(This story is posted on the Literotica website. Do not repost anywhere else without the author's consent. This story deals with similar themes as the stories by wannabeboytoy, seducedHylas, and Dark Betrayal. This story features characters from my stories "The Body of Justice" and "The Hotel Room". It might flesh out this story a bit if you read those stories first, but it is absolutely not necessary to do so. This story stands on its own. Also, I would like to thank my biggest fan for his help preparing this story. I do not condone any of these actions in real life. This is just a story. Enjoy.)
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Ryan arrived at the restaurant an hour early. He knew this had to be perfect.
He hadn't been back here at O'Malley's for a few years now. It still looked the same. It was never the classiest place in the world, but it had character. It was a popular place among college students, which Ryan was when he had first met Anna.
They had both been undergrads when they had first met. He was in pre-med, and she was in pre-law. They had been set-up on a blind date through a mutual friend. It was baffling that they had never met. They were both star students, ivy-leaguers and clearly destined for success. They had first met at this bar and restaurant, O'Malley's. Ryan still remembered how nervous he was when he was entering the bar to meet her. Despite his success in the classroom, he had never been particularly successful with girls. It's not that he was bad looking, quite the opposite, he was actually very good looking. But he was extremely shy. He had had girls hit on him throughout high school and his first few years of college, but he was too shy to notice the signals they were sending out. He was a good guy, friendly and soft spoken. His parents had done a good job with him.
Ryan had walked into the bar that night, nervous, after going a few years without having a date. He was dressed in a polo shirt and khaki's. He looked around, checking for the girl he was supposed to meet. He looked around nervously, until he felt a hand on his shoulder. He looked up into the smiling face of the pretty brunette standing above him.
"Are you Ryan?" she asked. He looked at her. He was shocked to see how pretty this girl was. She couldn't be his date, right?
"Yeah." he said nervously, thinking this girl might be here to tell him his date wasn't showing up.
"I'm Anna." she said, holding out her hand. He shook it quickly, before they sat down. The rest of the night was a blur. Ryan had never been a smooth talker, but he found the words easy to come by as he talked to Anna for hours. The conversation between them was effortless, and Ryan gained more confidence in his words as the night progressed.
Ryan was in awe of Anna. She was so pretty and so easy to talk too. Plus, she was extremely intelligent. She was in pre-law, and you could immediately tell that she would be successful professionally. She clearly had the drive and ambition to go places. This was a feature that Ryan found extremely attractive. And she was so funny and charming. For Ryan, it was puppy love.
The night ended with them exchanging numbers, and Ryan had to stop himself from calling her immediately. When he did finally call, she was eager to see him again too.
From that point, their relationship was a whirlwind. They spent whatever free time they had together. All their friends said the same thing about them: they were a perfect couple. They were so cute together. They were meant to be.
Ryan grew up quite a bit thanks to Anna. Gone was the nervous, stuttering and repressed teen that got nervous around pretty girls. He was now a confident, charming man. His friends saw a new side of him as he was now more outgoing than ever. People loved the new him. And Anna loved him. And he loved Anna.
Anna had truly turned him from a boy to a man. Ryan lost his virginity to Anna after a few months of dating. As with most first times, it was more awkward than pleasurable. But, in due time, their lovemaking went from awkward to very good. He now saw what he had been missing out on while being a virgin.
So they dated for a few years, knowing in the back of their head that they would get married eventually. Everyone knew it. Why wouldn't they? He was going to be a doctor and her a lawyer. The perfect power couple. They were destined to have a great life together.
The only thing that delayed their inevitable union was their busy schedules. Ryan and Anna were too busy with school to take the time to get married. Ryan knew he was going to propose for awhile, but he was waiting for the right moment. He thought for a long time about the perfect romantic gesture, before he finally came up with the perfect idea. That's what led him back into O'Malley's, on his and Anna's three year anniversary.
Ryan scanned through the restaurant and saw that the table he wanted was open. He walked up to the hostess at the front.
"Hi." Ryan said to the hostess.
"Hi!" the perky hostess said with a bright smile. "How many?" she asked.
"Uh, it'll be two. Could I possibly get that table over there?" Ryan asked, pointing at the open table.
"Um, sure, no problem." she said, grabbing two menus. She led Ryan over to the open table and set the menus down.
"Enjoy your meal. Alicia will be over soon to serve you." The hostess said with a smile, before walking away.
Ryan sat there nervously, wanting to make sure everything was perfect. He looked around making sure he knew where everything was. He waited for the waitress to show up. He needed to discuss his plan with her.
He looked up as he saw a sour looking waitress walking towards him. She looked like she would rather be anywhere else. Ryan spied her nametag, and it said 'Jane'. Ryan sighed with relief as she walked by him. A girl with a sour mood would not have made his plan easy. He so was distracted by the sour looking waitress that he didn't notice his waitress bounce over to his table.
"Waiting for someone special?" A peppy female voice said. Ryan looked up at the waitress standing next to him. He was taken aback by how pretty she was. Stunning really. She had long brown hair down to her mid-back. Her face was gorgeous, with a slight tan. She had big, expressive eyes. She also had full, pouty lips, and she was displaying her bright white teeth as she smiled at him. She looked a couple years older than him, maybe 28 or 29.
"Uh, yeah, something like that." Ryan said.
"Hi, I'm Alicia. I will serve you today. Do you want me to come back when she gets here?" the waitress, Alicia, said knowingly.
"Well, it might be awhile before she gets here." Ryan replied.
"Well, do you want something to drink?" Alicia asked.
"I'll have a glass of water, thank you." Ryan said.
"Sure, I'll be right back." Alicia said, bouncing away. It was at this point that Ryan realized how good of a body she had. She walked in a way to highlight her great butt, which she had stuffed in a tight pair of pants. It looked round and firm. Ryan shook his head, clearing away his admiration of this waitress's body. He thought about his planned proposal, and how much he needed to let Alicia in on his plans. As Ryan saw Alicia emerge from across the restaurant, holding his glass of water, he noticed something else about her.
Alicia had really big breasts. Like huge. Just massive breasts. And she was wearing a tight blouse to really highlight them. He hadn't realized her tight black blouse was unbuttoned enough to give a hint of cleavage. She must use those to get the tips, Ryan thought.
Alicia returned to the table and set his water down.
"Big date?" Alicia asked with a smile.
"Well, kinda." Ryan said.
"How can something be kind of a date?" Alicia asked.
