A deceased uncle’s will entrusts a delicate task to his favorite nephew — find an old flame of his and deliver a bequest. But who is she? Uncle Cyrus called her “Rose Red.” Jack, the nephew and executor of Cy’s estate, doesn’t know who she is. He only knows one thing about her. She loves to be spanked. From the collection Anne of Wulfstedt and Other Stories.
Jack was flattered but for the life of him he did not know why Uncle Cyrus had chosen him to be the executor of his estate. His Uncle Cy, a larger than life, gregarious bear of man was dead at fifty-five, practically in the prime of his life. Jack was aware that Cy had known that he had high blood pressure, and that he had made plans for this possibility, but still, the sudden fatal stroke had been a shock.
Cy never married and had no children. Jack filled part of that void. He’d been Cy’s favorite nephew, almost like a son. He’d spent summers and vacations with Uncle Cy, fishing the Yellowstone, hunting in the Rockies, mountain climbing in the Cascades.
But still, Jack had just graduated from law school, and for Uncle Cy to have entrusted this task to him when he was such a rookie—well, it was unexpected, to say the least, and a bit unnerving as well. He didn’t even know what to do. That’s why he was here at Conroy and Bailey, the law firm who would represent him in all probate matters.
He thought back to all those nights around the campfire. Yeah, Uncle Cy was a character. A rich entrepreneur from Seattle, never married, but quite the ladies man. He’d often seen Uncle Cy in the society pages, in the tabloids even, always photographed with some starlet or other hot young thing on his arm. It was a subject they’d talked about a lot.
Jack was a tall, rangy, good looking guy, but not particularly successful with the ladies. “I just don’t know what they want, Uncle Cy. Girls are a mystery and I’m sort of shy I guess. I try to be accommodating and a gentleman and all, but they seem to get bored with me or something.”
“It’s true, you should always be a gentleman,” Cy had said. “But women also like a man who is forceful, one who’ll take charge. They’ll try and push you around, act like spoiled brats, expect you to cater to their whims. Don’t do it. You’ve got to take a woman in hand.”
Jack especially recalled one night out under the stars on the Snake River. After a day on the river they were sitting around an open fire, passing a whiskey bottle back and forth. The conversation once again turned to the female of the species.
“Deep down, you know what they want?” said Cy. Jack said he didn’t know. “I’ll tell you my secret,” he said with a wink. “Most of them want to be taken in hand. They want you in control, setting limits, not tolerating foolish behavior, bad habits or tantrums. When the little darlings get too full of themselves, do you know what I do? I take them across my knee, pull their little panties down and spank their little derrieres for them. That’s what I do. And you know what? They like it.”
Then Cy had laughed heartily, tilted the whisky bottle back and had taken another big slug. Jack had been dumbfounded. “There’s even this one,” Cy continued, wistfully. “I call her my Rose Red. Because that’s what her bottom looks like after I’m done with it. And you know what?” Jack had shaken his head. “She can’t get enough. She likes to have her little caboose paddled until it is rose red and shining like a beacon. And then, my boy, she is an absolute wild woman.”
Jack listened in amazement. “Rose Red? Is that her name?”
“No, no. It’s just my secret nickname for her. Not even she knows that I call her that. It’s just the way I think of her.”
Jack had been stunned to hear this from Uncle Cy, but he never forgot it.
Jack came out of his reverie when a young woman approached him as he sat in the waiting room. She was about his age, medium height and pretty, with red hair and nice legs.
“Hi,” she said, extending her hand. “I’m Molly Burns. I’m a new associate here and they gave it to me to walk you through being an executor.”
Jack took her hand and shook it. “Thanks, Molly. I’m just out of law school, so I’m a rookie. I’m in your capable hands.”
“Well,” she laughed. “I’m new too, so we’ll learn together.”
She led him down a long hallway. Inside a conference room there was a box from which she took some papers and spread them out.
“This one is a bit strange, Jack,” she said. “There is the will, and then there is another document held by an escrow company with specific instructions. The will contains a number of specific bequests. Some are to people, some to charities and institutions, but there is one which is very odd. Cyrus Gordon gave the sum of $250,000 to someone he called merely, ‘Rose Red’. We don’t know who that is or how to contact them. The will leaves explicit instructions that his executor is charged with personally delivering the bequest to Rose Red. That means you, as executor, have to find this person.”
Holy crap, thought Jack. The woman Cy had talked about. But he’d never said who she was.
“Then there is this other document. It’s a scroll that says “Last Will and Testament” bound in a red ribbon. Very mysterious. It could be a codicil. But it’s held in escrow with instructions to release it to you when the gift to Rose Red is delivered or 90 days after the will is admitted to probate, whichever comes first.”
She went over some other details with him about assets and taxes, and told him that the will was scheduled for a hearing in a few weeks, a mere formality, at which the will would be admitted to probate.
“We also have some of your uncle’s effects that were in his lock box with the will. Um, notably, there is a ‘little black book’.” She handed it over to Jack. “You might find it useful in tracking down this ‘Rose Red’.”
This could be complicated. Still, there was one thing about Rose Red that he, and he alone, knew. But why didn’t Uncle Cy just use her real name?
Back at home Jack examined the black book. There were lots of entries, but many dated back years. He decided that Rose Red had to be one of the women Cyrus been seeing recently. Cy talked about women all the time on their trips, but he hadn’t ever mentioned Rose Red until that rafting trip on the Snake. And he’d spoken about her in the present tense as if she were a current girlfriend.
He poured through the book and did internet searches. He was thus able to eliminate most of the entries as old affairs. But it appeared that there were three current names which could still qualify. The time frame was right and they lived in places where Uncle Cy had been just before his death. There was no help for it. He’d have to interview each one and determine if any were the mysterious Rose Red.
The first was Mindy Halton, an “aspiring actress”. Cy had seen her several times over the past year and had been instrumental in getting parts for her in plays and on TV. Jack had to fly to New York, but Molly assured him the estate covered expenses. He called on her in her Soho apartment.
Mindy turned out to be a cute pixie, a short girl with cropped coppery hair and a ballerina’s figure. They talked for a bit, and in Jack’s estimation she was a little kooky—definitely uninhibited, a free spirit, spontaneous and impulsive, flitting from one thing to another.
“I miss Cy so much,” she said, once Jack had explained who he was. “He was a real prince, you know? He would call someone and get me a part if I was out of work. Like the last one. Only it was waaay off Broadway.” She rolled her eyes. “But it was fun. I had to play a naughty schoolgirl who gets sent to the principal. So why did you come to see me?” They were sitting on her couch. She was dressed in a leotard and sweat shirt, the standard uniform of the Bohemian actress.
That last part got Jack’s attention. “I’m trying to find someone mentioned in the will,” said Jack. “And it had to do with certain, er, intimate activities involving Cyrus. It’s a bit indelicate, but if you could tell me what the two of you did when you….”
She cocked her head and smiled. “Oh, I see.” She held up a finger. “I know. Maybe if I showed you the part that Cy got me. In the play. He helped me rehearse. That was the last thing we, er, did.”
“Uh, ok, tell me about this part?”
“Well,” she said coyly, “Cyrus rehearsed it with me a few times. Do you want to see?” Jack said ok. “Then wait here,” she said.
Giggling, she jumped up and bounded into the next room. A few minutes later she reemerged. Jack sat up. She was clad in a short plaid skirt and a figure-hugging blouse. White knee socks with loafers and a ribbon in her hair completed the ensemble making her look like an overripe teenage schoolgirl. She carried a sheaf of papers in her hand.
“So, this was ah…experimental theater. So anyway, here are your lines. You read the Principal’s part.”
Jack looked at it. Cleared his throat.
“Um,” Jack read, “This is your fourth tardy slip this month, young lady. Do you know what that means?”
“Oh, Mr. Johnson, I’m sorry. My locker wouldn’t open.” She squeezed her hands together, pleading.
“And that’s the same excuse you used last time, Nicki. Detention doesn’t seem to do you any good, does it?” Jack read his lines with as much dramatic oomph as he could.
“That’s very good,” whispered Mindy. Then she got back into her role.
“I’ve heard all the excuses I want, Nicki.” Jack read the script in his best stentorian voice. “This time it calls for sterner measures. Come over here.” It said ‘principal sits in armless chair’. Jack looked around and found one against the wall. He dragged it out and sat down.
Mindy, wearing a downcast look, shuffled reluctantly over next to Jack in the chair.
Jack looked up at Mindy. “Now what?” The page just ended.
“It’s extemp. You make it up. But what you are supposed to do is spank me. Here,” she said and plopped herself across Jack’s lap. “Go ahead,” she said, looking back over her shoulder.
“Yes.” She reached back and flipped up her skirt. Underneath she wore wispy black panties. They barely covered a cute and very pert little bottom. Then she astonished Jack by reaching back and slipping them down, exposing her bare bottom to Jack’s gaze. “Spank me for being a tardy schoolgirl,” she said in a husky voice. “Paddle my bare little fanny.”
Jack was astounded, but figured this was one sure way to find out if this was Rose Red. It sure seemed like it. Jack started smacking her bottom lightly, one cheek then the other. Mindy wriggled and pleaded for mercy. Then she looked back at him.
“Oh, go on. You have to do it for real. You’re barely tapping me. Spank me like I’m really a bad girl.”
After that Jack let loose and smacked her wriggling hiney repeatedly for about a minute without holding back.
“Ohh! Ow! Ow! I’m sorry!” she wailed as Jack spanked her bottom to a dusky red.
After another minute or two of steady smacking. Mindy’s cries had become rather shrill and she was doing a flutter kick, so Jack stopped and rested his palm on her bottom.
“How was that?” he said, rubbing his palm around on the inflamed cheeks.
“Ummmm,” she said. It sounded like a near moan of contentment. “Just like Cy. Now let me show you what I’d do for Cy when he spanked me so good.”
She slid to her knees and fumbled with Jack’s zipper. By now he was hard as a steel bar and his cock popped straight out. Jack sucked in his breath as Mindy ran her lips across the length of his penis. Then she gobbled it up, licking and sucking and pumping her head up and down. Jack didn’t last long. He came furiously. After that it was into the bedroom for the rest of the afternoon.
“I can see the family resemblance,” said Mindy when they had dressed and were sitting down again. “You sure are a lot like him. And just as much fun.” Her eyes sparkled.
“Yes,” said Jack. “Well, I’m handling the will because I’m his nephew.”
“Well, I hope you find the girl you’re looking for,” she said. “I’d like to see you again regardless. Maybe we could rehearse some more.” She smiled brightly.
Whew! Thought Jack as he exited Mindy’s place. She was obviously a prime candidate, but he’d decided he couldn’t tell any of them about the money. So he had to just say he was looking for someone without giving that part away.
Back in Seattle he called Molly and told her what he had learned, obviously leaving out a few details. He found he was attracted to her and had the thought that he’d like to see her on a social basis, too. To his delight she agreed to go out with him. So he made a reservation at the best restaurant he knew. But he found himself cooling his heels waiting for her. They ultimately lost the reservation and had to change plans. Her explanation? A girlfriend had called and she had yakked on the phone and lost track of the time. Jack was irritated, but the rest of the evening went well. She was still possible girlfriend material.
Next up was a woman named Magda Belinsky. She lived in LA.
To be continued