First Date

Jack was still wondering how he found himself in this position. He had just finished looking at himself in the mirror, dressed in a nice shirt, tie, and a freshly pressed pair of slacks. He walked out of the bathroom, into the kitchen to grab his car keys and wallet before getting in his car and heading over to Angie's house. On his way over he thought about the events that had occurred over the last couple of weeks that led him to this point.

Jackson Harris had not been on a date in over two years. Not since he and Heather had split up. And it had been even longer than that for the last time he had sex. Heather stopped putting out for him six months before they broke up, although she had no problem at all with putting out for a few of the other guys she knew. He and Heather had been together since their junior year in high school. They even decided to go to the same college so they could continue their relationship. But, halfway through their final year, Heather told him she was tired of the same old thing and that she wanted to date other people. That floored Jack, and he hardly ever saw her again, only every now and then around the campus. He has since heard that she ran off with the captain of the football team and they are now living in the mid-west somewhere.

After graduation, Jackson went back to his hometown to put the degree he received in Accounting to good use. He got a job with a growing corporation keeping their books. He had a lot of responsibility( keeping track of expenses, doing payroll, making sure the company's bills were paid), and he received a very nice salary for it.

One day there was a knock on his office door and the Human Resources Dept. head poked her head in. She told him she was showing a new hire around the building and that the new person said she knew him.

"Well let me see this person, then," Jack said as he put some paperwork into his IN basket.

A beautiful young woman came into his office and his mouth dropped. She was the same age as he was, had dark hair that went halfway down her back and a body that would make most super models jealous. She smiled widely at him and started blushing due to his gawking and lack of speech.

"It has been more than four years since I have seen you and you can't think of one thing to say?" she asked.

"Angie!" was all he could manage to say. Jack got up and walked briskly over to where she stood and wrapped his arms around her.

"Jack, you know you are not supposed to do that," Melanie, the HR head said.

"It's all right," Angie said. "We're old friends, like I told you."

Jack and Angie grew up on the same street, but they did not become friends until they started high school. They were the only ones in their neighborhood that rode the bus to and from school. Since they were the only two waiting at the bus stop every morning, they passed their time by talking and getting to know each other. They became good friends and even dated for a little while in their sophomore year.

They broke the embrace and looked at each other. Jack asked her what position she had applied for and Melanie said she was going to be the new secretary in the office. He asked if he could give her the rest of the tour, to which Melanie agreed. The two of them left his office and he showed her the rest of the building. The company that they worked for was a distributor of kitchen supplies to retail stores and restaurants in the Northeast. The two of them went out to lunch that day and got caught up on each other's lives.

After Angie started her job, she and Jack would hang out like they did before Jack went away to college. They would go out to dinner every now and then or one would go to the other's house to watch a movie. There was no real physical attraction between them. They just enjoyed each other's company.

A couple of months later, Angie decided to ask him about what happened between him and Heather after they had watched a movie and had some popcorn and beer. Jack told her he thought they grew apart somewhere in their relationship, but could not remember feeling that way when they spilt up. He told her he remembered not having sex with Heather the last six months of their relationship. It had bothered him, but she did not seem to be affected.

"That's probably because she was banging the football team," Angie said.

"That would explain it," Jack smiled.

Angie laughed then said, "Don't you think it is time to start dating again?"

"Probably," he sighed. "I just have not met the right girl yet."

"Well, what if I found her for you?" Angie asked.

"Sounds like you already have someone in mind," Jack accused her.

"Maybe. Would you be interested?"

"Who are you thinking of?" Jack wanted to know.

"Tell me who it is first and I'll tell you if I am interested or not."

"Fine," Angie said. "It is my cousin, Kelly. You remember her, don't you?"

The look on his face told her that he did.

"You mean the cousin that wears the glasses that are about an inch thick, and about 40-lbs. overweight?"

"She has changed a lot since you last saw her, Jack," Angie shot at him. "She lost all the extra weight and she now wears contacts. She is very pretty."

"You have to say that," Jack said. "You are related."

"Jackson!"

"Angela!" he mocked her.

"C'mon. Please? For me?"

He took another sip from his beer bottle. He was desperate to find a way out of this.

"Doesn't she live a couple of hours away from here?" he said. "I don't think I want to drive out there for one date."

"You don't need to worry about that," Angie told him. "Kelly is coming here to visit me for a little while. She will be here Tuesday night."

"How long is she staying?"

"Couple of months, I think," Angie said.

"What about her job?" Jack asked.

"She can get one anywhere she wants. She has a lot of experience."

"What does she do?"

"Not sure," Angie admitted. "All I know is that she left her last job with a huge severance deal, so she can afford to not work for a while. She was going to travel the world, but she wanted me to go with her. As I cannot afford it, she is coming to visit me instead."

"So why are you tryin to set us up?" Jack asked.

"She, like you, has not been out in a long time," she said. "She needs to get out. It will be good for both of you. That, and, she has always had a crush on you. Ever since the first summer we all hung out together. She was really disappointed when you started dating Heather."

"All right, listen. I will go out with her once," he said. "And only once. So after this, don't ask me again. Deal?"

"I promise."

************

Jack pulled up to Angie's house and prepared himself for the worst. Although Angie had told him that Kelly had changed quite a bit since he last saw her, he was still very skeptical. As he rang the doorbell, a feeling of doom came over him. He was not sure he wanted to do this after all.

Angie opened the door and greeted her friend.

"Come in and sit down," she said. "Kelly will be down in a minute." She let him in and directed him to the sofa. She asked if he wanted anything and he declined. "So, where are the two of you going tonight?"

Jack gave her the name of one of the finest Italian restaurants in the North End. "After that, it is up to her," Jack said, his voice betraying how unenthused he was about the date.

"Oh, cheer up, will ya?" Angie said. "You never know. You may just enjoy yourself tonight."

Just then they heard a door open upstairs, and a few seconds later, high heels clicking their way down the hardwood steps. Jack stood up for the arrival of his date. When she came into view, his jaw dropped to his chest. The woman coming down the stairs was beautiful. Her red hair came down to her mid-back; her green eyes twinkled with every pad of her foot. Her smile was wide and showed almost every one of her pearly white teeth. Angie looked over at her friend.

"Down, boy," she whispered in his ear as she used her hand to close his mouth. "See. I told you she has changed."

Jack was awestruck as he watched Kelly enter the room. He saw that the little geeky girl he remembered from their childhood was gone and this gorgeous goddess had taken her place.

"Hi, Jack," Kelly said as she stepped up and gave him a hug. "Long time since I last saw you."

"Er . . . yeah . . . a long time," was all that he managed to reply. Her perfume entered his nostrils and he thought she smelled as sweet as she looked. They broke the embrace and Kelly stood back from him. Jack looked at her again. Her red hair shimmered like silk, the flawless complexion of her face, even her outfit of a pink blouse and tight black skirt was perfect.

"So, where are we going, handsome?" Kelly asked.

"To dinner, then it's up to you," Jack said.

"Hmmmm. A world of possibilities," she said with a wink.

When they left the house Jack was a perfect gentleman the entire evening. He opened the car door for her, the door to the restaurant, and made sure he beat the maitre d' so he could pull the chair out for her. Not figuring he would actually be into the date, Jack brought a very small amount of money with him. Now that he was trying to impress Kelly, he ordered one of the most expensive bottles of red wine for their dinner. As they ate there was the typical first date chatter. She asked him about his job and listened intently while he talked. When he was finished discussing accounting, he asked what she did.

"Angie didn't tell you?" Kelly asked.

"I asked her, but she said she wasn't exactly sure. All she did know was that you left and got a really nice severance deal," Jack told her.

"Yeah. Quite good," Kelly told him. "So much so that I may need to get myself an accountant." She winked at him again, and all he could do was smile at her.

"So, what happened?" he asked. She looked a little hesitant to talk to him about it. "If you don't want to tell me about it, it's ok. I was just curious, that's all."

Kelly took a deep breath. "I don't mind telling you about it, it's just that whenever my profession comes up on a date, it is usually the last time I ever see the guy, or he expects things from me later that night."

"Well, I will be honest with you," Jack said. "I will not judge you on what you do, and I will not expect anything after dinner. Like I said, after this, it is your choice on what we do. If you want me to take you back to Angie's, I will. It is all up to you."

"No, it's all right," Kelly told him. "I will talk to you about it."

"So what happened?"

"Well, I had a problem with one of my managers," she explained. "So I quit. When I went back to pick up my last paycheck, he told me I could only get it if I . . . er . . . pleased him orally."

"You're kidding?" Jack said unbelievingly.

"No. That is what he said. So, I called a lawyer friend of mine, and the mere threat of a lawsuit against their company had them opening up their checkbooks. They paid me a pretty penny to keep quiet, enough to where I do not have to work for a few years, at least."

"Jesus, how much was it?" Jack asked.

"I can't get specific," she said with a smile.

"What is it that you did?"

"I was a cam girl."

"A what?" Jack asked.

"A cam girl," Kelly repeated. "You do know what a cam girl is, don't you?" When Jack shook his head Kelly started to giggle. "A cam girl puts on a sexy show over the internet. You have never seen a cam website?"

"No. I hardly ever get on my computer anymore," Jack admitted. "And when I did there was only one site that I visited."

"You never went to a porn site? I thought all men did that."

"I came across a few," Jack said with a grin, "but I was never one to sign up for them. Too cheap."

"Judging by this bottle of wine that does not seem to be the case," Kelly said as she raised her glass to her lips.

"Well I do splurge every now and then. Especially when in the company of such a beautiful woman."

They finished their meal (Jack paid the bill with his credit card), and got ready to leave. Jack opened the car door for Kelly once again, and closed it gently when she was inside. When he got in his side, he turned to her and asked what it was that she wanted to do next.

"Let's go back to your place," she said.

He drove the 20 minutes to his house and the two of them went inside. He gave her the tour of the house, since it had been a few years since she had been inside. Jack bought the house that he grew up in from his parents. They wanted to retire in Florida, but did not want to have a mortgage up north anymore. When they got to the den, Kelly found that was where Jack kept his computer. As she walked into the room, Jack asked her if she wanted anything to drink.

"Come in here with me, Jack," Kelly called out. Jack soon entered the room carrying two glasses of wine. He found her sitting in the high-backed leather chair in front of his computer. As he stood behind her, he saw that she had the internet up on his computer and was typing in a website. When it was finished loading, there were several pictures of scantily clad women.

"This is the site of the company that I worked for. This girl right here," she was pointing at a striking brunette in a leather corset with the name Kiki under her picture, "she is one of my best friends. She is the one who told me to contact the lawyer. She should be on right now. Wanna see her show?"

"What does she do in her show?" Jack asked.

"Jackson Harris! Have you lived a sheltered life or something? How could you have gone to college and have no idea what kind of show a web cam girl does?"

"Hey, when I was in college, I was too busy busting my ass studying to look at girls over the web," he said smiling. "That and I had a girlfriend. Never had a need to look at cam girls."

"What a shame," Kelly said as she typed in a user name and password, "because this is what you missed."

She clicked on the picture of Kiki and was taken right into the room. She started typing and the girl on the screen reacted with glee when she saw Kelly's name pop up. The two of them started typing away with each other, wanting to know what the other was up to. When Kelly told Kiki that she was on a date, Kiki looked into her web cam, put up both of her thumbs and smiled wide. Kelly then clicked on a tab at the bottom of the page that said 'go private.'

When it was just Kelly's and Kiki's names in the room, Kelly rummaged through her purse and pulled out a card. She saw Jack's office-style phone sitting on the corner of the computer table.

"Is that a speaker phone?" she asked. When Jack told her it was, she asked if he minded if she used it. He agreed and she dialed the number. The line rang twice before a woman picked up.

"Where have you been?" the woman on the phone asked.

"I came out to visit my cousin," Kelly said. "My date's name is Jack and he has never seen a cam show before." That was when Jack figured out whom Kelly was talking on the phone to. He looked back at the screen to see Kiki holding a cordless phone to her ear.

"And what did the two of you do tonight?" Kiki asked.

"Well, we had dinner, then Jack said the rest of the night was up to me," Kelly told her. "So, this is what I chose to do; Give him his first cam show. And who better to give it to him than you?"

"Ooooo . . . a virgin! I like those!" Kiki said with a wink. "And what will you be doing while I entertain him?"

"Don't you worry about that," Kelly said. "I will be keeping myself busy."

Kelly got up from the chair, pushed it back a little, and had Jack sit down. He was looking at Kelly when she smiled and gestured at the computer monitor. When he turned his eyes to the screen he saw that Kiki was topless and starting to take her panties off.

"So, Jack. How is the date going so far?" Kiki asked.

Jack gave a little laugh and said, "A lot better than I thought it would. Kelly has changed quite a bit from when we were kids."

"Kelly, is this the same Jack you used to tell me about? How you had such a huge crush on him?" Kiki asked as she sat up straight.

Kelly, who was now standing behind the chair and watching the show while she rubbed Jack's shoulders simply said, "Yes."

"Ok, ladies," Jack said, "now how does this work?"

"You can either type or tell me what to do and I will do, if I can," Kiki answered. "I have toys," she panned the camera over to show the dozens of vibrators and dildo she had on a shelf. "I also have different outfits I can get into for you. Your wish is my command for the next half hour."

Jack looked back at Kelly. "What do you want her to do?"

"Huh uh, buster," she said, shaking her head, "this is your show to direct. I am staying out of it."

"Please?" he pleaded. "I don't know what to tell her to do."

"Well, Jack," Kiki said through the phone, "why don't I do what I normally do and you just sit back and watch? Sound good?"

Jack agreed to that and watched as Kiki spread her legs to show herself to the camera. Next she started rubbing her clit and talking into the phone, asking if Jack could see how wet her pussy was getting. The show was definitely having an effect on him. As he watched Kiki, and felt Kelly rubbing her hands on his chest now, his penis started to get firm in his pants, almost to the point where it was starting to get uncomfortable. Kiki put the hand set down, put on a connected headset, and reached over to the shelf and pulled down an eight-inch red vibrator.

"Hey, Jack," Kiki called. "How do like it so far?"

"Very nice," Jack said.

"Mmmmm, listen to this," she said as she turned the toy on.

It buzzed to life and she slowly applied it to her clit. She was moaning and saying how she felt she was going to cum soon when she started to slowly insert it into her pussy. As she fucked herself with the vibrator, she used the fingers of her other hand to rub her clit. Jack was so enthralled with the show that he did not notice Kelly crawl under the desk and unzip his pants. It was not until she wrapped her lips around the head of his cock that his attention was ripped away from the monitor.

"Oh, wow!" he gasped.

"You like what you see? Or is Kelly up to something?" Kiki asked.

"Ohhhhh," he gasped again as Kelly really started sucking on him. "It's a combination, I think. Ohhhh, God!!"

Jack thrust his hips up, forcing his cock deeper into Kelly's mouth. She looked up at him, his cock lodged firmly in her mouth, and moaned her approval. The vibrations that went onto his cock made Jack grab the armrests of the chair.

"Jack? Is Kelly giving you a blow job right now?" Kiki said.

"Ahhhh yeah . . . ," was all he could answer.

"Mmmmm," Kiki moaned. "Does it look like this?" she asked as she pulled the vibrator out of her cunt and started sucking on it, taking it almost all the way down her throat.

Jack groaned a, "Yes" for Kiki. He then put his hands on Kelly's head. She sucked on him while licking the underside of his prick with her tongue. Kelly took his cock out of her mouth with a "POP."

"That sounds wonderful, Kelly," Kiki said. "Describe it to me."

Kelly kissed the head of his cock, then turned her head so she was talking in the direction of the phone.

"Well, it is about 6-1/2 inches long, hard as steel, almost as thick as my wrist, and," she sucked it back in her mouth, bobbed on it three times before coming back up to say, "delicious."

"You are a dirty girl," Kiki said. "Get back to suckin' so we can finish him off."

Jack was close; both he and Kelly knew that, but he did not understand how Kiki could have sensed it. When Kelly started sucking him again, all thoughts of Kiki went out of his head. Kelly reached inside of his zipper again and brought both of his balls out. She dipped her head down and licked both before she took each one into her mouth. As she did this, she jacked him with her right hand. She licked her way back to the head of his cock. When she got there, she saw a large amount of pre-cum waiting for her tongue. She engulfed his cock once more, sucking for a few minutes before she heard Jack start mumbling something.