tagMatureJamie Goes From Boy To Man Ch. 01

Jamie Goes From Boy To Man Ch. 01


I'm dedicating this story to a lady that I will probable never meet, face to face. In spite of this her ideas inspired most of the story line. She will go unnamed but she will know who I'm talking about.

The people in this story all came out of the author's imagination. Any resemblance to real persons, living or dead, is entirely coincidental and was not the intent of the author. All the characters in this story are at least 18 years of age. There are no minors involved in acts of a sexual nature in my story. It is fiction, people. I'm writing it for my own entertainment and I hope for your pleasure as well. So please do not write to me saying that it is unbelievable.

I once got a letter about another story and all it said was "FILTH NOTHING BUT FILTH." The letter was anonymous of course, they always are. I can only picture an old maid, in her 80s. Who has never been with a man in all of her years. Pretty odd when you think about it. If a person feels that way, and she has every right to her opinion, why would she come to a site like "Literotica" and read the stories in the first place? What did she expect to find?

OK I'll get off my soap box. I just wanted to let off a little steam. LOL Time to get on with my story. I hope you all enjoy. BB


It was late Friday afternoon. I just finished my last class and I was sitting alone in the coffee shop across the street from my high school. The day was hot and a nice cold soda was something I'd been looking forward to all day. Besides, the waitress liked me and as long as her boss didn't catch on she would keep bringing me free refills for as long as I stayed.

It was only two weeks until highschool graduation. I had earned a scholarship to UC San Diego but that would only pay for books and tuition. I would have to get a job to earn money for my day to day living expenses. I was going through the help wanted section of the local newspaper and didn't notice her when she can in.

When I finally looked up from my news paper, I could see her sitting across the aisle from me. She was staring at me, and even when I had obviously caught her, she still didn't look away.

She was an older woman, at least compared to me. I guessed in her sixties or maybe late fifties. She was dressed in a very expensive looking dress. Her breasts were large I would guess at least a D+ cup. From what I could see of her legs they were nicely tapered. All in all she had the body of a much younger woman. Her stare moved from my face down to my crotch and her lips turned up a little, to a coy smile.

I have to admit that she was starting to turn me on and I could feel my cock starting to grow hard in my tight jeans.

She must have noticed my obvious excitement, because she ran her tongue across her lower lip and looked into my face with smoldering bedroom eyes.

I felt like a total fool because I was so naive, I didn't have a clue what to do or say. I just sort of fidgeted around in my seat looking down at my hands and every minute or so I would glance up at her and see if she was still looking at me.

She was not only looking at me but she had a huge smile on her face now and her eyes were sparkling. She was almost laughing at me, and I felt even more like an idiot.

Now I set my eyes down and kept them down, afraid to even think about looking up at her. I pretended to be reading the help wanted ads again but I really was not reading a single word.

Then a few minutes later, staring down, I could see she had moved from her table and was standing next to my booth.

"Are you expecting company," I heard her ask in a soft feminine voice.

I looked up into her beautiful eyes and Stammered, "No I, I'm all by myself."

"Well then would you like some company?" she asked in that same soft voice.

I almost choked when I said, "SHU,,, SHU,,, Sure!!!!! I would love some company."

I stumbled over myself as I shifted over to make room for her to sit down.

"You are a cutie," she said as she slid gracefully in beside me, pressing her bare thigh up against my leg.

"Thank you," I said not knowing what else to say, but my face turned beet red.

"Oh my God, you're blushing," she said, "how sweet. You really are adorable, and so young."

At that minute she placed her hand on my inner thigh and turned to face me with a disarming smile.

Since the coffee shop was near empty and the waitress was busy in the back, no one could see us.

I was just starting to grow a hard-on under the table and her fingers were starting to inch their way up my thigh toward my cock.

She knew full well what she was doing and with a touch as soft as a feather she started moving ever closer to her goal. The beads of sweat were forming on my forehead. And I was finding it hard to breathe. But she just chattered away like not a thing was going on.

"My name is Amber," she chattered. "What's your name?"

"Jamie," I gasped, as her finger tips finally reach her goal.

She closed her hand around my cock, measuring its length and girth.

"OOOO it's so big and hard," she whispered in my ear. "I can't wait to pull it out of there and see it in all of its glory." She was stroking me though my trousers, really enjoying her teasing little game.

I was shaking like a leaf in the wind. I pleaded to her, "Oh please miss Amber, if you keep doing that I'm going to blow my load right through my trousers."

That seemed to bring her back to planet Earth, She stopped playing with me instantly. "OH No- No- No, Mommy does not want you cumming so soon. She wants to play with her little man a lot more before she will let her little baby squirt all that yummy cream. I'll tell you something right now, Mommy always gets her way, baby."

Amber let my cock go and slid back away from me in the seat. She took a sip of her coffee and acted like nothing at all had just happened.

I guess she either didn't know or care that I was going to have one Hell of a case of blue balls very soon.

I recovered my composure as much as possible under the circumstances.

After a couple of minutes Amber turned to me and said, "I see you have been looking through the Help Wanted ads in the paper. Are you looking for work?

"Yes ma'am," I said. "I will graduate from highschool in a couple of weeks, and I want to start university in the fall. I have a scholarship but that will only pay my tuition and books. I'll still need more money to live on.

"How about your parents, won't they help you out?"

"My mother and father were both killed, in an automobile accident a year and six months ago. I still have their life insurance, but that still will not be enough."

"You may be in luck, Jamie. I need a strong young man around the house to help with the gardening and performing some other duties." She reached down and squeezed his thigh, so there would be no misunderstanding about what those other duties would be.

"That would be great, but how much would the job pay?"

"Don't you concern yourself about that. I may even have a few friends who would pay you well for your services as well. If you can perform as good as you look."

There was another squeeze on my thigh.

"Anyway we can talk about that at a later time, after I see just how well you can perform."

"That sounds great," I said, "When can I start?" I asked.

"What is the matter with right now, or do you have another date tonight? My car is right outside and I only live a couple of miles from here."

Amber paid our bill and left a large tip on the table. "That is for the waitress having enough sense not to bother us with a lot of stupid service."

With that we were our the door.

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