Jay's Sex Club Adventures Ch. 14

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Jay helps Holly through her depression.
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Part 14 of the 25 part series

Updated 06/08/2023
Created 12/08/2013
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As soon as Holly agreed to my idea of movies and pizza, we set out to grab a few things from the store we would need to enjoy our night in together. We drove to a nearby store and bought some junk food and drinks before heading back to the apartment and starting our night of events.

We skimmed through our stacks of DVDs, but couldn't find anything we wanted to watch.

So, I turned on the Playstation 3, and we went on Netflix in search of something... but after another hour, we still couldn't agree on anything we felt was worth watching from there either.

I was beginning to think this whole idea was doomed to fail, I had wanted to cheer her up by doing all of this. Yet here we were, struggling to find anything to do together... I was hoping she wasn't too disappointed.

To my surprise, she was far from ready to give up on the night. Holly eventually suggested that we play a couple of Video Games together, to which I agreed. After all, it was better than nothing. We settled on a game of Grand Theft Auto for a little while, taking turns with the controller. It actually turned out to be quite a bit of fun, and I could tell she was beginning to enjoy herself.

She had that smile I had been looking for, that had been so hard to catch her with ever since Lisa took off. That was all I needed to see to make my day feel a whole lot better.

After we finished that game, we moved onto a fighting game I had buried in my collection, this way we could play each other, instead of having to switch back and forth. It turns out Holly's really good at those types of games.

Half an hour in and I was getting my ass handed to me. We had just finished the 4th round already, and she was getting a real kick out of it.

"Stop toying with me," she said, beating my character into a corner.

"What's that supposed to mean?"

"Your letting me win! Don't hold back on me now!"

I laughed, fighting my way out of the corner, while paying close attention to my health bar on the top right hand corner of the screen.

"Holding back?" I laughed, "Your kicking my ass... for real!"

A final punch followed by a pretty nasty kick, then my health bar dropped below zero and my character was dead. Holly had won for the 5th time in a row. I glanced over at her, and she gave me an evil smirk, and I couldn't help but start laughing. "What?!" I asked.

"Are you sure you didn't let me win?"

"Holly, I'm not playing... you won fair and square,"

"Ha, ha, I know that... I'm just messing with you. Okay, what do you want to do next? Maybe you'll let me kick your ass a sixth time in a row?"

As tempting as that was, considering I did love this game so much... I wasn't looking forward to getting my ass handed to me yet again. My stomach rumbled, and I set the controller down and stood up to stretch.

"How about we order?"

We agreed on a pizza place that we both enjoyed, well known for making an extra cheesy pizza, something that both of us loved. I grabbed my cell and dialed their number, placing an order for a large pie, half Pepperoni, and half plain. After getting a price from the woman on the other end of the phone, I hung up and set the phone back down.

"About forty-five minutes to an hour," I said.

Holly stood up and grabbed both of our drink glasses. Watching her walk from the couch out to the kitchen, as I'd done a dozen times before, I suddenly couldn't help noticing how her body's wonderful symmetry made her gorgeous ass sway from side to side. My eyes had became somehow transfixed, following her every move. She was wearing a simple pair of short shorts, and a plain white t-shirt. The natural blonde color of her hair had been gradually reappearing, since it had been quite some time since she last dyed it.

It seemed almost strange to see her without some sort of dye in her hair. When I first met her, almost a year ago, it had been a very hot pink.

I found myself following her into the kitchen where she began pouring two fresh glasses of Coca Cola.

"So," I said as she handed me my glass, "you feeling any better?"

Leaning back against the counter and taking a sip of her drink, that beautiful smile reappeared, and I once again felt my heart melting from its warmth.

"I'm getting there... thanks to you. I'm glad you took off tonight... and admittedly flattered that you did it just so you could be with me."

"Well, Rob forced me out of the apartment to try and cheer me up... I felt someone had to do the same for you. Plus, I really missed seeing you smile."

Holly blushed, stepping away from the counter and wrapping her arms around me, I pulled her in close for a warm hug. After separating, we decided to sit down at the kitchen table and talk while we waited for the pizza. We talked about everything from work, to the thoughts that had been bothering us over the past few weeks, ever since Lisa left.

I certainly wasn't surprised to learn that both of us felt almost the exactly the same way regarding the WAY she left. But we both seemed to understand we had to move on with life. Lisa was gone, but we still had each other, we weren't completely alone. And we still had all of our friends at The Raven too, which was definitely a plus. Finally, Holly lit up a cigarette, and eyeing me closely, leaned back in her chair as I took another sip of my drink.

"So," she said suggestively, "did you have fun at The Raven last night?"

"Yeah," I laughed, "it was fun.

I wasn't honestly expecting anything to happen there. I just went to have a few drinks with Rob."

"Was it just Claudia you had fun with," she asked in a teasing voice.

"Well... um... I had brief 'quickie' in the bathroom

with Kendra."

She started laughing, while taking another drag of her cigarette.

"You two still have something going, huh? You know Jay, I think Kendra really likes you."

"I know she does," I agreed, "She wants me to spend a weekend with her. I told her I would, but I'm not sure when it's going to be."

"Better bring extra lube... I'll say it again, you have to have good skills to handle someone as big as Kendra."

"Tell me about it," I sighed.

Kendra's reputation had made her out to be bigger than she really was. I remembered how nervous I'd been before I actually slept with her. It definitely hurt the first time, though I enjoyed it anyway. I was becoming more experienced with 'getting it in the ass', and my confidence level had improved a great deal since that first time. So while Kendra was still fucking huge, I could handle her easier now.

I noticed an odd look in Holly's eyes at that moment and I laughed.

"What's that look for," I asked.

"Ugh," she chuckled, "I'm horny."

I started cracking up laughing, and she lowered her head, silently laughing as well.

"It's not funny!" she finally yelled with a big grin, "You got laid last night. I haven't had any since the New Years Eve Party. That's almost a month ago."

"Well... we could probably remedy that... if you want," I said quietly.

"That's... what I was hoping for." she replied with a catch in her throat.

She put out her cigarette in the ashtray on the table as I motioned for her to come over to me. Holly seemed so beautiful, yet so vulnerable, as she stood up, moved around the table to sit on my lap, and draped her arms around my neck. Leaning in close, she kissed me hard on the lips, and I kissed her back with passion. Our lips gradually parted and she sighed.

"It's been way too long Jay," she whispered breathlessly.

I stood up and gently lifted her up with me, as I walked out of the kitchen and back to the couch where I laid her down on her back. Crouching down over her, I resumed our kissing, turning it into a straight up make out session. My hand snaked its way up under her t-shirt, and began to fondle her breasts. She moaned, running her hands up and down my back, then pushing me back slightly, sat up to pull her shirt over her head and threw it across the room.

I pushed her back again, and slipped her shorts off too. I paused to gaze at her gorgeous form and saw the outline of her very hard cock through her panties. My own cock responding to the sight, I rubbed her smooth legs for a few moments before slipping her panties off and freeing her throbbing erection.

I started kissing my way down her breasts, and her stomach, until I had slipped below her waist and began teasing the head of her shaft with my tongue. Groaning loudly, Holly's back arched as I licked her cock. My tongue moved up and down the length of her shaft, all the way down to her balls and then right back up to the tip once again.

I moved down again, and this time started focusing on her balls. I licked them both excitedly, before sucking on them each one at a time. She ran her hand loosely through my hair, her breathing picking up some from my oral attentions.

Once again, I was working my way back up to the tip and this time I wrapped my lips around her and swallowed her whole.

"F-Fuck," she gasped.

I started moving up and down, sucking her cock, my lips gliding back and forth over her. I slowly worked her all the way to the back of my throat without choking, and started massaging her with my throat muscles. I was enjoying the reaction I was getting from her, and to add to it, I reached up and started playing with her nipples as I continued to deep throat her.

"Oh Jay... yeah baby... just like that,"

She pulled at my hair, forcing herself a little deeper down my throat as I felt her begin to shake underneath of me. Her cock started to swell, and I could already taste her sweet pre-cum... I wanted her to cum so badly.

Up and down, over and over, I bobbed my head, sucking faster and harder, all while I was still teasing her nipples. Her shaking got more intense, gyrating her hips, thrusting in and out of my mouth, her balls were mashed up against my chin. Finally, she thrust all the way down my throat and held herself there, trembling as she cried out in pleasure and exploded. Her cum shot straight down my throat, without even giving me a chance to taste her, which left me somewhat disappointed.

As I felt her body settle underneath of me, I came back up for air and started licking her shaft clean.

"Mmhm," she moaned, so relieved, "Good boy, clean me up baby."

I licked up all that remained and came up to give her a kiss on the lips, as she embraced me, wrapping her arms around me, kissing deeply. She could feel my cock poking at her thigh through my pants, and she giggled, reaching down and giving it a firm squeeze.

"Okay... your turn now, baby," she said with a devilish look in her eyes.

I wasn't going to say no, that was for sure. She pushed me off of her, and onto my back, yanking my pants off along with my boxers and swallowing my whole cock in one swift move. I moaned at the warmth of her lips around my swollen head, and she started working my cock with quick strokes and plenty of deep throat action.

Somewhere along the line, she had turned her body around so that her ass was now up in my face, in a 69 position. That was perfectly okay with me, though I was surprised to see that her own cock was once again hard as a rock so soon.

I reached up and swallowed her, and now we were going down on each other at the same time. As I sucked her cock, I admired the beautiful sight of her sexy smooth ass hovering above my face. I reached up and gave it a slap, causing her to jump with surprise and producing the most wonderful giggle.

I then gave it a firm squeeze before I spread her cheeks and continued sucking her off. I gently traced my finger over her hole, teasing her with what she knew I really wanted.

Holly stopped sucking, and released my cock from her mouth with a loud wet popping sound, while glancing back at me over her shoulder. I slipped my finger into her warm, tight ass and began rubbing her prostate, her dick still lodged in my throat and her hand still pumping my own hard cock. I carefully worked a second finger into her ass, spreading her open and started to fuck her with my fingers.

I thrust them in and out in an irregular pattern, rubbing her prostate, sucking hard at her throbbing erection until finally she cried out, and started to cum yet again. I pulled her halfway out of my mouth, just far enough so that she wasn't lodged in my throat at least, so that this way I might enjoy the taste of her cum before I downed it. So as she finished, I swallowed it all down... seeing this she laughed, still out of breath.

"Sure hope you're done teasing me now," she whined, "'cause I really want that fucking cock of yours in my ass right now!"

I gave her ass another smack, and she laughed and slid off of me, leaning over the arm of the couch with her beautiful ass, pointing straight at me. I reached under one of the cushions and pulled out a bottle of lube that I knew she kept stashed there, and proceeded to pour some all over my cock and an additional squirt on her asshole. Once we were both prepped, I positioned myself behind her, gripping her by the hips, and eased my way into her.

We both groaned with my cock sinking straight into her sweet, tight hole. I was buried balls deep inside of her now, and I pulled a few inches back and then thrust right back into her. Within seconds, I was pounding her ass from behind with long hard strokes, our bodies slapping together and the couch creaking underneath of us.

The apartment was filled with the sounds of her soft moans, and my grunting as I fucked her. I reached underneath to find her hard once again, and started stroking her dick, which was leaking pre-cum at this point. She started pushing back to meet each of my thrusts, gyrating her ass against me.

"Fuck me baby," she begged. "Fuck me harder!"

I gave her what she wanted, pounding as hard and as fast as I could manage, showing no more mercy and she loved every second of it as much as I did. I could feel myself quickly getting close, and judging by the sound coming from behind her lips, and her throbbing cock in my hand, I could tell she was getting pretty close as well.

"Cum for me Jay... cum inside of me baby,"

My balls started to tighten up, and I buried myself deep inside of her, grunting loudly as I erupted, spraying her insides with my semen. As if on cue, just as I burst, Holly cried out underneath of me, trembling and she too started to cum. She covered my hand with her thick, warm jizz and I wondered if she would ever stop.

I laughed silently, proud of myself for having just made her cum three times in quick succession... all in one sex session.

At last, both of our orgasms subsiding, I withdrew my cock from her ass and turned her over onto her back. She took the hand that I had been using to jack her off, and licked her cum off of my fingers... god that was so fucking hot to watch.

I leaned down and kissed her on the lips, my tongue sliding into her mouth as we stayed that way for a few moments, just making out together.

Then the doorbell rang, startling the both of us and causing me to jump off the couch quickly. I looked around, suddenly remembering that we had ordered pizza nearly an hour ago... this was probably the delivery guy. Holly blushed, pulling the sheets over her as I slipped my boxers and jeans back on and walked towards the door to open it for the delivery guy.

I paid him, took the large box from him and quickly shut the door turning around to find Holly sitting up on the couch, trying not to burst out laughing the whole time.

"Just what are you laughing at," I asked, walking towards the kitchen with a smile of my own.

"Oh nothing," she said, "just a shame he didn't get here a few seconds sooner... maybe he would have liked to watch the two of us have fun."

"Somehow I highly doubt that Holly," I said chuckling.

As we walked to the kitchen she slapped my ass, and I jumped in surprise. I looked back at her and noticed she hadn't even bothered putting any clothes on. I put the pizza on the counter as she walked over to the cabinet and grabbed two plates. She stood up on her toes to reach the plates, giving me a perfect view of that fantastic bubble butt over strong gorgeous legs, and her hole still gaping from my cock.

"Why are you still in your jeans," she said putting the plates on the table, "You already answered the door, let's enjoy the rest of our night without the burden of clothes, shall we?"

"I think I like that idea," I agreed.

Holly walked back out to the couch and sat down with her food, as I slipped out of my pants once again and grabbed my plate, taking a seat next to her. We clicked on the TV and decided to watch a couple of episodes of Family Guy while we ate our dinner together. After the second episode, I got up to take our plates out to the kitchen and set them in the sink, before turning and walking back to the living room. There, I found Holly sprawled out on the sofa, stroking her once again hard cock, and grinning at me.

"You're ready to go again," I asked, incredulously.

"I don't know what it is baby," she said laughing "you just make me so fucking horny."

"I can see that babe," I replied, my own cock stirring at the sight.

"Do me a favor, turn around and let me see that handsome butt again?"

I knew where this was heading, but I had no problem giving her what she wanted. I slowly turned around, and bent over just slightly, giving her a nice glimpse of my ass. I heard her groaning as she continued stroking her cock, and I spread my cheeks for her to see it all better.

"Oh f-fuck," she said sexily, "get that sweet ass over here babe."

I walked over towards her as she sat up, sitting on the edge of the cushion with my cock right in her face. She took me into her mouth, sucking and stroking, swirling her tongue around the head. I sighed, leaning my head back as she grabbed my ass and pulled me deeper into her throat. She kept that up for about a minute and a half, before she turned me around and instructed me to bend over. I bent down, my ass right in her face, and she spread my cheeks.

I felt her warm, wet tongue, licking up and down my crack, teasing my hole and getting me nice and wet for what I knew she wanted to do next.

Sure enough, after a few moments of her tongue probing my hole, she began pushing her finger into me and I tensed up slightly. She inched her finger in slowly, until she had it all the way in up to the knuckle. She started slowly moving it in and out of me for a few seconds, while reaching around with her other hand to start stroking my semi-erect cock until it was fully hard.

Continuing to stretch my hole, she carefully inserted a second finger and pushed up against my prostate gland. Jumping in surprise, I moaned from the feeling of pressure now, with my cock swelling up and throbbing painfully.

Holly then removed both fingers, and I heard her squirting some of the lube into her hands. I looked back over my shoulder, and watched as she stroked her cock, lubing it up nice and good and then leaned forward to spread my cheeks again. She used what was left of the lube on her hands to smear it all over my ass, working her fingers deep into me again and getting me as wet as possible. She applied more lubrication, to the point where I was pretty sure I was ready.

Holly now got up and stood behind me as she slapped my ass, and while I laughed, it had also stung a little. She took hold of her cock and slowly started to guide it into my asshole. I bit my lip and groaned, as she pushed into me, inch by inch until she was as deep inside as she could manage.

I got a very full and pleasant feeling, it had been a while since I'd been fucked. Perhaps a little too long in my opinion, as I realized how much I had missed this feeling. Holly was pounding me real good, thrusting with long hard strokes deep into my ass, while kissing me on the neck. She bent me over the side of the couch at one point, and with the both of us really into it now, she started stroking my cock, jerking me off as she fucked me.

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