The Nude Waitress 02 - The New Position

This a continuation of the real story of what happened to me. I was a well-respected, married, wife and mom with a beautiful, expensive home in an exclusive neighborhood, living a great if indulged life until my husband was found to have embezzled some funds. Suddenly with him "gone" I was faced with certain debts and a choice; sign a binding exploitative service contract with the homeowners association that has made me a sort of local adult entertainment go to. This is the next chapter.

Naked Waitress: The New Position

The next morning, I awakened to the irritating, intrusive buzz of my cell phone. I had been so distraught last night after the "gig" that I had gone home and drank a tall glass of scotch.

Or maybe it was three.

Regardless, it had been enough that I had apparently barely enough ability to get completely undressed before crashing in bed. Now as I groped for the phone, I realized from the sudden blast of the air conditioner, that I had slept butt naked... except for a pair of socks and tennis shoes, on top of the covers. The responding goosebumps on my buns were even more of a wake up note than the vibrating phone. It also reminded me that had anyone walked in on me like that they surely would have found the odd wardrobe, however little there was, completely bizarre.

"Hello," I said with the groggy tone that only the hungover can produce.

"Hey, Hon!"

It was Ben. His delighted, and really loud voice was not what my throbbing head need to hear right then.

"Just wanted to tell you what a huge hit you were last night. EVERYONE is talking about you waitressing."

It just drove home what a disgrace I had made of myself and I pulled the bedspread across my bare bottom and pussy more because of the resurrecting embarrassment than the cold air. I think I groaned into the phone.

"Hey listen, I need you over at my office this morning. We have some things to discuss and it just can't wait."

"Come on, Ben," I started to complain.

"Hey, now," he said boisterously, "Don't forget the agreement you signed. You owe me a lot of gigs and I have some thing we need to discuss, right now."

I knew he was right. I groaned and put a hand to my head. Ben just chuckled.

So get that cute little butt over here, right now," he laughed.

"Okay," I said helplessly.

"Oh and remember, need you in just those little white tennis and socks like last night."

I think I groaned again, only now as much out of concern that I was about to have to be naked in front of a group again as anything else."

" 'Course probably wear that little sweat suit on the drive over. Don't want you getting busted for indecent exposure..."

He hesitated.

"Well, you already are BUSTED," he laughed.

I didn't reply.

"Hustle on over now..." Then his tone changed slightly to something like insistence. "...and I mean now."

The connection clicked off.

I set the phone down and crawled out of bed. The change in posture just reinforced that I'd had too much to drink as my head throbbed. After a second, I went into the bathroom and turned on the shower so it could warm up while I brushed my teeth. I was just picking up my toothbrush when I caught a good, well lit look at myself in the mirror. I almost gasped at how truly bad, the image staring back at me seemed.

To just get to it, I looked terrible. My eyes were puffy and the little bags underneath stood out like small pillows. Now I'm 37 and - yeah like all women - I have some bagging there, but this was much worse than normal. The makeup I had worn the night before, had rubbed off so I saw myself, stark naked, in my completely natural state. A night of heavy drinking, without makeup and with my hair looking crazily bedheaded, was not pretty. Now, I know some guys like that "used, tousled look", but as the subject of it, I wasn't happy. It hit me that I looked like some stripper, the morning after.

Then it really hit me, I had... nude waitressed. In a way, I knew I was exactly that. I brushed my teeth quickly and realizing I had already wasted time, and didn't want Ben getting upset, I jumped into the shower and rinsed off as fast as I could. I stepped out and dried off then, ran a quick brush through my hair.

There really wasn't time for a new application of makeup, so I grabbed a pair of sunglasses. Back in the bedroom, I started to grab a bra and panties, because that is what I normally wore, but then remembered his comment about just my uniform. I tossed the garments back the chest of drawers and grabbed my tennis shoes and socks

Then I pulled on the pink sweat top and pants. I was just turning to leave the room when I got another look at myself in the mirror. It was bad, slutty bad. My big boobs were obviously braless, hanging a bit lower than normal and the outline of my knobby nipples was so evident. When I moved my boobs wobbled and bumped in the sweat top obscenely. And the bottoms, I could just guess showed the cameltoe that meant NO panties. I couldn't take it and quickly stripped down and pulled on a bra and thong panty and redressed. Still silently bemoaning my luck, I hustled out, down the stairs and out the front door.

A short drive later, I pulled up in front of the homeowner's property management building where Ben officed and jumped out of my car. I opened the door and stepped in just in time to see Ben holding his office phone. He placed it back on the cradle and looked at his watch.

"Took your time getting over here," he said.

"Sorry, Ben, I had to jump in the shower," I said reflexively.

A second later I wished I hadn't.

"Oh ho," he chuckled. "Well, should have told me. I would have come over and washed your back."

I smiled weakly. I didn't like it, but there was no way I could risk making him upset.

"And maybe your front too?" he chuckled.

I just smiled.

"You said you needed to talk to me," I said changing the subject.

"Oh yeah. Hey look you were such a huge hit last night that I've already had three offers this morning. One was a group wanting a caddy...looking like you...built like you...dressed like you were last night... for their round of golf."

I think my jaw must have literally hit the floor when he said that because a second later he was laughing, right in my face it seemed.

"Thought you might not be up for that one. Still," he said like he was offering me a good deal, "lots of fresh air... and you can work on your all-over tan."

I just stood there. It was just too horrid an idea. Especially now, after the experience from the night before, I knew how degrading, it would be. Caddying nude for men that used to be our neighbors and friends, who used to show respect, but now, had seen me...nude... and bending over showing my shaved pussy and anal area. Men who would be intent on seeing it all again only now under the blazing illumination of the sun. The realization hit me like Ben's fat limpid cock smacking me wetly across the face.

"Please, no." was all I could manage. I think my knees even buckled a little.

He looked down at his phone, apparently scrolling messages and email. From the look of it, he'd had lots of feedback on me. I wanted to scream and run out of there, but too much was at stake now. He looked up with a big grin on his face.

I could tell by the look on his face, he loved me begging. I didn't contemplate on that too long as I was desperate not to end up on that golf course in the raw.

"Please?" I repeated.

It was obviously music to his ears. His smile widened.

"Wow, you really don't want to caddy, do you?"

"No," I said. "Please Ben, I have kids, I can't go on the golf course naked. I'll be seen by too many people."

He nodded like he was being understanding. Then he smiled and said, "Of course, you do owe me, and you do kind of have to do what I decide, right?"

"Yes," I admitted helplessly.

He acted like he was thinking it over.

"You know what might help me make up my mind?"

I was way beyond calling him on his fake understanding and deliberation. I just went along.

"What?" I asked.

"If you were butt naked while I thought this over."

There it was. Debase myself in private or be out in public naked again.

I started undressing.

He watched with a kind of delighted expression as I took off the pink sweat top, pulled the pink sweat pants off so that I was standing in front of him in a mismatched thong panty and white underwire bra. Then seeing that look and "knowing my place now" I reached back and unhooked my bra, slipped it off and then unceremoniously pulled my panties off and stepped out of them. I set the pile of garments on a chair in front of his desk. Now I was naked, facing my new boss, completely vulnerable, with no pride allowed at all as I awaited his judgment.

He looked me up and down like a fat kid looking at eclairs through a pastry shop window. The difference was that this fat kid could reach through the glass anytime he wanted. I couldn't help but notice that his eyes lingered a bit longer on my large breasts and then on the groomed bit of dark hair on my mound that was such a contrast to the very blonde 'do on my head.

He seemed to be on the verge of deciding something when his phone vibrated. He looked at it and his huge smile widened even more until it finally bubbled over with a loud chuckle.

"Tell you what," he said, "I think it would be out of line for me to make this decision by myself. After all you did sign your service agreement with the subcommittee of the Homeowner's board. As such I need a subcommittee mini quorum, involved if I am going to follow the rules."

I shifted uncomfortable. That didn't sound good at all; more people with me standing around nude.

"I really should get a couple of their opinions and determine what direction to take this. "

I just stared at him. He started typing a text and then a second later got a reply. He laughed again.

"Perfect, we can have a couple of them here in just a few minutes."

At that I started to reach for my clothes. Just as my hands were about to touch the material Ben cleared his throat.

"Ahem..."

I looked over at him.

"Let's just leave those there. Have a seat."

I had been right in the first place. He wanted to humiliate and expose me some more. With a sinking feeling, I sat down in one of the cheap office chairs in front of his desk. The cold vinyl was so apparent as it made contact with my bare bottom. A second later the air conditioning kicked on again. Instantly I again erupted in gooseflesh. Ben grinned and started texting some more. I was being set up again. I knew it. And worst of all there was nothing I could do, but take it. No matter how bad it got.

I didn't have long to wait to see how bad. At the sound of the big car pulling up at the front of Ben's, I turned my head. I think I actually gasped and I know my heart sank as I recognized the custom grill of Candace's Cadillac through the tinted window. A second later the passenger door opened and I saw Jessica get out. They were both wearing tennis dresses and visors. I couldn't help, but think that not so long ago, I might have been included in the invitation and might very well be on my way to tennis with them. Now I sat stripped waiting for their judgment about more potentially devastating exposure.

As they walked up it, they looked like they were in an excited, great mood. They had obviously found the promise of Ben's text message and my dilemma well worth changing their plans.

I turned and looked back at Ben who had the same errant schoolboy look he had seemed to wear ever since I signed that damnable contract.

"Oh good, they're here," he said.

My eyes popped.

"Ben they are not on the board!" I protested.

Ben just grinned as the door opened.

"No, but their husband's are AND they gave them proxy power on certain matters... you know, for times like now when they are out on the golf course needing a caddy and someone has to make a board decision."

"That's right," came Jessica's voice from behind me.

"In fact in really any matter regarding your... service agreement..." It was Candace speaking now and she almost guffawed as she said the words, "we are the definitive voice of..."

"Authority," finished Jessica.

"So basically these two carry all the swing votes with whatever decisions there are to be made... in particular, about you," said Ben.

He let that sink in a second. They all did with these awful, expectant, have-the-answers-before-the-question-is-asked expressions on their faces.

They could make me do whatever they wanted, wherever and in front of whomever they wanted and I had no power. They waited until the reality had settled with me. When I guess my own expression was sufficiently traumatized and hopeless enough, Candace cleared her throat.

"So what is the matter before the board," she asked looking me, up and down judgmentally and then lingered happily on the pleading expression on my face as I sat there... naked and at their mercy.

"Well, it seems we are getting some requests for some... I guess you would call it service or entertainment by our girl, Renee here," said Ben.

This just energized Candace and Jessica in that peculiarly cruel way that women have when they have a former rival under their high heel.

"Oh well, let's see what her options are," said Candace.

Ben started scrolling and as he did they reacted with more and more mocking enthusiasm with each possible "job" they read. Worse even, they read them aloud for my own emotional trashing.

"Ohhhhhh, that is wild. Nude caddying!" laughed Jessica.

"Yeah," said Ben slightly adjusting himself under the desk. He wasn't quite subtle enough. All three of us noticed.

Both women then looked from his obvious penile fumbling to me with a condescension that communicated wordlessly, "Uh huh, this is what you've come to, a source of arousal for guys like Ben Gossage."

I looked away which just made them laugh.

Then I heard Candace squeal slightly with delight.

"Oh man," she laughed, "Here's a good one. Someone needs a 'stripper' to pop out of a cake at a divorce party."

I reacted firing an outraged look back at them both.

"I'm not a stripper," I said and a second later realized how pathetic that sounded after what they had seen me do the night before and how I was sitting there butt naked in front of them now.

"Oh honey," said Jessica laying it on thick, "Of course you aren't, you're the wife of a felon and an almost felon yourself and and lets not forget a nude waitress."

"Want to add defaulted on a contract and bankrupt single mom in the projects to that?" asked Candace.

It was a verbal sting slap that simultaneously shut me up and put me in my place. There was nothing I could say. I folded my arms across my chest, but not before a twinkle gleamed in Jessica's eye.

"From the looks of things the potential sort of has you turned on," she said elbowing Ben as she indicated my hard nipple.

"I'm cold," I said defensively. "I am sitting right in the stream from the air conditioner."

Candace smiled.

Yeah it is kind of chilly in here. I think we should give old Renee and her big fake tits something to wear so she doesn't freeze to death while we decide her fate."

And with that she walked out to the car. A second alter she strolled back in wearing a HUGE smile and holding an outfit.

"Here you go," she said and held out the garment. I looked at it and then frowned. It was one of those microfiber tennis tops, with the golf style collar and a matching tennis skirt. Unfortunately, I realized immediately that this was one she had bought for her 14 year-old daughter.

"Oh come on," I said.

She just kept smiling, though now it had a kind of harder quality, bitchy even.

"Put... it... on," she demanded.

I stood up, naked and saw them all look me over quickly as I took the top. It was too small. So small in fact that when I finally did get it on....it was overstretched so that the shape and even the slight difference in skin hue of my thick nipples and medium sized areola were obvious through the straining material. Worse yet, the bottom edge of the top didn't reach to my hips, but instead was like a halfie shirt from the 80s, hanging away from my body, just a few inches below my boobs.

"Oh that is priceless," laughed Jessica. "Now the skirt."

I took tennis skirt expecting to find a skort, you know skirt and undershort combo, but apparently this wasn't that...it as just a skirt with a loose, pleated flair that I knew would make it too easy to fly up. The look on my face when I realized that must have really been something, because both women busted out laughing and Ben looked like he was about to have a heart attack. I stepped into the tennis skirt, briefly flashing the shaved lips below my very groomed patch of bush. I pulled it up to normal waist height and realized that even though her daughter was almost as tall as me, when the top was at my waist, the bottom of the skirt was dangerously too far up my thighs. And with no brief under, even the most innocent of moves could wind up flashing my pussy. So, I pulled it down so that the hem was at mid- thigh. This meant the top of the skirt was right above my hip bones. It wasn't "low rise," but just not quite the right enough fit that it suggested something bimboish.

It was just what those two witches intended.

I stood there looking like some big boobed, milfish, pseudo-sportster and had to take the looks on their faces that ranged from outright satisfaction at my new "state of dress" with Jessica, to mocking glee with Candace to a sort of near adolescent gawking from Ben. I could have crawled out of there, I was so mortified.

When they had finished enjoying my emotional distress Jessica and Candace turned to Ben and made like a little huddle. It was clear the women were doing the thinking and talking, but the stupid delighted grin that spread across his face let me know something awfully bad was being cooked up.

Finally they turned back around.

"Well, as the subcommittee of the board we have decided we might allow you one of two choices as regards your contractual agreement," said Jessica.

The stilted semi-legal, half assed formality of her wording struck me as both mocking and pretentious.

"You can either caddy today in the altogether... and run the risk of anyone and everyone seeing you: neighbors, a school bus..." She let that sink in horribly. "Other mom's from your kids' school, your... coworkers..."

I think I looked like I was about to throw up. I sure felt like it.

"Or," she continued, "You can take a slight adjustment in your agreement and we'll let you entertain at Jerry Rangel's divorce party. Of course to make up for it, we think Ben could use some administrative help with his busy schedule so... you'd quit your current job and start working here with him, every day."

"I take the second option," I said too quickly. There was no way I could go out and caddy naked.

"Uh, uh, uh," said Candace, her eyes glittering with a little too much enjoyment at my desperation. "We have to vote on whether to allow you a choice."

I stood there in my ridiculous outfit, with my huge boobs so obviously hanging braless and heavily nippled and the too short skirt not long enough to keep the a-c from gusting up under, against my labia, and awaited the dragging out of my fate.

"I vote for caddying," said Candace cruelly.

I almost gasped.

"Well, I vote for the divorce party and you becoming Ben's admin," said Jessica.

They turned to Ben. I looked at Ben. Ben looked happier than I have ever seen him.

"Well, it's a big decision," said Ben , like he was having a hard time making up his mind.

I could tell this was something they had put him up to when they had been in their nasty little huddle.