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

Caddymaster A young boy experiences some early adventures on his way to becoming a man.
Tags: mt/ft, Consensual, First
Sex Contents: Much Sex
Posted:
18 KB 13678 330 6.34
2

Cousin Billy and Theresa The second story in the Caddymaster saga.The further adventures of young Jackie in his torturous journey to adulthood.
Tags: mt/ft, Consensual, Heterosexual, Pregnancy
Sex Contents: Much Sex
Posted:
32 KB 10289 226 6.33
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.
Tags: mt/ft, Consensual, Romantic, Heterosexual
Sex Contents: Much Sex
Posted:
30 KB 6739 196 6.38
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.
Tags: mt/ft, Ma/ft, Consensual, Romantic, NonConsensual, Rough
Sex Contents: Much Sex
Posted: Concluded:
65 KB 7429 202 6.74
5

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 5017 160 6.56
6

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 5760 180 7.25
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.
Tags: mt/ft, Consensual, Romantic
Sex Contents: Much Sex
Posted: Concluded:
75 KB 7136 156 7.28
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.
Tags: mt/ft, Ma/ft, Teenagers, Humor, Sadistic
Sex Contents: Much Sex
Posted: Concluded:
75 KB 5747 157 7.69
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.
Tags: Ma/Fa, mt/ft, Teenagers, Consensual, Humor
Sex Contents: Much Sex
Posted: Concluded:
37 KB 4805 129 6.98
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.
Tags: Ma/Fa, Consensual, Romantic, Humor
Sex Contents: Much Sex
Posted: Concluded:
42 KB 4323 123 6.87
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.
Tags: Ma/Fa, Consensual
Sex Contents: Some Sex
Posted:
22 KB 3437 115 6.78
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.
Tags: mt/ft
Sex Contents: Much Sex
Posted:
14 KB 3655 110 6.61
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.
Tags: Ma/Fa
Sex Contents: Much Sex
Posted: Concluded:
31 KB 5119 113 7.08
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.
Tags: Ma/Fa, Romantic, Humor, Oral Sex
Sex Contents: Much Sex
Posted: Concluded:
34 KB 3453 102 6.80
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.
Tags: Ma/Fa, Consensual, Cheating, Pregnancy
Sex Contents: Much Sex
Posted: Concluded:
89 KB 6659 120 6.50
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.
Tags: Ma/Fa, Consensual, Cheating, Oral Sex, Pregnancy
Sex Contents: Much Sex
Posted: Concluded:
41 KB 3885 87 6.58
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.
Tags: Ma/Fa, Consensual, Cheating
Sex Contents: Much Sex
Posted: Concluded:
83 KB 5246 69 6.45
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.
Tags: Violent
Sex Contents: No Sex
Posted: Concluded:
46 KB 2889 76 6.91
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.
Tags: mt/ft, Consensual, Romantic, Reluctant, Historical, MaleDom
Sex Contents: Much Sex
Posted:
39 KB 2849 63 6.49
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.
Tags: Ma/Fa, Romantic
Sex Contents: Much Sex
Posted: Concluded:
67 KB 3258 68 7.62
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.
Tags:
Sex Contents: No Sex
Posted: Concluded:
75 KB 2717 59 7.26
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.
Tags: Ma/Fa, mt/ft, Teenagers, Consensual, Humor, Cheating, Slut Wife, First, Oral Sex
Sex Contents: Much Sex
Posted: Concluded:
68 KB 4571 64 6.43
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.
Tags: mt/ft, Teenagers, Consensual, Oral Sex, Voyeurism
Sex Contents: Much Sex
Posted: Concluded:
68 KB 3575 56 6.61
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.
Tags:
Sex Contents: No Sex
Posted: Concluded:
61 KB 2485 54 7.16
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.
Tags:
Sex Contents: No Sex
Posted: Concluded: / (Review)
46 KB 2737 52 6.76
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.
Tags:
Sex Contents: No Sex
Posted: Concluded:
75 KB 2750 53 7.50
27

At The Sunoco Quarry
Erotica
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.
Tags: mt/ft, Consensual, Lesbian, Heterosexual, Exhibitionism, Size, Violent
Sex Contents: Some Sex
Posted: Concluded:
85 KB 3066 50 6.51
28

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 3307 80 8.13
29

The Challenge
Drama
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?
Tags: mt/ft, Teenagers, Consensual, NonConsensual, Reluctant, Heterosexual, Incest, Brother, Sister
Sex Contents: Some Sex
Posted: Concluded:
82 KB 3908 73 6.82