Greg finally made it home from work. It had been an unusually long day and he was tired. He walked into his modest two-bedroom apartment, loosened his tie, and kicked off his shoes. He walked to the refrigerator, pulled out a beer, and the pizza box left over from last night, and then he went back to his home office and set his dinner down on his desk. He pushed the button on his computer, opened up the beer, and went to his bedroom to change clothes while it booted up. He changed into a pair of shorts that he probably wouldn't ever wear outside of the house. They had paint stains on them, and a hole in a rather embarrassing spot, right in the front, but they were comfortable. He put on a tank top that was in about the same shape.
On his way out of the room, he saw himself in the full-length mirror. He was in his forties, and if anyone was asked to guess his age, they usually hit it within a couple of years. His hair was turning gray in a few spots. Not in the way that made him look distinguished, but in the way that just made him look old. He was a little over weight, Not really fat, but a little out of shape, and he sucked in his gut, to make himself feel better more than anything. He went back to the other room to his computer desk, to start the night's entertainment, while he got a little extra work done.
He'd been married to who he thought was the girl of his dreams. They made a home together and lived very happily, or at least he thought, for fifteen years. They had one child together, a boy that lived with his mother. He got to see him on some holidays, and usually for a few weeks in the summer. When they were divorced, she remarried quickly, and moved out of state. He made excuses to himself that he was just too busy to get involved with someone, or he would start dating next year, maybe. The fact of the matter was that Greg was a little shy, and very afraid of getting hurt again.
Almost all of Greg's entertainment came from the computer. Chat rooms mostly, the occasional private message would come through, but usually ended quickly when photos were exchanged. Most nights he simply checked the chat rooms out, trying to find a woman that was showing off her body on her video camera. Usually the night ended with him horny and frustrated, with a paper towel full of cum in the wastebasket and no closer to a relationship then when he booted the computer up. That was until he met Abby.
He'd met Abby in a chat room. He was just making conversation, and telling a few jokes. She messaged him privately to tell him that she thought he was funny. This led to an all night conversation. She didn't ask him for his picture and she didn't have one on her profile. She had her age listed as twenty-five. Kind of young for him, he thought at first, but it was a conversation with a girl that lasted more then twenty minutes.
Inevitably, the subject of pictures came up. He got hers first. She wasn't ugly, or fat. She was gorgeous. She was tall, and slender, with an angelic face, and an outrageous body. Panic immediately set in. She was so far out of his league, he thought, that she was in another solar system. Now it was his turn to send his photo. He warned her that he was older, and not in very good shape. She didn't seem to care. "Send it." She pleaded. "I wanna see what you look like." He selected the picture that he was going to send. It was recent, and he was pretty dressed up as the picture was taken at work. He closed his eyes, and with a shaky, sweaty hand, clicked the mouse. The next few seconds were unbearable. Every scenario of rejection went through his head. He looked at her username expecting that it would go offline, and she, of course would put him on ignore. He stood up, and walked out of the room.
He went to the kitchen, slung open the refrigerator, grabbed a beer, and figured he'd might as well get drunk. It was over. He repulsed her he knew it. He walked back into the room, looked at the computer screen, holding out the last little bit of hope. The ding that told him a message was waiting almost scared him. She'd answered him back. He clicked on the message, still being the pessimist that he was, expecting the "You look like my father" comment. "Your cute" was what she said instead. He couldn't believe what he read. He even asked her if she was sure, and made sure she was looking at the right photo. She explained that she liked older men and that she always had. She went on to say that she'd had enough with the younger, "tough guy" types that didn't know how to treat a woman. She had a career and didn't need anyone to take care of her. She just needed someone that would love her the way she wanted; the way she needed to be loved.
Soon, phone numbers were exchanged, and they talked on the phone sometimes. She lived in another state and it was expensive to call, so the computer was still their main form of communication. She purchased a web cam, and encouraged him to do the same. The picture she sent him earlier was really she, and he still didn't turn her off. She even thought his ragged shorts were cute.
They moved on to a few sessions of cyber sex, where he watched her masturbate, and she watched him. This worked for them for a time. Four or five months had gone by when during one night's conversation, she brought up that she wanted to meet him. She explained that she had some vacation saved up, and one of her friends had a house on the beach. They would meet at a neutral location, of course. There was always the possibility that neither was who they appeared to be, but she really wanted to meet him. They set up a date, a time, and a place. He would have to fly, and planned on renting a car. The vacation house was only a few hours from where she was.
Greg went shopping, every day, for a week before his vacation, trying to pick out the perfect outfit. He didn't want to look like an old man trying to look young, but he wanted to look good. His vacation was scheduled, his flight was booked and he had more new clothes than he'd bought in three years. He packed his bags, at least three times as he changed his mind about what he wanted to wear the first day. He carried his bag down to his car, took a deep breath, started the engine, and left for the airport. He pulled his car into the long-term lot, got his bag out of the trunk, and headed for the terminal. His cell phone rang before he got out of the parking lot. It was her number on the caller ID. His first thought was that she wanted to back out, as that was his luck with ladies lately.
"All ready to go?" Abby asked him.
"Uh, yea, I'm at the airport now." Gregg explained. "Are you ready for me?"
The phone was quiet for a second or two. "Yep, I just wanted to know that you were sure about this."
"Of course I'm sure." He sounded a little astonished at the question.
"Ok, so we're still on for dinner?" She had a question in her voice like she was nervous.
"Are you sure you want to do this Abby?" He asked, not sure if he wanted to know the answer.
"Yea, I'm sure. It's just that 'meeting someone new' thing, ya know?" She reassured him.
"Yea, I know. I'm sweating bullets." He admitted.
"I don't bite." She said sounding a little seductive. "I nibble a little, but it's affectionate." She giggled nervously.
Greg smiled at that comment. "Well, I've got to get through security babe, I'll see you in a few hours."
"Ok, have a safe trip, and I'll see you." She hung up.
Greg made it through security without any problems, and was soon on the plane ready for takeoff. The flight was somewhat bumpy, and he was definitely ready to disembark when it landed. He retrieved his bag, rented his car, and headed to the restaurant. He studied the map he'd printed, and tried to negotiate his way through the tiny beach town. He pulled into the parking lot, and parked his car. Should he go in, and wait, or stay in the car. If he stayed in the car, it might make him look like a stalker or a maniac. He went into the restaurant, found a seat at the bar where he could watch the door, and waited.
Abby drove by the restaurant for the third time. She just couldn't bring herself to pull in to the lot. She wanted to see him, but didn't want to disappoint him. Would he think she was too tall, or too skinny? Maybe her laugh would turn him off, as she tended to snort a little if she laughed hard enough. Or, perhaps the fact that she was a CPA at twenty-five, and probably made more money than he does, would intimidate him. Maybe she was too immature for him. Finally on the fourth trip up and down the same block, she pulled in. She looked through the parking lot trying to see his car, and then realized that he was in a rental. It could be any of them. She parked her car, and checked her makeup and her neck length auburn hair in the mirror. She got out, and straightened her dress. Everything looked pretty good, but she couldn't help being self-conscious. She walked in the door, and tried to find him.
.... There is more of this story ...