Adventures with Leslie Ch. 02

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Leslie has him help her chaperone the prom.
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Part 2 of the 25 part series

Updated 10/11/2022
Created 08/19/2007
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Chapter 02 -- The Prom

The week was flying by and I was feeling good about things. My weekend getting to know Leslie and convincing her to play the game was outstanding. I still think I have more power in this game than even I realize, but only time will truly tell that.

I was on my way home from work on Thursday night, thinking of nothing more than having a beer and watching the ballgame. When I heard my cell phone ringing as I drove, I figured those plans might change

"Hello," I picked up my cell.

"It's Penny," she said on the other end of the line.

"How are you my dear," I asked politely.

"I'm good, but this is not a social call," she informed me.

"It never is," I cemented. "Is everything alright?"

"Oh yes," she confirmed. "I am calling for Leslie. I have your first assignment in the new game."

"I figured," I jeered. "So what are we doing?"

"We aren't doing anything," she replied, sounding disappointed. "You need to get a tuxedo and meet Leslie at her house tomorrow night at 5:30pm sharp."

"Ok, I can handle that," I admitted. "Do you know what my 'assignment' actually is?"

"You will be chaperoning Mindy's high school prom," Penny revealed.

"Just me," I questioned.

"No, Leslie will be with you," she validated.

"Ok, then why didn't she call me herself," I inquired. "Emma always used to call herself."

"She wants to keep you guessing," Penny disclosed.

"Of course she does," I responded. "Well, thank you."

"Anytime, baby," she giggled. "If you do well on this one Leslie promised that the next assignment will be fun for everyone."

Before I could even ask if she knew what that meant, Penny hung up. That was the one part this game that always made me grind my teeth. The hanging up. They had all done it at one point or another. Ugh. So much for watching the ballgame.

I headed to the mall to rent a tux. It was a small chore, more an inconvenience really, but I got it done. I decided to get a hair cut while I was there, so I would look clean cut for Leslie. I finally headed home when all my errands were completed; I even took the time to pick up a corsage for Leslie, just to cover all my bases.

The next day dragged on, work sucked and there wasn't much else happening. Late in the day I changed into my tux in the men's room of our office and then packed up my stuff and headed to Leslie's. I parked in the driveway and headed up to the front door where I was greeted by a young, blonde haired guy also in a tux.

"You must be Miss Adams' date," he said to me, extending his hand.

"Yes, I am," I confirmed for him, shaking his hand. "And who might you be?"

"Oh, I'm Brad, Mindy's date," he divulged. "The ladies are still getting ready and they asked me to wait out here with you."

"It's nice to meet you Brad," I responded to him. "Are you a senior?"

"Yes, sir," he validated. "I'm headed to UCLA next year to play baseball."

"Really, that's great," I said, impressed. Having been a ballplayer myself, Brad's stock just went up. "What position do you play?"

"Third base," he revealed. "Batted .650 this season."

Brad and I talked baseball for the next 20 minutes or so as we waited on our dates. While we were talking, a long, black, stretch limo pulled up in front of Leslie's house. The driver stepped and saw us in our tuxes. He made his way over to where Brad and I were standing on the porch.

"Central High Prom," the driver questioned.

"Yes, sir," Brad answered him.

"Very good," the driver replied. "I'm Carl. I will be your driver for the night."

"Good to meet you Carl," I said, extending my hand to him.

Carl did not say anything as he shook my hand, in which a $50 bill was transferred to him. When the handshake ended Carl nodded.

"I understand there will be four passengers going and only two coming back," Carl announced.

"Yes, sir," Brad acknowledged. "Mindy and I will be going with some other people to the after prom party."

Interesting. Leslie and I would be returning alone. Nice touch.

A moment later the front door opened and Mindy emerged. She looked lovely, wearing a strapless maroon gown that fell all the way to the floor and was very big on the bottom. Her makeup was not overdone and her dirty blonde hair was done up. Her white shoulders drew attention to the pearls around her neck. She was a lovely girl.

"Aunt Leslie will be right out," she broadcasted as she passed by me.

She kissed Brad on the cheek and the head to the limo. Carl escorted them and opened the door for them. I stood on the porch and waited, corsage in hand. I felt 18 again myself for a moment, until I saw Leslie. She materialized from the house looking like no 18 year-old girl ever has.

She had on a glittery, electric blue mini dress with very thin strap and the bottom of which fell only to her mid thigh. She had on tan stockings which hid the scars on her inner thighs and matching electric blue 4 inch heels that made her legs look delicious. Her hair was done nicely, with curls at the bottom and her makeup was pronounced, especially the bright blue eye shadow and candy apple red lips.

I was in awe. She was gorgeous and hot. My cock started to twitch in my rent tux pants. I could not take my eyes off of her as she locked the house and made her way over to where I was standing.

"We're late, let's go," she barked.

"I got this for you," I said to her, as I shower her the corsage.

She stopped and sighed.

"Sorry," she asserted. "This isn't a date. We're chaperones."

"My mistake," I admitted.

Leslie then stuck out her hand for me to place the corsage on her wrist. Now I was confused, but then I remembered that my confusion was the goal of the game. I placed the corsage on her and she headed off towards the car. I followed submissively.

Carl held the door for Leslie to enter the limo and I watched her get in. Her ass was amazing in that dress and it seemed like she lingered in the door for a moment to ensure that I noticed. I climbed into the car behind and Carl closed the door.

Leslie had climbed into the seat on the far side of Mindy which left me to sit at the back of the car next to Brad. It was an interesting arrangement to say the least. She may have been new to the game, but she was good at it already. Mindy and Brad were excited for the evening as anyone their age should be. From the way Mindy was now speaking to me, I assumed Leslie and her had spoken about the current situation. Even though that was not confirmed for me, I felt relieved.

The just under twenty minute ride to the site of the prom was filled with small talk and bad jokes. We pulled into the parking lot of the Holiday Inn, where the sign read "Welcome Central High Class of 2007." That was a nice touch, I thought.

Carl opened the door and we exited the car. I stepped out first, followed by Brad. Carl then held his hand out to assist both Mindy and Leslie as the emerged into the early evening air. Mindy quickly took Brad's hand and headed inside. Leslie then walked towards me and I extended my elbow, offering her my arm.

"This still isn't a date," she reminded me.

"Of course not," I agreed. "We have work to do."

She then interlocked her arm with mine and we proceed to enter the hotel. We followed the well dressed students to the main ballroom, where the cocktail hour was going on. It was a classic scene, guys exchanging high fives while the girls were telling their friends how beautiful their dresses were and how awful the girls they did not like looked. There was even one girl in tears already. Ah, high school.

Leslie picked up her card on the way in, which indicated that we were at the faculty table. I was not looking forward to that, but I had no choice. I looked at Leslie, who was now smiling. She looked radiant until she noticed that I was looking and then her smile flat lined across her lips. She was one tough cookie.

We wandered around and Leslie made small talk with the parents and teachers she knew. The students were starting to dance and get a little rowdy. The DJ then announced that food was beginning to be served and we should be seated. Leslie found our table and we introduced ourselves to the faculty members and their spouses we were seated with.

The high ranking school official at our table was Ms. Marilyn Miller, the assistant principle. She was accompanied by her husband Bob. Marilyn was very complimentary and altogether too pleasant. Her focus stayed mostly on Leslie.

"Thank you so much again for doing this on short notice," she reinforced. "Mr. Peters would have loved to have been here, but his wife went into labor this morning. I guess he saw it coming."

Mr. Peters, it turns out, was the school principle. His wife was delivering their first child so the prom took a backseat, understandably. Our table had 3 other couples, all teachers and their spouses. I stayed quiet unless I had something clever to add, though often I think the table perceived me as a wiseass. As if I was not completely uncomfortable enough, just after dinner Mindy made her way over to our table.

"Hey sweetheart, are you having a good time," Leslie asked her niece. All eyes at the table were on the lovely young woman now standing next to her aunt.

"I guess," Mindy sighed. "I just came over to see if your date would dance with me since mine is busy with the boys."

I glanced past her and my embarrassment to see Brad laughing heartily with several other young men. I laughed to myself. In a room full of gorgeous young girls, these guys would rather talk to each other. They lacked vision.

Leslie digested her niece's request and then turned to me. I looked at her to read her face. I quickly stood up and played to my audience.

"Mindy, I would love to dance with you," I responded.

She grabbed my hand and led me to the dance floor. I could feel the eyes from my table burning holes in the back of my head with disgust at the thought that I said yes. Stuffy assholes.

I did my best to keep up with Mindy on the fast song that was playing when we hit the floor. I am not a great dancer but I gave a great effort. Thankfully for me, the DJ decided to slow it down as dinner was being served, though instead of returning to her table to eat, Mindy threw her arms around my neck for a slow dance.

I slowly placed on hand on her hip and took one of her hands from around my neck, to make our dance somewhat more appropriate. I looked at her and she appeared disappointed.

"You look lovely tonight," I complimented her.

"Thank you," she returned. "I am sorry about what I said to you last time you were at the house."

"You have every right to protect your aunt," I compromised.

"I know, but when she explained what was going on, I felt like an ass," she admitted.

"You were not an ass at all," I assured her. "Incidentally, what did she tell you?"

"Everything," she responded. "Leslie and I don't keep secrets."

"And what do you think," I asked, not wanting to give anything away.

"I think it's a tremendous concept," she replied. "Emma created something very interesting. I agree with you that this game could help save Leslie. I appreciate that you want to try."

"So she did tell you everything," I admitted, very surprised.

"Yes she did," she echoed. "Including that I would never be part of the game. A rule I plan to challenge."

As she said that she squeezed my butt. I was completely stunned by this move. I quickly moved her hand back up to my hip.

"Don't you think I'm pretty," she inquired as she batted her eye lashes at me.

"You are not part of the game," I repeated back to her.

"Let's change that," she quipped.

"Neither one of us make the rules," I informed her, wondering if that might be new information.

I was completely startled by a tap on my left shoulder. I turned to see Leslie staring back at me. She looked at Mindy who was smiling devilishly.

"Do you mind if I dance with my date," she asked her niece.

"Not at all," Mindy replied as she let go of me. "Thanks for the dance; I'm going to go peel Brad away from the boys."

Leslie seamlessly stepped in where Mindy had been almost a moment ago. She too wrapped her arms around my neck, but I was not about to move them. I swayed in rhythm with her, my hands on her hips.

"You have done very well tonight," she surveyed. "But Mindy is off limits."

"I had no doubt of that," I expressed. "And this is still not a date, right."

"Now you are catching on," she laughed. "But I do look good tonight."

"You will get no argument from me," I confirmed.

"How good do I look, would you say," she requested of me.

"You are sensuality come to life tonight," I proclaimed.

She stopped dancing and walked off the floor, headed for the ladies room. I returned to the table, unsure of what had just happened. When she returned, I sat next to her for the remainder of the evening, but she did not speak to me. She kept her attention focused elsewhere for the balance of the night. I sat, stone-faced, but confused, working hard not to show it.

The evening went nicely for the students, although Mindy was not named prom queen. That seemed to disappoint Leslie more than Mindy, which I understood instantly. I surprised myself there, unwrapping that situation so quickly in my mind. They were a unique pairing and I enjoyed watching them together.

As the evening began winding down, Mindy and Brad approached our table.

"We are heading out," she announced to us.

"Have fun and be safe tonight," Leslie said to her. She seemed vulnerable at that moment.

"I will," Mindy validated, with a look on her face that said "Trust me."

Mindy and Brad then headed off across the room to join a group of others headed to the post prom party. Ah to be young again, I was exhausted just watching them. We sat for another few minutes before Leslie stood and began saying goodbye to the people we were sitting with. I stood in silent obedience and followed her lead.

We headed out to the car where Carl was waiting. He opened the door and Leslie climbed immediately into the limo. I followed and sat immediately, not sure where Leslie and I stood. Carl shut the door behind me and returned to the driver's seat.

We pulled out of the hotel parking lot and Leslie put up the partition between us and Carl. She then climbed on top of me, kneeling on the seat. She looked deep into my eyes and then kissed me very passionately. We kissed for what seemed like hours, as if we were young lovers trying to devour each other. She finally pulled back and looked at me again.

"That was the sweetest, sexiest thing anyone has ever said to me," she admitted. "I almost threw you down and fucked you right there. A lesser mind would have just said I looked hot. Hell, several of the girls in the bathroom even said I looked like a slut. But you found a way to make me feel good about myself and safe. I just can't tell you what that did to me."

"I'm glad you liked what I said," I admitted. I smiled at her softly and she purred back at me.

"Do you know what the upside is," she fired back, "those girls were right. I am a slut. I never went to my own prom, so we are gonna make up for that right now."

I dropped the partition between us and Carl slightly.

"Carl, how much longer do we have the car for," I asked him.

"About 30 minutes sir," he announced.

"We are gonna need you to take it slow going home then," I requested.

"Yes sir," Carl stated as he closed the partition for us.

I ran my hands along Leslie's thighs and pushed her dress up as we kissed. I slid her skirt above her hip and firmly squeezed her ass as we locked tongues. I was hard a rock already and wanted her badly. I ran my hands over her thighs again and found the tops of her stockings. I then let my hands roam to her hips and searched for the waistband of her panties. She knew what I was looking for.

"They were so soaked after you said that, I had to get rid of them," she whispered in my ear before inserting her tongue into it. I knew my cock was spewing precum by the gallon at this point. Leslie wasted no time in reaching for the button my rented pants and ripping them open.

She worked them down just far enough to let my cock stand out. She then maneuvered herself on top of me so I could enter her flooded box. I was in heaven as she kissed me and worked her hips on top of me. My pole was embedded inside her as she ground her hips on top of mine. I was enjoying this very much when she stopped.

"Oh no," she yelled. "You're not getting off that easy. You are gonna fuck me right."

She then climbed off of me and onto the limo floor. She turned around and presented her ass to me. I got on my knees on the floor of the car and grabbed her hips hard.

"Fuck my pussy," she begged. "Give it to me good baby."

I positioned my cock at her opening again and thrust inside her forcefully. She yelped as I entered her. I could not hold back, I held her hips and rammed into her again. It felt so good to impale her with cock over and over. I was in ecstasy as she moaned and yelped.

"Pull my hair," she screamed. "Yank it until you cum inside me."

I grabbed a handful of her gorgeous black hair and pulled hard. I used her hair as leverage to pull myself into her over and over again. I crashed into her cunt for a few short moments before my cock started swelling. I pulled her hair even harder as I exploded inside her repeatedly. I kept ramming into her as each spurt of spunk filled her hole. When I was completely spent, I sat back on the seat and gazed at her cum filled pussy.

"That was great," she said, out of breath.

She returned to the seat next to me. I could not move. She lowered her dress and kicked her heels off onto the floor. She then tucked my cock back into my boxers and zipped up my pants. We sat there, silent, until the car came to a stop several moments later.

Carl came around and opened the door for us and I emerged from the car. I waited and assisted Leslie in getting out of the vehicle. She kissed me on the cheek and headed for the porch. I gave Carl another $100 tip for being such a professional.

I turned towards the house to see Leslie already standing in the front doorway.

"I'll call you," she shouted as she shut the front door.

I got in my car and headed home. This was a much different game, I thought.

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