Jay's Sex Club Adventures Ch. 05

"Hello?"

"Hey you," she said excited, "I heard you had some fun with Jen last night?"

"Yeah... well, almost... we didn't have sex. We danced for a while, and talked and then she had to head home for an emergency. I got her number though."

"That's good, you should call her. She's a lot of fun, if you catch my drift."

"Yeah, I do," I laughed, "Holly already told me."

"That's something she would know," Lisa joked, "Anyway, I was wondering if you wanted to come over and hang out with me here tonight and have a few beers, Rob and Annie will be here."

I knew Rob was going to want to talk to me about everything that had happened in the last few weeks. Last we talked was right before I told Lisa I was ready to submit to her at the party she had at her place. Since then, I'd even been with Holly.

There was almost a guarantee that he was going to want the details, to know whether or not I had enjoyed being dominated... and of course, I had!

"Sure, I'll be there."

"Great, be here around 7:30... sound good?"

"You got it," I said.

We hung up as I got in my car to drive home and take another quick shower. She texted me while I was washing up and told me not to eat before I came over, they were ordering out for food. I got my stuff together, before heading out the door again and making my way over to Lisa's apartment.

When I got there, I found Rob and Annie had already beat me there, and were seated at the kitchen table, sipping back a couple of beers. Rob stood up when I entered the apartment, walking over to give me a bear hug and a pat on the back.

"There he is," he yelled, laughing as he patted my back. "How's it going buddy?"

"Pretty good, I guess. Annie, how are you," I said smiling at her.

"I'm better now that you're here," she winked at me. I blushed, recalling the night of the party when me, her and Rob all hooked up together.

I sat down next to Lisa after she handed me a beer from the fridge, and we started talking about dinner. We wound up ordering a pizza, and sitting around just bullshitting while we waited for it to get there.

When Lisa and Annie went to Lisa's room so she could show Annie a new dress she had recently bought, Rob scooted closer to me and popped the question I knew he was probably going to ask at some point.

"So... how has it been," he asked, emphasis on the "has" part of his question. I knew what he meant, and I laughed shaking my head.

"It's been... good. I guess I'm one of those guys who enjoys it."

"Yeah? That's awesome dude," he said smiling, "I told you it's not so bad."

"Hey, don't get me wrong, I'm not going to be the bitch all the time, but I'm willing to bend over for the right girl if she wants me to."

We both started laughing, as Lisa and Annie came back into the kitchen.

"What's so funny boys," Lisa asked, with a grin.

"Oh nothing," Rob said trying not to laugh. "Jay was just telling me how he likes his hole stuffed," he said, losing his control and cracking up.

"Fuck you dude," I yelled, laughing with him.

Annie sat down across from us, and leaned over the table, giving Rob a playful shove on the arm.

"That's okay Jay," she said. "Rob enjoys his hole stuffed from time to time too."

"Oooh," Lisa teased, giggling. She glanced over at me and smiled, and I smiled back at her. The food arrived, and we ate, continuing to joke around and drink beer for a few more hours.

Around 10:00 that night, I was starting to feel pretty drunk and Lisa suggested that I stay at her place for the night, not really wanting me to drive in my condition. She had given the same offer to Rob and Annie, since they were both intoxicated as well. I decided to accept.

Not that I had much of a choice, I knew there was no way in hell she would let me drive home drunk. We both settled down on the couch, and she turned on the TV while Rob stepped out onto the balcony and lit up a cigarette. Annie sat down on the recliner across from Lisa and me.

I couldn't help but notice she seemed to keep staring at me from across the room. I just shrugged it off as Rob walked back into the apartment and sat down on the smaller couch next to the sliding glass door.

Eventually, I stood up to walk to the kitchen to get a glass of water, and noticed that Annie seemed to be checking me out as I walked past her.

I laughed silently, as I entered the kitchen. Opening the cabinet, I grabbed a cup and started to pour some water, when I heard footsteps from behind me. Turning around, I saw it was none other than Annie, standing right behind me with a big sexy grin on her face.

"Hey Jay," she said, as though it were the first time she had seen me tonight.

"Hey Annie."

She leaned against the counter, in a rather seductive manner.

"So, I was thinking about the fun that you, me and Rob had last time we were all together... did you have fun too Jay? I know I did."

"I did have fun," I answered, taking a sip of water.

"I'm glad to hear that," she replied.

She pushed herself away from the counter, stepping towards me and grabbed me by the shirt, now pulling me towards her. I was shocked as she looked deep into my eyes, that sexy look on her face fueling a fire in my groin.

"I was hoping maybe... we could have some more fun together tonight. If you're willing that is."

"I don't know, what about Rob?"

We both glanced back out to the living room to see he was still awake, but looked quite drunk and ready to pass out soon. Lisa sat across from him, hardly noticing what was happening in the kitchen.

"Let's go ask. I'm sure he won't mind though."

She tugged at my arm, pulling me out of the kitchen and standing in front of Rob, still holding me by the arm. Rob and Lisa both looked up at us, and Annie cleared her throat.

"Rob," she slurred. "I was thinking...I could maybe have some fun with Jay again, like last time. If you want to join in again, we could all have fun. Maybe even Lisa could be a part of it too this time."

"I don't know babe," Rob said.

He really was drunk, you could hear it in his voice. Possibly a little worse off than Annie, and definitely much more gone then Lisa and I were.

"I'm not really in the mood," he said, lying down across the couch. "You guys you go ahead though."

"Are you sure baby? I don't want to do it if you're not okay with it."

Annie pulled away from me now, and knelt down at his side. I could see that she really did want to know if he was going to be all right with this. She gave him a kiss on the lips, then stood and turned back towards me grabbing me by the arm again.

"It's cool," she said winking. "Let's go have some fun... Lisa, you coming?"

Looking amused, Lisa pushed herself off of the couch, and followed us down the hallway towards the guest bedroom. When we entered the bedroom, Annie shoved me onto the bed and jumped on top of me, crushing her lips against mine.

Her tongue slithered into my mouth, and I wrapped my arms around her. It felt strange that my best friend was cool with me hooking up with his significant other. But I knew it was okay, so I went along. Lisa sat down in a chair in the corner of the room and simply watched as Annie and I got more and more aggressive with each other.

She pulled off her shirt and removed her bra as her magnificent breasts popped free. Annie leaned forward so they were right in my face. I took my time, licking and sucking her nipples while she let out a satisfied moan. She pulled away and started fumbling with my belt, sliding down with my pants until my cock was right in her face.

Now she innocently smiled up at me, before wrapping her lips around my shaft. I threw my head back, moaning as she started bobbing up and down, sucking and stroking. I ran a hand through her hair and leaned back on the bed, pushing myself deeper down her throat.

She kept that up for about two minutes, when she finally came back up for air and to kiss me. I could taste myself on her breath, and it turned me on even more.

I decided to take control, pushing her off of me, onto her back and started pulling off her pants and panties, tossing them to the floor.

Immediately after they were removed, my mouth went straight for her raging hard cock, swallowing her whole. Up and down my head bobbed, my tongue flicking the head of her shaft, my hands moving up to massage her breasts.

"So eager," she whispered, moaning, "You've gotten better at this."

I gave no reply, simply continued sucking her cock for a few minutes longer. Then she pulled me away from her, and shoved me face first onto the mattress again. I felt her move behind me, and she gave my ass a hard smack that echoed through the bedroom.

"I heard you're no longer just a top, is that right?"

"It's true," Lisa chimed in, "You should try it... his ass feels so good!"

She slapped my ass again, and gave it a firm squeeze before leaning over me and kissing me on the back of my neck. I could feel her cock poking at my asshole, as she kissed down my neck and down my back.

"I think I will do just that," she said. "Lisa, do you have any lube?"

"In the drawer."

She reached over the side of the bed, opened the drawer, and pulled out a bottle of KY Jelly. She poured some of it all over her cock and started stroking it nice and slow. She stopped stroking and slid down to the foot of the bed, grabbing my ass cheeks and spreading them apart.

She buried her face between them, her tongue darting out of her mouth and licking up and down my ass crack. I shivered as she eagerly ate out my ass, lubing me up with her saliva to start, then she grabbed the lube and poured some onto my ass crack, smearing it all over.

Annie climbed over me again, resuming her earlier position, kissing and biting my neck while probing my hole with her erection.

"I'm going to fuck you so hard, you'll love it," she whispered in my ear.

Her hot breath against my neck sent chills up and down my spine and I found myself gripping the sheets, and she hadn't even pushed into me yet.

I bit my lip as I felt the edge of her cock push into my tight hole, spreading me wide. She seemed to be teasing me. Inching herself into me, little by little, trying to fuel my excitement. About halfway into me, she stopped and then in one smooth thrust, she rammed her entire length all the way in and started thrusting in and out.

The bed shook underneath of us and I moaned, every time she slammed into me she hit exactly the right spot. My own dick stiffened underneath of me, leaking a bit of pre-cum onto the sheets.

Lying flat on my stomach, I was facing the corner of the room where Lisa had taken a seat to watch. I lifted my head slightly, and noticed that Lisa was still sitting in the chair, only at some point, she had discarded her pants and undergarments, and was now stroking her own cock.

I watched her hand glide up and down the shaft of her dick, pleasuring herself to the sight of Annie relentlessly pounding my ass.

She grabbed me by the hair, pulling my head back and yelled, "Tell me you love it!"

"I do," I said, out of breath. "I fucking love it."

"Such a little slut," she said breathlessly, pushing my face back into the pillow and fucking me harder.

Eventually, she pulled out and dropped onto her back motioning for me to get on top of her. I did just that, climbing on top of her and lowering my ass down onto her stiff member. I eased my way down onto her, my ass swallowing every inch until once again she was all the way inside.

She grabbed my hips and pushed up into me until her ass was all the way up off of the bed. This allowed her to go really deep, going well past the sweet spot and I moaned louder then I had ever moaned in my life.

My eyes started watering as she began slamming up into me, bouncing me up and down on her cock, my own dick flopping around with every thrust she delivered.

"Holy fuck," I shouted, "I'm going to cum."

"Cum for me baby," she said between breaths. "Cum for me now!"

As if on command, my body went into a fit of spasms, my cock twitched and I cried out in pleasure as semen began to spew from the tip of my member.

I came so hard, and I kept calling out, nearly squealing in pleasure the whole time... I suddenly felt very much like a girl, and I certainly was being much louder than most men were during orgasm.

As my orgasm began to fade, Annie pushed me off of her and sat down on my chest, stroking her cock right in front of my face. At that same moment, the bedroom door opened and Rob stumbled in, leaning against the wall.

"Having fun in here?" he asked, sounding amused.

"You missed the fireworks," I heard Lisa say, jokingly.

"Not a bad sight," he muttered. Annie continued jerking off vigorously in front of my face, until finally she gasped and cried out as she started shooting her load all over my face.

There was so much cum, and though I didn't mind her coating my face, I really wanted it in my mouth too. I wrapped my lips around her before she finished, and she let out three or four more shots for me to taste and swallow.

When she finished, she slid off of my chest and smiled over at Lisa and Rob.

"You were right Lisa," she said, sounding exhausted. "His ass is incredible."

"I wonder if it would still have the same effect now that you're done with him though," Rob said joking with her, "How you feeling buddy?"

"Hah," I laughed, laying my head back on the pillow, "I'm fucking spent."

"I really stretched him out," Annie said.

"Let's see that asshole," Lisa chimed in.

I laughed as the room was starting to spin with the effect of the alcohol wearing off. I turned over onto my stomach, and Annie spread my cheeks for them to see my hole, which I could tell was pretty much gaping right now.

"Wow," Lisa laughed, "I think you may just be ready for Kendra now."

"Oh, Kendra would still split him in half," Rob said, "That is a nice view though."

I didn't quite expect to hear anything like that from Rob... I was pretty sure he didn't like men unless they had tits too. I turned back over onto my back and Annie stood up, walking over and giving him a kiss on the lips.

"You know," Rob said, "I wouldn't mind having some fun too buddy... but only if your okay with it. Nothing you don't want to do."

Was he really suggesting that we hook up?

"Maybe another time," he added, noticing my uncertainty. Annie took him by the hand and led him out of the bedroom, still naked, her dick swinging between her legs.

Lisa walked over and sat down on the bed next to me, leaning over at me and kissing me on the lips.

"You look beat."

"I'm pretty tired," I admitted.

"Get some rest then, okay? I'll be in soon, we can sleep in the same bed together since you're going to be staying over tonight."

"I would like that," I whispered. She stood up and walked out of the room, leaving me to myself.

I lay there in the silence for a few minutes staring up at the ceiling, before slowly drifting off into a deep coma like slumber.

I left early that Sunday morning... in fact, I think it was only about 9:00 or something. Annie and Rob were still asleep in the living room, but Lisa got up with me and walked me outside to my car.

We exchanged a hug and a kiss, and I promised I would call her before getting into the car and starting up the engine. She waved goodbye, and turned to walk back inside.

"Hey Lisa," I called from the car window before pulling off. She turned around and looked back at me, waiting for me to speak.

"Did you enjoy the show," I asked, referring to how I knew she had jacked off while watching Annie fuck the shit out of me.

"It was nice," she laughed, "But I would have rather been the one fucking you, than the one sitting there watching. I don't mind a bit of voyeurism from time to time though."

With that said, she walked back into the apartment complex, and smiling to myself, I started driving home. On the way home, I thought about how intense my orgasm had been the night before while having sex with Annie.

Lisa and Holly had both gotten me off pretty good the few times I had been on the receiving end with them, but holy shit, I don't think I'd had an orgasm that strong at all until last night.

I also wondered about what Rob had suggested, and whether or not he was being serious when he said it, probably just the booze. I shrugged it off, as I didn't think I would really be up for that anyway.

I was okay with being with a t-girl, but an actual man... that really wasn't my thing... then again, that's how I felt before I became submissive with Lisa. Now look at me... so who knows whether or not I would enjoy something like that.

One thing was for sure, my ass was pretty sore at this point, and I was going to take the week off from hooking up with anyone else. Unless they were okay with me not being the one getting fucked for a few days, then that would be a different story. I needed time to let my anus recover from the assault I had taken from Annie.

***

Almost a week later on Thursday, I was driving home from the local grocery store, having just picked up a few small items. Once I got home, I was planning on just putting away those few items and sitting down to play a game or two on my Playstation for a little while.

I'd gotten off work early, and wanted to simply enjoy the remainder of my day.

I was about halfway home, when I turned a corner to find myself behind a car that was not moving despite the fact that the light was green. The car seemed to look familiar to me for some reason, though I wasn't entirely sure where I had seen it before, or whom it belonged to for that matter.

A little irritated, I waited a few seconds, before sounding the horn to try and get who-ever this was moving. When there was no response, I sighed heavily, and leaned on the horn letting the person know I was not happy to be stuck behind them.

That's when the driver side door opened, and out stepped the last person I expected to see here: Kendra.

She walked towards my car, and I leaned back in my seat, suddenly regretting honking my horn so angrily. I hoped to god she wouldn't pull me out of the car and try to beat the hell out of me, or something like that. I rolled down the window, and she leaned in close smiling at me.

"Jay," she said sweetly, "It's nice to see you! Honestly, I was going to beat the fuck out of whoever was beeping their horn at me, until I realized it was you."

"Oh," I said, nervously, "Well uh... I guess I'm pretty happy to be me."

"You should be honey," she joked.

"What's the problem," I asked, motioning towards her car. She sighed, looking quite annoyed and shook her head.

"The fucking thing died on me," she said straightening her back, "I've been stuck here for thirty minutes now. I tried to fix it, but I think its shot."

"Have you called a tow truck?"

"I tried, but triple A said it will be a while... no worries though. I'll be okay."

I really wanted to get home, and being around Kendra made me uneasy even though she had not yet tried to make any sort of move on me, or suggestion that we hook up any time soon.

I just wanted to get home, and relax for a while.

"I'm sorry to hear that," I said trying to ease my way out of the conversation, so I could carry on, "I hope everything works out."

"Thanks Jay, it was good to see you." She backed away from the car, and I rolled up the window getting ready to pull over and go around her vehicle.

She waved at me and smiled as I drove off, and I sighed, relieved that I had gotten myself out of there so easily. Then, about halfway down the block, I suddenly started to feel... yep... guilty. I felt bad for leaving her back there, it was hot outside.

She looked tired, she had been sweating her ass off... what kind of a jerk was I to just leave her behind like that? I contemplated what might happen if I turned around and went back for her... would she want to just get a ride back to her place? Or would it turn into her trying to seduce me again. I sighed, deciding that either way it was wrong of me to just leave her on her own in the heat with a stalled car.