Dogleg Left, Dogleg Right
Chapter 1

Caution: This Sex Story contains strong sexual content, including Mother, Son,

Desc: Sex Story: Chapter 1 - Two single moms, one private golf club development. Tracy, 32, mother of Rip, 14. Happy, 32, mother of Haley, 14. A horny boy. A horny girl. Although a girl with a difference. Tracy and Happy, two best friends. Rip and Haley, two best friends. Virginity is afoot. For a while anyway. Two unconventional mothers, two horny kids. Sex is in the air. Oh, did I mention the mothers are even hornier than their children?

Jessica's contribution:


The Whispering Pines Golf Club, not to be confused with Myrtle Beach's Whispering Pines Golf Course, is located in Northern Florida, just off the Gulf and just South of the Panhandle.

The private club, founded with what in Florida passes for old money, was established on October 29 of 1930. Exactly one year after the stock market collapse.

The two cofounders -- Richard (Rip) Thornton and Haley Stevenson -- declared the club was one big "Fuck You!" to Wall Street, New York, assholes, yankees, and just about everyone else not born and raised in Florida.

Their money -- Rip and Haley's money -- was earned the old fashioned way. By inheritance. Sugar.

Whispering Pines was more than a golf and tennis club. It was first and foremost a luxury housing development. The two men were visionaries. They realized that proximity to the beaches, niche-marketing golf and tennis to their rich friends, business acquaintances and (after much deliberation) snowbirds, would turn cheap, available scrubland into valuable homesites.

They weren't selling houses, they were selling lifestyle. Your neighbors were bankers, doctors, lawyers and the top tier of business professionals. Business would be done on the best-designed golf course in Northern Florida.

Business would be done in the bars, between tennis sets, in the restaurants. Business would be done.

Women -- wives, daughters, girlfriends, mistresses -- were allowed full access to the entire facility. The reigning undercurrent at WP was fun. The annual Club Championship trophies would be hotly contested. As would big money wagers on the course and on the courts.

But, for the most part, WP was a relaxed, easygoing place to unwind, enjoy cocktails during Prohibition, smoke Cuban cigars, dance the Charleston.

The WP homes were on two to six acres. The first houses followed the contour of the course, which had been designed with the residences taking precedence over the links.

Over the years, gently curving streets were added to accommodate houses that were further and further from the course. Eventually automobiles were restricted to the outer roads. Every WP home had several golf carts and this anti-car philosophy too was ahead of its time.


Fast-forward a couple of generations. The founders' granddaughters -- Tracy Thornton and Happy Stevenson -- lived in their families' original homes near the 10th (Tracy) and 18th (Happy) greens.

The two houses were back-to-back between the parallel fairways. As with almost all the WP houses, theirs were nestled in dense pine forests. A mix of Loblolly, Slash and Longleaf pines, the trees provided shade, visual appeal and backyard privacy.

Tracy and Happy added back-to-back swimming pools. Skinny dipping, poolside basking for all-over tans ... the privacy was more site-dictated than anything. Neither 32-year old woman was concerned about being seen in the buff all that much.

Nor were their two 14-year old children, named after their great-grandfathers. Tracy's son, Rip, and Happy's daughter, Haley.

Well, more about the daughter part in a moment.

Rip and Haley, born a month apart, had grown up together. Best friends. Tracy and Happy were interchangeable mothers. With interchangeable kids. Love abounded in the Thornton and Stevenson homes.

Technically, Haley was a boy. She certainly had a little penis and a pair of tiny balls. But if ever a girl were born in a boy's body, it was Haley. Happy had wanted, really wanted, a girl. Haley became what both of them wanted. A girl.

Happy and Tracy raised Haley as a girl from the day she came home from the hospital. Treated her as a girl, dressed her as a girl. Haley had always felt like a girl and a girl was what she was.

Community acceptance wasn't automatic, but gradually all but the hardcore Christian right acknowledged Haley's femininity. The teasing at her private school died out on its own by second grade. Haley was a girl, deal with it.


Tracy was tall, 5' 9". Rip was taller. Tracy had lush auburn hair, a strong chin, blazing green eyes and a model's cheekbones. Small, but perky boobs, tiny waist and long, slender legs. Cat-graceful.

Rip had his mother's wide swimmer's shoulders, narrow waist, and thicker, more powerful legs. His cock, a source of pride to Tracy, wasn't that long, just over six inches, but thicker than most men's. And, as Happy told Tracy, "He's still growing."

Happy's boobs weren't the first thing most people noticed. Well adolescent men and boys did. But it was her heart-shaped face, framed by natural ash-blonde hair, that drew the eye.

At 5' 4" she was a good five inches shorter than her best friend. But that stunning face with deep blue eyes captured the room's attention every bit as much as Tracy's model-like stride.

Happy knew she had great tits. She knew men approved and a lot of women envied her chest. Large as her boobs were, Happy didn't sag when she went braless. Which was most of the time. She was proud of her puppies and loved showing them off.

Cleavage, crop tops, thin silk ... these and other Happy stratagems were well appreciated by the male WP denizens.

Haley, except for boobs and certain male equipment, was a Happy replica. Haley, like her mother, was proud of her beauty, confident in her appearance. And growing in awareness of how her sexy good looks affected the same males who admired her mother and Tracy.

The four -- Tracy and Rip, Happy and Haley -- had dinner together almost every night. Haley's gradual makeover was a frequent topic of discussion.

Following years of medically supervised estrogen treatments, Haley's new boobs were on frequent display. Happy and Tracy, as well as Rip, examined them, gently felt them, praised Haley on her sexy little body.

When the treatments had run their course, Happy and Tracy took Haley to California for breast augmentation. A month after her 14th birthday, she shyly, but proudly did the big reveal for Rip.

He teared up with happiness for Haley. His best friend forever. Rip threw his arms around her and just hugged the little girl. He whispered, "More beautiful than ever, honey."

Tracy said, "Walk the walk, sweetheart."

Ramrod straight posture, shoulders back, pelvis forward, Haley strode back and forth across Tracy's living room. Her new boobs were about the same size as Tracy's, but seemed larger on her small frame. Haley's little penis was erect, pointing straight out, a common sight over the years.

Rip let out a wolf whistle as Haley pivoted on her fuck-me's. Tracy applauded. Happy beamed with pride at her little girl.

The big question.

That night at dinner, Tracy asked Happy, "Well?"

Everyone at table knew Tracy was talking about The Operation.

Happy said, "I just can't make up my mind."

Tracy understood. She too had mixed feelings.

Haley wanted the surgery.

Rip loved her just the way she was.

Tracy persisted, "But?"

Happy said, "I'm leaning that way. A little more every day."

Haley, sensitive to Rip's feelings, patted him on the hand, "You'll love my new pussy, baby."

Happy started her daughter on trial evaluations. Therapy.


Rip Thornton, just shy of 6', had been given golf lessons since he was 3-years old. A Florida Junior Champion, he was already talented enough to make most college golf teams.

There was talk, around WP, about Rip's turning pro. There would certainly be enough local money that he wouldn't lack for sponsors.


Rip just didn't enjoy the game that much. Didn't have the passion. He competed, more because Tracy wanted him to than anything else. Rip loved to please his mother.

Haley, was like her mother. A decent tennis player with good coordination. And both loved the attention they drew with their sexy little tennis outfits.

Tracy had been Club Champ, women's division, in both sports. But after she won her second golf and tennis titles, she stopped competing and now played only for fun. She didn't have anything to prove.


Tracy and Happy cheerfully gave up their virginities at an early age. A very early age. At 32, they saw no reason slow down in the bedroom. If anything, their sex drives were stronger than ever.

The two mothers put Rip and Haley in nursery school. Then preschool. Kindergarten, elementary school, middle school. All good schools, all private.

By the time they were five, Rip and Haley knew not to go inside if a different golf cart was pulled around to the back of one of the two houses. Tracy, or Happy, or both of them, were entertaining.

The two kids would just strip and dive into one swimming pool or the other. When the coast was clear, one mother or the other, or both of them, would join the children for a swim.

The main Whispering Pines bar was called, no creativity involved, The 19th Hole. After a few drinks, paying off bets, much good-natured lying, one of more golfer might pull out his cell and call Tracy or Happy. Or both of them.

It was just a leisurely stroll across the 18th fairway to the two houses. Tracy and Happy didn't say yes to every caller. Nor every time. But as Tracy explained to their two third-graders, "Happy and I like to fuck."

Rip and Haley nodded. No new news there.

For the rest of this story, you need to Log In or Register

Story tagged with:
Mother / Son /