Summer of 2K and 17 Challenge 04

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The challenge takes a quick trip to NOLA.
1.9k words
4.18
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Part 4 of the 4 part series

Updated 06/08/2023
Created 06/11/2017
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As we finish crossing Lake Ponchartrain, I hold up 3 cards. This is the travel version, with specific challenges.

You look at me, smiling, and take a card. The other 2 will be for the next 2 trips.

"Too easy." You say to me. "You might want to stop at an ATM now."

"Is it the $1000 dare?" I ask.

"Yep, and there is no better place to take your money than here in New Orleans." You say, smirking.

"Well, NOLA actually inspired this card, so I know I will enjoy. How about we raise the stakes a tad?" I ask.

"What do you have in mind?" You ask.

"So, the challenge is to flash me at as many places as possible, up to 10 total. For each picture I get of your exposed tits, ass, or pussy, you get $100 mad money. I'll give you $500 for a completely nude flash caught on camera. No time limit, but I need to get a good quality picture suitable for my Literotica bio page." I say with a serious look. I change them frequently.

"Any place of my choosing?" You say.

"Sure."

"Alright, but what's the catch? I'm not sure I trust your motives." You inquire.

"Well..."

"Shit, I knew it! Lay it on me." You say laughing.

"If you can't meet the $500 challenge before we leave, I get back half of the money you earned." I say.

"Ok, but I have a little stipulation myself." You say.

"Oh?"

"Yes, I get keep all of the money for any picture that has me flashing you with another person in the frame." You state.

"I can handle that, but I'm not going to count any picture of you simply flashing for beads. Those are a dime a dozen in this town." I counter.

"Deal. Shake." You hold out your hand.

I grab your hand, kiss it, and place on my pulsing member. All this talk has me anticipating a great 4 days here in NOLA.

We arrive too early to check into the hotel, so we head straight into the French Quarter and park in the pay lot by the river. From here, we can access some good places for lunch and get our tickets for the Preservation Hall concert this evening.

"Well, I better get a little more comfortable for these challenges." You say, as I park the car facing the wall near Café Du Monde.

"I'll make sure the luggage in the back is covered." I say as I turn off the Tahoe and grab my phone.

I open the back to double check the blanket on top of the luggage and Yeti. I see you kinda squirming in your seat.

"Close the back. Here's your first photo op!" You yell back at me.

I slam the back and pull my phone out of my front left pocket. I quickly swipe open the camera as I hear your door open. I stop in my tracks as I see you step out topless. I know my time is short. I lift my phone and begin focusing on your soft, supple features.

You step slightly forward to me, and close your door with your left hand behind your back. You never stop looking at me as I click away on my phone. In your right hand is your shirt.

Surprisingly, you don't just stand there. You back up to the wall. You place what I thought was just your shirt on the hood of the car. It's much bigger than that; probably a sun dress or something.

Then, you strip completely nude. Right there. You stand up against the wall once more, lifting your hands above your head. You turn around once so I can get a great picture of your delicious ass, and then you reach for the sundress and pull it over your head.

"Please send me one of the nude shots." You say.

I pick one and message it to her.

I quickly get a return message. "That will be $500, please."

And so we head onto Decatur Street. I'm craving some coffee and beignets. We always hit Café du Monde a few times on each visit.

It looks pretty full, but the takeout window line is manageable, so rather than wait for a table, we elect to take some to go. I get in line.

"I'll go find a park bench, or some place suitable to sit and enjoy our coffee." You say as you walk off in the direction of the shops just behind the café. The sidewalks don't look too busy, so this is probably a good plan.

I pay for our beignets and coffee and head in your direction. Something tells me to have my camera ready, so I balance both coffees in one hand while gripping the bag of beignets with my fingers.

There you are, on a bench facing Decatur. As I approach, you move to your right on the bench to make room for me. But then...

I lift my phone up and begin focusing on you. You turn your body to face me, and you lift your left leg up giving me a view of your wet deliciousness. I click away. Your perfectly edible pussy is clearly showing as you pretend to tie your shoe on your raised foot.

Somehow, I had stopped walking. I catch myself staring a little, and realize I better keep moving toward you.

I deliver the beignets and coffee to you as you lower your leg to make room for me.

"Do you want me to send you that picture, as well?" I ask.

"No. That will be $100." You say leaning over to kiss some of the powdered sugar off my lips.

Damn! Not only did she cover the $500 challenge, I'm out $600 so far.

Harrah's is suddenly looking very far away, both physically and fiscally.

The walk to the French Market is a pleasant one. Even here in June, the crowds along Decatur are delicious. You can hear all types of languages and accents; truly one of our favorite parts. And we know from experience, as the heat and humidity increases, so too will the amount of visible skin. It is a target rich environment to say the least.

I come to my senses as I realize something. You have no underwear under that dress. You had stripped down in the parking lot and only put on the dress and some sandals. I better take in this sight before we head to the hotel.

As we walk, I move a little away from you and hold up my phone. I set the camera to record and I begin panning around the street as we walk. I settle my filming upon you. You smile at me. I smile back, and point the camera down.

What I see is simply astonishing. I know every inch of your body, so it is easy to see the gentle swaying of your breasts, unencumbered by a bra. They move every so slightly as you walk. The material of the dress clings perfectly to every inch of you.

We move thru the market, taking in the sounds while we peruse the various offerings of the hundreds of vendors. We have seen it all before, but you never know if a new treasure might pop up. Also, we'll be back later before we leave, so this is an expeditionary mission of sorts.

As we approach the end of the market area, we notice the last bit of sidewalk has many more vendors than the last time we visited. And then I see it. Just past the guy selling wigs, there is a larger kiosk selling dresses. And it has a changing room. Man, I'm about to be $500 poorer. This isn't working out.

I stop to peek at sunglasses while my wife walks ahead straight for the dresses.

The dresses are actually not very remarkable. However, the changing room is. It is just a curtained off corner of the kiosk, without even a top to it. As I am checking out the changing room from afar, she comes back into view with a dress in her right hand and a grin on her face.

I get my phone out and approach the stand. So, these guys have set up a stand with 3 walls. Dresses hang all over the walls and there are a couple of racks in the middle.

I walk up and take a picture of her holding the dress up.

"I'm going to try it on. It is nice and light and perfect for this weather." She says, turning to walk to the changing room.

She slips inside, and pulls the curtain behind her.

I see her hands go up in the air above the curtain as she removes her dress over her head. Then, I see her holding her phone ever so slightly up, level to the top of the curtain.

My phone buzzes as I see her hands go up one more time to bring the new dress down onto her body.

It's a text from her, with a selfie of herself, naked in the changing room. I can see the tops of her nipples sticking out and her feet, and not much else. It's a pretty tight space. Still, it's a glorious picture.

As I am staring at it, she walks out in the dress. It's a tad shorter than the one she was wearing, but the straps are much thinner, thus accentuating her shoulders. I like it, and she can tell from the look in my eye.

"I really like that. Is it comfortable?" I ask.

"It's perfect. I think I'll buy it to wear tomorrow." She answers.

She heads back into the changing room.

"Let me have it so I can pay for it." I tell her.

I walk up to the changing room, camera in hand. She closes the curtain.

I slightly pull the curtain open and hold the phone up to capture a video. She obliges by pulling the new dress over her head. Now, I have a better shot of her naked in this little space.

She hands me the dress, then turns around.

"Take a picture of this!!!" She whispers with effect.

She bends over, showing me her asshole and pussy. She grabs both her cheeks and spreads wide open for me and the pictures are taken.

I can't wait. I quickly lick my right index finger and shove it in her ass. Just a quickly, I pull it out.

Then, holding the curtain in my left hand, I pretend to drop the dress. I bend over to pick it up, but with my face right in between her cheeks, I am able to lick her pussy quickly, gliding up to her ass.

That takes barely 10 seconds.

I turned to walk to the cash register. I handed the dress over. In doing so, I looked to my left at the dressing room.

This is going to sound cliché, but the curtain was opened just enough for me to catch a view of her sideboob as she put the dress back down over her naked body.

I smirked as she walked out.

"What?" She said, succinctly.

"We are definitely coming back to this little stand." I answered.

"We actually are changing inventory tonight. There will be new racks filled with summer clothes by this time tomorrow. We just cleared out our formal stuff last night. I hope you come back." the clerk volunteers.

Not that the thankful clerk would know, but that this dress actually cost me $500.

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Sailman66Sailman66over 6 years ago
A fun series

A great short story series you have shared. The possibilities for so many other challenges are numerous so gives you plenty of scope for future additions. Enjoyed them all.

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