Diner Girl

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.

"You're right, ok, I enjoyed it," I said louder that I wanted to.

"Hey did you hear me saying it is a bad thing? I mean now that you're single again you can have fun." Jack poured coffee in my mug.

"You never liked my boyfriend." I exhaled noisily.

"He was prude."

"What?! How will you know?" I couldn't believe my ears. "I can't believe about what you're making up your mind."

Jack shrugged. "Forget it."

"Alex was not prude," I exclaimed.

"No?" Jack grinned at me. "So he was experimental? Made you desiring him and all that he had to offer?"

"About what the hell are you speaking?"

"I'm speaking about his qualities, his intellect and also his lap. Both were not overwhelming I guess. You deserve better, that's all I'm saying." Jack took a sip of coffee.

I was stunned. It never occurred to me that he cared about my private live, but it seemed he did. And he did it in an improper way.

"Really Jack. I'm shocked."

"I think not the first time today." Jack grinned and I looked at him. "I have seen you, in the car, in her car," he explained nonchalant. "Hey don't look at me like that. I'm a man. I just wanted you to know, thought it's fair."

"What have you seen?" I demanded.

"Well I looked up and recognized her car. I saw you both in there, thought you were talking. But then you put your feet to the console. I couldn't see what you both were doing but I have a wild guess." Jack tried to surpass a grin.

I was furious. "At least try to be ashamed."

"Why? You're stripping right in front of my diner and want me to look away?"

"I was not stripping for you, Jack!"

"I know, it's a pity."

"What?!" I stared at him.

"Has it ever occurred to you that you say 'What' fairly often?" Jack smiled now. It was a goofy almost shy smile.

"You really would like me to strip? For you?"

Jack tried to be back at his usual aloof manner. "Yeah, I mean you're a gorgeous girl."

I swallowed hard. "Would you also like to touch me?"

"Can we please change the topic?"

"You started it, telling me Alex was prude."

"He is," Jack insisted.

"And you would do better?" I teased him.

He gazed into my eyes. "Bet on it, Tasha," he said in a husky voice. Then I did something totally courageous that I wouldn't have dared a couple of hours ago. I rose to my feet and stared at his lap, straight. I noticed the swelling.

"You are....I mean your..." I mumbled.

"Hard?" he helped me out. "Because I think about how hot you might be? How wet she made you in that car?"

I stared at him but couldn't really fix him. I felt arousal rising. I felt my face glowing, my blood pulsating in my ears and vulvar.

"Than show me how you would do it." I heard myself saying. "Here, right now."

Jack looked at me. Then he stood up, still looking at me and switched of the light. He unzipped his jeans in front of me. The bulge in his shorts was amazing to me. He rubbed it slowly. I rose from the chair and his hands wandered under my skirt, finding their way to my panty. He turned me around and pressed his erection against my butt. I started to massage him with my cheeks. I felt his hand from behind sliding into my panty and massaging my wet centre. I lifted one leg to the chair in font of me.

"How wet and horny you are," he moaned as he pulled down my stockings and panty and inserted two fingers at once into me.

"Shhh, just do it."

"As you please." I felt his fingers removing and instead the tip of his cock between my butt cheeks. "Do you like it here?" he asked and I felt his cock at my anus. In order to answer I let my butt circle. I really wanted him to fuck me. I tried to lift my butt a bit higher to make my vagina reach his cock.

"I love that you're so lustful," he said. Then I felt something strong stretching my pussy.

"Oh good, Jack." I was so aroused that I felt my pulse in my head.

I felt him inserting his full length into me. Slowly he removed his dick, but not entirely only to thrust it in again. With every thrust into me he became faster and harder. With a free hand he reached for my clit and started massaging it gently. Suddenly he withdraws his penis entirely. I turned around in disbelieve.

"Honey, I would love to come in you longing pussy, but don't you think I would make a lousy dad?" With these words he turned me around again. I wanted to protest. His dick wasn't very long but massive. Again I felt his dick on my anus. This time he pressed harder until he was inside. Very slowly he moved forth and back.

"It's not your first time?" he murmured.

"First time a man does it," I managed to say while enjoying his strokes. I loved how filled he made me. Because he replied nothing I said, "I like my dildo there now and then."

"I always thought you're adventurous."

He reached around my hips and introduced two fingers to my cunt.

"You're unbelievable hot and wet," he whispered. I felt slightly embarrassed but my arousal helped me overcome it quickly.

"Please do it a bit harder," I begged.

"At your service." I could figure out his grin behind me. Immediately I felt him massaging my butt harder with his dick. As he came he gave me final real deep slam. Then he removed his dick from me, but not his fingers. He inserted a third finger and started to fuck my cunt harder. It only took me a few more moments before I climaxed.

"Good girl, hot girl," he whispered.

"Strong diner boy," I replied and smiled.

After we had adjusted our cloth again we sat down to finish the coffee.

"Did he ever pleasured you this way?" Jack asked. "Outside the Sunday morning bed-routine?"

I had to roll my eyes. "Yes Jack, you were amazing, ok."

"What I wanted to say is, a man has to give a woman the pleasure she wants, she deserves." He flashed me his aloof Jack-ish smile.

****

The mysterious woman hadn't come to the diner for a couple of days. This didn't mean I had forgotten the whole incident. To the contrary, I remembered very well that she had made me so horny that I wanted Jack to do it to me, nasty. Unlike his often bad-mannered behavior he was a gentleman regarding this. I had expected him teasing me to no ends about it, but he didn't say anything.

And suddenly the lady in black appeared in the diner. It was already past 8 pm and Jack and me prepared to close.

"Sorry lady, no sandwiches anymore today," Jack greeted her.

"Coffee?" she tried and looked at me.

"Ok, I'll prepare us fresh one," Jack sighed as if it was asked too much to get coffee in a diner.

"May you want to sit down?" The lady said to me. I watched her for some seconds before I sat opposite her. She wore black. The only real color was her auburn hair and her brown eyes. She gave me a half-smile.

"Say do you would be interested in earning more money?" Well, she was a person to come straight to the point.

I looked down at the tabletop and then managed to look at her. "What do you want?"

"I would like you to invite to a party."

I looked at her waiting for what was coming next. I could well imagine that it was no ordinary party.

"Well, you would have to strip, at least." I knew it.

"At least?" I looked into her eyes.

"You strip and get 100 Dollar. For every extra service you may like to provide you get extra payment."

I inhaled. "Ok, I'll strip, but no extra services."

She bent over the table. "Like the no extra service you gave me in the car?" she whispered into my ear.

I swallowed. My heart started beating faster.

"Ok, I'll pick you up here, Saturday at 8.30 pm. Is it ok for you?" she said.

I just nodded when Jack came with the coffee. He looked at me. "You want to?" I nodded again.

While Jack went to the counter to bring another cup the woman smiled at me. "My name is Kate and yours, honey?"

"Natasha," I said. "Just call me Tasha."

"Fine, Tasha."

We drank the coffee in silence and after this Kate left.

"What were you talking about?" Jack wanted to know.

"She invited me to her party," I said.

"What kind of party?" Jack pushed.

"Just a party."

"C'mon Tasha."

"I'm going to strip on her party, ok? I get 100 Dollar for it."

"Girl!" he exclaimed. "I mean we can speak about you salary, you know that, don't you?"

"It's ok Jack."

The older man surveyed me and a smile crept over his face, a dirty smile. "It really turns you on, right?" Now his smile was a big toothy grin. "I always thought you're kinda adventures, but this astonishes me."

"What?!"

"There's your 'What' again.

Kate arrived precisely at 8.30 pm at the diner. She looked stunning. This time she wore a cream-colored trouser suit and a white blouse with quillings and a bow tie.

"Hey darling, you look great," she greeted me. Jack gave me a slap on my butt, reminding me what he did with his dick a couple of days before.

"You look awesome in that suit," I stated as I walked over to Kate.

She glanced at me and raised an eyebrow. "Thanks honey."

We drove in silence for a while. I looked over to Kate, wondering what would happen tonight.

"I have changed the plan, hope you don't mind," she started. She gave me no chance to reply. "I don't want you to strip. I want you to take off your panty, but not your nice fishnet stockings. You just party with us and keep the folks guessing. Show them what they want to see, ok?"