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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.

1 Caddymaster

A young boy experiences some early adventures on his way to becoming a man.
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Sex Contents: Much Sex | Genre: Erotica
Tags: mt/ft, Consensual, First
Downloads: 18775 | Votes: 520 | Score: 6.37
Size: 18KB | 3,662 words | Posted:

2 Cousin Billy and Theresa

The second story in the Caddymaster saga.The further adventures of young Jackie in his torturous journey to adulthood.
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Sex Contents: Much Sex | Genre: Erotica
Tags: mt/ft, Consensual, Heterosexual, Pregnancy
Downloads: 14036 | Votes: 357 | Score: 6.33
Size: 33KB | 6,700 words | Posted:

3 Dancing At The Griswold

Third story in the Caddymaster series. Jackie gets to go to a dance in the Griswold Hotel's grand ballroom.
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Sex Contents: Some Sex | Genre: Erotica
Tags: mt/ft, Consensual, Romantic, Heterosexual
Downloads: 9291 | Votes: 313 | Score: 6.37
Size: 29KB | 5,818 words | Posted:

4 The Blackwell Triangle

The fourth story in the Caddymaster Saga. Cousin Billy's life takes a few quick turns as he struggles to adulthood.
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Sex Contents: Some Sex | Genre: Erotica
Tags: mt/ft, Ma/ft, Consensual, NonConsensual, Romantic, Rough
Downloads: 9977 | Votes: 308 | Score: 6.68
Size: 65KB | 12,868 words | Posted: Concluded:

5 Lenny From Shenny

The fifth story in the Caddymaster saga. Jackie's cousin makes a bid to be Caddymaster.
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Sex Contents: No Sex | Genre: Fiction
Tags: Fiction
Downloads: 6978 | Votes: 260 | Score: 6.50
Size: 14KB | 2,768 words | Posted:

6 I Gave My Heart To You

Sixth story in the Caddymaster saga. Jackie's big sister Annie, once again finds love.
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Sex Contents: No Sex | Genre: Fiction
Tags: Ma/Fa, Romantic
Downloads: 7720 | Votes: 288 | Score: 7.17
Size: 28KB | 5,691 words | Posted: Concluded:

7 The Pleasure of Her Company

This seventh story in the Caddymaster saga. Jackie meets his own first love and finds out that it is better to receive than give.
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Sex Contents: Minimal Sex | Genre: Fiction
Tags: mt/ft, Consensual, Romantic
Downloads: 9289 | Votes: 245 | Score: 7.14
Size: 75KB | 15,110 words | Posted: Concluded:

8 Brooding In a James Dean Way

This is the Eighth story in the Caddymaster Saga. Jackie tries to cope with the loss of his love and with the problems life keeps presenting him.
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Sex Contents: Minimal Sex | Genre: Fiction
Tags: mt/ft, Ma/ft, Teenagers, Humor, Sadistic
Downloads: 7693 | Votes: 245 | Score: 7.57
Size: 76KB | 14,971 words | Posted: Concluded:

9 Ray Ray Rides Again and Again

The ninth story in the Caddymaster saga. Jackie's brother Ray learns some valuable lessons about the kinds of girls he chases.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Ma/Fa, mt/ft, Teenagers, Consensual, Humor
Downloads: 7217 | Votes: 196 | Score: 6.91
Size: 37KB | 7,470 words | Posted: Concluded:

10 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.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Ma/Fa, Consensual, Romantic, Humor
Downloads: 5811 | Votes: 190 | Score: 6.73
Size: 42KB | 8,673 words | Posted: Concluded:

11 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.
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Sex Contents: Minimal Sex | Genre: Fiction
Tags: Ma/Fa, Consensual
Downloads: 4711 | Votes: 171 | Score: 6.59
Size: 23KB | 4,818 words | Posted:

12 Hold Still So I Can Hit You

This is the twelfth story in the Caddymaster Saga. Ellen's family has the crisis this time and Jackie gets trapped into participating in the problems.
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Sex Contents: Much Sex | Genre: Erotica
Tags: mt/ft
Downloads: 5067 | Votes: 171 | Score: 6.45
Size: 13KB | 2,758 words | Posted:

13 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.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Ma/Fa
Downloads: 6479 | Votes: 169 | Score: 6.83
Size: 31KB | 6,172 words | Posted: Concluded:

14 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.
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Sex Contents: Minimal Sex | Genre: Fiction
Tags: Ma/Fa, Romantic, Humor, Oral Sex
Downloads: 4691 | Votes: 149 | Score: 6.74
Size: 35KB | 6,706 words | Posted: Concluded:

15 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.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Ma/Fa, Consensual, Cheating, Pregnancy
Downloads: 8745 | Votes: 175 | Score: 6.58
Size: 89KB | 17,952 words | Posted: Concluded:

16 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.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Ma/Fa, Consensual, Cheating, Oral Sex, Pregnancy
Downloads: 5126 | Votes: 132 | Score: 6.62
Size: 41KB | 8,263 words | Posted: Concluded:

17 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.
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Sex Contents: Some Sex | Genre: Erotica
Tags: Ma/Fa, Consensual, Cheating
Downloads: 7025 | Votes: 110 | Score: 6.47
Size: 84KB | 16,902 words | Posted: Concluded:

18 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.
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Sex Contents: No Sex | Genre: Fiction
Tags: Violent
Downloads: 3972 | Votes: 117 | Score: 6.95
Size: 47KB | 9,294 words | Posted: Concluded:

19 Saturday Night at the Wallflower's Ball

The nineteenth story in the Caddymaster Saga. A young Jackie continues on his discovery adventure and sees different sides of his personality emerge.
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Sex Contents: Some Sex | Genre: Erotica
Tags: mt/ft, Consensual, Reluctant, Romantic, Historical, MaleDom
Downloads: 3950 | Votes: 100 | Score: 6.44
Size: 39KB | 7,920 words | Posted:

20 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.
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Sex Contents: Minimal Sex | Genre: Fiction
Tags: Ma/Fa, Romantic
Downloads: 4307 | Votes: 101 | Score: 7.45
Size: 68KB | 13,624 words | Posted: Concluded:

21 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.
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Sex Contents: No Sex | Genre: Fiction
Tags: Fiction
Downloads: 3715 | Votes: 94 | Score: 7.27
Size: 75KB | 14,935 words | Posted: Concluded:

22 Making Popcorn With The Gordon Sisters

This is the twenty second story in the Caddymaster saga. Jackie's new young neighbors can't wait to experience the same kind of New England hospitality that Jackie's dad gave to their mother, who is also the aunt of their cousin, Clara.
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Sex Contents: Much Sex | Genre: Erotica
Tags: Ma/Fa, mt/ft, Teenagers, Consensual, Humor, Cheating, Slut Wife, First, Oral Sex
Downloads: 5983 | Votes: 96 | Score: 6.43
Size: 70KB | 13,785 words | Posted: Concluded:

23 When the Frost Was On the Pumpkin

The twenty third story in the Caddymaster saga. Jackie and his cousin, Jimmy discover together the adventures to be had every Saturday afternoon at the Bijou Theater.
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Sex Contents: Some Sex | Genre: Erotica
Tags: mt/ft, Teenagers, Consensual, Oral Sex, Voyeurism
Downloads: 4671 | Votes: 84 | Score: 6.55
Size: 69KB | 13,830 words | Posted: Concluded:

24 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.
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Sex Contents: No Sex | Genre: Fiction
Tags: Fiction
Downloads: 3372 | Votes: 79 | Score: 6.87
Size: 62KB | 12,236 words | Posted: Concluded:

25 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. / (Reviews)
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Sex Contents: No Sex | Genre: Fiction
Tags: Fiction
Downloads: 3653 | Votes: 75 | Score: 6.48
Size: 46KB | 9,079 words | Posted: Concluded:

26 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.
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Sex Contents: No Sex | Genre: Fiction
Tags: Fiction
Downloads: 3683 | Votes: 78 | Score: 7.28
Size: 75KB | 15,117 words | Posted: Concluded:

27 At The Sunoco Quarry

The twenty seventh story in the Caddymaster saga. Jackie has some experiences with the kids in his cousin Billy's crowd. He learns not to take everything and everyone at face value.
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Sex Contents: Some Sex | Genre: Erotica
Tags: mt/ft, Consensual, Lesbian, Heterosexual, Exhibitionism, Size, Violent
Downloads: 3992 | Votes: 75 | Score: 6.30
Size: 83KB | 16,598 words | Posted: Concluded:

28 Nipping Trouble in the Bud

The twenty eighth story in the Caddymaster saga. Jackie and Billy lock horns over who is going to control their business dealings.
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Sex Contents: No Sex | Genre: Drama
Tags: Ma/Fa
Downloads: 4278 | Votes: 104 | Score: 8.12
Size: 151KB | 29,810 words | Posted: Concluded:

29 The Challenge

The 29th story in the Caddymaster series. Jackie finds himself faced with an ethical dilemma. Will he give in to his worst side, or will he somehow manage to rise above temptations and do what he knows he should?
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Sex Contents: Some Sex | Genre: Drama
Tags: mt/ft, Teenagers, Consensual, NonConsensual, Reluctant, Heterosexual, Incest, Brother, Sister
Downloads: 5099 | Votes: 101 | Score: 6.66
Size: 81KB | 16,190 words | Posted: Concluded:
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