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HOME >> Product 0312 >> Wayward Boy>>

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Wayward Boy


Wayward Boy is the story of a recent high school graduate. He's pretty much ostracized in his filthy-rich East coast hometown of Snobville. As a result, he spends much of his time in a small sailboat in Chesapeake Bay doing water samples and tide pool creature counts. As a result, he's known around town as an expert sailor.


The wayward boy is ostracized because his mother married a guy from Baltimore who made a living selling sports cards. People from Baltimore are not well looked upon by people from Snobville, especially one who sells sports cards for a living. The trading card guy is dead in a plane crash and wayward boy's mother has married again, to a mainline Snobville man. The new husband wants wayward boy the hell out of Snobville. Thus, wayward boy will go to a college in California.

Since wayward boy will be leaving and since he knows that he mustn't make waves or he will injure his mother's tenuous social standing in Snobville, the rich ladies of Snobville see the perfect opportunity to get their daughters a bit of sexual experience without any publicity.

Wayward boy is hired to take several Snobville girls who have just graduated from high school out on 'night tide pool adventures.' One at a time, wayward boy takes a girl out in his boat. The 'night tide pool adventure,' of course, will actually be a first sexual adventure for the girl.

A girl's first sexual adventure is a very important thing for the girl. Wayward Boy examines several such adventures from the viewpoint of the boy (and, to some extent from the viewpoint of the girl.)

As the summer draws to a close, he is presented with an intriguing proposal from the final girl who is at the top of the Snobville girl heap….if he accepts it will help his mother's social standing in Snobville.





32648 Words



Sale Price:




Cover Art:

T.L. Davison


W. Richard St. James


R. Richard

ISBN Number:


Available Formats:

PDF; iPhone PDF; HTML; Microsoft Reader(LIT); MobiPocket (PRC); Palm (PDB); Nook, Iphone, Ipad, Android (EPUB); Older Kindle (MOBI);




JUST CALL ME JIM. My story really starts with an unfortunate decision made by my mother almost nineteen years ago.

My mother was a tall girl with a wild mane of honey blonde hair and a sort of wild streak. She grew up along the shores of Chesapeake Bay in a little town I'll just call Snobville. The houses in rich Snobville are mostly large and impressive, with long green lawns. The people in the houses have impressive amounts of another kind of long green. However, money or no, if you lived in Snobville back then or if you live in Snobville now, you have to toe the line if you want to get along.

Unfortunately, Mom didn't toe the Snobville line. Mom came from a family that was first generation in Snobville. For the first couple of generations that a family lives in Snobville, they're considered carpetbaggers. Boys from a carpetbagger family might be allowed to date the daughter of a maid of a proper Snobville family. A girl from a carpetbagger family might just be allowed to date the sons of the proper residents if the girl looks like Mom did. However, the sons would only date a carpetbagger girl if she put out early and often. Mom told me that she had a few dates that more closely resembled wrestling matches. Mom finally told the last Snobville boy she dated that he was a ... Well, I'm not going to tell you what Mom said, but it actually wasn't too ladylike.

After a time as a pretty much complete social outcast, Mom met, dated and married a man who came to Snobville from the big city, Baltimore. The man Mom married was, of course, a carpetbagger. Not only was he a carpetbagger, the man made his living trading sports cards. Trading sports cards can be lucrative, but the Snobville people considered it a step up from pimping. Not a very big step up, but a step up. Now there were people in Baltimore who might have been acceptable to the people in our town. However, not very many and very definitely none who traded sports cards for a living.

After Mom married her sports card trading carpetbagger, I was born. Two years after I was born, my father died in an airplane crash while he was flying to a sports card convention.

Mom was then left to raise me alone.

We had enough money from Dad's insurance and the sale of his sports card collection so that we could live without Mom working. This was just as well, as the neighbours wanted very little to do with Mom after she married a carpetbagger. If Mom had needed to get a job, it would have been working as a waitress or a janitor. Even after her carpetbagger husband was gone, Mom was still socially dead in Snobville.

My childhood years were a bit rough on Mom. We had just enough money to live reasonably well, but not enough for Mom to play the expensive games the locals played.

Mind you, Mom still looked good, damn good. However, no man in Snobville wanted the lady with the outsider's kid.

If you think it was tough on Mom, it was tougher in me. No one in Snobville wanted anything to do with a carpetbagger kid. As a result, I had some trouble early on. However, I was bigger than the other boys my age and the trouble was mostly just social rejection and not too much physical abuse. However, I could see which way the wind was blowing and I took action. I lifted weights and played Kung-Fu at the YMCA. The first time one of the big boys tried to beat up the carpetbagger kid, I kicked his ass so thoroughly that the other guys pretty much left me alone afterward.

By the time I got to Snobville High School, I was tall and muscular and maybe even a little good looking. However, since no one except Mom wanted me, I spent most of my time in a small sail boat on the waters of Chesapeake Bay. I had a job with a research firm doing water sampling, small sea creature counting and things like that. It was an okay way to spend time since I was an outcast with nothing else to do. As a result, I did get to know the little beaches and coves of Chesapeake Bay as few others do.

I have no idea how my life would have worked out if I had decided to stay in Snobville. However, late in my high school career, things began to change. I was a good student and I had hopes of winning a college scholarship. Snobville, including Snobville High School, doesn't need carpetbagger kids. However, they do need kids who can win a college scholarship. The need is not based on money, but rather on the need to show that Snobville kids are not just good looking, but also the very top of the heap intellectually.

I might have just won a scholarship and gone to the school that offered me the scholarship. However, the people who ran Snobville High School saw me as a way to win a big, prestigious scholarship. The big, prestigious scholarship was necessary to show the white trash who lived in nearby towns that, while the law might grant them equality, they're really quite inferior to Snobville people.

Thus, several times during my senior year in high school it was necessary for me to take the bus up to Baltimore to take tests for one big, prestigious college scholarship or another. I did very well with the tests, especially in math, and I eventually won a scholarship to Caltech out in California. My win was proudly displayed in the Snobville Trumpet to show the nouveau riche that they should remember their place when dealing with a Snobville High School graduate.

The last bus trip up to Baltimore was just after I had turned eighteen. After a hectic day taking tests, several of us took a little detour to an area of Baltimore that they call The Block. The Block is an area of bars and strip joints. I was included in the detour trip because, even though I'm a carpetbagger, I'm tall and older looking. Older is good in The Block, because at least some of the places don't admit little kids. We weren't little kids, we were, by damn eighteen year olds from Snobville. However the people in Baltimore didn't recognize our innate superiority and we were forced to resort to subterfuge to get into some of the bars.

We got into this one strip club and found out that there was a contest going on. With my math mind, I figured a way to win the contest. The contest prize was a backstage fuck with one Big Cat Carrie. BCC had an enormous set of tits and a tight, athletic body that let her do the kind of dance that got her called Big Cat. She could also fuck like a big cat and would have brought me off in seconds like the green kid I was. However, it was my first time and I was so nervous that I lasted a while and, for a wonder, even fucked BCC into orgasm and submission.




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