The Nude Waitress 05

I'd been instructed, actually ordered, on what to wear. Deb, it seemed had a type. She liked her potential bedmates to be ultra-feminine, liked blondes and liked them meek and submissive. In short... me. I had arrived as ordered in a moderately short - slightly below mid thigh - sundress that was casual but cute, and with wide shoulder straps but a low-enough neckline that while modest, if I leaned over wrong, would give no doubt that I was braless underneath.

Just like with the party at Arnie's I had felt like a slutty party favor, a sex object, dedicated to one thing only, the degrading service of another's fantasy and satisfaction. This time however, it was different. I was being served up by women to a woman and the dynamic, as I walked around the gathering was palpable.

There is a phenomenon among a gathering of catty women that is known as a pecking order, in some cases when it is overt enough it is even known as a hen party. In those situations, a woman, lower in status, is figuratively pecked by the other hens emotionally. It can get quite devastating. There are even sex parties where "henning" will take place and the lower hen gets stripped and is expected to sexually satisfy the rest of the brood. My situation was not quite that bad, but I could tell when I walked in that everyone there except for Deb was in on it and that Deb was immediately interested.

Like a laser, she zeroed in on me and made her way over for an introduction. Jessica was only too happy to oblige. As we shook hands and exchanged those ridiculous pleasantries I saw smirks, whisperings and derisive mocking glances from the other women who knew exactly what I was going to have to do.

It didn't take long for things to escalate. As I had been instructed I bent over to pick up a champagne flute filled with frozen bellini and as I did caught Deb unapologetically looking right down my top.

I also noticed that the others had moved a bit away to give her whatever privacy she required to make the next move.

"You know, uh, Jessica told me that you and I have something in common," said Deb.

"Oh, and what was that," I asked realizing how intensely Deb maintained eye contact.

"She said we had certain similar interests, and that you had asked about me after seeing my picture."

So there it was. They had told her that I was interested. Now I had no choice, but to further that fantasy. This was about to be an even lower level of behavior than I had anticipated. I wasn't just going to have to eat her out and go utterly lesbian submissive in bed. I had to act like I had a crush.

I forced a smile to my lips.

"Well, it's embarrassing being outed that way," I said. "I, uh, don't have a lot of experience."

That last part was absolutely not a lie.

"Maybe I'll just take control and instruct you on a few things then?" she said.

I swear at that point she could have licked her lips and the meaning would not have been more apparent. At a distance I saw Jessica and Candace whispering intimately and I died a little as I kept smiling ridiculously.

"You know I have a home here in town. Not in the neighborhood, but uh, maybe we could head over there and get to know each other better."

There it was. I might as well have showed up at her hotel room door and said I was "from the agency."

Then she leaned in and whispered, "If you live up to your billing sweetie, I think I might just end up in love."

I smiled and downed the bellini in two greedy, but necessary swallows. A second later, we were walking out to her car, a huge Cadillac Escalade. As I climbed up on the leather seat, a breeze lifted the hem of my skirt giving a brief glimpse of my thong. It was not lost on Deb. Almost the second the door was closed she leaned over, placed a hand on my bare thigh and kissed me passionately on the lips. It caught me completely by surprise, but almost hearing Jessica's voice in my head, I returned the kiss as an odd sense of reluctance and disempowerment washed over me.

"I've been wanting to do that from the second I saw you," said Deb.

"Oh, uh wow that is so flattering," I answered still completely off-balance.

"It's okay. Jess told me you have just been intensely bi curious, but had not found someone you wanted to explore that with up to now."

"Oh, uh she did?" Just then I could have strangled Jessica. She had more than set me up.

"Don't worry, when we get finished, all your curiosities will be satisfied," chuckled Deb.

"That's great," I said lamely. I was so far in over my head.

"Yeah oh and Jess also explained that you are also a part of, well, a part of a certain... deal."

"She did?" I said.

"Yeah, she said you do some entertaining on the side, but that I am your first, female client."

I just looked at her with that clueless, vague, go-to smile on my face that I used whenever I was in shock.

"In a way I guess that makes you kind of a virgin," laughed Deb.

That seemed to be a delicious concept for her.

When we arrived at her place, it was clear to me that I was riding with someone who had spent her life never failing to get her way. The grounds were lush, tropical and immaculate, as we passed through the exterior gate, I had the feeling I could have been with some Vegas mogul who just happened to like having her pussy licked as with a Florida real estate heiress. The house, I saw as we pulled up the long drive, was easily 5000 square feet and built like a Mediterranean villa; all open courts and pool decks and tall glass windows.

She parked the car and climbed out. I did the same and we walked up to the front door. I waited as she started to put the key in the lock and heard her say in an almost off-hand way, "Go ahead and get naked now."

"Sorry?" I said, realizing we were still outside. Secluded perhaps but cars were driving past the gate and could see in.

She glanced at me and smiled.

"Strip."

I swallowed hard and for a second considered saying something. Then, hands trembling slightly, with a watchful eye at the gate, I reached back and unzipped the dress. It fell and I stepped out, now in just a little white novelty thong with the words, "Your special gift" printed on the front.

It had been Jessica's idea. Apparently it delighted Deb.

"Take that off too... and hand it to me, my little pet puss."

I took a breath and then pulled it down, stepped out and handed it to her. I was bare-assed naked outside the house and somehow I knew this was not the most depraved thing I was going to have to do.

Deb then opened the door. I was just stepping inside, a little too quickly as I was already feeling really embarrassed and wanted inside the modesty-protection of the house, when she reached over and firmly grasped my left nipple and areola stopping me.

"I didn't say you could go in yet, did I?" she said and slowly tugged on my nipple, milking it.

My eyes widened in surprise as my nipple reacted between her fingers.

"Did I?" she repeated.

"No," I said.

She gave me a critical look.

"No... what?"

I could have died. She was on a power trip.

"No ma'am," I said softly.

It was music to her. She chuckled softly and let my nipple go, but not before she upped the ante a bit.

"You know, I really like it when someone who needs something from me acts like it and you, need me to go through with property term deal for Jess, right?"

"Yes," said.

"Yes..."

"Yes Ma'am," I said.

"Good, so uhm...how about... you get down on all fours and crawl into the house?"

I looked at her then, really shocked. She just smiled. After a moment's hesitation I lowered myself. I got down and with my huge tits hanging obscenely and my shaved asshole and pussy on display to her, crawled across the threshold to the cold marble entry way.

"Lovely," she said. "You are going to do just fine."