The Nude Waitress 03

You know, you never feel more nude than when you are crouching inside a fake cake waiting to pop out in front of a group of drunken, horny men.

This was my first "real" assignment after waitressing at the neighborhood center and being Ben Gossage's assistant for a week, one marked by either a daily blowjob or a humiliating rear entry fuck across his desk. Of course the rest of the time I was in a too small tennis outfit without a stitch of underwear so whether I liked it or not I was continuously flashing an upskirt or showing off two involuntarily, air-conditioning hardened nipples to anyone that looked my way.

It had just been the day before that Ben had walked in with that overly delighted smile on his face that told me immediately that something humiliating and sexually dirty was coming my way. As it turned out he had hired me out for the second in my five contractually obligated tasks.

"Why are you smiling like that?" I asked.

Ben sat down behind his desk and his grin spread even farther as he said, "Well, I have some news."

I turned slightly toward him with my legs tightly together, trying not to show my half shaved pussy.

"And?" I asked.

"Well, tomorrow evening you have a little gig," he said.

I swallowed hard and felt a burning blush rise in my face.

"What do I have to do?"

Ben kind of chuckled.

"Well you know Arnie Hendershaw?"

"Yes," I said remembering Arnie, a 50 something horndog who had been going through a year-long divorce with a former stripper trophy wife. Before my husband had been railroaded on the stupid financial fraud charges, Arnie had been one of those people with whom we had socialized, not so much because we liked his company, but because he owned a bunch of car dealerships and was something of an important, if offensive social player in our community. He was also, in reality, a 15 year-old juvenile delinquent in a 50 year-old body, a real chauvinist and patriarchal dumbass that I always found staring at my chest or legs when he thought I wasn't looking.

"Wellllllll," said Ben, "His divorce finalized and his friends are throwing him a little welcome-back-to-the-world-of-the-sexually-living-happy-divorce party."

"Okay," I said uncertainly.

Just then the a-c kicked on and my nipples stood out like super thick Thanksgiving turkey timers. I crossed my arms defensively to hide the reaction, but Ben was already staring.

"Oh man," he chuckled ridiculously, "Seeing that never gets old."

I blushed even more.

"So, as part of his party, his friends felt it would be a lot of fun if the entertainment were equal to his situation," he continued.

"Entertainment?" I said, getting a terribly uncomfortable feeling.

"Oh yeah, you know. Like say a really big ol' knockered gal popping out of a cake in her birthday suit."

My jaw dropped. It was beyond a nightmare scenario. Ben busted out laughing at the horrified expression on my face at the idea of having to pop nude out of a fake cake in front of one of the biggest pervs I have ever met.

"Oh Ben, no," I whined. "You can't be serious. Not Arnie!"

"Are you kidding?" said Ben. "Of course. It's perfect. Who better? I mean the past queen of the neighborhood. Ms. out-of-his-league showing it all off for good old Arnie? What a way to say Happy Divorce?"

He laughed again at the supposed genius of the idea as I sat there with a completely horrified and disgusted look on my face, arms and legs crossed defensively. The idea of having to salaciously display myself like that for him... I felt my face burn with an even deeper humiliation.

"So, you know, you will probably want to make sure you trim and shave up nicely down there," grinned Ben looking at my lap. "You want to make sure and give a good impression. They are paying for a show after all."

"A show."

The words escaped me in a kind of breathy desperate whisper. Somehow that one word brought the humiliating reality home in a new and devastating way.

"Yep. Needs to be a good one too. You know, titty shaking, big smile, look like you are happy as pudding to be there showing off. Be sure and give him a good look from all angles too. I mean they are paying a lot for this."

With each word the expectation hit with ever more horrifying gravity about what I was going to have to do.

"All angles..." I said vaguely, like I was drowning in a lake of prospective shame.

"Oh yeah, you know what I mean. Face away, bent over, legs wide apart, then, you look back and smile. That sort of thing," said Ben. "We want them to all know they got their money's worth."

I was so trapped and I knew it. There was no getting out of this and yet, the idea of having to display and degrade myself with such a lewd performance was too awful to bear. Ben on the other hand was having a ball considering it.

"Hey," he said, bringing me out of my fog of contemplation. "How about you practice here first?"

"Oh come on, Ben," I groaned.

"Yeah, I'm serious," he said becoming more excited. "Stand up and take off your top and skirt."

Almost numb, I stood up and reached down to pull my top up and over my head.

It was a size too small anyway and without a bra, it hauled my big boobs upward only for them to slip out and drop heavily bumping against each other. The shirt cleared my head and left my thick blonde hair with a tousled disarrayed look.

Ben stared greedily at my tits with their nipples at full temperature aligned attention.

"Damn, your surgeon was a fucking god," laughed Ben, and then almost as quickly said, "Okay now the skirt."

I reached down and pulled the elastic band down over my hips revealing a small black furry landing strip that even standing up showed that it abruptly stopped right above my clit and labia.

"Whoo hooo that is fucking nice," he chortled.

I dropped the clothing on my small desk.

"Now squat down on the other side of the desk and when I say 'surprise' jump up with your arms in the air and give those big mamas of yours a nice shake."

Looking like I could kill him I knelt down and felt a gust of a-c right hit me between my spread cheeks, right on the shaved area around my asshole. A second later Ben said the magic word, "SURPRISE" and I jumped up with my arms outstretched. As I landed my tits banged and bobbled.

"Give those girls a nice shake, hon," encouraged Ben.

I shook my shoulders and felt the obscene anatomically thudding result.

"Oh yeah, that is great," he said. "Don't forget. Bigggggggg smile."

I forced a beaming, dirty, Miss America smile onto my face.

"Perfect," he said. "Now turn around and spread your legs, and bend over at the waist."

I turned, knowing just how intimate a look he was going to get and leaned forward presenting my bald, nude crotch for review.

"Oh fuck that is so bad, " he laughed delightedly. "And now, hold it..."

I held the position.

"And now, look back over your shoulder and SMILE," he said.

I turned my head with that same fake smile and saw exactly where Ben's eyes were trained. I could have been cross eyed for all he would have known. Finally, after a year it seemed, he looked up from my perineum at my face.

"Oh you got it," he said and then he looked down at his own crotch. "And uh you got something else started you need to come fix now."

I straightened up and walk around the desk, big tits wobbling. I knew the drill. So did Ben. It was one of his favorites.

He already had his pants undone and his big fat cock was already out pointing toward the ceiling. He pushed the chair back and in the too familiar, really demoralizingly ritual, I crawled under the desk.

A minute later I had his big cock in my mouth, bobbing rhythmically on it as I slurped and sucked away. He was groaning luxuriously already with his insistent hand on the back of my head, pushing me deeper with each suck until I had to consciously relax my throat to take this dick to the limits of my gag reflex. Even so he was big, and I reacted and gagged slightly as he pushed me deeper.

"Oh fuck you suck cock like a goddamned Hoover vacuum," he gasped as he started a kind of mild thrusting with his hips, that I knew meant that his orgasm was not far off. I clamped my lips around the shaft and extended my tongue against my lower teeth to really rub the under side of his big bulbous head. It was a sure way to drive him crazy and get this over with quickly.

"Oh Jesus," he rasped and then tensed hard.

Just like I expected the first thick nasty salty splash hit me right in the back of the mouth. I swallowed knowing that if I didn't the next shot would make me choke. To Ben's utter delight, with his dick buried in my oral cavity, I sucked and swallowed, draining his big old balls yet again.

Finally, when he was done he shoved me back, bumping my head on the underside of the desk.

"Oh sorry," he said. "It gets so sensitive after, that just makes me go crazy."

"Uh huh," said wiping my mouth as I crawled out from under the desk.

I walked back around to the other side and pulled my ridiculously inadequate outfit back on as he watched and tucked his softened hose back in his pants.

"Uh, hey why don't you go ahead and take off early. I am sure there are some preparations..."

I looked at him.

"I mean, there's girl stuff I am sure you have to do. Nips and tucks and shaves and plucks," he laughed. "You know, so you are all ready for tomorrow."

"Uh yeah. Sure," I said happy to have any excuse to get out of there.

"Oh and you know Arnie is kind of old school, so maybe make your hair kind of big, and do that smoky eye shadow thing," he said.

I looked at him like I wanted to slap him, because I did. Basically, he was telling me to slut up my look. Of course I had just sucked the man's cock so, I really couldn't say much. I just nodded and walked out into the sunshine.

I exited the office, and before I realized it, a sudden breeze lifted my skirt dangerously. I knew that anyone driving by would have seen cheek, but there was not really anything I could do about it anymore than the rest, so I just felt the color flush my face again and lived with it as I walked the rest of the way across the parking lot to my car.

That evening I did exactly as I was instructed. After a long bath, I trimmed and edged my little bush. Then I spread my legs overly wide so I was doing a horizontal version of a cheerleader's splits and worked the razor, smoothing up the already shaved areas so that it was all like silk. Of course the entire time I did my dead level best not to think that it was all in the greater service of showing off gynecologically to the biggest male chauvinist asshole, I knew. Finally, when I was done, I got out of the tub and poured myself a glass of wine that by volume was actually two servings.

Ben had called while I was in the bath and left a message telling me that I should sleep in the next day and not worry about coming into the office at all. He also said he would meet me at my house to take me over for the party and that all I needed to do was to be ready.

In retrospect I wish I had gone in anyway. Having a whole day with nothing to distract me and knowing what was in store that night was far worse. By noon I was already a humiliated and nervous wreck and as is often the case, I thought maybe having a glass of wine would help. By three in the afternoon I was tipsy, and by six I was buzzed and when I had done my hair as ordered and put on a sultry heavy eye shadow, I was in that kind of morally and sustainably foggy state that I had read about in a bunch of stripper blogs. I was in the "this will help me get through this" zone.

I stood in front of a mirror looking at myself made up and coiffed, stark naked with all but a two- inch wide, four-inch tall strip of my pubic hair left and realized what I truly looked like. The word was, milf, I suppose, but in this case I truly looked like the milf stripper. On a certain level my heart broke a bit. I started to tear up out of shame at what this next step in my public humiliation would mean, but knowing what that would do to the eye make up, I simply downed another glass of wine and pulled on my little pink cotton sweat suit to try and make the best of it.

A few minutes later I heard Ben's car pull up followed by the ring of my doorbell. I picked up a pair of sunglasses, and jiggling ridiculously under the sweat suit walked downstairs to the door. As I opened it, I knew, even with this on I had to look as invitingly slutty as I imagined.

He stared me up and down like a kid at Christmas and then his face broke out in a huge grin.

"Oh my god," he said. "This is perfect."

We walked over to his car and in a snarky little move, I thought, he walked around to my side to open my door. It was so gentlemanly, so unexpected, for a second I allowed myself to indulge the fantasy that maybe he wasn't as big a jerk as I thought. Then just as I stepped into the passenger side I felt his hand pat me on the butt.

From my place, it didn't take long to get to Arnie's house. Despite the bite the divorce must have taken, he still had his big sprawling home with its large entertainment area. I had been there before, and as we pulled into the driveway packed with moderately expensive cars, I couldn't help but feel that somehow what was coming would be so much less degrading if it weren't at a location that reminded me of my previous social stature. Then again no one was asking me what I preferred. This was all just about making Arnie happy.

We got out and walked into the house. I could smell cigar smoke and hear thumping music and male laughter as Ben steered me in the opposite direction toward a huge kitchen. As I walked in I saw that there were cases of beer and liquor sitting out and a whole spread of food that looked like it had already been worked over. I glanced at it thinking about the hors d'oeuvres I had nibbled a couple of times at parties in this very house. I didn't have long to consider that though.

Beyond the far end of the bar sat a medium-sized, fake cardboard cake, with an open panel on the back side. Inside was a very small plywood perch with very limited headroom beneath a cardboard lid. It was then that the full gravity of what I was about to do hit me. I was going to have to get nude, and crouch in a tight little ball as they wheeled me out and then pop up and out. I also realized that to get into that position I was going to show off the most outrageous view of my vagina and anus to whomever closed it up behind me.

I was still considering the awful reality of that when I heard Ben say, "Okay well, guess it's showtime."

Almost numb with dread, I peeled off the sweat suit bottoms and stepped out almost reflexively. Maybe it was all the wine, maybe I had just accepted my new station...my social position, but right after that I also unzipped the top and took it off.

Just like that I was nude. Then I looked at the interior of the "cake."

It was going to be even more of a contortion than I expected and at first I didn't think I could get in. I tried once and all I could get in was my lower half. Then I tried starting in head first and did the whole ass up thing much to Ben's delight. Finally, I realized I could squat and if I kept my knees wide apart so my boobs hung between my thighs, I could waddle into the little space.

I don't even want to imagine what that looked like from behind, but it worked. A second later I felt the back panel close up and wadded up with my head between my knees, I felt a slow rolling sensation as the cake was wheeled in.

I could tell we had left the kitchen because, all of a sudden, a louder, thumping musical beat shook the sides of the fake cake. From outside I could hear cheering male voices at what was obviously the appearance of the cake. We rolled a little way farther and then I felt it come to stop just as the music shut off.

"Okay boys," I heard Ben say. "You know our good friend Arnie has been going through a real "dry spell" lately."

A chorus of laughter followed that before Ben went on.

"And well, we all wanted this to be really special for our good friend. I mean no ordinary cake would do. It had to have a creamy filling, that was nice to look at, great tasting and easy to spread?"

Another explosion of dirty laughter erupted. I wanted to die.

"So we thought, what would be better than something... or someone that Arnie has always licked his chops over?"

A veritable howl arose.

"And so, if we could have some appropriate music, I give you, my good friend Arnie, the very sweetest of treats and a genuine wish for a Happy Divorce and... Surprise!"

That was my cue. With a hard shove I stood up against the cake lid and popped out with both arms reaching skyward and a big smile on my face. At the same time that old fashioned song, "the stripper" started playing. I looked around, shaking my chest like I had been instructed and what I saw looking back was almost too much for me to maintain that fake happy entertainer expression.

Seated around the room on chairs, the couch, all around were several middle-aged men. Many of whom I knew from my former life as a respectable wife and mother. Now I was standing, exposed from the thighs up and shaking my huge tits like some ridiculous stripper.

For a second no one said a thing. They all looked as shocked that it was me as they were at seeing the intimate details of my body.

Then Arnie of all people ended the moment.

"Holy fucking Palominos," he yelled. "It's Renee! And she's fucking naked!"

Somehow his stating that I was naked. Him using that word about me almost broke me right then and there. I actually stopped shaking my tits and the smile on my face turned to a kind of frozen fake look. In a weird way I think the fact that I was kind of reluctantly doing this came through and somehow made it even more fun for them.

"Oh no, baby," he said. "Don't stop shaking those big Hooters. Your jailbird hubby paid a lot for those things so let's get all some use outa them."

This broke whatever spell of suspension existed and the men in the room began chanting, "Shake, shake, shake."

I didn't want to, but one look at Ben and I knew. I resumed with the same undignified wobbling, and bumping as all of those men watched with a kind of dirty delight.

"Oh fuck, Ben," yelled Arnie, who was obviously several beers into the event already, "This is perfect. Hey, please tell me she is giving lapdances."

"Oh yeah," said Ben loudly. "Of course the gal needs money so she works for tips."

I looked horrified and my smile wavered. No one had said anything about lapdances. A second later two men appeared next to the cake offering a hand so I could step out. I took each and swaying a little, climbed down into the living room.

The music had changed to something more modern and as calls for me to "give us a dance" echoed I started shimmying and moving in time with the music. This just got them even more worked up. Uncertainly I looked over at Ben who gave a little twirling sign with his finger indicating I make that most degrading move.

I thought I would scream, but instead I took a deep breath and turned, facing away from them, right in front of Arnie. Swallowing hard, I leaned forward at the waist. From behind, I heard a couple of gasps and then the filthiest laugh of my life. It was Arnie.

"Oh my fucking Christ," he yelled. "I bet that thing tastes like French vanilla ice cream."

It was the worst timing as I saw Ben indicating I look back at them and smile. I did.

I couldn't have anticipated what I saw, but apparently Ben's comment about tips had been received. Half of the men were holding up dollar bills. In contrast, Arnie was holding up a twenty. I stood up and walked over to him.

He was already leaning back in his big armchair, with a filthy grin and an apparent erection in his cargo shorts.