tagNonConsent/ReluctanceShe Wants More than the Tip

She Wants More than the Tip


(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.)


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.

"Well, I'm waiting for my girlfriend. It'll still be a while before she gets here. I just wanted to make sure I got this table." Ryan said.

"Why do you want this table?" Alicia asked.

"Well, this is where we sat on our first date, and this is where I want us to be when I propose." Ryan said.

"Wait, are you proposing to her today?" Alicia said excitedly. Ryan reached into his pocket and pulled out the ring case. This caused Alicia to clap her hands excitedly, which in turn caused her boobs to bounce up and down, which Ryan noticed. She pulled the chair across from him out and sat down on it.

"Oh my God, this is so cute. Do you need me to do anything? Put the ring in her champagne or something like that?" Alicia said gleefully.

"Well, on our first date, I got her a chocolate milkshake for dessert. She said it was the best milkshake she ever had. So, I'm planning to buy her one for dessert today, and I was wondering if you could put the ring around the cherry on top?" Ryan explained.

"I would love to. This is so cool. I always wanted to do this, to be a part of a big, grand proposal like this." Alicia said, smiling bright. "Are you nervous?" Alicia asked.

"Yeah, a bit." Ryan said, laughing.

"Well, don't worry, I won't let you down." Alicia said.

"I know." Ryan said.

"So, do you want me to take the ring now?" Alicia asked.

"Uh, yeah, sure." he said, handing the ring case over to her. She couldn't help herself, and popped it open to check out the ring.

"What do you think?" Ryan asked.

"It's gorgeous." Alicia said, her eyes flashing. She snapped the case shut and looked at him. "I must say, I am jealous of this girlfriend of yours. I just hope, when the man of my dreams proposes to me, he puts as much thought into it as you did." This caused Ryan to blush. "Do you need me to do anything else?" Alicia asked.

"No, just don't give anything away when she gets here." Ryan said with a laugh.

"Don't worry. You're secret's safe with me." Alicia said, bringing her fingers across her lips as if closing a zipper. She stood up.

"You sure you don't need anything. Maybe something to calm your nerves?" Alicia suggested.

"Well, maybe I'll have a beer." Ryan said with a laugh. She took his beer order.

"When's the lucky girl gonna get here?" Alicia asked. Ryan checked his watch.

"About 45 minutes." Ryan replied.

"Should I be looking out for her?" Alicia asked.

"Yeah, sure. She's pretty. She has brunette hair, which she usually wears up. Her name is Anna." Ryan said. Alicia nodded. Ryan suddenly realized he hadn't introduced himself. "I'm Ryan by the way." He said, holding out his hand. She took his hand in hers.

"I'm Alicia. If you need anything else, let me know." she said, releasing his hand and walking away with a smile. Ryan sat nervously in his chair, waiting for Anna to arrive.

As Alicia walked into the kitchen, her smile faded. She reached into her pocket to check out the ring again. The diamond was a little smaller than she would prefer. Alicia knew when a guy proposed to her, he would have to put a big rock on her finger. She would be satisfied with nothing less.

"What's that?" one of her coworkers, Jane, said.

"Check it out. One of my customers is proposing to his girlfriend. Isn't that romantic?" Alicia said with a smile. Alicia hated Jane. Ever since Jane had started working here she had this attitude that she was better than everyone else there. She had a college degree! Oooohhh. Alicia didn't go to college. She knew everything she needed to know. And ever since Jane started, she had simply been a dreary little bitch. All day, every day, she bitched and moaned about how her husband had left her. By this point, Alicia knew the whole story. Jane's husband had left her for his bitch of a boss. Alicia couldn't really blame him, seeing what a sad sack Jane was. Jane was so hung up on her ex-husband that Alicia doubted she had dated since being dumped.

Alicia flat out despised her. Jane was no fun to be around, and everyone at the restaurant felt the same way. So Alicia loved to rub her personal life in Jane's face, and how she had men chasing after her. Alicia would discuss her personal life with Jane, even though she knew she hated it. She discussed her dates with Jane, and how men were fawning over her. She loved to piss Jane off and make her feel more depressed.

Alicia studied Jane's reaction. There was a twitch of jealously, and then she gave Alicia a faint smile.

"It's lovely." Jane said, before walking away quickly. Alicia smiled wickedly. She looked at the ring and then looked at Jane's retreating form. Alicia came up with a naughty idea.


About forty minutes had passed since Ryan had laid out his plan to the waitress. Alicia had been gone for awhile before chatting with Ryan a little more. She walked up front to notice a plain, boring looking girl standing up front. The hostess had stepped away so there was no one to greet her. Alicia stepped up to help her out.

"Can I help you?" Alicia asked.

"Hi, my name's Anna. I'm supposed to be meeting my boyfriend, Ryan." the girl said, scanning the interior of the restaurant. Alicia gave her a quick look, a look of surprise. A look that said, 'Really? Ryan's marrying this girl? He could do a lot better.' The moment passed.

"Yes, I will show you right over." Alicia said, leading Anna towards Ryan. As they walked, Alicia marveled at how mismatched this couple seemed. Ryan was a stud. He was tall, well muscled and was so damn cute. Plus, he was a sweet heart. A guy willing to put all of that effort into a proposal is a girl's dream come true. But, he was willing to do that for this girl? She was nothing special. A plain looking face, ratty looking hair and she had a dull body. She had no tits, and a bony ass. Plus, her cheap looking black dress did not flatter her at all. Alicia laughed to herself. If he was willing to go this far for such a plain looking girl, imagine what he would do for a girl that was actually attractive?

When they got within viewing distance, Ryan stood up and smiled. Anna walked over and hugged him and gave him a small peck. She sat down at the table across from him, sharing a look that conveyed such love for Ryan. It was clear that these two were definitely in love.

"Well, Anna, I'm Alicia, you're server. Can I get you something to drink?" Alicia said. Anna eyed her strangely before placing her order.

"I'll have a glass of white wine." Anna said.

"You know what, can you bring out a bottle for us?" Ryan asked. Anna looked at him, surprised.

"Sure." Alicia said with a bright smile, before bouncing away to place the wine order.

The rest of the dinner went by smoothly. Anna was surprisingly businesslike with Alicia, but other than that, she was in a great mood. As dinner winded down, Alicia revisited them again.

"So, guys, can I interest you in any desert?" she asked, giving Ryan a meaningful look.

"Uh, I don't think so." Anna said. Ryan started to panic. She had talked up that milkshake for years, saying it was the best she ever had. He had expected her to get one.

"Are you sure? I thought you really liked the milkshake you got here last time?" Ryan said.

"Yeah, but I'm pretty full." Anna said.

"C'mon. If you don't get it, you'll regret it." Ryan said. Anna thought to herself.

"Fine. One chocolate milkshake." she said.

"One milkshake coming up." Alicia said, heading back to the kitchen, her time for action now necessary. She waited patiently for the shake to be made. As she watched the whipped cream get sprayed on, and the cherry plopped on top, she knew the time was here. She retrieved the ring, and got ready to place it on the shake.

Ryan waited patiently, his eyes darting towards the kitchen, waiting for the waitress to emerge. He tried to maintain his conversation, but he was too nervous to fully pay attention. Finally, he saw Alicia emerge, carrying a frosty chocolate milkshake. She winked at Ryan as she walked towards him.

"Here you go." Alicia said cheerily as she set the milkshake in front of Anna.

"Thank you." Ryan said, nodding at Alicia. She smiled and stepped back, wanting to watch the festivities. Anna smiled at Ryan and pulled the glass towards her. As she leaned down to place her mouth on the straw, she saw it.

On the top of the shake, around the shiny red cherry, was a shiny gold ring. A shiny gold ring with a diamond facing her. Anna's eyes started to glisten with tears. Tears of joy. She looked at Ryan through the tears as she smiled brightly at him. Ryan stood up and grabbed the ring from around the cherry. Then, he got down on one knee. Anna turned to face him head on.

"Anna Franklin, will you marry me?" Ryan said. She nodded and smiled brightly.

"Yes. Of course. Yes!" she said with tears in her eyes. Everyone in the restaurant had been watching them. They started to clap as Ryan and Anna kissed.

"I love you." Ryan whispered.

"I love you too." Anna replied. As Ryan sat back down, Anna looked at him with such affection. Her cheeks were bright red. Ryan looked over at Alicia. She smiled brightly at him.

"Congratulations." Alicia said.

"Thank you, Alicia." Ryan said. She nodded at him as she stepped away, letting the happy couple enjoy their moment.

They basked in their new found engagement. Anna enjoyed the milkshake, calling it the best one she had ever had. As they finally finished up, Alicia returned to the table to drop off the check. Ryan quickly handed over his credit card, which she took to the register. She returned to his table a few minutes later. Anna had gone to the bathroom, so Ryan was waiting alone by himself.

"Alright Ryan, here you go." she said, handing over the receipt with a pen.

"Thanks again, Alicia, for all of your help." Ryan said, scribbling down the tip he planned to leave on the receipt. He planned to give her a big tip, equal to the total of the bill, as a way of saying thanks.

"Oh, no problem." Alicia said. "Oh!" she said, reaching into her pocket. She handed him back the ring case. "Here you go."

"Oh, thanks." Ryan said, grabbing it.

"All right, Ryan. Have a good night. You're welcome back here anytime." Alicia said. Ryan smiled.

"Thanks." he said. He watched Alicia walk away. He played with the ring case. He opened it, and was surprised to find a piece of folded-up paper inside. He unfolded it, and was surprised to see writing in pink ink. He read what was written.

"Call me." it said, followed by a phone number. After the number was one word. "Alicia." The I's were dotted with hearts.

He looked up to see Alicia walking into the kitchen. She looked over her shoulder at him, giving him a smirk.

What the hell?


Ryan was puzzled for the rest of the night by Alicia's actions. Why would she leave him her number? She couldn't possibly be hitting on him, could she? That'd be ridiculous! She took part in the engagement proceedings. She obviously knew he was taken. So what were her intentions? Did she want him as a friend? That would be the only explanation that would make sense. Even if that was the case, he would not be calling her anytime soon.

By the next day, Ryan had moved on from the whole thing. He was too busy telling his friends and family the news of his engagement. It wasn't until the evening that things settled down. Ryan and Anna decided to make their engagement Facebook official. As he went to do so, he saw he had a friend request. He clicked on it.

"Alicia Tahana has added you as a friend on Facebook"

Ryan saw the picture of the waitress's smiling face in her picture. Ryan generally never turned down a person's friend request, as long as he knew them. He thought, what the hell? It couldn't hurt. He accepted her friend request.

He changed his relationship status to 'engaged', and scanned the news feed as he waited for the comments to come in. He had a few people say congrats, and he responded and chatted for awhile. Suddenly, a new chat window appeared. It was Alicia.

"Thanks for friending me." she said.

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byTheTalkMan© 46 comments/ 226573 views/ 222 favorites

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