The Nude Waitress

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A suburban milf makes a deal with a homeowners association.
9.1k words
4.37
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Part 1 of the 6 part series

Updated 06/08/2023
Created 06/19/2016
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The following is based on some real events and my experience. I am new to writing so if this is exciting or interesting let me know. There is much more to my story.

My name is Renee. I'm 37, live in a great neighborhood, have a family and I suppose up until the moment that I became a publicly humiliated laughing stock, my life had been fairly perfect. I was popular in high school, met my husband my junior year in college, started a family and we were successful, happy and respected.

Then came the crash.

My husband, Michael, had made his money in energy and with everything going well, we had felt like we could do no wrong. I was a member of the local school board- my first foray into politics, which I loved- and Michael had put a lot of money into some real estate deals which were going to set us up for good. He had also convinced a number of people, friends, neighbors and the like, that they could do as well, so when the price of oil dropped- and because of that the land values all but vaporized a lot of people's investment- someone had to pay.

Fast forward a year, past the audit that showed Michael had been concealing a few things, past the over reactive criminal charges and the trial, which saw him scapegoated for the actions many others took, past the removal of me from the board even though I had done nothing wrong, to my actually having to get a job. Fortunately since I had also volunteered with our local fire department as a dispatcher, they were able to offer me a paid position. Between that and the receptionist work I was able to get for a real estate group, I was able to cover some basic costs. Then came an unexpected bill from the Homeowner's association.

Five hundred dollars. I frankly did not have it. I called the head of the association, a man I had actually served with on the school board and asked if I could get an extension. At first he was a little rude, probably because he had lost money with Michael's venture. Then as he was talking to me he suggested I come by the office to discuss some options.

I didn't really like the idea, but I was in a lousy spot. I mean if I could not cover this, the homeowners could, by law, actually end up owning my home. I knew this and as nobody was willing to float any kind of loan, I knew I would need to get some kind of allowance or forgiveness.

If I had only known.

Ben Gossage was 55, your stereotypical white, suburban fatcat and a perpetual adolescent despite his chronological age. I had always found him to be a bit of an idiot, especially when he drank which was often, and an almost juvenile chauvenistic flirt. He had a slight balding spot and a waistline he didn't bother to work on at all. I should have expected something hinky when I walked into his office and he smiled like a fourteen year old that had discovered a hole in the girl's locker room wall.

"Hi, Renee," he said sitting back

He had on a polo style golf shirt and a pair of knee length khaki shorts. There was a small bar-be-que stain on his shirt.

"Hello, Ben," I said. "Thanks for meeting with me."

"Oh sure, Hon," he said.

The "Hon" was new. When Michael was around and we were on top, he would have been much more deferential. I didn't bite, though or try to correct him, even though it bugged me.

"Real shame about the financial problems you are having."

I almost thought I saw a kind of shitty pleasure as he offered his condolence.

"But whatever," I thought. I needed to address the problem and I could ignore his attitude. The fact was that I had gotten sort of used to being villainized, after the trial. People I used to know looked at me differently, just certain I must have been "in on it" whatever "it" was and I got used to suddenly not being invited to neighborhood social functions or even being spoken to when I ran into people I thought were my friends.

"Yes, thanks," I said. "Listen Ben..."

"How's Michael doing?" he interrupted. "I bet jail is really some adjustment. He's not having to get in touch with his feminine side is he?"

I couldn't believe the insulting insensitivity of that comment and just stared at Ben.

"I'm just kidding. A real shame though, and now you are having a problem with the Homeowner's fee?"

"Uh, yeah. As I was saying, I will have some trouble with that, but I know in the past we did have some alternative fee schedules and plans."

"Yeah," he grinned. "That's true. I was thinking, you know we had that one family. They really bought in here above their financial station."

He looked at me and added, "Out of their league, being around the folks that really belonged here."

"Uh yes," I said feeling even more uncomfortable, "About that. I was wondering if there was something we might consider in my case."

Ben sat back. He frowned like it was a real problem.

He rubbed his chin.

"Hmmm, yeah," he said like it was advanced mathematics he was considering.

Then he snapped his fingers.

"You know there is something coming up..."

He grabbed the Neighborhood Association events folder and starting thumbing through it frantically. Then I saw his eyes light up.

"You know the Day at the Lake is coming up."

"Yes," I said.

It was a sort of start of the summer play day on the man-made lake at the center of the housing development. It consisted of boating swimming and the like and then the evening was for the grownups to have a sort of cocktail party and light hors d'ouvres.

"Well, you know, we had to pay waiststaff last year. That Mexican woman charged us for her cousin just to walk around with a tray and get drinks and snacks for people."

"Uh huh," I said.

I could tell where he was going. They wanted me to wait on them so they could smugly put me in my place. I took a deep breath.

"Sure," I said smiling my best fake smile. "That would be fine."

"Great! You know I think a lot of people half expected you to move out of here after the thing with Michael, but this is great. Kills two birds with one stone."

"What?" I said.

"You know. You get to stay and we don't have to pay for the "help."

"Uh sure," I said forcing the smile.

It was obvious they were going to "put me in my place" but I couldn't care less. I'd keep my home.

He grinned and then pulled a large contract out of a desk drawer. It didn't occur to me that if he had just come up with a solution, why he had a contract ready to go. Plus it was pretty involved. I was just starting to look it over when he said.

"Hey look Renee, Hon, I have a tee time so I really need you to sign or not sign so I can tell people whether we need to hire staff." He looked at his watch.

I should have read it.

Instead I picked up a pen and signed twice...one for his copy and one for mine.

He stood up and said, "Great, so really looking

forward to Day at the Lake and having you remain in the neighborhood."

And then I was out of there.

A day later is when the impact of what I had agreed to became apparent. I was at the grocery store and two women...mom's whose children knew mine, gave me a kind of droll look and then whispered to each other...looked at me and giggled. I had sort of had it with being the butt of so much social denigration and walked up.

"Hi Candace, Jessica."

It was like a preemptive retort wrapped up as a pleasant greeting. Unlike how things had been when Michael and I were on top socially, the other women were completely unaffected by my attitude.

"Oh, hi Renee. So buying some razors or hair color?" said Candace, a middle aged, short haired-wide-bottomed shrew. You probably know the type. She was okay looking when she was younger, but after a couple of kids, she was not trying that hard to maintain her looks and figure as much. The final acquiescent gesture was cutting her hair shorter so it would be manageable. Giving up on her own looks didn't keep her from resenting women like me that still worked at looking good. And now she could be completely unrestrained in her pettiness.

I frowned.

"What are you talking about?" I asked.

"Now Candace, you know she is probably going to just surprise everyone."

Jessica was your typical, short, body conscious uptight Baptist. She also had an attitude, a kind of half-bitch, half sugar pie fake sweetness that had always seemed so cliched in the burbs. Just then she looked at me up and down like she was appraising something stuck to the bottom of her shoe. Her lip even seemed to curl in a slightly past-life-as-a-sorority-with kind of way.

"I know there are a lot of people who are looking forward to seeing you again."

I just looked confused.

At that, the two of them chuckled and walked off.

Thirty minutes later I was home and reading the contract. I hadn't just signed to serve. I had agreed to a service contract, obligating me to the homeowner's association, inc. for a year's worth of uncompensated (though tips could be applied) work, and obligating me for at least 5 functions... or more... to be determined at the sole discretion of the officers of the association.

That included Candace and Jessica's husband as well as three others, one of which was Ben Gossage. It also stipulated that wardrobe, scope of work, duration and contract renewal would automatically generate annually unless I served a 60 day notice put forth by my legal counsel and approved by the local administrative justice of the peace. If I failed in service to the contract again subject to the sole discretion of the officers of HA INC I would bear cost for compensation, penalties, and all legal processing fees.

I was in a contractual trap.

I picked up the phone and dialed Ben.

"Helloooooo Hon," he said happily.

It was obvious he knew it was me from caller ID.

"Ben, I was just reading over that contract we signed..."

"Oh yeah, it's a doozy isn't it? Candace's husband drew that up. Guess going to law school did something for him."

He chuckled again.

"But Ben, it is an obligatory 5 functions?" I pleaded.

"Oh yeah, you didn't think you'd just have to do the one thing right? I mean you do get to keep tips and hey 5 events...at 100 per brings you up to 500."

I sat there silently for a minute.

"And what is this about wardrobe? Are you expecting me to wear some stupid maid's outfit or something?" I asked

"Oh no, nothing remotely like that. That would be kind of insulting. You are hardly the status of a maid"

I took a breath.

"What then?"

"Not to worry, something casual, I'll have it over to you today. Oh, glad you called. It reminded me that I do need to ask your shoe size."

"I'm a women's 6" I said.

"Okay, writing that down," he said.

"And I wear a size 4."

He almost cut me off.

"Yeah okay then. You'll have it tonight."

He hung up.

That evening at 445 the doorbell rang and my daughter, Lacey, came back with a small box, barely bigger than a shoe box.

"What is this?" I asked.

"The man said someone from the Homeowners sent it over. "

"Is there anything else?"

"No, Mom. Just that."

And she was off to do her homework.

I opened the box. Inside was a pair of thick white slouch socks and a pair of white leather sketchers cross trainers. That was it. I pawed around in the box. The shoes were size 6.

Then I remembered that phrase in the contract about dictating wardrobe and a cold thought entered my mind. With an over whelming sense of dread, I picked up the phone and dialed.

It rang and rang. I looked at the clock. It was almost 5. Finally it picked up.

"Hi this is Ben."

"Ben," I said, " I really need to..."

"Fooled you," it said. "You got my voice mail.

If this important leave a message some context and a number and I will call back as soon as possible. Thanks."

"Listen Ben, it's Renee. I have what was sent over but I really need to speak to you.... Please call me back."

I waited.

And I waited.

And I waited, all the while feeling queasy and trying to convince myself that I had misunderstood. That it was all just an error.

This didn't mean I was expected to..."

At ten o'clock that night my phone rang. I was taking a bath when my daughter walked in and said, " It's Mr. Gossage. He said you asked him to call you."

I took the phone and waited while Lacey left.

"hello Ben?"

A chuckle answered me.

"Hey Hon, how are you doing?"

"Well that is the thing. I, uh, got a package but I don't think I got everything," started hopefully.

"Oh?"

"No," I said.

"Well, okay, what was in it?"

"Uh a pair of shoes and socks."

There was a pause.

"Yeah?"

"Well, is the rest of the uniform going to be at the get together or do I need to get it or what?"

'Actually now that you mention it, yeah you probably will have to provide the rest of it."

"Oh," I said breathing a sigh of relief. "Okay well where should I pick it up?"

"I'm guessing the drug store."

"Sorry?" I said.

"Well, that is where a woman buys skin lotion and razors and whatever she needs to groom and whatever else you do, right?"

"Ben, are you saying..."

I sat up in the tub. He could hear the water sloshing around through the phone obviously.

"You're a smart girl, Renee. And I'm guessing you are in the tub so...yeah already you have on what you'll be wearing to waitress...plus the shoes and socks."

"Ben! I can't do that!"

He chuckled again, but when he spoke his voice was very definite.

"You can and based on the legally binding agreement we have...you will. So just cause I know you want to make a good impression, let me add one thing... I like a little pubic hair, but most of the rest of it shaved. Even the back door okay?"

I couldn't reply.

"Yeah...well good, now you get to grooming. We are all looking forward to seeing you tomorrow night!"

The phone clicked insultingly in my ear.

I sat there numb. It all made sense. The looks, the grins. The comments from those two women.

They were all in on it.

They had set me up. They had me. I couldn't afford court. I couldn't afford to fight. I sat staring straight ahead. On the other hand the idea of having to waitress... nude, in front of people I used to consider peers and equals, was sickeningly humiliating. I thought about all those catty little luncheons I had once been a major player in. I knew how they talked, critiqued, how they delighted in another woman's downfall.

And now they would have the ultimate shot at me. I looked over at the edge of the tub where my disposable razor sat.

Then I reached over and picked it up.

The next morning I awakened to the sound of my kids downstairs getting ready for their day at the lake. I sat up in bed and then crawled out from under the covers. What I saw in the full length mirror stopped me in my tracks. I had groomed myself lying on my back in the tub but now I saw as I stood there that I had REALLY groomed. All I had was a little landing strip of hair that OBVIOUSLY stopped above my lips. In fact standing there I could actually see where the shaving revealed my puss below the edge of dark hair. I gasped and my big breasts shook slightly.

Now I should explain, years before my husband who is a complete breast man asked I was okay with getting an augmentation. I wanted him happy and so I really went with an augmentation. I am slender, 5-4 and 107, and I have 32 DD cups. It's been a few years and they have "settled" according to my plastic surgeon so they kind of, actually bump and bang and move when they are not supported. Only their shape and size give me away as having "fake ones". The idea that everyone that wanted to attend the suaree that night would see what I was looking at in the mirror, just killed me.

I suddenly thought about what Ben had said and what else I had attended in my preparations in the tub the night before and I turned and leaned forward, looking back. The detail that showed back there almost made me faint. In fact I was as hairless back there as the day I was born. I could see every nook and cranny of the area around my butthole and then it hit me that I really I wasn't bending that far forward either, so if that was the view I was getting like this, I could just imagine what would happen if I really did lean down to pick up something. And forget squatting.

I suddenly needed to do something that would make me feel like my old modest, decent self again and I walked to my chest of drawers and got out my very modest mom-kini. It's a kind of tankini with full butt coverage. Once that was on I considered myself in the mirror again. I have fairly short hair, it's pretty blonde... yes, I color it- a fact everyone would soon know. For some reason, maybe because I was still so unsettled by how nude having the more severe grooming made me feel when I looked I needed to keep putting more clothes on. Even though I didn't need it to hold my hair back off my face I grabbed a pink golf cap put it on before heading into the bathroom to apply my make up.

If I had my preference I would not be going to the lake. I mean who knew how many more in the community were in on the plan about me waitressing? But I had promised my kids and it would be too strange to suddenly cancel. So I did my eye makeup just out of habit. I used a kind of smoky liner to make the green in them pop and then realizing I didn't really want to attract more attention, put on a thick pair of sunglasses and headed down stairs to make the best of things.

Maybe it was me but all that day anytime anyone smiled or was even remotely friendly, I became instantly paranoid, wondering, "were they just looking me over knowing soon..?"

I was in the middle of that thought when a cold drop of water fell on my shoulder bringing me back to reality. Ben stood next to me in his swim trunks. I looked up.

"Hey, uh shouldn't you be getting home so you can be on time for your job?"

I started to respond but I could see that there was a kind of slight thickness in the front of his trunks and I bit my tongue.

"Come on kids, " I yelled getting up."

They groused and whined, but eventually came along complaining that none of the other kids had to leave so soon. There was no way I could credibly explain so now I was suddenly the villain with my own children.

The drive home was no less pleasant as my mind reeled with what was coming.

Once there I went into the bathroom to change. It was something of an ordeal as I was about to go do a job in the nude. What exactly does one wear to that, I thought.

After pondering too long, I put on a light pink sweat suit over a thong panty and bra and then I went to the bedroom, sat on the bed and pulled on the tennis shoes and socks. I mean I had no idea what else to wear. I stood up and walked downstairs. The kids were giving me the cold shoulder, which was just as well, so I left the house, climbed back in the SUV and drove over to the homeowners country club which also had an entertainment complex and dining room. It dawned on me that I wasn't sure which category my role fit into.

I was turning into the long drive to the lot when my cell rang. It was my new boss and tormenter, Ben.

"Hell, Ben, " I said, pulling into a space.

"Hey, Hon, we are just about ready to start and I wanted to make sure you were going to show."

I caught the double meaning.

"Yes, I am just pulling up now," I said.

"Oh good," he said sounding a little mocking,

"We wouldn't want you getting into trouble for being late for your first day at work."

"I'm coming," I said.

"Well good, oh, and uh, don't bother using the front door. You'll probably save time by just going to the staff door around the side."

The staff entrance! That was a huge slap in the face, and I knew he knew it. I just bit my tongue and counted to ten.

"Sure thing," I finally said, trying to sound pleasant.

He hung up, but I was almost sure I heard a slight chuckle from another voice in the background just before he did.