Jay's Sex Club Adventures Ch. 04

"You're such a cute guy Jay," she whispered, "I heard you showed Claudia a real good time last weekend, is that true?"

"Yes," I moaned. She wrapped her lips around me again, and I leaned my head back in pleasure. She sucked me for a few minutes longer, before backing off and slapping Rob on the ass.

He turned around and kissed her full on the lips. They broke apart, and she then looked at me.

"Care to return the favor baby," she asked, motioning down towards her cock. I moved down past Rob, to the foot of the bed and started sucking her off, while she and Rob made out with each other.

She was about eight inches big, thick too, and it took me a minute or so to get all of her into my mouth. Eventually, we had all moved around a bit to the point where Annie was on her hands and knees, ass pointing straight up into the air with Rob at her side. He glanced over at me and smirked, handing me a condom.

"Go ahead, buddy."

I quickly tore open the package and unrolled the latex over my erection, making sure it was on properly before getting up behind her.

"Fuck me Jay," she pleaded, in her sexy voice.

She looked back at me over her shoulder, with eyes that peered right into my soul, and I lost all control. I grabbed her by the hips, scooted forward and pushed my cock into her asshole.

She sighed as I pushed into her and started pounding away. As I fucked her ass, Rob took hold of her dick and started jerking her off. This went on for about a minute and a half before he got around in front of her and made her start sucking him off. She was in the middle of us both, my erection sliding in and out of her asshole, and Rob's back and forth between her silky smooth lips.

I felt the pressure building up in my balls, and knew I was getting close. I bit my lip trying not to cum too soon, but it just was no use. A few more powerful thrusts, into Annie's beautiful bum, and I just howled, erupting deep inside and pumping rope after rope of semen into the condom.

She moaned against Rob as I came so hard, and when it was over, I slid out and collapsed on the bed. Rob moved around behind her and took my place, guiding his cock into her ass and started fucking the hell out of her all over again.

I sat up, sweating like crazy, and grabbed my clothes, sliding back into them while my two friends continued going at it next to me.

I slipped out of the room, leaving them behind. It had been fun, but the alcohol was wearing off and suddenly I was not feeling too good. I went for the bathroom, and splashed some cold water on my face, drying it with a towel and washing my hands in the sink. I finished up and went back out to the living room to get a new bottle of beer.

About half an hour later, Rob came out of the room and we both sat out on the balcony as he lit up a cigarette and started drinking another beer as well.

"Mm, I'll tell you... Annie really knows how to do it, right Jay?"

"Yeah," I laughed, "You've got a good girl there Rob, don't fuck it up."

"Nah, man, I'm not screwing this up any time soon," he said taking a swig of his beer and sighing.

"Man... nothing like an ice cold one after some good sex though, right?" He stood up and leaned against the railing behind him, groaning and looking up for a minute.

"You okay, Rob?"

"Huh? Yeah... sorry, my uh... my ass is killing me."

"W-What?" I stammered. He started laughing and shaking his head.

"You didn't know? C'mon Jay, Annie and I... we're not into vanilla sex or anything. I know I told you earlier I wasn't into that shit, but I guess I sort of lied. I'm a pretty versatile guy, buddy."

I never would have guessed that Rob, at least the macho guy I had envisioned him as, would be someone so willing to let anyone stick ANYTHING up his ass, let alone a girl who happened to have a penis. I laughed it off though and he realized that it wasn't quite as awkward as I had made it seem like it was at first, which helped him relax a bit.

I started thinking about it though. This whole time, I had been fooling around with anal play. It felt good, really, a finger or two wasn't so bad. With Kendra coming onto me so strongly though, and the knowledge that Lisa and Holly both wanted a piece of me in that way too... well lately, I just wasn't so sure what to think anymore. A part of me felt like just playing around was starting to get kind of boring.

"Hey uh... Rob... what's it like?" I asked.

"What," he shot back confused, "What's what like?"

I tried to find the right way to say what I was getting at, without making the situation awkward or sounding gay... although it was difficult not to sound gay no matter what you did when talking about this sort of thing.

"Y-You know... to be on the receiving end."

"Oh," he laughed, "I don't know... feels pretty good to me. Then everybody has their different opinions... you know? Some guys, they hate it... it's not guaranteed to be the sort of thing where you finish and think wow that was incredible! You might think that way, but you might not like it so much either. I guess it could go either way. Why do you ask?"

"I don't know," I said nervously.

"Oh don't tell me Jay... you thinking about submitting to one of those beautiful girls in there? Dude, you don't know what you're missing."

"Wait... I thought you just said it could go either way," reminding him of how foolish it sounded to assure me it would be incredible when he just got done telling me it might not be.

"Yeah well... I mean... have you ever had anything up there before?"

The motions he was making with his fingers, to indicate sticking something into a hole, made things a hell of a lot more awkward and I sighed taking a swig of my beer.

"Yeah," I replied finally, "I've messed around a little here and there with Lisa and Holly... just some playful activity, you know. Never went past that specific line though."

"Hm... well, how often you guys do that stuff?"

"Often enough I guess," I said, not really all that sure myself.

"Well... it might not be so bad your first time. My advice to you though is this, make sure your first time at least, is with someone you trust. Trust makes things all the more easy in the long run. I'm telling you, if I had given it up to some random girl at the club I don't think I would have been able to control my nerves. Annie really kept me calm the entire time and it made things a whole lot better."

I smiled, it was really so sweet, the relationship those two had. I had seen it myself first hand in the bedroom an hour ago, and I knew it was something special. Something that could never be broken easily.

"Anyone you trust enough for that first time buddy?"

I thought about it, and smiled again, of course I knew the answer to that question. Maybe we weren't romantically involved like Rob and Annie were, but I felt at peace whenever I was with her. I guessed it was about the closest thing I could get at this point to what Rob and Annie had, or maybe it was technically a relationship, just not a close one.

We were together, but more like friends with benefits then boyfriend and girlfriend. Regardless, I knew exactly who I trusted enough to take that step with the first time.

"Yeah... excuse me," I said smiling back at him, "

I have to go talk to Lisa!"

As I stepped into the apartment, I heard Rob yell, "Go get her buddy!" from behind me.

I looked around trying to spot Lisa and saw her out in the kitchen talking with Jen, who must have just arrived here a few minutes ago. I walked in as Jen smiled and waved at me giving me a hug. Then I looked over at Lisa.

"What's up," she asked, "You okay?"

"Yeah... could we talk? Like out on the balcony maybe?"

"Sure," she said, sounding a bit nervous. I took her by the hand and led her to the balcony, thankful that Rob had come back inside already.

We stepped outside and she closed the sliding glass door and I leaned against the railing where Rob had been a few minutes earlier.

"Jay... are you upset over Nikki? I'm really sorry, I didn't expect her to go do something like that. She knew I wanted her to hang..."

"Lisa," I interrupted, "it's not that, really. It has nothing to do with Nikki actually."

"Oh... well then, what's the matter?"

"Nothing's wrong, I just wanted to ask you something. Lisa... I've been thinking a lot lately and um... I just kind of think... well, you know how you've been playing around a bit, trying to... sort of ease me into the whole submissive role?"

"Yeah," she said, unsure of where I was going with this.

"Okay... I kind of think what we've been doing... well, it's been fun. But now it's just getting a little boring."

"Boring. Oh. Is that a good, or a bad thing Jay," she asked, with a suggestive tone. I think she was starting to see where I was going with this, or at least I hoped she was.

"Could be a good thing," I said smiling. "I kind of want to take it to the next level, if you know what I mean. I think I'm ready now."

She smiled, looking pleased with that decision but she sighed, turning around and sitting down in front of me. She looked confused which I was not quite sure why she would look like that. This was what she had been waiting for me to do after all, so what could the issue possibly be?

"What's wrong?" I finally asked.

"Nothing," she said. "Just... well, why me?"

"Huh?"

"Why would you want me to be your first, Jay?"

"What do you mean... why not?"

"I mean... hasn't Kendra been trying to get at you this whole time too? I know what happened between you guys last week at the club. I heard about how she got up close and personal with you... and a few people told me it looked like you had enjoyed her little teaser."

Obviously, someone had seen Kendra backing me up into that corner and then fingering me while I had been drunk. I wasn't sure who had seen me, but whoever it was had gone and told Lisa. She hadn't seemed upset this entire time, but now I could see she was a little turned off about it for some reason.

"Lisa, first off," I explained, "I was drunk that night. Secondly, I don't think Kendra would be good for my first time, especially if she's as big as most people claim she is."

At least that got her to laugh, and I smiled, sitting down next to her.

"Are you mad at me?" I said looking closely into her eyes.

"No, of course not," she replied, "Honestly... I don't think I'd mind if you did have sex with Kendra. It's not as if I have any sort of personal issue with her. I just kind of... well, I wanted to be your first."

"Well, I'd sure like to give you that opportunity," I said hoping that what happened with Kendra would not prove to be a bad thing.

"Okay then," she said, making me as happy as I could ever remember to receive that sort of a reply, but at the same time I was also extremely nervous, "Stick around tonight, after everybody else leaves, and we'll see where it goes."

So that was it... I was going to take on the submissive role for the first time. I could see the excitement in Lisa's eyes, and it mirrored my own excitement, but definitely not the sense of anxiety that I felt. Lisa had plenty of experience on the receiving end, and equal experience on the dominant side as well. But it was exactly that reason why she probably would not understand the nervousness that I was experiencing.

Around eight o'clock that night, Ryan and Nikki both left, along with Jen. Rob and Annie were still there, relaxing on the couch but after a few minutes started saying their goodbyes. Holly was passed out on the other sofa, and as Rob and Annie were leaving, they woke her up and offered to drive her home, which she accepted.

Lisa told me to go slip into the bathroom and use the shower, she didn't want Holly to realize what was about to happen, so she told me to be quiet about it.

I understood that Lisa wanted me all to her herself the first time, and that was why she was keeping me from Holly tonight, whereas usually she'd be completely open to the idea of sharing me.

I went into the bathroom and used the shower. Luckily, Holly was drunk enough that she didn't even notice me walking into the bathroom as Rob and Annie helped her out the apartment door.

A few minutes later, I heard a knock at the bathroom door, then the door opened and Lisa poked her head inside.

"When you're done in there, come meet me in my room... I'll be waiting for you."

"Okay."

"And don't bother putting on any boxers or anything, just get dried, that's all I'll need."

She closed the door and left me to finish washing up. The entire time I stood under the hot water, I was as nervous as I had ever been in my entire life. I finished up, dried off, and came out of the bathroom with just a towel wrapped around my waist. I entered the bedroom, to find the lights were out and the only sound was that of the air conditioner running on low setting.

"Hey," I heard her say quietly, "You ready baby?"

"I think so," I answered, as I nervously approached the bed. The only light now came from the bathroom and as she pulled back the blankets, my eyes were gradually adapting to the darkness, exposing her completely naked body.

Including of course her cock and this was already standing at full attention. I laughed, noticing how hard she was and climbed slowly into the bed with her.

"All fired up already, and we haven't even started yet, huh?"

"I guess just the thought of your pretty little ass gets me going."

"I'm flattered," I replied.

I crawled over to her, kissing her on the lips. She wrapped her arms around me, with me on top, then moved her hands down to my ass. Suddenly, I felt a little awkward, like the roles had been completely reversed. Naturally, they had indeed been switched, but I had not expected it to feel so strange.

I still wanted it... badly... I just needed to adjust to being the one treated like a girl.

As we kissed she groped my ass, and moved her other hand to take hold of my cock, stroking me slowly. Then we parted and she winked at me before pushing me onto my back. Reaching in to the nightstand, she grabbed a bottle of lube and held it up for me to see.

"This is to make sure it's not too painful, you can never have too much of it." She explained.

She moved towards me again, taking hold of her dick and stroking it right in front of my face.

"But first," she said seductively, "Why don't we have a little foreplay... just to get warmed up. Sound good?"

"Sure," I replied.

She sat on my chest, and slid forward some, thrusting her huge cock into my mouth. I choked as she slid right to the back of my throat. I groaned as I felt her warm balls against my chin and I could smell her beautiful, intoxicating scent as she began face fucking me. That lasted around two minutes, before she withdrew and backed off some.

"Don't want to get too fired up now," she laughed.

Lisa placed one hand on my side, and pushed me over onto my stomach, spreading my ass cheeks. I felt her slide down to the edge of the mattress behind me, and then I felt her hot breath on my tiny asshole.

I groaned as she stuck her tongue out, and started licking all around, moving it up and down along my crack. It felt great, and I felt my dick begin to stir underneath of me. Having it pinned between the mattress and myself was becoming a bit uncomfortable.

As Lisa continued her rim job performance, my nerves started to rise again and once more my heart began to race. All kinds of questions were racing through my head... would it hurt? Would I even like it? Would it make me gay, or less of a man... I didn't know.

I knew I wanted to try it, I just felt so damn nervous. I felt her face back away from my ass, and then I heard the sound of the bottle of lube being opened. She squirted some into her hand and started rubbing it all over my ass, smearing it along my ass crack.

I was already kind of wet from the rim job but she made sure to apply a generous amount anyway, before slipping her index finger into me. I sighed, as she started rubbing the prostate, moving her one finger in and out of my tight virgin asshole for a few moments.

Then, I felt myself being stretched as she inserted a second finger. At this point I was used to all of this, so it did not really hurt. Especially with the lube she had applied.

As Lisa continued to finger fuck me, I looked back over my shoulder and could see that her dick was harder now then it had been a few minutes ago, if that were even possible. She had this lust crazy look in her eyes, as if she wanted to just pounce on me and shove it in. But I knew I could trust her. After all, it was the reason I had picked her to be my first. I knew she wouldn't do something like that... certainly not on my first time anyway.

"Sorry," she whispered, realizing I had noticed how aroused she was. "I guess, just the thought that I'm about to get what I've wanted since we first met, is enough to make me horny."

"It's okay," I laughed softly "I know you've been waiting for this. So have I, and I'm just happy to know that you're willing to go at my pace. Even if you'd rather stuff it right in," I said, laughing again.

That also earned a chuckle from her as she gave me a playful slap on the ass.

"Such a bad boy," she said in her sexiest voice

"Talking dirty like that... are you my bad boy Jay?"

I didn't reply right away, which earned a harder slap on my ass causing me to jump in surprise.

"I asked you a question, Jay... are you my bad boy?"

"Yes."

"Yes what?"

"Yes, I am your bad boy..."

"Good,"

I felt a third finger slipping into me and I buried my face in the pillow, silently screaming, not because it hurt... but because I wanted her to just fuck me now. I was surprised at my own thoughts, just a minute ago I had been so nervous she probably would have stopped if she knew how anxious I really was. Now, I just wanted her to get to the point!

"I think you're ready," she finally said.

Now she flipped me back over, onto my back again. Lisa grabbed the lube and poured more into her hand, lifting my leg and smearing it all over my ass again. She smiled down at me, before sitting up on her knees and raising my legs up to her shoulders. She leaned over me in the missionary position.

This definitely felt awkward, but I didn't care anymore. I felt her hard cock poking at my hole, and I felt my nerves begin to rise once again. My own cock was now as hard as hers was though, so I pushed all my anxiety aside. It was now or never, I told myself... if we didn't do this now, I probably would never be willing to give it a second shot.

"Are you sure you want this," she asked.

She was being just as gentle with me as I had hoped she would be, that made things a lot easier.

"Just fuck me," I replied quickly.

That seemed to put a very sexy grin on her face, and she leaned in to kiss me fully on the lips. I felt her tongue slide into my mouth and then I felt her huge member pushing at my hole. At first, she just gently poked at it, teasing me.

Then after a few seconds, she gave a gentle push and I felt the strangest sensation I had ever experienced. Like pressure, and it almost felt hot, followed by a strong feeling of fullness.

"Agh," I hissed. It stung a little, but to my surprise only a little. She must have used just enough lube to ensure the pain was low.

"You okay?"

"Yeah... I think so. Are... are you in?"

"Only the head," she replied, "take a deep breath... I'm about to push the rest of the way in, and it might feel kind of weird at first."

I followed instructions, taking a deep breath, and almost holding it, until I felt her begin to push into me. I felt every inch of her huge member sliding into my tight hole, and it felt as if it would go on forever. Finally though, I felt her warm balls pressing against my tailbone and realized she was now all the way inside.