Blind Date

After receiving some great feedback, I went back and re-worked this story with to9ashiyuuta, who was a huge help.

Note: This is a story about unintended cheating. If you don't like stories about cheating wives, you will not enjoy this story. Other than that, I really appreciate receiving feedback!

*******

"No way! Forget about it Sherry. I don't care who he is. Quit trying to set me up." Sarah said, upset that her sister was trying to set her up, yet again. It seemed like every few months, Sherry had another guy who was 'just perfect'.

"Please, Sarah? I promise never to try and set you up again." Sherry pleaded to her sister through her phone. "Look, it would be a huge favor to Scott too. The guy is the son of the CEO at Scott's work."

"Oh! WOW! So, now you're not just trying to hook me up, but now you're trying to sell me off like a hooker?!" Sarah exclaimed.

It did sound pretty bad with her putting it like that. "Oh come on. You know it's not like that." Sherry said lowering her tone.

"Oh? So, what is it like? You figure you'd hook up the boss's kid with your slut sister to get your husband a promotion?" Sarah argued back.

"Really Sarah? You think I would do that to you? Scott was telling me about him. He sounds like a really nice guy." Sherry said.

"Nice guy, huh? So, he's probably really ugly then. Forget it no way." Sarah said.

"Okay fine. I get it. You're upset." Sherry said trying to sound reasonable. "Scott already set it up. It's just dinner at Angelo's. All I'm asking is that you have dinner and pretend to be nice. Then, you never have to see him again and I will never try to set you up again."

"You're right about one thing. You're not going to try this shit again because I'm not going." Sarah said quickly, but before Sherry could reply a distinctive "beep" sounded.

Sherry looked at the phone and saw that the call had ended. "I can't believe you hung up on me!" Sherry tried calling her sister back, but it went straight to voicemail.

Sherry was the older sister by just a year, but a lot of people thought they were twins. The two pretty brunettes loved to fool people in high school. They would even switch jerseys for soccer games, and no one ever caught them except their parents. Once they got into college, they started following different paths. Sarah became a total party girl and ended up dropping out and finishing at a local community college. Sherry, on the other hand, took school seriously and finished her bachelor's degree.

At 31, Sherry was the VP of Marketing for a clothing company. She had met her husband Scott during her senior year in college. They didn't really get serious until the year after they graduated though. Two years later, they got married and decided to hold off on having kids to focus on their careers.

Scott worked for an IT firm and has been stuck in middle management for a few years now and really wanted to make a push to move up. A few weeks earlier, he had heard that the CEO's son, David was coming to town. The word around the office was that the CEO wanted his son to settle down with a wife and kids and eventually take over the company so he could retire.

Scott knew that the CEO was just a bit old-fashioned and would feel better about leaving the company in his son's hands if he was settled down. His mind immediately went to his sister-in-law. Sherry was always on her sister to settle down. She was really pretty, looking almost exactly like Sherry, but could never seem to hold a job or man down for very long. Scott figured that it wouldn't hurt his career to get noticed by the head of the company. As an added bonus, if they hit it off, Sherry would also be thrilled.

A few days later, Scott found himself getting into the elevator at the same time as the CEO. They had been in several meetings over the years so Scott was comfortable talking to him. He mentioned his sister in law and showed him a picture of Sarah and Sherry on his phone.

"My son hates it when I try to meddle in his personal life, but she is quite a pretty lady. He will just have to take my word for it!" The 70 year old CEO told Scott.

The next day, Scott received an email from the CEO setting the date. He immediately called his wife with the good news and she agreed to get her sister to go. Scott immediately replied back letting him know that Sarah was looking forward to it.

By the time Scott got home he was eager to find out how the call went with Sarah. Sherry was in the kitchen getting dinner started. "Hey, honey!" He smiled and gave his wife a kiss on the cheek. "So, how did it go with Sarah?"

"It didn't," Sherry replied bluntly.

Scott stopped in his tracks. His smile started to slip away. "What do you mean? You didn't talk to her yet?"

"Oh, I talked to her. She doesn't want to have to do anything with it."

Scott walked slowly to the small kitchen table and sat heavily. "Fuck." He thought for a few minutes before looking to his wife for answers. "What do we do?"

Sherry stopped working on the Greek salad she was putting together and looked at her husband. "There's nothing to do. She is really pissed off at me right now. You need to cancel the date."

Scott buried his face in his hands. "No, no, no. This can't be happening."

Sherry was back to work on the salad now. She always kept them on a healthy diet. Without looking up, she responded to her sad looking husband, "What can't?"

Scott said miserably, "I already told him that Sarah was really looking forward to meeting his son."

Sherry took a deep breath. She wanted to scream. Why did Scott do such stupid shit sometimes? "Sounds like you've got a problem then," She said sounding cold and blunt. She put the salad into bowls and took one over to Scott. Sitting down next to him, she couldn't help but feel bad. After all, she had been the one to tell him that she would get her sister to do it. The couple sat in silence while picking at their salads. Both of their minds were trying to find a solution. Fifteen minutes later, Sherry got up and took her bowl to the sink while Scott was still picking through his salad.

"Well, the date isn't until Saturday night so maybe we can still find a way to change Sarah's mind. However, you need to do what you can to cancel. Between the two of us, one or the other should happen. Sound like a plan?"

Scott looked up with a glimmer of hope in his eyes. "Thank you so much Honey!" He jumped up like an eager child and started cleaning the kitchen to show his appreciation. "You go sit down. I'll take care of this," he said motioning to the kitchen.

Sherry felt a bit guilty. Her sister was the most stubborn person she knew. She was going to have a tough time convincing Sarah. She filled a glass of wine and went to go soak in a hot bath to relax.

******

All week, Sarah's phone was going straight to voicemail and she hadn't returned any of the messages that Sherry had left her. It was Friday and Scott hadn't canceled the date either. Sherry was mad at Scott for not having the balls to man up, but she also felt partially responsible for thinking that she could make it happen.

Sarah had an apartment that was fairly close to Sherry's office. She decided to drop in during lunch and try one last plea. The apartment complex wasn't anything fancy and it wasn't in the best part of town either. The building was only two stories and the outside reminded her more of a cheap motel rather than an apartment complex. She knocked on the door to Sherry's apartment. Nothing. She knocked again and listened. Still nothing. Worry started to flood Sherry's emotions fearing the worst. She dug into her purse looking for the spare key Sarah had given her.

When a hand touched her shoulder, Sherry jumped. She turned quickly and bumped into the door with a thud. With the door holding her up, she saw an old man that was probably in his 80's standing there.

"Sarah? I'm so sorry!" The old man said backing away with his hands up. It was clear he thought she was her sister. She was about to correct him when he continued, "I thought you were going to be gone until next weekend?"

She wasn't sure why she said what she did next, but she stood up feeling much more relaxed. She replied, "Oh, I just forgot some things."

"You have a fancy interview or something? You sure look nice." The old man said still standing there as Sherry dug out her keys.

"Maybe, we'll see," Sherry said not sure what else to say as she opened the door.

"Well, okay then, do you still want me to pick up your mail?" He asked kindly.

"Um, yes. Thank you." Sherry closed the door slowly trying not to be rude.

As usual, Sarah's apartment was a mess. Clothes were all over the living room and dishes sat out on the counter. "Come on Sarah, get it together," she said as if her sister was there. It wasn't as if she hadn't said those words to her sister a hundred times, though. She continued to look around to see if she could figure out where her sister ran off to. Eventually, she made her way into Sarah's bedroom. Like the rest of the place, it was a mess. Not at the level of a hoarder or anything, but the woman needed to learn to pick up after herself.

Fighting the urge to pick up Sarah's place, she looked into the open closet. While Sherry would never admit it to Sarah, she did envy the way her sister could let go and have fun sometimes. She flipped through some of the party dresses that were hung up. All of them were tight fitting, while some had no shoulders or no back. All of them looked quite sexy though and each one showed off some level of cleavage.

Sarah had never been one to shy away from showing off her body. She had always been really good at taking advantage of men. Sherry on the other hand always felt uncomfortable showing off. She pulled out a black dress and held it in front of the mirror. It was a sleeveless V-neck that looked too small for her or her sister. Sherry laid the dress on her sisters unmade bed and began to undress feeling adventurous. She wanted to see how it would look on her. Sherry was strict about working out hard and eating right.

The closet door was made of two big sliding doors with mirrors covering them. Sherry watched her 5' 4" frame step into the dress with only her black panties and matching bra on. The dress stretched as it was pulled over her shapely thighs. She smiled at her tight abs as the dress shrank to snugly cover her tiny waist. She started to slip her arms under the shoulder straps and pull it up over her 34C bra, but it was clear that the dress was not made to be worn with one. She quickly reached around, unsnapped her bra, letting it fall to the floor and freed her breasts. They were full, round and smooth. It wasn't often that she went braless. It felt a little strange, but at the same time naughty and liberating. She slid the dress back off her shoulders and admired herself in the big mirror.

Sherry did still look like her sister. She imagined herself out at a nightclub dancing and having fun. The neckline went all the way down her chest and in between her breasts showing a generous amount of cleavage. She felt sexy and thought about borrowing the dress to surprise Scott when suddenly her cell phone started ringing. "Speak of the devil," she said out loud before answering, "Hey Honey."

Scott replied in a panic, "Have you talked to Sarah?"

"I'm at her place now actually."

"Oh, thank God!" He blurted in relief.

Sherry realized what he must have been thinking and tried to reply, "But."

Only Scott had cut her off, "What a relief! Mr. Bruce just came by my office and went on and on about his son and how he hoped they would hit it off!" He suddenly realized that his wife had started to say something. "I'm sorry, Babe. What were you going to say?"

"I.," she paused instantly feeling bad for Scott. She looked at herself in the mirror and saw Sarah looking back at her. "Sarah will be there." a knot formed in her stomach as she said it and her voice felt shaky.

"What's wrong then?" He asked sensing hesitation.

Sherry's mind scrambled. She couldn't very well be in two places at once. "I have to go out of town this weekend for work." It happened occasionally so it might work. She didn't know what else to do.

"What? again? They can't keep doing this to you without any warning!" Scott replied frustrated.

"I do what I have to do," Sherry replied honestly.

********

That night after work, Sherry packed like when she normally goes out of town for work. Instead of driving to the airport in the morning, she went to her sister's place. She wasn't due to meet this guy until 8 pm so she had a lot of time on her hands. She went and had her nails done and treated herself to a massage to loosen herself up.

Sherry told herself that she would go as Sarah, be nice to him. When it was clear that they didn't have any chemistry they would part their separate ways at the end of the night. No harm, no foul. Right? What could go wrong? It would be just like when they were kids. Only this time, it would help Scott.

Sherry got dressed into the sexy black dress she tried on the day before. She styled her dark hair so that it looked like her sisters. It was straight, hanging just past her shoulders. Sarah wore a little more makeup than Sherry was used to, but she wanted to play the part the best she could. She couldn't remember the last time she switched roles with sister. It made her feel naughty and at the same time nervous. Sarah always had a good supply of alcohol on hand so she treated herself to a scotch so she could relax a bit.

By the time Sherry called a cab to pick her up, she was feeling relaxed and arrived at the restaurant a few minutes early. There was a reservation set at the fancy Italian restaurant, which is how they were to find each other. Sherry ordered another drink feeling the nerves starting to creep back. She downed it quickly.

She was starting to have second thoughts. "I can't do this!" She said under her breath. She was just about to stand up when a tall handsome man approached her, grabbing her attention.

"You must be Sarah," the man said with a charming smile and offered his hand out. He was easily over six feet tall and had broad shoulders. He was clean cut, yet ruggedly handsome. She thought of James Bond. He wore an expensive gray suit with no tie. The collar of his white dress shirt was open.

"I uh, yes. Nice to meet you." She felt like an idiot jumbling her words. She stood up to greet him and felt light headed. Sherry tried her best to not let it show and reached for his hand to shake. Instead of shaking it, he held it gently and kissed the back of her hand in a very old fashioned gentleman-like way. Sherry wasn't sure if it was due to the alcohol, but she was impressed.

"I'm David and it's a pleasure to meet you." As he stood back up his eyes followed her body from her feet to head. Sherry could almost feel him taking her in. "You look amazing," David said moving to take his seat. Normally such an expression would make him a creep, but David made it feel somehow like a compliment.

Sherry could feel herself blush. "Thank you," she replied feeling like a schoolgirl all over again. David ordered a bottle of expensive wine while they got to know each other. She was surprised, yet a little jealous of her sister the more she talked to David. He was focused on what interested her and quickly made Sherry feel at ease. More than a few times, Sherry had to remind herself that she was pretending to be Sarah. Her answers at first were based on how she thought her sister would answer, but David made her feel so comfortable that she wasn't quite sure who she was talking about. Before she knew it, Sherry lost total track of time enjoying herself. Not to mention another bottle of wine had her feeling even better.

David stood up and offered his hand out. "Well? Come on. It'll be fun."

Sherry missed what he said completely. Unsure what else to do and feeling comfortable with David, she decided to go along with it and let him take her hand. He led her to an outdoor patio with a live band, bar, and dance floor. They walked out to the dance floor and David took the lead. He placed one of his large hands on the small of her back and took one of her hands with the other. Sherry felt like she was floating in a dream.

"To be honest, I wasn't sure what to expect tonight." David said quietly so that others couldn't hear, but that Sherry could. "You're way more beautiful than I could've imagined."

A voice in the back of her head called out to Sherry. To stop. To leave right then. Sherry looked up at the handsome man and smiled. She was having a great time and was confident that it wouldn't lead to anything. They would say goodnight shortly and that would be it. She had nowhere to be, so why not enjoy the night?

They took a break for another round of drinks before heading back to dance some more. "Scott never wants to dance and David doesn't want to stop!" Sherry thought to herself as they headed back. The music had picked up now. She wasn't even sure when that happened. She moved her body to the music. It reminded her of salsa music. The dress clung tightly to her body, but with no bra she could feel her breasts bouncing under the thin fabric. This made her nipples harden immediately and induced goosebumps all over her body. It all felt so amazing and erotic; almost like a dream.

Suddenly David's large hands were around her small waist as he came up from behind her. Sherry pushed back against him feeling his warm body. He lifted her arms up and placed her hands around his neck. He had to bend down slightly so she could reach. He left her hands at his neck and trailed his fingertips down her wrists then her arms. His hands were amazingly soft yet firm. The hands moved gracefully down her sides until they reached around to her stomach and pulled her even closer. It was amazingly erotic and Sherry's hormones were going crazy. She was thinking she might have to go straight home tonight and fuck Scott's brains out.

Sherry imagined herself running into the house and sticking her tongue down Scott's throat. Grabbing his head, running her hands through his hair as she pulled herself closer as if trying to reach deeper into his mouth. She could almost taste him.

"Wait a second. How did we get here?" Sherry realized that she was in a cab with David. He was kissing her neck and working his way back to Sherry's lips. "I can't" is what she meant to say before David filled her mouth with his tongue." Her body felt like it was on fire and it just needed to explode. Was she dreaming or just that drunk?

The small voice in her head called out to her, "It's almost over. Just say goodbye when the cab drops you off. You can still stop."

"Yes. That's right. I will just say goodbye when the cab drops me off." She repeated in her mind.

"David's hands are so big and strong, though," another voice argued. She loved how they roamed her body, so firm and strong. Electricity surged through her body as he grabbed her tits through the dress. Her nipples were more sensitive than she could ever remember. She felt the cool night air over one of her perky breasts, waking her from her dream state. They were outside now. All she could think about was opening the door. It was like time jumped, but before Sherry's thoughts could come back to Earth, David's hand pulled gently on the breast that had been released from the dress and played gently with the nipple. Shivers went straight between her legs.

With one tit hanging out of the dress and David wrapping her up with his arms from behind, they stumbled into the apartment when she finally got the door open. David turned Sherry around to face him and quickly pulled the top of her dress down, over her shoulders up to her waist; freeing both of her beautiful rack. Sherry frantically worked at opening his shirt and pulled it back off his wide shoulders. She rubbed her hands over his strong chest.