An Adventure with Megan

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How I broke the heart of a skank.
5.9k words
13.4k
1

Part 1 of the 2 part series

Updated 09/22/2022
Created 01/09/2014
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This story is 100% true. Only the girl's name has been changed; enjoy.

*

After the memorable time in Nashville I couldn't wait to get back to civilization. Three months passed before I returned to Hawaii. The year long deployment in Afghanistan sucked but was finally over. Everyone in the Battalion was counting down the minutes until they could see their families. I was counting down the minutes until I could fuck the girl I left behind when I was deployed. Every second seemed like agony for my dick.

Eventually, my Battalion finished inventory of all essential items and we were released for a three day weekend with a promise of a month off after one week of work. I was a 21 year old soldier with lots of money and freedom to do whatever I wanted. What did I do during my time back? I fucked Megan, blew cash, and flew Dustin's dumb ass out to Hawaii for a week.

"Hey, we're done," I said to Megan on a borrowed cell phone. She had been waiting a year for that call. Megan asked, "where should I meet you?"

"Meet me by the front gate," I answered with sincere excitement.

"Okay."

I gave my penis a pep talk after hanging up. It had been several months since banging the grandmother and my dick was ready to rip a hole through my uniform. I grabbed a change of clothes and walked quickly to the front gate. A beautiful woman waved at me as I left the military base. Her light blue eyes and brilliant bright smile were framed by shoulder-length black hair. When I left she was thick. The year apart changed her in all the right ways. Her narrow hips and long legs were barely covered by a short white tennis skirt. The matching top was cut low making her large C cup tits shine on display. Megan had lost weight everywhere except her boobs and ass. Truthfully, I was awestruck by the woman I had left behind.

"Baby!" Megan cried as she rushed from her car to hug me.

Her high heels clacked on the pavement as she ran into my arms. I felt her breasts press firmly against my chest as we embraced. It took military strength discipline to keep me from fucking her on the hood of her car.

"Hey sexy, you ready to get out of here?" I said anxious to get as far away from the military base as possible.

Megan walked back towards her silver Audi convertible.

"I got us a hotel room so we can be alone for the next few days," she told me.

I knew what that meant. She didn't want her neighbors hearing the moans and screams. She must have realized I planned on punishing that pussy for the next 48 hours straight.

We drove to Waikiki at 90 miles per hour. I groped her body the entire drive. Her little Audi passed traffic quickly as we raced our hormones to the hotel. Her wet panties gave away her intentions as much as my hard on.

We pulled up to the valet stand at the hotel after what seemed like an eternity. She threw her keys to the valet and took the parking receipt. I followed her inside. The thought of check-in was instantly erased as she showed me the room key. Bitch had planned ahead. That's a first! As the elevator doors closed I pushed Megan back against the wall and kissed her passionately. Our kiss didn't end until the elevator stopped near the top. She led the way to the room. I stared at her ass which was barely covered by the short tennis skirt. When she opened the door my heart skipped a beat. It was the biggest hotel room I had ever seen. The custom couches and plush chairs were artfully placed in all three rooms. The spacious king sized bed was covered with an expensive down comforter which felt like lying on a cloud.

"How the hell did you pay for this?" I asked in an astonished tone.

She giggled as she answered, "I have a really good job."

"Are you stripping?" I asked.

"No, way better than that," she answered.

I was curious what it was but I had more important thoughts invading my mind.

I pushed her back onto the bed then took off my shirt. Megan slid her manicured nails lightly down my chest. I watched the smile slip across her lips as she anticipated the next few hours. (You perverts are probably on the verge of jacking off aren't you?)

Fast forward three hours and several bottles of water!

We both laid on the bed sweaty and exhausted. Memories of orgasms lingered in the air.

"Are you hungry baby?" She asked me after she caught her breath.

"Yeah," I answered wiping sweat from my face.

"Let's go get something to eat then we can come back here," she said without moving.

"Sounds good," I replied.

It took another five minutes before either one of us had enough energy to move.

After a quick shower, we left the hotel and walked along the beach talking. The sound of crashing waves inflicted a surreal sense of reflection as we looked for a place to eat. She was in the same sexy outfit. Every time I looked at her I felt my hormones spike again.

Megan watched the sun set as I watched her tits. I definitely had the better view.

"Want to go to Duke's?" She asked as we reached an area crowded with romantic restaurants.

"Sure."

Duke's was one of the oldest and best known restaurants in Waikiki. The hour long wait was worth the food and drinks we ordered. Megan was only 20 but her fake i.d. said she was 22. The year away from constant drinking had lowered my tolerance enough that I was drunk after only three long island iced teas. I eventually switched to beer so I wouldn't pass out. She kept pounding different drinks the entire meal like a pro.

The steak I ordered was amazing and her cleavage was the perfect entertainment to go along with the meal. It was hard to imagine a better evening after enjoying a hot bitch, great food, and Hawaiian scenery. However, it got much better. I didn't have to pay for the meal! When the $180 check arrived she grabbed it quickly.

"I got it baby," Megan said casually.

"I have plenty money. I'll get it," I said reaching for it.

She laughed, "I know you do baby, but I don't mind."

She opened her designer purse and pulled out a stack of hundreds. My mouth fell open. She easily had a few thousand in cash.

"Where the hell did you get all of that money?" I asked in disbelief.

She answered, "I just have a great job."

"What's your job?" I questioned quickly.

"I'm a personal assistant to an escort," she said paying the check plus a great tip.

"How are you making that much money working for a hooker?" I asked shaking my head.

Megan looked offended. She replied in a serious tone; "she's an escort. Hooker is a mean term."

"Sorry," I said laughing. I didn't realize there was a whore code. "So why is she paying you so much?"

"Because I book her appointments and post ads for her," she said seriously.

"You're her pimp!" I responded loud enough that couples sitting around us noticed.

"I am not," she replied in a hushed whisper.

"The hell you're not."

I was dating a pimp...or so I thought.

Megan shook her head and changed the conversation. I let it die. I didn't want to jeopardize my chances for sex.

We walked back on the dark beach. We were both eager to get to the room and attack each other. She kept asking about Afghanistan but I avoided the questions. It was the last thing I wanted to think about.

We eventually got back to the hotel and were ready for some fun. Her shirt and bra was on the floor before the room door closed completely.

"Want to make this even more fun?" Megan asked with a smile.

"Sure, what do you have in mind?"

She pulled out her cell phone and started scrolling through her contacts, "let's have a threesome."

"Seriously?"

"Yeah," Megan said briefly as she put the phone up to her ear.

"Hi, is this Destiny?" Megan said into the phone.

"You know a girl named Destiny?"

Megan looked at me with a smirk, "she's an escort."

I started laughing so hard that Megan had to walk onto the balcony to hear Destiny speak. I laid on the bed and waited. Several minutes later Megan walked back into the room.

"She's busy tonight, but we have a date with her tomorrow afternoon," Megan said setting down her phone.

"Sweet!" I took off my shirt, "we can have fun together until then."

She lifted her skirt and pulled down her red panties. Then she walked to the bed for round two. (Stop getting off perverts!)

The next two days were a blur of sex, alcohol, and great food. Unfortunately, after the short pass I had a week of military welcome back bullshit. The days were spent getting medical tests and paperwork done. The nights were spent exploring new sexual positions with Megan. At one point, a Staff Sergeant commented on the rope burns across my wrists. I laughed and acted like they weren't there. The week ended with the Company Commander giving us a speech about being mature. Yeah fucking right! I ran to my barracks room after he finished and grabbed a duffel bag full of clothes then hurried off base. A month of sex and partying sounded like heaven.

Megan picked me up in her Audi and we sped towards her large Honolulu apartment. She refused to explain how she could afford it. I didn't care as long as she gave me a place to crash and pussy anytime.

We got to her apartment in record time and were met by her furry little terrier when we walked inside. It bounced around barking as soon as she opened the front door.

"Bowser!" She shrieked happily picking the dog up. "I love you Bowser."

I put my bag next to her closet then said; "set it down so we can go eat."

"Okay, I love you Bowser," she giggled hugging the terrier.

"Want to party tonight?" Megan asked as we walked to a sushi restaurant.

I shrugged, "what do you have in mind?"

"I can get us some party favors if you want, baby."

"Like what?"

"Coke," she replied nervously.

I shook my head, "no, I'm good. Not really a big fan."

"Is it bad if I do it?" She asked looking at me.

"No, go for it," I responded as we waited to be seated. I don't care if bitches do drugs around me as long as they put out.

"Are you sure?" Megan asked curiously.

I looked at her and saw a worried expression cross her face before I responded, "Megan, I seriously don't care. You should do it if you think it will make tonight more fun."

"Awesome," she said texting furiously on her phone.

After we ate we walked to her car and drove to a bar several miles away. A sexy little Asian girl with big fake tits was waiting outside when we pulled up. She waved at Megan. She handed me the cocaine then Megan handed her the money. I didn't know it at the time but drugs are easy to find in Hawaii. Good luck if you're a tourist though. Locals hate tourists.

Just to make it clear, I don't use cocaine. This isn't some sentimental story about drugs being bad or me being above them. I just prefer pussy and alcohol. We returned to her apartment 20 minutes later. I dropped onto the couch and turned on the television as she grabbed me a beer. I barely paid attention to her as she chopped up the white powder and looked for a straw.

Megan snorted her first thick line and smiled as she flopped back onto the chair. After a few minutes she stood up and took off her shirt seductively. "Baby, I like to fuck when I do coke," her voice trailed off as she undid her tight denim shorts.

My eyes went wide as the shorts slid off her hips and fell to the floor. She bit her lip and waited for my reaction.

"Hell yeah!"

I threw the remote behind me and pounced on her happily.

The next few hours became a kinky sex marathon. We only stopped for coke or beer breaks.

"Baby we need to take a break," Megan said panting for breath as my hands roamed across her body. I could only nod because I was too tired to talk. We walked back to the couch and she grabbed her coke baggy then looked at me with a devious grin.

"Baby I have a fantasy," she breathed with a devilish smile.

"Wait until I catch my breath," I groaned.

She laughed for a full minute before she replied, "don't worry baby all you have to do is stand there."

I looked at her and shrugged, "what is it?"

"Come over here," Megan said smirking again.

I walked to her hoping I had enough bodily fluids. She dropped to her knees and started caressing my dick with her mouth and tongue. Her hand worked with her lips to get me hard.

"I like your fantasies," I commented watching her.

She giggled on my cock almost making her gag, but she continued until I was completely hard. Then she stopped.

"Okay stand there," Megan said.

She held my cock with one hand as she grabbed the tiny coke covered mirror with the other.

"Hold still," Megan said obviously concentrating.

I continued to watch as she pushed some white powder from the mirror onto my dick. When she was certain it was enough she sat the mirror down and grabbed her straw and my beer.

"Here baby," she said as she handed me the bottle.

She arranged the coke into a thick line on my shaft then snorted it quickly with the straw. I did the only thing I could think of at the time. I took a drink of beer and stared at her tits.

"Was that hot?" She asked after licking my cock clean.

"If I say yes will you do it again?"

She nodded, "I would love too."

I finished my beer as my cell phone rang.

"Hey mother fucker! How the fuck are you?" Dustin's voice echoed through the phone with enthusiasm.

"I'm great you son of a bitch. I bet you'll never guess what just happened."

He laughed as I told him about Megan's coke and cock fantasy.

"Brother, I wish I could go to Hawaii. I want to party with you again," Dustin said sadly.

"Dude, why don't you fly your ass out here?"

"I can't afford to do that brother."

"If I buy a ticket will you come out?" I asked.

"If I can get off work," Dustin answered.

"How long do you need to request off of work?"

"I need two weeks' notice," he said realizing it might happen.

"Turn in the form tomorrow. We're booking your ticket tonight," I said walking to Megan's computer.

She followed me listening to the conversation. She was excited to meet the man who had been involved in so many of my twisted stories. I tried to talk to Dustin and type on the computer at the same time until Megan decided to help.

"Move over baby I'll look it up," Megan said pushing me out of the way.

I stood up and let her type as I joked with Dustin about all the crazy things we could do once he arrived. I promised to take him surfing and he promised to be the craziest I have ever seen him.

"I found a ticket for 900 dollars," Megan said after a few minutes of typing.

"What's the date?" I asked.

"Give me the phone baby," she said reaching for it.

I handed it over and wandered back to the kitchen for another beer. She spoke to him for a few minutes. When I walked back into the room she handed me the phone with Dustin still on the line.

"Dude, she just bought my ticket," he said astonished.

"What?" I asked quickly. "Megan did you buy his ticket already?"

"Yeah, don't worry about it," she said surfing a designer website for purses.

I was shocked, "how the hell can you afford that."

She shrugged but didn't answer.

"Just let her pay for it. If bitch has the money then let her waste it," Dustin said seriously.

"Guess you're right but I have no idea how she has so much money," I said walking towards the bathroom to take a piss.

"Well brother, I'll see you in two weeks!"

We hung up.

"How can you afford to do that?" I asked when I was done peeing and back in the bedroom.

"I love you. I can afford the ticket. Don't worry about it," she replied.

I tossed the phone onto the bed and grabbed my beer. Before I could ask another question she was naked and straddling my lap. Dustin was coming to visit and neither one of us had to pay for it, so I didn't complain.

Megan answered a call the next night after sunset and walked quickly into the other room. She walked back into the bedroom a few minutes later. She grabbed her bag and walked to her closet.

"What are you doing?" I asked casually.

She glanced back over her shoulder as she answered, "I'm going into work for a little bit honey. We can go eat when I get back."

I watched as she grabbed a few skirts and a sexy top. She rushed out the door before I could ask where she was going.

After she left I got bored and decided it was a perfect chance to explore Waikiki by myself. I ended up pounding shots at a shady strip club three hours later. My cell phone vibrated in my pocket several times before I realized Megan was trying to call me.

"Hello?" I answered loudly.

"Baby, where are you?" Megan shouted back through the phone.

"Getting drunk in a strip club," I yelled.

"Which one? I'll come join you."

I looked around trying to remember the name, "the one closest to your place. I don't remember the name. It's fucking nasty."

"Okay, I know which one you're talking about. I'll be there in 20 minutes." I hung up and ordered another shot.

Three shots and several strippers later Megan arrived.

She hugged me, "hey lover, you look hammered."

My slurred hello gave it away quickly.

"Having fun staring at the girls?" She asked with a devilish grin.

I nodded since I was too drunk to talk.

She looked around then looked back at me, "which ones do you think are hot?"

I glanced around trying to find the one I had been eye fucking all night. I pointed at her when she walked out from a back room. Her long blonde hair covered her big fake tits. She was my type of slut. The blank look in her eyes made it obvious.

"Her?" Megan asked giggling. I expected her to get angry however; she walked casually over to the stripper and started a conversation. Surprisingly, they both walked back to me and the stripper sat on my lap while Megan sat across from us.

"I hear you think I'm sexy," The stripper said tracing her finger down my chest. "My name is Cinnamon."

"My name is Bob," I stammered drunk. Her laughter made it obvious that I wasn't doing a good job of acting sober.

"Well your girlfriend wants me to give you a lap dance, is that okay?"

I happily nodded then sat back.

Cinnamon was worth every dime I never spent on her. She grinded her hips matching every bass beat blasting from a random rap song. Her perky tits swayed hypnotically. I glanced at Megan during the second song expecting her to be watching me, but I was pleasantly surprised to see her eyes following Cinnamon's ass. After the third song Cinnamon stood up and kissed my cheek.

"Thanks sexy," she whispered into my ear.

Megan handed her a wad of cash.

"And thank you too," Cinnamon said seductively kissing Megan on the lips. Megan arched her back as their tongues played against each other. Megan picked me up and helped me stumble back to her apartment. I fell asleep as soon as she dropped me onto the bed.

The next week felt like déjà vu. We ate at fancy restaurants, fucked like rabbits, and Megan would disappear for a few hours at a time. When I asked questions about where she went I received vague answers, but I never pushed the issue. That is until four days before Dustin flew into Hawaii.

Megan left suddenly. I was in her apartment alone. I opened her computer eagerly looking up things to do when Dustin arrived. I looked at her favorites list and saw several escort rating sites. I figured she was looking up ratings for new girls to pimp out. I shouldn't have given a fuck, but I was curious. One name was repeatedly clicked. The name was NaVa. I clicked on the reviews and read what some of the men were saying. What I saw made me laugh. They had described Megan perfectly right down to her tattoos.

The mystery of her money suddenly became clear. I guess I should have been hurt, but I was ecstatic at the thought of dating a hooker. Another amazing thought crossed my mind. She kept paying for my things then fucking me for free. Did that make me a pseudo-pimp? I closed the page and kept chuckling while I called Dustin with the good news.

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