Darby Dee Daniels 05

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Darby Dee after her banana split date the night before.
2.6k words
4.39
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Part 5 of the 7 part series

Updated 06/10/2023
Created 08/01/2021
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I should be sitting on my deck with a cup of coffee on this beautiful Friday morning, but I'm standing because of the blistering Scott gave my backside last night. I know I asked for it and I would like to point out that I took it, but when your date has a thing for spanking you better watch your back or your backside will be covered with raspberries. Which mine is, but I had my ice cream date so it was worth it.

Unfortunately, I may not get my other planned dates with Scott because of the way Sylvia had to step in last night and finish off my date for me. Don't get me wrong, I'm holding out hope but I keep thinking about what Sylvia said last night. She was confident that because Scott has had a taste of "her stuff" I will be dumped by noon today. She may be right, but for now I can honestly claim that I'm dating and I can do that for the next 3 hours. If you don't believe me, just check out my Chang home page, it's all right there. As of 9 am, I have three more dates scheduled in the coming weeks.

But enough of that. I need to start getting my house ready for the stupid Trap on Tranny match making party that I have been forced to host tonight. Everyone at the clothing store is convinced that my having Lizzie and Frankie come over tonight for wine and snacks will automatically have them fall into bed together and everything will be just fine. Hah, like Lizzie and Frankie will not fall for that trick. However, I don't care what actually happens and I will use tonight as a learning experience for it takes to host a successful party.

And when I say I'll take the party host experience, I mean what happens when you put a Crossdresser (me), a Trap (Lizzie) and a Tranny (Frankie) in the same space and feed them wine. Is it a quiet affair or is it a major cat fight? This is question that haunts me and I might find my answer tonight.

A few things I need to do today are to take a long hot shower because I'm such a mess after last night, have the deck power washed, pick up some Luau garnish for the deck rails and pick up a new outdoor table.

My shower can wait because I have a lot of time and because I woke up with my facial makeup mainly intact. That means I'm standing on my deck drinking my coffee as Darby Dee in a pair of bike shorts and a crop top showing off to the kayakers on the river.

I also have to remind Jill that I traded my house cleaning this morning to Trudy for Trudy's food and beverage services tonight. I will sweeten the deal for the Jack & Jill Homes Services by paying extra for Jack to power wash the deck after he cuts the grass. And I know that they will accept my trade and extra work offer because I just spoke with Jill and she likes it when there are dollar signs flashing in her eyes. I don't know how she does it, but the dollar signs actually flash green like LED's.

What I didn't tell Jill was that while she was over at Trudy's, I would be offering the usual bottle of water to Jack in these bike shorts and I may have failed to mention that I will be standing in patio door pointing this way and pointing that way while he is power washing the deck. I mean, he might miss a spot if I'm not bending over and inspecting the deck planks closely.

Now, there is no way Jill will approve of me quenching her hubby's thirst in these bike shorts, so I have slipped on my PJ bottoms and the matching top, unbutton, of course. I also have another edge today because of the fourth Friday of the month pay day thing and Jill has a tendency to turn a blind eye when she's blinded by those dollar signs.

Oh, and there is that new corset and body suit hanging in my closet that Jill ordered from the clothing store. I am absolutely positive that they will blind her a little as well. And here they come and today might be the day I suggest a new muffler for their work truck.

"Oh, I see you're wearing your Darby Dee face this morning. Did you have fun last night or something?"

"I did Jill. It was a wonderful banana split date down by the river in that hidden cove. LOL, I can see Trudy looking out of her window waiting for your services. You should go. Your clothes and monthly fees are in my bedroom. Help yourself."

"Thanks Darby Dee, but if who whipped your dates cream for the banana split? I know it wasn't you, LOL."

"Well, Sylvia chipped in, but he had his way with my backside before she came to the rescue. My buns are now like raspberry treats."

"So, you'll be going back to the clubs to find someone else to date because Sylvia stole him from you?"

"Probably, but that is not confirmed yet. The announcement on Chang is scheduled for Noon."

I'm not sure why Jill took her corset with her to Trudy's house and I didn't have time to think about her trying it on in Trudy's bedroom because right now I have a thirsty lawn care worker and two bottles of cold water. No, no, I'm not trying to seduce Jack, I just want to tease him a little and see how much I can get away with.

I went into my bedroom to remove my PJ's and straighten my hair. I found a receipt from Jill for payment rendered and it was signed with a pucker lips kiss print. I also found all of my cash gone and I mean their payment due and what I was going to spend today. But Jill was nice about it. She laid out my ATM card for me implying that I needed to use it today. Isn't she just so thoughtful?

Or in other words, in my mind that is justification for me to give her precious hubby a bottle of water in bare legs and feet. And because Jack is cutting the grass in the back right now, I will have a little privacy. I'm sure he will be his usual "man of few words", but he may drive by a little slower this morning. Or I could be totally wrong because I think he's coming to a stop instead of flying by and spraying me with grass clippings.

"A nice cold water for you, Jack."

"Ah, thanks, ah, Derek?"

"I'm sorry to surprise you like this Jack, but I am Darby Dee occasionally. Don't over think it and drink your cold water. So, you're to power wash me after you finish the grass, right Jack?"

"Well, I'm going to power wash your deck. Is the washer in the garage?"

"It is Jack. I would pull it out, but I don't want to break a nail. You can pull it out, can't you Jack? Or is pulling it out something we should do together? I mean, according to Chang, that's all I good for, but I've gotten pretty good at pulling things."

"Ah, I better finish the yard so I can get to work on your deck. Thanks for the water, ah, Darby Dee."

Well, that worked. Now I just need to figure out how to do that at Willy G's club. I took my position in the patio doors for phase two. Phase two requires one bent leg, bending over to look under the rails and to point at non existent missed spots. Which I think I was doing quite well. What I didn't plan for was the noise level of the power washer because all of a sudden, Jill was standing right behind me with a frown and her arms crossed.

"WTF is this, Darby Dee? Are you having fun giving my hubby a boner?"

"Relax Jill, it's yours to keep. I mean, you said things have a little slow lately and it would be nice to at least say that there has been sex in Darby Dee's bed. I don't have to post who actually had the sex. By the way, did you walk over here in just that corset?"

"Shut it, Darby Dee. Every neighborhood has that one hottie who walks down the sidewalk in lingerie on a lovely Friday morning, right?"

"So, text your next customer and tell them you are running late. Jack is almost finished with my power wash."

"You mean my power washing is just getting started, right? But, thanks, we could use a little private time. You're alright with us using your back bedroom?"

"Yes, this is all for you, my favorite house cleaner. However."

"Hah, I knew there was a catch. What do you want? To watch?"

"LOL, no, that's what cameras are for. However, I have heard that sometimes that the house cleaner seduces her hubby in a customer's house and gets him so worked up that she doesn't even have time to drop her panties so the hubby just pushes them aside and does her doggie on the favorite customers bed and then she leaves her panties on the bed post as a thank you. Anyways, I've heard things like that happen. Oh, I've also heard that the panties are at least damp."

"Oh, you heard all that, did you? Well, I have heard that a sissy fem boy has to admit that he strokes his sissy dick with damp panties and leaves extra tip money for the favorite house cleaner. Oh, I have also heard that sometimes the greatest house cleaner in Middleton has authority to load her shopping cart up at Gary's Sex Clothing.com under the user Mistress Jill G. Anyways, that is I've heard."

"Hah, I may have forgot to mention that I have heard that once a month the house cleaner agrees to wear that uniform in the closet because she noticed that it has been upgraded to something much less tacky. It's also been said that the house cleaner tells the home owner all about how difficult it is to get one of Trudy's boobs in her mouth because they are so large and full. Oh yeah, and the house cleaner doesn't mind that the home owner is using her panties, again."

"You haven't heard anything yet, fem boy because I have heard that the home owner promises not to jack off into the house cleaner's new nylon stockings until she has at least worn them once or twice. I may have over heard that fem boys like to be spanked while laying across those soft nylon stocking in the hopes of squirting on his Mistresses thighs."

"Well, I have heard that the house cleaner locks up the house after she is done doing her hubby and that she needs reminding to leave a gift on the bed post. I need to run up to "We Be Parties" now."

"Well, I'm absolutely positive that I heard that the home owner never wears bike or exercise shorts in front of mu hubby ever again. Have you heard that, Darby Dee?"

"I heard that once, but it reminded me of the time that these bike shorts were responsible for one huge and fat cock that you need on a Friday afternoon, so we'll talk more about that another day. By the way, have you heard that Trudy expects me to "do" her?"

"I may have heard that she's lonely and could use a good "doing" and there would not be any pressure or regrets. I mean, I've heard that if a woman hangs out at the clubs to get her "do" on, then she may get a bad reputation. I also heard that her servant outfit for tonight will be something to remember. I'm positive that I heard that you won't lose your crossdressing or sissy card if something happens. I'll lock up Darby Dee. Have fun at your party tonight."

"Fine, I'm out, but have you ever heard of someone using panties like a condom when they have sex? I'm just curious."

"Huh, I've never heard that before, but you might want to hold off on the freaking stuff for a while. At least until you "do" her for the third time."

That was about the time that Jack was standing in shock at the patio doors with big eyes meaning it was time for me to leave. And to be fair, I'll give Jill the credit at this point because she does look good in that corset. Talk about showing off her hour glass figure, wow. So, I headed out, dressed as I am, and went to pick up the items on my list.

As I was driving to store, I re-ran the conversation Jill and I just had in my head and concluded that I may have seemed like a little too much of a sissy crossdresser than I feel that I am. I should have pushed back every time she said "fem boy" or sissy" and I needed to fix that. So, I sent her a text, plus I want to make sure they are using a condom. I mean, I don't want to stare at my house cleaner if her belly is bigger than her boobs.

"Are you using a condom?"

"Yes, should I save it for you?"

"Whoa, that's so sissy like."

"So, in a jar and in the refrigerator?"

"Hey, I pump aluminum foil every morning."

"LOL, I never heard that. I'll save them both for you sissy."

Alright, that didn't go as planned and I am making a mental note to disguise the jar and push it way towards the back of the refrigerator. That would be the last thing I need for Trudy to pull out of the refrigerator night.

But enough of that because here I am, at "We Be Parties" and I'm still showing from my episode and conversation with Jill. I think one of two things may happen while I'm strolling around the store. One, I get laughed out because I'm angled up and to the left and very visible or I get asked out. I think I will know for sure when I have someone help me load my new outdoor table into the back of my SUV. Which reminds me, I need to send Jill a text and ask for another favor tonight. I'll pay for his services, but the table comes in a box and requires a screwdriver and I already explained that broken nail issue, so I stirred up the pot and sent Jill another text.

"Can Jack come over after work and work my screwdriver?"

"Jack will not twist your screwdriver."

"I promise, I'll be in the shower."

"You will be out of the shower and dressed."

"Trudy needs help mixing the cookie batter."

"30 minutes and no more."

Hah, who needs a man around when Jack is available and his wife loves that cash. LOL, which means I need to stop by the clothing store for a minute and hit the AMT machine, probably twice. I should pick up extra nylons for Jill if she's really going to hold me to that "no jacking off in them" rule. And then get me something new to wear for tonight and for the date I'm about to get from the party supply store.

End Darby Dee Daniels 05

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