Kelly

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Josh needed an adventure.
8.7k words
4.74
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Part 1 of the 2 part series

Updated 06/07/2023
Created 03/23/2016
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Fresh out of a relationship, at 27-years old, I found myself in the middle of what appeared to be a mid-life crisis. I know, I know; the whole idea of a "mid-life" crisis, is that it's supposed to happen in the middle of your life. Typically in your forties, or at least that's how it was with most men and women who went through that stage. For me though, it was happening much sooner.

I had spent the last six years with my now ex-girlfriend, Amber. I had also spent the last six years, working full-time at a supermarket, and was on the verge of becoming a manager for the grocery department. What went wrong? I'm not entirely sure, to be honest with you. One day I was happy, and the next...everything just seemed wrong to me. Starting with my relationship with Amber, everything just started turning sour, one by one.

With Amber, our sex life was suffering a great deal. It wasn't that I didn't have any interest in her, believe me. The problem with that, was on her end and her end only. For some reason, she just did not seem to be as attracted to me sexually, as she had been before. It wasn't just sex though; no, it was more then that. She had stopped showing me any form of affection.

She hated making out, and if I even so much as tried to hug her in public, she would seem annoyed and pissy with me. It got to a point, where I was fed up with it, because it honestly hurt.

The fact of the matter was, she wasn't running around behind my back. She wasn't cheating on me with some dude, like most people would have assumed a girl was doing, if they were acting the way that Amber was acting. No, I would find out that she had remained completely faithful to me, in spite of her lack of interest. I later found out, it was just that; a lack of interest.

The spark had just worn out, and neither of us really knew how to re-ignite it. So, after a long conversation about everything that she felt, it was decided that it was for the best that we go our separate ways. Or atleast, that's what Amber said; I didn't exactly agree, though. It really didn't matter what I felt though, because the next morning she was on her way out the door, with all of her personal belongings packed and ready to go along with her.

Shortly there after, everything else started to fall apart too. I developed a feeling of discontent with my job. I had been satisfied with where I was for so long, that when I sat down one day and realized how much I hated being there...I was shocked. I hated everything about this place, from the customers to my managers and even my co-workers. The pay was shitty, and I felt like I was so much better then a management position, at a shitty supermarket. There had to be something better for me.

Slipping into a depression, I found myself not really going out anywhere, to often anymore. I would go to work, come home, have a few drinks and call it a night; that was it, really. As a result of this, certain friendships began to suffer as well. People stopped calling me, because they could never reach me and they had also gotten a bit tired of never seeing me outside anymore.

The biggest problem out of all of these things, was simple; what the hell was I going to do, to change the things that I hated?

Clearly, change was necessary; I didn't know how though. I hated my job, but what would I rather be doing?

I decided that I needed to step away for a while, even if just a couple of days, and take a deep breath. I needed a REALLY deep breath though, and that's why I decided not to even tell anyone that I was leaving; I just did it, and that was that.

I grabbed my car keys one day, walked out the front door, got in the car and started the engine. I sat there for a few minutes, trying to figure out where exactly I wanted to go. Somewhere, out of the city; out of the state, even. Just where?

Wildwood, New Jersey.

I decided that it was a beautiful, warm and sunny day and the best place that I could go, was Wildwood. I loved it out there, and had been going every summer since I was a kid. Sometimes for a few days, sometimes for a couple of weeks at a time. I figured, some time away from the city, and spent on the beach by the ocean, just might do me some real good. So, Wildwood it was.

What awaited me there, was a girl named Kelly; wild, and crazy Kelly.

When I first arrived there, I pulled up outside of a motel room and decided to see if they had any vacant rooms available. I had already made up my mind, I wanted to stay out here for at least a couple of days. So, I was obviously going to need a room. I had brought enough money with me, for at least three days in a motel, and also enough to eat and spend on the boardwalk.

After checking in and paying, I went to the room they assigned me and took a quick shower. Washing up nice and good, I then made my way outside to take in the scenary. There were people out on the balcony, and in the pool as well; everyone was having a great time. The smell of the ocean air, mixed with the wide variety of fried and delicious foods from the boardwalk was driving me crazy.

I locked up the room, and started walking towards the boards, my first stop being the arcade.

I spent a good hour in the arcade, before heading out and stopping at my favorite boardwalk Pizza shop; Sam's Pizza Palace. One large plain slice, and a large soda later, and I was walking down onto the beach. I sat there for a while, admiring the beauty of the ocean and the sunset. It was relaxing...I had definitely made the right decision, coming here like this.

The fact that no one knew where I was, was a good thought too. Not that I thought anyone would call to check on me anyway, but if they did, I had left my phone at home and would not have to worry about being bothered. All I wanted, was to be alone for a while.

Once the sun had set, I turned my attention back to the boardwalk and after a while, I was standing in front of a club. In the mood for a couple of drinks, I showed the bouncer my ID and paid the entree fee, before walking inside.

The bass was pounding, with your typical club music blaring through the speakers. The strobe lights were flashing, and were sure to give anyone with epilepsy a major seizure; thankfully, I didn't need to worry about that, myself.

I walked directly to the bar, pushing carefully through the crowd of people on the dance floor. Sitting down, I ordered a beer and waited patiently as the bar tender dealt with a few other customers before fetching my drink.

As I sat there waiting, I looked around at my surroundings. Something seemed...different, about this place, from most other bars and clubs. Something I hadn't quite noticed when I first walked into the building, was that the dance floor seemed to consist of guys, dancing with other guys and girls dancing with other girls. Not exactly, your typical crowd, I thought to myself.

It took a few moments, and as the bar tender sat my beer down in front of me and waited for me to snap out of my trance and pay him, it finally clicked. This was a gay club. I had just walked into a gay club, without even realizing; how could I have not noticed?

"That'll be $3.50," the bar tender said, snapping me out of my train of thought.

"Huh? Oh...s-sorry," I said, handing him the money for my beer.

He walked away to break the five dollar bill I had handed him, and I continued glancing around at my surroundings. As I sat there taking in everything that I saw, and still trying to figure out how I had failed to realize this was a gay club, my eyes crossed paths with the eyes of the most beautiful girl I had ever seen.

She was sitting across the bar from me, and her eyes were locked with mine, the sexiest smile I had ever seen on her face. She had short hair, dyed hot pink and her lip was pierced. Her eyes were green, and absolutely mesmerizing. She wore a white tank top, that showed off some very nice cleavage, and a pair of very short, shorts.

I looked away finally, after what felt like a really long time of staring at her; I didn't want to seem like a pervert or something. That's when it dawned on me; she had been looking back at me, the same way I had been looking at her. The thing is, we were in a gay club, and she was checking me out which made no sense, since clearly if she was here that had to mean she wasn't into guys. Unless, she had popped in here by mistake, just the same as I had...could that really have happened?

Could I really, not be the only fool, to not notice what type of crowd this place catered to?

Who knew for sure, but I wasn't going to focus to much on it.

I was here, not gay, but not going to make a huge deal of it...a few drinks, and I would head back to the motel for the night. That's when I noticed the girl standing up, and walking towards me...towards me? She was coming over to me, with a big grin on her face as she moved slowly through the crowd of people. She stopped finally, right beside me and placed her hand on my shoulder.

"Mind if I sit next to you?"

I was stunned; she was speaking to me. I hadn't expected her to actually come over and try to spark up a conversation with me, like this. Yet, here we were, side by side with her asking if it was alright to sit down next to me.

"Uh...y-yeah, sure! No one else is sitting there, so sure."

I pulled the seat out for her, and she thanked me, and sat down. I had finished my first beer, and she seemed to take note. She waved the bar tender over, and reached for her purse.

"I'll have a bloody mary...and another beer for the cutie right here," she said, motioning towards me.

The bar tender left to fix us our drinks, and she smiled at me again.

"Thanks," I said. "You didn't have to do that."

"It's alright. I really don't mind. I'm Kelly; and you are?"

She reached out to shake my hand, and I accepted the greeting, shaking hands with her and told her my name.

"I'm Josh."

"So, Josh; are you here by yourself?"

"Uh...yeah, yeah. I'm staying at a motel nearby."

"You come out to Wildwood on your own, often?"

"Not really," I said, as the bar tender showed up again with our drinks.

"I was just...looking to get away from home for a bit."

"Ah, I see. And where is home, if you don't mind me asking?"

"Philly," I said.

"Northeast. I've been going through some shit lately and just...wanted to get away for a bit. Nobody back there even knows where I am right now."

"Pulled the old disappearing act, huh? Spontaneous; I like that."

"Yeah, well...I just didn't want anyone bugging me."

We continued talking for a while. Apparently, Kelly was here with a few friends of hers, who were in the dance crowd at the moment. They were staying at a motel a few blocks away from the one where I was, and would be here for about a week. Kelly was a few years younger then me, twenty one years old to be exact. She was a wild, spontaneous, kinky, sexy, punk rock chick who loved to have a good time. I would come to find out, she was also a transsexual.

I was surprised, since she really didn't look like she had ever been a man at all; it didn't change my thoughts on her though, and I still wanted to hang and talk.

It was around eleven o'clock, and we were both feeling a really nice buzz. I had spilled my guts about a lot of the drama going on back home, and most girls probably would have turned away, annoyed at such openness; Kelly didn't mind at all, though.

Finally, Kelly stood up, staggering just a bit on her high heels, and I caught her before she fell. She giggled, and grinned at me.

"I'm about to get out of here, with my friends; you should come with us. We're gonna go for sort of a joy ride around the town, and just do whatever comes our way."

It sounded crazy. It was already running kind of late, and I hadn't planned on being out all night, really. I was having a really good time so far though, and didn't exactly want it to end.

"I'm not sure," I said, a little reluctant.

"I was gonna go visit a friend of mine who lives nearby, tomorrow. I was hoping to catch some sleep, before I do."

"Oh, come on now Josh," she said, whining as she gave me a playful shove. "Is it past your bed time?"

"No, I don't have a bed time baby," I said, laughing.

"No? Well, then you shouldn't have a problem coming out with me, and my girls to have some more fun."

"You know what," I said, standing up on wobbly legs.

"Why the hell not; let's go."

"That a boy," she said, giving me a big hug and a peck on the cheek.

"Let's go have some fun on the town!"

Kelly took me by the hand, and led me towards the exit. When we got outside, we were greeted by three other girls...who I assumed were probably transsexuals as well. There was one, who was pretty tall, probably about 6'2" with long red hair and blue eyes. She wore a leopard print shirt, showing off plenty of cleavage, just like Kelly. She was wearing skin tight jeans, and high heels. To the left of her, was a shorter girl; the closer I looked at this one, the more I imagined that she could possibly be a regular girl.

Her facial features were a bit more petite, and she had a nice set of tits, too. Her ass was perfect.

Standing a few feet away from them, on her cell phone was a girl wearing a black shirt and black pair of jeans. She had long hair, dyed dark blue, green eyes like Kelly, and a nose piercing.

"Kelly," said the taller of the three. "Are you ready to go, babe?"

"I'm ready when you are; mind if I bring my new friend?"

The girls turned around, and looked towards me, and I could suddenly feel their eyes, sizing me up from head to toe.

"Why not," said the tall one. "He's cute. And the more, the merrier. What's your name, cutie?"

"Josh," I said, introducing myself.

"Josh; well, I'm Tara. This is my cousin, Michelle," she said, pointing to the shorter girl who I was sure was a genetic girl.

"And the one over on her phone, is Jenny."

"Nice to meet you," Jenny and Michelle both said, at the same time.

"Likewise," I said, smiling.

"Let's get moving, now that all the introductions are out of the way," Kelly chimed in, excitedly.

I followed them to a black Toyota, and got in the back seat. I was squeezed between Kelly and Jenny, which I have to say, knowing that they both had dicks, made it a bit awkward. They were sexy as hell though, so I didn't mind all that much, regardless of what was in their pants. Tara was driving, with Michelle in the front passenger seat next to her. We drove around North Wildwood for a while, and decided to spend a couple of hours just going bar hopping.

We stopped at one, not to far from the club where I had met them all and it looked pretty crowded. The girls didn't seem to care though, and we got out of the car and made our way to the entrance. There was a five dollar cover fee to get in, and apparently, there was a tribute band for Bon Jovi playing.

When we got inside, I decided to pay Kelly back for the drink she ordered me earlier, and went straight to the bar to grab us some shots. I came back to the stage area, to find her and the other girls sitting down, already enjoying the band on stage.

"I got us some shots," I said, sitting down with them.

"Oh, Tequila," Michelle said, excitedly as she sniffed her shot glass, to see what it was.

"Oh, someone is trying to get laid tonight, aren't they?" asked Jenny.

"What? N-No, of course not, just-"

"Relax lover boy," she said, as all of the girls started laughing.

"I was only joking with you!"

"Jenny likes to tease boys like you," Kelly whispered into my ear, over the loud music.

"Well, she's got a pretty good poker face, too!"

"Oh, yeah that's one of her best traits."

We both laughed, raised our shot glasses and clanked them together, before downing the substance. It burned, but it burned good, since I already had a bit of a buzz in me from earlier. Tara wasn't drinking to much, since she was the driver of the night, but she did have a beer after her shot. We stuck around at this place for about an hour, enjoying the band, before we decided to move on to the next bar.

Back in the car, I noticed that Kelly was starting to seem more drunk. She'd had two more shots of tequila before we left, and a couple of beers on top of it, too. I was feeling pretty good, myself.

We stopped at another bar, somewhere in the Wildwood Crest. It was more of a club really, and seemed to be packed, close to full capacity. Luckily, there was no cover charge at this one. I didn't think I would be willing to go in, if I had to pay a third cover charge in one night. I went directly to the bathroom, having to relieve my bladder.

When I came back out, Kelly was waiting for me by the door and grabbed me by the hand, spinning me around, laughing hysterically as she did.

"You having a good time, loverboy?"

"So far, so good!" I yelled, over the DJ as he called out the name of the next song. It was the song "Shots" by LMFAO. Kelly's eyes seemed to light up, as the DJ announced the song, and she started pulling me towards the bar.

"I love this song!" She shouted.

Two more shots of Tequila, and we made our way out to the dance floor and started grinding and dancing. I was drunk. It was obvious at this point, but I was feeling absolutely great.

Kelly turned her back to me, and started rubbing her ass against my groin. My hands went to her hips, holding her as she pushed back against me and eventually, we were joined by Jenny. She came up behind me, and as Kelly continued to rub her ass against my groin, Jenny started rubbing her crotch against my own ass. I could feel something hard pressing at me, through the fabric of her pants; surely, it was a cock.

Apparently, I had been right; Kelly wasn't the only transsexual in this group of friends. I would have normally, thought it strange having a cock grinding against my ass. I was so drunk though, and having such a good time, it really didn't matter to me.

The song ended, Jenny gave me a slap on the ass and whispered in my ear, "You're so fucking hot," and then walked away.

I was hard as hell, by now, but didn't really want anyone to take notice. So, when Kelly turned around and wrapped her arms around me and hugged me tightly, I prayed that she wouldn't take note of the bulge in my shorts.

Luckily, it didn't appear that she had noticed it at all.

"I'm gonna go get a couple more shots, and we'll move on," she said, with a grin.

"Sounds good to me," I said.

She took my hand, and led me back to the bar, where we ordered two more shots. She followed hers, with a glass of water; it was probably a good idea, at this point. At least she was smart. Most party girls like her, weren't smart enough to stay hydrated while drinking this much alcohol.

As we were about to turn around, and head back to her friends, Kelly mistakenly bumped into a tall, and rather buff looking bald headed guy. We thought nothing of it at first, and she smiled drunkenly, and said "Sorry about that," before we started walking away.

"Yo bitch!" I heard someone yelling over the music.

Not realizing it was directed at us, we kept walking, until someone grabbed Kelly by the arm rather roughly and turned her around. It was the guy she had just bumped into moments ago.

"Watch where the fuck you're going," he shouted, angrily.

"Get the fuck off of me," she yelled back. "I said, I was sorry!"

"I spilled my damn drink," he continued yelling, and now I was starting to get a little uneasy.

The guy seemed pissed, and drunk, and it looked like he might have no problem getting violent.

"Hey, c'mon man, back off; she said she was sorry," I said, cutting in now.

I didn't want anything to get out of hand.

"Who the fuck are you; her boyfriend?"

"I'm her friend, and I'd appreciate it if you would let go of her fucking hand," I said, taking note that he was still clutching her arm tightly.