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The Inheritance


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I spent the flight back down to the Keys thinking a lot about Teddy.    Teddy seemed to have lived life like he wanted and had touched many lives down on Duval street.    Partially, because he could, but I think it was Teddy’s innate character.    He always helped me when I was growing up even when he didn’t have millions.

By the time I landed, I was determined to be the same sort of person.   If there were a way to help someone I would do it.    I had the time and money to do so.   I hoped I could maintain the resolve.

I got off the plane with my winter coat over my arm.   I’d not need to wear this again for a while, I hoped.   I’d have thrown it in the trash, but I might travel somewhere cold.   I wasn’t going to rule that out.   I fetched my two suitcases and got out to my car.    I threw them and the coat in the trunk.    I went around and ran the top down.     It was hot.   I had worn long pants in deference to the northern climate, but I wished for shorts now.    I’d be home in a few minutes, and I could change.

Then I thought about it.   What the hell, I thought.   If I was going to act like Teddy, I might as well act like Teddy.    I kicked my shoes off and unfastened my pants.   I slid them off and stood there in the diaper.   I pulled off my socks and then threw it all into the passenger seat.   I got in the car and drove home.

I was pulling the suitcases out of the car when Kristie came out of her house and waved.

“Decided to go into Teddy mode?” she asked.

“Not sure, but it was such a warm day, and I was dressed for the great white north when I got on the plane, that I decided to ditch the pants for the ride home from the airport.”

Kristie smiled.   “That’s how it starts,” she said.

I went inside and unpacked the suitcases.   A day later, the UPS driver showed up with my boxes.   I wasn’t even thinking about it when I signed for them, wearing just a shirt and a diaper.     He didn’t take any visible notice.  I guess they’d seen more bizarrely dressed people answering the door than this.

I unpacked the boxes.   I moved some of Teddy’s stuff I didn’t need for into the empty boxes.    A few minutes later, another delivery came.   I opened it and found it was my plastic pants.    I went and switched into cloth and tried the new ones on.

A few more days went by, and I realized I had spent the entire time not wearing pants over my diaper.   Of course, I had not gone anywhere farther than Kristie's, and besides her, nobody had seen me.     I was sitting doing some work moving money out of the mutual funds into better investments when the two men came to the door.   I let them in before I remembered I wasn’t wearing pants.     It didn’t seem to bother them.

“I’m Jim Moss, head of the Key West chamber of commerce, and this is Arturo Sandoval.”   Arturo was a short, slim man and was holding a box.

“The artist?” I asked.

“You’ve heard of me?” he said with just a touch of Latino accent.

“I’ve seen your work at the gallery on Duval.   It’s quite good.”

“Thank you.”

I directed them to a pair of chairs and sat down myself opposite them.   “Now, what can I do for you?” I said.

The two men looked at each other and smiled.

”What?” I asked.

Jim replied.   “Sorry, that is exactly the phrase your uncle used all the time.    Usually when I go visit people expect I’m going to ask for something so they’re like ‘what do you want?’ or ‘what now?’ or the like.    They're not impolite, but that’s the way it is.   Your uncle always said ‘What can I do for you?’ even if we didn't intend to ask for anything.   That’s just the way he was.   You see to be like Teddy in many ways.”

I smiled and realized that they were probably also counting the fact I was sitting there in a diaper.   But, I repeated the question, “What can I do for you?”

“Well, Teddy Moore was an asset to the community.   We want to erect a statue in his honor.    I know Teddy would never have wanted anything while he was alive.”    I thought about the box full of awards in the closet.   “We think he might approve of this.   Since you are is relative and heir.   We thought we’d run the proposal by you.”

Arturo was now opening the box.   “I’ve made a scale test carving.”  He extracted it from the box and held it up.     It was Teddy for sure.   He was standing there with an outstretched arm and his big grin.   Of course, he was wearing a diaper.

“It’s a remarkable likeness,” I said.

“Thank you,” Arturo said.

“Arturo has volunteered his time to make the sculpture.    We’re raising money to pay for the materials.”

“How much will that run?”

“Probably about $10,000,” Arturo said.  “Plus, the site prep work, but the city has said they would cover that.”

I slid my chair back to reach my checkbook and started to write.

“Oh, no,” Jim said.  “We didn’t come here to get you to pay for it.”

“It’s nothing,” I said.  “I’m sure the chamber has better use for the funds.”

Jim didn’t protest too much.   “Thank you.”

“Is there anything else I can do for you?”

“On an unrelated note.    We understand you came from the financial industry.    We were wondering if you could give us some advice on a problem that has come up.”

“Sure.”

“I’m also on the board of a non-profit organization who has been contacted by a citizen who wants to leave us a substantial amount of money when she dies.     We weren’t sure what the best way to help her do that.    Would a will suffice, or there are other things we’ve heard of.”

“A charitable remainder trust,” I stated.

“Yes, exactly.   We don’t know enough about it to advise her, and we don’t know who to ask, so we thought since we were coming here anyhow.”

“Not a problem, you need an attorney that handles estate work.   I know just the person to ask, and she’s coming down from Miami soon anyway.   I’ll see if she would be available to talk to your benefactor.”

“That would be marvelous.”    They chatted a bit more and left.   I called Janet and filled her in, and she said she would be glad to talk to the donor when she came down.”

Kristie came over.   “Was that Arturo with  Jim Moss I just saw leaving?”

“Yeah, they wanted to show me a statute of Teddy they’re erecting on Duval street.”

“That’s a marvelous idea.   Teddy would have hated it.”

“Yeah, I know.   There’s a box full of plaques and things in the closet.   I figured he wasn’t the kind to show off.   But he’s gone, and it’s going to make people happy.   I probably could have talked him into it.  Oh, and they both think I take after my uncle.”

“Well, if you’re going to hold court in a diaper, they’d be right.”

We both laughed.    “That was accidental.    I just got used to sitting around the house like this.”

“Well, I was thinking about going down to Mangoes for a drink.    You want to come?”

“OK,” I said.

“Let’s go then.”    The implication was clear.   I was to go as I was.    Why not?    I followed her down the street.

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Very interesting, I was in Key West several (many) years ago and noticed several guys wearing plastic panties in lieu of shorts.  As I remember they were a dark color so I did not happen to noticed if they were wearing diapers underneath.

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This time we were right in the heart of Duval street.   My heart was pounding, and I was happy to get to a table.   It had become usual that people would come up and express praise for Teddy and regret that he was no longer around.

I was walking home when I heard someone call “Teddy.”  I turned around.

“No, Jake,” I said, holding out my hand.

“Sorry, from the back, you looked like Teddy.”

“I’m Teddy’s nephew.   I’m sorry to say that Teddy passed away a short time ago.”

“Oh,” the person said, taken aback.   “I’m sorry for your loss.   Teddy was such a big asset to this community.”

“Thank you.   I hear that a lot.  I’m hoping that I can do the same.”

“So, you’re following in Teddy’s footsteps?” the person said.

“I guess you can say that.”

“Or in his diapers, I should say.”   We both laughed.

“So, what can I do for you?”  I said.

She laughed again.   “You sound just like Teddy when you say that.     Teddy and I were talking about my business idea.   I got busy on the implementation and have been a bit out of it, so I guess I missed the sad news.”

“Come, let’s go sit on my porch, and you can tell me about it.”

“My name is Ivy Grant,” she explained.   “Teddy helped me with some of the planning with this new business I’m starting.   I think he was intrigued by the concept.”

“And the business is?”

“I’m starting a diaper service.”

I smiled.   I’m not surprised Teddy was interested.   I was interested.    “Sounds intriguing to me as well.   What can I do?”

“Well, I hate to ask this not knowing you, but I was hoping that Teddy could float me a small loan.”

“Do you have a business plan worked up?”

“I do.”   She reached into her bag and pulled out a USB stick.   “Teddy always wanted things electronically.”   I put it into the port on my machine and brought it up.    I spent several minutes reading through it.

“It sounds like a reasonable plan.   Where are you coming up short?”

“We’re ready to go, and we’ve prebooked some pregnant customers and have some existing moms with children still in diapers to change over.    The issue is getting the inventory stocked up.    I was hoping that some of the suppliers would extend us 30 or 60 days credit, but it isn’t happening.   We need just a touch to tide us over.    The rest of my investment is already tied up in the equipment.”

“How much?” I asked, and she quoted me a number.

“And will you do adult diapers?” I smiled.

“Teddy and I talked about that.   I’m not sure the market is there for us to offer a complete service.   However, we’re more than willing and able to wash diapers that someone like yourself purchased.    We can still pick up and deliver.”

“How close are you to operating.”

“We’re up and running now.   I’ve got a few ‘beta’ customers, as Teddy would say.   My own daughter and my neighbor has twins.   We’ve been doing loads for the past two weeks.”

I picked up my checkbook and wrote out a check.    I handed it to her.  “What is the rate going to be?” she asked a little wary.

“Zero percent if you pay me back within 90 days.     The only thing I ask is free diaper service until you pay me back.”

“Not a problem.    Do you have some ready to go now?”

“Yes, I found some of Teddy’s here.   I had been a disposable man.   I just ordered plastic pants.  Teddy’s are kind of baggy on me.    I guess I need to order more diapers.”

She smiled, and we shook hands.    She walked out with a check and a bag of my dirty diapers.   I was to be another of the ‘beta’ customers.    I got on the internet and ordered more cloth diapers.

 

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The more I thought about it, the less reason I could figure not to follow Teddy’s leave.    I figured it was safer to wear plastic pants, whether I was wearing cloth or disposable.   I had tried on the various ones that I had ordered and ordered some more.     A few days passed and Ivy brought back my diapers, freshly laundered and I gave her some more.     Kristie came over often and goaded me into going out more.    We spent a lot of time cruising the bars of Duval street in the evening.

A man came up to me one day.   “I’ve been meaning to ask you something,” he said.

“How can I help?” I said.

“I work with the local youth charity.    We do a lot to help mentor kids, deal with teen parenting, try to keep kids occupied when they’re out of school.   Anyway, we have a charity 10K every year and Teddy was always one of our big organizers.”

“Sure, I’ll be glad to help.   I’m not sure I know what to do.”

“Teddy wrote a manual on running the event.”   Of course, Teddy did.   He was meticulous about things like that.   “I’ve got a printed copy in the office.”

“I bet I can find it on his computer.   What is the date?”

We discussed it further.   I saw no reason why I couldn’t help, just another way to follow in Teddy’s footsteps.  Sure enough, I found a whole folder of Teddy’s notes on how to conduct various events.   Teddy loved to organize events.

I got a phone call.   Janet said she would be driving down this Thursday if that was OK by me.   I told her I would set up the meeting for the charity donor on Friday.    She said she’d show up with my papers around noon on Thursday.

Just around noon on Thursday, Janet showed up.   I met her on the front porch.

“I see you’re in full Teddy mode now,” she said.

“You knew about Teddy’s diapers.”

“Of course, I had several meetings with him dressed as you are now.”

We went inside.    She handed me a check and had me sign the papers.    “Your uncle’s estate is now officially closed.”    We chatted a bit longer.

“So what are you doing the rest of the day?” I asked.

“Well, I’ve not had lunch, so we could go eat.   After that I’ll probably cruise the shops and galleries a bit.   I love Key West.   I used this meeting and the one tomorrow as an excuse to make a trip down here.   I’ll probably stay through the weekend.”

“Where are you staying?” I asked.

“I have decided.   I  usually stay at a guest house off Duval.   I wasn’t too well organized on that aspect.    If they’re booked up, there’s always a number of motels up on Route 1.”

“Well, now that you’re no longer involved in my inheritance, there should be no conflict of interest.   Why don’t you stay here?”

She hedged for a second.   “I mean, I do have a guest room.”

She thought about it for a second longer.   “Sure.   Let me go get my stuff.”

She went out to the car and returned with a small suitcase.    I showed her to my spare room.    “Kristie, the woman next door, has laundered all the sheets.   She took good care of cleaning the place up when Teddy died.”

“I think I’ve met her.   She’s very nice to have done that.”

“Everybody loved Teddy.”

Janet went into the room and closed the door.   A minute later she emerged wearing a bright covered dress rather than the business suit I had always seen her wear professionally.   She looked quite stunning.   I  told her so.

She patted the seat of my diaper and said, “You don’t look bad, either.”

We headed off to find lunch.

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“Have you been to Nine One Five yet?” Janet asked.

“No, there are so many great places here,” I admitted.

“It’s fancier for dinner, but they have salads and small plates for lunch.”

“Sounds good.”

I grabbed the larger diaper bag as I figured we’d be out a while.    We headed over to Duval and turned south.   Nine One Five was indeed 915 Duval Street.    There was one outside table left, and we took it.   The salad was good, and so were the various things we got.   A cone of French fries, some fried octopus, and the like.    Janet told me of her love of the Conch Republic.

“Well, you should move here.   You can hang out a shingle on your own or open the Key West office of Asher and Green.”

“I wish I could,” she said.

After lunch we started up Duval Street doing window shopping, occasionally going in for a better look.   More than a few people recognized me because I had either I been introduced to them before or they knew about my relationship to Teddy.

We entered a gallery, and Arturo came out and greeted me.    “Arturo, how are you.   How’s the statute coming.”   We talked for a bit, and then I realized my manners.  “Janet, this is Arturo Sandoval.   Arturo, this is the lawyer that handled Teddy’s estate, Janet Green.   Arturo is making a statue of Teddy.”

Arturo showed us some of his other art, and then we moved along.   Ivy ran up to me.   I introduced her to Janet.   “I’ll be able to pay back your loan early.    Business is great.”   She bustled off.

“Jakie!” I heard a shrill voice.   It was Rose, the drag queen.    She ran up and threw her arms around me.   I felt the embrace slide down, and she gave my butt a tweak with both hands.   We broke apart, and she noticed Janet.   “Who’s the lovely lady?”

“Rose, this is my friend Janet.   She was Teddy’s lawyer.   Janet, this is Rose, another fixture of Duval Street.”

Rose and Janet chatted for a bit, and then we continued our trek.    As evening came we stopped at several bars and had a drink or a snack in each one.    Again there were more than a few people who greeted me as a regular.

“You seem to be a popular guy here.”

“Well, people have no problem recognizing me as being related to Teddy.”

“What about Arturo and Ivy?”

“Well, I’m trying to carry on in Teddy’s legacy.   That’s how I met them and why you’re going to see the charity benefactress tomorrow.”

Janet smiled.   We’d made the full circle and were heading south again.    Since we were close to the house, I ducked inside to make a more comfortable change.  Kristie was out on her porch, and she struck up a conversation with Janet while I went inside.

Changed, we proceeded back south.   “Do you want to have dinner some place?” I asked.

“I couldn’t eat a meal at this point.   Let’s continue our nibbling down Duval.”

We were having a good time, and she turned me off Duval to the east.    We got to a small place called “Better than Sex.”

“It’s a dessert restaurant,” Janet said.

“Is it?”

“Yes, that’s what’s on the menu.”

“No, I mean, is it better than sex?”

“You’ll have to find out.”

We went in and had an intimate booth.    We sat together touching and had some wine that came in a chocolate-rimmed glass.   I had cheesecake and Janet had bread pudding.   “I love bread pudding,” she said.    After a while, we emerged.

“What next?”

“Let’s take the short cut back to your place,” Janet said.

We made it back home.    Janet asked, “Do you need a change?”

I nodded.   She poked around and found a spare cloth diaper and pushed me onto the bed.    She slid off my plastic pants and unpinned my diaper.   She attacked me with wipes, paying particular attention to my penis until it was impossibly erect.   She took the clean diaper and slid it under me.    I thought this was going to lead somewhere, but now she was putting the diaper back in place.    I had a pang of disappointment.

Then she hiked up her skirt and climbed up on the bed.   She hadn’t been wearing panties.   She maneuvered her self over me and slid the diaper down and took me inside her.

“Pull the diaper up over us,” she said.   I didn’t understand, but I complied.   We made love with the diaper loosely draped over us.    When it was over, she rolled off me and pinned my diaper back in place.    She snuggled into my side.

“That was wonderful,” I said.

She chuckled.    “You can tell Kristie that I did.”

“You did what?”

“Get inside your diaper.   That was her suggestion to me earlier.”

I laughed.   “So that was what that was about.”

We talked.   Then she asked, “Well, have you come up with an answer to the other question?”

“What question?”

“Was dessert better than sex?”

I chucked again.   “Close, but not better.”

She drifted off to sleep.  I picked up the plastic pants and pulled them back on.    I didn’t know if I was becoming incontinent, or that I just got used to not worrying about going, but I didn’t want to leak.”

 

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Lol I should have read your last update before I posted my last post. I like the update someone finally change Jake's wet diaper. Not sure if Janet will continue to the baby side of changing Jake's diaper. Didn't read anything about Uncle Teddy being that way. 

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The next morning I woke to the smells of something cooking.    I looked over and saw that Janet was up.   It must be her.    I padded out into the kitchen and found her at the stove.   “Bacon and Eggs?” she asked.

“Sure.”

I noticed she had started the coffee, and I poured myself a cup.   “Last night was wonderful,” I added.

“I’m glad you liked it.”

After breakfast, I stood and pushed out my usual morning bowel movement.    I noticed her watching.   “Sorry, I probably shouldn’t have done that in front of you.”

“It’s OK.   So you never use a toilet?”

“Nope.   I’ve been that way for a while now even before I came down here and got into Teddy mode.”

I went off to change, shower, and dress.   I came out and found she had changed back into he business suit.   “I’ve got that meeting with the charity lady,” she explained.

We found our way to the woman’s house.   It was a bit grander than mine.   Jim Moss was waiting outside, and Janet decided it would be best if she met with the woman alone.    So Jim and I stood on the porch.

“I talked to Arturo yesterday.   He says he is progressing on the statue,” I said.

“Yes, I was meeting with the city government about the site.    Arturo did these sketches.”

He held them out to me.   There was a picture of the statue standing with the arm outstretched.   I could see Duval street spreading out in the background as if Teddy was directing something down the road.

“We’re going to set a date for the dedication soon.   It will be officially Teddy Moore day.”

“Now, there’s a party that Teddy could get into.”

“He loved to organize events.”

“Yeah, I’m learning that.   I’m working on the 10K coming up.   I’ve gone through Teddy’s documentation of previous years.   It’s pretty meticulous.   I guess that’s his computer genius applied.

After a bit, Janet popped outside.    “We’d like you to come in now.”

Jim and I entered.    The elderly woman shook Jim’s hand and got a unique smile on her face when she saw me.    Janet had answered the legal questions.   She had some financial questions to ask of me, and I did the best I could.    Everything seemed to be going smoothly, and the meeting was winding down.    “Could Mr. Moore stay a few minutes.   I want to ask him a few questions in private.”

Janet and I looked at each other.    Jim Moss immediately spoke up.   “Of course, Ms. Green and I will wait outside.”   The two excused themselves.

The woman leaned forward and spoke softly.   “I’ve seen you out and about.    I remember your Uncle Teddy as well.”   I nodded. Everybody knew Teddy.     She leaned even closer.    “Am I right to understand that you wear diapers by choice?”

There she had it.   “Yes.   I have worn diapers just because I like to for a long time.    When I moved down here and learned about Teddy, it didn’t take long to follow his lead.”

She leaned back a bit, and I thought that might be the end of the conversation, but she was gathering up the hem of her skirt to reveal that she was wearing a diaper.   “See, I wear them, too.    Not because I have a choice.   The problems of growing old.    But I do get some choice in what I wear.    I love these because they make me feel young again.”    I looked down and saw that they did have a very juvenile print on them.      She dropped her skirt down.    “I don’t tell anybody about this.   But I thought you would understand.”

“I do.   And I like different styles as well.    Mostly these days I wear cloth diapers.    My friend Ivy runs a diaper service and does mine as well as the baby diapers.   She’s very discrete.   I can have her talk to you if you are interested.”

“I might be.”

We chatted a bit more, and I bid her goodbye.    Janet and Jim were talking out on the street, and I went to meet up with them.

“Anything we should know about?” Janet asked.

“No, unrelated to the charity.   She just had some personal things to discuss with me.   Private.”

Jim said his goodbyes, and I asked Janet what was next.

“Let’s go back to the house.   I want to ditch this suit, and you probably need a change and to pick up  your diaper bag so we can go out again.”

That sounded good to me.

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We ran up the porch and into the house.    Janet popped into the guest room, and I went into my room to change my diaper.   I’d just managed to peel the old one off and drop it in the diaper pail when a naked Janet came into the room.

“Wait for me,” she said, grabbing some wipes.

“I like this outfit better than the business suit,” I said as she started in on cleaning me up.

“The suit is for paying customers like Mildred Flores.”

“Who?”

“Your friend, the benefactress.”

“Oh, I missed her name.   I’m not sure she qualifies as a friend.”

“I saw the way she looks at you.   She’s quite smitten by you for an old lady.”   I smiled and thought about her secret admission to me.     Janet was now pulling me as she made her way backward to the bed.   It was clear what was to happen next.

After sex, Janet grabbed more wipes and cleaned me up again.   She grabbed a diaper and pinned that on me.    She then rifled through the plastic pants available and found a black pair.    “Try these.”

I pulled them on.   “Well?”

“Very sexy,” she said.    We headed back to Duval street.   “Seafood?” she inquired.    DJ’s was right on the corner, so we popped in there.   It has become my favorite place for a fast bite.  We got conch fritters and lobster rolls.

After lunch, I let Janet lead.   She wanted to do some more shopping, so I followed along.    At dinner time we headed over to Virgilio’s for cocktails and dinner.    Finishing dinner, the band started playing in the lounge.   “Do you want to stay here?” Janet asked.

“Well, Rose is on stage over at Aqua tonight?” I said.

“Was she the one playing grabass with you yesterday?”

“You noticed that?   Yeah, that’s just Rose.    She usually just hugs people indiscriminately, but I guess she finds the diaper a license to do more.”

“Sure, let's go.”

Rose shared the billing that night with two other “girls.”   We had a blast listening to them perform, some singing, lots of joking around.  During a break, Rose and one of the other girls, Ilsa, came over.   Ilsa was African-American with a shocking spray of blonde hair.   I was pretty sure it had to be a wig, but you never know in Key West.

“Jakie, darling.    This is Ilsa.   She so much wanted to meet you.”

I stood, and Ilsa gave me a couple of air kisses on each cheek.   “That’s true.    I’ve been dying to meet you ever since you showed up on Duval Street.   We were all such a big fan of Teddy’s.”

I introduced Ilsa to Janet, and we all had a drink together until it was time for the girls to go back on stage.   We sat through the next acts and then decided to continue bar hopping down the street.   When two AM rolled around, we were still going strong.    We headed to the Green Parrot because they were still open.

“This is the part that still takes some getting used to,” I said.  “At home, the bars close at two, and when they do, they don’t open until after noon the next day.   Seven AM to four isn’t uncommon here.”

Janet agreed.   We had a few drinks and said hello to a few good well-wishers.   We didn’t make it to four AM, though.   We headed home, and Janet and I got back into bed together.

In the morning, Janet told me she probably should be getting on the road around Noon.   I suggested we go to Blue Heaven for brunch, and that’s what we did.    When we were nearing the end of the meal I asked the inevitable, “When will I see you again?”

“Well, I will probably need to come back and see Mrs. Flores in a few weeks.    We can see each other then.   Of course, you could always come up to Miami.”  She paused.   “Even if it does mean you’ll have to put pants on.”

I smiled, “Yes, I’ll put pants on from time to time for you.”

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