Happy Hour Diners Pt. 02: Cassie

Disclaimer: All characters appearing in this work are above 18 years of age and fictitious. Any resemblance to real persons, living or dead, is purely coincidental.

Note from author: Feel free to let me know what you think of this. I hope you enjoy it. This chapter is written from the perspective of Cassie, one of the waitresses at the diner. She is a 5 foot 2 inch tall, 21 year old brunette.

~

I like to think of myself as a confident person but I think others don't quite get to see that side of me. As a physics major in college, a lot of time is spent studying, doing schoolwork and stressing about how to afford my life, broke college student and all. I've managed to save up some money for basic expenses, like clothes and makeup, and let me tell you, it's not easy at all when you're just starting out in your "glow-up" journey.

Glowing up has created more stress in my life than I thought was possible. So far, I had gone through life without being checked out much. Which meant minimal attention from men, aggressive or otherwise. Anyone could get catcalled in a bad part of town but I had simply never shown up until now as "that" girl who everyone wants to get with in, say, a workplace or school setting.

What motivated me to make myself look better was just to figure out what kind of aesthetic I would like to project once I'm finally working in a white collar job based on my college degree. A year or two of experimentation with makeup and clothing should be more than enough to settle on a comfortable yet attractive looking style. However, I'm surprised I didn't get into all of this before, considering how much I'm starting to enjoy playing around with my looks, despite the newfound stress.

Joe, my boyfriend of six years starting in high school, broke up with me a month after my glowed-up version made its public appearance. He got jealous of others giving me too much attention while we were out on dates, and I'm a little ashamed to admit that I'm relieved that he initiated the breakup. I was more than happy to let go of his wimpy ass on his own terms because I simply could not muster the emotional energy to initiate it, with his multiple hour long phone calls draining my soul every other day. It should've ended back in high school itself and had dragged on for way too long.

So you might be wondering how I'm still stressed when in fact I have gotten rid ofthe heaviest weight in my life? The sharp spike in the amount of attention I'm given by men wherever I go. Overeager pursuers who won't quit blowing up my messages or trying to get a chance to find me alone after class to beg me to date them. I know I should be very flattered, but I still can't wrap my mind around being given this much attention and frankly, it's just nerve wracking to keep worrying if my lack of interest might offend some dude to act out like an aggressive jerk. I've only ever been with Joe, and I'm sure he wasn't the best lover to have. With his emotionally draining personality, I stopped feeling sexually attracted to him a long time ago and would almost always wind up masturbating to get myself off after dates. Our libidos weren't compatible and it was only after finding out how sexually content my friends were that I realised that this wasn't going to work out in the long run.

I'm not looking for anything serious at the moment as I'm still working up the courage to let myself be with other guys with my new avatar. Love life aside, it's easier keeping up with my studies and my lifestyle now that I am in my third year of college, with just a year and a half left until I'm a free bird. Yeah yeah, I'm aware these are the best years and the rest of adulthood isn't exactly a walk-in-the-park with more responsibilities. But a girl can dream, can she not?

Speaking of dreams, I slept through my alarm today and I'm rushing to get dressed for my waitress interview at some diner downtown. Lola, my old coworker from Starbucks and current best friend, currently works at this place and suggested that I give this new position a shot because it pays a lot better than being a barista. Maybe the customers tip really well there.

I hope I get the job.

~

Lola told me to show up at 6:45pm and wait for her in the diner. I'm sitting in one of the red vinyl booths by the window looking out into the busy street when I hear her voice call out my name.

"Hey Casserole, lemme see you. Hmm." Lola looks absolutely gorgeous in her pink waitress outfit with her makeup and hair all done up in a vintage actress style. Now that I think about it, she bears a striking resemblance to Joi Lansing.

She looks at my outfit and inspects my hair and makeup closely.

"You look just fine. The clothes don't really matter since you'll be wearing one of these anyway," she says, pointing to her outfit.

Taking my hand in hers, we start walking towards the elevator where I guess the interview will take place.

Once we've arrived into the lobby of the "office", which is basically the same interior design as the rest of the diner downstairs minus the booths, Lola asks me to wait and walks on ahead to knock at a door at the end of the hallway.

A female voice responds from the room but I can't hear her well enough from where I'm standing. Lola pokes her head into the room and says something. She then turns around and gestures with her hand at me to come into the room.

I'm greeted by a beautiful dark haired woman seated behind a mahogany desk with her hands on top of the table. She is dressed in an off white pant suit which makes her golden tan complexion absolutely pop. She looks like she is a very gracefully-aging mature woman who must be in her 50s but can easily be mistaken for a freshly turned 38 year old, if not for the slight signs of aging on her neck and the back of her hands.

"Please take a seat." She says with a smile. Her accent is a mix of American along with either Spanish or Italian. "Lola, you may go now."

"I'm Jovanna Conti. I'm the owner. Lola said you would be a good fit for this place and I'm glad to finally meet you after all she's told me about you."

"Hello, Ms. Conti. I'm Cassandra Hall."

"So, tell me, Cassandra, have you ever worked as a waitress before?"

"I have, briefly, for about a year in high school. I'm currently working as a barista at the Starbucks on Diver's Lane, a few blocks from here."

"High school, huh? You look like you still could be a student there but I'm told that you're in college." She is inspecting my face very carefully as she is talking.

I don't know how to respond to that. "Well I'm only 21 right now and I don't think that's much older than 17 or 18..." I laugh nervously and feel relieved when she smiles in response, her thick golden dangling earrings moving amidst her thick glossy dark brown hair. She is dressed quite formally for running a diner that looks so old school. It's very well designed and they obviously have a vintage 50s theme here, but Jovanna looks out of place in her extremely glamorous and posh outfit. Well, she's the owner and not a staff member, so I guess it makes sense...

"Well, I'm glad to know you have experience in this industry. You look perfect for the job, and you will do splendidly for what I have in mind for you."

I try to smile politely. What does she mean by that? I'm going to be a waitress here, that's all. Maybe she's just a bit dramatic. Could be the Italian genes. And she's old too.

"Have you had a boyfriend yet, Cassandra?"

I feel my smile start to shrink. What sort of a question is that? Why does she want to know that?

"I'm not dating anyone at the moment."

"That's not what I asked." She replies gently, her smile turning into a bit of a smirk.

"I'm asking if you have had a boyfriend. More specifically, if you've had sexual intercourse yet."

My cheeks are starting to burn up. What is going on here?

"I-I..." I stutter. "I have had sex...yes..." I reach forward to grab the glass of water on the table.

"Hey now, don't be nervous. I know it's a bit forward of me to ask you this so directly and you're here expecting an interview. I apologise if I've made you uncomfortable, Cassandra. Cassie... may I call you Cassie?" She reaches forward with her palm facing up, as if asking me to put my hand in hers. Reluctantly, I nod my head in a yes, putting the glass back down and hold her hand.

She rubs her thumb on the back of my hand in a comforting gesture. "Cassie, you're extremely beautiful. I'm sure you're told that very often. But you need to work on your confidence. A girl like you could have it all, and I know you're studying to work as a researcher. Lola has told me you're incredibly smart and with your looks, you could go on to really make it big in the job market. No doubts about that. But you need to work on how you carry yourself. Trust me, I know what it's like to be a woman and carve out a successful career."

"I'm a lawyer and a partner at my own law firm that I run jointly with my husband, Richard. This diner is something I inherited from my father and I love it too much to ever part from it. I don't personally oversee the daily affairs here, I'm too busy with my practice for that. Richard and I only come here to enjoy this and personally interview some of the folk we hire."

I'm listening intently with my heart beat going wild inside my chest with every passing second, waiting for the absolute second her lips will utter the words where it makes sense to ask me about my sex life. I don't quite know if I'm angry or afraid.

"We're very particular about what we offer to our guests. And we don't pick easily. You could say we're hard to impress," she says with a slight shrug as if she's very proud of the fact.

"What I'm offering you is an opportunity to work on your confidence and really own your looks. You hardly look aware of what you have and it would be such a crime to let such talent go to waste." Her eyes move down to the level of my chest, lingering there for quite a while as if she is undressing me with her eyes.

What the fuck is she going on about? My talent? My confidence? I don't have to put up with this crap, I came here to give my interview for a waitressing job, my sex life is nobody's business. Gritting my teeth, I let her talk.

"We want to offer you a position as a special waitress here. You won't be working at the diner that you probably saw when you came in. We have a discreet facility that we use for customers who want a little extra."

Is she still talking about waitressing? I look at her puzzled and she continues in her gentle, matronly manner.

"Our Sunset waitresses bring out orders and feed the customers, and it usually ends in sex. Our customers get to decide which one of our girls they get, and no, we don't give them your photographs or any of your personal details. They only tell us their broad preferences, like physique and race. And we're also looking to hire men soon, I'm looking forward to that." She grins as she says that last part.

"We thoroughly vet the customers we allow to see our girls and don't worry, we have security here and cameras monitoring every square inch of this place. You'll be signing a non-disclosure agreement and we'll talk you through the terms of the contract. I can promise you right away that the pay is more than what you could ask for. You'll train for two weeks and then for the next two we're evaluating your performance. For the whole month, we'll be paying you a very handsome stipend. Then if you're hired permanently, we'll pay you the full Sunset salary."

I pull my hand out from hers abruptly and don't bother with a single word more before walking straight out of the room. I don't stop as I hear her calling out my name behind me.

Did this damned woman just try to hire me as a whore in the guise of a waitress?

As I'm walking out absolutely livid and growing angrier with every step, I see Lola from the corner of my eye. It takes her ten seconds to learn from the look on my face that things went south in the interview.

"Cassie! Wait!"

Punching the downward arrow button next to the elevator repeatedly, I am struggling with trying to grasp what just happened. Just as Lola catches up to me, the elevator doors close and I sigh in relief about my close escape. I just want to go home.

~

It's been a month since that waitress interview took place. I have thankfully not run into Lola since then and I'm glad that she has not forced me to meet her since she can see I'm not responding to her texts or responding to her calls. Her last text to me from a week ago read "Call me when you want to talk. I hope we can meet and sort this out," with the hug emoji.

I wonder what I will even say to her. The fact that we are best friends and she kept this part of her life completely hidden from me is both saddening and impressive. She left her barista job in her freshman year two years ago, and has been working as a "special" waitress since then.

I'm not surprised that Lola would get a job like that. From what I know, she has always been highly sexually active and with her looks, it is impossible to think otherwise. She has a Scorpio type intensity to her that is so magnetic and overwhelmingly sexual even when she is dressed in the most plain clothes. Well, plain for her anyway. Joi Lansing could never look boring even in a hoodie and sweatpants.

The problem right now is that I need the money. And what Jovanna said about working on my confidence could not be more true. I really do have to come out of my shell and practice being attractive and comfortable at the same time to continue to be this way in the future.

A couple of hours after my classes for such good pay, with Tuesdays and Thursdays off, sounds like a fantastic offer. I don't want to think of this as prostitution, this is primarily waitressing with a little extra, that's all. There'll be a uniform and trays to carry, and cleaning involved. And then the sex. It's not even like sex is the main part of the job...plus it's not like I don't want to have sex. And I'll get to practice being comfortable in a very hands on way and it's all going to be perfectly safe.

It's going to be super new and exciting, what's there to lose? But I also wonder if I have lost the offer because of the way I walked out on Jovanna...

I pick up the phone and decide to talk it out with Lola again.

~

After talking with Lola, I decided that I will take up the job. All my worries were put to rest when I met Jovanna again who was thrilled to have me on board. We immediately discussed the details of our contract and she was extremely helpful and patient with me as she explained everything in detail and reassuring me of my safety.

Later, she asked me to meet at the main diner after closing hours and I found that all the Sunset staff was there. It was a small welcoming party for me and I genuinely felt comfortable there. I met all the bodyguards and the IT members who monitor the security cameras, along with the ten Sunset girls, all of whom were stunning. I even met Richard, who is extremely attractive not just for his age but could put young men to shame with his physique. It was there that Jovanna informed me that Richard would be the one guiding and training me for the customer interactions in The Den, which is what they call the secret extension at the back where all of this stuff happens.

Standing in the kitchen, I tug at the bottom of my crop top for the tenth time before I walk towards the door that leads out into the main area in the Den. I just have to get used to wearing clothes this revealing. I pick up the food tray and walk out, being careful not to trip over my baby blue heels. At least I have my jeans on.

"Good evening, Mr. Conti. I'm your server and companion for the evening. My name is Cassie." I put the tray down.

"Good evening, Cassie. You look absolutely lovely. Try smiling a little when you greet me."

I smile at him and he smiles back, as he pushes his silvering hair away from his forehead. His face is so devastatingly handsome, I think I'm starting to develop a bit of a crush on him. I think he knows that too.

He puts a hand on my hip where my thigh gets fleshy. His fingers dig gently into my leg through the denim and I feel myself inhaling sharply at the unexpected touch. He notices it and says, "You'll have to get used to this, sweetie. Customers won't always wait to have small talk before they make a move."

I nod gently, suddenly feeling my cheeks burning up and feeling very self conscious. Richard takes my hand and pulls me closer. With tears prickling at the corners of my eyes, I try to keep a straight face. Why am I so overwhelmed right now?

"Shh, honey. Don't be scared," he says as he guides me to sit on his lap. With his arms around me, he caresses the sides of my upper arm and rests the other hand on my waist.

"I'm only trying to get you to be okay in this environment. It wouldn't really be training otherwise, would it?" His voice gets gentler and softer as it drops into a whisper.

"If it wasn't for the training, I'd only take you in my bed." He moves his head closer to kiss my lips. My tears trickle down from the outer corners of my eyes and I can't help but feel a little stupid about this reaction.

He sucks on my bottom lip and our tongues meet slowly, as if to say hi to each other before he dives in deeper to explore a little more. His hand on my waist has steadily stayed in its place and I wish he would move up to touch my breasts.

Almost as if he could hear me, he pulls his head away and lets me off his lap. Feeling a little surprised at the suddenness of it, I look at him questioningly.

"Pull your pants down." He says sternly.

I look at him pointedly, silently conveying my thoughts to ask if he means it.

"I said, pull your pants down. Now. Yes, I do mean it."

I slowly unbutton my jeans and hook my thumbs on the sides of the waistband to pull it down. Just when I am about to inquire further, he cuts in to answer, "the panties too."

I re-hook my thumbs into both waistbands and pull them down up to mid thigh where his hands stop me. I can feel a string of my wetness get pulled down with the crotch of the panties. With my vulva on full display, I close my eyes to deal with my shame. I shaved about two days ago and I have the beginnings of a mild shadow of dark hair growing through my pale skin.

Richard asks me to step forward and gently brings up his middle finger to touch my cleft that covers my clitoris. He gently probes it to poke at the soft mound and then his finger slowly travels down with slight pressure to part my labia majora. I can feel that his finger detected how wet I already am and I'm sure my face is bright shade of red right now.

"Mmm." He says under his breath as his moves his finger away a little to play with the wet fluid that feels a little thicker the further down it comes from.

I'm no longer trying to hide my deepening breaths that have turned into panting. He's being excruciatingly slow in his movements, almost knowingly. What a tease.

He parts my legs a little so that his hand can comfortably access my opening. Moving his finger, just the one, up and down my cleft, he moves the secretions around which relaxes my inner folds to come out and stay unfurled from their closed confines of many hours inside my panties.

Grabbing the folds with his thumb and middle finger, he tugs a little and makes a little moan escape my mouth. He teases me with just one finger going up and down relentlessly, never quite fully coming into contact with my clit, which is throbbing painfully now.