Jay's Sex Club Adventures Ch. 04

That Sunday morning, I woke with a dull headache and little memory of the previous nights events. I could recall hooking up with Claudia, and barely remembered my conversation with Lisa before that. I remembered passing out in the room in the basement, and the bouncer calling a cab for me.

As I got out of bed and prepared myself for the day's events, a few more memories started coming back to me. Then, I recalled the incident between Kendra and myself outside the club while I waited for the cab. She had come on quite strongly, and what really shocked me was that I remembered feeling so aroused.

"Come back and see me tomorrow," she had demanded.

I remembered the words quite clearly, and I shook my head almost laughing as I thought about what she intended to do to me if I actually went to see her today. That was the thing though, now that I was sober, I had no intention of going to see Kendra at the club.

In fact, I decided maybe it was best if I stayed away for a couple of days... maybe that would get it across to her that I wasn't really interested. Even if a small part of me actually was.

I had to do laundry today, so I set about getting my day started. It was a lazy Sunday, and I did not plan on showering. I just sprayed on some deodorant and put on the last clean t-shirt I had in the closet, then grabbed my laundry bag.

I snatched up my car keys from the entertainment center and was just heading towards the apartment door when it clicked... I had left my car parked outside The Raven last night. I took a cab home, how could I have forgotten that I left the car at the club? I'd been so damn drunk, there was no way in hell that I could have driven myself home, so what other choice did I really have?

This wouldn't have been such a big deal, except for the one thing that it guaranteed. I would be going back to the club today, and there was a high possibility that I might run into Kendra. She would think I had just come back to see her as she had told me to.

"Great," I thought out loud as I started pacing back and forth nervously. What exactly was I going to do to handle this situation?

I decided not to put too much thought into it, or I would only succeed in driving myself mad with anxiety.

"Alright Jay," I said to myself, "Relax... just cool down. You're going to go back to the club, and you're going to get your car. You don't have to go inside, and you certainly don't have to talk to Kendra."

A flashback from the night before went through my head as I remembered being pushed back into the corner. Then I remembered her hands, sliding down the back of my pants, as her fingers began invading my asshole... my cock twitched in my pants at this random memory. I sighed heavily, trying to shake those memories away.

"This is ridiculous," I now thought, "I can't believe I'm actually debating hooking up with her like this."

I knew damn well the main thing she would be interested in, was bending me over, and shoving her cock up my ass. All this time, I'd been going around talking about how I didn't want to do that yet, and now here I was, getting horny as hell just thinking about her fucking my ass.

I decided to just get it over with and go get the car. With any luck, I could grab the car and drive off without anyone there even realizing I had been there. I grabbed my wallet, left the laundry bag by the couch, made my way outside, and walked down the street to the nearest bus stop.

When I got on the bus, I sat down and leaned back in my seat. During the entire ride I couldn't stop thinking about the fact that Kendra was probably waiting for me right now... so what would I do? What would I do if she were there, if she tried to get me to come into the club and hook up with her? Honestly... I wasn't really sure.

When I finally got off the bus, I walked the few blocks down the street to the club, and there in the Raven's parking lot I spotted my car, waiting for me. I took a deep breath and started walking towards it, fishing my keys out of my pocket as I approached at a pretty fast pace. I was almost to the driver's door when I suddenly heard her call my name.

"Jay?"

I froze like a deer in the headlights, and turned my head slowly, expecting to see Kendra, then giving a long sigh of relief when I realized it was Holly.

"What are you doing here so early in the day?" she asked.

"Oh... I uh... got pretty drunk last night," I explained, "And the bouncer called a cab for me. I wound up leaving my car here overnight, and just came back to pick it up."

"Oh," she smiled, "Want to come inside and I'll buy you a drink?"

I hesitated... I wouldn't mind that at all actually, but I worried that Kendra might be inside.

"Is... Kendra here?" I hesitantly asked.

"Not yet," she said. "Why, what's wrong?"

I explained what happened the previous night, and naturally, Holly found it hysterical. She almost thought Kendra and I had actually had sex, until I explained that it had stopped before it could go past that line.

"Don't worry Jay," she laughed, "I'll protect you from the big bad Kendra."

"Holly," I sighed, a little irritated, "I'm not afraid of her, she's very attractive. It's just, she's a top and I'm a fucking virgin, I'm not going to sleep with someone, at least as big as she supposedly is, for my first time."

Holly now burst into a fit of laughter... but this time I couldn't help but laugh along with her. I followed her into the club, and was surprised to see it was pretty active for a Sunday afternoon.

I'd never been there at this time of day on a Sunday mind you, but I had somehow imagined it as pretty dead. The dance floor was empty, but the bar was very crowded. Holly ordered me a beer and we sat down and continued to talk for a while.

"I slept with someone else last night," I said, taking a swig of my beer.

"Oh, really? Jay's checking out the other girls now, huh?" she replied.

"Yeah," I chuckled, "Her name was Claudia."

"Claudia huh? She's a nice girl, and good friends with Annie too. Did you enjoy yourself?"

"Yeah, it was really nice," I said nodding my head, "she was pretty hot."

"You weren't so bad yourself," chimed a gentle voice from behind me.

Looking back over my shoulder, I found Claudia smiling down at me! I turned around on the bar stool and pulled her into a hug. After buying her a drink, the three of us were now sitting at the bar talking and having a nice time together.

Eventually Kendra did show up... spotting me at the bar, she winked at me. I smiled back at her but I guess she realized I wasn't there to hook up with her as she wanted the night before. Instead, she walked off with some other guy, both making their way into the basement together. Better him than me, I thought, at least for the time being.

"Well, I have to get going," Claudia said eventually, "It was nice to see you again Jay... you too Holly."

After Holly said goodbye, I gave Claudia another hug before she left. Now it was just Holly and I again.

"So where's Lisa?" I asked quietly.

"Oh, she's at her place I believe. That reminds me, she told me that if I saw you, to let you know she's having a big cook out next Saturday for the 4th of July, and really wants you come. You cool with that?"

"Yeah, definitely," I replied quickly.

I liked barbeques, and I liked the idea of being able to go to Lisa's apartment and hang with her and probably a bunch of other people as well.

"Rob and Annie will be there," Holly said as she lit a cigarette and took a long drag, "So will Jen and a bunch of the other girls from the club."

"No Kendra though, right?" I asked.

She laughed and reassured me that Kendra would not be at this get together. We had one more drink, and then I made my way back home. I still had to carry out my original Sunday plans, and I also was getting tired of my own bad smell, having not showered that morning.

When I returned home, I retrieved my dirty laundry bag from where I'd left it, and then took it over to the Laundromat. Getting back home around seven o'clock at night, I decided to just heat up some leftover Chinese food. After putting away laundry and cleaning up after dinner, I was finally able to give Lisa a call to let her know that I'd talked with Holly, and that she had relayed Lisa's invite for her Saturday barbeque.

"Hello?"

"Hey, it's me," I answered.

"Jay, I'm so glad you called, did you see Holly today?"

"Yeah, we ran into each other at the club," I responded, "She gave me your invite for the cook out next Saturday, I'd love to come."

"Great, I can't wait to see you," she sure sounded excited to know that I was going to be there.

She went over the list of the other people who would be there, and aside from herself, Rob, Holly, Annie, Jen and Claudia, I didn't recognize any of the names she mentioned. I assumed they were all people I hadn't met to this point in time. As we talked, our conversation drifted back to what she, Holly and I had done the day before in the park.

Then, from there, we found ourselves talking about the conversation we'd had at the club the night before.

"Lisa... you know how you said I should experiment, have fun, right?"

"Mm-hm," she acknowledged.

I wasn't sure why, but I felt the urge to tell her about Claudia... and Kendra as well. I just wanted to make sure she really was okay with me hooking up with other people from the club.

"After you left, I actually met Claudia... and we had sex."

"That's cool," she replied, sounding perfectly fine, "I'm glad you're seeing what else The Raven has to offer. No strings attached for the time being."

I relaxed, realizing she really did seem okay with it... for now anyway. I told her about Kendra, and much like Holly, she found it funny. She was glad to hear however that the amazon-like woman had backed off when I made it clear that I did not want to cross a certain line.

It was getting late, I had work in the morning, and so did she. So we said our goodbyes and hung up together. I slowly made my way back to my bedroom and just lay there in my bed, thinking about everything... mostly about how turned on I had been with Kendra, when she tried to get me to hook up with her Saturday night. It got me thinking about how I had let Lisa and Holly fool around a little with me, as far as some anal play was concerned.

I had enjoyed it all up until this point... it was fun and I found that I just couldn't lie to myself, it really felt good. But that brought up a very important question... was I ready to take it a step further? And if I was, just whom exactly, did I want my anal "first time" to be with?

***

The workweek came and went fast, and before I knew it, Friday night had arrived. I came home from work, showered, and stretched out on the living room couch to watch some TV for a while. Tomorrow was the day of the cook out, but tonight all I had to do was relax for a little while. I fell asleep early, around 9:30, without actually intending to do so, and when I woke the next day it was already noon.

Suddenly I realized I had to be at Lisa's apartment in just two hours and now remembering the shopping I needed to do, I found myself scrambling.

After quickly getting myself up, showering, and dressing, I hit the road and began picking up some of the things I promised to bring with me, such as Charcoal, Soda, Chips and a few other supplies.

While driving to the last store, my phone rang. I pulled off to the side of the road a little frustrated, but then smiled as I saw the phone's caller ID showed it was Rob.

"Yo," I answered in my usual Philly slang.

"Hey man, you going to be at Lisa's place tonight?"

"Yeah, I'm on my way there with some stuff for the cook out now."

"Awesome, Annie and I will be there around four. See you then."

I hung up, and continued driving... I was in a bit of a hurry to get to her apartment and have fun with my friends. When I arrived, Holly met me outside with a guy whose name was Ryan, in his early thirties with short brown hair and a well toned body.

"Hey Jay," Holly greeted me with a hug. "This is Ryan... and no, he's not my boyfriend, but we're very good friends."

I shook hands with Ryan and he seemed like a pretty cool, laid-back guy to say the least. He helped me carry all the stuff I'd bought up to Lisa's apartment.

The second I walked through the door I was met with a giant hug from Lisa and she laughed as we started fake dancing around the living room for a moment. Holding her in my arms felt weird, but not in a bad way.

There was just a strange spark that I felt as I held her like that, dancing with no music, both of us laughing. It felt so natural... I shook it off, remembering we both agreed on a no strings attached relationship for now.

"I'm so glad you made it," she said.

"Well of course," I laughed, "Why the hell wouldn't I?"

"Look, anyway, I want you to meet my friend Nikki," Lisa said dragging me across the living room by my arm. She pulled me over to a tall, attractive young brunette with deep, ice blue eyes, and an incredible body.

"Nikki, this is my friend Jay I was telling you about, and Jay, this is Nikki."

"It's nice to meet you," Nikki said stretching out her hand to greet me.

I accepted the gesture, shaking hands with her and we struck up a conversation while Lisa started preparing the grill out on the balcony with Ryan's help. I quickly got the impression that Lisa was trying hard to set me up with Nikki for a little fun, especially since Nikki was immediately very flirtatious. Lisa kept glancing over at us, and then noticing how close we were sitting together, started smiling at me.

What the hell I figured... yeah, I was developing feelings for Lisa. But if this was what she wanted, then I'd run with it... maybe try to have a little fun for the time being. Sooner or later, I was sure the time would be right for the two of us to stop playing games and make this official.

Why not enjoy myself as she seemed to want me to in the mean time. So I started flirting back with Nikki and things flowed quite naturally from there. Around four, Rob and Annie showed up and the party really got started. There was drinking of course, and lots of really good food as well.

Ryan was on cooking duty, making burgers, hot dogs, chicken, and a few other goodies on the grill.

It was now around seven thirty, and I was sitting on the couch with Nikki, Lisa, Holly, Ryan, Rob, Annie and Holly. We were all drinking, laughing, partying and having a really great time as we were all able to relax now that the grill was down for the day. Rob and Annie were starting to get very touchy feely with each other, and they were both obviously drunk too.

I laughed as Annie sat on his lap, making out with him. She backed off eventually and stood up, taking him by the hand and leading him down the hall to an empty bedroom. He glanced back over his shoulder and smiled, laughing as she pulled him into the room.

"Well, I guess we all know what those two are about to do," Ryan joked.

Everyone started laughing. I took a swig of beer and suddenly realized that Nikki had moved closer to Ryan, and was now flirting with him. After a few minutes, it became obvious that I had been overlooked for this guy! Oh well, I thought... it was no huge deal really, although looking over at Lisa I could see she was a little ticked off at Nikki for standing me up like that.

"I'm going to take a piss," I said, standing up and walking down the hall.

I had never been inside Lisa's apartment before tonight, so I did not really know which door led to the bathroom. I opened the first door and found that it was definitely NOT the bathroom. Instead of a toilet, I found Rob and Annie in bed together.

"Whoa," Rob said, as he and Annie both laughed. They were naked in bed, Rob on top of Annie with her legs wrapped around his waist and his cock buried in her ass.

"Wrong door Jay," Rob joked.

"Uh, yeah... sorry about that," I said, as I stepped out.

Checking the next door, I could see that it was the right one, thankfully, leading me to a much needed toilet. I relieved my bladder, all the while trying to forget that I had just walked in on my best friend and his girl. I decided that it really was no big deal, and I laughed about it for a few minutes before flushing the toilet and coming out of the bathroom.

Rob's door opened as I came out though, and he poked his head through the door and laughed.

"Hey buddy uh... come here a second," Rob motioned for me to come closer with his index finger.

Confused, I stepped towards him and leaned in close.

"Listen uh... this was Annie's idea, and if you don't want to that's fine." He whispered.

"What... what are you talking about Rob?"

"Well, Annie wanted me to invite you to uh... join us." Rob explained.

Now that was a shock! A threesome with my best friend and his transsexual partner? I never saw an invite like that coming. Did I want to do it though? I mean, how would it work? I hoped Rob didn't think he was going to be bending me over or anything like that. I wasn't sure if he was even into that stuff, as far as I knew he only dug transsexuals.

"As long as I'm not on the receiving end," I said seriously.

"Hah!" he laughed, covering his face with a hand.

"No, no of course not bro... I don't do that shit. Just you and I tag teaming Annie, that's all."

That didn't sound like such a bad thing... why not, I thought.

"Alright... I'm game."

Rob opened the door completely, and I followed him inside and saw Annie stretched out on the bed... beautiful, and still totally naked. She was spread eagle with her cock lying back against her stomach. It was pretty big, and I remembered the picture Rob showed me when he first told me about her, but it looked so much bigger in person then it did in the photo.

"Hey there Jay," she said seductively, waving at me.

"Hey," I said, smiling and waving back. "Um... thanks for the... the invite."

I felt awkward, and I couldn't I lie about that. This was my best friend's girl, and even though he was cool with it, it still felt strange.

"No problem... why don't you come over here."

"Go on dude," Rob said, giving me a push.

As I walked towards the bed, I pulled off my t-shirt and dropped it on the floor. I then slipped out of my pants and kicked off my shoes, before climbing into the bed and crawling up over top of Annie. She wrapped her arms around me, running her nails up and down my back, then pulling me close to kiss me on the lips.

Her tongue slipped into my mouth, and I groaned, my cock growing hard in between us. Annie really was quite a catch, she was fucking gorgeous, nice size cock, and beautiful breasts.

"You're a good kisser," she said, backing away,

"Come here Rob."

My friend walked towards the bed, and I moved over some to the right of the bed as he climbed onto the left side. We were both on our knees on either side of Annie, and she took hold of my cock and Rob's and started jerking us both off at the same time.

She slid up into a sitting position and wrapped her beautiful lips around Rob's big cock and started sucking him. She was deep throating him, stroking him, playing with his balls, and the sight of it was really getting me turned on.

She spent almost a full minute focusing on his dick, before pulling off and turning towards me. Now she wrapped her lips around my cock, repeating what she had just done to Rob, and I was moaning again, leaning my head back in surprise at how well she was doing.

She was a damn good cocksucker, and suddenly I felt quite envious of my friend for having such a great girl all to himself usually.

While she sucked and stroked me, Rob moved over top of her and leaned down to take her cock in his mouth. I hadn't thought Rob was into that sort of activity. I always figured that he was one hundred percent dominant, but apparently not completely. I moaned as Annie started playing with my balls, and smiled up at me.