“Well, it looks like it’s going to be a long flight. Why don’t you tell me a little about yourself? I don’t think I’ve been able to sit down and get to know you, and this is a perfect time!” Michael said.
Now that they were in the air, people were settling into the groove of the flight, and the noise level was perfect for a quiet, intimate conversation. Iris turned her head to her boss and smiled.
“Sure! What would you like to know?” she asked, tossing her head slightly so her blond hair was out of her face. She smiled eagerly, excited for a chance to get to know the stranger that supervised her.
Michael reached up to adjust his tie, but after realizing that he had opted for a more casual outfit today instead of his usual suit he simply smoothed his collar and placed his hands in his lap. The tie adjusting was a reflexive habit, a gesture seen as professional when his anxiety made him fidget during meetings. He didn’t consciously realize that this habit also drew people’s eyes, breaking their eye contact so he wouldn’t feel intimidated when starting a conversation.
He had selected Iris for this trip because she was the most attractive girl in the office, partially out of spite as he had received his ex-wife’s wedding invitation that same day. He didn’t want to be seen as a creep, but he was genuinely interested in her, and the fact that he had gotten away with using his position to get closer to someone made him nervous.
“Tell me about your family. Do you have siblings? Kids? I honestly don’t even know if you’re married,” Michael replied, his normally commanding and firm voice in the office now gentler and friendlier than Iris had ever remembered hearing.
“Not married, no kids, but I would like to try for one someday. I have an older brother that lives in Alberta, Trent. He’s an independent contractor and loves working with his hands. Otherwise, it’s just me and my roommate Cait.” Iris smiled, and Michael couldn’t help but stare.
Her face was the definition of perfect, and the light makeup she wore complimented her naturally striking features perfectly.
“What about your parents?” Michael asked, turning slightly in his seat so he could look at her better.
“They’re about a twenty-minute drive from my place. Close enough to visit for every little holiday,” she laughed. “What about you?”
“My family isn’t exactly typical. I have an older half-sister and three younger half-siblings, but I’ve only met Rebecca, the oldest. My parents are divorced and my mom lives close by. My dad and I don’t really get along. But otherwise no kids, no partners. I’m pretty close to one of my uncles, but that’s about it.”
“Ah, I see,” Iris replied, then went silent. Michael had never talked to her one-on-one before, only with the rest of the office at regular meetings, but she found he was an attractive conversationalist. She paused, trying to think of how to continue the conversation.
“I like your dress,” Michael said politely, also sensing Iris’s hesitancy.
“Thank you! This is one of my favorites, but it’s too short for work.” Iris played with her skirt a little as they talked, running her fingers down the pleats in the dark-blue fabric.
“No, it isn’t. That looks professional enough for work. It follows dress code,” Michael stated matter-of-factly.
“It really isn’t. Karen in HR yelled at me because it was too short.” Iris rolled her eyes. “It doesn’t matter that much.”
“But it does,” said Michael. “You’re an adult, and you should be allowed to wear what you want. It’s completely acceptable by any reasonable standards. Since when has this dress code thing been in place?”
“Since I started.“
“Well, I’ll have to change that. It’s a little sexist. I’ve never had anyone say my clothes were inappropriate, and you shouldn’t either. You doubled your quarterly goals for sales! Who cares what you wear when you do it?” Michael seemed frustrated on her behalf and determined to fix the problem, and Iris was taken aback at how this minor issue for her seemed to be such a big deal to him.
“I appreciate that. And I’m so grateful I was the one that got to come with you on this trip! Hawaii is so beautiful this time of year. I can’t wait to swim on the beach,” she said, excitement overpowering her normal soft and quiet demeanor.
Michael laughed, clearly enjoying how excited she was for the most irritating business trip of the year and grateful for the change in conversation.
“I’ll bet the beach suits you,” he said. Michael stole a glance at her long, smooth legs and wondered what it would be like to feel them.
“Oh, I was made for it. I have the cutest black polka dot bikini, and I swear it looks like it was from a modeling catalog. I haven’t had any chance to show it off.”
“Wonderful! I’d love to see it. Your outfits suit you well. You might even be able to convince me to get in the water too,” he laughed.
Iris and Michael continued their lighthearted conversation for the rest of the flight. Within a few hours, it was clear to both of them that they were well-suited for each other, and not just in a professional sense. They got along well as friends, and just talking about mundane life was so incredibly easy that the flight was over before they noticed it. Michael was obviously attracted to her, and Iris noticed her thoughts started sliding in a more erotic direction the longer they were together. When the announcement was made that they could retrieve their overhead bags, it took both of them by surprise.
“Wow, that felt a lot shorter than it was,” said Iris. She stood up in the small space as Michael also started to get up, trying to navigate the best way to retrieve their things and get off the plane without being in anyone’s way.
“I can get my bag!” said Iris as Michael made a move to get it for her. She was a foot shorter than him and had to stretch to grab it, and as soon as she had it in her arms she started to fall over. Michael immediately put his hands on her arms to help her, and for a moment during the shuffle of luggage, she could feel his body-hugging her. Iris felt a shiver go through her, unexpectedly enjoying the brief moment of contact between them. When they pulled apart, she couldn’t help but wish it had been longer.
“Excuse me, I didn’t mean to do that,” Michael said as they separated, a flush of red on his cheeks.
“Not a problem!” Iris replied in a bubbly voice. She could tell he was still uncomfortable, so as they stepped off the plane and walked through the airport she directed the conversation elsewhere. “Does the shuttle take us directly to the convention center?”
“It doesn’t. We’ll go to the hotel for the rest of the day, and the conference starts early tomorrow morning.”
“Wait, we have the entire day to ourselves?” Iris said in surprise. It was still early afternoon, and the weather was perfect for swimming.
“Yeah, the later flight would have had us landing at midnight, and I wanted to make sure you had enough time to adjust. Long flights affect people differently. Last year, I took Jared before he moved into accounting, and he was late to the first session because he overslept. I felt responsible for that.”
The pair had reached the shuttle with their bags and handed them to the driver, who wordlessly loaded them into the back. Michael slid into one of the shuttle seats, Iris following close behind. After several moments, it was clear they were the only two people on the trip to the hotel, and that made Michael relax significantly more. Iris took the opportunity to slide in closer to him, their legs touching despite having plenty of room to stretch out.
“What is the room situation?” she asked politely, leaning into him slightly on the seat.
“Oh, there are two separate bedrooms connected by a door. We’ll have to share a bathroom, but you’ll have plenty of space to stretch out. Your window faces the beach.”
“How nice! I appreciate the privacy, too, but I wouldn’t have minded if we needed to share a bed.” Something changed in Iris’s eyes, her everyday look of quiet interest overcome with a seductive, tempting one.
Michael was surprised, but as soon as she turned to look out the window he could feel his pants start bulging. Maybe she had suspected his game all along.
The rest of the ride and the following luggage shuffles and check-in processes were uneventful, but as soon as Iris was able to look around she forgot everything that was happening. On a walk Michael had taken dozens of times up through the hotel’s winding hallways, Iris stared at her surroundings open-mouthed. The open-air, spacious design was unlike anything she had ever seen before, and with the blue sea and the lush, green island in the background of her tour it felt like something out of a fantastical dream. She eagerly rushed into the room and ran to the window that faced the beach.
“Oh my god, look! It’s perfect! We should go swimming!” she said excitedly. Michael laughed to himself and smiled.
“I don’t think I’m persuaded that I want to go. Why don’t you show me that bikini you were all excited about?” Michael said from the doorway.
Iris immediately closed the doors that connected their rooms and began changing. Michael set his things down, locked the door, and took a seat at the edge of the bed.
“Ready?” she asked from behind the closed doors.
“Sure,” he replied.
Michael’s jaw dropped. The bikini was black with white polka dots, but he was fixated on how incredibly hot she looked. She had curves unlike anything he’d dreamed of, and he was struggling to control himself as he stared at her.
“I assume that means you like it?” she laughed.
“Can I get a closer look at it?” he asked.
Iris climbed onto his lap and straddled him, putting his face directly into her soft breasts. “This close enough?” she said in a low, seductive tone. Michael didn’t notice what his hands were doing until he had half untied her top and put his hands under it, feeling her as she leaned down to kiss him.
With a speed that probably could have broken records, Michael undressed as Iris pulled off the rest of her clothes. His cock was rock hard and dripping from the tip. Iris grabbed it as she bounced slightly on his lap, running her hand up and down his shaft.
“I want to sit on it,” she whispered in his ear as a slight moan escaped his lips.
Iris slid his dick inside her soaking wet pussy, letting out a moan as her body adjusted to Michael’s massive cock. Slowly at first and gradually speeding up, Iris rode his cock like she was inside his head and knew exactly what he wanted her to do. Michael’s hands ran up and down her body, then grabbed her waist and slammed himself into her harder.
Iris moaned sharply, and Michael could feel her starting to tense. He used his hands to guide her up and down until he felt a small burst of liquid.
“Did you just cum?” he asked, maintaining the speed as she started to slow down.
“Yes,” she said breathlessly, struggling to keep up with him.
“Good girl,” he said, and grabbed her waist so he could hold her up and fuck her. He slammed his hips into hers over and over as she moaned harder.
“Fuck, that feels so good,” she said, her eyes dazed. “You’re so fucking big.”
Michael fucked her for what only felt like a few seconds before he tensed and started cumming, exhaling slowly as he filled her. They both sat in silence for a few minutes.
“So we’re going to the beach?” Iris laughed. Her boss smiled.
“Yeah, sure, I guess so.”