Jay's Sex Club Adventures Ch. 02

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Jay has some fun with Holly, than hangs out with Lisa again.
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Part 2 of the 25 part series

Updated 06/08/2023
Created 12/08/2013
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The next day, I woke feeling refreshed, like it was the start of a new life...I cannot explain it but it felt like a great weight had been lifted' from my chest. Some would consider that to be the typical feeling you get after being laid for the first time in months. Ordinarily, I would agree, but in this instance I felt as though it were something completely different from that.

I got out of bed, and walked to the bathroom with a smile to relieve my bladder. I glanced at myself in the mirror and noticed I had glitter on my bare chest and a hickey on my neck. I could not help but laugh, before turning on the hot water in the shower and climbing in to stand under the stream.

As I stood there soaking under the water, my mind drifted back to memories of what I had done the night before, at The Raven, with Lisa. I recalled how incredible she was at sucking dick, and how unbelievably tight her ass was... it had felt great when I fucked her. As these thoughts filled my head, I felt my cock starting to get hard and I reached down to grab hold of it, stroking it nice and slowly.

I imagined it was Lisa stroking it for me, instead of my own bare hand, and within minutes I was shooting a load all over the shower floor. I sighed, leaning back against the shower wall and laughed.

I was definitely looking forward to going back to the club again... maybe tonight. Rob had suggested it last night when he dropped me off here in his car, and I told him at that point I would think about it. But as of right now I was pretty sure I wanted to go back tonight instead of waiting a whole week.

I wanted another go with Lisa, and maybe a chance to get to know some of the other girls at the club a little better too. Except Kendra, who I was pretty sure I wanted to stay far away from and her intentions of seducing me. Once I was dressed, I picked up the phone and called Rob to see if he was still down for going back to The Raven again tonight.

It rang once, then twice, and then a third time and finally Rob picked up. He sounded like he had just woken up himself within the past half hour probably.

"Hello," he muttered.

"Rob... dude... let's go back tonight, man."

"Hah, Hah," he chuckled on the other side of the phone. "Dude, I'm definitely down... what time is it though?"

I glanced over at the clock on my wall, it was just past eleven thirty in the morning.

"It's going on lunch time soon," I answered.

"Cool," he yawned, "How about this, give me an hour and I'll swing by with Annie and the three of us can go grab something to eat too. Sound cool?"

"Yeah, definitely," I replied.

We hung up the phone and I decided to pass the hour by going online on my laptop. I intended on just checking my e-mail and Face book account, but as the thoughts of Lisa continued to flood my mind, I found myself looking up shemale porn. I stayed away from the ones that had anything to do with guys getting fucked, focusing on the beautiful, drop dead gorgeous girls who loved to suck cock and get pounded.

I started thinking, as much as I liked Lisa, I really wanted to spend some time with some of the other people at The Raven as well. I just hoped she was not going to take that personally or anything like that. I glanced again at the clock...

Rob would be here in about half an hour. I reached for my cell phone and opened up the phone book, pulling up Lisa's phone number. She had added it to my list herself last night before I left to go home.

I pressed the dial icon and put the phone to my ear, waiting as it started to ring. Five or six rings in, I heard a soft click followed by her beautiful voice.

"Hello?"

"Lisa?"

"Jay? I'm glad you called," she said, sounding excited, "I miss you already."

"Yeah, me too. I'm going to be at The Raven again tonight with Rob. Would you be there if I showed up? I'd love to see you again."

"Definitely, I'm there most weekends. Maybe we could have a bit of fun in the basement again if you're up for it... oh, and Holly and some of the other girls were looking forward to hanging out a bit as well."

There was a hint of jealousy in her voice, and I laughed. She must have realized that I had noticed her sarcastic tone of voice, because she started to laugh as well.

"Don't worry," she said, "I'm not going to hold you all to myself, besides I'm not exactly looking for a relationship right now anyway."

"Is that so?"

"Yeah, I don't know... it's just not for me, you know? Not at the moment, at least... maybe someday, I will be a little more open to 'falling in love' but right now, I just want to have some fun. With that said, if you're looking to have fun with some of the other girls too, I'm not going to act like the jealous girlfriend."

There was no hostility in her voice or resentment either, in fact, she actually sounded serious. That was a good thing... I had been nervous about bringing up this topic, but she had brought it up on her own. Not only that, it looked like it had also gone in the direction I was hoping it would go as well.

"That's cool Lisa... but tonight, I think I want to be with you again. There will be time for me to get to know Holly and the others. Maybe we could even have a threesome sometime together?"

I bit my tongue right after saying that, I felt like I had blurted it out without even stopping to think before opening my mouth. I hoped that I had not just ruined things for myself all together... I waited for an answer.

"I like that idea," she said, as I let out a heavy sigh of relief.

"It wouldn't be the first time Holly and I have had our way with a cute boy like you together,"

she giggled, "It's always fun when we do too."

"Awesome," I said happily, just then, I heard a car horn outside beeping and I cleared my throat,

"Well, I should go, Rob is here with Annie and we're going out to lunch and hanging out for a few hours. So I'll see you tonight?"

"Definitely,"

She sounded just as excited about our second encounter as I was, and we hung up the phone on a good note. I quickly put on my shoes and made my way downstairs and outside, getting in the back seat of Rob's car. He and Annie both greeted me and we headed off to a nearby burger shop for lunch. As we sat and ate, I told Rob and Annie that I had called Lisa before they picked me up.

I told them things seemed to be going great and I was excited to go back there tonight.

"So she's cool with you hanging with the other girls," Rob asked.

"Yeah, she even agreed to her and Holly possibly having a threesome sometime."

Annie laughed, "Yeah, those two love threesomes. You're going to get lucky all the time as long as the both of them are your friends Jay."

I knew she was right, and just the thought made my cock twitch in my pants. I could not wait to get back there tonight.

We left the restaurant together and drove back to my place to hang out, and watch TV for a couple of hours before heading out that night. It was probably around 7:00, like the previous night, when we made our way out the door and to Rob's car. We arrived at The Raven by about 7:30 and I made my way inside behind Rob and Annie who went straight for the bar.

I followed, not knowing for sure if Lisa was here yet, and took a seat with my two friends. I ordered a Jack and Coke. Since Rob was driving me home tonight, I could have a couple drinks if I really wanted to. I felt a hand on my shoulder, and turned expecting to find Lisa, but it was actually Holly and Jen.

"Hey," they both greeted me together, looking happy to see me.

"Hey, how's it going," I answered just as excited to see the both of them.

"Back again huh," asked Holly.

"Yeah, I couldn't stay away," I replied, "I had way too much fun last night."

"I bet you did," Jen winked and we all started laughing. Both girls sat down, joining us at the bar, and I treated them each to a drink on my tab.

We talked for a while and before I knew it, it was getting close to 9:00 at night... I wondered if Lisa was going to show up tonight or not. She said she would be here, but maybe something else had happened and she could not make it.

No sooner had the thought crossed my mind, than my cell phone started to ring in my pocket. I pulled it out and looked at the caller ID and sure enough, it was Lisa. Nervously, I picked up and placed it to my ear.

"Hello?"

"Jay... hey, it's me."

"Hey, where are you?"

"I can't make it tonight," she said, as I noted how she actually did sound rather disappointed herself at this sudden turn of events, "My car broke down, and I wound up having to stay late at work too, and I'm really tired. I could catch a cab but I am absolutely exhausted."

"That's okay," I said, really wishing it had not turned out this way.

"Stay home and get some sleep, I'll be here again next weekend and we can get together and have some fun again then, sound good?"

"Absolutely, and Jay... listen... if you want, you could spend some time with Holly or one of the other girls instead tonight. Like I said, she's wanted a chance to have some fun with you as well anyway."

I looked over at Holly, and she winked at me and I laughed slightly. I thanked Lisa for calling me and told her that I hoped everything worked out with the car before next weekend, and if she needed anything to call me. We hung up, I set the phone down on the bar counter, and Holly glanced over at me.

"That was Lisa? She on her way yet or no?" She asked.

"She can't make it... her car broke down and she's really tired."

"Awe, what a shame," she said trying to sound disappointed, and I laughed at how easy it was to see through her little act. She giggled and scooted closer to me and began flirting a bit more heavily than before.

"No, but really... I love Lisa. She's my best friend, and she wouldn't mind."

"No, she wouldn't actually," I agreed, "She told me to go ahead and hang out with you tonight instead."

Holly's eyes lit up and she started to laugh.

"I told you she was my best friend," she said and I smiled. We continued talking for a while longer, the night wearing on and I could see the whole time that Holly kept checking me out.

Eventually, Jen got up and walked off to the dance floor, leaving Holly and I alone. Holly then looked over at me and winked. I knew what she wanted, and I wanted it just as much, I was feeling the alcohol, and when I get drunk or even a little close to drunk I usually get horny.

So when Holly stood up and took me by the hand, I offered no resistance, sliding off the bar stool and following her towards the winding staircase. Down into the basement we went and took one of the first rooms on the left hand corner of the long hallway. This room was different from the one Lisa and I had shared the night before; it was a little smaller and instead of a couch, chair and mattress, there was only a mattress.

Holly shut the door and locked it. I sat down on the edge of the bed and she walked over to me smiling as she then did a nice little sexy dance for me. She was showing off all the sexiest parts of her body as she danced. She was wearing just the right clothes to show me the right amount of cleavage. Her legs looked smooth and beautiful, and she brushed a strand of her hot pink hair out of her face before sitting down on my lap.

I held her close, and she pressed her lips to mine, sliding her tongue into my mouth. I kissed back as we embraced one another in a heated make out session. That lasted about a minute and a half, before she slid off my lap and on to her knees. She undid my pants, and I leaned back on the mattress as she pulled them down around my ankles, my throbbing erection sprang free. Holly wasted no time, wrapping her lips around my member and swallowing me whole.

She bobbed her head, sucking, slurping and stroking and I groaned... she was just as good at this as Lisa had been. She cradled my balls, massaging them with one hand as she sucked me hard, and rubbing my inner thigh with her other hand. She used that same hand to slide up my stomach to my chest, lightly pinching and squeezing my nipples.

"Oh fuck," I moaned, "You're so good at this, suck my cock!"

I was running a hand through her pink hair and she responded by picking up her pace, bobbing her head faster, and then deep throating me. I could feel myself getting closer and closer to the edge of an orgasm, and when it finally overcame me I swore so loud that I was certain whoever was in one of the rooms next to us would be able to hear. Not that it mattered, anyone next-door would be doing the same.

I fired off several ropes of hot sticky cum down her throat, she swallowed all of them with excitement and vigorously licked the head of my shaft and the shaft itself clean. Then she moved up, getting off her knees and kissing me on the lips again. I could taste myself on her breath, and I moaned into her passionate kiss as she took my hand and led it to her crotch.

I rubbed her through her denim skirt and she sighed, breaking the kiss and leaning her head back as I massaged her.

"Jay," she whispered, "I want you to take my skirt off."

I quickly obliged, moving both hands to the hem of her skirt and hooking my thumbs under the edges. I slowly pulled it down over her smooth legs. She lifted one foot and then the other slipping out of it all together. I threw it to the floor and watched as she stepped back and hooked her thumbs under her pink panties. She slipped out of them as well, threw them aside and turned to face me again.

Now I could see her cock, and she was actually pretty big. She must have been about seven or eight inches, and she was already fully erect and ready to go with a tiny bead of pre-cum leaking from the head of her shaft.

"So... Jay,"

"Yeah,"

"Have you ever sucked a cock before?"

Oh boy, I thought, here we go. I should have seen that question coming along without any trouble, but it still had come out of nowhere. Holly definitely seemed a bit more determined to get what she wanted then Lisa was, and I was positive if I made it clear I did not want to do this, she would back off.

However, I was also sure she would do everything she could to convince me before I got to the point where I did make it clear I was not interested. As she took her huge cock in her hand and started stroking it though, something came over me and I found myself wondering... did I want to say no?

"Uh... n-no,"

"No? Well, I think it's something everybody should try at least once."

As she said that, she inched closer to me, and I just sat there completely frozen in place. Her dick was huge this close up and rather fat too. She stopped right in front of me, her member just an inch away from my mouth. She started to stroke my cheek, holding my gaze, and then ran her hand through my hair before probing my lips with her cock.

As she poked my lips with her throbbing member, I inhaled the musky aroma of her genitals and found my own dick growing hard once again. I had come to this club with no intentions of submitting to anyone, and yet here I was, giving in to temptations, about to suck a dick.

What the hell, I figured, it was not as if I was taking it in the ass. I could perform oral sex on her or most women I might hook up with in this club, it did not mean that I absolutely had to bend over and let them fuck me just because I sucked their cock.

Giving in, I opened my mouth and she pushed her erection between my lips. She tasted a bit salty, but it was not very bad of a taste to be honest. I almost felt like I actually enjoyed it as I closed my mouth around her and she took a handful of my hair and lightly pulled at it. As she pulled my hair, she started thrusting her pelvis, pushing her cock in and out of my mouth. It was as if she was fucking my mouth. It was an odd feeling, but I was enjoying it still.

"Mm, yeah, that feels so good, you sure you've never done this before Jay? Because you are too damn good at it to have never sucked dick,"

"Mmmf," was all I could get out with her huge dick rammed down my throat. She giggled and that is when she started to pull my hair a little harder and as she did, she started pushing deeper into my gullet trying to get me to deep throat her.

I choked and gagged as she touched the back of my throat, and after a minute of forcing herself down my throat, I felt saliva running down my chin. She moaned, pushing her cock all the way in and holding that position, I could feel her big, warm balls against my chin.

"Oh fuck, I have to stop or I'm going to cum," she moaned. She pulled out of my mouth and I gasped for air, breathing heavily.

Holly smiled and laughed a little handing me a tissue to wipe away the spit.

"Your really good at that," she repeated her earlier compliment, with great satisfaction in her voice.

"It's a shame your not interested in being fucked, if your that great of a cock sucker, I can only imagine how good it would feel to shove my dick up that tight little virgin ass of yours."

"Thanks," I said my voice a little scratchy, "But I don't think so... maybe someday, but I'm not interested at the moment."

"That's okay, I'm not pushy. So what do you want to do next?"

To be honest, I had my eyes on her ass almost the whole night and as they drifted back to that part of her body, I felt my cock grow rock hard again.

"Why don't you come ride my dick," I suggested.

"Ooh, sounds fun to me baby," she replied. She reached into her purse and pulled out a bottle of Astro-Glide and a condom, handing me the condom. I lay back on the soft mattress, my throat sore. I tore open the package and prepared myself while Holly was busy lubing her asshole up nice and good. Once we were both ready to go, the bed shifted as she climbed on to it and straddled me.

I could hardly wait until I was inside of her...oh fuck, she was so tight, Just like I had imagined, as she lowered herself down onto me, my cock pushing into her hole, I practically came right then and there.

She must have known how much control she had over me, because she seemed to be slowly inching her way down my pole with a big sexy grin sprawled across her face, it was as if she was trying to torture me by slowly applying herself to me rather than diving right in as I wanted.

"You're so big,"

"And you're so tight... fuck... your ass feels so good Holly."

"Why thank you baby," And with that I got my wish, as she slammed herself all the way down onto my cock until I was buried deep inside of her. I grabbed her by the hips and she started bouncing up and down on me, my dick sliding in and out, her tits jiggling, the bed shaking underneath of us.

The room was filled with the smell of sex and the sounds of passion, as we both moaned and sighed in pleasure. Soon, she was begging me to fuck her, and I had flipped her over into missionary so we could look each other in the eyes as I started to pound her with long, hard powerful strokes.

Her own cock was resting against her belly, leaking pre-cum and every time that I slammed into her, it would shake; it was a sexy view. One that fueled my aggression, and I picked up the pace fucking her harder and harder.

She dug her nails into my back, screaming my name and I felt myself building up towards the end. She was already there, I could tell judging by her passionate moaning and how her body kept trembling like a leaf underneath of me. A few more powerful thrusts and she cried out, her cock jerking, shooting a massive load of hot, sticky cum all over her own belly and her tits.

I lifted her legs up all the way and started pushing as deep into her as I could get without harming her. Finally, about a minute later, I howled in pleasure as I exploded deep inside, trying to fill her with my own cum. When it was over, I collapsed onto her and she wrapped her arms around me and held me, as though she were actually my lover. It was a comfortable feeling, and I found that I really enjoyed it, almost more than the sex itself.