I consider myself a lucky girl. I'm from Russia but managed to study Politics at a local College. Another lucky thing in my life is Jack and his diner. I earn enough money at Jack's diner to pay all my expenses. Well, often Jack gives me extra allowances and gives me time off to study for exams. Jack is good soul.
"Great tip," I said one day as the last customer left the diner.
"Yeah, next time you should wear a skirt and you get even more, I bet," Jack replied.
"What?!"
"Your ass, she stared on your ass," Jack answered in his casual manner.
"Would you please tell me what you're talking about?"
Jack sighed. "Every time you went to bring her a new refill she stared on your ass," he explained as if it were a normal matter.
"Oh brother," I groaned.
Jack grinned suggestively. "Oh sister, more likely."
On the way home I thought about the strange customer. She was dressed in a black suit that gave her the elegance of a businesswoman. Her face with the strong cheekbones was framed with shoulder length auburn hair. I guessed she was the same age as Jack, probably end thirties or early forties. She had stared on my ass? I wasn't willing to believe it, but I had to admit that would explain the five Dollar tip.
Next day she was there again. Whenever she ordered more coffee Jack would give me a faked innocent grin.
"Dirty old man," I hissed.
Again I got five Dollar of tip. Yesterday I smiled at her for the generous gratuity but this time I stared on my purse. What if she was really staring at my backside?
When she left Jack's grin grew even bigger. "Hey nothing to be ashamed of Tasha. Your ass is gorgeous, no wonder she's staring."
I must have looked bewildered. "Do you also stare at me?"
"Me? No way honey! Would never dare."
Great, my boss was staring at my back. Until now Jack was no sexual being for me, he was just Jack. Of course I had noticed that he was still handsome. His hair turned grey but he still looked athletic and in his eyes sparkled this boyish rogue. Was he really looking at me that way?
The next morning I was standing in front of my closet. I couldn't help but thinking about Jack's comments. Actually I was no girl for a skirt, but I possessed one outfit, which included a skirt. I hadn't worn it since my boyfriend for whom I had bought it had left me. It was a denim skirt, fishnet stockings, heavy boots and a tank top.
"Wow. Now I have to gaze at you, sorry not my fault," Jack greeted me. "You look terrific." I rolled my eyes in mild annoyance.
This morning I noticed Jack looking at my from time to time. I had to admit to myself that I liked it. I was a little shocked by the thought that I liked Jack staring at my ass and legs. I was much more shocked and embarrassed that I was disappointed the lady in black wasn't coming for lunch today.
In the afternoon I couldn't concentrate on my studies. My head was filled with puzzling thoughts as I realized I just had worn sexy outfit for another woman. Well the idea of woman was not new to me, but dressing slutty to turn on a woman was very new. I sighed. "C'mon that's not slutty, many girls wear cloth like that," I mumbled while tuning pages of my book.
Next day I decided to give it another try and was lucky. The lady in back was there. Now I realized that she was openly roaming my body. She smiled at me. "You know that you look good, don't you?"
I blushed and looked for Jack, but he was nowhere to be seen.
"Ok, would you bring me some more coffee?"
I nodded and went to the bar. I came back with a can of fresh, delicious smelling black liquor. Just as I had started pouring the coffee into her mug as I felt her hand on my butt. My heart skipped a beat. Did she really have her hand on my butt cheek? She grinned at me.
"Thanks sweety, that's enough for now."
I went back to the bar and shook my head. What had I gotten myself into?
This day I got ten Dollar of tip.
The next day I had evening shift. I was almost glad, because the strange woman always appeared for lunch. So I was confused when she appeared at around 8 pm in the door of the diner.
"Hey, I saw light and thought you're open. Do you have a sandwich for me?"
"Sure," Jack said. "Sit down, I'll prepare it."
Jack was famous for being grumpy. Jack being courteous was new to me. I shrugged. "Coffee?" I asked the woman.
She gave me a flashy smile. "With extra sugar please."
"Say, you're a student, don't you?" the stranger began.
"Yes." Normally I wasn't short spoken, but I felt awkward in the presence of the older woman.
"So you need money?"
"Yes."
"Is your boss paying well?"
"It's ok."
I swallowed as I returned with coffee to her table. I had to think of what she did last time and couldn't help but look at her hands. She must have figured out, cause she smiled at me.
"Did I told you already how sexy you are in this dress?"
I sucked in air, tried to appear cool. "No you don't."
"Well you look sexy, gorgeous indeed."
"Thanks." I tried a smile, but failed.
Suddenly I felt her hand on my left thigh. "These fishnet stockings make you look very delicious." I could feel her hand slowly running up my thigh under my skirt and to my ass. My heart raced, I looked for Jack but couldn't see him. Where was he? I panicked. I couldn't move or say anything. I only felt her hand running higher, her fingers slightly brushing the crack of my ass trough my panties. I managed to turn away. Never before I felt so ashamed and yet so exited. I realized that I was aroused.
Jack came back. "Hey I was searching for the tomatoes," he said apologetic and handed me the sandwich. I swallowed hard and went back to the table with the lady.
"Do you wanna sit?" she offered. I just nodded and did so.
"Would you like to earn additional money?" she asked.
Without thinking I answered. "Sure."
She wrapped her full lips around the sandwich and took a bite. "What are you ready to do?"
"I'm not sure what you mean."
"I would like to watch you."
I laughed, "This is for free."
"So you would take of your skirt, stockings and panties for free?"
"Hell, no!"
"We're getting closer, don't we?"
"I would not strip at all."
"Not even for 50 Dollar?" I considered it for a moment, 50 Dollar was a lot of money. I was afraid where this would lead. I could still feel the moist between my legs and the warm tickle that her hand had caused. Why actually not stripping? She was just a woman, an attractive woman I had to admit. I felt little afraid but told myself that she couldn't rape me, right?
I bent over the table and spoke low. "Ok, I will do it for 50 Dollar."
The lady in black surveyed me with a knowing look. "I'll wait in my car. You can come there after you closed the diner." With these words she continued concentrating on her meal. I rose to my feet. Did I really just agreed to strip for money?
"Hey Tasha, what where you talking with her?" Jack asked casually.
Before I could answer I must have blushed to a nice tone of pink. Jack raised his hands. "Ok ok I don't wanna know."
"Just small talk," I tried to assure him.
I was more than a bit nervous when I left the diner. I looked out for the lady in black. It took me a while because it was already dark. Then I saw her in a Landrover. I went to the car. She opened the front door for me.
"Now?" I said nervously while climbing on the front seat.
"Now strip," she said with a smile but some force in her voice.
I lifted my skirt and tried to pull down the stocking and panty.
"Put your feet on the dashboard, sweety," she commanded me. I did so and my heart pounded fast while I exposed my butt and crotch. "Now spread your legs a little more." Also this I did. "You sure look sexy. Nice little haircut you have." Not for the first time today I blushed. I was not shaved but had my pubic hair cut short. I felt arousal growing while the woman looked at me fairly close. I tried to breath normally.
"You're hot honey," she said and smiled at me.
"No!" I exclaimed.
"So the swollen labia and the wetness is your normal condition?"
I swallowed, also not for the first time this day. Our eyes met and a devilish grin spread on her face. She reached down to my crotch. I was shocked and didn't know if I should flinch or lift my hips.
"I really like that," she said in a now throaty voice.
To my pleasure and jolt she inserted a finger into my pussy. I could feel how easily her finger slid into me. I closed my eyes and felt her finger slowly massage me inside my hot pussy.
"You're a real sweet horny girl," I heard her saying. I jumped.
"No I'm not!"
"Calm down. Sure you are. Nothing to be ashamed of." She said while removed her finger from my wetness.
"Now here's your money. Extra service deserves extra payment." I looked puzzled at some banknotes she was handing to me.
"What are you looking, girl? You've done a good job, here's the money." Breathing heavily I pulled up my panty and stockings, then took the money. I wasn't sure what I had expected. I was still shocked that she had fingered my pussy. I also was shocked that part of me regretted that she weren't willing to make me climax.
Standing on the street again I realized her car leaving though the dizziness in my head. Still I couldn't believe what had happened. I didn't even know the name of this woman and let her pet my pussy really deep. I looked at the money in my hand. Oh sister, and she gave me 80 Dollar for doing it.
I saw light in Jack's diner. Some casual talking with the aloof Jack would sure cool me down.
****
„Hey honey, you're back, something wrong?" Jack looked at me, but not worried.
"Uhm no. I just have forgotten my...uhm..." I swallowed. Of course I had nothing forgotten.
"Sit down Tasha, I brew new coffee, if you like," Jack offered. I was surprised by the gentle gesture from him.
"Sometimes weird things happen," I said.
Jack looked over at me while preparing the coffee. "What do you mean?"
"This woman, she really confused me." Now this was the truth.
"I've seen that."
I leaped inwardly. "You have seen what?"
"C'mon, don't you think I've seen were her hand was and how you enjoyed it?"
At least he hadn't seen us in the car, this would have been embarrassing, me with my pants down, heels on the dashboard, my pussy so exposed. The tickle came back to my abdomen. I felt how wet I still was.
"I have not enjoyed it, ok?" I replied and managed to put some sternness into my voice.
"Oh, did I overhear you screaming for help, Tasha?" This dirty grin was back on his face. I looked down at the table. Jack stood up and brought the coffee.
