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Caddymaster — a series by Openbook
This series stems from the original short story Caddymaster, that was written to tell of the adventures experienced by one young boy in the Connecticut of the early 1950's. One story suggested another, and so, from that simple beginning it started to grow, and finally, without my conscious will, it somehow spiralled out of control to become a long series of stories told about several main characters over a span of more than fifty years. It is a story that follows a young boy from the age of twelve right up to the present, more than fifty years later. The stories are mere glimpses that are taken all along the way to show the many experiences that shaped him and helped to form him into the man that he became.
  Title Description Size Dnlds Votes Score
1

Lenny From Shenny The fifth story in the Caddymaster saga. Jackie's cousin makes a bid to be Caddymaster.
Tags:
Sex Contents: No Sex
Posted:
14 KB 4841 150 6.60
2

I Gave My Heart To You Sixth story in the Caddymaster saga. Jackie's big sister Annie, once again finds love.
Tags: Ma/Fa, Consensual, Romantic
Sex Contents: Much Sex
Posted: Concluded:
24 KB 5602 168 7.25
3

Big Tony Goes Crazy Tenth story in the Caddymaster Saga. Jackie gets called on to come to the aid of Theresa's father. Ellen, Jackie's wife decides to work her own separate agenda.
Tags: Ma/Fa, Consensual, Romantic, Humor
Sex Contents: Much Sex
Posted: Concluded:
42 KB 4188 113 6.90
4

Crossing One of Life's Thin Lines The eleventh story in the Caddymaster Saga. Jackie once again finds himself caught up in other people's turmoil. He learns a hard lesson about what people will do to stay together.
Tags: Ma/Fa, Consensual
Sex Contents: Some Sex
Posted:
22 KB 3325 105 6.84
5

Annie Gets Another Chance Story number thirteen in the Caddymaster Saga. Jackie gets asked to help smooth things over with his parents when Annie jumps the gun on starting her family.
Tags: Ma/Fa
Sex Contents: Much Sex
Posted: Concluded:
31 KB 4989 104 7.18
6

The Ordeal of B. D. Poynton The fourteenth story in the Caddymaster Saga. Jackie gets reluctantly involved when Ellen and Joan set out to undo a Main Line New England family's traditions.
Tags: Ma/Fa, Romantic, Humor, Oral Sex
Sex Contents: Much Sex
Posted: Concluded:
34 KB 3351 94 6.82
7

Coping With An Open Wound The fifteenth story in the Caddymaster saga. Jackie makes the mistake of going against the wishes of his wife and his mother. His father and brother think he's crazy to be fighting this battle.
Tags: Ma/Fa, Consensual, Cheating, Pregnancy
Sex Contents: Much Sex
Posted: Concluded:
89 KB 6477 113 6.56
8

Billy Sings The Blues The Sixteenth story in the Caddymaster Saga. Billy gets Jackie involved in straightening out his mess. Theresa decides she has a way to slow Billy down in a hurry.
Tags: Ma/Fa, Consensual, Cheating, Oral Sex, Pregnancy
Sex Contents: Much Sex
Posted: Concluded:
41 KB 3783 79 6.62
9

In the Family Tradition The seventeenth story in the Caddymaster saga. Jackie gets led by Ray into a new business venture and into exploring some of the family traditions.
Tags: Ma/Fa, Consensual, Cheating
Sex Contents: Much Sex
Posted: Concluded:
83 KB 5131 62 6.49
10

Trying to Keep It Friendly This is the Eighteenth story in the Caddymaster Saga. Jackie and Billy encounter business competition that calls for decisions to be made. as usual they attack their problems directly.
Tags: Violent
Sex Contents: No Sex
Posted: Concluded:
46 KB 2798 68 7.10
11

Fight Night at the El Bolero Tavern The twentieth story in the Caddymaster saga. Jackie makes it to age twenty one, and finds out that there's more to being a man than getting older.
Tags: Ma/Fa, Romantic
Sex Contents: Much Sex
Posted: Concluded:
67 KB 3144 61 7.76
12

Tripping Over Money The twenty first story in the Caddymaster saga. Ray brings Jackie a wonderful opportunity to make a lot of money. with the help of his family, Jackie watches as his hopes all turn to troubles and worries.
Tags:
Sex Contents: No Sex
Posted: Concluded:
75 KB 2621 53 7.34
13

Bunny Rocks the Boat This is the twenty fourth story in the Caddymaster saga. Jackie's cousin finds herself cast adrift by her jealous boyfriend. Jackie trys to heal the rift or mediate a workable separation. As usual, life interferes with his simple plans and hopes.
Tags:
Sex Contents: No Sex
Posted: Concluded:
61 KB 2384 49 7.29
14

Absent Provocation The Twentyfifth story in the Caddymaster Saga. A very young Jackie stands by and watches the dynamics in his family undergo change. Family comes first, but there's always a price to be paid.
Tags:
Sex Contents: No Sex
Posted: Concluded: / (Review)
46 KB 2650 46 6.94
15

Leopards Don't Change Their Spots The twenty sixth story in the Caddymaster saga. Jackie gets drunk in a bar up in New Haven. He arranges a surprise for his father, but it turns out differently than he imagined it would.
Tags:
Sex Contents: No Sex
Posted: Concluded:
75 KB 2660 48 7.72
16

Nipping Trouble in the Bud
Drama
The twenty eighth story in the Caddymaster saga. Jackie and Billy lock horns over who is going to control their business dealings.
Tags: Ma/Fa
Sex Contents: No Sex
Posted: Concluded:
152 KB 3187 75 8.23