panties, please.”

With a look of defiance in her eyes, she removed her panties, knowing full well that Task 6 didn’t require her nudity from the waist down. But she wanted him to touch her so desperately, so she said nothing. Soon she stood completely naked in front of Chad and he had this overwhelming urge to kiss her.

Managing to resist temptation, he undressed completely as well. He walked around the desk and took her hand, leading her to the couch. He sat them both down together and couldn’t hold back anymore. He took her face into his hands and kissed her lips so softly at first, she sighed. He sensed her relaxing and kissed her again, this time a deep, passionate kiss that made her eyes flutter and close. He moved to her neck and shoulders; giving soft, wet, sensual kisses as he trailed down to her exquisite breasts.

He slipped a finger inside her hot, wet pussy and watched her eyes fly open wide. Before she could speak, he said, “Try to remember that I’m your boss, and I can improvise if I so choose.” He hadn’t meant to sound so formal, but when she spread her legs apart a bit more to accommodate his hand, he decided not to second-guess himself.

And that was the real problem here wasn’t it? Constantly second-guessing himself, always afraid to make the wrong move. Just this once, he implored whatever divine power there might be, please let him just go with his gut.

He continued to slide one finger, then two, then three, inside her hot needy cunt. She was meeting his thrusts and practically purring. God, that was so hot! He wanted her everywhere.

He laid her back gently on the couch and took his drenched hand and wiped it on the space between her gorgeous tits. Then he leaned down, careful not to slip this time, and rubbed his cock on her chest.

“Press those beautiful girls together for me, baby,” Chad said with that sexy voice of his. “I want them around me so I feel like I am fucking your tight pussy.”

Reina obliged him willingly. The feeling of his hard shaft sliding between her tits was so erotic. She forgot the “no extra commentary” rule and said, “Oh my God, this is so incredibly hot! I’ve never done this before!”

Chad just smiled. He found it such a turn on that she spoke freely like that. Some of his rules were dumb.

He stroked himself there for a bit longer before stopping and saying, “I want to make you feel good Reina, I want to make you cum so hard. Go over to the filing cabinet on the far right and reach into the toy box. I want you to choose something for me to put in your pussy. Choose something you think will really turn you on.”

This was Task 10, Reina thought, although the rules had him selecting the toy or toys. He didn’t seem to be following script, so she veered off as well. “May I also choose something to put in my ass? Something that will help get me used to having my ass filled?” Something that was part of Task 11.

Chad’s cock twitched. He’d been afraid to even think of touching her ass again, and here she was offering to let him put a toy inside it. That she would show her forgiveness in such an intimate way poked at his heart, more than a little.

“On one condition, my sweet slut,” Chad made sure they had eye contact as he spoke tenderly to her, “I want this to be pleasurable for you, Reina. You MUST use your safe word if I hurt you. Do you understand?”

Reina nodded and said, “Yes I understand.” Then she went to the toy box and chose a vibrating dildo for her pussy and a slender butt plug for her ass. It was still a little sore from yesterday, but with enough lube, the size of this toy should be alright, she thought.

She returned to the couch and Chad wrapped his arms around her, kissing her like a lover. Reina’s heart hurt just a bit, knowing that this was just sex for Chad, but grateful that she would have a few more days to enjoy him before Savannah would be sitting here in her place.

“Tell me which toy you want inside you first, baby,” he murmured.

“I want the dildo in my pussy first please,” she moaned.

So, he took the dildo and, lubing it up first, slipped it into her slowly. Her body arched and she moaned with pleasure. Chad turned it on the lowest setting to start. Then he took a generous dab of lube and worked her tight little asshole gently with his middle finger until he felt her relax again. He lubed up the butt plug as well, and slid it inside her as if moving in slow motion. He didn’t want to hurt her again. He watched her face for clues of how this was all feeling.

She grimaced a bit when the anal toy first entered her, but then she smiled once it was completely inside her. Chad turned the vibrator in her pussy up to the next speed and started slowly fucking her with it. She moved her body to meet his rhythm and, when he took a wet finger and circled her clit, she climaxed almost instantly.

Chad smiled as she squirted her juices all over his hand. He bent down to lick them off and then moved his tongue to her clit. His sucking and nibbling sent Reina right over the edge with another orgasm before the previous one had finished subsiding.

“God, you’re amazing,” Chad said, realizing he had said the words out loud. He was embarrassed until heard Reina answer.

“So are you, baby,” she said in a dreamy voice. “Mm, do that again, please?” she added sounding a little drunk.

So, he licked and he sucked and he moved the toys in and out of both holes, and felt a sense of redemption when she came hard again and again.

Slowly removing the toys, he said, “I need to have you. I want to fuck you in the shower again. Please baby, I need to make love to you again.”

He guided her to the shower and turned on the water, taking her playfully into his arms while he kissed her and touched every part of her body. He took turns sucking first on the right nipple, then the left, while his fingers played with her hot, needy pussy. He pushed her back against the wall and went down on her, licking and sucking while his fingers worked inside her. She screamed out his name as she exploded in his mouth.

God, he needed to be inside her! So, he picked her up, gently pushed his cock into her amazing pussy, and fucked her like a lover until they both climaxed and slid to the floor again; the hot water beating down on them as they both giggled a little.

“We have to stop meeting like this,” Reina teased. She laid her head on his chest and listened to his heart beat like the drum in a heavy metal band. When he went to say something, she put a finger across his lips, saying, “No don’t, don’t spoil this moment. Let me just have this short while to pretend that I’m yours and that you’re mine.”

Chad tensed up subconsciously. He could feel himself falling for her almost quite literally; he wanted, more than anything to tell her that he was pretty certain he was in love with her. But his heart couldn’t handle it if she rejected him.

“Reina,” Chad said softly, “You’re an amazing lover and I find myself wanting you again and again. But this isn’t a fairy tale and I’m not Prince Charming. There is no happily ever after, where we get married and ride off into the sunset. Life, my life anyway, just doesn’t work that way.”

So many emotions swirled around in Reina’s head and in her heart. She wanted to argue with him and tell him it didn’t matter if he loved her or not, that they would make it work. But it did matter, and she wanted the fairy tale and the happily ever after.

“I understand, Chad,” Reina finally said softly. “I’ll just grab a towel and dry off and dress quickly to get out of your way ok? Thanks for calling me in and giving me something amazing to remember.”

“We still have two more days, Reina,” Chad said, almost pleadingly.

“Yes, of course, Chad, two more days,” she said as she zipped up her dress and felt her heart break a little more, knowing those days would come and go far too quickly for her.