Blind Date
written by:
DJ

"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 to never try to set you up again." Sherry said pleading to her sister through her smartphone. "Look, it would be a huge favor to Scott too. It's the CEO's son of the company he works for."

"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?!"

It did sound pretty bad 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 said sounding even more angry.

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

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

"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 ask 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. She 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, but they didn't really get serious until the year after they graduated. Two years later, they got married but 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. He had heard that the CEO's son was coming to town and was also single. The word 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's mind immediately went to his sister-in-law. Sherry was always on her sister to settle down. She was really pretty, but could never seem to hold a job or man down for very long. Maybe this was his ticket!

When 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, "When I talked to Mr. Bruce today, I 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. 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. "You go sit down. I'll take care of this." 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.

******

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

Sarah had an apartment that was fairly close to Sherry's office so 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. Sherry felt uneasy about her sister living there. 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.

Sherry jumped when a hand touched her shoulder. She turned quickly and fell onto 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. Then, 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 her 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. She made her way into Sarah's bedroom and 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 tight fitting, some no shoulders, others no back and all showed off cleavage. 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. Sherry worked out hard and ate right. She knew she had to look better than her sister even though Sarah still looked amazing even without working as hard for it.

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 panties and 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 and unsnapped her bra and let it fall to the floor freeing her breasts. They had just the slightest hang to them giving a teardrop-like shape to them with her pink nipples pointing straight out. It wasn't often she went braless. It felt a little naughty and freeing. She slid the dress back on 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 so sexy and thought about borrowing the dress and surprising 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 much this meant to him." 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 in the black dress. "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 she was leaving as she does when this normally happens, but 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, she would go as Sarah, be nice to him but show that they didn't have any chemistry and 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's career.

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 and down 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 a 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 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 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 and a bit jealous of her sister the more she talked to David. More than a few times, Sherry had to remind herself that she was pretending to be Sarah. She 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 will 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 are more beautiful than I could have 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. It wouldn't lead to anything anyway. 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 tits bouncing under the thin fabric. The feeling of her nipples rubbing made them hard and she could feel goosebumps all over her body. It all felt so amazing and erotic.

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. Time seemed to be jumping around. Was she dreaming or just that drunk?

The small voice in her head called out to her, "It 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. The way they felt grabbing her tits through the dress was amazing. 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 this damn 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 small dress and David wrapping her up with his arms from behind, they nearly fell into the apartment when she finally got the door open. David turned Sherry around to face him and he quickly pulled the top of the dress down over her shoulders to her waist freeing both of her beautiful tits. Sherry frantically worked at opening the dress shirt and pulled it back off his wide shoulders. She rubbed her hands over his strong chest.

The voice tried calling out the Sherry again. This time even quieter than before, "Wait. Stop!"

It was too late. Sherry was rubbing a large bulge through the expensive slacks. She reached for his belt and opened it. Then, the clip holding the waist of his slacks was free and his slacks dropped. Sherry wasn't watching to see where his pants went. Her hands went immediately to pulling down the silk boxes. David's big dick sprang free already hard and pointed straight at Sherry's stomach. Her hands went straight for it and began rubbing it with both of her hands. She had only seen a cock like this in porn!

Meanwhile, David was attacking Sherry's neck and ears with wet kisses. Just as his cock was freed, he pulled the bottom of Sherry's dress up to her waist leaving the entire dress as one small piece of fabric wrapped around her waist. One of David's hands went to Sherry's pussy and began rubbing it through the thin g-strings that were covering it. They backed up to a small table that was in Sarah's dining area and David picked Sherry up and put her on the table while she never let his cock go.

With her animal instincts having fully taken over now, Sherry pulled him by his cock closer to her. She wanted to feel his cock inside her. David started to try to slide her panties off, but she was sitting on the table. Not wanting to take the extra three seconds to let her lift up, he swiftly yanked down. With a brief tearing noise, the crotch was now hanging open.

Sherry wasted no time pulling his cock to the entrance of her pussy. Her pussy was already sopping wet and she slid the mushroom shaped head in. She looked down to see her pussy lips spread to accommodate his girth. Her entire body shuddered as his cock slipped deeper and deeper. Sherry pushed off some stuff that had been on the table to the floor and laid back. She wrapped her strong legs around David's waist pulling him deeper. She had never been filled like this before and it was amazing.

David began with long slow strokes, pumping his cock in and out of Sherry. Sherry used her legs to pull him tight with each pump. Their pace quickened and Sherry squirmed on the table. Her breasts shook with the small table. David took one in each hand and Sherry put her hands over his. The table was squeaking loudly now as their bodies slapped together. Sherry's entire body shuddered into an orgasm like she has never experienced and fell slack onto the table to catch her breath. The table was not big at all. Sherry's head hung over one side while her legs hung over the other side. She felt the big cock slide out of her pussy making her feel empty and groaned in disappointment. Her head was still spinning and Sherry was trying to gather her bearings when she felt something wet on her lips. She opened her eyes only to see the biggest dick she had ever seen poking at her mouth.

Sherry was no prude, but she rarely gave her husband a blowjob and once to a guy she dated when she was still in school. It had never been a good experience and looking at the size of this thing in front of her, she knew that this wasn't going to work. Sherry opened her mouth to say, so but David stuffed his cock inside too quickly. She only had a bit more than the head in her mouth when she heard David's smooth voice, "That's right. Just relax. Let it slide in." He pushed deeper in and Sherry started to gag, but David had already pulled back. "That's okay. let's try again. You got this." He slid his dick back and forth easily and smoothly. She could feel it sliding into her throat. She couldn't believe it! Sherry realized she was also tasting her own salty cum that was still on his dick. Normally this would gross her out, but for some reason it was really hot right this minute.

David pulled his dick from Sherry's mouth and scooped her up into his arms taking them into the bedroom. He dropped her onto the mattress and climbed over her. His cock rubbed at her lips and Sherry reached down to direct it back in. Despite it only being a few minutes since it had last penetrated her, it was already stretching her again. He leaned down and began kissing her breasts as he pumped himself harder and harder. Sherry couldn't believe his stamina. She could feel another orgasm building and bucked her hips in rhythm. David turned Sherry's hips to the side and changed his rhythm to a smooth rocking motion. Sherry could feel this amazing cock rub her in new ways, the tension of the orgasm built even higher. It was an entirely new feeling so Sherry didn't want it to end yet. She clenched her pussy down trying to hold on. David moaned in pleasure from the tight pussy gripping his dick. It was too much to take and Sherry's entire body shook and shuddered like a violent earthquake. Her pussy began gushing juices. "I don't think I have ever gushed before!" she thinks briefly. David continued pumping through it all and their bodies were now making a wet slapping sound like a wet towel slapping the floor over and over. Pumping harder and harder the headboard starts smacking the wall. David thrusts as deep as he can. His cock pulses and Sherry feels her pussy being filled up. The feeling of his big dick pulsing and filling up is enough to send Sherry into another climax. David pulls out with what feels like a gallon of cum draining out of her pussy. The sweaty couple collapse on the bed together in total exhaustion.

*******

Sherry wakes up with her head on David's chest. The reality of the situation hits her like a ton of bricks. "Oh shit. What have I done?" She thinks to herself. She sits up slowly and goes out to the living room in a daze. She realizes the dress is still wrapped around her waist and the waistband of the panties is still holding broken fabric. She looks like a total wreck.

"Wow. Some night, huh?" A familiar voice startles Sherry. Sarah is sitting on the couch in the living room with a smug look on her face.

"I.." Sherry starts with a pleading look.

"Hey Sarah, you want to go get breakfast?" David says entering the room. He stops when he sees the real Sarah. He moves quickly to cover himself.

Sarah stands up and gives her sister a look of approval. "And you must be David. I'm Sherry. It looks like you two had a great night, but I really need to talk to my sister."

David apologizes and quickly moves around the apartment gathering his clothes. After only about 20 minutes, David is off in a cab. And Sherry has a robe from the bathroom on.

Sherry pleads to her sister, "Please don't say anything! I don't know what happened!"

Sarah gives her sister a hug. "It's okay. Look, I was being a bitch. If I knew he was that hot, I wouldn't have said no." and laughs. Sherry tells her everything that happened. Well, at least that she can remember.

"So, here is what we do. Just like when we were kids, all the things that you did is when you were me, I will say I did." Sarah says.

Despite still feeling guilty, Sherry feels partially relieved. "Thank you so much!"

"Well, I do have one condition," Sarah says.

Looking worried. Sherry says, "What?"

Sarah says, "I get to go out with him now."