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Kylie’s Valentines Day Dare

“I have to be in San Diego on the 14th,” Mark said. 

“What’s in San Diego?” Kylie asked half consciously toying with her hair.

“According to my boss?” Mark shrugged. “Genevar. They’re a Bio-Tech. Mostly for Oncology and Genetic disease research.”

Mark put his arms around Kylie, and added, “…but I was thinking it would be much better if you were there as well. Maybe you could fly in on Friday and we can spend the Weekend in La Jolla? I’ll take you to my favorite restaurant.” He suggested.

Kylie thought about her schedule. It was a nice idea, but no way would that work given her meetings…

Two weeks later Kylie landed in San Diego at sunset. The marinas and palm trees whipped by moments before touchdown. The sun was red over the Pacific Ocean, but by the time the plane arrived at the gate, a dark purple night sky had settled over the city.

She had the address to the restaurant. She would meet Mark there. Just a short Uber ride – only 15 minutes from the Airport.

Kylie wore a light blue dress. It was a classy outfit, but the hem was short. She knew Mark would like it since he always asked her to wear skimpy outfits.

The Uber arrived at the Restaurant, and Kylie looked at the sign hanging over the front door: “Lion’s Share.” The windows were set in a dark wood paneled facade, similar to a Pub in London, but with a bit of the West Coast trendiness to the decor once she stepped inside. 

The bar area was elegant, and featured craft liquor arranged artistically behind two smartly dressed bartenders in matching silver vests and ties. The place was busy, but not crowded. 

The walls had a stacked arrangement of dozens of paintings of Anthropomorphized animals engaged in random, but humorous, “human” activities. On her left was a portrait of a Lion standing in the pose of Napoleon with his right hand inside his vest coat. Another showed a giraffe questioning a cheating tiger in a poker game. Every square foot of wall space was covered in these paintings, and the doorways and windows were adorned with thick, red and purple velvet curtains. 

“Very sexy place”, she thought, scanning the faces of the people at the bar. Mark was seated at the far end talking to one of the bartenders.

“I’m not too late am I?” She asked, looking at her watch.

Mark smiled and kissed her lightly on the cheek. “Not at all, Jeff here was just about to get us our table. By the way, Jeff, this is my friend Jessica,” Mark said, introducing Kylie with the wrong name. 

Jeff the bartender nodded and smiled at Kylie. “We’ll get you guys set up in just a minute. What can I get you to drink Jessica?”

“Pinot Grigio,” Kylie said, and started to tell Jeff her correct name. “Actually, my name…” 

But Mark shook his head and stopped her. “Did you see all these incredible paintings?” Mark interrupted. “Jeff was just saying that the owner has even more of these at his house.”

Jeff knew Mark was up to something, but he was accustomed to it and played along. This wasn’t the first time Mark had brought one of his female friends by. “Yeah, actually some of the paintings in the back office are a bit … different.” He said in a dodgy, suggestive manner.

Kylie laughed back, she could tell these two knew each other pretty well but it did seem odd that Mark knew a bartender so well thousands of miles from home.

A few minutes later the hostess found them a table. It was a corner table at the back of the restaurant. The menu was the opposite of trendy. Or maybe it was trendy in its opposition to the trend? Dishes you wouldn’t normally expect like Boar and Random Wild Game Burger in a Boojey San Diego suburb on the water.

“Ok,” Kylie smiled cautiously. She knew Mark had some crazy sex idea he was going to make her do, and since today was February 14th, the BIG DAY, she felt herself getting wet anticipating what it would be. “What did you have in mind?” She asked melodically with a devious twinkle in her eye.

Mark’s gaze dawdled around the restaurant as he considered her question. “Are you wearing those red panties I bought you like I asked?”

Kylie flashed a conspiratorial smile, “yes, of course.” She said in a low, quiet but excited voice.

Mark grinned. “I’d like for you to go into the Ladies room, take them off, and then bring them to me,” he said.

Kylie rolled her eyes and looked around the restaurant. Her little dress would cover her well enough, but only just barely. The tables didn’t have tablecloths, and her legs were clearly visible to anyone in the restaurant who might be looking. 

She spotted the restrooms on the other side of the bar. Considering that worst case scenario, she didn’t know anyone in this town. Probably low-risk…

“Ok,” she said with a nervous voice. “But we have to be very low-key about this.”

Mark nodded and smiled, “Of course. Very low key.” His cock was already getting hard in anticipation, wondering how far she might be willing to go with this.

Kylie slid out of her chair, and strode coolly to the Ladies room. 

While she was gone, Mark fidgeted nervously with his napkin. The other patrons were completely unaware of their little game, but the thrill made him look around expectantly. 

Several minutes went by, and Mark started to become concerned. Maybe Kylie was having second thoughts. Maybe he shouldn’t have asked her to do that? 

“Anything I can get you while you wait, Mark?” Jeff, the bartender, had appeared out of nowhere.

Mark looked up, shaken from his thoughts. “Scotch,” he said. “Taliskar if you have it.”

“Yes, of course,” Jeff said, then, “Barrel Select or Storm?”

“Storm… neat please,” Mark replied and turned his gaze to the Ladies Room door. It certainly was taking Kylie quite a while to remove her panties.

Jeff disappeared and a minute later Kylie finally emerged from the restroom. Mark exhaled visibly with relief. Her hands were folded in front of her as she walked. And Mark could tell she clandestinely held something in her left hand. 

She smiled as she approached, her cheeks blushed. Nobody but Mark knew what she had in her hand, but he could tell she was excited about the little dare. Or maybe she just thought it was silly.

Of course it’s silly, he thought. His mind raced, thinking about what might happen. How many ways could this go?

Kylie approached Mark’s side of the table and surreptitiously pressed the balled up underwear into his hand.

Mark subtly looked into his hand under the table, confirmed that she had, in fact, given him her red panties and then smiled.

Kylie sat back down into her chair, “ok, I’ve completed my little dare,” she said softly. “Does that make you happy?”

Mark considered the question for a moment. “Completed?” He asked. “I don’t think you completed it yet, did you?”

“Well yes, of course, you asked me to bring you my panties, and I did it. You are holding them in your hand.” She whispered across the table.

“Oh, you mean these?” Mark asked and held them up slightly above the level of the table, and spreading them out to hold them by the waistband so that everyone who was looking in that direction could see. “I don’t think you completed it. But you definitely did the beginning.” He smiled suggestively, and placed the underwear on the table.

Kylie’s eyes widened, she started to say something and reached for her underwear, but Jeff had appeared silently at their side. “Taliskar,” he said, placing the glass with a measured pour of Single Malt on the table. Then his eyes fell down to the red panties on the table. “Neat,” he said, and his gaze darted to Kylie who sat blushing almost as red as the silky fabric in front of them.

Jeff took a moment to consider the scene in front of him. The unmentionable garment on display on the table, the blushing beautiful woman, and Mark sitting there looking like the cat that just ate the canary.

“Ma’am,” he asked with a sly smile. “Is there anything I can…” and his eyes slid smoothly back over to the panties. Then he paused, and said with a quick wink, “Is there anything I can get for you?” He asked suggestively. 

Kylie blushed further, averting her eyes from the flirty waiter. The fact that he was actually attractive heightened her embarrassment, but she recovered quickly. “I’ll have a Merlot.” She said quietly, and cleared her throat.

“Of course,” he said and then silently floated away. 

As soon as he had left, Kylie tried to grab her underwear, but Mark was able to snatch the panties before her hand could get across the table.

“No way!” Kylie exclaimed in a hushed voice. “Give them back. You can’t put them on the table!”

Mark chuckled and put the small garment in his pocket.

“Give it!” She demanded, smiling uncontrollably. 

“Ok,” said Mark. “I will. But you have to earn them back.”

“Now…” she said earnestly.

“Hmmm, no. If you want your underwear back then you’re going to need to finish your dare first.”

“I’ve finished my dare,” she said, turning beet red. And smiled. “That waiter knows exactly what we just did.” She whispered with a barely controlled and devilish smile. 

Mark laughed, sipped his Scotch and smiled. The night was just beginning.